JP2008515933A5 - - Google Patents
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- JP2008515933A5 JP2008515933A5 JP2007535977A JP2007535977A JP2008515933A5 JP 2008515933 A5 JP2008515933 A5 JP 2008515933A5 JP 2007535977 A JP2007535977 A JP 2007535977A JP 2007535977 A JP2007535977 A JP 2007535977A JP 2008515933 A5 JP2008515933 A5 JP 2008515933A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- acid
- amino
- bis
- dianhydride
- 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 cyano, carboxy Chemical group 0.000 claims 49
- 229920000642 polymer Polymers 0.000 claims 29
- 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 21
- 125000004432 carbon atom Chemical group C* 0.000 claims 19
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 239000011737 fluorine Substances 0.000 claims 10
- 229910052731 fluorine Inorganic materials 0.000 claims 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 9
- 239000000460 chlorine Substances 0.000 claims 9
- 229910052801 chlorine Inorganic materials 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 8
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 125000001153 fluoro group Chemical group F* 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 229910003849 O-Si Inorganic materials 0.000 claims 6
- 229910003872 O—Si Inorganic materials 0.000 claims 6
- 125000002837 carbocyclic group Chemical group 0.000 claims 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 5
- 125000004122 cyclic group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000004429 atom Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 claims 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 3
- 125000002723 alicyclic group Chemical group 0.000 claims 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims 3
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 150000004985 diamines Chemical class 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 239000004973 liquid crystal related substance Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004957 naphthylene group Chemical group 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000005562 phenanthrylene group Chemical group 0.000 claims 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 3
- 229920005575 poly(amic acid) Polymers 0.000 claims 3
- 238000006068 polycondensation reaction Methods 0.000 claims 3
- AXKGIPZJYUNAIW-UHFFFAOYSA-N (4-aminophenyl)methanol Chemical compound NC1=CC=C(CO)C=C1 AXKGIPZJYUNAIW-UHFFFAOYSA-N 0.000 claims 2
- LDQMZKBIBRAZEA-UHFFFAOYSA-N 2,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C(N)=C1 LDQMZKBIBRAZEA-UHFFFAOYSA-N 0.000 claims 2
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 claims 2
- GWTJRFCUTIHVPX-UHFFFAOYSA-N 2,7-diaminofluoren-9-one Chemical compound C1=C(N)C=C2C(=O)C3=CC(N)=CC=C3C2=C1 GWTJRFCUTIHVPX-UHFFFAOYSA-N 0.000 claims 2
- UAIUNKRWKOVEES-UHFFFAOYSA-N 3,3',5,5'-tetramethylbenzidine Chemical compound CC1=C(N)C(C)=CC(C=2C=C(C)C(N)=C(C)C=2)=C1 UAIUNKRWKOVEES-UHFFFAOYSA-N 0.000 claims 2
- HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical compound C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 claims 2
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 claims 2
- NRLUQVLHGAVXQB-UHFFFAOYSA-N 4-(4-amino-2-chloro-5-methoxyphenyl)-5-chloro-2-methoxyaniline Chemical compound C1=C(N)C(OC)=CC(C=2C(=CC(N)=C(OC)C=2)Cl)=C1Cl NRLUQVLHGAVXQB-UHFFFAOYSA-N 0.000 claims 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims 2
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 claims 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims 2
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims 2
- HJSYPLCSZPEDCQ-UHFFFAOYSA-N 5-[2-(3-amino-4-methylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-methylaniline Chemical compound C1=C(N)C(C)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(C)C(N)=C1 HJSYPLCSZPEDCQ-UHFFFAOYSA-N 0.000 claims 2
- SNCJAJRILVFXAE-UHFFFAOYSA-N 9h-fluorene-2,7-diamine Chemical compound NC1=CC=C2C3=CC=C(N)C=C3CC2=C1 SNCJAJRILVFXAE-UHFFFAOYSA-N 0.000 claims 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- 239000004971 Cross linker Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000004642 Polyimide Substances 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims 2
- TUQQUUXMCKXGDI-UHFFFAOYSA-N bis(3-aminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(N)C=CC=2)=C1 TUQQUUXMCKXGDI-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical group FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000000962 organic group Chemical group 0.000 claims 2
- 238000006349 photocyclization reaction Methods 0.000 claims 2
- 229920001721 polyimide Polymers 0.000 claims 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims 2
- 125000006850 spacer group Chemical group 0.000 claims 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims 2
- QYGLNAUVXLNBNS-QWRGUYRKSA-N (1s,2s)-1-(4-aminophenyl)-2-(dimethylamino)propane-1,3-diol Chemical compound CN(C)[C@@H](CO)[C@@H](O)C1=CC=C(N)C=C1 QYGLNAUVXLNBNS-QWRGUYRKSA-N 0.000 claims 1
- FEEVEFUWQDGMKI-UHFFFAOYSA-N (3,4-diaminophenyl)methanol;dihydrochloride Chemical compound Cl.Cl.NC1=CC=C(CO)C=C1N FEEVEFUWQDGMKI-UHFFFAOYSA-N 0.000 claims 1
- KBCPMQUSOLSAQO-UHFFFAOYSA-N (4-carboxyphenyl)azanium;chloride Chemical compound Cl.NC1=CC=C(C(O)=O)C=C1 KBCPMQUSOLSAQO-UHFFFAOYSA-N 0.000 claims 1
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 claims 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 claims 1
- ICBZWZFNERWRHJ-UHFFFAOYSA-N 1-(4-aminophenyl)ethanol;4-aminophthalic acid Chemical compound CC(O)C1=CC=C(N)C=C1.NC1=CC=C(C(O)=O)C(C(O)=O)=C1 ICBZWZFNERWRHJ-UHFFFAOYSA-N 0.000 claims 1
- YDTXVOVKGSXZBI-UHFFFAOYSA-N 1-(4-aminophenyl)propan-1-ol Chemical compound CCC(O)C1=CC=C(N)C=C1 YDTXVOVKGSXZBI-UHFFFAOYSA-N 0.000 claims 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims 1
- YDFDTKKXMZRNHR-UHFFFAOYSA-N 1-n,3-n-dimethylcyclohexane-1,3-diamine Chemical compound CNC1CCCC(NC)C1 YDFDTKKXMZRNHR-UHFFFAOYSA-N 0.000 claims 1
