JP4802479B2 - 重合性ビナフタレン誘導体 - Google Patents
重合性ビナフタレン誘導体 Download PDFInfo
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- JP4802479B2 JP4802479B2 JP2004319380A JP2004319380A JP4802479B2 JP 4802479 B2 JP4802479 B2 JP 4802479B2 JP 2004319380 A JP2004319380 A JP 2004319380A JP 2004319380 A JP2004319380 A JP 2004319380A JP 4802479 B2 JP4802479 B2 JP 4802479B2
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- ZDZHCHYQNPQSGG-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalene Chemical class C1=CC=C2C(C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 title description 14
- 150000001875 compounds Chemical class 0.000 claims description 203
- 239000004973 liquid crystal related substance Substances 0.000 claims description 92
- 229910052739 hydrogen Inorganic materials 0.000 claims description 89
- 239000001257 hydrogen Substances 0.000 claims description 89
- 239000000203 mixture Substances 0.000 claims description 86
- 230000003287 optical effect Effects 0.000 claims description 72
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 47
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 150000002367 halogens Chemical class 0.000 claims description 47
- -1 1,4-phenylene, naphthalene-2,6-diyl Chemical group 0.000 claims description 45
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 150000002431 hydrogen Chemical class 0.000 claims description 38
- 125000002947 alkylene group Chemical group 0.000 claims description 37
- 229920000642 polymer Polymers 0.000 claims description 36
- 229910052731 fluorine Inorganic materials 0.000 claims description 32
- 239000011737 fluorine Substances 0.000 claims description 32
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 31
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 30
- 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 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
- 229910052801 chlorine Inorganic materials 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 24
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 230000000379 polymerizing effect Effects 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 238000002983 circular dichroism Methods 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 230000001548 androgenic effect Effects 0.000 claims description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000010408 film Substances 0.000 description 23
- 239000010409 thin film Substances 0.000 description 19
- 125000005647 linker group Chemical group 0.000 description 17
- 239000007788 liquid Substances 0.000 description 17
- 229920000728 polyester Polymers 0.000 description 13
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 12
- 101150065749 Churc1 gene Proteins 0.000 description 12
- 102100038239 Protein Churchill Human genes 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 125000003709 fluoroalkyl group Chemical group 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
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- 238000000576 coating method Methods 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 230000035699 permeability Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
- 230000003098 cholesteric effect Effects 0.000 description 6
- 230000006870 function Effects 0.000 description 6
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 150000004714 phosphonium salts Chemical class 0.000 description 6
- 239000003505 polymerization initiator Substances 0.000 description 6
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 5
- 229920000297 Rayon Polymers 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
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- 238000002844 melting Methods 0.000 description 5
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- 238000000926 separation method Methods 0.000 description 5
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 229920002284 Cellulose triacetate Polymers 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 150000001345 alkine derivatives Chemical class 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 4
