TW201348294A - 新穎二胺，聚合物，液晶配向劑，液晶配向膜，及使用其之液晶顯示元件 - Google Patents

新穎二胺，聚合物，液晶配向劑，液晶配向膜，及使用其之液晶顯示元件 Download PDF

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Publication number: TW201348294A
Authority: TW; Taiwan
Prior art keywords: liquid crystal; acid; diamine; group; crystal alignment
Prior art date: 2012-02-01

Application number

TW102103982A

Other languages

English (en)

Chinese (zh)

Other versions

TWI561555B (fr

Inventor

Takahiro Noda

Oki Mochizuki

Daisuke Sakuma

Original Assignee

Nissan Chemical Ind Ltd

Priority date (The priority date 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 date listed.)

2012-02-01

Filing date

2013-02-01

Publication date

2013-12-01

2013-02-01 Application filed by Nissan Chemical Ind Ltd filed Critical Nissan Chemical Ind Ltd

2013-12-01 Publication of TW201348294A publication Critical patent/TW201348294A/zh

2016-12-11 Application granted granted Critical

2016-12-11 Publication of TWI561555B publication Critical patent/TWI561555B/zh

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150000004985 diamines Chemical class 0.000 title claims abstract description 96
229920000642 polymer Polymers 0.000 title claims abstract description 52
239000004973 liquid crystal related substance Substances 0.000 title claims description 140
239000003795 chemical substances by application Substances 0.000 title claims description 97
125000003277 amino group Chemical group 0.000 claims abstract description 30
125000000962 organic group Chemical group 0.000 claims abstract description 24
150000002148 esters Chemical class 0.000 claims abstract description 17
229920000768 polyamine Polymers 0.000 claims description 47
125000000217 alkyl group Chemical group 0.000 claims description 21
108010039918 Polylysine Proteins 0.000 claims description 19
229920000656 polylysine Polymers 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 18
238000006297 dehydration reaction Methods 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
230000018044 dehydration Effects 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
238000006798 ring closing metathesis reaction Methods 0.000 claims description 8
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 4
150000002923 oximes Chemical class 0.000 claims description 4
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
229920005575 poly(amic acid) Polymers 0.000 abstract description 26
229920001721 polyimide Polymers 0.000 abstract description 4
239000004952 Polyamide Substances 0.000 abstract description 3
229920002647 polyamide Polymers 0.000 abstract description 3
238000007363 ring formation reaction Methods 0.000 abstract description 2
239000004642 Polyimide Substances 0.000 abstract 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 116
-1 t-butoxycarbonyl group Chemical group 0.000 description 88
238000006243 chemical reaction Methods 0.000 description 65
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239000000243 solution Substances 0.000 description 50
239000002253 acid Substances 0.000 description 46
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 40
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
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 description 36
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238000000034 method Methods 0.000 description 28
239000007787 solid Substances 0.000 description 28
239000000758 substrate Substances 0.000 description 27
238000003786 synthesis reaction Methods 0.000 description 27
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125000006158 tetracarboxylic acid group Chemical group 0.000 description 26
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229910052757 nitrogen Inorganic materials 0.000 description 23
230000000052 comparative effect Effects 0.000 description 22
239000012299 nitrogen atmosphere Substances 0.000 description 22
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 21
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239000011248 coating agent Substances 0.000 description 16
150000001875 compounds Chemical class 0.000 description 16
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239000003960 organic solvent Substances 0.000 description 16
238000002360 preparation method Methods 0.000 description 16
239000002585 base Substances 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
210000002858 crystal cell Anatomy 0.000 description 12
238000004090 dissolution Methods 0.000 description 12
229920005989 resin Polymers 0.000 description 12
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229910052731 fluorine Inorganic materials 0.000 description 8
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238000007639 printing Methods 0.000 description 8
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230000000694 effects Effects 0.000 description 6
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
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238000006116 polymerization reaction Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 5
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101100273988 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) paa-3 gene Proteins 0.000 description 5
101150033824 PAA1 gene Proteins 0.000 description 5
101000836070 Rattus norvegicus Serine protease inhibitor A3L Proteins 0.000 description 5
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 5
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 5
102100027654 Transcription factor PU.1 Human genes 0.000 description 5
125000001931 aliphatic group Chemical group 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
238000005227 gel permeation chromatography Methods 0.000 description 5
