JP2005255981A5 - - Google Patents
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- Publication number
- JP2005255981A5 JP2005255981A5 JP2005015202A JP2005015202A JP2005255981A5 JP 2005255981 A5 JP2005255981 A5 JP 2005255981A5 JP 2005015202 A JP2005015202 A JP 2005015202A JP 2005015202 A JP2005015202 A JP 2005015202A JP 2005255981 A5 JP2005255981 A5 JP 2005255981A5
- Authority
- JP
- Japan
- Prior art keywords
- replaced
- alkyl
- hydrogen
- carbon atoms
- fluorine
- 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.)
- Granted
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- -1 aminophenyl group Chemical group 0.000 claims description 121
- 125000000217 alkyl group Chemical group 0.000 claims description 116
- 229910052739 hydrogen Inorganic materials 0.000 claims description 96
- 239000001257 hydrogen Substances 0.000 claims description 96
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 94
- 125000004432 carbon atom Chemical group C* 0.000 claims description 93
- 229910052731 fluorine Inorganic materials 0.000 claims description 81
- 239000011737 fluorine Substances 0.000 claims description 81
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 69
- 125000002947 alkylene group Chemical group 0.000 claims description 59
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 37
- 150000004985 diamines Chemical class 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 23
- 125000003277 amino group Chemical group 0.000 claims description 23
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 239000004973 liquid crystal related substance Substances 0.000 claims description 15
- 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 12
- 230000008878 coupling Effects 0.000 claims description 12
- 238000010168 coupling process Methods 0.000 claims description 12
- 238000005859 coupling reaction Methods 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 12
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 10
- 239000002994 raw material Substances 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000004427 diamine group Chemical group 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 230000001678 irradiating effect Effects 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- YILSKTLGXQKJMI-UHFFFAOYSA-N 1-bromo-4-[4-(4-propylcyclohexyl)cyclohexyl]benzene Chemical compound C1CC(CCC)CCC1C1CCC(C=2C=CC(Br)=CC=2)CC1 YILSKTLGXQKJMI-UHFFFAOYSA-N 0.000 description 1
- ZDFBKZUDCQQKAC-UHFFFAOYSA-N 1-bromo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Br)C=C1 ZDFBKZUDCQQKAC-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- LNBCORQTMWLBNE-UHFFFAOYSA-N N-(4-nitrophenyl)-4-[4-(4-propylcyclohexyl)cyclohexyl]aniline Chemical compound C(CC)C1CCC(CC1)C1CCC(CC1)C1=CC=C(C=C1)NC1=CC=C(C=C1)[N+](=O)[O-] LNBCORQTMWLBNE-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- CNXMDTWQWLGCPE-UHFFFAOYSA-N ditert-butyl-(2-phenylphenyl)phosphane Chemical group CC(C)(C)P(C(C)(C)C)C1=CC=CC=C1C1=CC=CC=C1 CNXMDTWQWLGCPE-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- PDODYIVPNIJZLR-UHFFFAOYSA-N n-methyl-4-nitro-n-(4-nitrophenyl)benzamide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1N(C)C(=O)C1=CC=C([N+]([O-])=O)C=C1 PDODYIVPNIJZLR-UHFFFAOYSA-N 0.000 description 1
