JP2008135498A - Light emitting element - Google Patents
Light emitting element Download PDFInfo
- Publication number
- JP2008135498A JP2008135498A JP2006319658A JP2006319658A JP2008135498A JP 2008135498 A JP2008135498 A JP 2008135498A JP 2006319658 A JP2006319658 A JP 2006319658A JP 2006319658 A JP2006319658 A JP 2006319658A JP 2008135498 A JP2008135498 A JP 2008135498A
- Authority
- JP
- Japan
- Prior art keywords
- group
- derivatives
- light emitting
- light
- ring
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000463 material Substances 0.000 claims abstract description 111
- 239000002019 doping agent Substances 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims abstract description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000005013 aryl ether group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 150000004832 aryl thioethers Chemical group 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 46
- 230000032258 transport Effects 0.000 description 27
- 238000000034 method Methods 0.000 description 19
- 239000000758 substrate Substances 0.000 description 16
- 229910052741 iridium Inorganic materials 0.000 description 12
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- -1 diamine compound Chemical class 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- 239000011159 matrix material Substances 0.000 description 8
- 125000005595 acetylacetonate group Chemical group 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 238000010894 electron beam technology Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 150000004866 oxadiazoles Chemical class 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 238000004544 sputter deposition Methods 0.000 description 4
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 4
- KXMKGOPUYUWQHC-UHFFFAOYSA-N 2-[3-(1,10-phenanthrolin-2-yl)phenyl]-1,10-phenanthroline Chemical compound C1=CN=C2C3=NC(C=4C=CC=C(C=4)C=4N=C5C6=NC=CC=C6C=CC5=CC=4)=CC=C3C=CC2=C1 KXMKGOPUYUWQHC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910052693 Europium Inorganic materials 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920000123 polythiophene Polymers 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 150000003248 quinolines Chemical class 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- CDVPABAGURXNBJ-UHFFFAOYSA-N S1C(=CC=C1)C1=NC=CC=C1[Ir] Chemical compound S1C(=CC=C1)C1=NC=CC=C1[Ir] CDVPABAGURXNBJ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical group C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 150000005054 naphthyridines Chemical class 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 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
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical class C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 2
- 150000005041 phenanthrolines Chemical class 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229920002098 polyfluorene Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 150000003219 pyrazolines Chemical class 0.000 description 2
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 2
- 150000005255 pyrrolopyridines Chemical class 0.000 description 2
- 150000003252 quinoxalines Chemical class 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- MDYOLVRUBBJPFM-UHFFFAOYSA-N tropolone Chemical compound OC1=CC=CC=CC1=O MDYOLVRUBBJPFM-UHFFFAOYSA-N 0.000 description 2
- 229910021642 ultra pure water Inorganic materials 0.000 description 2
- 239000012498 ultrapure water Substances 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical class C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical group C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- UIWLITBBFICQKW-UHFFFAOYSA-N 1h-benzo[h]quinolin-2-one Chemical class C1=CC=C2C3=NC(O)=CC=C3C=CC2=C1 UIWLITBBFICQKW-UHFFFAOYSA-N 0.000 description 1
- WLODWTPNUWYZKN-UHFFFAOYSA-N 1h-pyrrol-2-ol Chemical class OC1=CC=CN1 WLODWTPNUWYZKN-UHFFFAOYSA-N 0.000 description 1
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- MKFFVKXHQDCENQ-UHFFFAOYSA-N 2-(1-benzo[h]quinolin-2-yl-9,9'-spirobi[fluorene]-2-yl)benzo[h]quinoline Chemical compound N1=C(C=CC2=CC=C3C(=C12)C=CC=C3)C1=C(C=2C3(C4=CC=CC=C4C=2C=C1)C1=CC=CC=C1C=1C=CC=CC=13)C1=NC2=C3C(=CC=C2C=C1)C=CC=C3 MKFFVKXHQDCENQ-UHFFFAOYSA-N 0.000 description 1
- MTQADTZTLQGIRT-UHFFFAOYSA-N 2-(4-dinaphthalen-1-ylphosphorylphenyl)-1,8-naphthyridine Chemical compound C1=CC=C2C(P(C=3C=CC(=CC=3)C=3N=C4N=CC=CC4=CC=3)(C=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 MTQADTZTLQGIRT-UHFFFAOYSA-N 0.000 description 1
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical group C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 1
- QWKWMRMSNXMFOE-UHFFFAOYSA-N 2-[2,3-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1C1=NC2=CC=CC=C2N1C1=CC=CC=C1 QWKWMRMSNXMFOE-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-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
- XBHOUXSGHYZCNH-UHFFFAOYSA-N 2-phenyl-1,3-benzothiazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2S1 XBHOUXSGHYZCNH-UHFFFAOYSA-N 0.000 description 1
- FIISKTXZUZBTRC-UHFFFAOYSA-N 2-phenyl-1,3-benzoxazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2O1 FIISKTXZUZBTRC-UHFFFAOYSA-N 0.000 description 1
- KYGSXEYUWRFVNY-UHFFFAOYSA-N 2-pyran-2-ylidenepropanedinitrile Chemical class N#CC(C#N)=C1OC=CC=C1 KYGSXEYUWRFVNY-UHFFFAOYSA-N 0.000 description 1
- GOINCKIOWXDBEH-UHFFFAOYSA-N 3,3-diacetylpentane-2,4-dione;terbium Chemical compound [Tb].CC(=O)C(C(C)=O)(C(C)=O)C(C)=O GOINCKIOWXDBEH-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical group CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
- AOQKGYRILLEVJV-UHFFFAOYSA-N 4-naphthalen-1-yl-3,5-diphenyl-1,2,4-triazole Chemical compound C1=CC=CC=C1C(N1C=2C3=CC=CC=C3C=CC=2)=NN=C1C1=CC=CC=C1 AOQKGYRILLEVJV-UHFFFAOYSA-N 0.000 description 1
- GHBQLFWTMLRYKN-UHFFFAOYSA-N 9-prop-2-enylcarbazole Chemical compound C1=CC=C2N(CC=C)C3=CC=CC=C3C2=C1 GHBQLFWTMLRYKN-UHFFFAOYSA-N 0.000 description 1
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
- NZGXEUWGGSDALJ-UHFFFAOYSA-N C1=CC=CC=C1C1=NC=CC=C1[Ir](C=1C(=NC=CC=1)C=1C=CC=CC=1)C1=CC=CN=C1C1=CC=CC=C1 Chemical compound C1=CC=CC=C1C1=NC=CC=C1[Ir](C=1C(=NC=CC=1)C=1C=CC=CC=1)C1=CC=CN=C1C1=CC=CC=C1 NZGXEUWGGSDALJ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical group OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- LSMNEJCTMKWDIH-UHFFFAOYSA-N S1C(=CC2=C1C=CC=C2)C2=NC=CC=C2[Ir] Chemical compound S1C(=CC2=C1C=CC=C2)C2=NC=CC=C2[Ir] LSMNEJCTMKWDIH-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DWFQLHGORQRJLK-UHFFFAOYSA-N [Pt].CCc1c2ccc(n2)c(CC)c2ccc([nH]2)c(CC)c2ccc(n2)c(CC)c2ccc1[nH]2 Chemical compound [Pt].CCc1c2ccc(n2)c(CC)c2ccc([nH]2)c(CC)c2ccc(n2)c(CC)c2ccc1[nH]2 DWFQLHGORQRJLK-UHFFFAOYSA-N 0.000 description 1
- 150000001251 acridines Chemical class 0.000 description 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 229940027998 antiseptic and disinfectant acridine derivative Drugs 0.000 description 1
- 150000007980 azole derivatives Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- OMZSGWSJDCOLKM-UHFFFAOYSA-N copper(II) sulfide Chemical compound [S-2].[Cu+2] OMZSGWSJDCOLKM-UHFFFAOYSA-N 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 150000001893 coumarin derivatives Chemical class 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000007946 flavonol Chemical class 0.000 description 1
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 1
- 235000011957 flavonols Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- WNMLJURZPRTHTK-UHFFFAOYSA-N iridium 2-phenyl-1,3-benzothiazole Chemical compound [Ir].C1=CC=CC=C1C1=NC2=CC=CC=C2S1.C1=CC=CC=C1C1=NC2=CC=CC=C2S1.C1=CC=CC=C1C1=NC2=CC=CC=C2S1 WNMLJURZPRTHTK-UHFFFAOYSA-N 0.000 description 1
- WEODYYMMVGCMIB-UHFFFAOYSA-N iridium 2-phenyl-1,3-benzoxazole Chemical compound [Ir].C1=CC=CC=C1C1=NC2=CC=CC=C2O1.C1=CC=CC=C1C1=NC2=CC=CC=C2O1.C1=CC=CC=C1C1=NC2=CC=CC=C2O1 WEODYYMMVGCMIB-UHFFFAOYSA-N 0.000 description 1
- 229910000833 kovar Inorganic materials 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 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
- 239000000178 monomer Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 150000002988 phenazines Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical class [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical group N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 150000004322 quinolinols Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical class [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- YKSGNOMLAIJTLT-UHFFFAOYSA-N violanthrone Chemical class C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=CC=C3C3=CC=C4C1=C32 YKSGNOMLAIJTLT-UHFFFAOYSA-N 0.000 description 1
- 238000001039 wet etching Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
- Indole Compounds (AREA)
Abstract
Description
本発明は、電気エネルギーを光に変換できる素子であって、表示素子、フラットパネルディスプレイ、バックライト、照明、インテリア、標識、看板、電子写真機、光信号発生器などの分野に利用可能な発光素子に関する。 The present invention is an element that can convert electrical energy into light, and can be used in the fields of display elements, flat panel displays, backlights, lighting, interiors, signs, signboards, electrophotographic machines, optical signal generators, and the like. It relates to an element.
陰極から注入された電子と陽極から注入された正孔が両極に挟まれた有機発光体内で再結合する際に発光するという有機薄膜発光素子の研究が、近年活発に行われている。この発光素子は、薄型でかつ低駆動電圧下での高輝度発光と、発光材料を選ぶことによる多色発光が特徴であり、注目を集めている。 In recent years, research on organic thin-film light-emitting devices that emit light when electrons injected from a cathode and holes injected from an anode are recombined in an organic light-emitting body sandwiched between both electrodes has been actively conducted. This light-emitting element is characterized by thin light emission with high luminance under a low driving voltage and multicolor light emission by selecting a light-emitting material.
この研究は、コダック社のＣ．Ｗ．Ｔａｎｇらによって有機薄膜発光素子が高輝度に発光することが示されて以来、多くの研究機関が検討を行っている。コダック社の研究グループが提示した有機薄膜発光素子の代表的な構成は、ＩＴＯガラス基板上に正孔輸送性のジアミン化合物、発光層であるトリス（８−キノリノラート）アルミニウム（III）、そして陰極としてＭｇ：Ａｇを順次設けたものであり、１０Ｖ程度の駆動電圧で１,０００ｃｄ／ｍ２の緑色発光が可能であった（非特許文献１参照）。 This study was conducted by C.D. W. Since Tang et al. Have shown that organic thin-film light-emitting elements emit light with high brightness, many research institutions have studied. The representative structure of the organic thin film light emitting device presented by the Kodak research group is a hole transporting diamine compound on an ITO glass substrate, tris (8-quinolinolato) aluminum (III) as a light emitting layer, and a cathode. Mg: Ag was sequentially provided, and green light emission of 1,000 cd / m 2 was possible with a driving voltage of about 10 V (see Non-Patent Document 1).
また、有機薄膜発光素子は、発光層に種々の発光材料を用いることにより、多様な発光色を得ることが可能であることから、ディスプレイなどへの実用化研究が盛んである。特に赤色、緑色、青色の三原色の発光材料の研究が最も活発であり、特性向上を目指して鋭意研究がなされている。 In addition, organic thin-film light-emitting elements can be obtained in various light-emitting colors by using various light-emitting materials for the light-emitting layer. In particular, research on light emitting materials of the three primary colors of red, green, and blue is the most active, and intensive research has been conducted with the aim of improving characteristics.
有機薄膜発光素子における最大の課題の一つは、高発光効率と低駆動電圧の両立である。高効率な発光素子を得る手段としては、ホスト材料にドーパント材料を数％ドーピングすることにより発光層を形成する方法が知られている（特許文献１参照）。ホスト材料には高いキャリア移動度、均一な成膜性などが要求され、ドーパント材料には高い蛍光量子収率、均一な分散性などが要求される。 One of the biggest problems in organic thin-film light-emitting elements is the compatibility between high luminous efficiency and low driving voltage. As a means for obtaining a highly efficient light-emitting element, a method of forming a light-emitting layer by doping a host material with a dopant material of several percent is known (see Patent Document 1). The host material is required to have high carrier mobility and uniform film formability, and the dopant material is required to have high fluorescence quantum yield and uniform dispersibility.
