TW200915350A - Aqueous dispersions of electrically conducting polymers containing inorganic nanoparticles - Google Patents
Aqueous dispersions of electrically conducting polymers containing inorganic nanoparticles Download PDFInfo
- Publication number
- TW200915350A TW200915350A TW097127994A TW97127994A TW200915350A TW 200915350 A TW200915350 A TW 200915350A TW 097127994 A TW097127994 A TW 097127994A TW 97127994 A TW97127994 A TW 97127994A TW 200915350 A TW200915350 A TW 200915350A
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- composition
- acid
- layer
- polymer
- Prior art date
Links
- 229920001940 conductive polymer Polymers 0.000 title claims abstract description 46
- 239000002105 nanoparticle Substances 0.000 title claims abstract description 24
- 239000006185 dispersion Substances 0.000 title claims abstract description 23
- 239000002322 conducting polymer Substances 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 52
- 229920000642 polymer Polymers 0.000 claims abstract description 47
- 239000002253 acid Substances 0.000 claims abstract description 46
- -1 poly(selenophene) Polymers 0.000 claims description 53
- 229920001577 copolymer Polymers 0.000 claims description 21
- 239000000872 buffer Substances 0.000 claims description 20
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 239000002245 particle Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 229910044991 metal oxide Inorganic materials 0.000 claims description 7
- 150000004706 metal oxides Chemical class 0.000 claims description 7
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229920000128 polypyrrole Polymers 0.000 claims description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000123 polythiophene Polymers 0.000 claims description 4
- 229920000767 polyaniline Polymers 0.000 claims description 3
- 239000000052 vinegar Substances 0.000 claims description 3
- 235000021419 vinegar Nutrition 0.000 claims description 3
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical group FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 2
- HVOAFLJLVONUSZ-UHFFFAOYSA-N 2-ethylperoxythiophene Chemical compound CCOOC1=CC=CS1 HVOAFLJLVONUSZ-UHFFFAOYSA-N 0.000 claims description 2
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- 229910052712 strontium Inorganic materials 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- 239000004408 titanium dioxide Substances 0.000 claims description 2
- 229910001935 vanadium oxide Inorganic materials 0.000 claims description 2
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 claims 2
- KZWJWYFPLXRYIL-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)F KZWJWYFPLXRYIL-UHFFFAOYSA-N 0.000 claims 1
- 206010021143 Hypoxia Diseases 0.000 claims 1
- 240000007594 Oryza sativa Species 0.000 claims 1
- 235000007164 Oryza sativa Nutrition 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 claims 1
- 230000001146 hypoxic effect Effects 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 239000008267 milk Substances 0.000 claims 1
- MHQDVISTPJHBIP-UHFFFAOYSA-N non-8-ene-2-sulfonic acid Chemical compound CC(CCCCCC=C)S(=O)(=O)O MHQDVISTPJHBIP-UHFFFAOYSA-N 0.000 claims 1
- 229920002580 poly(selenophene-2,5-diyl) polymer Polymers 0.000 claims 1
- 235000009566 rice Nutrition 0.000 claims 1
- NYERMPLPURRVGM-UHFFFAOYSA-N thiazepine Chemical compound S1C=CC=CC=N1 NYERMPLPURRVGM-UHFFFAOYSA-N 0.000 claims 1
- 239000010410 layer Substances 0.000 description 123
- 239000000463 material Substances 0.000 description 58
- 239000000178 monomer Substances 0.000 description 47
- 125000000217 alkyl group Chemical group 0.000 description 34
- 229910052739 hydrogen Inorganic materials 0.000 description 31
- 239000001257 hydrogen Substances 0.000 description 31
- 125000003118 aryl group Chemical group 0.000 description 30
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical group C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 25
- 229920000557 Nafion® Polymers 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 125000003342 alkenyl group Chemical group 0.000 description 19
- 238000000151 deposition Methods 0.000 description 18
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- 229910052717 sulfur Inorganic materials 0.000 description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 12
- 230000002378 acidificating effect Effects 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 239000002243 precursor Substances 0.000 description 12
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 150000007942 carboxylates Chemical group 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- 239000011669 selenium Substances 0.000 description 10
- 230000008021 deposition Effects 0.000 description 9
- 229910052711 selenium Inorganic materials 0.000 description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 9
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229910052714 tellurium Inorganic materials 0.000 description 8
- 238000012546 transfer Methods 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 125000001033 ether group Chemical group 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 239000004065 semiconductor Substances 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- KVGOXGQSTGQXDD-UHFFFAOYSA-N 1-decane-sulfonic-acid Chemical group CCCCCCCCCCS(O)(=O)=O KVGOXGQSTGQXDD-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 238000005240 physical vapour deposition Methods 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000003396 thiol group Chemical class [H]S* 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 125000003158 alcohol group Chemical group 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000005110 aryl thio group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000000084 colloidal system Substances 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000003495 polar organic solvent Substances 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- UPGATMBHQQONPH-UHFFFAOYSA-N 2-aminooxycarbonylbenzoic acid Chemical group NOC(=O)C1=CC=CC=C1C(O)=O UPGATMBHQQONPH-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000005229 chemical vapour deposition Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 229920000547 conjugated polymer Polymers 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000002309 gasification Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000004404 heteroalkyl group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 239000004575 stone Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229910021653 sulphate ion Inorganic materials 0.000 description 3
- HTOFKHJTNDESBL-UHFFFAOYSA-L zinc tellurite Chemical compound [Zn+2].[O-][Te]([O-])=O HTOFKHJTNDESBL-UHFFFAOYSA-L 0.000 description 3
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- SVZMCEWNLVICKU-UHFFFAOYSA-N 2-bis(8-hydroxyquinolin-2-yl)alumanylquinolin-8-ol Chemical compound Oc1cccc2ccc(nc12)[Al](c1ccc2cccc(O)c2n1)c1ccc2cccc(O)c2n1 SVZMCEWNLVICKU-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 206010036790 Productive cough Diseases 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229930013930 alkaloid Natural products 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- JWVAUCBYEDDGAD-UHFFFAOYSA-N bismuth tin Chemical compound [Sn].[Bi] JWVAUCBYEDDGAD-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000000306 component Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000007766 curtain coating Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000006612 decyloxy group Chemical group 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000004815 dispersion polymer Substances 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 229920002313 fluoropolymer Polymers 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000007756 gravure coating Methods 0.000 description 2
- 238000007646 gravure printing Methods 0.000 description 2
- 210000000003 hoof Anatomy 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 229910052747 lanthanoid Inorganic materials 0.000 description 2
- 150000002602 lanthanoids Chemical class 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000005429 oxyalkyl group Chemical group 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 238000007764 slot die coating Methods 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 210000003802 sputum Anatomy 0.000 description 2
- 208000024794 sputum Diseases 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- AGGJWJFEEKIYOF-UHFFFAOYSA-N 1,1,1-triethoxydecane Chemical compound CCCCCCCCCC(OCC)(OCC)OCC AGGJWJFEEKIYOF-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- YBQZXXMEJHZYMB-UHFFFAOYSA-N 1,2-diphenylhydrazine Chemical compound C=1C=CC=CC=1NNC1=CC=CC=C1 YBQZXXMEJHZYMB-UHFFFAOYSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- YZJJFHCVOBMNQJ-UHFFFAOYSA-N 1-hydroperoxydecane Chemical compound CCCCCCCCCCOO YZJJFHCVOBMNQJ-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- VMAUSAPAESMXAB-UHFFFAOYSA-N 2,3-bis(4-fluorophenyl)quinoxaline Chemical compound C1=CC(F)=CC=C1C1=NC2=CC=CC=C2N=C1C1=CC=C(F)C=C1 VMAUSAPAESMXAB-UHFFFAOYSA-N 0.000 description 1
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- JINGUCXQUOKWKH-UHFFFAOYSA-N 2-aminodecanoic acid Chemical group CCCCCCCCC(N)C(O)=O JINGUCXQUOKWKH-UHFFFAOYSA-N 0.000 description 1
- SVQOKUWDNBOKFD-UHFFFAOYSA-N 2-ethenoxyethanesulfonyl fluoride Chemical compound FS(=O)(=O)CCOC=C SVQOKUWDNBOKFD-UHFFFAOYSA-N 0.000 description 1
- HONWGFNQCPRRFM-UHFFFAOYSA-N 2-n-(3-methylphenyl)-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HONWGFNQCPRRFM-UHFFFAOYSA-N 0.000 description 1
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- GXXNMQBOGJLFAY-UHFFFAOYSA-N 2-octadecoxycarbonylbenzoic acid Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(O)=O GXXNMQBOGJLFAY-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- YSYRISKCBOPJRG-UHFFFAOYSA-N 4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole Chemical compound FC1=C(F)OC(C(F)(F)F)(C(F)(F)F)O1 YSYRISKCBOPJRG-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- 229920001621 AMOLED Polymers 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000003341 Bronsted base Substances 0.000 description 1
- XTOMFMNDPPZOCN-UHFFFAOYSA-N C1(=CC=CC=C1)NNC1=CC=CC=C1.C(C)N(C1=CC=C(C=O)C=C1)CC Chemical compound C1(=CC=CC=C1)NNC1=CC=CC=C1.C(C)N(C1=CC=C(C=O)C=C1)CC XTOMFMNDPPZOCN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical group OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- YHBTXTFFTYXOFV-UHFFFAOYSA-N Liquid thiophthene Chemical compound C1=CSC2=C1C=CS2 YHBTXTFFTYXOFV-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- VHWCIQOLKZEHQO-UHFFFAOYSA-N OC=1C=CC=C2C=CC(=NC12)C1=C(C(=C(C2=CC3=CC=CC=C3C=C12)C1=NC2=C(C=CC=C2C=C1)O)C1=NC2=C(C=CC=C2C=C1)O)C1=NC2=C(C=CC=C2C=C1)O Chemical compound OC=1C=CC=C2C=CC(=NC12)C1=C(C(=C(C2=CC3=CC=CC=C3C=C12)C1=NC2=C(C=CC=C2C=C1)O)C1=NC2=C(C=CC=C2C=C1)O)C1=NC2=C(C=CC=C2C=C1)O VHWCIQOLKZEHQO-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