- XIFJZJPMHNUGRA-UHFFFAOYSA-N n-methyl-4-nitroaniline Chemical compound CNC1=CC=C([N+]([O-])=O)C=C1 XIFJZJPMHNUGRA-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2005015202A JP4821118B2 (ja) | 2004-02-12 | 2005-01-24 | ジアミン、ポリマー、液晶配向膜および液晶表示素子 |
| TW094103548A TWI307337B (en) | 2004-02-12 | 2005-02-04 | Diamine, polymer, liquid crystal display aligned film and liquid crystal display device |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004035773 | 2004-02-12 | ||
| JP2004035773 | 2004-02-12 | ||
| JP2005015202A JP4821118B2 (ja) | 2004-02-12 | 2005-01-24 | ジアミン、ポリマー、液晶配向膜および液晶表示素子 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005255981A JP2005255981A (ja) | 2005-09-22 |
| JP2005255981A5 true JP2005255981A5 (enExample) | 2008-02-21 |
| JP4821118B2 JP4821118B2 (ja) | 2011-11-24 |
Family
ID=37148153
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005015202A Expired - Fee Related JP4821118B2 (ja) | 2004-02-12 | 2005-01-24 | ジアミン、ポリマー、液晶配向膜および液晶表示素子 |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP4821118B2 (enExample) |
| KR (2) | KR100655766B1 (enExample) |
| TW (1) | TWI307337B (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2006265835B2 (en) * | 2005-06-30 | 2012-05-03 | Amgen Inc. | Bis-aryl kinase inhibitors and their use in the treatment of inflammation, angiogenesis and cancer |
| JP2007015952A (ja) * | 2005-07-06 | 2007-01-25 | Shionogi & Co Ltd | ナフタレン誘導体 |
| US9409856B2 (en) | 2005-11-28 | 2016-08-09 | Gtx, Inc. | Estrogen receptor ligands and methods of use thereof |
| US8637706B2 (en) | 2005-11-28 | 2014-01-28 | Gtx, Inc. | Nuclear receptor binding agents |
| US8546451B2 (en) | 2005-11-28 | 2013-10-01 | Gtx, Inc. | Estrogen receptor ligands and methods of use thereof |
| KR100822499B1 (ko) * | 2005-12-01 | 2008-04-16 | 주식회사 엘지화학 | 신규한 폴리이미드 및 이의 제조방법 |
| KR101257437B1 (ko) * | 2006-02-22 | 2013-04-23 | 주식회사 동진쎄미켐 | 수직배향모드 액정표시소자의 배향재료 및 이의 제조방법 |
| JP5481771B2 (ja) * | 2006-03-16 | 2014-04-23 | Ｊｎｃ株式会社 | 光配向膜及び液晶表示素子 |
| TWI464158B (zh) | 2006-03-16 | 2014-12-11 | Jnc Corp | 四羧酸二酐 |
| TWI477554B (zh) * | 2006-07-10 | 2015-03-21 | Jnc Corp | 液晶配向劑、液晶配向膜以及液晶顯示元件 |
| KR100710472B1 (ko) * | 2006-10-18 | 2007-04-24 | 주식회사가야건축사사무소 | 실내외 기밀성 유지를 위한 주택용 도어구조 |
| WO2008084944A1 (en) * | 2007-01-09 | 2008-07-17 | Lg Chem, Ltd. | New copolyimide, liquid crystal aligning layer comprising the same, and liquid crystal display comprising the same |
| US9427418B2 (en) | 2009-02-23 | 2016-08-30 | Gtx, Inc. | Estrogen receptor ligands and methods of use thereof |
| US9624161B2 (en) | 2009-02-23 | 2017-04-18 | Gtx, Inc. | Estrogen receptor ligands and methods of use thereof |
| KR101582157B1 (ko) | 2009-08-05 | 2016-01-05 | 삼성디스플레이 주식회사 | 액정표시패널 및 이의 제조방법 |
| EP2492271B1 (en) * | 2009-10-23 | 2018-05-09 | Shanghai Institute Of Organic Chemistry, Chinese Academy Of Sciences | Sulfur containing heterocycle-fused naphthalene tetracarboxylic acid diimide derivatives, preparation method and use thereof |
| JP5856147B2 (ja) | 2010-04-23 | 2016-02-09 | ロリク アーゲーＲｏｌｉｃ Ａｇ | 光配向材料 |