また、ドーパント材料としては、従来から一般的には蛍光性（一重項発光）材料が用いられているが、発光効率を向上させるために、燐光性（三重項発光）材料を用いることが以前より試みられており、プリンストン大学のグループが、従来の蛍光性材料に比べて発光効率が大幅に上回ることを示している（非特許文献２参照）。燐光性ドーパント材料としては、イリジウム、オスミウム、ロジウム、パラジウム、白金等を中心金属とする金属錯体を用いる技術が開示されている（特許文献２〜４参照）。また、燐光性ドーパント材料と組み合わせるホスト材料としては、カルバゾール誘導体、芳香族アミン誘導体、キノリノール金属錯体等を用いる技術が開示されている（特許文献２〜６参照）が、いずれも充分な発光効率と低駆動電圧を示すものは無かった。 In addition, as a dopant material, a fluorescent (singlet light emission) material is generally used in the past, but a phosphorescent (triplet light emission) material has been used in order to improve the light emission efficiency. Attempts have been made and a group at Princeton University has shown that the luminous efficiency is significantly higher than conventional fluorescent materials (see Non-Patent Document 2). As a phosphorescent dopant material, a technique using a metal complex having iridium, osmium, rhodium, palladium, platinum or the like as a central metal is disclosed (see Patent Documents 2 to 4). Moreover, as a host material combined with a phosphorescent dopant material, a technique using a carbazole derivative, an aromatic amine derivative, a quinolinol metal complex, or the like has been disclosed (see Patent Documents 2 to 6). None showed a low drive voltage.
上記に限らず、発光材料を形成するホスト材料、ドーパント材料はそれぞれ数多くあり、これらを組み合わせるとその数は膨大になる。また一般的にはホスト材料から燐光性ドーパント材料へのエネルギー移動のし易さの指針としては、ホスト材料とドーパント材料の三重項準位の関係が知られているが（特許文献２参照）、全ての発光メカニズムが解明されているものでは無く、試行錯誤的な部分が多い。すなわち、より良好な発光特性を有する発光素子を得るためには、新規なホスト材料、ドーパント材料の発見だけではなく、最適なホスト材料とドーパント材料の組み合わせを発見することが重要になる。
そこで本発明は、かかる従来技術の問題を解決し、高発光効率かつ低駆動電圧の発光素子を提供するものである。 Accordingly, the present invention solves the problems of the prior art and provides a light emitting element with high luminous efficiency and low driving voltage.
すなわち本発明は、陽極と陰極の間に、少なくともホスト材料とドーパント材料からなる発光層が存在し、電気エネルギーにより発光する素子であって、ホスト材料が一般式（１）で表されるカルバゾール骨格を有する化合物であり、ドーパント材料が三重項発光材料であることを特徴とする発光素子である。 That is, the present invention is an element in which a light emitting layer composed of at least a host material and a dopant material exists between an anode and a cathode and emits light by electric energy, and the host material is a carbazole skeleton represented by the general formula (1). A light-emitting element characterized in that the dopant material is a triplet light-emitting material.
（Ｒ１〜Ｒ２４はそれぞれ、水素、アルキル基、シクロアルキル基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、アミノ基、シリル基、あるいは隣接する置換基との間の環構造の中から選ばれる。但し、Ｒ１５〜Ｒ２４の少なくとも一つはアミノ基、隣接する置換基との環構造より選ばれる。） (R 1 to R 24 are each hydrogen, an alkyl group, a cycloalkyl group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, an aryl group, an amino group, a silyl group, or an adjacent substituent. (It is selected from ring structures, provided that at least one of R 15 to R 24 is selected from an amino group and a ring structure with an adjacent substituent.)
本発明の発光素子は、発光効率が高く、かつ低駆動電圧で駆動できるものである。 The light emitting device of the present invention has high luminous efficiency and can be driven with a low driving voltage.
本発明の発光素子は、少なくとも陽極と陰極、およびそれら陽極と陰極の間に介在する発光素子材料からなる有機層とで構成されている。 The light emitting device of the present invention comprises at least an anode and a cathode, and an organic layer made of a light emitting device material interposed between the anode and the cathode.
本発明で用いられる陽極は、正孔を有機層に効率よく注入できる材料であれば特に限定されないが、比較的仕事関数の大きい材料を用いるのが好ましく、例えば、酸化錫、酸化インジウム、酸化亜鉛インジウム、酸化錫インジウム（ＩＴＯ）などの導電性金属酸化物、あるいは金、銀、クロムなどの金属、ヨウ化銅、硫化銅などの無機導電性物質、ポリチオフェン、ポリピロールおよびポリアニリンなどの導電性ポリマーなどが挙げられる。これらの電極材料は、単独で用いてもよいが、複数の材料を積層または混合して用いてもよい。 The anode used in the present invention is not particularly limited as long as it can efficiently inject holes into the organic layer, but it is preferable to use a material having a relatively large work function. For example, tin oxide, indium oxide, zinc oxide Conductive metal oxides such as indium and indium tin oxide (ITO), metals such as gold, silver and chromium, inorganic conductive materials such as copper iodide and copper sulfide, conductive polymers such as polythiophene, polypyrrole and polyaniline, etc. Is mentioned. These electrode materials may be used alone, or a plurality of materials may be laminated or mixed.
電極の抵抗は、発光素子の発光に十分な電流が供給できればよく、発光素子の消費電力の観点からは低抵抗であることが望ましい。例えば、３００Ω／□以下のＩＴＯ基板であれば素子電極として機能するが、現在では１０Ω／□程度の基板の供給も可能になっていることから、１００Ω／□以下の低抵抗品を使用することが特に望ましい。ＩＴＯの厚みは抵抗値に合わせて任意に選ぶ事ができるが、通常１００〜３００ｎｍの間で用いられることが多い。 The resistance of the electrode is not limited as long as a current sufficient for light emission of the light-emitting element can be supplied. For example, an ITO substrate of 300Ω / □ or less functions as an element electrode, but since it is now possible to supply a substrate of about 10Ω / □, use a low-resistance product of 100Ω / □ or less. Is particularly desirable. The thickness of ITO can be arbitrarily selected according to the resistance value, but is usually used in a range of 100 to 300 nm.
また、発光素子の機械的強度を保つために、発光素子を基板上に形成することが好ましい。基板としては、ソーダガラスや無アルカリガラスなどのガラス基板が好適に用いられる。ガラス基板の厚みは、機械的強度を保つのに十分な厚みがあればよいので、０．５ｍｍ以上あれば十分である。ガラスの材質については、ガラスからの溶出イオンが少ない方がよいので無アルカリガラスの方が好ましいが、ＳｉＯ２などのバリアコートを施したソーダライムガラスも市販されているのでこれを使用することもできる。さらに、陽極が安定に機能するのであれば、基板はガラスである必要はなく、例えば、プラスチック基板上に陽極を形成してもよい。ＩＴＯ膜形成方法は、電子線ビーム法、スパッタリング法および化学反応法など特に制限を受けるものではない。 In order to maintain the mechanical strength of the light emitting element, the light emitting element is preferably formed over a substrate. As the substrate, a glass substrate such as soda glass or non-alkali glass is preferably used. As the thickness of the glass substrate, it is sufficient that the thickness is sufficient to maintain the mechanical strength. The glass material is preferably alkali-free glass because it is better to have less ions eluted from the glass, but soda lime glass with a barrier coat such as SiO 2 is also available on the market. it can. Furthermore, if the anode functions stably, the substrate does not have to be glass. For example, the anode may be formed on a plastic substrate. The ITO film forming method is not particularly limited, such as an electron beam method, a sputtering method, and a chemical reaction method.
本発明で用いられる陰極に用いられる材料としては、電子を有機層に効率良く注入できる物質であれば特に限定されないが、一般に白金、金、銀、銅、鉄、錫、亜鉛、アルミニウム、インジウム、クロム、リチウム、ナトリウム、カリウム、セシウム、カルシウム、マグネシウムおよびこれらの合金などが挙げられる。電子注入効率をあげて素子特性を向上させるためには、リチウム、ナトリウム、カリウム、セシウム、カルシウム、マグネシウムまたはこれら低仕事関数金属を含む合金が有効である。しかしながら、これらの低仕事関数金属は、一般に大気中で不安定であることが多く、例えば、有機層に微量のリチウムやマグネシウム（真空蒸着の膜厚計表示で１ｎｍ以下）をドーピングして安定性の高い電極を使用する方法が好ましい例として挙げることができる。また、フッ化リチウムのような無機塩の使用も可能である。更に、電極保護のために白金、金、銀、銅、鉄、錫、アルミニウムおよびインジウムなどの金属、またはこれら金属を用いた合金、そしてシリカ、チタニアおよび窒化ケイ素などの無機物、ポリビニルアルコール、塩化ビニル、炭化水素系高分子化合物などを積層することが、好ましい例として挙げられる。これらの電極の作製法は、抵抗加熱、電子線ビーム、スパッタリング、イオンプレーティングおよびコーティングなど、導通を取ることができれば特に制限されない。 The material used for the cathode used in the present invention is not particularly limited as long as it can efficiently inject electrons into the organic layer, but generally platinum, gold, silver, copper, iron, tin, zinc, aluminum, indium, Examples thereof include chromium, lithium, sodium, potassium, cesium, calcium, magnesium, and alloys thereof. Lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective for increasing the electron injection efficiency and improving device characteristics. However, these low work function metals are generally unstable in the atmosphere. For example, the organic layer is doped with a small amount of lithium or magnesium (1 nm or less in the vacuum vapor deposition thickness meter display) to be stable. A method using a high electrode can be cited as a preferred example. Also, an inorganic salt such as lithium fluoride can be used. Furthermore, for electrode protection, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys using these metals, and inorganic substances such as silica, titania and silicon nitride, polyvinyl alcohol, vinyl chloride Lamination of hydrocarbon polymer compounds and the like is a preferred example. The method for producing these electrodes is not particularly limited as long as conduction can be achieved, such as resistance heating, electron beam, sputtering, ion plating, and coating.
本発明の発光素子を構成する有機層は、発光素子材料からなる少なくとも発光層から構成される。有機層の構成例としては、発光層のみからなる構成の他に、１）正孔輸送層／発光層／電子輸送層および、２）発光層／電子輸送層、３）正孔輸送層／発光層などの積層構成が挙げられる。また、上記各層は、それぞれ単一層からなってもよいし、複数層からなってもよい。正孔輸送層および電子輸送層が複数層からなる場合、電極に接する側の層をそれぞれ正孔注入層および電子注入層と呼ぶことがあるが、以下の説明では正孔注入材料は正孔輸送材料に、電子注入材料は電子輸送材料にそれぞれ含まれる。 The organic layer constituting the light emitting device of the present invention is composed of at least a light emitting layer made of a light emitting device material. As an example of the organic layer configuration, in addition to the configuration consisting of only the light emitting layer, 1) hole transport layer / light emitting layer / electron transport layer and 2) light emitting layer / electron transport layer, 3) hole transport layer / light emission A laminated structure such as a layer can be mentioned. Moreover, each said layer may consist of a single layer, respectively, and may consist of multiple layers. When the hole transport layer and the electron transport layer are composed of a plurality of layers, the layers in contact with the electrode may be referred to as the hole injection layer and the electron injection layer, respectively. In the material, the electron injection material is included in the electron transport material.