- 150000001356 alkyl thiols Chemical class 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 150000001504 aryl thiols Chemical class 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- SINKOGOPEQSHQD-UHFFFAOYSA-N cyclopentadienide Chemical compound C=1C=C[CH-]C=1 SINKOGOPEQSHQD-UHFFFAOYSA-N 0.000 description 1
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical group CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 1
- XAKXZZPEUKNHMA-UHFFFAOYSA-N decyl decanoate Chemical compound CCCCCCCCCCOC(=O)CCCCCCCCC XAKXZZPEUKNHMA-UHFFFAOYSA-N 0.000 description 1
- 108700041286 delta Proteins 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000011263 electroactive material Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000000879 imine group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 238000001659 ion-beam spectroscopy Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 238000001755 magnetron sputter deposition Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- QLOAVXSYZAJECW-UHFFFAOYSA-N methane;molecular fluorine Chemical group C.FF QLOAVXSYZAJECW-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000002114 nanocomposite Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- RKCAIXNGYQCCAL-UHFFFAOYSA-N porphin Chemical compound N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 RKCAIXNGYQCCAL-UHFFFAOYSA-N 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 229910002059 quaternary alloy Inorganic materials 0.000 description 1
- 150000004060 quinone imines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- MIECFAZUSQCOEL-UHFFFAOYSA-N sulfane;hydrofluoride Chemical group [F-].[SH3+] MIECFAZUSQCOEL-UHFFFAOYSA-N 0.000 description 1
- IWOKCMBOJXYDEE-UHFFFAOYSA-N sulfinylmethane Chemical compound C=S=O IWOKCMBOJXYDEE-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000004354 sulfur functional group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical group FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- PFZLGKHSYILJTH-UHFFFAOYSA-N thieno[2,3-c]thiophene Chemical compound S1C=C2SC=CC2=C1 PFZLGKHSYILJTH-UHFFFAOYSA-N 0.000 description 1
- NMFKEMBATXKZSP-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2.S1C=CC2=C1C=CS2 NMFKEMBATXKZSP-UHFFFAOYSA-N 0.000 description 1
- BHBIPLOIWQSVID-UHFFFAOYSA-N thiohypofluorous acid Chemical compound SF BHBIPLOIWQSVID-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- WGIWBXUNRXCYRA-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WGIWBXUNRXCYRA-UHFFFAOYSA-H 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000003631 wet chemical etching Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011746 zinc citrate Substances 0.000 description 1
- 229940068475 zinc citrate Drugs 0.000 description 1
- 235000006076 zinc citrate Nutrition 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y20/00—Nanooptics, e.g. quantum optics or photonic crystals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/128—Intrinsically conductive polymers comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/301—Details of OLEDs
- H10K2102/331—Nanoparticles used in non-emissive layers, e.g. in packaging layer
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nanotechnology (AREA)
- Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biophysics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials Engineering (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Composite Materials (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Description
200915350 九、發明說明： 【發明所屬之技術領域】 η。之本發明係關於含有無機奈米顆粒之導電聚合物 組合物及其在電子器件中之應用。 【先前技術】 電子器件界疋一類包括活性層之產品。有機電子器件具 有至少-層有機活性層。該等器件將電能轉化為輕射（例 如發光二極體）’經由電子過程檢測信號，將輻射轉化為 電能（例如光伏打電池），或包括一或多層有機半導體層。 有機發光二極體（OLED)係包含能電致發光之有機層的 有機電子器件。含有導電聚合物之〇LED可具有以下組 態： ' 陽極/緩衝層/EL材料/陰極 以及電極之間之額外層。陽極通常係能夠將電洞注入£匕材 料中之任一材料，例如銦/錫氧化物（IT〇)。陽極視需要支 撐於玻璃或塑料基板上。EL材料包括螢光化合物、螢光及 磷光金屬錯合物、共軛聚合物及其混合物。陰極通常係能 將電子注入EL材料之任何材料（例如Ca*Ba)。具有在1〇-3 至10·7 S/cm範圍内之低電導率之導電聚合物通常用作與諸 如ITO等導電無機氧化物陽極直接接觸之緩衝層。 業内仍需要經改良緩衝層材料。 【發明内容】 本發明提供包含至少一種摻雜有至少一種高度氟化的酸 聚合物之導電聚合物之水性分散液的組合物，且其中分散 133332.doc 200915350 有無機奈米顆粒。 在另-實施例令提供自上述組合物形成之膜。 在另一實施例中提供包含至少-層包含上述膜之層之電 子器件。 【實施方式】 多個態樣及實施例閣述於本文中且僅係例示性而非限制 性。閱讀本說明書後習該項技術者應理解，在不背離 本發明範_情況下亦可存在其他態樣及實施例。 根據以下實施方式及中請專利範圍可明瞭任何―或多個 實施例之其他特徵及優點。實施方式首先闊述術語之定義 及闡釋’之後闡述導電聚合物、高度氣化的酸聚合物、益 機奈米顆粒、經摻雜導電聚合物組合物之製備、緩衝層:、 電子器件，且最後闡述實例。 1·說明書及申請專利範圍中所用術語之定義及闞釋 在詳細闡述下文所述實施例之前，定義或閣釋某 語。 — 術語"導體，，及其變化形式欲意指具有電子特性之層材 料、部件或結構，以使在電流流經此層材料、部件或結構 時電勢無明顯下降。術語意欲包括半導體。在某些實：例 中’導體可形成電導率為至之層。 術語"導電性”在表示材料時意指在不添加碳黑或導電金 屬顆粒之情況下固有地或本質上能導電之材料。 術語”聚合物"欲意指具有至少一種重複單體單元之材 料。術語包括僅具有-種或一類單體單元之均聚物、及具 133332.doc 200915350 有兩種或更多種不同單體單元之共聚物，包括自不同種類 單體單元形成之共聚物。 術語”酸聚合物"係指具有酸性基團之聚合物。 術語”酸性基團"係指能離子化以將氫離子供給布忍斯特 (Br0nsted)鹼之基團。 術《。间度氟化”係指化合物中至少9〇%與碳鍵結之可用 氫經氟替代。 術'吾70全氟*化”及"全氟化"可互換使用且係指化合物中 所有與碳鍵結之可用氫皆經氟替代。 組合物可包含一或多種不同導電聚合物及一或多種不同 高度氟化的酸聚合物。 術語"經摻雜"在表示導電聚合物時欲意指導電聚合物具 有聚合抗衡離子以平衡導電聚合物上之電荷。 術語"經摻雜導電聚合物”欲意指導電聚合物及與其相連 之聚合抗衡離子。 術語"層"與術語"膜”可互換使用且係指覆蓋期望區域之 塗層。該術語不受尺寸限制。區域可大至整個器件，或小 至諸如實際視覺顯示器等具體功能區域，或小至單一子像 素。層及膜可係藉由任何習知沈積技術來形成，其包括氣 相沈積、液相沈積（連續及不連續技術）、及熱轉移。 術奈米顆粒"係指粒度小於1 00 nm之材料。在某此實 施例中，粒度小於10 nm。在某些實施例中，粒度小一於5 nm ° ' 術語，’水性，，係指液體大部分係水，且在一實施例中至少 133332.doc 200915350 約40重量& 水。 在某些實施例中，至少約6。重量%係 节：語:：傳輸"在表示層、材料、部件或結構時欲意指 :=、部件或結構有利於正電荷相對有效地以較小 電何相失穿過該層、材料、部件或結構之厚度遷移。 術語"電子傳輪，I a 該層、材料=Λ；Γ材料、部件或結構時，意指 4。卩件或結構可促進或_於貞電荷穿過該
枓、部件或結構遷移至另一層、材料、部件或結構 術語”有機電子器件"欲意指包括一或多層半導體層或材 料之1^件。有機電子器件包括（但不限於）：⑴將電能轉化 為輻射之器件(例如發光二極體、發光二極體顯示器、二 極體雷射或發光面板)’ (2)經由電子過程檢測信號之器件 (例如光檢測器、光導電池、光敏電阻器、光電開關、光 …曰體、光電管、紅外線⑽，)檢測器、或生物感測 ™ ) (3)將輻射轉化為電能之器件（例如光伏打器件或太陽 此電池）’及（4)包括一或多個包括一或多層有機半導體層 之電子組件之器件（例如電晶體或二極體）。
本文所用術語"包含"、"包括"、，,具有"或其任何其他變 化形式皆意欲涵蓋非排他性包括之内容。舉例而言，包含 系列要素之製程、方法、物件或裝置不必僅限於彼等要 素且可包括未明確列出或該等製程、方法、物件或裝置所 口有的其他要素。此外，除非明確說明相反情況，否則 或係扣包含性”或||且不係排他性"或π。舉例而言，條件A 133332.doc 200915350 或B可藉由任一以下命題來滿足：A為真（或存在）且B為假 (或不存在）、A為假（或不存在）且B為真（或存在），及A與B 二者皆為真（或存在）。 同樣，使用"一"用於闡述本文所述之要素或組件。此舉 僅出於方便之目的及欲給出本發明範疇之概括認識。除非 明顯表示其他含義’否則此表述應理解為包括一或至少一 且單數形式亦包括複數形式。 對應於元素週期表中各欄之族編號使用見於c及c 〇/ 第 81 版（2000-2001) 中之”新符號”慣例。 除非另有說明’否則本文所用所有技術及科學術語皆具 有與熟習本發明所屬技術者通常所瞭解含義相同之含義。 在化學式中，字母Q、R、T、W、χ、γ及z係用於指示文 中所定義之原子或基團。所有其他字母皆係用於指示習用 原子符號。對應於元素週期表中各攔之族編號使用見於 CRC Handbook of Chemistry and Physics，赛％\版 中之"新符號"慣例。 對於本文未述及之範圍，已習知諸多關於具體材料、處 理方法及電路之細節且可參見關於有機發光二極體顯示 器、光源、光檢測器、光伏打及半導體部件技術之教科書 及其他來源。 2·導電聚合物 新組合物中可使用任一導電聚合物。在某些實施例中， 導電聚合物可形成電導率大於1〇-7 s/cm之膜。 133332.doc 200915350 適用於新組合物之導電聚合物係自至少—種在單獨聚合 時形成導電均聚物之單體來製備。在本文令該等單體稱作 ”導電前體單體"。在單獨聚合時形成不導電均聚物之單體 稱作"不導電前體單體"。導電聚合物可為均聚物或共聚 f。適用於新組合物之導電共聚物可自兩種或更多種導電 體或自-或多種導電前體單體與—或多種非導電前 體早體之組合來製備。 ::些實施例中，導電聚合物係自至少一種 導電則體單體來製備·、塞吩、吼略、苯胺、及多環芳= 化合物。術語"多環芳香族,,係指具有一 之 :合物。環可藉由-或多個鍵來連接，或其可稠::之 人物：Γ芳香族環"意欲包括雜芳環。”多環雜芳香族"化 D物具有至少一個雜芳環。 、化 在某些實施例中，導電聚合物係自至少 前體單體來製備：嘆吩、栖吩 種“以下之 Ο 環芳香族化合物。在本or 笨胺、及多 物在本文中自該等單體 稱作聚嗟吩、聚（碼吩）、聚（蹄吩）、聚=物分別 族聚合物。術語"多環芳香族”係指及 :::環之化合物。環可藉由-或多個鍵來連接，=上 L至-起。術語”芳香族環”意欲包括 ,1次其可 方香族”化合物具有至少一個雜 衣。'多環雜 多環芳香族聚合物係聚(。塞吩并心；在某些實施例中， 在某些實施例中，新組合物/ 單體包含以下式1: :形成導電聚合物之 J33332.doc 200915350
其中： Q 係選自由S、Se及Te組成之群；
R 經獨立選擇以在每次出現時相同或不同且其係選 自氫、烷基、烯基、烷氧基、烷醯基、烷硫基、 方軋基、烧基硫烧基、烧基芳基、芳基貌基、胺 基、烧基胺基、二烧基胺基、芳基、燒基亞續醯 基、院氧基烧基、烧基續酿基、芳硫基、芳基亞 石頁酿基、烧氧基魏基、芳基績酿基、丙烯酸基、 磷酸基、膦酸基'_素、硝基、氰基、羥基、環 氧基、矽烷基、矽氧烷基、醇基、苄基、羧酸酯 基、醚基、醚羧酸酯基、醯胺磺酸酯基、醚績酸 酯基、酯磺酸酯基及胺基曱酸酯基；或兩個R1基 團可一起形成構成3、4、5、6或7-員芳香族環或 環脂族環之伸烧基或伸稀基鏈，其中環視需要可 包括一或多個二價氮、砸、碲、硫或氧原子。 本文所用術語"烷基"係指衍生自脂肪族烴之基團且包括 未經取代或經取代之直鏈、具支鏈及環狀基團。術語，，雜 烷基"欲意指烷基，其中烷基内一或多個碳原子已經另一 原子（例如氮、氧、硫、及諸如此類）替代。術語"伸烷基” 係指具有兩個連接點之烷基。 本文所用術語"烯基”係指衍生自脂肪族烴且具有至少一 133332.doc •12- 200915350 個碳-碳雙鍵之基團，且包括可未經取代或經取代之直 鏈、具支鏈及環狀基團。術語"雜烯基，，欲意指烯基，其中 烯基内一或多個碳原子已經其他原子（例如氮、氧、硫、 及諸如此類）替代。術語”伸烯基"係指具有兩個連接點之烯 基。 本文所用以下取代基之術語係指下文所列之式. 醇基" 醯胺基” 醯胺磺酸酯基 苄基" 羧酸酯基" 醚" 醚羧酸酯基” 醚磺酸酯基" 酯磺酸酯基" 磺醯亞胺基·' 胺基甲酸酯基 -r3-oh -R3-C(0)N(R6)R6
-R3-C(〇)N(R6)R4_s〇3Z -CH2-C6H5
-R3-C(〇)〇_z或-R3-〇-c(〇)-Z -R3-(0-R5)p-〇-R5
_r3_o-r4-c(o)o-z 或-r3_〇_r4_〇_ C(0)-Z -r3-o-r4-so3z -R3-0-C(0)-R4-S03Z -R3-S〇2-NH-S〇2-R5 -r3-o-c(o)-n(r6)2 其中所有"R"基團在每次出現時皆可相同或不同且： R3為單鍵或伸烷基 R4為伸烷基 R5為烷基 R6為氫或烷基 P為0或介於1至20間之整數 133332.doc 13 200915350 2為幵、鹼金屬、鹼土金屬、n(R5)4或R5。 任一上述基團皆可另外未經取代或經取代，且任一基團 中之一或多個氫皆可經F取代，包括全氟化基團。在某些 實施例中，烷基及伸烷基具有丨-20個碳原子。 在某些實施例中’在單體中，兩個Ri 一起形成-w_ (CYlY2)m-W- ’ 其中 m係 2或 3，w係 〇、s ' Se、P〇、NR6， Y1在每次出現時係相同或不同且為氫或氟，且γ2在每次出 現時相同或不同且係選自氫、鹵素、烷基、醇基、醯胺磺 酉文基、苄基、叛酸酯基、謎基、謎緩酸酯基、喊續酸酯 基、酯磺酸酯基、及胺基曱酸酯基，其中γ基團可部分或 兀王氟化。在某些實施例中，所有γ皆為氫。在某些實施 例中聚合物為聚（3，4-伸乙基二氧基嘆吩）。在某些實施 例中，至少一個γ基團不為氫。在某些實施例中，至少一 個Υ基團係至少一個氫經F取代之取代基。在某些實施例 中’至少一個γ基團係全氟化。 在某些實施例中，單體具有式I(a): (C(R7)2),
其中： Q 係選自由S、Se及Te組成之群； 、烷基、雜 在每次出現時係相同或不同且係選自氫 133332.doc -14· 200915350 烷基、烯基、雜烯基、醇基、醯胺磺酸酯基、苄 基、羧酸酯基、醚基'醚羧酸酯基、醚磺酸酯基、 酯磺酸酯基及胺基甲酸酯基，其中前提條件係至少 一個R7不為氫，且 m係2或3。 在式1(a)之某些實施例中，m為2，一個R7為具有$個以 上碳原子之烷基，且所有其他R7皆係氫。 在式1(a)之某些實施例中，至少一個R7基團經氟化。在 某些實施例中，至少一個R7基團具有至少一個氟取代基。 在某些實施例中，R7基團經完全氟化。 在式1(a)之某些實施例中，單體之稠合環脂族環上之R7 取代基為單體提供在水中之經改良溶解性且有利於在氟化 酸聚合物存在下之聚合。 在式1(a)之某些實施例中，爪係2 , 一個R7為磺酸_伸丙 基·醚-亞曱基且所有其他R7皆為氫。在某些實施例中，瓜 係2，一個R7係丙基_醚_伸乙基且所有其他r7皆為氫。在某 些實施例巾，m係2, 一個R、甲氧基且所有其他r7皆為 氫。在某些實施例中，-個R?為石黃酸二敗亞甲基醋亞甲基 (-CH2-0-C(0)-CF2-S03H)，且所有其他 R7皆為氫。 在某些實施例中，在新組合物中欲用於形成導電聚合物 之吡咯單體包含下式II， 133332.doc -15- 200915350
其中在式II中： R1 係獨立選擇以在每次出現時相同或不同且係選自 氫、烧基、烯基、烧氧基、炫醯基、院硫基、芳氧 基、烷基硫烷基、烷基芳基、芳基烷基、胺基、烷 基胺基、二烷基胺基、芳基、烷基亞磺醯基、烷氧 基烷基、烷基磺醯基、芳硫基、芳基亞磺醯基、烷 氧基羰基、芳基確醯基、丙烯酸基、填酸基、膦酸 基、鹵素、硝基、氰基、羥基、環氧基、矽烷基、 矽氧烷基、醇基、苄基、羧酸酯基、醚基、醯胺磺 酸酯基、醚羧酸酯基、醚磺酸酯基、酯磺酸酯基及 胺基甲酸酯基；或兩個R1基團可一起形成構成3、 4、5、6或7-員芳香族環或環脂族環之伸烷基或伸 烯基鏈’該環視需要可包括一或多個二價氮、硫、 石西、蹄或氧原子；且 R2經獨立選擇以在每次出現時相同或不同且係選自 氫、烷基、烯基、芳基、烷醯基、烷基硫烷基、烷 基芳基、芳基烷基、胺基、環氧基、矽烷基、矽氧 烷基、醇基 '苄基基、羧酸酯基、醚基、醚羧酸酯 基、醚磺酸酯基、酯磺酸酯基及胺基甲酸酯基。 在某些實施例中，R1在每次出現時皆係相同或不同且其 133332.doc 16 200915350 獨立選自氫、烷基、烯基、烷氧基、環烷基、環烯基、醇 基、节基、叛酸醋基、喊基、酿胺$黃酸醋基、鲢叛酸酉旨 基、醚磺酸酯基、酯磺酸酯基、胺基甲酸酯基、環氧基、 石夕烧基、石夕氧院基、及經一或多個績酸、缓酸、丙稀酸、 磷酸、膦酸、_素、硝基、氰基、羥基、環氧基、矽烷或 矽氧烷部分取代之烷基。 在某些實施例中，R2係選自氫、烧基及經一或多個石黃 酸、羧酸、丙烯酸、磷酸、膦酸、鹵素、氰基、羥基、環 氧基、矽烷或矽氧烷部分取代之烷基。 在某些實施例中，吡咯單體未經取代且R1及R2皆為氫。 在某些實施例中，兩個R1 —起形成6 -或7 -員環脂族環， 其進一步經選自以下之基團取代：烷基、雜烷基、醇基、 苄基、羧酸酯基、醚基、醚羧酸酯基、醚磺酸酯基、畴續 酸醋基及胺基甲酸酯基。該等基團可改良單體及所產生聚 合物之溶解性。在某些實施例中，兩個R1 —起形成6_或7_ 員環脂族環，其進一步經烷基取代。在某些實施例中，兩 個R1 —起形成6_或7_員環脂族環，其進一步經具有至少^固 碳原子之烧基取代。 在某些實施例中，兩個Ri 一起形成，其中 m為2或3 ’且γ在每次出現時皆係相同或不同且係選自 氫、烷基 '醇基、节基、羧酸酯基、醯胺磺酸酯基、醚 基、醚羧酸酯基、醚磺酸酯基、酯磺酸酯基及胺基甲酸酯 基。在某些實施例中，至少一個γ基團不為氫。在某些實 施例中，至少一個Y基團為其中至少一個氫經F取代之:代 133332.doc 17 200915350 基。在某些實施例中，至少_個γ基團經全氟化‘ 電聚合物 在某些實施例中，在新組合物中欲用於形成導 之苯胺單體包含下式ΙΗ， (R1)a
^nh2 (III) (H)b-l 其中： a為0或1至4之整數； b為1至5之整數’其中前提條件係a+b=5 ;且 R1獨立經選擇以在每次出現時相同或不同且係選自氫、烷 土稀基貌氧基、烧酿基、烧硫基、芳氧基、烧基硫烧 基、烧基芳基、芳基烧基、胺基'烧基胺基、二燒基胺 基、芳基、烷基亞磺醯基、烷氧基烷基、烷基磺醯基、芳 硫基、芳基亞磺醯基、烷氧基羰基、芳基磺醯基、丙烯酸 基、磷酸基、膦酸基、鹵素、硝基、氰基、羥基、環氧 基、石夕烧基、矽氧烷基、醇基、节基、羧酸酯基、醚基、 醚羧酸酯基、醯胺磺酸酯基、醚磺酸酯基、酯磺酸酯基及 胺基曱酸醋基；或兩個Ri基團可一起形成構成3、4、5、6 或7-員芳香族環或環脂族環之伸烷基或伸烯基鏈，其中該 環視需要可包括一或多個二價氮、硫或氧原子。 在聚合時’苯胺單體單元可具有以下所示式IV(a)或式 IV(b)、或兩式之組合， 133332.doc -18· 200915350
IV(b) 在某些實施例中，苯胺單體未經取代且a=〇。 在某一實施例中，a不為〇且至少一個r1經氣化。在某些 實施例中，至少—個R1經全氟化。 在某些實施例中，力如_ &人， 在新組合物中欲用於形成導電聚合物 之稍合多環雜芳香族星拼目士 班 关早體具有兩個或更多個稠合芳香族 %，其中至少一個係雜# 雜方香族。在某些實施例中，稠合多 環雜芳香族單體具有式乂 .