- UXOXUHMFQZEAFR-UHFFFAOYSA-N 2,2',5,5'-Tetrachlorobenzidine Chemical compound C1=C(Cl)C(N)=CC(Cl)=C1C1=CC(Cl)=C(N)C=C1Cl UXOXUHMFQZEAFR-UHFFFAOYSA-N 0.000 claims 1
- HVIRLGRKYPEHCB-UHFFFAOYSA-N 2,4-dimethylbicyclo[2.2.2]oct-2-ene-5,6,7,8-tetracarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C2C(C)=CC1(C)C(C(O)=O)C2C(O)=O HVIRLGRKYPEHCB-UHFFFAOYSA-N 0.000 claims 1
- OJSPYCPPVCMEBS-UHFFFAOYSA-N 2,8-dimethyl-5,5-dioxodibenzothiophene-3,7-diamine Chemical compound C12=CC(C)=C(N)C=C2S(=O)(=O)C2=C1C=C(C)C(N)=C2 OJSPYCPPVCMEBS-UHFFFAOYSA-N 0.000 claims 1
- TZEJXCIGVMTMDY-UHFFFAOYSA-N 2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound NC1=CC=C(C(O)(C(F)(F)F)C(F)(F)F)C=C1 TZEJXCIGVMTMDY-UHFFFAOYSA-N 0.000 claims 1
- PSYGCSGUGPKXRN-UHFFFAOYSA-N 2-[1-(4-aminophenyl)-1,3-dihydroxypropan-2-yl]isoindole-1,3-dione Chemical compound C1=CC(N)=CC=C1C(O)C(CO)N1C(=O)C2=CC=CC=C2C1=O PSYGCSGUGPKXRN-UHFFFAOYSA-N 0.000 claims 1
- MXPYJVUYLVNEBB-UHFFFAOYSA-N 2-[2-(2-carboxybenzoyl)oxycarbonylbenzoyl]oxycarbonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(O)=O MXPYJVUYLVNEBB-UHFFFAOYSA-N 0.000 claims 1
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 claims 1
- IIQLVLWFQUUZII-UHFFFAOYSA-N 2-amino-5-(4-amino-3-carboxyphenyl)benzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC=C1C1=CC=C(N)C(C(O)=O)=C1 IIQLVLWFQUUZII-UHFFFAOYSA-N 0.000 claims 1
- ZGDMDBHLKNQPSD-UHFFFAOYSA-N 2-amino-5-(4-amino-3-hydroxyphenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=C(N)C(O)=C1 ZGDMDBHLKNQPSD-UHFFFAOYSA-N 0.000 claims 1
- UWJRLHJGFULWLO-UHFFFAOYSA-N 2-n,3,3,5-tetramethylcyclopentane-1,2-diamine Chemical compound CNC1C(N)C(C)CC1(C)C UWJRLHJGFULWLO-UHFFFAOYSA-N 0.000 claims 1
- HSTOKWSFWGCZMH-UHFFFAOYSA-N 3,3'-diaminobenzidine Chemical compound C1=C(N)C(N)=CC=C1C1=CC=C(N)C(N)=C1 HSTOKWSFWGCZMH-UHFFFAOYSA-N 0.000 claims 1
- HEMGYNNCNNODNX-UHFFFAOYSA-N 3,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1N HEMGYNNCNNODNX-UHFFFAOYSA-N 0.000 claims 1
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 claims 1
- RHRNYXVSZLSRRP-UHFFFAOYSA-N 3-(carboxymethyl)cyclopentane-1,2,4-tricarboxylic acid Chemical compound OC(=O)CC1C(C(O)=O)CC(C(O)=O)C1C(O)=O RHRNYXVSZLSRRP-UHFFFAOYSA-N 0.000 claims 1
- CKOFBUUFHALZGK-UHFFFAOYSA-N 3-[(3-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC(CC=2C=C(N)C=CC=2)=C1 CKOFBUUFHALZGK-UHFFFAOYSA-N 0.000 claims 1
- UVUCUHVQYAPMEU-UHFFFAOYSA-N 3-[2-(3-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]aniline Chemical compound NC1=CC=CC(C(C=2C=C(N)C=CC=2)(C(F)(F)F)C(F)(F)F)=C1 UVUCUHVQYAPMEU-UHFFFAOYSA-N 0.000 claims 1
- DKKYOQYISDAQER-UHFFFAOYSA-N 3-[3-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=C(OC=3C=C(N)C=CC=3)C=CC=2)=C1 DKKYOQYISDAQER-UHFFFAOYSA-N 0.000 claims 1
- YOOSAIJKYCBPFW-UHFFFAOYSA-N 3-[4-(3-aminopropoxy)butoxy]propan-1-amine Chemical compound NCCCOCCCCOCCCN YOOSAIJKYCBPFW-UHFFFAOYSA-N 0.000 claims 1