正孔輸送層は、正孔輸送材料の一種または二種以上を積層、混合するか、正孔輸送材料と高分子結着剤の混合物により形成される。正孔輸送材料としては、例えば、４，４’−ビス（Ｎ−（３−メチルフェニル）−Ｎ−フェニルアミノ）ビフェニル、４，４’−ビス（Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ）ビフェニル、４，４’，４”−トリス（３−メチルフェニル（フェニル）アミノ）トリフェニルアミンなどのトリフェニルアミン誘導体、ビス（Ｎ−アリルカルバゾール）またはビス（Ｎ−アルキルカルバゾール）などのビスカルバゾール誘導体、ピラゾリン誘導体、スチルベン系化合物、ヒドラゾン系化合物、ベンゾフラン誘導体やチオフェン誘導体、オキサジアゾール誘導体、フタロシアニン誘導体、ポルフィリン誘導体などの複素環化合物、ポリマー系では前記単量体を側鎖に有するポリカーボネートやスチレン誘導体、ポリチオフェン、ポリアニリン、ポリフルオレン、ポリビニルカルバゾールおよびポリシランなどが好ましいが、発光素子の作製に必要な薄膜を形成し、陽極から正孔が注入できて、さらに正孔を輸送できる化合物であれば特に限定されるものではない。 The hole transport layer is formed by laminating and mixing one or more hole transport materials or a mixture of the hole transport material and the polymer binder. Examples of the hole transport material include 4,4′-bis (N- (3-methylphenyl) -N-phenylamino) biphenyl and 4,4′-bis (N- (1-naphthyl) -N-phenyl. Amino) biphenyl, triphenylamine derivatives such as 4,4 ′, 4 ″ -tris (3-methylphenyl (phenyl) amino) triphenylamine, bis (N-allylcarbazole) or bis (N-alkylcarbazole) Biscarbazole derivatives, pyrazoline derivatives, stilbene compounds, hydrazone compounds, benzofuran derivatives and thiophene derivatives, oxadiazole derivatives, phthalocyanine derivatives, porphyrin derivatives and other heterocyclic compounds, and polymers having the above monomers in the side chain And styrene derivatives, polythiophene, polyaniline Polyfluorene, polyvinylcarbazole, polysilane, and the like are preferable, but there is no particular limitation as long as it is a compound that can form a thin film necessary for manufacturing a light-emitting element, can inject holes from the anode, and can further transport holes. .
本発明において、発光層とは陽極および陰極より注入された電気エネルギーを発光のためのエネルギーとして蓄積して、実際に発光を司る層である。本発明の発光層は少なくともホスト材料とドーパント材料とからなり、ホスト材料は下記一般式（１）で表されるカルバゾール骨格を有する化合物であり、ドーパント材料は三重項発光材料である。 In the present invention, the light emitting layer is a layer that actually manages light emission by accumulating electric energy injected from the anode and the cathode as energy for light emission. The light emitting layer of the present invention comprises at least a host material and a dopant material. The host material is a compound having a carbazole skeleton represented by the following general formula (1), and the dopant material is a triplet light emitting material.
Ｒ１〜Ｒ２４はそれぞれ、水素、アルキル基、シクロアルキル基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、アミノ基、シリル基、あるいは隣接する置換基との間の環構造の中から選ばれる。但し、Ｒ１５〜Ｒ２４の少なくとも一つはアミノ基、隣接する置換基との環構造より選ばれる。 R 1 to R 24 are each a hydrogen, an alkyl group, a cycloalkyl group, an alkoxy group, an alkylthio group, an aryl ether group, an aryl thioether group, an aryl group, an amino group, a silyl group, or a ring between adjacent substituents. Selected from among structures. However, at least one of R 15 to R 24 is selected from an amino group and a ring structure with an adjacent substituent.
これらの置換基のうち、アルキル基とは、例えば、メチル基、エチル基、プロピル基、ブチル基などの飽和脂肪族炭化水素基を示し、これは無置換でも置換されていてもかまわない。置換されている場合の置換基には特に制限は無く、例えば、アルキル基、アリール基、ヘテロアリール基等を挙げることができ、この点は、以下の記載にも共通する。また、アルキル基の炭素数は特に限定されないが、入手の容易性やコストの点から、通常、１〜２０の範囲である。 Among these substituents, the alkyl group represents, for example, a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, or a butyl group, which may be unsubstituted or substituted. The substituent in the case of being substituted is not particularly limited, and examples thereof include an alkyl group, an aryl group, a heteroaryl group, and the like, and this point is common to the following description. Further, the number of carbon atoms of the alkyl group is not particularly limited, but is usually in the range of 1 to 20 from the viewpoint of availability and cost.
また、シクロアルキル基とは、例えば、シクロプロピル、シクロヘキシル、ノルボルニル、アダマンチルなどの飽和脂環式炭化水素基を示し、これは無置換でも置換されていてもかまわない。アルキル基部分の炭素数は特に限定されないが、通常、３〜２０の範囲である。 The cycloalkyl group represents a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, and the like, which may be unsubstituted or substituted. Although carbon number of an alkyl group part is not specifically limited, Usually, it is the range of 3-20.
また、アルコキシ基とは、例えば、メトキシ基などのエーテル結合を介した脂肪族炭化水素基を示し、脂肪族炭化水素基は無置換でも置換されていてもかまわない。アルコキシ基の炭素数は特に限定されないが、通常、１〜２０の範囲である。 The alkoxy group refers to, for example, an aliphatic hydrocarbon group via an ether bond such as a methoxy group, and the aliphatic hydrocarbon group may be unsubstituted or substituted. Although carbon number of an alkoxy group is not specifically limited, Usually, it is the range of 1-20.
また、アルキルチオ基とは、アルコキシ基のエーテル結合の酸素原子が硫黄原子に置換されたものである。 The alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom.
また、アリールエーテル基とは、例えば、フェノキシ基などのエーテル結合を介した芳香族炭化水素基を示し、芳香族炭化水素基は無置換でも置換されていてもかまわない。アリールエーテル基の炭素数は特に限定されないが、通常、６〜４０の範囲である。 The aryl ether group refers to, for example, an aromatic hydrocarbon group via an ether bond such as a phenoxy group, and the aromatic hydrocarbon group may be unsubstituted or substituted. Although carbon number of an aryl ether group is not specifically limited, Usually, it is the range of 6-40.
また、アリールチオエーテル基とは、アリールエーテル基のエーテル結合の酸素原子が硫黄原子に置換されたものである。 The arylthioether group is a group in which the oxygen atom of the ether bond of the arylether group is substituted with a sulfur atom.
また、アリール基とは、例えば、フェニル基、ナフチル基、ビフェニル基、フェナントリル基、ターフェニル基、ピレニル基などの芳香族炭化水素基を示す。アリール基は、無置換でも置換されていてもかまわない。アリール基の炭素数は特に限定されないが、通常、６〜４０の範囲である。 Moreover, an aryl group shows aromatic hydrocarbon groups, such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, a pyrenyl group, for example. The aryl group may be unsubstituted or substituted. Although carbon number of an aryl group is not specifically limited, Usually, it is the range of 6-40.
アミノ基は、置換基を有していても有していなくてもよく、置換基は例えばアルキル基、シクロアルキル基、アリール基、ヘテロアリール基などが挙げられ、これら置換基はさらに置換されてもよい。 The amino group may or may not have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group. These substituents are further substituted. Also good.
シリル基とは、例えば、トリメチルシリル基などのケイ素原子への結合を有する官能基を示し、これは置換基を有していても有していなくてもよい。シリル基の炭素数は特に限定されないが、通常、３以上２０以下の範囲である。また、ケイ素数は、通常、１以上６以下である。 A silyl group refers to, for example, a functional group having a bond to a silicon atom, such as a trimethylsilyl group, which may or may not have a substituent. Although carbon number of a silyl group is not specifically limited, Usually, it is the range of 3-20. The number of silicon is usually 1 or more and 6 or less.
隣接基との間に形成される環構造とは、前記一般式（１）で説明すると、Ｒ１５〜Ｒ１９の中から選ばれる任意の隣接２置換基（例えばＲ１５とＲ１６）が互いに結合して共役または非供役の環構造を形成するものである。これら環構造は環内構造に窒素、酸素、硫黄原子を含んでいてもよいし、さらに別の環と縮合していてもよいが、これら環構造を構成する原子が炭素原子と水素原子のみからなる共役の環構造であると、優れた耐熱性が得られるため好ましい。 When the ring structure formed between adjacent groups is described in the general formula (1), any two adjacent substituents selected from R 15 to R 19 (for example, R 15 and R 16 ) are mutually bonded. Bonds to form a conjugated or non-serving ring structure. These ring structures may contain nitrogen, oxygen and sulfur atoms in the ring structure, or may be condensed with another ring, but the atoms constituting these ring structures are composed of only carbon atoms and hydrogen atoms. The conjugated ring structure is preferable because excellent heat resistance can be obtained.
本発明の一般式（１）で表されるカルバゾール骨格を有する化合物は、Ｒ１５〜Ｒ２４の少なくとも一つがアミノ基で置換されているか、もしくは隣接する置換基との環構造を有することで、キャリア輸送性が向上し、ドーパントである三重項発光材料への高効率エネルギー移動と低駆動電圧の両立が可能となる。それ以外の置換基Ｒとしては本発明の効果に照らしてカルバゾール骨格上の水素とそれに等価の特性を有する置換基を列挙したものである。 The compound having a carbazole skeleton represented by the general formula (1) of the present invention has at least one of R 15 to R 24 substituted with an amino group or a ring structure with an adjacent substituent. Carrier transportability is improved, and both high-efficiency energy transfer to a triplet light-emitting material as a dopant and a low driving voltage can be achieved. As the other substituents R, in view of the effects of the present invention, hydrogen on the carbazole skeleton and substituents having equivalent properties are listed.
上記カルバゾール骨格を有する化合物として、具体的には下記のような構造が挙げられる。 Specific examples of the compound having the carbazole skeleton include the following structures.
ドーパント材料として用いられる三重項発光材料としては、イリジウム、オスミウム、ロジウム、パラジウム、白金を中心金属に有する金属錯体が好適に用いられ、具体的には、トリス（２−フェニルピリジル）イリジウム錯体、トリス｛２−（２−チオフェニル）ピリジル｝イリジウム錯体、トリス｛２−（２−ベンゾチオフェニル）ピリジル｝イリジウム錯体、トリス（２−フェニルベンゾチアゾール）イリジウム錯体、トリス（２−フェニルベンゾオキサゾール）イリジウム錯体、トリスベンゾキノリンイリジウム錯体、ビス（２−フェニルピリジル）（アセチルアセトナート）イリジウム錯体、ビス｛２−（２−チオフェニル）ピリジル｝イリジウム錯体、ビス｛２−（２−ベンゾチオフェニル）ピリジル｝（アセチルアセトナート）イリジウム錯体、ビス（２−フェニルベンゾチアゾール）（アセチルアセトナート）イリジウム錯体、ビス（２−フェニルベンゾオキサゾール）（アセチルアセトナート）イリジウム錯体、ビスベンゾキノリン（アセチルアセトナート）イリジウム錯体、ビス｛２−（２，４−ジフルオロフェニル）ピリジル｝（アセチルアセトナート）イリジウム錯体、テトラエチルポルフィリン白金錯体、｛トリス（セノイルトリフルオロアセトン）モノ（１，１０−フェナントロリン）｝ユーロピウム錯体、｛トリス（セノイルトリフルオロアセトン）モノ（４，７−ジフェニル−１，１０−フェナントロリン）｝ユーロピウム錯体、｛トリス（１，３−ジフェニル−１，３−プロパンジオン）モノ（１，１０−フェナントロリン）｝ユーロピウム錯体、トリスアセチルアセトンテルビウム錯体などが挙げられる。これらに限定されるものではないが、高効率発光が得られやすいことから、イリジウム錯体または白金錯体が好ましく用いられる。 As a triplet light emitting material used as a dopant material, a metal complex having iridium, osmium, rhodium, palladium, platinum as a central metal is preferably used. Specifically, a tris (2-phenylpyridyl) iridium complex, tris {2- (2-thiophenyl) pyridyl} iridium complex, tris {2- (2-benzothiophenyl) pyridyl} iridium complex, tris (2-phenylbenzothiazole) iridium complex, tris (2-phenylbenzoxazole) iridium complex , Trisbenzoquinoline iridium complex, bis (2-phenylpyridyl) (acetylacetonato) iridium complex, bis {2- (2-thiophenyl) pyridyl} iridium complex, bis {2- (2-benzothiophenyl) pyridyl} ( Acetylacetonate Iridium complex, bis (2-phenylbenzothiazole) (acetylacetonato) iridium complex, bis (2-phenylbenzoxazole) (acetylacetonato) iridium complex, bisbenzoquinoline (acetylacetonato) iridium complex, bis {2- (2,4-difluorophenyl) pyridyl} (acetylacetonato) iridium complex, tetraethylporphyrin platinum complex, {tris (cenoyltrifluoroacetone) mono (1,10-phenanthroline)} europium complex, {tris (cenoyltrifluoroacetone) ) Mono (4,7-diphenyl-1,10-phenanthroline)} europium complex, {tris (1,3-diphenyl-1,3-propanedione) mono (1,10-phenanthroline)} europium complex , And the like tris-acetylacetone terbium complex. Although not limited thereto, an iridium complex or a platinum complex is preferably used because high-efficiency light emission is easily obtained.