其中 Q係 S、Se、Te或]vjr6 . R6為氫或烷基； R8、R9、RlRll 或不同且係選自 獨立經選擇以在每次出現時 氫、烷基、烯基、烷氧基、 皆係相 炫酿基 同 133332.doc -19- 200915350 烷硫基、芳氧基、烷基硫烷基、烷基芳基、芳基烧 基、胺基、烧基胺基、二烧基胺基、芳基、燒基亞績 醯基、院氧基烧基、烧基續酿基、芳硫基、芳基亞續 醯基、烧氧基幾基、芳基續醯基、丙烯酸基、填酸 基、膦酸基、齒素、硝基、腈基、氰基、羥基、環氧 基、矽烷基、矽氧烷基、酵基、节基、羧酸酯基、醚 基、醚羧酸酯基、醯胺磺酸酯基、醚磺酸酯基、酯磺 酸酯基及胺基甲酸酯基；且 R8與R9、119與1110、及尺1〇與Rh中至少一對一起形成構成 5或6-員芳香族環之伸烯基鏈，該環視需要可包括一或 多個二價氮、硫、碼、碲或氧原子。 在某些實施例中，稠合多環雜芳香族環單體具有選自由 下式組成之群之式：V(a)、V(b)、v(c)、v(d)、v(e)、 v(f)、v(g)、v(h)、v⑴、v⑴、及 v(k):
133332.doc -20- 200915350
其中： Q係 S、Se、Te或 NH ;且 T在每次出現時係相同或不同且係選自s、nr6、ο、 SiR62、Se、Te及 PR6 ; Y係N ;且 R6為氫或烧基。 稍合多環雜芳香族單體可另外經選自下列之基團取代： 烧基、雜烷基、醇基、节基、羧酸酯基、醚基、醚羧酸酉旨 基、醚磺酸酯基、酯磺酸酯基及胺基甲酸酯基。在某些實 i33332.doc -21 200915350 施例中，取代基係經敦化。在某些實施例中，取代基係經 完全氟化。 在某些實施例中，稠合多環雜芳香族單體係噻吩并（噻 吩）。該等化合物論述於（例如）Macrom〇lecules，34，5746- 5747 (2001)及 Macromolecules，35，7281-7286 (2002)中。 在某些實施例中’噻吩并（噻吩）係選自噻吩并（2,3_b)噻 吩、噻吩并（3,2-b)噻吩、及噻吩并（3,4_b)噻吩。在某些實 施例中，噻吩并（噻吩）單體另外經至少一個選自下列之基 團取代：烷基、雜烷基、醇基、苄基、羧酸酯基、醚基、 醚羧酸酯基、醚磺酸酯基、酯磺酸酯基及胺基甲酸酯基。 在某些實施例中，取代基係經氟化。在某些實施例中，取 代基經完全氟化。 在某些實施例中’在新組合物中欲用於形成聚合物之多 環雜芳香族單體包含式VI :
其中： 、Se、Te及 PR6 ; Q係 S、Se、Te或 NR6 ; τ係選自 S、NR6、〇、SiR62、Se、Tej E係選自伸烯基、伸芳基及伸雜芳基； R為氫或燒基； 133332.doc -22· 200915350
R12每次出現時皆係相同或不同且係選自氫、烷基、 烯基、烷氧基、烷醯基、烷硫基、芳氧基、烷基 硫烧基、烧基芳基、芳基烧基、胺基、烧基胺 基、二烷基胺基、芳基、烷基亞磺醯基、烷氧基 烷基、烷基磺醯基、芳硫基、芳基亞磺醯基、烷 氧基艘基、芳基續醯基、丙烯酸基、填酸基、膦 酸基、i素、硝基、腈基、氰基、羥基、環氧 基、矽烷基、矽氧烷基、醇基、苄基、羧酸酯 基、醚基、醚羧酸酯基、醯胺磺酸酯基、醚磺酸 S旨基、酯磺酸酯基及胺基曱酸酯基；或兩個RU 基團可一起形成構成3、4、5、6或7員-芳香族環 或環脂族環之伸炫*基或伸烯基鏈，其中該環視需 要可包括一或多個二價氮、硫、硒、碲或氧原 子0 在某些實施例中，導電聚合物係前體單體與至少一種第 二單體之共聚物。可使用任一類型之第二單體，只要其對 共聚物之期望特性無有害影響。在某些實施例中，以單體 單元之’纟《量汁，第一單體佔聚合物之5〇0/。以下。在某些實 施例中’以單體單元之總量計，第二單體佔聚合物之观 以下。在某些實施例中’以單體單元之總量計，第二單體 佔10%以下。 第二單體之實例性類型包括(但不限於)烯基、炔基、伸 方基及伸雜芳基。第二單體之實例包括（但不限於）第…亞 二嗤、嚷二唾、笨并嗔二唾、伸笨基伸乙稀基、伸笨基: 133332.doc •23- 200915350 乙炔基、比啶、一嗪、及三嗪，所有該等基團皆可進一步 經取代。 在某些實施例中，共聚物係藉由首先形成具有結構A-B-:之中間體前體單體來製造，其中AK代表相同或不同之 則體早體’且B代表第二單體。a_b_c中間體前體單體可 使用標準合成有機技術來製備，例如γ__〇、以心、 Grignard複分解反應、Suzuki、及心以虬丨偶合反應。然後 藉由中間體前體單體單獨或與一或多種額外前體單體之氧 化聚合來形成共聚物。 在某些實施例中，導電聚合物係選自由以下組成之群： 聚噻吩、聚吡咯、聚合稠合多環雜芳香族化合物、其共聚 物、及其組合。 在某些實施例中，導電聚合物係選自由以下組成之群： 聚（3，4-伸乙基二氧基噻吩;）、未經取代之聚吡咯、聚（噻吩 并（2,3-b)噻吩）、聚（噻吩并（3,2_b)噻吩）、及聚（噻吩并 (3,4-b)嗟吩）。 3.高度氟化的酸聚合物 高度氟化的酸聚合物（"HFAP")可為經高度氟化且含有具 有酸性質子之酸性基團之任一聚合物。酸性基團供應可離 子化質子。在某些實施例中，酸性質子具有小於3ipKa。 在某些實施例中，酸性質子具有小於〇之pKa。在某些實施 例中’酸性質子具有小於·5之PKa。酸性基團可與聚合物 主鍵直接連接’或其可與聚合物主鏈上之側鏈連接。1性 基團之實例包括（但不限於）叛酸基團、磺酸基團、確醯亞 133332.doc -24- 200915350 胺基團、碟酸基團、膦酸基團、及其組合。酸性基團可皆 相同，或聚合物可具有一種以上類型之酸性基團。在某些 實施例中’酸性基團係選自由以下組成之群：績酸基團、 磺酿胺基團、及其組合。 纟某些實施例中，HFAP係至少95%氟化；在某些實施例 中’其係完全氟化。 •在某些實施例中，HFAP係水溶性。在某些實施例中， HFAP可分散於水中。在某些實施例中，Η·可經有機溶 ”刺潤濕。術語"有機溶劑可调濕"係指在形成膜時，材料與 有機溶劑之接觸角不大於贼。在某些實施例中，可潤濕 材料形成可由苯基己烧潤濕之膜，其中接觸角不大於 55。。量測接觸角之方法為人所熟知。在某些實施例中， 可潤濕材料可藉由聚合酸來製備，該聚合酸自身不可潤濕 但選擇性添加劑可使其變為可潤濕。 適宜聚合物主鏈之實例包括(但不限於)聚烯烴、聚丙烯 〇 ㈣、聚甲基丙稀酸醋 '聚亞醯胺、聚酿胺、聚芳酿胺、 聚丙稀酿胺、聚苯乙浠、及其共聚物，所有該等皆係高度 氟化；在某些實施例中，係完全氟化。 在-實施例中，酸性基團係續酸基團或㈣亞胺基團。 續醯亞胺基團具有下式： "S〇2~NH~S〇2"R 其中R係烷基。 在-實施射，酸性基團位純化側鏈上。在—實施例 中，氣化側鍵係選自燒基、烧氧基、醯胺基、_、及其 133332.doc -25- 200915350 組合，所有該等皆經完全氟化。 在一實施例中，HFAP具有高度氟化烯烴主鏈、及側基 高度氟化烷基磺酸酯、高度氟化醚磺酸酯、高度氟化酯磺 酸酯、或高度氟化醚磺醯亞胺基團。在一實施例中， HFAP係具有全氟-醚-績酸側鏈之全氟烯烴。在一實施例 中，聚合物係1，1-二氟乙烯與2-(1，1-二氟-2·(三氟甲基）烯 丙氧基）-1，1,2,2-四氟乙磺酸之共聚物。在一實施例中，聚 合物為乙烯與2-(2-(1,2,2-三氟乙烯氧基）-^,2,3,3,3-六氟 丙氧基）-1，1，2,2-四氟乙磺酸之共聚物。可將該等共聚物製 備為對應績醯氟聚合物之後可將其轉化為績酸形式。 在一實施例中，HF AP係經氟化及部分確化之聚（伸芳基 醚硬）之均聚物或共聚物。共聚物可為嵌段共聚物。 在一實施例中’ HFAP係具有式IX之項醯亞胺聚合物：
其中：
Rf係選自高度氟化伸烷基、高度氟化雜伸烷基、高度 氟化伸芳基、及高度氟化伸雜芳基，其可經一或多 個謎氧取代；且 η至少為4。 在式IX之一實施例中，Rf係全氟烷基。在一實施例中，Rf 係全氟丁基。在—實施例中，1含有醚氧。在一實施例 133332.doc -26- 200915350 中，η大於1 0。 在一實施例中，HFAP包含高度氟化聚合物主鏈及具有 式X之側鏈： -OR15-S〇2-NH-(S02-N-S〇2-N)a-S02R16 (X) Η Η 其中： R15係高度氟化伸烷基或高度氟化雜伸烷基； R16係高度氟化烷基或高度氟化芳基；且 a為0或1至4之整數。 在一實施例中，HFAP具有式XI ·· (CF2-CF2)c-(CF2-CF> π (XI) 0」 (CF2-CF-0)c-(CF2)c-S02-N-(S02-(CF2)c-S02.N)c-S02R16 Η Η R16 其中：
R16係南度氣化炫《基或面度氣化芳基； c獨立地為0或自1至3之整數；且 η至少為4。 HFAP之合成闡述於（例如）以下文獻中：A. Feiring等 人，J. Fluorine Chemistry 2000, 105, 129-135 ; A. Feiring 等人，Macromolecules 2000, 33, 9262-9271 ; D. D.
Desmarteau, J. Fluorine Chem. 1995, 72, 203-208 I A. J. Appleby 等人，J. Electrochem. Soc. 1993, 140(1), 109- 133332.doc -27- 200915350 111;及〇631^咖311，美國專利第5,463,005號〇 在一實施例中，HFAP亦包含衍生自至少一種高度敦化 烯系不飽和化合物之重複單元》全氟烯烴包含2至2〇個碳 原子。代表性全氟烯烴包括（但不限於）四氟乙烯、六氣两 烯、全氟-(2,2-二甲基-1，3·二氧雜環戊烯）、全氟_(2_亞甲 基-4-甲基-1，3-二氧戊環）、CF2=CFO(CF2)tCF = CF2(其中⑽ 1或2)、&Rf’’〇CF=CF2(其tRf’'係具有i至約10個碳原子之 飽和全氟烷基）。在一實施例中，共單體係四氟乙稀。 在一實施例中，HFAP係膠體形成聚合酸。本文所用術 語"膠體形成•'係指不溶於水且在分散於水性介質中時形成 膠體之材料。膠體形成聚合酸通常具有介於約1〇,〇〇〇至約 4,000,000之間之分子量。在一實施例中，聚合酸具有約 100,000至約2,000,000之分子量。膠體粒度通常為2奈米 (rim)至約140奈米。在一實施例中，膠體之粒度為2 nm至 約30 nm。可使用任何具有酸性質子之高度氟化膠體形成 聚合材料。 可以非酸形式形成上文所述某些聚合物，例如鹽、醋、 或磺醯氟。如下文所述，可將其轉化為酸形式以供製備導 電組合物。 在某些實施例中，HFAP包括高度氟化碳主鏈及表示為 下式之側鏈 -(0-CF2CFRf3)a-〇_CF2CFRf4S03E5 其中Rf3及Rf4獨立地選自F、Cl或具有1至丨0個碳原子之高 度敗化烧基，a=〇、1或2 ’及E5。在某些情況下E5可為諸 133332.doc -28· 200915350 如Li、Na、或K等陽離子，且可將其轉化為酸形式。 在某些實施例中，HFAP可為揭示於美國專利第 3,282,875號及美國專利第4,358,545號及第4,94〇,525號中 之聚合物。在某些實施例中，HFAP包含全氟碳主鏈及表 示為下式之側鏈 -o-cf2cf(cf3)-o-cf2cf2so3e5 其中E5係如上文所定義。此類hfap揭示於美國專利第 3,282,875號中且可藉由以下方式來製備：四氟乙稀（TFE) 與全氟化乙烯基醚 CF2=CF-〇-CF2CF(CF3)-〇-CF2CF2S02F (即全氟（3,6-一氧雜-4-甲基-7-辛烯磺醯氟）(？1)]^〇17))共聚 合，且隨後藉由磺醯氟基團之水解使其轉化為磺酸根基 團，且視需要實施離子交換以將其轉換為期望離子形式。 美國專利第4,358,545號及第4,940,525號中所揭示類型聚合 物之實例具有側鏈-O-CFaCFJOsE5，其中E5係如上文所定 義。此聚合物可藉由以下方式來製備：使四氟乙烯（TFE) 與全敦化乙烯基醚CF2=CF-0-CF2CF2S02F(即全1(3-氧雜· 4-戊烯磺醯氟）（p〇pf)共聚合，隨後實施水解且視需要實 施進一步離子交換。 —類HFAP可以水性Nafion®*散液自E j如p〇nt心
Nemours and Company (Wilmington，DE)購得。 4·無機奈米顆粒 無機奈米顆粒可為絕緣體或半導體。 在某些實施例中，無機奈米顆粒係金屬硫化物或金屬氧 化物。半導體金屬氧化物之實例包括（但不限於）混合價金 133332.doc 29· 200915350 屬氧化物（例如亞錄酸鋅）、及非化學計量金屬氧化物（例如 缺氧的三氧化紹'五氧化鈒、及諸如此類)。絕緣性金屬 氧化物之實例包括(但不限於)二氧化鈦、氧化錯、三氧化 翻、氧化釩、及氧化鋁。 在某些實施例中，奈米顆粒之表面經偶合劑處理以與水 性導電聚合物相容。表面修飾劑之種類包括(但不限於)矽 烷、鈦酸鹽、鍅酸鹽、銘酸鹽及聚合物分散劑。表面修飾 劑含有化學官能團’其實例包括（但不限於）腈、胺基、氰 基、烧基胺基、院基、芳基、烯基、院氧基、芳氧二、續 ，、丙烯酸、磷酸、及上述酸之鹼金屬鹽、丙烯酸酯基、 %酸醋基、醯胺續酸酯I、喊基、㈣酸g旨基、自旨續酸醋 基、烧硫基、及芳硫基。在一實施例中，化學官能團可包 括諸如環氧基、院基乙稀基及芳基乙烯基等交聯劑以在相 鄰上層上與奈米-複合物或電洞_傳輸材料中之導電聚合物 反應。在一實施例中’表面修飾劑經氣化或全氣化，例如 四氟-乙基三氟-乙烯基-醚三乙氧基矽烷、全氟丁烷-三乙 氧基矽烷、全氟辛基三乙氧基矽烷、雙（三氟丙基）_四甲基 曱夕基胺及雙（3-二乙氧基甲石夕烧基）丙基四硫化物。 5·經摻雜導電聚合物組合物之製備 在以：論述中，導電聚合物、HFAP、及無機奈米顆粒 皆係指單數形式。然而應理解，可使用一種以上之任一或 所有該等物質。 新導電聚合物組合物係藉由首先形成經摻雜導電聚合物 然後添加無機奈米顆粒來製備。 133332.doc -30- 200915350 經#雜導電聚合物係藉由在HFAP存在下於水性介質中 使前體單體發生氧化聚合來形成。聚合反應已闡述於經公 開美國專利申請案第2004/0102577號、第2004/0127637號 及第2005/205860號中。 可將無機奈米顆粒直接以固體形式添加至經摻雜導電聚 合物分散液中。在某些實施例中，使無機奈米顆粒分散於 水/谷液中’且使此分散液與經摻雜導電聚合物分散液混 合。奈米顆粒與導電聚合物之重量比在〇1_1〇〇範圍内。
在某些實施例中，在添加無機顆粒之前或之後升高pH。 在約2之已形成pH至中性pH範圍内，經摻雜導電聚合物與 無機奈米顆粒之分散液保持穩定。在添加奈米顆粒之前， 可藉由用陽離子交換樹脂處理來調節pH。在某些實施例 中，藉由添加鹼性水溶液來調節pH。鹼之陽離子可為（但 不限於)鹼金屬、鹼土金屬、銨、及烷基銨。在某些實施 例中，鹼金屬陽離子較鹼土金屬陽離子為佳。 在下文中自纟文所述新導電組合物製備之膜稱為"本文 所述新膜T使用液體沈積技術來製備膜，包括連續及 不連續技術。連續沈積技術包括（但不限於）旋塗' 凹板塗 佈、幕塗、浸塗、槽模塗佈、喷塗 連續沈積技術包括（但不限於）嘴墨 網印刷。 、及連續喷嘴塗佈。不 印刷、凹版印刷、及絲 由此形成之膜平滑且相對透明，折射率大於Μ(在糊 nm波長下），且電導率可在1().7至1(r3s/e_圍内。 6.煖衝層 133332.doc •31 · 200915350
本發月$ f施例中提供自包含新導電聚合物組合物 之水）·生分散液沈積之緩衝層。術語"緩衝層”或"缓衝材料” 欲忍私有機電子器件中可具有一或多種功能之導電或半導 電材=，其功能包括（但不限於）平面化底層、電荷傳輪及/ 或電荷1人特性、清除諸如氧或金屬離子等雜質、及有利 於或可改良有機電子器件性能之其他態樣。術語"層，，與術 語”臈”可互換使用且係指覆蓋期望區域之塗層。該術語不 受尺寸限制。區域可大至整個器#，或小至諸如實際視覺 顯示器等具體功能區域，或小至單—子像素。層及膜可係 藉由任何習知沈積技術來形成，*包括氣相沈積、液相沈 積(連續及不連續技術)、及熱轉移。連續沈積技術包括“旦 不限於)旋塗、凹板塗佈、幕塗、浸塗、槽模塗佈、喷 塗、及連續噴嘴塗佈。不連續沈積技術包括（但不限於）喷 墨印刷、凹版印刷、及絲網印刷。 新導電聚合物組合物之經乾燥膜一般不能再分散於水 中。因此可以多層薄層形式使用緩衝層。此外，緩衝層可 經不同水溶性或水分散性材料層塗覆而不受損。令人驚訝 地’已發現包含新導電聚合物組合物之緩衝層具有經改良 在另-實施例中提供自包含摻合有其他水溶性或水分散 性材料之新導電聚合物組合物之水性分散液沈積之 層。可添加材料類型之實例包括(但不限於)聚合 :劑、有機及無機導電墨水及糊劑、電荷傳輸材 料、父聯劑、及其組合。其他水溶性或水分散性材料可為 133332.doc •32· 200915350 s單刀子或聚口物。適宜聚合物之實例包括(但不限於)導 電聚合物，例如聚噻吩、聚苯胺、聚吡咯、$乙炔、聚 (噻吩并噻吩）、及其組合。 7·電子器件 在本發明另一實施例中提供包含至少一層位於兩電接觸 層之間之電活性層之電子器件，其中該器件另外包括新緩 衝層術6吾電活性”在表示層或材料時欲意指表現電子或 冑帛射特性之層或材料。在接收輻射時，電活性層材料 丨 可發射輻射或表現電子-電洞對之濃度變化。 如巴1所示’典型器件1〇〇具有陽極層110，緩衝層120, 電丨生層丨3〇、及陰極層150。與陰極層150相鄰者為可選 電子注入/傳輸層140。 器件可包括可毗鄰於陽極層11〇或陰極層15〇之支撐件或 基板（未示出）。在大多數情況下，支撐件毗鄰陽極層110。 支撑件可為撓性的或剛性的、有機的或無機的。支撐件材 ◎ 料之實例包括（但不限於）玻璃、陶瓷、金屬及塑料膜。 %極層110為與陰極層相比可更有效注入電洞之電 極。陽極可包括含有金屬、混合金屬、合金'金屬氧化物 或混合氧化物之材料。適宜材料包括第2族元素（即Be、 Mg、Ca、Sr、Ba、Ra)、第u族元素、第4、5及6族元素 及第8-10族過渡元素之混合氧化物。若陽極層1丨〇可透 光’則可使用第12、13及14族元素之混合氧化物，例如銦 —錫氧化物。本文所用短語"混合氧化物"係指具有選自第 2族元素或第12、13或14族元素之兩種或更多種不同陽離 133332.doc -33- 200915350 子之氧化物。陽極層no材料之某些非限制性具體實例包 括（但不限於）銦-錫-氧化物（"ITO”）、銦-鋅-氧化物、紹_錫_ 氧化物、金、銀、銅及錄。陽極亦可包含有機材料，尤其 諸如聚苯胺等導電聚合物’包括如，，Flexible Hght_emitting diodes made from soluble conducting polymer" » Nature -第357卷，第477-479頁（1992年6月U日）中所述之例示性材 料。陽極及陰極中至少一個應至少部分透明以容許觀測所 產生光。 陽極層110可藉由化學或物理氣相沈積製程或旋轉澆注 製程來形成。化學氣相沈積可以經電漿加強之化學氣相沈 積（"PECVD")或金屬有機化學氣相沈積（"m〇cvd")實施 物理氣相沈積可包括所有形式之濺射，包括離子束濺射以 及電子束蒸發及電阻蒸發。物理氣相沈積之具體形式包括 rf磁控管濺射及電感_合電毁物理氣相沈積（警_ PVD")。該等沈積技術在半導體製造業中已為吾人所熟 知0 Ο 在-實施例中，在微影作業期間陽極層ιι〇經圖案化。 圖案可根據需要而改變。在施用第一電接觸層材料之前可 藉由（例如）將圖案化遮罩或光阻劑置於第—撓性複 結構上來形成圖案化層。或者，亦可以整體層形式(亦稱 為毯覆沈積）施用層，並隨後使用（例如）經圖案化光阻層及 濕化學或幹蝕刻技術來實施圖索 曰 其他圖案化製程。 ^晃、$之 緩衝層120包含本文所述新導
導電組合物。自摻雜有HFAP 133332.doc -34- 200915350 之導電聚合物製備之緩衝層一般不能由有機溶劑潤濕且折 射率低於14在460 nm波長下）。本文所述緩衝層可潤濕性 更強且由此更易於經來自非極性有機溶劑之下一層塗佈。 本文所述緩衝層之折射率亦可大於丨4(在46〇 nm下）。通常 使用熟習此項技術者熟知之各種技術將緩衝層&積於基板 上。上文所述典型沈積技術包括氣相沈積、液相沈積（連 續及不連續技術）、及熱轉移。 未顯示可選層可存於緩衝層12〇與電活性層13〇之間。此 層可包含電洞傳輸材料。電洞傳輸材料之實例由γ. Wang 概述於（例如）Kirk-〇thmer Encyclopedia of Chemical Technology(第 4版，第 18卷’第 837-860 頁，1996)中。可 使用電洞傳輸分子及聚合物二者。常用電洞傳輸分子包括 (但不限於）：4,4’，4”-三（N，N-二苯基_胺基）_三苯基胺 (TDATA) ; 4,4’，4"-三（N-3-甲基苯基_N-苯基-胺基）-三苯基 胺（MTDATA) ; N，N，-二苯基-N，N'-雙（3-曱基苯基）-[1，1，·聯 苯基]-4,4’-二胺（TPD) ; 1，1_雙[(二-4-曱苯基胺基）苯基]環 己烷（TAPC) ; N，N’-雙（4-曱基苯基）-N，N，-雙（4-乙基苯基）-[1，1'-(3,3'_二甲基）聯笨基]-4,4'-二胺（ETPD);四-(3 -甲基 苯基）-Ν，Ν，Ν’，Ν·-2,5-伸苯基二胺（PDA) ; α-苯基-4-N，N-二 苯基胺基苯乙烯（TPS);對-(二乙基胺基）苯甲醛二苯基腙 (DEH);三苯胺（TPA);雙[4-(N，N-二乙基胺基）·2_曱基苯 基](4-曱基苯基）曱烷（ΜΡΜΡ) ; 1-苯基_3_[對_(二乙基胺基） 苯乙稀基]-5-[對-(二乙基胺基）苯基]D比。坐琳（PPR或 DEASP) ; 1,2-反-雙（9Η- η卡唑-9-基）環丁烷（DCZB); 133332.doc •35· 200915350 ν，ν，ν’，ν·，("基苯基Hu，-聯 N，N，-雙（萘小基 私（TTB)， 又（本基）聯本胺（α-ΝΡΒ);及卟啉 類化δ物’例如銅献菁。當用當，门括& 骨吊用電洞傳輸聚合物包括（但不 限於）聚乙烯基味0坐、 νΛ 吁上（本基甲基）聚矽烷、聚（二氧基噻 聚本胺及聚料。亦可藉由將電洞傳輪分子（例如上 述之彼等）摻雜至諸如聚苯乙烯及聚碳酸醋等聚合物 獲得電洞傳輪聚合物。 端視器件之應用’電活性層13〇可係藉由施加電壓來激 發之發光層（例如在發光二極體或發光電化學電池中），或 係響應輻射能且在施加或不施加偏t電壓之情況下產主信 號之材料層（例如在光檢測器中）。在—實施例中，電活性 材料係有機電致發光（”EL”）材料。任何ELM料皆可用於器 件中’其包括（但；Ϊ；限於）小分子有機螢光化合物、榮光及 磷光金屬錯合物、共軛聚合物、及其混合物。螢光化合物 之實例包括（但不限於）嵌二萘、茈、紅螢烯、香豆素、其 何生物、及其混合物。金屬錯合物之實例包括（但不限於） 金屬錯合之類噁辛化合物，例如，三（8_羥基喹啉根基）鋁 (Alqd，環金屬化銥及鉑電致發光化合物，例如銥與苯基 吡啶、苯基喹啉、或苯基嘧啶配體之錯合物（如Petr〇v等 人’美國專利第6,670,645號及公開之PCT申請案WO 03/063 555及WO 2004/016710中所揭示者）及有機金屬錯合 物（例如公開之PCT申請案w〇 03/008424、WO 03/091688 及WO 03/040257中所揭示者）；及其混合物。 人在美國專利弟6,303,238號中及Burrows與Thompson在公 133332.doc -36- 200915350 開PCT申請案WO 00/7065 5及wo 01/41512中已闡述包含帶 電主體材料及金屬錯合物之電致發光層。共軛聚合物之實 例包括（但不限於）聚（伸苯基伸乙烯基）' 聚第、聚（螺二 苐）、聚嚷吩、聚（對-伸苯基）、其共聚物、及其混合物。 可選層140可用於促進電子注入/傳輸兩種作用，且亦可 用作封閉層以防止反應在層界面中止。更具體而言，層 140可促進電子遷移且在層13〇與】5〇原本可直接接觸之情 況下降低反應中止之可能性。可選層i4〇材料之實例包括 (但不限於）金屬錯合之類噁辛化合物，例如雙（2_甲基_8_喹 啉根基）（對-苯基-酚根基）鋁（III) (BA1Q)及三（8羥基喹啉根 基）鋁（Alqs);四（8-羥基喹啉根基）鍅；唑類化合物，例如 2-(4-聯苯基）_5_(4-第三丁基苯基兴^，‘噁二唑（pBD)、> (4-聯苯基）-4-苯基-5-(4-第三丁基苯基）4,2,4_三唑（TAZ)、 及1，3,5-三（苯基_2-苯并咪唑）苯（1^]31);喹噁啉衍生物， 例如2,3-雙（4-氟苯基）喹噁啉；菲咯啉衍生物，例如9，1〇· 二苯基菲咯啉（DPA)及2,9_二甲基_47_二苯基_ul〇_菲咯啉 (DDPA),及其任何一或多種組合。或者，可選層可係 無機的且包含Ba〇、UF、U2〇或諸如此類。 陰極層150係可尤其有效地注入電子或負電荷載流子之 電極。陰極層150可為功函數低於第一電接觸層（在此狀況 下私陽極層110)之任何金屬或非金屬。本文所用術語"較 低功函數"欲意指材料之功函數不大於約4 4 eV ^本文所用 術扣較回功函數"欲意指材料之功函數為至少約4 4 。 陰極層之材料可係選自第1族鹼金屬（例如Li、Na、K、 133332.doc -37- 200915350
Rb、Cs)、第2族金屬（例如Mg、Ca、Ba、或諸如此類卜 第12族金屬、鑭系元素（例如Ce、Sm、Eu、或諸如此類卜 及婀系元素（例如Th、U、或諸如此類）。亦可使用諸如 鋁、銦、紀等材料及其組合。陰極層15〇之材料之非限制 性具體實例包括(但不限於)：鋇、鋰、鈽、铯、銪、铷、 在乙、鎂、釤、及其合金及組合。 '陰極層150通常係#由化¥或物s氣相;尤㈣程來形 成。在某些實施例中，陰極層可經圖案化，如上文參照陽 極層1 10所述。 考慮到欲由該等層提供之功能，器件+之其他層可由已 知可用於該等層之任何材料來製備。 某二實施例中，封裝層（未示出）係沈積於接觸層1 5 〇 上以防止諸如水及氧等不期望組份進入器件丨〇〇。此等組 份對有機層130具有有害影響。在—實施财，封裝層係 P早壁層或膜。在-實施例中，封裝層係玻璃蓋。 儘管未繪示，但應瞭解器件100可包含額外層。或者可 使用業内％知之其他層。此外’任一上述層可包含兩層或 更多層子層或可形成疊層結構。或者，陽極層110、電洞 傳輸層120、電子傳輸層140、陰極層150、及其他層中之 某，或全部可經處理（具體而言經表面處理）以提高器件之 電何載抓子傳輸效率或其他物理特性。較佳藉由平衡下述 目標來確定各組件層材料之選擇：結合器件工作壽命因素 提供具有n器件效率之器件、製造時間及複雜性因素及其 他已為A S此項技術者所瞭解之因素。應瞭解最佳組件、 133332.doc -38- 200915350 組件組態及組成性質應由彼等普通熟習該項技術者例行確 定。 在一實施例中，不同層具有下列厚度範圍：陽極丨丨0， 5 00-5 000 A ’在一實施例中為1000-2000 A ;緩衝層120， 50-2000 A ’在一實施例中為200-1 000 A ;光活性層13〇， 10-2000 A ’在一實施例中為loo-iooo A ;可選電子傳輪声 140，50-2000 A，在一實施例中為 100-1000 A ;陰極 15〇， 200-10000 A，在一實施例中為300-5000 A。每一層之相對 厚度可影響電子-電洞重組區域在器件中之位置，且由此 影響器件之發射光譜。因此電子傳輸層之厚度應經選擇以 使電子-電洞重組區域位於發光層中。期望層厚度比可取 決於所用材料之確切性質。 之沈積’此產生各個發光像素。 。在某些OLED(稱作被動矩
活性有機膜之沈積。 在作業中，對器件100施加來自適宜電源（未繪示）之電 壓。因此電流穿過器件100中之各層。電子進入有機聚合 物層，從而釋放光子。在某些OLED(稱作主動矩陣0LED 顯示器）中，可藉由電流經過獨立地激發各光活性有機膜
。此外，材 133332.doc -39. 200915350 料、方法及實例僅係例示性而非意欲限制本發明。 應瞭解，為清楚起見，在分開實施例上下文中所述之本 發明某些特徵亦可在單一實施例中組合提供。相反，為簡 潔起見，於單一實施例上下文中所述之本發明各特徵亦可 分開提供或以子組合方式提供。此外，以範圍形式提及數 值時，其包括此範圍内之每一及各個數值。 實例
比較實例A 此比較實例闡釋未添加無機奈米顆粒之pAni/ Nafion®(聚（四氟乙烯）/全I醚磺酸）膜之低電導率及不可 潤濕性。 此實例中所用PAni/Nafion®分散液係使用EW(酸當量）為 1000之水性Nafion®膠體性分散液來製備。μ% (w/w)之 Nafion®分散液係使用與美國專利第6,15〇,426號中實例1之 部分2之程序類似之程序來製備，但溫度為約270°c且之後 經水稀釋而形成12.0% (w/w)分散液以供聚合。 在500 mL·反應釜中加入96.4 g 12%固體含量之Nafion® 刀散液（11.57 mmol SO3H基團）、1〇3 g水。使用具有雙級 推進器葉片之頂置式攪拌器以3〇〇 RPM攪拌經稀釋 ϊ
Nafion®。向經稀釋Nafion®分散液中快速添加溶於15 mL 水中之1.21 g (5.09 mmol)過硫酸鈉（Na2S208)、及溶於266 pL (9.28 mmol) HC1 及 20 mL水中之 422 pL(4.63 mmol)苯 胺。聚合反應液變得不透明且極黏稠，但在5分鐘内顏色 未發生可見變化。添加約20 mg硫酸鐵，但未出現可見變 133332.doc •40- 200915350 。…：而，在30分鐘後聚合反應液開始變成淡藍色且隨後 复為綠色。在約8小時後，將Dowex M31及D〇wex M43離 子又換樹脂各25 g及1 〇〇 g去離子水添加至聚合反應混合物 中。將混合物攪拌過夜然後用濾紙過濾。將i 〇〇 g去離子 水添加至濾液中以降低黏度。將其分為5等份。 伤保持原樣，不添加鹼。經測定，該份之pH為2，且 含有 2.88。/。（w/w) PAni/Nafion®。自 PAni/Nafion® 製備薄 膜且隨後在13CTC下於空氣中烘烤。薄膜之室溫電導率經 測定為l_2xl0·8 S/cm，其亦展示於表丄中。將一小滴甲苯 置於一片薄膜上，但甲苯自膜快速滾落，此表明非極性有 機溶劑不能潤濕膜表面。非極性溶劑通常用於發光聚合物 及發光小分子。 將0.1 M NaOH水溶液添加至第二份PH 2 PAni/Nafion® 中直至pH為5.0。此份含Na+分散液經測定含有2.89% (w/w) PAni/Nafion®。自 pH 5.0 PAni/Nafi〇n@製備之薄膜 之電導率經測定為3.8 X1 〇·8 s/cm，其亦展示於表1中。經 測§式’曱本不能潤濕PAni/Nafion®薄膜。 實例1 此實例闡述半導體奈米顆粒對增強PAni/Nafion®(聚（四 氟乙烯）/全氟謎磺酸）膜之電導率及可潤濕性之效應。 使用比較實例1中所製備pH 2及pH 5.0 PAni/Nafion®分 散液來闡釋本發明之實施例。向5.0166 g pH 2 PAni/Nafion®分散液中添加 mu g Celnax CX-Z300H-F2®(來自 Nissan Chemical Industries公司，Houston, Texas, 133332.doc 41 200915350 1；8八之亞銻酸鋅水性分散液）。€：^_23〇〇1^_172之^^為約7且 含有26.47% (w/w)亞銻酸辞顆粒，其大小小於2〇 nn^在 調配物中PAni/Nafion®聚合物與亞銻酸鋅之重量比為約 0.47。混合物形成在至少五個月内無顆粒沈澱跡象之穩定 分散液。在水乾燥後，其亦形成平滑透明膜。數據明確表 明，來自Celnax CX-Z300H-F2®之特定亞銻酸錫顆粒與 PAni/ Nafion®相容。然而，為改良粗糙度小於至少5 之 表面平滑度，欲藉由能量密度更高之方法而非簡單地將兩 種組份一起添加來改良該方法。在室溫下，含有 PAni/Nafion®及亞銻酸鋅之分散液之薄膜電導率經測定為 6·6><1(Γ4 S/cm(兩個薄膜樣品之平均值），其亦展示於表i 中。電導率增強四個以上數量級。使一片薄膜與一滴甲苯 接觸。甲苯在膜表面上快速蔓延，此顯示膜變得可由常用 非極性有機溶劑潤濕。 亦向 pH 5.0 PAni/Nafion® 中添加 CX-Z300H-F2以綠定其 對電導率及可潤濕性之效應。向5 〇666 g pH 5.〇 PAni/ Nafion®分散液中添加 υβο g Celnax cx_Z3〇〇H_F2@。在 調配物中PAni/Nafion®聚合物與亞銻酸鋅之重量比為約 0.47。混合物形成無顆粒沈澱跡象之穩定分散液。在水乾 燥後其亦形成平滑透明膜。數據明確表明來自Celnax cX_ Z300H-F2®之特定亞銻酸錫顆粒與PAni/ Nafi〇n⑧相容。然 而，為改良粗链度小於至少5 nm之表面平滑度，欲藉由能 量密度更高之方法而非簡單地將兩種組份一起添加來改良 方法。在室溫下，含有PAni/Nafion®及亞銻酸鋅之分散液 133332.doc -42· 200915350 之薄膜電導率經測定為9 3xl〇·4 S/cm(兩個薄膜樣品之平均 值），其亦展示於表1中。電導率增強四個以上數量級。使 一片薄膜與一滴甲苯接觸。曱苯在膜表面上快速蔓延，此 顯示膜變得可由常用非極性有機溶劑潤濕。 表1 CX-Z300H-F2對電導率之效應 添加CX-Z300H-F2之前分散液之阳及 陽離子 電導率(S/cm) 無 CX-Z300H-F2 含 CX-Z300H-F2 2.0/FT 1.2χ10'8 6.6x10'4 5.0/Na+ 3.8χ1〇·8 9.3 χΙΟ·4 應注意’並非需要闡述於以上概述或實例中之所有活 動，可能不需要某具體活動之某部分；及除上述活動外， 可實施一或多個其他活動。另外，活動所列之次序未必係 其實施次序。 在上述說明書中，已參考具體實施例闡述若干概念。然 而，熟習此項技術者應瞭解，可在不背離下文申請專利範 圍中所闡明本發明範疇之情況下對其實施各種修改及改 I。因此，應認為說明書及附圖具有闡釋性而非限定性意 義，且所有此等修改皆意欲包括於本發明範疇内。 上文已根據具體實施例描述了本發明之益處、其他優點 及問題之解決方案。然而，益處、優點及問題之解決方案 及任何可達成任何益處、優點或解決㈣或使之更突出之 特徵皆不應被理解為係任何或所有巾請專利範圍之關鍵、 必須或基本特徵。 133332.doc -43- 200915350 應瞭解，為清晰起見，本文在單獨實施例之上下文中所 述之某些特徵亦可在單一實施例中以組合方式來提供。相 反，為簡便起見，在單一實施例之上下文中所述之各特徵 亦可單獨或以任何子組合方式來提供。 在本文所指定各範圍内數值之使用應描述為近似值，如 同所述範圍内之最小值及最大值二者皆由詞”約”先行限定 一樣。以此方式，所述範圍可上下稍微改變以達成實質上 與範圍内之值相同的結果。同樣，當一個數值的某些要素 與不同值之彼等要素混合時，該等範圍之揭示内容意欲表 示為包括介於最小平均值與最大平均值之間之每個值在内 且包括可產生的分數值在内之連續範圍。此外，當揭示更 寬或更窄範圍時，在本發明涵蓋範圍内應使來自一範圍之 最小值與來自另一範圍之最大值相匹配，且反之亦然。 【圖式簡單說明】 ^ 本發明係以實例方式來闡釋而非受限於附圖。 圖1係有機電子器件之示意圖。 熟習此項技術者應瞭解，附圖中之卫件係出於簡單明晰 之目的來闡述，而未必按照比例繪製。舉例而言，為有助 於促進理解實施例，附圖中某虺工侔 叫Τ术二丄仟I尺寸可能相對其他 工件有所誇大。 、 【主要元件符號說明】 100 110 典型器件 陽極層 緩衝層 133332.doc -44 - 120 200915350 130 電活性層 140 可選電子注入/傳輸層 150 陰極層