239000002243 precursor Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 4
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SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 4
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BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
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239000001257 hydrogen Substances 0.000 description 4
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AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
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GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
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CURBACXRQKTCKZ-UHFFFAOYSA-N cyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C(O)=O)C1C(O)=O CURBACXRQKTCKZ-UHFFFAOYSA-N 0.000 description 1
SUSAGCZZQKACKE-UHFFFAOYSA-N cyclobutane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC1C(O)=O SUSAGCZZQKACKE-UHFFFAOYSA-N 0.000 description 1
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VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
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FDKLLWKMYAMLIF-UHFFFAOYSA-N cyclopropane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC1 FDKLLWKMYAMLIF-UHFFFAOYSA-N 0.000 description 1
RLWFMZKPPHHHCB-UHFFFAOYSA-N cyclopropane-1,2-dicarboxylate;hydron Chemical compound OC(=O)C1CC1C(O)=O RLWFMZKPPHHHCB-UHFFFAOYSA-N 0.000 description 1
DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
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239000003989 dielectric material Substances 0.000 description 1
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239000010931 gold Substances 0.000 description 1
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SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
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XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
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LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical class [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 description 1
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KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
VAWFFNJAPKXVPH-UHFFFAOYSA-N naphthalene-1,6-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC2=CC(C(=O)O)=CC=C21 VAWFFNJAPKXVPH-UHFFFAOYSA-N 0.000 description 1
WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
CJYCVQJRVSAFKB-UHFFFAOYSA-N octadecane-1,18-diamine Chemical compound NCCCCCCCCCCCCCCCCCCN CJYCVQJRVSAFKB-UHFFFAOYSA-N 0.000 description 1
238000007645 offset printing Methods 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
UFOIOXZLTXNHQH-UHFFFAOYSA-N oxolane-2,3,4,5-tetracarboxylic acid Chemical compound OC(=O)C1OC(C(O)=O)C(C(O)=O)C1C(O)=O UFOIOXZLTXNHQH-UHFFFAOYSA-N 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000005010 perfluoroalkyl group Chemical group 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000004597 plastic additive Substances 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
238000012643 polycondensation polymerization Methods 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
239000009719 polyimide resin Substances 0.000 description 1
229920006375 polyphtalamide Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003139 primary aliphatic amines Chemical class 0.000 description 1
239000001294 propane Substances 0.000 description 1
ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
JCMFJIHDWDKYIL-UHFFFAOYSA-N propyl 3-methoxypropanoate Chemical compound CCCOC(=O)CCOC JCMFJIHDWDKYIL-UHFFFAOYSA-N 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
229940032159 propylene carbonate Drugs 0.000 description 1
229940116423 propylene glycol diacetate Drugs 0.000 description 1
LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
UWQVWPZBJCDVQM-UHFFFAOYSA-N pyrrolo[1,2-a]benzimidazol-1-one Chemical compound C1=CC=C2N3C(=O)C=CC3=NC2=C1 UWQVWPZBJCDVQM-UHFFFAOYSA-N 0.000 description 1
150000004060 quinone imines Chemical group 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007430 reference method Methods 0.000 description 1
230000003252 repetitive effect Effects 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007650 screen-printing Methods 0.000 description 1
238000007789 sealing Methods 0.000 description 1
150000005619 secondary aliphatic amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000004528 spin coating Methods 0.000 description 1
JQZAKMJZYGPUFD-UHFFFAOYSA-N spiro[3.3]heptane-2,6-dicarboxylic acid Chemical compound C1C(C(=O)O)CC21CC(C(O)=O)C2 JQZAKMJZYGPUFD-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
JVSKTVYZLJDMOR-UHFFFAOYSA-N tert-butyl N-(2-amino-4-nitrophenyl)carbamate Chemical compound C(C)(C)(C)OC(=O)NC1=C(N)C=C(C=C1)[N+](=O)[O-] JVSKTVYZLJDMOR-UHFFFAOYSA-N 0.000 description 1
CELIXTBMYJJUCO-UHFFFAOYSA-N tert-butyl n-(2,4-diaminophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(N)C=C1N CELIXTBMYJJUCO-UHFFFAOYSA-N 0.000 description 1
FEDAACZCXXCKQP-UHFFFAOYSA-N tert-butyl n-(2-amino-5-nitrophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC([N+]([O-])=O)=CC=C1N FEDAACZCXXCKQP-UHFFFAOYSA-N 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
QWFRRFLKWRIKSZ-UHFFFAOYSA-N truxillic acid Chemical compound OC(=O)C1C(C=2C=CC=CC=2)C(C(O)=O)C1C1=CC=CC=C1 QWFRRFLKWRIKSZ-UHFFFAOYSA-N 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
230000002087 whitening effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/18—Polybenzimidazoles
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/20—Pyrrones
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
- G02F1/133723—Polyimide, polyamide-imide