ホスト材料に対するドーパント材料の量は、多すぎると濃度消光現象が起きるため、ホスト材料に対して２０重量％以下で用いることが好ましい。ドーピング方法としては、ホスト材料との共蒸着法によって形成することができるが、ホスト材料と予め混合してから同時に蒸着してもよい。または、ホスト材料とドーパント材料を望む割合で溶媒に溶かし、塗布してもよい。 If the amount of the dopant material relative to the host material is too large, a concentration quenching phenomenon occurs. As a doping method, it can be formed by a co-evaporation method with a host material, but it may be pre-mixed with the host material and then simultaneously deposited. Alternatively, the host material and the dopant material may be dissolved in a desired ratio and applied.
ホスト材料として用いられる前記カルバゾール骨格を有する化合物およびドーパント材料として用いられる前記三重項発光材料は、発光層中に各々一種類のみが含まれていてもよいし、二種以上を混合して用いてもよい。三重項発光材料を二種以上用いる際には、ドーパント材料の総重量がホスト材料に対して２０重量％以下であることが好ましい。 The compound having a carbazole skeleton used as a host material and the triplet light emitting material used as a dopant material may each include only one type in the light emitting layer, or a mixture of two or more types may be used. Also good. When two or more triplet light emitting materials are used, the total weight of the dopant material is preferably 20% by weight or less with respect to the host material.
また、発光層には上記ホスト材料および三重項発光材料の他に、発光層内のキャリヤバランスを調整するためや発光層の層構造を安定化させるための第３成分を更に含んでいてもよい。但し、第３成分としては、上記カルバゾール骨格を有する化合物からなるホスト材料および三重項発光材料からなるドーパント材料との間で相互作用を起こさないような材料を選択する。 In addition to the host material and the triplet light emitting material, the light emitting layer may further include a third component for adjusting the carrier balance in the light emitting layer or stabilizing the layer structure of the light emitting layer. . However, as the third component, a material that does not cause an interaction between the host material composed of the compound having the carbazole skeleton and the dopant material composed of the triplet light emitting material is selected.
さらに、発光層は上記材料群からなる単一層だけでなく、複数層で構成されていてもよい。複数層で構成されている場合には、少なくとも一層に前記カルバゾール骨格を有する化合物および三重項発光材料が含まれていればよく、他の層において、既知のホスト材料および一重項発光材料からなる蛍光性ドーパント材料を用いてもよい。 Furthermore, the light emitting layer may be composed of a plurality of layers as well as a single layer made of the above material group. In the case of being composed of a plurality of layers, it is sufficient that at least one layer contains the compound having the carbazole skeleton and the triplet light-emitting material, and the fluorescent light comprising the known host material and singlet light-emitting material is contained in the other layers. An ionic dopant material may be used.
既知のホスト材料としては特に限定されるものではないが、以前から発光体として知られていたアントラセン、ピレンなどの縮合環誘導体、４，４’−ビス（Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ）ビフェニルなどの芳香族アミン誘導体、トリス（８−キノリノラート）アルミニウム（III）をはじめとする金属キレート化オキシノイド化合物、ジスチリルベンゼン誘導体などのビススチリル誘導体、テトラフェニルブタジエン誘導体、インデン誘導体、オキサジアゾール誘導体、ピロロピリジン誘導体、ペリノン誘導体、シクロペンタジエン誘導体、オキサジアゾール誘導体、ピロロピロール誘導体、ポリマー系では、ポリフェニレンビニレン誘導体、ポリパラフェニレン誘導体、ポリフルオレン誘導体、ポリビニルカルバゾール誘導体、ポリチオフェン誘導体が好適に用いられる。 Although it does not specifically limit as a known host material, Condensed ring derivatives, such as anthracene and pyrene which were known as a light-emitting body, 4,4'-bis (N- (1-naphthyl) -N- Aromatic amine derivatives such as phenylamino) biphenyl, metal chelated oxinoid compounds such as tris (8-quinolinolato) aluminum (III), bisstyryl derivatives such as distyrylbenzene derivatives, tetraphenylbutadiene derivatives, indene derivatives, oxadi Azole derivatives, pyrrolopyridine derivatives, perinone derivatives, cyclopentadiene derivatives, oxadiazole derivatives, pyrrolopyrrole derivatives, in polymer systems, polyphenylene vinylene derivatives, polyparaphenylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives , Polythiophene derivatives are suitably used.
既知の一重項ドーパント材料としては、特に限定されるものではないが、具体的には従来から知られている、ピレン、ペリレン、ルブレンなどの縮合アリール環を有する化合物やその誘導体、フラン、イソベンゾフラン、ピロール、チオフェン、インドール、イミダゾピリジン、ピラジン、ピロロピリジン、チオキサンテンなどのヘテロアリール環を有する化合物やその誘導体、イミダゾール、チアゾール、チアジアゾール、オキサゾール、オキサジアゾール、トリアゾール、ベンズイミダゾールなどのアゾール誘導体、芳香族アミン誘導体、ピラゾリン誘導体、スチルベン誘導体、ピロメテン誘導体およびその金属錯体、３−ベンズチアゾリルクマリン誘導体などのクマリン誘導体、ジシアノメチレンピラン誘導体、シアニン誘導体、フルオレセイン誘導体、ピリリウム誘導体、カルボスチリル誘導体、アクリジン誘導体、オキサジン誘導体、キナクリドン誘導体、キナゾリン誘導体、ピロロピリジン誘導体、ペリノン誘導体、ピロロピロール誘導体、スクアリリウム誘導体、ビオラントロン誘導体、フェナジン誘導体、アクリドン誘導体、ジアザフラビン誘導体などが使用できる。 The known singlet dopant material is not particularly limited, but specifically, conventionally known compounds having a condensed aryl ring such as pyrene, perylene, rubrene, and derivatives thereof, furan, isobenzofuran. , A compound having a heteroaryl ring such as pyrrole, thiophene, indole, imidazopyridine, pyrazine, pyrrolopyridine, thioxanthene and derivatives thereof, azole derivatives such as imidazole, thiazole, thiadiazole, oxazole, oxadiazole, triazole, benzimidazole, Aromatic amine derivatives, pyrazoline derivatives, stilbene derivatives, pyromethene derivatives and metal complexes thereof, coumarin derivatives such as 3-benzthiazolyl coumarin derivatives, dicyanomethylenepyran derivatives, cyanine derivatives, full Resin derivatives, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, diazaflavin derivatives, etc. it can.
本発明において、電子輸送層とは、陰極から電子が注入され、さらに電子を輸送する層である。電子輸送層には、電子注入効率が高く、注入された電子を効率良く輸送することが望まれる。そのため電子輸送層は、電子親和力が大きく、しかも電子移動度が大きく、さらに安定性に優れ、トラップとなる不純物が製造時および使用時に発生しにくい物質で構成されることが望ましい。しかしながら、正孔と電子の輸送バランスを考えた場合に、電子輸送層が陽極からの正孔が再結合せずに陰極側へ流れるのを効率よく阻止できる役割を主に果たすならば、電子輸送能力がそれ程高くない材料で構成されていても、発光効率を向上させる効果は電子輸送能力が高い材料で構成されている場合と同等となる。したがって、本発明における電子輸送層には、正孔の移動を効率よく阻止できる正孔阻止層も同義のものとして含まれる。 In the present invention, the electron transport layer is a layer in which electrons are injected from the cathode and further transports electrons. The electron transport layer has high electron injection efficiency, and it is desired to efficiently transport injected electrons. Therefore, it is desirable that the electron transport layer is made of a material having a high electron affinity, a high electron mobility, excellent stability, and a trapping impurity that is unlikely to be generated during manufacture and use. However, considering the transport balance between holes and electrons, if the electron transport layer mainly plays a role of effectively preventing the holes from the anode from recombining and flowing to the cathode side, the electron transport Even if it is made of a material that does not have a high capability, the effect of improving the luminous efficiency is equivalent to that of a material that has a high electron transport capability. Therefore, the electron transport layer in the present invention includes a hole blocking layer that can efficiently block the movement of holes as the same meaning.
電子輸送層に用いられる電子輸送材料としては、ナフタレン、アントラセンなどの縮合多環芳香族誘導体、４，４’−ビス（ジフェニルエテニル）ビフェニルに代表されるスチリル系芳香環誘導体、アントラキノンやジフェノキノンなどのキノン誘導体、リンオキサイド誘導体、トリス（８−キノリノラート）アルミニウム（III）などのキノリノール錯体、ベンゾキノリノール錯体、ヒドロキシアゾール錯体、アゾメチン錯体、トロポロン金属錯体およびフラボノール金属錯体などの各種金属錯体が挙げられるが、駆動電圧を低減し、高効率発光が得られることから、炭素、水素、窒素、酸素、ケイ素、リンの中から選ばれる元素で構成され、電子受容性窒素を含むヘテロアリール環構造を有する化合物を用いることが好ましい。特に、本発明のピロメテン骨格を有する化合物もしくはその金属錯体とナフタセン誘導体とを含有する発光層と組み合わせて用いることで、発光素子内での正孔・電子のバランスを保ちやすく、また、そのバランスが高い電荷輸送能を維持したまま実現されることから、低駆動電圧と長寿命の両立が可能となる。 Examples of the electron transport material used in the electron transport layer include condensed polycyclic aromatic derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4′-bis (diphenylethenyl) biphenyl, anthraquinone, diphenoquinone, and the like. Quinoline derivatives, phosphorus oxide derivatives, quinolinol complexes such as tris (8-quinolinolato) aluminum (III), benzoquinolinol complexes, hydroxyazole complexes, azomethine complexes, tropolone metal complexes and flavonol metal complexes. A compound having a heteroaryl ring structure composed of an element selected from carbon, hydrogen, nitrogen, oxygen, silicon, and phosphorus and containing electron-accepting nitrogen, because driving voltage is reduced and high-efficiency light emission is obtained. Is preferably used. In particular, when used in combination with a light-emitting layer containing a compound having a pyromethene skeleton of the present invention or a metal complex thereof and a naphthacene derivative, it is easy to maintain the balance of holes and electrons in the light-emitting element, and the balance is Since it is realized while maintaining a high charge transport capability, it is possible to achieve both a low driving voltage and a long life.
本発明における電子受容性窒素とは、隣接原子との間に多重結合を形成している窒素原子を表す。窒素原子が高い電子陰性度を有することから、該多重結合は電子受容的な性質を有する。それゆえ、電子受容性窒素を含むヘテロアリール環は、高い電子親和性を有し、電子輸送能に優れ、電子輸送層に用いることで発光素子の駆動電圧を低減できる。電子受容性窒素を含むヘテロアリール環は、例えば、ピリジン環、ピラジン環、ピリミジン環、キノリン環、キノキサリン環、ナフチリジン環、ピリミドピリミジン環、ベンゾキノリン環、フェナントロリン環、イミダゾール環、オキサゾール環、オキサジアゾール環、トリアゾール環、チアゾール環、チアジアゾール環、ベンゾオキサゾール環、ベンゾチアゾール環、ベンズイミダゾール環、フェナンスロイミダゾール環などが挙げられる。 The electron-accepting nitrogen in the present invention represents a nitrogen atom that forms a multiple bond with an adjacent atom. Since the nitrogen atom has a high electronegativity, the multiple bond has an electron accepting property. Therefore, a heteroaryl ring containing electron-accepting nitrogen has high electron affinity, excellent electron transport ability, and can be used for an electron transport layer to reduce the driving voltage of a light-emitting element. Heteroaryl rings containing electron-accepting nitrogen include, for example, pyridine ring, pyrazine ring, pyrimidine ring, quinoline ring, quinoxaline ring, naphthyridine ring, pyrimidopyrimidine ring, benzoquinoline ring, phenanthroline ring, imidazole ring, oxazole ring, oxalate ring, Examples include a diazole ring, a triazole ring, a thiazole ring, a thiadiazole ring, a benzoxazole ring, a benzothiazole ring, a benzimidazole ring, and a phenanthrimidazole ring.