133332.doc -45-
Claims (1)
- 200915350 十、申請專利範圍： 1. 一種組合物，其包含： 至少—種摻雜有至少一種高度氟化的酸聚合物之導電 聚合物之水性分散液，及 無機奈米顆粒。 2. 如凊求項1之組合物，其中該導電聚合物係選自由以下 組成之群：聚噻吩、聚（硒吩）' 聚（碲吩）、聚吡咯、聚 笨胺、多環芳香族聚合物、其共聚物、及其組合。 3. 如請求項2之組合物，其中該導電聚合物係選自由以下 組成之群：聚苯胺、聚噻吩、聚吡咯、聚合稠合多環雜 芳香族化合物、其共聚物、及其組合。 4·如請求項3之組合物，其中該導電聚合物係選自由以下 組成之群：未經取代之聚苯胺、聚（3,4_伸乙基二氧基噻 吩）、未經取代之聚吡咯、聚（噻吩并（2,3_b)噻吩）、聚（噻 呍并（3,2-b)嘆吩）、及聚（α塞吩并（3,4-b)嘆吩）。 5 ·如印求項1之組合物，其中該高度氟化的酸聚合物係至 少95%氟化。 6·如凊求項1之組合物’其中該高度氟化的酸聚合物係選 自磺酸及磺醯亞胺。 7·如請求項1之組合物，其中該高度氟化的酸聚合物係具 有全氟-醚-磺酸側鏈之全氟烯烴。 8.如請求項1之組合物’其中該高度氟化的酸聚合物係選 自由以下組成之群：1，1-二氟乙烯與2·(1，卜二氟_2 〒丞）歸丙氧基）-1，1，2,2-四氟乙磺酸之共聚物、及乙歸與 133332.doc 200915350 ΓΓ;(;，2,2-三氣乙歸氧基广1，1，2,3,3… ，，，四氟乙磺酸之共聚物。 9.如请求項1之組合物，1 Φ古 ，、中該间度氟化的酸聚合物係選 自四氟乙烯與全氟（3 6__ ^ V—乳雜甲基-7-辛烯磺酸）之共 聚物、及四氟乙烯盥全葡 '、氟（3_氧雜·4·戊烯續酸）之共聚 物。 其中該等無機奈米顆粒係半導 10.如請求項！之組合物 體。 11. 如請求項10之組合物 硫化物、金屬氧化物 12. 如請求項11之組合物 組成之群：亞銻酸辞 及其組合。 其中該等奈米顆粒係選自由金屬 及其組合組成之群。 其中該金屬氧化物係選自由以下 缺氧的三氧化鉬、五氧化二釩、 ，其中該等無機奈米顆粒係絕緣 其中該等奈米顆粒係選自由以了 氧化錯、三氧化鉬、氧化釩、氣 13.如請求項1之組合物 體。 14.如請求項13之組合物 組成之群：二氧化鈦 化紹、及其組合。 15· ^求項i之組合物其中奈米顆粒與導電聚合物之 里比係在0.1_10.0範圍内。 16·種自如請求項1之組合物製備之膜。 17·如叫求項16之臈，其在46〇 nm下之折射率大於1 4。 18. -種電子器件，其包含至少一個自如請 製備之層。 《物 I33332.doc 200915350 19. 如請求項18之器件，其中該層係緩衝層。 電活性層、 20. 如請求項19之器件，其包含陽極、缓衝層 及陰極。133332.doc
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95237207P | 2007-07-27 | 2007-07-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200915350A true TW200915350A (en) | 2009-04-01 |
Family
ID=39862953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097127994A TW200915350A (en) | 2007-07-27 | 2008-07-23 | Aqueous dispersions of electrically conducting polymers containing inorganic nanoparticles |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP2173811A1 (zh) |
| JP (1) | JP2010534739A (zh) |
| KR (1) | KR20100065302A (zh) |
| CN (1) | CN101688052A (zh) |
| TW (1) | TW200915350A (zh) |
| WO (1) | WO2009018009A1 (zh) |
Families Citing this family (634)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004029128A2 (en) | 2002-09-24 | 2004-04-08 | E.I. Du Pont De Nemours And Company | Water dispersible polythiophenes made with polymeric acid colloids |
| CN100540628C (zh) | 2002-09-24 | 2009-09-16 | E.I.内穆尔杜邦公司 | 导电有机聚合物/纳米微粒组合物及其应用方法 |
| US7351358B2 (en) | 2004-03-17 | 2008-04-01 | E.I. Du Pont De Nemours And Company | Water dispersible polypyrroles made with polymeric acid colloids for electronics applications |
| US9070884B2 (en) | 2005-04-13 | 2015-06-30 | Universal Display Corporation | Hybrid OLED having phosphorescent and fluorescent emitters |
| US8586204B2 (en) | 2007-12-28 | 2013-11-19 | Universal Display Corporation | Phosphorescent emitters and host materials with improved stability |
| US9051344B2 (en) | 2005-05-06 | 2015-06-09 | Universal Display Corporation | Stability OLED materials and devices |
| EP1981898B2 (en) | 2006-02-10 | 2019-04-10 | Universal Display Corporation | Metal complexes of imidazo[1,2-f]phenanthridine ligands for use in OLED devices |
| US8778508B2 (en) | 2006-12-08 | 2014-07-15 | Universal Display Corporation | Light-emitting organometallic complexes |
| US8115378B2 (en) | 2006-12-28 | 2012-02-14 | E. I. Du Pont De Nemours And Company | Tetra-substituted chrysenes for luminescent applications |
| US20080191172A1 (en) | 2006-12-29 | 2008-08-14 | Che-Hsiung Hsu | High work-function and high conductivity compositions of electrically conducting polymers |
| KR101634392B1 (ko) | 2007-03-08 | 2016-06-28 | 유니버셜 디스플레이 코포레이션 | 인광성 물질 |
| US9130177B2 (en) | 2011-01-13 | 2015-09-08 | Universal Display Corporation | 5-substituted 2 phenylquinoline complexes materials for light emitting diode |
| US20130032785A1 (en) | 2011-08-01 | 2013-02-07 | Universal Display Corporation | Materials for organic light emitting diode |
| EP2150524B1 (en) | 2007-06-01 | 2016-02-10 | E. I. du Pont de Nemours and Company | Chrysenes for deep blue luminescent applications |
| KR101554751B1 (ko) | 2007-06-01 | 2015-09-22 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 녹색 발광 재료 |
| JP5722036B2 (ja) | 2007-08-08 | 2015-05-20 | ユニバーサル ディスプレイ コーポレイション | リン光発光ダイオード中の単一トリフェニレン発色団 |
| EP2185532B1 (en) | 2007-08-08 | 2016-11-09 | Universal Display Corporation | Benzo-fused thiophene compounds comprising a triphenylene group |
| WO2009085344A2 (en) | 2007-12-28 | 2009-07-09 | Universal Display Corporation | Dibenzothiophene-containing materials in phosphorescent light emitting diodes |
| WO2009158555A2 (en) | 2008-06-26 | 2009-12-30 | E.I. Du Pont De Nemours And Company | Organic light-emitting diode luminaires |
| KR20110044240A (ko) * | 2008-07-22 | 2011-04-28 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 무기 나노입자를 포함하는 전기전도성 중합체의 수성 분산액 |
| WO2010027583A1 (en) | 2008-09-03 | 2010-03-11 | Universal Display Corporation | Phosphorescent materials |
| US9034483B2 (en) | 2008-09-16 | 2015-05-19 | Universal Display Corporation | Phosphorescent materials |
| EP3185333B1 (en) | 2008-09-25 | 2023-09-06 | Universal Display Corporation | Organoselenium materials and their uses in organic light emitting devices |
| US8815415B2 (en) | 2008-12-12 | 2014-08-26 | Universal Display Corporation | Blue emitter with high efficiency based on imidazo[1,2-f] phenanthridine iridium complexes |
| US8932733B2 (en) | 2008-12-19 | 2015-01-13 | E I Du Pont De Nemours And Company | Chrysene derivative host materials |
| US8263973B2 (en) | 2008-12-19 | 2012-09-11 | E I Du Pont De Nemours And Company | Anthracene compounds for luminescent applications |
| US8531100B2 (en) | 2008-12-22 | 2013-09-10 | E I Du Pont De Nemours And Company | Deuterated compounds for luminescent applications |
| US9067947B2 (en) | 2009-01-16 | 2015-06-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US8759818B2 (en) | 2009-02-27 | 2014-06-24 | E I Du Pont De Nemours And Company | Deuterated compounds for electronic applications |
| KR101561402B1 (ko) * | 2009-03-12 | 2015-10-16 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 코팅 도포를 위한 전기 전도성 중합체 조성물 |
| US8722205B2 (en) | 2009-03-23 | 2014-05-13 | Universal Display Corporation | Heteroleptic iridium complex |
| US8709615B2 (en) | 2011-07-28 | 2014-04-29 | Universal Display Corporation | Heteroleptic iridium complexes as dopants |
| US11910700B2 (en) | 2009-03-23 | 2024-02-20 | Universal Display Corporation | Heteroleptic iridium complexes as dopants |
| US8497495B2 (en) | 2009-04-03 | 2013-07-30 | E I Du Pont De Nemours And Company | Electroactive materials |
| EP2421918B1 (en) * | 2009-04-21 | 2020-08-26 | LG Chem, Ltd. | Electrically conductive polymer compositions and films made therefrom |
| KR101581991B1 (ko) * | 2009-04-24 | 2015-12-31 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 전기 전도성 중합체 조성물 및 그로부터 제조된 필름 |
| TWI609855B (zh) | 2009-04-28 | 2018-01-01 | 環球展覽公司 | 具有甲基-ｄ３取代之銥錯合物 |
| US9260657B2 (en) | 2009-05-19 | 2016-02-16 | E I Du Pont De Nemours And Company | Chrysene compounds for luminescent applications |
| US8586203B2 (en) | 2009-05-20 | 2013-11-19 | Universal Display Corporation | Metal complexes with boron-nitrogen heterocycle containing ligands |
| KR20130004558A (ko) | 2009-07-01 | 2013-01-11 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 발광 응용을 위한 크라이센 화합물 |
| TW201104357A (en) | 2009-07-27 | 2011-02-01 | Du Pont | Process and materials for making contained layers and devices made with same |
| EP2464709B1 (en) | 2009-08-13 | 2014-07-16 | E. I. du Pont de Nemours and Company | Chrysene derivative materials |
| TW201132737A (en) | 2009-08-24 | 2011-10-01 | Du Pont | Organic light-emitting diode luminaires |
| US8471247B2 (en) | 2009-08-24 | 2013-06-25 | E I Du Pont De Nemours And Company | Organic light-emitting diode luminaires |
| TW201111326A (en) | 2009-09-29 | 2011-04-01 | Du Pont | Deuterated compounds for luminescent applications |
| KR20120086319A (ko) | 2009-10-19 | 2012-08-02 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 전자적 응용을 위한 트라이아릴아민 화합물 |
| EP2491003A4 (en) | 2009-10-19 | 2015-06-03 | Du Pont | TRIARYLAMINE COMPOUNDS FOR ELECTRONIC APPLICATIONS |
| WO2011059789A2 (en) | 2009-10-29 | 2011-05-19 | E. I. Du Pont De Nemours And Company | Organic light-emitting diode luminaires |
| WO2011059463A1 (en) | 2009-10-29 | 2011-05-19 | E. I. Du Pont De Nemours And Company | Deuterated compounds for electronic applications |
| US8674343B2 (en) | 2009-10-29 | 2014-03-18 | E I Du Pont De Nemours And Company | Organic light-emitting diodes having white light emission |
| US8716700B2 (en) | 2009-10-29 | 2014-05-06 | E I Du Pont De Nemours And Company | Organic light-emitting diodes having white light emission |
| US8716699B2 (en) | 2009-10-29 | 2014-05-06 | E I Du Pont De Nemours And Company | Organic light-emitting diodes having white light emission |
| US8580394B2 (en) | 2009-11-19 | 2013-11-12 | Universal Display Corporation | 3-coordinate copper(I)-carbene complexes |
| US8617720B2 (en) | 2009-12-21 | 2013-12-31 | E I Du Pont De Nemours And Company | Electroactive composition and electronic device made with the composition |
| US8288187B2 (en) | 2010-01-20 | 2012-10-16 | Universal Display Corporation | Electroluminescent devices for lighting applications |
| US9156870B2 (en) | 2010-02-25 | 2015-10-13 | Universal Display Corporation | Phosphorescent emitters |
| US9175211B2 (en) | 2010-03-03 | 2015-11-03 | Universal Display Corporation | Phosphorescent materials |
| EP2550690B1 (en) | 2010-03-25 | 2018-12-26 | Universal Display Corporation | Solution processable doped triarylamine hole injection materials |
| WO2011136755A1 (en) | 2010-04-28 | 2011-11-03 | Universal Display Corporation | Depositing premixed materials |
| US8968887B2 (en) | 2010-04-28 | 2015-03-03 | Universal Display Corporation | Triphenylene-benzofuran/benzothiophene/benzoselenophene compounds with substituents joining to form fused rings |
| US8673458B2 (en) | 2010-06-11 | 2014-03-18 | Universal Display Corporation | Delayed fluorescence OLED |
| US8742657B2 (en) | 2010-06-11 | 2014-06-03 | Universal Display Corporation | Triplet-Triplet annihilation up conversion (TTA-UC) for display and lighting applications |
| TW201204687A (en) | 2010-06-17 | 2012-02-01 | Du Pont | Electroactive materials |
| TW201200975A (en) | 2010-06-17 | 2012-01-01 | Du Pont | Process and materials for making contained layers and devices made with same |
| CN107068914B (zh) | 2010-07-02 | 2020-05-08 | 日产化学工业株式会社 | 空穴传输组合物及相关器件和方法(i) |
| CN106887522B (zh) * | 2010-07-26 | 2018-09-18 | 默克专利有限公司 | 包含纳米晶体的器件 |
| US9435021B2 (en) | 2010-07-29 | 2016-09-06 | University Of Southern California | Co-deposition methods for the fabrication of organic optoelectronic devices |
| US20120187383A1 (en) | 2010-08-11 | 2012-07-26 | E.I. Du Pont De Nemours And Company | Electroactive compound and composition and electronic device made with the composition |
| KR101753172B1 (ko) | 2010-08-20 | 2017-07-04 | 유니버셜 디스플레이 코포레이션 | Ｏｌｅｄ를 위한 바이카르바졸 화합물 |
| US20130126852A1 (en) | 2010-08-24 | 2013-05-23 | E I Du Pont De Nemours And Company | Photoactive composition and electronic device made with the composition |
| US20120049168A1 (en) | 2010-08-31 | 2012-03-01 | Universal Display Corporation | Cross-Linked Charge Transport Layer Containing an Additive Compound |
| US8932734B2 (en) | 2010-10-08 | 2015-01-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20120138906A1 (en) | 2010-12-07 | 2012-06-07 | The University of Southern California USC Stevens Institute for Innovation | Capture agents for unsaturated metal complexes |
| TW201229010A (en) | 2010-12-13 | 2012-07-16 | Du Pont | Electroactive materials |
| EP2651942B1 (en) | 2010-12-15 | 2016-03-16 | E. I. du Pont de Nemours and Company | Electroactive 1,7- and 4,10-diazachrysene derivatives and devices made with such materials |
| KR101547410B1 (ko) | 2010-12-20 | 2015-08-25 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 전자적 응용을 위한 조성물 |
| US20130264561A1 (en) | 2010-12-20 | 2013-10-10 | E I Du Pont De Nemours And Company | Electroactive compositions for electronic applications |
| JP2014507401A (ja) | 2010-12-20 | 2014-03-27 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 電子技術応用のためのトリアジン誘導体 |
| JP5871949B2 (ja) | 2010-12-20 | 2016-03-01 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | 閉じ込め層およびそれを使って製造されるデバイスを製造するための方法および材料 |
| KR20130143627A (ko) | 2010-12-21 | 2013-12-31 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 유기 전기활성 재료 침적용 액체 조성물 |
| EP2655339A1 (en) | 2010-12-21 | 2013-10-30 | E.I. Du Pont De Nemours And Company | Electronic device including a pyrimidine compound |
| US10008677B2 (en) | 2011-01-13 | 2018-06-26 | Universal Display Corporation | Materials for organic light emitting diode |
| US8563737B2 (en) | 2011-02-23 | 2013-10-22 | Universal Display Corporation | Methods of making bis-tridentate carbene complexes of ruthenium and osmium |
| US9005772B2 (en) | 2011-02-23 | 2015-04-14 | Universal Display Corporation | Thioazole and oxazole carbene metal complexes as phosphorescent OLED materials |
| CN103476781B (zh) | 2011-02-23 | 2017-02-15 | 通用显示公司 | 新型的四齿铂络合物 |
| US8883322B2 (en) | 2011-03-08 | 2014-11-11 | Universal Display Corporation | Pyridyl carbene phosphorescent emitters |
| TW201245408A (en) | 2011-04-08 | 2012-11-16 | Du Pont | Electronic device |