Landscapes

Chemical & Material Sciences (AREA)
Physics & Mathematics (AREA)
Medicinal Chemistry (AREA)
Health & Medical Sciences (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Nonlinear Science (AREA)
Spectroscopy & Molecular Physics (AREA)
Mathematical Physics (AREA)
Crystallography & Structural Chemistry (AREA)
General Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Liquid Crystal (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

TW102103982A 2012-02-01 2013-02-01 新穎二胺，聚合物，液晶配向劑，液晶配向膜，及使用其之液晶顯示元件 TW201348294A (zh)

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TWI561555B TWI561555B (fr)	2016-12-11

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JP (1)	JP6070958B2 (fr)
KR (1)	KR101998909B1 (fr)
CN (1)	CN104220488B (fr)
TW (1)	TW201348294A (fr)
WO (1)	WO2013115228A1 (fr)

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CN105073708B (zh) *	2012-12-25	2017-02-22	日产化学工业株式会社	新的二胺、聚合物、液晶取向剂、液晶取向膜和使用了该液晶取向膜的液晶显示元件
JP6252009B2 (ja) *	2013-07-24	2017-12-27	Jnc株式会社	新規ジアミン、これを用いたポリマー、液晶配向剤、液晶配向膜、および液晶表示素子
KR102331107B1 (ko) *	2014-02-05	2021-11-24	닛산 가가쿠 가부시키가이샤	액정 배향제, 액정 배향막, 및 그것을 사용한 액정 표시 소자
KR102421827B1 (ko) *	2014-06-25	2022-07-15	닛산 가가쿠 가부시키가이샤	액정 배향제, 액정 배향막 및 액정 표시 소자
JP6686298B2 (ja)	2014-08-25	2020-04-22	Jsr株式会社	液晶配向剤、液晶配向膜及び液晶表示素子
TWI682969B (zh) *	2014-10-23	2020-01-21	日商宇部興產股份有限公司	聚醯亞胺膜、聚醯亞胺前驅體及聚醯亞胺
JP6447304B2 (ja)	2015-03-27	2019-01-09	Jsr株式会社	液晶配向剤、液晶配向膜及びその製造方法、液晶表示素子、位相差フィルム及びその製造方法、重合体並びに化合物
KR102704513B1 (ko) *	2015-10-07	2024-09-06	닛산 가가쿠 가부시키가이샤	액정 배향제, 액정 배향막, 및 액정 표시 소자
WO2017135216A1 (fr) *	2016-02-03	2017-08-10	シャープ株式会社	Film orienté, polymère, et dispositif d'affichage à cristaux liquides
JP7076939B2 (ja) *	2016-07-19	2022-05-30	株式会社ジャパンディスプレイ	光配向膜用ワニス及び液晶表示装置
JP6962388B2 (ja) *	2018-01-25	2021-11-05	Jsr株式会社	液晶配向剤、液晶配向膜、液晶素子及び液晶素子の製造方法
KR102814925B1 (ko) *	2019-02-08	2025-05-29	닛산 가가쿠 가부시키가이샤	액정 배향제, 액정 배향막 및 그것을 사용한 액정 표시 소자
CN110734771B (zh) *	2019-09-27	2022-12-20	江苏三月科技股份有限公司	液晶取向剂、液晶取向膜及液晶显示元件
WO2023167545A1 (fr) *	2022-03-04	2023-09-07	한국화학연구원	Polybenzimidazole portant des groupes protecteurs, procédé de préparation d'une membrane utilisant celui-ci et son utilisation
CN116622068B (zh) *	2023-05-19	2025-03-14	常州大学	一种荧光聚合物、高弹性柔性荧光复合纤维制备及其应用