これらのヘテロアリール環構造を有する化合物としては、例えば、ベンズイミダゾール誘導体、ベンズオキサゾール誘導体、ベンズチアゾール誘導体、オキサジアゾール誘導体、チアジアゾール誘導体、トリアゾール誘導体、ピラジン誘導体、フェナントロリン誘導体、キノキサリン誘導体、キノリン誘導体、ベンゾキノリン誘導体、ビピリジンやターピリジンなどのオリゴピリジン誘導体、キノキサリン誘導体およびナフチリジン誘導体などが好ましい化合物として挙げられる。中でも、トリス（Ｎ−フェニルベンズイミダゾール−２−イル）ベンゼンなどのイミダゾール誘導体、１，３−ビス［（４−ｔｅｒｔ−ブチルフェニル）１，３，４−オキサジアゾリル］フェニレンなどのオキサジアゾール誘導体、Ｎ−ナフチル−２，５−ジフェニル−１，３，４−トリアゾールなどのトリアゾール誘導体、バソクプロインや１，３−ビス（１，１０−フェナントロリン−９−イル）ベンゼンなどのフェナントロリン誘導体、２，２’−ビス（ベンゾ［ｈ］キノリン−２−イル）−９，９’−スピロビフルオレンなどのベンゾキノリン誘導体、２，５−ビス（６’−（２’，２”−ビピリジル））−１，１−ジメチル−３，４−ジフェニルシロールなどのビピリジン誘導体、１，３−ビス（４’−（２，２’：６’２”−ターピリジニル））ベンゼンなどのターピリジン誘導体、ビス（１−ナフチル）−４−（１，８−ナフチリジン−２−イル）フェニルホスフィンオキサイドなどのナフチリジン誘導体が、電子輸送能の点から好ましく用いられる。 Examples of these compounds having a heteroaryl ring structure include benzimidazole derivatives, benzoxazole derivatives, benzthiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazine derivatives, phenanthroline derivatives, quinoxaline derivatives, quinoline derivatives, benzoins. Preferred compounds include quinoline derivatives, oligopyridine derivatives such as bipyridine and terpyridine, quinoxaline derivatives and naphthyridine derivatives. Among them, imidazole derivatives such as tris (N-phenylbenzimidazol-2-yl) benzene, oxadiazole derivatives such as 1,3-bis [(4-tert-butylphenyl) 1,3,4-oxadiazolyl] phenylene, Triazole derivatives such as N-naphthyl-2,5-diphenyl-1,3,4-triazole, phenanthroline derivatives such as bathocuproine and 1,3-bis (1,10-phenanthroline-9-yl) benzene, 2,2 ′ A benzoquinoline derivative such as bis (benzo [h] quinolin-2-yl) -9,9′-spirobifluorene, 2,5-bis (6 ′-(2 ′, 2 ″ -bipyridyl))-1, Bipyridine derivatives such as 1-dimethyl-3,4-diphenylsilole, 1,3-bis (4 ′-(2,2 ′: 6′2 ″ -ta Terpyridine derivatives such as pyridinyl)) benzene, naphthyridine derivatives such as bis (1-naphthyl) -4- (1,8-naphthyridin-2-yl) phenylphosphine oxide are preferably used from the viewpoint of electron transporting capability.
上記電子輸送材料は単独でも用いられるが、上記電子輸送材料の２種以上を混合して用いたり、その他の電子輸送材料の一種以上を上記の電子輸送材料に混合して用いても構わない。また、アルカリ金属やアルカリ土類金属などの金属と混合して用いることも可能である。電子輸送層のイオン化ポテンシャルは、特に限定されないが、好ましくは５．８ｅＶ以上８ｅＶ以下であり、より好ましくは６ｅＶ以上７．５ｅＶ以下である。 The electron transport material may be used alone, but two or more of the electron transport materials may be mixed and used, or one or more of the other electron transport materials may be mixed and used in the electron transport material. It is also possible to use a mixture with a metal such as an alkali metal or an alkaline earth metal. The ionization potential of the electron transport layer is not particularly limited, but is preferably 5.8 eV or more and 8 eV or less, more preferably 6 eV or more and 7.5 eV or less.
発光素子を構成する上記各層の形成方法は、抵抗加熱蒸着、電子ビーム蒸着、スパッタリング、分子積層法、コーティング法、インクジェット法、印刷法、レーザー誘起熱転写法など特に限定されないが、通常は、素子特性の点から抵抗加熱蒸着または電子ビーム蒸着が好ましい。 The method of forming each of the above layers constituting the light emitting element is not particularly limited, such as resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, coating method, ink jet method, printing method, laser induced thermal transfer method, etc. From this point, resistance heating vapor deposition or electron beam vapor deposition is preferable.
本発明の発光素子は、電気エネルギーを光に変換できる発光素子である。ここに電気エネルギーとは主に直流電流を指すが、パルス電流や交流電流を用いることも可能である。電流値および電圧値は特に制限はないが、素子の消費電力や寿命を考慮すると、できるだけ低いエネルギーで最大の輝度が得られるようにする。 The light-emitting element of the present invention is a light-emitting element that can convert electrical energy into light. Here, the electric energy mainly indicates a direct current, but a pulse current or an alternating current can also be used. The current value and the voltage value are not particularly limited, but the maximum luminance can be obtained with as low energy as possible in consideration of the power consumption and lifetime of the element.
本発明の発光素子は、例えば、マトリクスおよび／またはセグメント方式で表示するディスプレイとして好適に用いられる。 The light emitting device of the present invention is suitably used as a display for displaying in a matrix and / or segment system, for example.
本発明におけるマトリクス方式とは、表示のための画素が格子状やモザイク状など二次元的に配置されたものをいい、画素の集合で文字や画像を表示する。画素の形状やサイズは用途によって決まる。例えば、パソコン、モニター、テレビの画像および文字表示には、通常一辺が３００μｍ以下の四角形の画素が用いられ、また、表示パネルのような大型ディスプレイの場合は、一辺がｍｍオーダーの画素を用いることになる。モノクロ表示の場合は、同じ色の画素を配列すればよいが、カラー表示の場合には、赤、緑、青の画素を並べて表示させる。この場合、典型的にはデルタタイプとストライプタイプがある。そして、このマトリクスの駆動方法としては、線順次駆動方法やアクティブマトリクスのどちらでもよい。線順次駆動の方が構造が簡単であるという利点があるが、動作特性を考慮した場合、アクティブマトリクスの方が優れる場合があるので、これも用途によって使い分ける。 The matrix system in the present invention refers to a pixel in which pixels for display are two-dimensionally arranged such as a lattice shape or a mosaic shape, and displays characters and images by a set of pixels. The shape and size of the pixel are determined by the application. For example, a square pixel with a side of 300 μm or less is usually used for displaying images and characters on a personal computer, monitor, TV, and a pixel with a side of mm order for a large display such as a display panel. become. In monochrome display, pixels of the same color may be arranged. However, in color display, red, green, and blue pixels are displayed side by side. In this case, there are typically a delta type and a stripe type. The matrix driving method may be either a line sequential driving method or an active matrix. The line-sequential driving has an advantage that the structure is simple, but the active matrix may be superior in consideration of operation characteristics.
本発明におけるセグメント方式（タイプ）とは、予め決められた情報を表示するようにパターンを形成し、決められた領域を発光させることになる。例えば、デジタル時計や温度計における時刻や温度表示、オーディオ機器や電磁調理器などの動作状態表示および自動車のパネル表示などが挙げられる。そして、前記マトリクス表示とセグメント表示は同じパネルの中に共存していてもよい。 In the segment system (type) in the present invention, a pattern is formed so as to display predetermined information, and a predetermined region is caused to emit light. For example, the time and temperature display in a digital clock or a thermometer, the operation state display of an audio device or an electromagnetic cooker, the panel display of an automobile, and the like can be mentioned. The matrix display and the segment display may coexist in the same panel.
本発明の発光素子は、各種機器等のバックライトとしても好ましく用いられる。バックライトは、主に自発光しない表示装置の視認性を向上させる目的に使用され、液晶表示装置、時計、オーディオ装置、自動車パネル、表示板および標識などに使用される。特に、液晶表示装置、中でも薄型化が課題となっているパソコン用途のバックライトとしては、従来のものが蛍光灯や導光板からなっているため薄型化が困難であることを考えると、本発明における発光素子を用いたバックライトは薄型、軽量にすることができる。 The light emitting device of the present invention is also preferably used as a backlight for various devices. The backlight is used mainly for the purpose of improving the visibility of a display device that does not emit light, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display panel, a sign, and the like. In particular, as a backlight for a liquid crystal display device, especially a personal computer for which thinning is a problem, considering that it is difficult to thin the conventional backlight because it is made of a fluorescent lamp or a light guide plate, the present invention The backlight using the light emitting element in can be made thin and light.
以下、実施例および比較例を挙げて本発明を説明するが、本発明はこれらの例によって限定されるものではない。なお、下記の各実施例にある化合物の番号は上記に記載した化合物の番号を指すものである。 EXAMPLES Hereinafter, although an Example and a comparative example are given and this invention is demonstrated, this invention is not limited by these examples. In addition, the number of the compound in each following Example points out the number of the compound described above.
実施例１
ＩＴＯ透明導電膜を１５０ｎｍ堆積させたガラス基板（ジオマテック（株）製、１１Ω／□、スパッタによる形成品）を３８×４６ｍｍに切断し、エッチングを行った。得られた基板を “セミコクリン５６”（商品名、フルウチ化学（株）製）で１５分間超音波洗浄してから、超純水で洗浄した。この基板を素子を作製する直前に１時間ＵＶ−オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が５×１０−４Ｐａ以下になるまで排気した。抵抗加熱法によって、まず正孔注入材料として、銅フタロシアニンを１０ｎｍ、正孔輸送材料として、４，４’−ビス（Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ）ビフェニルを５０ｎｍ蒸着した。次に、発光材料として、ホスト材料として化合物〔２〕を、ドーパント材料としてビス（２−フェニルキノリン）（アセチルアセトナト）イリジウム錯体をドープ濃度が１０％になるように３５ｎｍの厚さに蒸着した。次に、正孔阻止材料として、ビス（２−メチル−８−キノリノラト）−（４−フェニルフェノラート）アルミニウム錯体を１０ｎｍ、電子輸送材料として、トリス（８−キノリノラト）アルミニウム錯体を６５ｎｍの厚さに積層した。次に、フッ化リチウムを０．５ｎｍ蒸着した後、アルミニウムを１０００ｎｍ蒸着して陰極とし、５×５ｍｍ角の素子を作製した。ここで言う膜厚は、水晶発振式膜厚モニター表示値である。この発光素子は、１０ｍＡ／ｃｍ２で直流駆動したところ、発光効率５ｃｄ／Ａ、色度ＣＩＥ（ｘ，ｙ）＝（０．６６、０．３３）の赤色発光が得られ、このときの駆動電圧は８Ｖであった。
Example 1
A glass substrate (manufactured by Geomat Co., Ltd., 11Ω / □, product formed by sputtering) on which an ITO transparent conductive film was deposited to 150 nm was cut into 38 × 46 mm and etched. The obtained substrate was ultrasonically cleaned with “Semicocrine 56” (trade name, manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes and then with ultrapure water. This substrate was subjected to UV-ozone treatment for 1 hour immediately before producing the device, placed in a vacuum deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 × 10 −4 Pa or less. By the resistance heating method, first, copper phthalocyanine was deposited as a hole injecting material at 10 nm, and 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl was deposited as a hole transporting material at 50 nm. Next, the compound [2] as a host material and a bis (2-phenylquinoline) (acetylacetonato) iridium complex as a dopant material were vapor-deposited to a thickness of 35 nm so as to have a doping concentration of 10%. . Next, bis (2-methyl-8-quinolinolato)-(4-phenylphenolate) aluminum complex is 10 nm as the hole blocking material, and tris (8-quinolinolato) aluminum complex is 65 nm thick as the electron transporting material. Laminated. Next, after depositing 0.5 nm of lithium fluoride, 1000 nm of aluminum was vapor-deposited to form a cathode, and a 5 × 5 mm square device was fabricated. The film thickness referred to here is a crystal oscillation type film thickness monitor display value. When this light emitting element was DC-driven at 10 mA / cm 2 , red light emission with a light emission efficiency of 5 cd / A and chromaticity CIE (x, y) = (0.66, 0.33) was obtained. The voltage was 8V.
比較例１
発光材料のホスト材料として４，４’−ビス（Ｎ−カルバゾリル）ビフェニル（ＣＢＰ）を用いた以外は実施例１と全く同様にして発光素子を作製した。この発光素子は、１０ｍＡ／ｃｍ２で直流駆動したところ、発光効率４．３ｃｄ／Ａ、色度ＣＩＥ（ｘ，ｙ）＝（０．６５、０．３３）の赤色発光が得られ、このときの駆動電圧は１３．３Ｖであった。
Comparative Example 1
A light emitting device was produced in the same manner as in Example 1 except that 4,4′-bis (N-carbazolyl) biphenyl (CBP) was used as the host material of the light emitting material. When this light emitting device was DC-driven at 10 mA / cm 2 , red light emission with a luminous efficiency of 4.3 cd / A and chromaticity CIE (x, y) = (0.65, 0.33) was obtained. The drive voltage was 13.3V.