| US8927308B2 (en) | 2011-05-12 | 2015-01-06 | Universal Display Corporation | Method of forming bus line designs for large-area OLED lighting |
| US8432095B2 (en) | 2011-05-11 | 2013-04-30 | Universal Display Corporation | Process for fabricating metal bus lines for OLED lighting panels |
| US8795850B2 (en) | 2011-05-19 | 2014-08-05 | Universal Display Corporation | Phosphorescent heteroleptic phenylbenzimidazole dopants and new synthetic methodology |
| US9212197B2 (en) | 2011-05-19 | 2015-12-15 | Universal Display Corporation | Phosphorescent heteroleptic phenylbenzimidazole dopants |
| US8748012B2 (en) | 2011-05-25 | 2014-06-10 | Universal Display Corporation | Host materials for OLED |
| US10079349B2 (en) | 2011-05-27 | 2018-09-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10158089B2 (en) | 2011-05-27 | 2018-12-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9755164B2 (en) | 2011-06-08 | 2017-09-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US8659036B2 (en) | 2011-06-17 | 2014-02-25 | Universal Display Corporation | Fine tuning of emission spectra by combination of multiple emitter spectra |
| US8884316B2 (en) | 2011-06-17 | 2014-11-11 | Universal Display Corporation | Non-common capping layer on an organic device |
| US9397310B2 (en) | 2011-07-14 | 2016-07-19 | Universal Display Corporation | Organice electroluminescent materials and devices |
| US9023420B2 (en) | 2011-07-14 | 2015-05-05 | Universal Display Corporation | Composite organic/inorganic layer for organic light-emitting devices |
| WO2013009708A1 (en) | 2011-07-14 | 2013-01-17 | Universal Display Corporation | Inorganic hosts in oleds |
| US9783564B2 (en) | 2011-07-25 | 2017-10-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US8926119B2 (en) | 2011-08-04 | 2015-01-06 | Universal Display Corporation | Extendable light source with variable light emitting area |
| US9493698B2 (en) | 2011-08-31 | 2016-11-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| WO2013059718A1 (en) | 2011-10-19 | 2013-04-25 | E. I. Du Pont De Nemours And Company | Organic electronic device for lighting |
| US8652656B2 (en) | 2011-11-14 | 2014-02-18 | Universal Display Corporation | Triphenylene silane hosts |
| US9193745B2 (en) | 2011-11-15 | 2015-11-24 | Universal Display Corporation | Heteroleptic iridium complex |
| US9217004B2 (en) | 2011-11-21 | 2015-12-22 | Universal Display Corporation | Organic light emitting materials |
| US9512355B2 (en) | 2011-12-09 | 2016-12-06 | Universal Display Corporation | Organic light emitting materials |
| US20130146875A1 (en) | 2011-12-13 | 2013-06-13 | Universal Display Corporation | Split electrode for organic devices |
| US8987451B2 (en) | 2012-01-03 | 2015-03-24 | Universal Display Corporation | Synthesis of cyclometallated platinum(II) complexes |
| US9461254B2 (en) | 2012-01-03 | 2016-10-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9163174B2 (en) | 2012-01-04 | 2015-10-20 | Universal Display Corporation | Highly efficient phosphorescent materials |
| US8969592B2 (en) | 2012-01-10 | 2015-03-03 | Universal Display Corporation | Heterocyclic host materials |
| US10211413B2 (en) | 2012-01-17 | 2019-02-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9118017B2 (en) | 2012-02-27 | 2015-08-25 | Universal Display Corporation | Host compounds for red phosphorescent OLEDs |
| US9054323B2 (en) | 2012-03-15 | 2015-06-09 | Universal Display Corporation | Secondary hole transporting layer with diarylamino-phenyl-carbazole compounds |
| US9386657B2 (en) | 2012-03-15 | 2016-07-05 | Universal Display Corporation | Organic Electroluminescent materials and devices |
| CN104203967A (zh) | 2012-03-23 | 2014-12-10 | E.I.内穆尔杜邦公司 | 绿色发光材料 |
| KR102123622B1 (ko) | 2012-04-02 | 2020-06-16 | 주식회사 엘지화학 | 청색 발광 화합물 |
| EP2841441A1 (en) | 2012-04-23 | 2015-03-04 | E. I. Du Pont de Nemours and Company | Blue luminescent compounds |
| US9184399B2 (en) | 2012-05-04 | 2015-11-10 | Universal Display Corporation | Asymmetric hosts with triaryl silane side chains |
| HK1208764A1 (zh) | 2012-05-15 | 2016-03-11 | Nissan Chemical Industries, Ltd. | 包括oled应用的空穴传输材料 |
| US9773985B2 (en) | 2012-05-21 | 2017-09-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9062993B2 (en) | 2012-05-22 | 2015-06-23 | E I Du Pont De Nemours And Company | Method and apparatus for liquid flow calibration check |
| EP2856128B1 (en) | 2012-05-29 | 2016-09-14 | 3M Innovative Properties Company | Humidity sensor and sensor element |
| US9670404B2 (en) | 2012-06-06 | 2017-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9502672B2 (en) | 2012-06-21 | 2016-11-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9725476B2 (en) | 2012-07-09 | 2017-08-08 | Universal Display Corporation | Silylated metal complexes |
| US9231218B2 (en) | 2012-07-10 | 2016-01-05 | Universal Display Corporation | Phosphorescent emitters containing dibenzo[1,4]azaborinine structure |
| US9059412B2 (en) | 2012-07-19 | 2015-06-16 | Universal Display Corporation | Transition metal complexes containing substituted imidazole carbene as ligands and their application in OLEDs |
| US9540329B2 (en) | 2012-07-19 | 2017-01-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9663544B2 (en) | 2012-07-25 | 2017-05-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9318710B2 (en) | 2012-07-30 | 2016-04-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US8802351B2 (en) * | 2012-07-31 | 2014-08-12 | International Business Machines Corporation | Water-dispersible electrically conductive fluorine-containing polyaniline compositions for lithography |
| US9978958B2 (en) | 2012-08-24 | 2018-05-22 | Universal Display Corporation | Phosphorescent emitters with phenylimidazole ligands |
| JP6217642B2 (ja) | 2012-08-24 | 2017-10-25 | コニカミノルタ株式会社 | 透明電極、電子デバイス、および透明電極の製造方法 |
| US8952362B2 (en) | 2012-08-31 | 2015-02-10 | The Regents Of The University Of Michigan | High efficiency and brightness fluorescent organic light emitting diode by triplet-triplet fusion |
| US10957870B2 (en) | 2012-09-07 | 2021-03-23 | Universal Display Corporation | Organic light emitting device |
| US9287513B2 (en) | 2012-09-24 | 2016-03-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9312505B2 (en) | 2012-09-25 | 2016-04-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9252363B2 (en) | 2012-10-04 | 2016-02-02 | Universal Display Corporation | Aryloxyalkylcarboxylate solvent compositions for inkjet printing of organic layers |
| US8692241B1 (en) | 2012-11-08 | 2014-04-08 | Universal Display Corporation | Transition metal complexes containing triazole and tetrazole carbene ligands |
| US9685617B2 (en) | 2012-11-09 | 2017-06-20 | Universal Display Corporation | Organic electronuminescent materials and devices |
| US9748500B2 (en) | 2015-01-15 | 2017-08-29 | Universal Display Corporation | Organic light emitting materials |
| US8946697B1 (en) | 2012-11-09 | 2015-02-03 | Universal Display Corporation | Iridium complexes with aza-benzo fused ligands |
| US9634264B2 (en) | 2012-11-09 | 2017-04-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10069090B2 (en) | 2012-11-20 | 2018-09-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9190623B2 (en) | 2012-11-20 | 2015-11-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9512136B2 (en) | 2012-11-26 | 2016-12-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9166175B2 (en) | 2012-11-27 | 2015-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9196860B2 (en) | 2012-12-04 | 2015-11-24 | Universal Display Corporation | Compounds for triplet-triplet annihilation upconversion |
| US8716484B1 (en) | 2012-12-05 | 2014-05-06 | Universal Display Corporation | Hole transporting materials with twisted aryl groups |
| US9209411B2 (en) | 2012-12-07 | 2015-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9653691B2 (en) | 2012-12-12 | 2017-05-16 | Universal Display Corporation | Phosphorescence-sensitizing fluorescence material system |
| KR102019465B1 (ko) | 2012-12-13 | 2019-09-06 | 주식회사 엘지화학 | 적층된 층을 제조하기 위한 방법 및 재료, 및 이를 사용하여 제조된 소자 |
| PL2945653T3 (pl) | 2012-12-20 | 2017-11-30 | Quick-Med Technologies, Inc. | Regeneracja powłok przeciwdrobnoustrojowych zawierających pochodne metalu przy ekspozycji na wodny nadtlenek wodoru |
| US9986742B2 (en) | 2012-12-20 | 2018-06-05 | Quick-Med Technologies, Inc. | Durable antimicrobial treatments for textiles and other substrates |
| US10400163B2 (en) | 2013-02-08 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10367154B2 (en) | 2013-02-21 | 2019-07-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9748497B2 (en) | 2013-02-25 | 2017-08-29 | E I Du Pont De Nemours And Company | Electronic device including a diazachrysene derivative |
| US8927749B2 (en) | 2013-03-07 | 2015-01-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9419225B2 (en) | 2013-03-14 | 2016-08-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9997712B2 (en) | 2013-03-27 | 2018-06-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP6314974B2 (ja) | 2013-03-29 | 2018-04-25 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、照明装置、表示装置、有機ルミネッセンス素子用発光性薄膜と組成物及び発光方法 |
| JP6350518B2 (ja) | 2013-03-29 | 2018-07-04 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、それを具備した照明装置及び表示装置 |
| WO2014157494A1 (ja) | 2013-03-29 | 2014-10-02 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
| US9537106B2 (en) | 2013-05-09 | 2017-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9735373B2 (en) | 2013-06-10 | 2017-08-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9673401B2 (en) | 2013-06-28 | 2017-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10199581B2 (en) | 2013-07-01 | 2019-02-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10121975B2 (en) | 2013-07-03 | 2018-11-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9761807B2 (en) | 2013-07-15 | 2017-09-12 | Universal Display Corporation | Organic light emitting diode materials |
| US9553274B2 (en) | 2013-07-16 | 2017-01-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9324949B2 (en) | 2013-07-16 | 2016-04-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9224958B2 (en) | 2013-07-19 | 2015-12-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20150028290A1 (en) | 2013-07-25 | 2015-01-29 | Universal Display Corporation | Heteroleptic osmium complex and method of making the same |
| US9831437B2 (en) | 2013-08-20 | 2017-11-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10074806B2 (en) | 2013-08-20 | 2018-09-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9932359B2 (en) | 2013-08-30 | 2018-04-03 | University Of Southern California | Organic electroluminescent materials and devices |
| US10199582B2 (en) | 2013-09-03 | 2019-02-05 | University Of Southern California | Organic electroluminescent materials and devices |
| US9735378B2 (en) | 2013-09-09 | 2017-08-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9748503B2 (en) | 2013-09-13 | 2017-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10003034B2 (en) | 2013-09-30 | 2018-06-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR101457304B1 (ko) * | 2013-10-07 | 2014-11-03 | 인하대학교 산학협력단 | 고유전율 절연재료의 제조방법 및 상기 고유전율 절연재료를 이용한 절연소자 |
| US9831447B2 (en) | 2013-10-08 | 2017-11-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9293712B2 (en) | 2013-10-11 | 2016-03-22 | Universal Display Corporation | Disubstituted pyrene compounds with amino group containing ortho aryl group and devices containing the same |
| US9853229B2 (en) | 2013-10-23 | 2017-12-26 | University Of Southern California | Organic electroluminescent materials and devices |
| US20150115250A1 (en) | 2013-10-29 | 2015-04-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9306179B2 (en) | 2013-11-08 | 2016-04-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9647218B2 (en) | 2013-11-14 | 2017-05-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10033000B2 (en) | 2013-11-15 | 2018-07-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10056565B2 (en) | 2013-11-20 | 2018-08-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| FR3013719B1 (fr) | 2013-11-26 | 2018-01-12 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Encre pour former des couches p dans des dispositifs electroniques organiques |
| US10644251B2 (en) | 2013-12-04 | 2020-05-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9876173B2 (en) | 2013-12-09 | 2018-01-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10355227B2 (en) | 2013-12-16 | 2019-07-16 | Universal Display Corporation | Metal complex for phosphorescent OLED |
| US9847496B2 (en) | 2013-12-23 | 2017-12-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10135008B2 (en) | 2014-01-07 | 2018-11-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9978961B2 (en) | 2014-01-08 | 2018-05-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9755159B2 (en) | 2014-01-23 | 2017-09-05 | Universal Display Corporation | Organic materials for OLEDs |
| WO2015112561A1 (en) | 2014-01-23 | 2015-07-30 | E. I. Du Pont De Nemours And Company | Electroactive metal complexes |
| US9935277B2 (en) | 2014-01-30 | 2018-04-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9590194B2 (en) | 2014-02-14 | 2017-03-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9847497B2 (en) | 2014-02-18 | 2017-12-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10003033B2 (en) | 2014-02-18 | 2018-06-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10707423B2 (en) | 2014-02-21 | 2020-07-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9647217B2 (en) | 2014-02-24 | 2017-05-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9502656B2 (en) | 2014-02-24 | 2016-11-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10403825B2 (en) | 2014-02-27 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9181270B2 (en) | 2014-02-28 | 2015-11-10 | Universal Display Corporation | Method of making sulfide compounds |
| US9673407B2 (en) | 2014-02-28 | 2017-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9590195B2 (en) | 2014-02-28 | 2017-03-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9190620B2 (en) | 2014-03-01 | 2015-11-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9397309B2 (en) | 2014-03-13 | 2016-07-19 | Universal Display Corporation | Organic electroluminescent devices |
