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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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
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- 229920002959 polymer blend Polymers 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
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- 150000003254 radicals Chemical class 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
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- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims 1
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- 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
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- 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
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- JXQGICFGPUAVLJ-UHFFFAOYSA-N Cc1nnc(C)[s]1 Chemical compound Cc1nnc(C)[s]1 JXQGICFGPUAVLJ-UHFFFAOYSA-N 0.000 description 1
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| JP5301834B2 (ja) * | 2004-10-13 | 2013-09-25 | ロリク アーゲー | 光架橋性材料 |
| CN104649916B (zh) * | 2005-12-23 | 2020-12-01 | 罗利克有限公司 | 光可交联材料 |
| EP1801097A1 (en) * | 2005-12-23 | 2007-06-27 | Rolic AG | Photocrosslinkable materials |
| EP1860094A1 (en) * | 2006-05-23 | 2007-11-28 | 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 |
| JP5321839B2 (ja) * | 2007-04-25 | 2013-10-23 | 日産化学工業株式会社 | ポリイミド前駆体及びポリイミド並びに画像形成下層膜塗布液 |
| JP5077048B2 (ja) * | 2007-05-02 | 2012-11-21 | Ｊｓｒ株式会社 | 垂直配向型液晶配向剤 |
| KR101612699B1 (ko) * | 2007-05-02 | 2016-04-15 | 롤리크 아게 | 열안정성 정렬 물질 |
| KR101469572B1 (ko) * | 2007-05-25 | 2014-12-05 | 롤리크 아게 | 지환족 그룹을 포함하는 광가교결합 가능한 재료 |
| WO2009041708A1 (ja) * | 2007-09-26 | 2009-04-02 | Jsr Corporation | 液晶配向剤、液晶配向膜および液晶表示素子 |
| 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 |
| EP2222740B1 (en) * | 2007-12-21 | 2017-10-11 | Rolic AG | Functionalized photoreactive compounds |
| CN101903494B (zh) * | 2007-12-21 | 2016-03-02 | 罗利克有限公司 | 光校准组合物 |
| 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 |
| SI2384318T1 (en) | 2008-12-31 | 2018-03-30 | Ardelyx, Inc. | MEASURES AND PROCEDURES FOR THE INHIBITION OF ANTIPORT INHIBITED BY NHE IN THE TREATMENT OF DISEASES RELATED TO STRENGTH OF FLAMMABILITY OR TRADEMARITY WITH SOLO, AND THE EMISSION OF GASTROINTESTINAL TREATMENT |
| EP2463709A4 (en) * | 2009-07-08 | 2014-01-22 | Sharp Kk | Liquid crystal display panel and method of production thereof |
| WO2011074546A1 (ja) * | 2009-12-14 | 2011-06-23 | 日産化学工業株式会社 | 液晶配向処理剤及びそれを用いた液晶表示素子 |
| 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 |
| US9340634B2 (en) * | 2010-03-29 | 2016-05-17 | Dic Corporation | Polymer for use in liquid crystal alignment layer |
| 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 |
| KR101333711B1 (ko) | 2010-12-29 | 2013-11-27 | 제일모직주식회사 | 액정 배향제, 이를 이용하여 제조한 액정 배향막 및 상기 액정 배향막을 포함하는 액정표시소자 |
| KR101387736B1 (ko) * | 2010-12-29 | 2014-04-21 | 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 |
| JP6056752B2 (ja) * | 2011-03-31 | 2017-01-11 | 日産化学工業株式会社 | 液晶配向剤及びそれを用いた液晶配向膜 |
| JP6525590B2 (ja) | 2011-08-25 | 2019-06-05 | ロリク アーゲーＲｏｌｉｃ Ａｇ | 光反応性化合物 |
| WO2013050121A1 (en) * | 2011-10-03 | 2013-04-11 | Rolic Ag | Photoaligning materials |
| JP5939066B2 (ja) * | 2011-11-15 | 2016-06-22 | Jsr株式会社 | 液晶配向剤の製造方法 |
| CN105884641A (zh) * | 2011-11-17 | 2016-08-24 | 国立研究开发法人科学技术振兴机构 | 化合物及其制造方法 |
| 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 |
| JP6146577B2 (ja) * | 2011-12-28 | 2017-06-14 | 日産化学工業株式会社 | 液晶配向剤、液晶配向膜及び液晶表示素子 |
| 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 |
| US10557085B2 (en) | 2015-03-31 | 2020-02-11 | Rolic Ag | Photoalignment composition |
| 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 |
| TWI747863B (zh) * | 2015-12-25 | 2021-12-01 | 日商日產化學工業股份有限公司 | 液晶顯示元件、液晶光學元件及液晶構造體安定化膜用組成物 |
| 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 |
| WO2020128729A1 (en) * | 2018-12-19 | 2020-06-25 | 3M Innovative Properties Company | Release layers and articles containing them |
| 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 |
| WO1999015576A1 (en) | 1997-09-25 | 1999-04-01 | Rolic Ag | Photocrosslinkable polyimides |
| WO1999049360A1 (en) | 1998-03-20 | 1999-09-30 | Rolic Ag | LlQUID CRYSTAL ORIENTATION LAYER |
| WO1999051662A1 (en) * | 1998-04-01 | 1999-10-14 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Polyimide compositions |
| US6194472B1 (en) | 1998-04-02 | 2001-02-27 | Akzo Nobel N.V. | Petroleum hydrocarbon in water colloidal dispersion |
| EP1261659B1 (en) * | 2000-01-24 | 2004-10-06 | 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 |
| AU2003298567B9 (en) * | 2002-08-29 | 2009-07-23 | Temple University - Of The Commonwealth System Of Higher Education | Aryl and heteroaryl propene amides, derivatives thereof and therapeutic uses thereof |
| KR100510133B1 (ko) * | 2003-02-08 | 2005-08-26 | 삼성전자주식회사 | 내광성 착색제 및 이를 포함하는 내광성 잉크 조성물 |
| JP5301834B2 (ja) * | 2004-10-13 | 2013-09-25 | ロリク アーゲー | 光架橋性材料 |
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- 2005-10-05 KR KR1020077008527A patent/KR101170417B1/ko not_active Expired - Fee Related
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