実施例２
実施例１の正孔阻止材料および電子輸送材料の代わりに、電子輸送材料として、１，３−ビス（１，１０−フェナントロリン−９−イル）ベンゼンを７５ｎｍの厚さに蒸着した以外は実施例１と同様にして発光素子を作製した。この発光素子は、１０ｍＡ／ｃｍ２で直流駆動したところ、発光効率５．８ｃｄ／Ａ、色度ＣＩＥ（ｘ，ｙ）＝（０．６９、０．３０）の赤色発光が得られ、このときの駆動電圧は５．８Ｖであった。
Example 2
Example 1 except that 1,3-bis (1,10-phenanthroline-9-yl) benzene was vapor-deposited to a thickness of 75 nm as an electron transport material instead of the hole blocking material and the electron transport material of Example 1. In the same manner as in Example 1, a light emitting device was manufactured. When this light emitting device was DC driven at 10 mA / cm 2 , red light emission with a light emission efficiency of 5.8 cd / A and chromaticity CIE (x, y) = (0.69, 0.30) was obtained. The driving voltage was 5.8V.
実施例３
発光材料のホスト材料を化合物〔７〕に変えた以外は、実施例２と同様にして発光素子を作製した。この発光素子は、１０ｍＡ／ｃｍ２で直流駆動したところ、発光効率６ｃｄ／Ａ、色度ＣＩＥ（ｘ，ｙ）＝（０．６９、０．３０）の赤色発光が得られ、このときの駆動電圧は７．３Ｖであった。
Example 3
A light emitting device was produced in the same manner as in Example 2 except that the host material of the light emitting material was changed to the compound [7]. When this light emitting element was DC-driven at 10 mA / cm 2 , red light emission with a luminous efficiency of 6 cd / A and chromaticity CIE (x, y) = (0.69, 0.30) was obtained. The voltage was 7.3V.
実施例４
ＩＴＯ透明導電膜を１５０ｎｍ堆積させたガラス基板（旭硝子（株）製、１５Ω／□、電子線ビーム法による形成品）を３０×４０ｍｍに切断、フォトリソグラフィ法によって３００μｍピッチ（残り幅２７０μｍ）×３２本のストライプ状にパターン加工した。ＩＴＯストライプの長辺方向片側は外部との電気的接続を容易にするために１．２７ｍｍピッチ（開口部幅８００μｍ）まで広げてある。得られた基板を”セミコクリン５６”、超純水で各々１５分間超音波洗浄してから乾燥させた。この基板を発光素子を作製する直前に１時間ＵＶ−オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が５×１０−４Ｐａ以下になるまで排気した。抵抗加熱法によって、まず正孔輸送性材料として４，４’−ビス（Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ）ビフェニル（αＮＰＤ）を６０ｎｍ蒸着した。次に、発光材料として、ホスト材料として化合物〔２〕を、ドーパント材料としてビス（２−フェニルキノリン）（アセチルアセトナト）イリジウム錯体をドープ濃度が１０％になるように３５ｎｍの厚さに蒸着した。次に電子輸送性材料として、１，３−ビス（１，１０−フェナントロリン−９−イル）ベンゼンを７５ｎｍの厚さに蒸着した。次に厚さ５０μｍのコバール板にウエットエッチングによって１６本の２５０μｍの開口部（残り幅５０μｍ、３００μｍピッチに相当）を設けたマスクを、真空中でＩＴＯストライプに直交するようにマスク交換し、マスクとＩＴＯ基板が密着するように裏面から磁石で固定した。そしてリチウムを０．５ｎｍ有機層にドーピングした後、アルミニウムを２００ｎｍ蒸着して３２×１６ドットマトリクス素子を作製した。本素子をマトリクス駆動させたところ、クロストークなく文字表示できた。
Example 4
A glass substrate (manufactured by Asahi Glass Co., Ltd., 15Ω / □, product formed by an electron beam method) on which an ITO transparent conductive film is deposited by 150 nm is cut into 30 × 40 mm, and 300 μm pitch (remaining width 270 μm) × 32 by photolithography. Patterned into strips of books. One side of the ITO stripe in the long side direction is expanded to a pitch of 1.27 mm (opening width 800 μm) in order to facilitate electrical connection with the outside. The obtained substrate was subjected to ultrasonic cleaning with “Semicocrine 56” and ultrapure water for 15 minutes, respectively, and then dried. This substrate was subjected to UV-ozone treatment for 1 hour immediately before producing the light-emitting element, placed in a vacuum vapor deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 × 10 −4 Pa or less. First, 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl (αNPD) was deposited as a hole transporting material by a resistance heating method to a thickness of 60 nm. Next, the compound [2] as a host material and a bis (2-phenylquinoline) (acetylacetonato) iridium complex as a dopant material were vapor-deposited to a thickness of 35 nm so as to have a doping concentration of 10%. . Next, 1,3-bis (1,10-phenanthroline-9-yl) benzene was deposited as an electron transporting material to a thickness of 75 nm. Next, the mask having 16 250 μm openings (corresponding to the remaining width of 50 μm and 300 μm pitch) formed by wet etching on a 50 μm thick Kovar plate was replaced in a vacuum so as to be orthogonal to the ITO stripe. And it fixed with the magnet from the back so that an ITO board | substrate might contact | adhere. And after doping lithium with a 0.5 nm organic layer, aluminum was vapor-deposited 200 nm, and the 32 * 16 dot matrix element was produced. When this element was driven in matrix, characters could be displayed without crosstalk.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006319658A JP2008135498A (en) | 2006-11-28 | 2006-11-28 | Light emitting element |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006319658A JP2008135498A (en) | 2006-11-28 | 2006-11-28 | Light emitting element |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2008135498A true JP2008135498A (en) | 2008-06-12 |
Family
ID=39560154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006319658A Pending JP2008135498A (en) | 2006-11-28 | 2006-11-28 | Light emitting element |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2008135498A (en) |
Cited By (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2161272A1 (en) | 2008-09-05 | 2010-03-10 | Basf Se | Phenanthrolines |
| JP2010140976A (en) * | 2008-12-10 | 2010-06-24 | Toyo Ink Mfg Co Ltd | Material for organic electroluminescent device, and organic electroluminescent device using the same |
| WO2011024451A1 (en) * | 2009-08-28 | 2011-03-03 | 保土谷化学工業株式会社 | Organic electroluminescent element and compound having carbazole ring structure |
| JP2011190239A (en) * | 2010-02-17 | 2011-09-29 | Chemiprokasei Kaisha Ltd | New bicarbazolyl derivative, host material comprising the same, and organic electroluminescent element using the same |
| WO2011132683A1 (en) | 2010-04-20 | 2011-10-27 | 出光興産株式会社 | Bis-carbazole derivative, material for organic electroluminescent element and organic electroluminescent element using same |
| JP2011231025A (en) * | 2010-04-26 | 2011-11-17 | Tosoh Corp | Biscarbazole compound and use thereof |
| WO2011155507A1 (en) * | 2010-06-08 | 2011-12-15 | 出光興産株式会社 | Organic electroluminescence element |
| WO2011155508A1 (en) * | 2010-06-08 | 2011-12-15 | 出光興産株式会社 | Organic electroluminescent element |
| WO2012029253A1 (en) | 2010-08-31 | 2012-03-08 | 出光興産株式会社 | Nitrogen-containing aromatic heterocyclic derivative and organic electroluminescence device using same |
| JP2012109638A (en) * | 2008-06-16 | 2012-06-07 | Toray Ind Inc | Device |
| WO2012086170A1 (en) | 2010-12-20 | 2012-06-28 | 出光興産株式会社 | Aromatic heterocycle derivative and organic electroluminescent element using same |
| WO2012090967A1 (en) | 2010-12-28 | 2012-07-05 | 出光興産株式会社 | Material for organic electroluminescent elements, and organic electroluminescent element using same |
| CN102597158A (en) * | 2009-11-03 | 2012-07-18 | 第一毛织株式会社 | Compound for organic photoelectric device and organic photoelectric device comprising same |
| WO2012108388A1 (en) | 2011-02-07 | 2012-08-16 | 出光興産株式会社 | Biscarbazole derivative and organic electroluminescent element using same |
| WO2012108389A1 (en) | 2011-02-07 | 2012-08-16 | 出光興産株式会社 | Biscarbazole derivative and organic electroluminescent element using same |
| WO2012128298A1 (en) | 2011-03-24 | 2012-09-27 | 出光興産株式会社 | Bis-carbazole derivative and organic electroluminescent element using same |
| US20120305900A1 (en) * | 2009-11-03 | 2012-12-06 | Hyung-Sun Kim | Compound for organic photoelectric device and organic photoelectric device including the same |
| WO2013024872A1 (en) | 2011-08-18 | 2013-02-21 | 出光興産株式会社 | Biscarbazole derivative and organic electroluminescence element using same |
| KR20130018724A (en) * | 2010-03-31 | 2013-02-25 | 이데미쓰 고산 가부시키가이샤 | Material for organic electroluminescent element, and organic electroluminescent element using same |
| EP2568030A2 (en) | 2010-05-03 | 2013-03-13 | Cheil Industries Inc. | Compound for organic optoelectronic device, organic light emitting diode including same, and display device including organic light emitting diode |
| US20130140549A1 (en) * | 2010-08-20 | 2013-06-06 | Universal Display Corporation | Bicarbazole compounds for oleds |
| WO2013122082A1 (en) * | 2012-02-15 | 2013-08-22 | 東レ株式会社 | Light-emitting element material, and light-emitting element |
| KR20130094222A (en) | 2010-06-24 | 2013-08-23 | 도레이 카부시키가이샤 | Light-emitting device material and light-emitting device |
| WO2014007022A1 (en) * | 2012-07-06 | 2014-01-09 | 東レ株式会社 | Light emitting element material and light emitting element |
| JP2014505678A (en) * | 2010-12-21 | 2014-03-06 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Novel organic electroluminescent compound and organic electroluminescent device using the same |
| CN103904227A (en) * | 2012-12-27 | 2014-07-02 | 三星显示有限公司 | Organic light-emitting diode |
| KR101431644B1 (en) * | 2009-08-10 | 2014-08-21 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescent compounds and organic electroluminescent devices containing them |
| JP2014157947A (en) * | 2013-02-15 | 2014-08-28 | Idemitsu Kosan Co Ltd | Organic electroluminescence device and electronic device |
| CN104119264A (en) * | 2013-04-25 | 2014-10-29 | 海洋王照明科技股份有限公司 | Organic semiconductor material, preparation method thereof and electroluminescent device |
| KR20140148368A (en) | 2012-03-26 | 2014-12-31 | 도레이 카부시키가이샤 | Material for luminescent element, and luminescent element |
| JP2015526886A (en) * | 2012-06-14 | 2015-09-10 | ユニバーサル ディスプレイ コーポレイション | Biscarbazole derivative host material and red light emitter for OLED light emitting region |
| US9287512B2 (en) | 2011-03-08 | 2016-03-15 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compounds, layers and organic electroluminescent device using the same |
| CN105720203A (en) * | 2014-12-19 | 2016-06-29 | 三星显示有限公司 | Organic light-emitting device |
| TWI548628B (en) * | 2011-05-26 | 2016-09-11 | 第一毛織股份有限公司 | Compound for organic photoelectric element, organic light emitting diode comprising the same, and display comprising the organic light emitting diode |
| CN106410054A (en) * | 2015-12-09 | 2017-02-15 | 广东阿格蕾雅光电材料有限公司 | Cavity-only organic semiconductor diode device |
| US20170117488A1 (en) * | 2014-04-08 | 2017-04-27 | Rohm And Haas Electronic Materials Korea Ltd. | Multi-component host material and organic electroluminescent device comprising the same |
| TWI583772B (en) * | 2011-02-11 | 2017-05-21 | 環球顯示器公司 | Organic light emitting device and materials for use in same |
| US20170213968A1 (en) * | 2014-07-22 | 2017-07-27 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent device |
| US20190019972A1 (en) * | 2011-10-26 | 2019-01-17 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence element, and material for organic electroluminescence element |
| US10297756B2 (en) | 2012-12-27 | 2019-05-21 | Samsung Display Co., Ltd. | Organic light-emitting diode |
| JP2021061316A (en) * | 2019-10-07 | 2021-04-15 | 三菱ケミカル株式会社 | Composition for organic electroluminescent element, organic electroluminescent element, display device, and lighting device |
| US11038113B2 (en) | 2014-11-19 | 2021-06-15 | Samsung Display Co., Ltd. | Organic light-emitting device |
| JP2021528379A (en) * | 2018-06-22 | 2021-10-21 | エルティー・マテリアルズ・カンパニー・リミテッドＬＴ Ｍａｔｅｒｉａｌｓ Ｃｏ．， Ｌｔｄ． | A heterocyclic compound, an organic light emitting device containing the heterocyclic compound, a composition for an organic material layer of the organic light emitting device, and a method for producing the organic light emitting device. |
| WO2022131123A1 (en) | 2020-12-18 | 2022-06-23 | 日鉄ケミカル＆マテリアル株式会社 | Organic electroluminescent element and method for manufacturing same |