- OMCQWROUUILBSU-UHFFFAOYSA-N 3-[[3-amino-5-(trifluoromethyl)phenyl]methyl]-5-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC(CC=2C=C(C=C(N)C=2)C(F)(F)F)=C1 OMCQWROUUILBSU-UHFFFAOYSA-N 0.000 claims 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 claims 1
- WECDUOXQLAIPQW-UHFFFAOYSA-N 4,4'-Methylene bis(2-methylaniline) Chemical compound C1=C(N)C(C)=CC(CC=2C=C(C)C(N)=CC=2)=C1 WECDUOXQLAIPQW-UHFFFAOYSA-N 0.000 claims 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims 1
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 claims 1
- BUDOGSSTKVVWDR-UHFFFAOYSA-N 4,4-bis(3-amino-4-hydroxyphenyl)pentanoic acid Chemical compound C=1C=C(O)C(N)=CC=1C(CCC(O)=O)(C)C1=CC=C(O)C(N)=C1 BUDOGSSTKVVWDR-UHFFFAOYSA-N 0.000 claims 1
- FFKSVVOWOROQIU-UHFFFAOYSA-N 4-(2,5-dioxooxolan-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic acid Chemical compound C12=CC=CC=C2C(C(O)=O)C(C(=O)O)CC1C1CC(=O)OC1=O FFKSVVOWOROQIU-UHFFFAOYSA-N 0.000 claims 1
- FWOLORXQTIGHFX-UHFFFAOYSA-N 4-(4-amino-2,3,5,6-tetrafluorophenyl)-2,3,5,6-tetrafluoroaniline Chemical group FC1=C(F)C(N)=C(F)C(F)=C1C1=C(F)C(F)=C(N)C(F)=C1F FWOLORXQTIGHFX-UHFFFAOYSA-N 0.000 claims 1
- XKXPBJBODVHDAW-UHFFFAOYSA-N 4-(4-amino-2-chlorophenyl)-3-chloroaniline Chemical compound ClC1=CC(N)=CC=C1C1=CC=C(N)C=C1Cl XKXPBJBODVHDAW-UHFFFAOYSA-N 0.000 claims 1
- XSSHPNOMIXIEKR-UHFFFAOYSA-N 4-(4-amino-3,5-dibromophenyl)-2,6-dibromoaniline Chemical compound C1=C(Br)C(N)=C(Br)C=C1C1=CC(Br)=C(N)C(Br)=C1 XSSHPNOMIXIEKR-UHFFFAOYSA-N 0.000 claims 1
- HUWXDEQWWKGHRV-KIVSLBCISA-N 4-(4-amino-3-chloro-2-deuteriophenyl)-2-chloro-N,N,3,5,6-pentadeuterioaniline Chemical compound ClC1=C(C(=C(C(=C1N([2H])[2H])[2H])[2H])C=1C(=C(C(N)=CC=1)Cl)[2H])[2H] HUWXDEQWWKGHRV-KIVSLBCISA-N 0.000 claims 1
- OCEINMLGYDSKFW-UHFFFAOYSA-N 4-(4-amino-3-nitrophenyl)-2-nitroaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1C1=CC=C(N)C([N+]([O-])=O)=C1 OCEINMLGYDSKFW-UHFFFAOYSA-N 0.000 claims 1
- RZPBZEISZUFQSV-UHFFFAOYSA-N 4-(4-aminonaphthalen-1-yl)naphthalen-1-amine Chemical group C12=CC=CC=C2C(N)=CC=C1C1=CC=C(N)C2=CC=CC=C12 RZPBZEISZUFQSV-UHFFFAOYSA-N 0.000 claims 1
- ZDFDINMHFLFYGQ-UHFFFAOYSA-N 4-(4-aminophenyl)-2-methoxyaniline Chemical compound C1=C(N)C(OC)=CC(C=2C=CC(N)=CC=2)=C1 ZDFDINMHFLFYGQ-UHFFFAOYSA-N 0.000 claims 1
- YYNCOERMULFLJD-UHFFFAOYSA-N 4-(4-aminophenyl)-3-nitroaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1[N+]([O-])=O YYNCOERMULFLJD-UHFFFAOYSA-N 0.000 claims 1
- KBZRHVNJCPVYDQ-UHFFFAOYSA-N 4-(carboxymethyl)bicyclo[2.2.1]heptane-2,3,6-tricarboxylic acid Chemical compound C1C2C(C(O)=O)CC1(CC(=O)O)C(C(O)=O)C2C(O)=O KBZRHVNJCPVYDQ-UHFFFAOYSA-N 0.000 claims 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 claims 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 claims 1
- ISESBQNCWCFFFR-UHFFFAOYSA-N 4-[2-(4-amino-2-methylphenyl)ethyl]-3-methylaniline Chemical group CC1=CC(N)=CC=C1CCC1=CC=C(N)C=C1C ISESBQNCWCFFFR-UHFFFAOYSA-N 0.000 claims 1
- BEKFRNOZJSYWKZ-UHFFFAOYSA-N 4-[2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(N)C=C1 BEKFRNOZJSYWKZ-UHFFFAOYSA-N 0.000 claims 1
