TW201806942A - 哌啶衍生物、液晶組成物和液晶顯示元件 - Google Patents
哌啶衍生物、液晶組成物和液晶顯示元件 Download PDFInfo
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- TW201806942A TW201806942A TW106129135A TW106129135A TW201806942A TW 201806942 A TW201806942 A TW 201806942A TW 106129135 A TW106129135 A TW 106129135A TW 106129135 A TW106129135 A TW 106129135A TW 201806942 A TW201806942 A TW 201806942A
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- diyl
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- liquid crystal
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- 239000000203 mixture Substances 0.000 title claims abstract description 232
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 146
- 150000003053 piperidines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 374
- 239000000654 additive Substances 0.000 claims abstract description 45
- 230000000996 additive effect Effects 0.000 claims abstract description 26
- -1 naphthalene-1,2-diyl Chemical group 0.000 claims description 134
- 239000001257 hydrogen Substances 0.000 claims description 81
- 229910052739 hydrogen Inorganic materials 0.000 claims description 81
- 239000011737 fluorine Substances 0.000 claims description 70
- 229910052731 fluorine Inorganic materials 0.000 claims description 70
- 239000000460 chlorine Substances 0.000 claims description 60
- 229910052801 chlorine Inorganic materials 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 55
- 125000004432 carbon atom Chemical group C* 0.000 claims description 46
- 125000001153 fluoro group Chemical group F* 0.000 claims description 45
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
- 125000002947 alkylene group Chemical group 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 238000006467 substitution reaction Methods 0.000 claims description 9
- 125000005699 methyleneoxy group Chemical group [H]C([H])([*:1])O[*:2] 0.000 claims description 7
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 claims description 6
- 239000011159 matrix material Substances 0.000 claims description 5
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000005453 2,5-difluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C(F)=C([H])C([*:2])=C1F 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims description 2
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- 238000006243 chemical reaction Methods 0.000 claims description 2
- 230000005684 electric field Effects 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 abstract description 18
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- 230000000052 comparative effect Effects 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- AQAGCHUHSHTBLP-AFBJXSTISA-N (4z,8z,13z)-11-hexyl-1-oxacyclopentadeca-4,8,13-trien-2-one Chemical compound CCCCCCC1C\C=C/CC\C=C/CC(=O)OC\C=C/C1 AQAGCHUHSHTBLP-AFBJXSTISA-N 0.000 description 11
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
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- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000004642 Polyimide Substances 0.000 description 4
- 239000004990 Smectic liquid crystal Substances 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
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- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 4
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
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- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 2
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- 125000006023 1-pentenyl group Chemical group 0.000 description 2
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
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- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- NWHNXXMYEICZAT-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-ol Chemical compound CN1C(C)(C)CC(O)CC1(C)C NWHNXXMYEICZAT-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920003216 poly(methylphenylsiloxane) Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal Substances (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016166473 | 2016-08-29 | ||