| WO2022149493A1 (en) | 2021-01-08 | 2022-07-14 | 日鉄ケミカル＆マテリアル株式会社 | Organic electroluminescent element and method for producing same |
| US20230143281A1 (en) * | 2020-03-27 | 2023-05-11 | Semiconductor Energy Laboratory Co., Ltd. | Composition for light-emitting device, light-emitting device, light-emitting apparatus, electronic device, and lighting device |
| US11812626B2 (en) | 2011-02-16 | 2023-11-07 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element |
| US11871592B2 (en) | 2011-03-23 | 2024-01-09 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element |
| US12100795B2 (en) | 2011-02-16 | 2024-09-24 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element |
-
2006
- 2006-11-28 JP JP2006319658A patent/JP2008135498A/en active Pending
Cited By (130)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012109638A (en) * | 2008-06-16 | 2012-06-07 | Toray Ind Inc | Device |
| JP2013012503A (en) * | 2008-06-16 | 2013-01-17 | Toray Ind Inc | Device |
| EP2161272A1 (en) | 2008-09-05 | 2010-03-10 | Basf Se | Phenanthrolines |
| JP2010140976A (en) * | 2008-12-10 | 2010-06-24 | Toyo Ink Mfg Co Ltd | Material for organic electroluminescent device, and organic electroluminescent device using the same |
| KR101431644B1 (en) * | 2009-08-10 | 2014-08-21 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescent compounds and organic electroluminescent devices containing them |
| JPWO2011024451A1 (en) * | 2009-08-28 | 2013-01-24 | 保土谷化学工業株式会社 | Compound having carbazole ring structure and organic electroluminescence device |
| WO2011024451A1 (en) * | 2009-08-28 | 2011-03-03 | 保土谷化学工業株式会社 | Organic electroluminescent element and compound having carbazole ring structure |
| US9732036B2 (en) * | 2009-08-28 | 2017-08-15 | Hodogaya Chemical Co., Ltd. | Compound having carbazole ring structure, and organic electroluminescent device |
| US20120175599A1 (en) * | 2009-08-28 | 2012-07-12 | Hodogaya Chemical Co., Ltd. | Compound having carbazole ring structure, and organic electroluminescent device |
| KR101853143B1 (en) * | 2009-08-28 | 2018-04-27 | 호도가야 가가쿠 고교 가부시키가이샤 | Organic electroluminescent element and compound having carbazole ring structure |
| CN102482216A (en) * | 2009-08-28 | 2012-05-30 | 保土谷化学工业株式会社 | Organic electroluminescent element and compound having carbazole ring structure |
| EP3460024A1 (en) * | 2009-11-03 | 2019-03-27 | Cheil Industries Inc. | Compound for an organic photoelectric device, and organic photoelectric device comprising same |
| EP2497811A4 (en) * | 2009-11-03 | 2013-09-11 | Cheil Ind Inc | CONNECTION FOR AN ORGANIC PHOTOELECTRIC DEVICE AND ORGANIC PHOTOELECTRIC DEVICE THEREFOR |
| CN105670610B (en) * | 2009-11-03 | 2019-03-19 | 第一毛织株式会社 | The compound of organic photoelectric device and organic photoelectric device comprising the compound |
| US20120305900A1 (en) * | 2009-11-03 | 2012-12-06 | Hyung-Sun Kim | Compound for organic photoelectric device and organic photoelectric device including the same |
| US8828561B2 (en) | 2009-11-03 | 2014-09-09 | Cheil Industries, Inc. | Compound for organic photoelectric device and organic photoelectric device including the same |
| CN102597158A (en) * | 2009-11-03 | 2012-07-18 | 第一毛织株式会社 | Compound for organic photoelectric device and organic photoelectric device comprising same |
| US9478755B2 (en) | 2009-11-03 | 2016-10-25 | Cheil Industries, Inc. | Compound for organic photoelectric device and organic photoelectric device including the same |
| US9450193B2 (en) | 2009-11-03 | 2016-09-20 | Samsung Sdi Co., Ltd. | Compound for organic photoelectric device and organic photoelectric device including the same |
| EP2497811A2 (en) | 2009-11-03 | 2012-09-12 | Cheil Industries Inc. | Compound for an organic photoelectric device, and organic photoelectric device comprising same |
| CN105670610A (en) * | 2009-11-03 | 2016-06-15 | 第一毛织株式会社 | Compound for an organic photoelectric device, and organic photoelectric device comprising same |
| JP2011190239A (en) * | 2010-02-17 | 2011-09-29 | Chemiprokasei Kaisha Ltd | New bicarbazolyl derivative, host material comprising the same, and organic electroluminescent element using the same |
| KR20130018724A (en) * | 2010-03-31 | 2013-02-25 | 이데미쓰 고산 가부시키가이샤 | Material for organic electroluminescent element, and organic electroluminescent element using same |
| KR101891353B1 (en) * | 2010-03-31 | 2018-08-23 | 이데미쓰 고산 가부시키가이샤 | Material for organic electroluminescent element, and organic electroluminescent element using same |
| US10193077B2 (en) | 2010-04-20 | 2019-01-29 | Idemitsu Kosan Co., Ltd. | Biscarbazole derivative, material for organic electroluminescence device and organic electroluminescence device using the same |
| CN104592206A (en) * | 2010-04-20 | 2015-05-06 | 出光兴产株式会社 | Bicarbazole derivative, material for organic electroluminescent element, and organic electroluminescent element using same |
| CN102421772A (en) * | 2010-04-20 | 2012-04-18 | 出光兴产株式会社 | Biscarbazole derivative, material for organic electroluminescent device, and organic electroluminescent device using same |
| JP2013030781A (en) * | 2010-04-20 | 2013-02-07 | Idemitsu Kosan Co Ltd | Organic electroluminescent element |
| EP2423209A4 (en) * | 2010-04-20 | 2013-02-13 | Idemitsu Kosan Co | BIS-CARBAZOLE DERIVATIVE, MATERIAL FOR ORGANIC ELECTROLUMINESCENT ELEMENT, AND ORGANIC ELECTROLUMINESCENT ELEMENT USING THE SAME |
| EP2415769A4 (en) * | 2010-04-20 | 2013-02-13 | Idemitsu Kosan Co | BIS-CARBAZOLE DERIVATIVE, MATERIAL FOR ORGANIC ELECTROLUMINESCENT ELEMENT, AND ORGANIC ELECTROLUMINESCENT ELEMENT USING THE SAME |
| CN102421772B (en) * | 2010-04-20 | 2015-11-25 | 出光兴产株式会社 | Bicarbazole derivative, material for organic electroluminescent element, and organic electroluminescent element using same |
| US8652654B2 (en) | 2010-04-20 | 2014-02-18 | Idemitsu Kosan Co., Ltd. | Biscarbazole derivative, material for organic electroluminescence device and organic electroluminescence device using the same |
| EP2423209A1 (en) | 2010-04-20 | 2012-02-29 | Idemitsu Kosan Co., Ltd. | Bis-carbazole derivative, material for organic electroluminescent element and organic electroluminescent element using same |
| CN102439004A (en) * | 2010-04-20 | 2012-05-02 | 出光兴产株式会社 | Biscarbazole derivative, material for organic electroluminescent device, and organic electroluminescent device using same |
| US8940414B2 (en) | 2010-04-20 | 2015-01-27 | Idemitsu Kosan Co., Ltd. | Biscarbazole derivative, material for organic electroluminescence device and organic electroluminescence device using the same |
| US8877352B2 (en) | 2010-04-20 | 2014-11-04 | Idemitsu Kosan Co., Ltd. | Biscarbazole derivative, material for organic electroluminescence device and organic electroluminescence device using the same |
| US8865323B2 (en) | 2010-04-20 | 2014-10-21 | Idemitsu Kosan Co., Ltd. | Biscarbazole derivative, material for organic electroluminescence device and organic electroluminescence device using the same |
| KR101441177B1 (en) * | 2010-04-20 | 2014-09-17 | 이데미쓰 고산 가부시키가이샤 | Organic electroluminescent element using bis-carbazole derivative |
| EP2415769A1 (en) | 2010-04-20 | 2012-02-08 | Idemitsu Kosan Co., Ltd. | Bis-carbazole derivative, material for organic electroluminescent element and organic electroluminescent element using same |
| KR101421365B1 (en) | 2010-04-20 | 2014-07-18 | 이데미쓰 고산 가부시키가이샤 | Bis-carbazole derivative, material for organic electroluminescent element and organic electroluminescent element using same |
| WO2011132683A1 (en) | 2010-04-20 | 2011-10-27 | 出光興産株式会社 | Bis-carbazole derivative, material for organic electroluminescent element and organic electroluminescent element using same |
| JP5562970B2 (en) * | 2010-04-20 | 2014-07-30 | 出光興産株式会社 | Biscarbazole derivative, material for organic electroluminescence device, and organic electroluminescence device using the same |
| JP2011231025A (en) * | 2010-04-26 | 2011-11-17 | Tosoh Corp | Biscarbazole compound and use thereof |
| EP2568030A2 (en) | 2010-05-03 | 2013-03-13 | Cheil Industries Inc. | Compound for organic optoelectronic device, organic light emitting diode including same, and display device including organic light emitting diode |
| US9543530B2 (en) | 2010-05-03 | 2017-01-10 | Cheil Industries, Inc. | Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode |
| EP2568030B1 (en) * | 2010-05-03 | 2019-12-25 | Cheil Industries Inc. | Compound for organic optoelectronic device, organic light emitting diode including same, and display device including organic light emitting diode |
| CN102971395A (en) * | 2010-05-03 | 2013-03-13 | 第一毛织株式会社 | Compound for organic optoelectronic device, organic light emitting diode comprising same, and display comprising same |
| JP2013533604A (en) * | 2010-05-03 | 2013-08-22 | チェイル インダストリーズ インコーポレイテッド | Compound for organic optoelectronic device, organic light emitting diode including the same, and display device including the organic light emitting diode |
| WO2011155508A1 (en) * | 2010-06-08 | 2011-12-15 | 出光興産株式会社 | Organic electroluminescent element |
| WO2011155507A1 (en) * | 2010-06-08 | 2011-12-15 | 出光興産株式会社 | Organic electroluminescence element |
| US8987715B2 (en) | 2010-06-08 | 2015-03-24 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence element |
| KR20130094222A (en) | 2010-06-24 | 2013-08-23 | 도레이 카부시키가이샤 | Light-emitting device material and light-emitting device |
| JP2013536196A (en) * | 2010-08-20 | 2013-09-19 | ユニバーサル ディスプレイ コーポレイション | Bicarbazole compounds for OLED |
| US11316113B2 (en) | 2010-08-20 | 2022-04-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US12464945B2 (en) | 2010-08-20 | 2025-11-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20130140549A1 (en) * | 2010-08-20 | 2013-06-06 | Universal Display Corporation | Bicarbazole compounds for oleds |
| US9954180B2 (en) | 2010-08-20 | 2018-04-24 | Universal Display Corporation | Bicarbazole compounds for OLEDs |
| US20120181524A1 (en) * | 2010-08-31 | 2012-07-19 | Idemitsu Kosan Co., Ltd. | Nitrogen-containing aromatic heterocyclic derivative and organic electroluminescence device using the same |
| WO2012029253A1 (en) | 2010-08-31 | 2012-03-08 | 出光興産株式会社 | Nitrogen-containing aromatic heterocyclic derivative and organic electroluminescence device using same |
| US9382206B2 (en) | 2010-08-31 | 2016-07-05 | Idemitsu Kosan Co., Ltd. | Nitrogen-containing aromatic heterocyclic derivative and organic electroluminescence device using the same |
| KR20130130747A (en) | 2010-12-20 | 2013-12-02 | 이데미쓰 고산 가부시키가이샤 | Aromatic heterocycle derivative and organic electroluminescent element using same |
| US9705091B2 (en) | 2010-12-20 | 2017-07-11 | Idemitsu Kosan Co., Ltd. | Aromatic heterocycle derivative and organic electroluminescent element using same |
| WO2012086170A1 (en) | 2010-12-20 | 2012-06-28 | 出光興産株式会社 | Aromatic heterocycle derivative and organic electroluminescent element using same |
| KR101478000B1 (en) * | 2010-12-21 | 2015-01-05 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| JP2014505678A (en) * | 2010-12-21 | 2014-03-06 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Novel organic electroluminescent compound and organic electroluminescent device using the same |