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- CLCWCGOCHZSFQE-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)cyclohexanamine Chemical compound C1OC1CN(C1CCCCC1)CC1CO1 CLCWCGOCHZSFQE-UHFFFAOYSA-N 0.000 claims 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 claims 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 claims 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 claims 1
- 125000001402 nonanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 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 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- 239000003504 photosensitizing agent Substances 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 229920002959 polymer blend Polymers 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- CLNCMEVPMGQWTB-UHFFFAOYSA-N propan-2-yl 3,5-diaminobenzoate Chemical compound CC(C)OC(=O)C1=CC(N)=CC(N)=C1 CLNCMEVPMGQWTB-UHFFFAOYSA-N 0.000 claims 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 229920006301 statistical copolymer Polymers 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- OAXARSVKYJPDPA-UHFFFAOYSA-N tert-butyl 4-prop-2-ynylpiperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(CC#C)CC1 OAXARSVKYJPDPA-UHFFFAOYSA-N 0.000 claims 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 125000005730 thiophenylene group Chemical group 0.000 claims 1
- KRVRUAYUNOQMOV-UHFFFAOYSA-N tris(4-aminophenyl)methanol Chemical compound C1=CC(N)=CC=C1C(O)(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 KRVRUAYUNOQMOV-UHFFFAOYSA-N 0.000 claims 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 claims 1
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- YVDWFZIVIIKYBQ-UHFFFAOYSA-N Cc1nnc(C)[o]1 Chemical compound Cc1nnc(C)[o]1 YVDWFZIVIIKYBQ-UHFFFAOYSA-N 0.000 description 1
- JXQGICFGPUAVLJ-UHFFFAOYSA-N Cc1nnc(C)[s]1 Chemical compound Cc1nnc(C)[s]1 JXQGICFGPUAVLJ-UHFFFAOYSA-N 0.000 description 1
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| WO2006039824A1 (en) * | 2004-10-13 | 2006-04-20 | Rolic Ag | Photocrosslinkable materials |
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| EP1860094A1 (en) * | 2006-05-23 | 2007-11-28 | Rolic AG | Photocrosslinkable materials |
| EP2305632A1 (en) | 2005-12-23 | 2011-04-06 | Rolic AG | Photocrosslinkable materials |
| KR101318953B1 (ko) * | 2006-02-22 | 2013-10-17 | 주식회사 동진쎄미켐 | 수직배향모드의 액정표시소자의 배향재료 및 이의제조방법 |
| JP5092382B2 (ja) * | 2006-12-13 | 2012-12-05 | Ｊｎｃ株式会社 | 液晶類似構造を有するジアミン |
| EP1975687A1 (en) * | 2007-03-29 | 2008-10-01 | Rolic AG | Method of uniform and defect free liquid crystal aligning layers |
| EP2147948B1 (en) * | 2007-04-25 | 2014-11-12 | Nissan Chemical Industries, Ltd. | Polyimide precursor, polyimide, and coating solution for under layer film for image formation |
| JP5077048B2 (ja) * | 2007-05-02 | 2012-11-21 | Ｊｓｒ株式会社 | 垂直配向型液晶配向剤 |
| WO2008135131A1 (en) * | 2007-05-02 | 2008-11-13 | Rolic Ag | Thermally stable alignment materials |
| CN101687763B (zh) * | 2007-05-25 | 2014-02-19 | 罗利克有限公司 | 包含脂环基的光可交联材料 |