| JP2016-166473 | 2016-08-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201806942A true TW201806942A (zh) | 2018-03-01 |
Family
ID=57835065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW106129135A TW201806942A (zh) | 2016-08-29 | 2017-08-28 | 哌啶衍生物、液晶組成物和液晶顯示元件 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP6690647B2 (fr) |
| KR (1) | KR102576757B1 (fr) |
| CN (1) | CN109641839B (fr) |
| TW (1) | TW201806942A (fr) |
| WO (1) | WO2017014326A2 (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5196073B2 (ja) | 2010-12-24 | 2013-05-15 | Ｄｉｃ株式会社 | 重合性化合物含有液晶組成物及びそれを使用した液晶表示素子 |
| JP2018123296A (ja) * | 2017-02-01 | 2018-08-09 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
| CN108373923A (zh) * | 2017-02-01 | 2018-08-07 | 捷恩智株式会社 | 液晶组合物及其用途、液晶显示元件及高分子稳定取向型液晶显示元件 |
| JP6787202B2 (ja) * | 2017-03-21 | 2020-11-18 | 東洋インキＳｃホールディングス株式会社 | 活性エネルギー線重合性組成物 |
| WO2018235713A1 (fr) * | 2017-06-23 | 2018-12-27 | Dic株式会社 | Composition de cristaux liquides, et élément d'affichage à cristaux liquides mettant en œuvre celle-ci |
| KR102719617B1 (ko) * | 2018-12-17 | 2024-10-17 | 주식회사 동진쎄미켐 | 반응성 광 안정제 화합물 및 이를 포함하는 액정 조성물 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2755340A1 (de) * | 1976-12-23 | 1978-06-29 | Ciba Geigy Ag | Neue polyalkylpiperidinderivate |
| JPS60226553A (ja) * | 1984-04-24 | 1985-11-11 | Sumitomo Chem Co Ltd | 安定化合成樹脂組成物 |
| IT1214600B (it) * | 1985-04-22 | 1990-01-18 | Ciba Geigy Spa | Composti piperidinici utilizzabili come stabilizzanti per polimeri sintetici. |
| WO1991003511A1 (fr) * | 1989-09-09 | 1991-03-21 | Sandoz Ltd | Polyamides synthetiques et leurs sels |
| IT1240690B (it) * | 1990-04-30 | 1993-12-17 | Ciba Geigy Ag | Composti piperdin-triazinici atti all'impiego come stabilizzanti per materiali organici |
| JPH05271190A (ja) * | 1992-03-24 | 1993-10-19 | Mitsubishi Petrochem Co Ltd | アミン化合物 |
| IT1256636B (it) * | 1992-12-10 | 1995-12-12 | Ciba Geigy Spa | Processo per la preparazione di 2,2,6,6-tetrametil-4- piperidilossi-1,3,5-triazine contenenti due o piu' anelli triazinici |
| IT1264945B1 (it) * | 1993-07-16 | 1996-10-17 | Ciba Geigy Spa | Composti piperidinici atti all'impiego come stabilizzanti per materiali organici |
| US20090069470A1 (en) * | 2004-11-02 | 2009-03-12 | Markus Frey | Process for the synthesis of n-alkoxyamines |
| ES2435468T3 (es) * | 2009-02-04 | 2013-12-19 | Basf Se | Estabilizadores macrocíclicos de triazina-HALS N-sustituidos |
| CN101591331B (zh) * | 2009-06-25 | 2014-05-21 | 中国乐凯胶片集团公司 | 一种受阻胺光稳定剂的制备方法 |
| EP2630137B1 (fr) * | 2010-10-20 | 2015-04-01 | Basf Se | Photostabilisants à base d'amines affichant un encombrement stérique à fonctionnalisation mixte |
| KR20220043248A (ko) | 2010-12-07 | 2022-04-05 | 메르크 파텐트 게엠베하 | 액정 매질 및 전기-광학 디스플레이 |
| EP2722381B1 (fr) | 2012-10-18 | 2018-01-03 | Merck Patent GmbH | Fluide à base de cristaux liquides, son procédé de stabilisation et affichage à base de cristaux liquides |
| JP6402907B2 (ja) * | 2014-09-24 | 2018-10-10 | Jnc株式会社 | ピペリジン誘導体、液晶組成物および液晶表示素子 |
| MX2016000701A (es) * | 2015-01-22 | 2016-11-24 | Evonik Degussa Gmbh | Proceso para preparar un compuesto de triacetonamina n-metil sustituida. |
| GB2539908B (en) * | 2015-06-30 | 2018-06-27 | Merck Patent Gmbh | Process for the stabilisation of liquid crystal media |
-
2016
- 2016-11-16 KR KR1020197000983A patent/KR102576757B1/ko active Active
- 2016-11-16 JP JP2017529958A patent/JP6690647B2/ja active Active
- 2016-11-16 CN CN201680088635.9A patent/CN109641839B/zh active Active
- 2016-11-16 WO PCT/JP2016/084013 patent/WO2017014326A2/fr not_active Ceased
-
2017
- 2017-08-28 TW TW106129135A patent/TW201806942A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20190046760A (ko) | 2019-05-07 |
| CN109641839B (zh) | 2022-07-01 |
| WO2017014326A3 (fr) | 2017-03-16 |
| CN109641839A (zh) | 2019-04-16 |
| KR102576757B1 (ko) | 2023-09-07 |
| WO2017014326A2 (fr) | 2017-01-26 |
| JP6690647B2 (ja) | 2020-04-28 |
| JPWO2017014326A1 (ja) | 2019-06-27 |
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