| US9923151B2 (en) | 2010-12-28 | 2018-03-20 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescent elements, and organic electroluminescent element using same |
| KR20140015285A (en) | 2010-12-28 | 2014-02-06 | 이데미쓰 고산 가부시키가이샤 | Material for organic electroluminescent elements, and organic electroluminescent element using same |
| WO2012090967A1 (en) | 2010-12-28 | 2012-07-05 | 出光興産株式会社 | Material for organic electroluminescent elements, and organic electroluminescent element using same |
| US10230057B2 (en) | 2011-02-07 | 2019-03-12 | Idemitsu Kosan Co., Ltd. | Biscarbazole derivatives and organic electroluminescence device employing the same |
| US10147888B2 (en) | 2011-02-07 | 2018-12-04 | Idemitsu Kosan Co., Ltd. | Biscarbazole derivative and organic electroluminescent element using same |
| CN103347857A (en) * | 2011-02-07 | 2013-10-09 | 出光兴产株式会社 | Biscarbazole derivative and organic electroluminescent element using same |
| US10147889B2 (en) | 2011-02-07 | 2018-12-04 | Idemitsu Kosan Co., Ltd. | Biscarbazole derivative and organic electroluminescent element using same |
| US9818958B2 (en) | 2011-02-07 | 2017-11-14 | Idemitsu Kosan Co., Ltd. | Biscarbazole derivatives and organic electroluminescence device employing the same |
| US9373802B2 (en) | 2011-02-07 | 2016-06-21 | Idemitsu Kosan Co., Ltd. | Biscarbazole derivatives and organic electroluminescence device employing the same |
| KR20150061022A (en) | 2011-02-07 | 2015-06-03 | 이데미쓰 고산 가부시키가이샤 | Biscarbazole derivative and organic electroluminescent element using same |
| JP2015180642A (en) * | 2011-02-07 | 2015-10-15 | 出光興産株式会社 | Bis carbazole derivative, and organic electroluminescent element using the same |
| JP2016138132A (en) * | 2011-02-07 | 2016-08-04 | 出光興産株式会社 | Bis carbazole derivative, and organic electroluminescent element using the same |
| CN103347857B (en) * | 2011-02-07 | 2016-08-10 | 出光兴产株式会社 | Biscarbazole derivative and organic electroluminescent element using same |
| US11271171B2 (en) | 2011-02-07 | 2022-03-08 | Idemitsu Kosan Co., Ltd. | Biscarbazole derivative and organic electroluminescent element using same |
| WO2012108389A1 (en) | 2011-02-07 | 2012-08-16 | 出光興産株式会社 | Biscarbazole derivative and organic electroluminescent element using same |
| TWI550059B (en) * | 2011-02-07 | 2016-09-21 | Idemitsu Kosan Co | A double carbazole derivative and an organic electroluminescent element using the same |
| WO2012108388A1 (en) | 2011-02-07 | 2012-08-16 | 出光興産株式会社 | Biscarbazole derivative and organic electroluminescent element using same |
| US8803134B2 (en) | 2011-02-07 | 2014-08-12 | Idemitsu Kosan Co., Ltd. | Biscarbazole derivatives and organic electroluminescence |
| KR20140037814A (en) | 2011-02-07 | 2014-03-27 | 이데미쓰 고산 가부시키가이샤 | Biscarbazole derivative and organic electroluminescent element using same |
| TWI583772B (en) * | 2011-02-11 | 2017-05-21 | 環球顯示器公司 | Organic light emitting device and materials for use in same |
| US11812626B2 (en) | 2011-02-16 | 2023-11-07 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element |
| US12100795B2 (en) | 2011-02-16 | 2024-09-24 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element |
| US12150325B2 (en) | 2011-02-16 | 2024-11-19 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element |
| US9287512B2 (en) | 2011-03-08 | 2016-03-15 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compounds, layers and organic electroluminescent device using the same |
| US11871592B2 (en) | 2011-03-23 | 2024-01-09 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element |
| JPWO2012128298A1 (en) * | 2011-03-24 | 2014-07-24 | 出光興産株式会社 | Biscarbazole derivative and organic electroluminescence device using the same |
| WO2012128298A1 (en) | 2011-03-24 | 2012-09-27 | 出光興産株式会社 | Bis-carbazole derivative and organic electroluminescent element using same |
| US9564595B2 (en) | 2011-03-24 | 2017-02-07 | Idemitsu Kosan Co., Ltd. | Bis-carbazole derivative and organic electroluminescent element using same |
| TWI548628B (en) * | 2011-05-26 | 2016-09-11 | 第一毛織股份有限公司 | Compound for organic photoelectric element, organic light emitting diode comprising the same, and display comprising the organic light emitting diode |
| KR20140050045A (en) | 2011-08-18 | 2014-04-28 | 이데미쓰 고산 가부시키가이샤 | Biscarbazole derivative and organic electroluminescence element using same |
| JPWO2013024872A1 (en) * | 2011-08-18 | 2015-03-05 | 出光興産株式会社 | Biscarbazole derivative and organic electroluminescence device using the same |
| WO2013024872A1 (en) | 2011-08-18 | 2013-02-21 | 出光興産株式会社 | Biscarbazole derivative and organic electroluminescence element using same |
| US10707434B2 (en) * | 2011-10-26 | 2020-07-07 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence element, and material for organic electroluminescence element |
| US20190019972A1 (en) * | 2011-10-26 | 2019-01-17 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence element, and material for organic electroluminescence element |
| US9627625B2 (en) | 2012-02-15 | 2017-04-18 | Toray Industries, Inc. | Light-emitting device material and light-emitting device |
| WO2013122082A1 (en) * | 2012-02-15 | 2013-08-22 | 東レ株式会社 | Light-emitting element material, and light-emitting element |
| KR20140148368A (en) | 2012-03-26 | 2014-12-31 | 도레이 카부시키가이샤 | Material for luminescent element, and luminescent element |
| JP2015526886A (en) * | 2012-06-14 | 2015-09-10 | ユニバーサル ディスプレイ コーポレイション | Biscarbazole derivative host material and red light emitter for OLED light emitting region |
| WO2014007022A1 (en) * | 2012-07-06 | 2014-01-09 | 東レ株式会社 | Light emitting element material and light emitting element |
| CN103904227A (en) * | 2012-12-27 | 2014-07-02 | 三星显示有限公司 | Organic light-emitting diode |
| US20140183466A1 (en) * | 2012-12-27 | 2014-07-03 | Samsung Display Co., Ltd. | Organic light-emitting diode |
| US9590184B2 (en) * | 2012-12-27 | 2017-03-07 | Samsung Display Co., Ltd. | Organic light-emitting diode |
| US10297756B2 (en) | 2012-12-27 | 2019-05-21 | Samsung Display Co., Ltd. | Organic light-emitting diode |
| USRE47763E1 (en) | 2013-02-15 | 2019-12-10 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and electronic device |
| USRE49237E1 (en) | 2013-02-15 | 2022-10-04 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and electronic device |
| JP2014157947A (en) * | 2013-02-15 | 2014-08-28 | Idemitsu Kosan Co Ltd | Organic electroluminescence device and electronic device |
| CN104119264A (en) * | 2013-04-25 | 2014-10-29 | 海洋王照明科技股份有限公司 | Organic semiconductor material, preparation method thereof and electroluminescent device |
| US20170117488A1 (en) * | 2014-04-08 | 2017-04-27 | Rohm And Haas Electronic Materials Korea Ltd. | Multi-component host material and organic electroluminescent device comprising the same |
| US12402531B2 (en) | 2014-04-08 | 2025-08-26 | Dupont Specialty Materials Korea Ltd. | Multi-component host material and organic electroluminescent device comprising the same |
| US20170213968A1 (en) * | 2014-07-22 | 2017-07-27 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent device |
| US11038113B2 (en) | 2014-11-19 | 2021-06-15 | Samsung Display Co., Ltd. | Organic light-emitting device |
| CN105720203A (en) * | 2014-12-19 | 2016-06-29 | 三星显示有限公司 | Organic light-emitting device |
| US10978643B2 (en) * | 2014-12-19 | 2021-04-13 | Samsung Display Co., Ltd. | Organic light-emitting device |
| CN106410054B (en) * | 2015-12-09 | 2019-03-12 | 广东阿格蕾雅光电材料有限公司 | Hole-Only Organic Semiconductor Diode Devices |
| CN106410054A (en) * | 2015-12-09 | 2017-02-15 | 广东阿格蕾雅光电材料有限公司 | Cavity-only organic semiconductor diode device |
| JP7479697B2 (en) | 2018-06-22 | 2024-05-09 | エルティー・マテリアルズ・カンパニー・リミテッド | Heterocyclic compound, organic light-emitting device containing the same, composition for organic layer of organic light-emitting device, and method for producing organic light-emitting device |
| US12018022B2 (en) | 2018-06-22 | 2024-06-25 | Lt Materials Co., Ltd. | Heterocyclic compound, organic light emitting diode comprising same, composition for organic layer of organic light emitting diode, and method for manufacturing organic light emitting diode |
| JP2021528379A (en) * | 2018-06-22 | 2021-10-21 | エルティー・マテリアルズ・カンパニー・リミテッドＬＴ Ｍａｔｅｒｉａｌｓ Ｃｏ．， Ｌｔｄ． | A heterocyclic compound, an organic light emitting device containing the heterocyclic compound, a composition for an organic material layer of the organic light emitting device, and a method for producing the organic light emitting device. |
| JP7276059B2 (en) | 2019-10-07 | 2023-05-18 | 三菱ケミカル株式会社 | Composition for organic electroluminescent device, organic electroluminescent device, display device and lighting device |
| JP2021061316A (en) * | 2019-10-07 | 2021-04-15 | 三菱ケミカル株式会社 | Composition for organic electroluminescent element, organic electroluminescent element, display device, and lighting device |
| US20230143281A1 (en) * | 2020-03-27 | 2023-05-11 | Semiconductor Energy Laboratory Co., Ltd. | Composition for light-emitting device, light-emitting device, light-emitting apparatus, electronic device, and lighting device |
| KR20230121083A (en) | 2020-12-18 | 2023-08-17 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | Organic electroluminescent device and manufacturing method thereof |
| WO2022131123A1 (en) | 2020-12-18 | 2022-06-23 | 日鉄ケミカル＆マテリアル株式会社 | Organic electroluminescent element and method for manufacturing same |
| KR20230129396A (en) | 2021-01-08 | 2023-09-08 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | Organic electroluminescent device and method of manufacturing the same |
| WO2022149493A1 (en) | 2021-01-08 | 2022-07-14 | 日鉄ケミカル＆マテリアル株式会社 | Organic electroluminescent element and method for producing same |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2008135498A (en) | Light emitting element | |
| JP5565494B2 (en) | Light emitting element | |
| JP4725056B2 (en) | Light emitting device material and light emitting device | |
| JP5532705B2 (en) | Light emitting element | |
| JP4254231B2 (en) | Light emitting device material and light emitting device using the same | |
| KR101540637B1 (en) | Light-emitting device | |
| JP2006073581A5 (en) | ||
| JP2004200162A (en) | Light emitting element | |
| JP2001267080A (en) | Light emission element | |
| KR101204132B1 (en) | Material for light-emitting element and light-emitting element | |
| WO2010084852A1 (en) | Light-emitting element material and light-emitting element | |
| JP2009246354A (en) | Light emitting element | |
| JP5267123B2 (en) | Light emitting element | |
| JP2010027761A (en) | Light emitting element | |
| JP2005093425A (en) | Light emitting device | |
| JP5076328B2 (en) | Light emitting element | |
| JP5640460B2 (en) | Light emitting device and light emitting device material | |
| JP2011204843A (en) | Light-emitting element | |
| JP2010056190A (en) | Light-emitting element | |
| JP2009010181A (en) | Light emitting device | |
| JP2007194241A (en) | Light emitting device | |
| JP2001250689A (en) | Light emission element | |
| JP2007131723A (en) | Electroluminescent element material and electroluminescent element | |
| JP2003109768A (en) | Light emitting element | |
| JP2005154534A (en) | Light emitting device material and light emitting device using the same |