| JP6318467B2 (ja) * | 2013-04-18 | 2018-05-09 | Jsr株式会社 | 液晶配向剤、液晶配向膜、液晶表示素子、位相差フィルム、位相差フィルムの製造方法及び重合体 |
| JPWO2014185413A1 (ja) * | 2013-05-13 | 2017-02-23 | 日産化学工業株式会社 | 横電界駆動型液晶表示素子用液晶配向膜を有する基板の製造方法 |
| JP6492564B2 (ja) * | 2014-02-13 | 2019-04-03 | Jsr株式会社 | 液晶配向剤、液晶配向膜、液晶表示素子、位相差フィルム、位相差フィルムの製造方法、重合体及び化合物 |
| KR102212324B1 (ko) | 2014-02-21 | 2021-02-04 | 삼성디스플레이 주식회사 | 광배향제 및 이를 포함하는 액정 표시 장치 |
| JP6243862B2 (ja) * | 2015-02-17 | 2017-12-06 | 富士フイルム株式会社 | 液晶配向膜の製造方法、液晶表示装置の製造方法および液晶表示装置 |
| KR102719144B1 (ko) * | 2015-03-24 | 2024-10-18 | 닛산 가가쿠 가부시키가이샤 | 액정 배향제, 액정 배향막 및 액정 표시 소자 |
| KR101989587B1 (ko) * | 2016-03-28 | 2019-06-14 | 주식회사 엘지화학 | 액정 배향제, 이를 포함하는 액정배향막 및 액정배향막의 제조 방법 |
| US11098050B2 (en) * | 2016-08-11 | 2021-08-24 | Merck Patent Gmbh | Organic semiconducting compounds comprising a tetraazapyrene core |
| KR102089122B1 (ko) * | 2016-08-25 | 2020-03-13 | 주식회사 엘지화학 | 디아민 화합물 및 이를 이용하여 제조된 플렉시블 소자용 기판 |
| KR102782854B1 (ko) | 2019-06-04 | 2025-03-14 | 삼성전자주식회사 | 폴리(아미드-이미드) 코폴리머, 폴리(아미드-이미드) 코폴리머 제조용 조성물, 폴리(아미드-이미드) 코폴리머를 포함하는 성형품 및 표시 장치 |
| JP2022142780A (ja) * | 2021-03-16 | 2022-09-30 | 東ソー株式会社 | 光反応性ポリマー、モノマー、光学フィルム |
| JP2023053917A (ja) * | 2021-10-01 | 2023-04-13 | エスケー イノベーション カンパニー リミテッド | 新規なジアミン、それにより製造された重合体およびフィルム |
| JP2023081407A (ja) * | 2021-12-01 | 2023-06-13 | 東ソー株式会社 | 光反応性ポリマーを含む樹脂組成物、光学薄膜 |
| CN115784923B (zh) * | 2022-12-12 | 2024-06-14 | 宁波博雅聚力新材料科技有限公司 | 制备聚酰亚胺薄膜用二胺单体及制备方法和聚酰亚胺薄膜 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3282897A (en) * | 1963-09-25 | 1966-11-01 | Du Pont | Process for preparing a polyamide-ester |
| US3926922A (en) * | 1974-03-14 | 1975-12-16 | Polaroid Corp | Polyurethane elastomers prepared from diamine curing agents |
| FR2279822A1 (fr) * | 1974-07-24 | 1976-02-20 | Ugine Kuhlmann | Nouveaux colorants disazoiques hydrosolubles et nouvelles matieres premieres utilisables pour leur preparation |
| JPS6317933A (ja) * | 1986-07-09 | 1988-01-25 | Toray Ind Inc | 熱硬化性アミドイミド樹脂およびその製造法 |
| US4742150A (en) * | 1986-09-25 | 1988-05-03 | General Electric Company | Solvent resistant polyetheramideimide containing benzanilide units |
| JPH07152037A (ja) * | 1993-11-26 | 1995-06-16 | Chisso Corp | 液晶配向膜及び液晶表示素子 |
| US6808766B1 (en) * | 1998-08-26 | 2004-10-26 | Nissan Chemical Industries, Ltd. | Liquid crystal alignment agent and liquid crystal device using the liquid crystal alignment and method for alignment of liquid crystal molecules |
| KR100565739B1 (ko) * | 2000-10-28 | 2006-03-29 | 엘지.필립스 엘시디 주식회사 | 광배향성 물질 및 이를 이용한 액정표시소자 |
| JP2003073471A (ja) * | 2001-08-31 | 2003-03-12 | Jsr Corp | 垂直配向型液晶配向剤およびそれを用いた液晶表示素子 |
| JP2003255349A (ja) * | 2002-03-05 | 2003-09-10 | Jsr Corp | 液晶配向膜、液晶配向膜の製造方法、および液晶表示素子 |
-
2005
- 2005-01-24 JP JP2005015202A patent/JP4821118B2/ja not_active Expired - Fee Related
- 2005-02-04 TW TW094103548A patent/TWI307337B/zh not_active IP Right Cessation
- 2005-02-07 KR KR1020050011449A patent/KR100655766B1/ko not_active Expired - Fee Related
-
2006
- 2006-09-01 KR KR1020060084237A patent/KR100775012B1/ko not_active Expired - Fee Related
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