| CN101802692B (zh) * | 2007-09-26 | 2011-12-07 | Jsr株式会社 | 液晶取向剂、液晶取向膜以及液晶显示元件 |
| WO2009051207A1 (ja) * | 2007-10-19 | 2009-04-23 | Jsr Corporation | 液晶配向剤および液晶配向膜の形成方法 |
| JP5444690B2 (ja) * | 2007-12-06 | 2014-03-19 | Ｊｓｒ株式会社 | 液晶配向剤および液晶表示素子 |
| JP5726531B2 (ja) | 2007-12-21 | 2015-06-03 | ロリク リミテッドＲｏｌｉｃ Ｌｔｄ． | 光配向組成物 |
| WO2009080147A1 (en) * | 2007-12-21 | 2009-07-02 | Rolic Ag | Functionalized photoreactive compounds |
| JP4985609B2 (ja) * | 2007-12-26 | 2012-07-25 | Ｊｎｃ株式会社 | 液晶配向剤、液晶配向膜及び液晶表示素子 |
| NO2384318T3 (OSRAM) | 2008-12-31 | 2018-04-14 | ||
| US8411238B2 (en) * | 2009-07-08 | 2013-04-02 | Sharp Kabushiki Kaisha | Liquid crystal display panel and process for production thereof |
| KR101742838B1 (ko) * | 2009-12-14 | 2017-06-01 | 닛산 가가쿠 고교 가부시키 가이샤 | 액정 배향 처리제 및 그것을 사용한 액정 표시 소자 |
| JP5668907B2 (ja) * | 2009-12-25 | 2015-02-12 | Jsr株式会社 | 液晶配向剤、液晶配向膜および液晶表示素子 |
| WO2011122598A1 (ja) * | 2010-03-29 | 2011-10-06 | Dic株式会社 | 液晶配向層用ポリマー |
| JP5637019B2 (ja) * | 2010-04-27 | 2014-12-10 | Jsr株式会社 | 液晶配向剤 |
| JP5537345B2 (ja) * | 2010-09-03 | 2014-07-02 | 株式会社ジャパンディスプレイ | 液晶表示装置 |
| JP5767800B2 (ja) * | 2010-11-19 | 2015-08-19 | Jsr株式会社 | 液晶配向剤および液晶表示素子 |
| KR101387736B1 (ko) * | 2010-12-29 | 2014-04-21 | 제일모직주식회사 | 액정 배향제, 이를 이용하여 제조한 액정 배향막 및 상기 액정 배향막을 포함하는 액정표시소자 |
| KR101333711B1 (ko) | 2010-12-29 | 2013-11-27 | 제일모직주식회사 | 액정 배향제, 이를 이용하여 제조한 액정 배향막 및 상기 액정 배향막을 포함하는 액정표시소자 |
| US20120172541A1 (en) * | 2010-12-30 | 2012-07-05 | Cheil Industries Inc. | Liquid Crystal Alignment Agent, Liquid Crystal Alignment Film Manufactured Using the Same, and Liquid Crystal Display Device Including the Liquid Crystal Alignment Film |
| KR101864913B1 (ko) * | 2011-03-31 | 2018-06-05 | 닛산 가가쿠 고교 가부시키 가이샤 | 액정 배향제 및 그것을 사용한 액정 배향막 |
| CN103748192B (zh) | 2011-08-25 | 2016-07-27 | 罗利克有限公司 | 光反应性化合物 |
| BR112014007924A2 (pt) * | 2011-10-03 | 2017-04-11 | Rolic Ag | materiais de foto alinhamento |
| JP5939066B2 (ja) * | 2011-11-15 | 2016-06-22 | Jsr株式会社 | 液晶配向剤の製造方法 |
| WO2013073519A1 (ja) * | 2011-11-17 | 2013-05-23 | 国立大学法人北陸先端科学技術大学院大学 | 高分子原料及び高分子材料 |
| JP5962381B2 (ja) * | 2011-12-27 | 2016-08-03 | Jsr株式会社 | 液晶配向剤、液晶配向膜、液晶表示素子及び重合体 |
| WO2013099804A1 (ja) * | 2011-12-28 | 2013-07-04 | 日産化学工業株式会社 | 液晶配向剤、液晶配向膜、液晶表示素子及びジアミン化合物 |
| TWI635164B (zh) * | 2012-04-24 | 2018-09-11 | 迪愛生股份有限公司 | Liquid crystal composition containing polymerizable compound and liquid crystal display element using same |
| TWI642725B (zh) * | 2013-06-25 | 2018-12-01 | 日產化學工業股份有限公司 | Liquid crystal alignment agent, liquid crystal alignment film, liquid crystal display element |
| JP6451941B2 (ja) * | 2014-04-23 | 2019-01-16 | Jsr株式会社 | 液晶配向剤および液晶表示素子 |
| US10330981B2 (en) * | 2014-11-11 | 2019-06-25 | Samsung Display Co., Ltd. | Liquid crystal display device |
| KR102629649B1 (ko) | 2015-03-31 | 2024-01-29 | 롤리크 아게 | 광정렬 조성물 |
| CN105218435A (zh) * | 2015-10-12 | 2016-01-06 | 吉林大学 | 2，2-二[5-氨基-2-吡啶氧基]-1，1-联萘及其制备方法 |
| JP7052355B2 (ja) * | 2015-12-25 | 2022-04-12 | 日産化学株式会社 | 液晶表示素子、液晶光学素子及び液晶構造体安定化膜用組成物 |