| US10208026B2 (en) | 2014-03-18 | 2019-02-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9748504B2 (en) | 2014-03-25 | 2017-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9929353B2 (en) | 2014-04-02 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9691993B2 (en) | 2014-04-09 | 2017-06-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9847498B2 (en) | 2014-04-14 | 2017-12-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10008679B2 (en) | 2014-04-14 | 2018-06-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9450198B2 (en) | 2014-04-15 | 2016-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10256427B2 (en) | 2014-04-15 | 2019-04-09 | Universal Display Corporation | Efficient organic electroluminescent devices |
| US9741941B2 (en) | 2014-04-29 | 2017-08-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10457699B2 (en) | 2014-05-02 | 2019-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10403830B2 (en) | 2014-05-08 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10301338B2 (en) | 2014-05-08 | 2019-05-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10636983B2 (en) | 2014-05-08 | 2020-04-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP6759108B2 (ja) | 2014-05-08 | 2020-09-23 | ユニバーサル ディスプレイ コーポレイション | 安定化されたイミダゾフェナントリジン材料 |
| US9997716B2 (en) | 2014-05-27 | 2018-06-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10461260B2 (en) | 2014-06-03 | 2019-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN104021838B (zh) * | 2014-06-20 | 2016-09-07 | 上海赤龙科技有限公司 | 一种聚噻吩/混合价金属氧化物协同导电浆料及其制备方法 |
| US9911931B2 (en) | 2014-06-26 | 2018-03-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10297762B2 (en) | 2014-07-09 | 2019-05-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10566546B2 (en) | 2014-07-14 | 2020-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9929357B2 (en) | 2014-07-22 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10411200B2 (en) | 2014-08-07 | 2019-09-10 | Universal Display Corporation | Electroluminescent (2-phenylpyridine)iridium complexes and devices |
| US11108000B2 (en) | 2014-08-07 | 2021-08-31 | Unniversal Display Corporation | Organic electroluminescent materials and devices |
| US9843001B2 (en) | 2014-08-18 | 2017-12-12 | E I Du Pont De Nemours And Company | Blue luminescent compounds |
| US9944846B2 (en) | 2014-08-28 | 2018-04-17 | E I Du Pont De Nemours And Company | Compositions for electronic applications |
| US10749113B2 (en) | 2014-09-29 | 2020-08-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10135007B2 (en) | 2014-09-29 | 2018-11-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10361375B2 (en) | 2014-10-06 | 2019-07-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9397302B2 (en) | 2014-10-08 | 2016-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10854826B2 (en) | 2014-10-08 | 2020-12-01 | Universal Display Corporation | Organic electroluminescent compounds, compositions and devices |
| US10950803B2 (en) | 2014-10-13 | 2021-03-16 | Universal Display Corporation | Compounds and uses in devices |
| US9484541B2 (en) | 2014-10-20 | 2016-11-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN107074763B (zh) | 2014-10-20 | 2021-01-05 | 株式会社Lg化学 | 蓝色发光化合物 |
| US10193070B2 (en) | 2014-10-31 | 2019-01-29 | E I Du Pont De Nemours And Company | Electroactive materials |
| US10868261B2 (en) | 2014-11-10 | 2020-12-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10038151B2 (en) | 2014-11-12 | 2018-07-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10411201B2 (en) | 2014-11-12 | 2019-09-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9882151B2 (en) | 2014-11-14 | 2018-01-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9761814B2 (en) | 2014-11-18 | 2017-09-12 | Universal Display Corporation | Organic light-emitting materials and devices |
| CN107108861B (zh) | 2014-11-20 | 2019-11-12 | 株式会社Lg化学 | 空穴传输材料 |
| US10381569B2 (en) | 2014-11-25 | 2019-08-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9444075B2 (en) | 2014-11-26 | 2016-09-13 | Universal Display Corporation | Emissive display with photo-switchable polarization |
| US9450195B2 (en) | 2014-12-17 | 2016-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10253252B2 (en) | 2014-12-30 | 2019-04-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10636978B2 (en) | 2014-12-30 | 2020-04-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9312499B1 (en) | 2015-01-05 | 2016-04-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9406892B2 (en) | 2015-01-07 | 2016-08-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9711730B2 (en) | 2015-01-25 | 2017-07-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10418569B2 (en) | 2015-01-25 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10644247B2 (en) | 2015-02-06 | 2020-05-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10355222B2 (en) | 2015-02-06 | 2019-07-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10418562B2 (en) | 2015-02-06 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10177316B2 (en) | 2015-02-09 | 2019-01-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10144867B2 (en) | 2015-02-13 | 2018-12-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP5831654B1 (ja) | 2015-02-13 | 2015-12-09 | コニカミノルタ株式会社 | 芳香族複素環誘導体、それを用いた有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
| US10680183B2 (en) | 2015-02-15 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9929361B2 (en) | 2015-02-16 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10600966B2 (en) | 2015-02-27 | 2020-03-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11056657B2 (en) | 2015-02-27 | 2021-07-06 | University Display Corporation | Organic electroluminescent materials and devices |
| US10686143B2 (en) | 2015-03-05 | 2020-06-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10270046B2 (en) | 2015-03-06 | 2019-04-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9780316B2 (en) | 2015-03-16 | 2017-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9911928B2 (en) | 2015-03-19 | 2018-03-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9871214B2 (en) | 2015-03-23 | 2018-01-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP6294254B2 (ja) | 2015-03-23 | 2018-03-14 | 信越化学工業株式会社 | 導電性材料及び基板 |
| US10529931B2 (en) | 2015-03-24 | 2020-01-07 | Universal Display Corporation | Organic Electroluminescent materials and devices |
| US9972783B2 (en) | 2015-03-25 | 2018-05-15 | E I Du Pont De Nemours And Company | High energy triarylamine compounds for hole transport materials |
| US10297770B2 (en) | 2015-03-27 | 2019-05-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11495749B2 (en) | 2015-04-06 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11818949B2 (en) | 2015-04-06 | 2023-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20160293854A1 (en) | 2015-04-06 | 2016-10-06 | Universal Display Corporation | Organic Electroluminescent Materials and Devices |
| US9954174B2 (en) | 2015-05-06 | 2018-04-24 | E I Du Pont De Nemours And Company | Hole transport materials |
| US10777749B2 (en) | 2015-05-07 | 2020-09-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10403826B2 (en) | 2015-05-07 | 2019-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9478758B1 (en) | 2015-05-08 | 2016-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9859510B2 (en) | 2015-05-15 | 2018-01-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10804473B2 (en) | 2015-05-21 | 2020-10-13 | Lg Chem, Ltd. | Electron transport materials for electronic applications |
| US10109799B2 (en) | 2015-05-21 | 2018-10-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10256411B2 (en) | 2015-05-21 | 2019-04-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10418568B2 (en) | 2015-06-01 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10033004B2 (en) | 2015-06-01 | 2018-07-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11925102B2 (en) | 2015-06-04 | 2024-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10818853B2 (en) | 2015-06-04 | 2020-10-27 | University Of Southern California | Organic electroluminescent materials and devices |
| US10825997B2 (en) | 2015-06-25 | 2020-11-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10873036B2 (en) | 2015-07-07 | 2020-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9978956B2 (en) | 2015-07-15 | 2018-05-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10700284B2 (en) | 2015-07-20 | 2020-06-30 | Lg Chem, Ltd. | Photoactive composition |
| US11127905B2 (en) | 2015-07-29 | 2021-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11018309B2 (en) | 2015-08-03 | 2021-05-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11522140B2 (en) | 2015-08-17 | 2022-12-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10522769B2 (en) | 2015-08-18 | 2019-12-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10181564B2 (en) | 2015-08-26 | 2019-01-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10361381B2 (en) | 2015-09-03 | 2019-07-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11706972B2 (en) | 2015-09-08 | 2023-07-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11302872B2 (en) | 2015-09-09 | 2022-04-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10770664B2 (en) | 2015-09-21 | 2020-09-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20170092880A1 (en) | 2015-09-25 | 2017-03-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10847728B2 (en) | 2015-10-01 | 2020-11-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10593892B2 (en) | 2015-10-01 | 2020-03-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10991895B2 (en) | 2015-10-06 | 2021-04-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10177318B2 (en) | 2015-10-29 | 2019-01-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10388892B2 (en) | 2015-10-29 | 2019-08-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10388893B2 (en) | 2015-10-29 | 2019-08-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10998507B2 (en) | 2015-11-23 | 2021-05-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10476010B2 (en) | 2015-11-30 | 2019-11-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10957861B2 (en) | 2015-12-29 | 2021-03-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11024808B2 (en) | 2015-12-29 | 2021-06-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10135006B2 (en) | 2016-01-04 | 2018-11-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP6788314B2 (ja) | 2016-01-06 | 2020-11-25 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、表示装置及び照明装置 |
| US10707427B2 (en) | 2016-02-09 | 2020-07-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10457864B2 (en) | 2016-02-09 | 2019-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10600967B2 (en) | 2016-02-18 | 2020-03-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11094891B2 (en) | 2016-03-16 | 2021-08-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10276809B2 (en) | 2016-04-05 | 2019-04-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10236456B2 (en) | 2016-04-11 | 2019-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10566552B2 (en) | 2016-04-13 | 2020-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11081647B2 (en) | 2016-04-22 | 2021-08-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11228003B2 (en) | 2016-04-22 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11228002B2 (en) | 2016-04-22 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20170324049A1 (en) | 2016-05-05 | 2017-11-09 | Universal Display Corporation | Organic Electroluminescent Materials and Devices |
| US10985328B2 (en) | 2016-05-25 | 2021-04-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9966542B2 (en) | 2016-06-02 | 2018-05-08 | E I Du Pont De Nemours And Company | Electroactive materials |
| US10468609B2 (en) | 2016-06-02 | 2019-11-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| WO2017210072A1 (en) | 2016-06-03 | 2017-12-07 | E. I. Du Pont De Nemours And Company | Electroactive compounds |
| US10862054B2 (en) | 2016-06-20 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10672997B2 (en) | 2016-06-20 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11482683B2 (en) | 2016-06-20 | 2022-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10686140B2 (en) | 2016-06-20 | 2020-06-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10651403B2 (en) | 2016-06-20 | 2020-05-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10727423B2 (en) | 2016-06-20 | 2020-07-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10957866B2 (en) | 2016-06-30 | 2021-03-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9929360B2 (en) | 2016-07-08 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10566547B2 (en) | 2016-07-11 | 2020-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10153443B2 (en) | 2016-07-19 | 2018-12-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10720587B2 (en) | 2016-07-19 | 2020-07-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN109075255A (zh) | 2016-07-20 | 2018-12-21 | E.I.内穆尔杜邦公司 | 电活性材料 |
| US10205105B2 (en) | 2016-08-15 | 2019-02-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10608186B2 (en) | 2016-09-14 | 2020-03-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10505127B2 (en) | 2016-09-19 | 2019-12-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10680187B2 (en) | 2016-09-23 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11127906B2 (en) | 2016-10-03 | 2021-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11081658B2 (en) | 2016-10-03 | 2021-08-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11183642B2 (en) | 2016-10-03 | 2021-11-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11189804B2 (en) | 2016-10-03 | 2021-11-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11196010B2 (en) | 2016-10-03 | 2021-12-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11011709B2 (en) | 2016-10-07 | 2021-05-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11239432B2 (en) | 2016-10-14 | 2022-02-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10608185B2 (en) | 2016-10-17 | 2020-03-31 | Univeral Display Corporation | Organic electroluminescent materials and devices |