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2013
- 2013-01-30 KR KR1020147024378A patent/KR101998909B1/ko active Active
- 2013-01-30 WO PCT/JP2013/052003 patent/WO2013115228A1/fr not_active Ceased
- 2013-01-30 CN CN201380017999.4A patent/CN104220488B/zh active Active
- 2013-01-30 JP JP2013556435A patent/JP6070958B2/ja active Active
- 2013-02-01 TW TW102103982A patent/TW201348294A/zh unknown

Also Published As

Publication number	Publication date
KR20140119181A (ko)	2014-10-08
TWI561555B (fr)	2016-12-11
JPWO2013115228A1 (ja)	2015-05-11
JP6070958B2 (ja)	2017-02-01
WO2013115228A1 (fr)	2013-08-08
CN104220488B (zh)	2017-05-31
CN104220488A (zh)	2014-12-17
KR101998909B1 (ko)	2019-07-10

Publication	Publication Date	Title
TW201348294A (zh)	2013-12-01	新穎二胺，聚合物，液晶配向劑，液晶配向膜，及使用其之液晶顯示元件
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TWI526419B (zh)	2016-03-21	Novel diamine, polymer, liquid crystal aligning agent, liquid crystal alignment film and liquid crystal display device using the same
TWI442142B (zh)	2014-06-21	A liquid crystal aligning agent, an alignment film and a liquid crystal display device
TWI436980B (zh)	2014-05-11	Diamine, polyimide precursor, polyimide, liquid crystal aligning agent, liquid crystal alignment film and liquid crystal display element
TWI534179B (zh)	2016-05-21	A polyimide precursor modified with a dicarboxylic anhydride, an imidized polyimide and a liquid crystal alignment treatment agent using the same
TWI620769B (zh)	2018-04-11	Liquid crystal alignment agent, liquid crystal alignment film, and liquid crystal display element
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TWI549990B (zh)	2016-09-21	A liquid crystal alignment agent, a liquid crystal alignment film and a liquid crystal display device using the same
TWI454504B (zh)	2014-10-01	A liquid crystal alignment agent and a liquid crystal display device using the liquid crystal display device
TWI478959B (zh)	2015-04-01	A liquid crystal alignment agent, a liquid crystal alignment film, and a liquid crystal display device and a compound using the same
TW201211108A (en)	2012-03-16	Liquid crystal aligning agent, liquid crystal alignment film produced using same, and liquid crystal display element
TWI596201B (zh)	2017-08-21	Liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display element
KR102073437B1 (ko)	2020-02-04	중합체, 액정 배향제, 액정 배향막 및 액정 표시 소자 그리고 디아민