| CN106833677A (zh) * | 2016-12-29 | 2017-06-13 | 深圳市华星光电技术有限公司 | 一种垂直取向剂材料 |
| CN109485582B (zh) * | 2018-11-08 | 2020-07-17 | 南京工业大学 | 一种芴酮基有机凝胶分子及其制备方法和应用 |
| CN113330078B (zh) * | 2018-12-19 | 2022-12-02 | 3M创新有限公司 | 剥离层及含有剥离层的制品 |
| US11667757B2 (en) | 2020-12-31 | 2023-06-06 | Industrial Technology Research Institute | Polymer, composition, and polysiloxane-polyimide material thereof |
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| US6608661B1 (en) * | 1992-07-08 | 2003-08-19 | Rolic Ag | Photo-oriented polymer network material having desired azimuthal orientation and tilt angle and method for its production |
| DE4408171A1 (de) * | 1994-03-11 | 1995-09-14 | Basf Ag | Neue polymerisierbare flüssigkristalline Verbindungen |
| EP0756193B1 (de) * | 1995-07-28 | 2016-02-17 | Rolic AG | Verfahren zur Erzeugung von Kippwinkeln in photoorientierten Polymernetzwerkschichten |
| US6066696A (en) | 1996-12-13 | 2000-05-23 | Samsung Display Devices Co. Ltd. | Optical alignment composition, alignment layer formed using the same and LCD having the alignment layer |
| KR19980057674A (ko) * | 1996-12-30 | 1998-09-25 | 손욱 | 배향막 형성용 조성물, 이로부터 형성되는 배향막과 이 배향막을 구비한 액정표시소자 |
| EP1021479B1 (en) * | 1997-09-25 | 2002-07-17 | Rolic AG | Photocrosslinkable polyimides |
| JP4266516B2 (ja) | 1998-03-20 | 2009-05-20 | ロリク アーゲー | 液晶配向層 |
| US6303742B1 (en) * | 1998-04-01 | 2001-10-16 | Kanekafuchi Kagaku Kogyo Kabushiki Kaisha | Polyimide compositions |
| US6194472B1 (en) | 1998-04-02 | 2001-02-27 | Akzo Nobel N.V. | Petroleum hydrocarbon in water colloidal dispersion |
| US6831148B2 (en) * | 2000-01-24 | 2004-12-14 | Rolic Ag | Photoactive polyimides, polyamide acids or esters with side chain photocrosslinkable groups |
| EP1277770A1 (en) * | 2001-07-17 | 2003-01-22 | Rolic AG | Photoactive materials |
| EP1386910A1 (en) * | 2002-07-30 | 2004-02-04 | Rolic AG | Photoactive materials |
| ES2444550T3 (es) * | 2002-08-29 | 2014-02-25 | Temple University - Of The Commonwealth System Of Higher Education | Arilpropenamidas y heteroarilpropenamidas, derivados de las mismas y usos terapéuticos de las mismas |
| KR100510133B1 (ko) * | 2003-02-08 | 2005-08-26 | 삼성전자주식회사 | 내광성 착색제 및 이를 포함하는 내광성 잉크 조성물 |
| WO2006039824A1 (en) * | 2004-10-13 | 2006-04-20 | Rolic Ag | Photocrosslinkable materials |
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- 2005-10-05 EP EP05786741.8A patent/EP1799791B1/en not_active Expired - Lifetime
- 2005-10-05 KR KR1020077008527A patent/KR101170417B1/ko not_active Expired - Fee Related
- 2005-10-05 JP JP2007535977A patent/JP5301834B2/ja not_active Expired - Fee Related
- 2005-10-05 US US11/665,351 patent/US7687118B2/en not_active Expired - Fee Related
- 2005-10-05 CN CN200580035070XA patent/CN101040028B/zh not_active Expired - Fee Related
- 2005-10-13 TW TW094135659A patent/TWI346691B/zh not_active IP Right Cessation
-
2012
- 2012-11-21 JP JP2012255226A patent/JP2013056924A/ja active Pending
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