| US10236458B2 (en) | 2016-10-24 | 2019-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12317745B2 (en) | 2016-11-09 | 2025-05-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10340464B2 (en) | 2016-11-10 | 2019-07-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10680188B2 (en) | 2016-11-11 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10897016B2 (en) | 2016-11-14 | 2021-01-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10662196B2 (en) | 2016-11-17 | 2020-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10964893B2 (en) | 2016-11-17 | 2021-03-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10833276B2 (en) | 2016-11-21 | 2020-11-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10153445B2 (en) | 2016-11-21 | 2018-12-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR102259334B1 (ko) | 2016-11-23 | 2021-05-31 | 주식회사 엘지화학 | 전기활성 화합물 |
| US11555048B2 (en) | 2016-12-01 | 2023-01-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10490753B2 (en) | 2016-12-15 | 2019-11-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11545636B2 (en) | 2016-12-15 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11548905B2 (en) | 2016-12-15 | 2023-01-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10811618B2 (en) | 2016-12-19 | 2020-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11152579B2 (en) | 2016-12-28 | 2021-10-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20180190915A1 (en) | 2017-01-03 | 2018-07-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11201298B2 (en) | 2017-01-09 | 2021-12-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11780865B2 (en) | 2017-01-09 | 2023-10-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10804475B2 (en) | 2017-01-11 | 2020-10-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11545637B2 (en) | 2017-01-13 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10629820B2 (en) | 2017-01-18 | 2020-04-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10964904B2 (en) | 2017-01-20 | 2021-03-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11053268B2 (en) | 2017-01-20 | 2021-07-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11765968B2 (en) | 2017-01-23 | 2023-09-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11050028B2 (en) | 2017-01-24 | 2021-06-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12089486B2 (en) | 2017-02-08 | 2024-09-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10978647B2 (en) | 2017-02-15 | 2021-04-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10844084B2 (en) | 2017-02-22 | 2020-11-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10745431B2 (en) | 2017-03-08 | 2020-08-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10741780B2 (en) | 2017-03-10 | 2020-08-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10672998B2 (en) | 2017-03-23 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10910577B2 (en) | 2017-03-28 | 2021-02-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10873037B2 (en) | 2017-03-28 | 2020-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10844085B2 (en) | 2017-03-29 | 2020-11-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11158820B2 (en) | 2017-03-29 | 2021-10-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11056658B2 (en) | 2017-03-29 | 2021-07-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10862046B2 (en) | 2017-03-30 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11139443B2 (en) | 2017-03-31 | 2021-10-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11276829B2 (en) | 2017-03-31 | 2022-03-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11038117B2 (en) | 2017-04-11 | 2021-06-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10777754B2 (en) | 2017-04-11 | 2020-09-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10975113B2 (en) | 2017-04-21 | 2021-04-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11101434B2 (en) | 2017-04-21 | 2021-08-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11084838B2 (en) | 2017-04-21 | 2021-08-10 | Universal Display Corporation | Organic electroluminescent materials and device |
| US11038137B2 (en) | 2017-04-28 | 2021-06-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10910570B2 (en) | 2017-04-28 | 2021-02-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11117897B2 (en) | 2017-05-01 | 2021-09-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10941170B2 (en) | 2017-05-03 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11201299B2 (en) | 2017-05-04 | 2021-12-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10870668B2 (en) | 2017-05-05 | 2020-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10862055B2 (en) | 2017-05-05 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10930864B2 (en) | 2017-05-10 | 2021-02-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10822362B2 (en) | 2017-05-11 | 2020-11-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10944060B2 (en) | 2017-05-11 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11038115B2 (en) | 2017-05-18 | 2021-06-15 | Universal Display Corporation | Organic electroluminescent materials and device |
| US10934293B2 (en) | 2017-05-18 | 2021-03-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10790455B2 (en) | 2017-05-18 | 2020-09-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10840459B2 (en) | 2017-05-18 | 2020-11-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10944062B2 (en) | 2017-05-18 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10930862B2 (en) | 2017-06-01 | 2021-02-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11832510B2 (en) | 2017-06-23 | 2023-11-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11608321B2 (en) | 2017-06-23 | 2023-03-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11725022B2 (en) | 2017-06-23 | 2023-08-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11758804B2 (en) | 2017-06-23 | 2023-09-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12098157B2 (en) | 2017-06-23 | 2024-09-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11174259B2 (en) | 2017-06-23 | 2021-11-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11802136B2 (en) | 2017-06-23 | 2023-10-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11678565B2 (en) | 2017-06-23 | 2023-06-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11495757B2 (en) | 2017-06-23 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11552261B2 (en) | 2017-06-23 | 2023-01-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11814403B2 (en) | 2017-06-23 | 2023-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10968226B2 (en) | 2017-06-23 | 2021-04-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11469382B2 (en) | 2017-07-12 | 2022-10-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11322691B2 (en) | 2017-07-26 | 2022-05-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11765970B2 (en) | 2017-07-26 | 2023-09-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11968883B2 (en) | 2017-07-26 | 2024-04-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11228010B2 (en) | 2017-07-26 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11239433B2 (en) | 2017-07-26 | 2022-02-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11917843B2 (en) | 2017-07-26 | 2024-02-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11744141B2 (en) | 2017-08-09 | 2023-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11910699B2 (en) | 2017-08-10 | 2024-02-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11349083B2 (en) | 2017-08-10 | 2022-05-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11508913B2 (en) | 2017-08-10 | 2022-11-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11744142B2 (en) | 2017-08-10 | 2023-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11723269B2 (en) | 2017-08-22 | 2023-08-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11462697B2 (en) | 2017-08-22 | 2022-10-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11437591B2 (en) | 2017-08-24 | 2022-09-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11605791B2 (en) | 2017-09-01 | 2023-03-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11696492B2 (en) | 2017-09-07 | 2023-07-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11444249B2 (en) | 2017-09-07 | 2022-09-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11424420B2 (en) | 2017-09-07 | 2022-08-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10608188B2 (en) | 2017-09-11 | 2020-03-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11778897B2 (en) | 2017-09-20 | 2023-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12389791B2 (en) | 2017-09-21 | 2025-08-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12459946B2 (en) | 2017-10-05 | 2025-11-04 | Universal Display Corporation | Organic host materials for electroluminescent devices |
| US11910702B2 (en) | 2017-11-07 | 2024-02-20 | Universal Display Corporation | Organic electroluminescent devices |
| US11214587B2 (en) | 2017-11-07 | 2022-01-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11183646B2 (en) | 2017-11-07 | 2021-11-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11168103B2 (en) | 2017-11-17 | 2021-11-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11825735B2 (en) | 2017-11-28 | 2023-11-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11937503B2 (en) | 2017-11-30 | 2024-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11233204B2 (en) | 2017-12-14 | 2022-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12075690B2 (en) | 2017-12-14 | 2024-08-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11233205B2 (en) | 2017-12-14 | 2022-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10971687B2 (en) | 2017-12-14 | 2021-04-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11700765B2 (en) | 2018-01-10 | 2023-07-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11081659B2 (en) | 2018-01-10 | 2021-08-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11271177B2 (en) | 2018-01-11 | 2022-03-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11515493B2 (en) | 2018-01-11 | 2022-11-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11367840B2 (en) | 2018-01-26 | 2022-06-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11845764B2 (en) | 2018-01-26 | 2023-12-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11542289B2 (en) | 2018-01-26 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12029055B2 (en) | 2018-01-30 | 2024-07-02 | The University Of Southern California | OLED with hybrid emissive layer |
| US11342509B2 (en) | 2018-02-09 | 2022-05-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11180519B2 (en) | 2018-02-09 | 2021-11-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11957050B2 (en) | 2018-02-09 | 2024-04-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11239434B2 (en) | 2018-02-09 | 2022-02-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11165028B2 (en) | 2018-03-12 | 2021-11-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11217757B2 (en) | 2018-03-12 | 2022-01-04 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11279722B2 (en) | 2018-03-12 | 2022-03-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11557733B2 (en) | 2018-03-12 | 2023-01-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11142538B2 (en) | 2018-03-12 | 2021-10-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11882759B2 (en) | 2018-04-13 | 2024-01-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11390639B2 (en) | 2018-04-13 | 2022-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11616203B2 (en) | 2018-04-17 | 2023-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11515494B2 (en) | 2018-05-04 | 2022-11-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11342513B2 (en) | 2018-05-04 | 2022-05-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11753427B2 (en) | 2018-05-04 | 2023-09-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11793073B2 (en) | 2018-05-06 | 2023-10-17 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11459349B2 (en) | 2018-05-25 | 2022-10-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11450822B2 (en) | 2018-05-25 | 2022-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11716900B2 (en) | 2018-05-30 | 2023-08-01 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11296283B2 (en) | 2018-06-04 | 2022-04-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11925103B2 (en) | 2018-06-05 | 2024-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11339182B2 (en) | 2018-06-07 | 2022-05-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11228004B2 (en) | 2018-06-22 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11261207B2 (en) | 2018-06-25 | 2022-03-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11753425B2 (en) | 2018-07-11 | 2023-09-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12378197B2 (en) | 2018-07-13 | 2025-08-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12453279B2 (en) | 2018-08-22 | 2025-10-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11233203B2 (en) | 2018-09-06 | 2022-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12171137B2 (en) | 2018-09-10 | 2024-12-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11485706B2 (en) | 2018-09-11 | 2022-11-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11718634B2 (en) | 2018-09-14 | 2023-08-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11903305B2 (en) | 2018-09-24 | 2024-02-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11495752B2 (en) | 2018-10-08 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11469383B2 (en) | 2018-10-08 | 2022-10-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11476430B2 (en) | 2018-10-15 | 2022-10-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11515482B2 (en) | 2018-10-23 | 2022-11-29 | Universal Display Corporation | Deep HOMO (highest occupied molecular orbital) emitter device structures |
| US11469384B2 (en) | 2018-11-02 | 2022-10-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11825736B2 (en) | 2018-11-19 | 2023-11-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11963441B2 (en) | 2018-11-26 | 2024-04-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11889708B2 (en) | 2019-11-14 | 2024-01-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11716899B2 (en) | 2018-11-28 | 2023-08-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11672165B2 (en) | 2018-11-28 | 2023-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11706980B2 (en) | 2018-11-28 | 2023-07-18 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11672176B2 (en) | 2018-11-28 | 2023-06-06 | Universal Display Corporation | Host materials for electroluminescent devices |
| US11690285B2 (en) | 2018-11-28 | 2023-06-27 | Universal Display Corporation | Electroluminescent devices |
| CN109585830B (zh) * | 2018-12-03 | 2020-11-24 | 江苏理工学院 | 包覆导电聚合物和氧化石墨烯的硫硒化合物及其制备和应用 |
| US11623936B2 (en) | 2018-12-11 | 2023-04-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12281129B2 (en) | 2018-12-12 | 2025-04-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11737349B2 (en) | 2018-12-12 | 2023-08-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11834459B2 (en) | 2018-12-12 | 2023-12-05 | Universal Display Corporation | Host materials for electroluminescent devices |
| US12167673B2 (en) | 2018-12-19 | 2024-12-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11780829B2 (en) | 2019-01-30 | 2023-10-10 | The University Of Southern California | Organic electroluminescent materials and devices |
| US11812624B2 (en) | 2019-01-30 | 2023-11-07 | The University Of Southern California | Organic electroluminescent materials and devices |
| US12477890B2 (en) | 2019-02-01 | 2025-11-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11370809B2 (en) | 2019-02-08 | 2022-06-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12137605B2 (en) | 2019-02-08 | 2024-11-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11325932B2 (en) | 2019-02-08 | 2022-05-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11773320B2 (en) | 2019-02-21 | 2023-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12250872B2 (en) | 2019-02-22 | 2025-03-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11871653B2 (en) | 2019-02-22 | 2024-01-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11758807B2 (en) | 2019-02-22 | 2023-09-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11512093B2 (en) | 2019-03-04 | 2022-11-29 | Universal Display Corporation | Compound used for organic light emitting device (OLED), consumer product and formulation |
| US11739081B2 (en) | 2019-03-11 | 2023-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11569480B2 (en) | 2019-03-12 | 2023-01-31 | Universal Display Corporation | Plasmonic OLEDs and vertical dipole emitters |
| US11637261B2 (en) | 2019-03-12 | 2023-04-25 | Universal Display Corporation | Nanopatch antenna outcoupling structure for use in OLEDs |
| US11963438B2 (en) | 2019-03-26 | 2024-04-16 | The University Of Southern California | Organic electroluminescent materials and devices |
| US12122793B2 (en) | 2019-03-27 | 2024-10-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12240865B2 (en) | 2019-03-27 | 2025-03-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11639363B2 (en) | 2019-04-22 | 2023-05-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12075691B2 (en) | 2019-04-30 | 2024-08-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11613550B2 (en) | 2019-04-30 | 2023-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices comprising benzimidazole-containing metal complexes |
| US11495756B2 (en) | 2019-05-07 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12103942B2 (en) | 2019-05-13 | 2024-10-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11827651B2 (en) | 2019-05-13 | 2023-11-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11634445B2 (en) | 2019-05-21 | 2023-04-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12010859B2 (en) | 2019-05-24 | 2024-06-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11647667B2 (en) | 2019-06-14 | 2023-05-09 | Universal Display Corporation | Organic electroluminescent compounds and organic light emitting devices using the same |
| US12077550B2 (en) | 2019-07-02 | 2024-09-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11920070B2 (en) | 2019-07-12 | 2024-03-05 | The University Of Southern California | Luminescent janus-type, two-coordinated metal complexes |
| US11685754B2 (en) | 2019-07-22 | 2023-06-27 | Universal Display Corporation | Heteroleptic organic electroluminescent materials |
| US11926638B2 (en) | 2019-07-22 | 2024-03-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12281128B2 (en) | 2019-07-30 | 2025-04-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11708355B2 (en) | 2019-08-01 | 2023-07-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12295251B2 (en) | 2019-08-01 | 2025-05-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11985888B2 (en) | 2019-08-12 | 2024-05-14 | The Regents Of The University Of Michigan | Organic electroluminescent device |
| US11374181B2 (en) | 2019-08-14 | 2022-06-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12227525B2 (en) | 2019-08-14 | 2025-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11930699B2 (en) | 2019-08-15 | 2024-03-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12139501B2 (en) | 2019-08-16 | 2024-11-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12234249B2 (en) | 2019-08-21 | 2025-02-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11925105B2 (en) | 2019-08-26 | 2024-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11937494B2 (en) | 2019-08-28 | 2024-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11600787B2 (en) | 2019-08-30 | 2023-03-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN112457349B (zh) | 2019-09-06 | 2024-10-15 | 环球展览公司 | 有机电致发光材料和装置 |
| US11820783B2 (en) | 2019-09-06 | 2023-11-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12144244B2 (en) | 2019-09-10 | 2024-11-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12331065B2 (en) | 2019-09-26 | 2025-06-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11999886B2 (en) | 2019-09-26 | 2024-06-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12486296B2 (en) | 2019-10-02 | 2025-12-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11864458B2 (en) | 2019-10-08 | 2024-01-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP6881541B2 (ja) * | 2019-10-09 | 2021-06-02 | ダイキン工業株式会社 | 含フッ素ポリマーを含有する組成物および架橋物 |
| US11950493B2 (en) | 2019-10-15 | 2024-04-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11697653B2 (en) | 2019-10-21 | 2023-07-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11919914B2 (en) | 2019-10-25 | 2024-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN120463729A (zh) | 2019-10-25 | 2025-08-12 | 环球展览公司 | 有机电致发光材料和装置 |
| US11765965B2 (en) | 2019-10-30 | 2023-09-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12201013B2 (en) | 2020-01-08 | 2025-01-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12187751B2 (en) | 2020-01-08 | 2025-01-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11778895B2 (en) | 2020-01-13 | 2023-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12426495B2 (en) | 2020-01-28 | 2025-09-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11917900B2 (en) | 2020-01-28 | 2024-02-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11932660B2 (en) | 2020-01-29 | 2024-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12245502B2 (en) | 2020-02-03 | 2025-03-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12156463B2 (en) | 2020-02-07 | 2024-11-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12084465B2 (en) | 2020-02-24 | 2024-09-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12324348B2 (en) | 2020-02-28 | 2025-06-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12234251B2 (en) | 2020-03-04 | 2025-02-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12018035B2 (en) | 2020-03-23 | 2024-06-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12129269B2 (en) | 2020-04-13 | 2024-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12279520B2 (en) | 2020-04-22 | 2025-04-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11970508B2 (en) | 2020-04-22 | 2024-04-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12466844B2 (en) | 2020-05-13 | 2025-11-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12286410B2 (en) | 2020-05-18 | 2025-04-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12035613B2 (en) | 2020-05-26 | 2024-07-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12275747B2 (en) | 2020-06-02 | 2025-04-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12247043B2 (en) | 2020-06-11 | 2025-03-11 | Universal Display Corporation | Organic electroluminescent material and formulations, and its various uses as hosts, fluorescent dopants, and acceptors in organic light emitting diodes |
| US12279516B2 (en) | 2020-06-17 | 2025-04-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12419188B2 (en) | 2020-06-30 | 2025-09-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12336427B2 (en) | 2020-07-09 | 2025-06-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12157748B2 (en) | 2020-07-30 | 2024-12-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12369487B2 (en) | 2020-08-05 | 2025-07-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12065451B2 (en) | 2020-08-19 | 2024-08-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12289986B2 (en) | 2020-08-25 | 2025-04-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12369488B2 (en) | 2020-09-09 | 2025-07-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12486295B2 (en) | 2020-09-14 | 2025-12-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12221455B2 (en) | 2020-09-24 | 2025-02-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12252499B2 (en) | 2020-09-29 | 2025-03-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12460128B2 (en) | 2020-10-02 | 2025-11-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12486451B2 (en) | 2020-10-02 | 2025-12-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12435102B2 (en) | 2020-10-02 | 2025-10-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12286447B2 (en) | 2020-10-06 | 2025-04-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12312365B2 (en) | 2020-10-12 | 2025-05-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12486288B2 (en) | 2020-10-12 | 2025-12-02 | University Of Southern California | Fast phosphors utilizing HP2H ligands |
| US12137606B2 (en) | 2020-10-20 | 2024-11-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12245504B2 (en) | 2020-10-26 | 2025-03-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12247042B2 (en) | 2020-10-26 | 2025-03-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12262631B2 (en) | 2020-11-10 | 2025-03-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12325717B2 (en) | 2020-11-24 | 2025-06-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12331064B2 (en) | 2020-12-09 | 2025-06-17 | University Of Southern California | Tandem carbene phosphors |
| US12342716B2 (en) | 2020-12-09 | 2025-06-24 | University Of Southern California | Tandem-carbene phosphors |
| US12466848B2 (en) | 2020-12-10 | 2025-11-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12398164B2 (en) | 2021-02-01 | 2025-08-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12459966B2 (en) | 2021-02-02 | 2025-11-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12484437B2 (en) | 2021-02-26 | 2025-11-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12421262B2 (en) | 2021-03-15 | 2025-09-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12473317B2 (en) | 2021-06-04 | 2025-11-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12495715B2 (en) | 2021-06-29 | 2025-12-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12414433B2 (en) | 2022-02-11 | 2025-09-09 | Universal Display Corporation | Organic electroluminescent devices |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7317047B2 (en) * | 2002-09-24 | 2008-01-08 | E.I. Du Pont De Nemours And Company | Electrically conducting organic polymer/nanoparticle composites and methods for use thereof |
| US7390438B2 (en) * | 2003-04-22 | 2008-06-24 | E.I. Du Pont De Nemours And Company | Water dispersible substituted polydioxythiophenes made with fluorinated polymeric sulfonic acid colloids |
| US7351358B2 (en) * | 2004-03-17 | 2008-04-01 | E.I. Du Pont De Nemours And Company | Water dispersible polypyrroles made with polymeric acid colloids for electronics applications |
-
2008
- 2008-07-22 KR KR1020107004335A patent/KR20100065302A/ko not_active Withdrawn
- 2008-07-22 WO PCT/US2008/070718 patent/WO2009018009A1/en not_active Ceased
- 2008-07-22 EP EP08796400A patent/EP2173811A1/en not_active Withdrawn
- 2008-07-22 CN CN200880023383A patent/CN101688052A/zh active Pending
- 2008-07-22 JP JP2010518326A patent/JP2010534739A/ja active Pending
- 2008-07-23 TW TW097127994A patent/TW200915350A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010534739A (ja) | 2010-11-11 |
| CN101688052A (zh) | 2010-03-31 |
| EP2173811A1 (en) | 2010-04-14 |
| KR20100065302A (ko) | 2010-06-16 |
| WO2009018009A1 (en) | 2009-02-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW200915350A (en) | Aqueous dispersions of electrically conducting polymers containing inorganic nanoparticles | |
| JP5324217B2 (ja) | 導電性ポリマー組成物 | |
| US8658061B2 (en) | Electrically conductive polymer compositions | |
| JP5061184B2 (ja) | 有機発光ダイオードの形成方法、およびその方法によって製造されたデバイス | |
| CN102349115B (zh) | 用于涂层应用的导电聚合物组合物 | |
| TW201005020A (en) | Aqueous dispersions of electrically conducting polymers containing inorganic nanoparticles | |
| JP2008546898A (ja) | 導電性ポリマー組成物 | |
| US8461758B2 (en) | Buffer bilayers for electronic devices | |
| TW200850050A (en) | Process for making an organic electronic device | |
| TW200944374A (en) | Buffer bilayers for electronic devices | |
| TW201100482A (en) | Electrically conductive polymer compositions and films made therefrom | |
| JP2009534831A (ja) | 高エネルギーポテンシャル二重層組成物 | |
| TW201127895A (en) | Electrically conductive polymer compositions | |
| KR101517651B1 (ko) | 전기 전도성 중합체 조성물 | |
| TW200901229A (en) | Compositions of electrically conducting polymers made with ultra-pure fully-fluorinated acid polymers | |
| TW201100481A (en) | Electrically conductive polymer compositions and films made therefrom | |
| CN102239190B (zh) | 导电聚合物组合物 | |
| KR102290839B1 (ko) | 도전성 중합체 조성물에서의 디헤테로 아민 | |
| US8216685B2 (en) | Buffer bilayers for electronic devices |