- 238000010538 cationic polymerization reaction Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 125000005755 decalin-2,6-ylene group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C([H])([*:2])C([H])([H])C([H])([H])C2([H])C([H])([H])C1([H])[*:1] 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- PPTXVXKCQZKFBN-UHFFFAOYSA-N (S)-(-)-1,1'-Bi-2-naphthol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 PPTXVXKCQZKFBN-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 101100184147 Caenorhabditis elegans mix-1 gene Proteins 0.000 description 3
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000007239 Wittig reaction Methods 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
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- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 description 2
- AQSCHALQLXXKKC-UHFFFAOYSA-N 4-phenylmethoxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OCC1=CC=CC=C1 AQSCHALQLXXKKC-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- ADIMYFQWTMLGKO-UHFFFAOYSA-N C(C)C1(COC1)COCCCCCCOC1=CC=C(C(=O)OC2=CC=C(C(=O)OC3=C(C4=CC=CC=C4C=C3)C3=CC=CC4=CC=CC=C34)C=C2)C=C1 Chemical compound C(C)C1(COC1)COCCCCCCOC1=CC=C(C(=O)OC2=CC=C(C(=O)OC3=C(C4=CC=CC=C4C=C3)C3=CC=CC4=CC=CC=C34)C=C2)C=C1 ADIMYFQWTMLGKO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
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- LNIBETQBUCYTBK-UHFFFAOYSA-N OC(C=C1)=CC=C1C(OC(C=CC1=CC=CC=C11)=C1C1=CC=CC2=CC=CC=C12)=O Chemical compound OC(C=C1)=CC=C1C(OC(C=CC1=CC=CC=C11)=C1C1=CC=CC2=CC=CC=C12)=O LNIBETQBUCYTBK-UHFFFAOYSA-N 0.000 description 2
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- 125000003545 alkoxy group Chemical group 0.000 description 2
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
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- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
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- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 1
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- 0 *C(CC1)CCC1[C@](CC1)CC[C@@]1C1COc2ccc(cccc3)c3c2-c(c2ccccc2cc2)c2OC1 Chemical compound *C(CC1)CCC1[C@](CC1)CC[C@@]1C1COc2ccc(cccc3)c3c2-c(c2ccccc2cc2)c2OC1 0.000 description 1
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- ZZCHCCHBSUTNBN-UHFFFAOYSA-N 1-(2-hydroxynaphthalen-1-yl)-3-[6-[4-(4-pentylcyclohexyl)phenoxy]hexyl]naphthalen-2-ol Chemical compound C(CCCC)C1CCC(CC1)C1=CC=C(C=C1)OCCCCCCC=1C(=C(C2=CC=CC=C2C1)C1=C(C=CC2=CC=CC=C12)O)O ZZCHCCHBSUTNBN-UHFFFAOYSA-N 0.000 description 1
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KODNTHAUOGOFJY-UHFFFAOYSA-N 2,4-diethylxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3OC2=C1 KODNTHAUOGOFJY-UHFFFAOYSA-N 0.000 description 1
- 125000005732 2,6-difluoro-1,4-phenylene group Chemical group [H]C1=C(F)C([*:1])=C(F)C([H])=C1[*:2] 0.000 description 1
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- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 1
- 125000005451 3-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C([H])=C(F)C([*:2])=C1[H] 0.000 description 1
- KUDDIVFYPCPVPX-UHFFFAOYSA-N 4-(4-phenylmethoxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C=C1)=CC=C1OCC1=CC=CC=C1 KUDDIVFYPCPVPX-UHFFFAOYSA-N 0.000 description 1
- ABEXKULSUJWUKU-UHFFFAOYSA-N 4-[2-(oxiran-2-yl)ethoxy]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OCCC1OC1 ABEXKULSUJWUKU-UHFFFAOYSA-N 0.000 description 1
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| JP4991737B2 (ja) | 2005-10-21 | 2012-08-01 | エルジー・ケム・リミテッド | 新規のビナフタレン誘導体、その製造方法およびそれを用いた有機電子素子 |
| JP5076414B2 (ja) * | 2005-11-29 | 2012-11-21 | Ｊｎｃ株式会社 | 重合性の光学活性化合物およびその組成物 |
| JP5332162B2 (ja) * | 2006-12-21 | 2013-11-06 | Ｊｎｃ株式会社 | 重合性液晶組成物 |
| JP5408841B2 (ja) * | 2006-12-29 | 2014-02-05 | 株式会社Ａｄｅｋａ | 重合性化合物及び重合性組成物 |
| JP5288156B2 (ja) * | 2007-09-28 | 2013-09-11 | Ｄｉｃ株式会社 | 重合性キラル化合物 |
| JP5202146B2 (ja) * | 2008-07-14 | 2013-06-05 | 日本化薬株式会社 | （メタ）アクリレート化合物及びそれを含有する活性エネルギー線硬化型樹脂組成物並びにその硬化物 |
| JP5493629B2 (ja) * | 2008-11-07 | 2014-05-14 | Ｊｎｃ株式会社 | 重合性液晶組成物 |
| JP5219084B2 (ja) * | 2009-02-18 | 2013-06-26 | 日本化薬株式会社 | 光学レンズシート用エネルギー線硬化型樹脂組成物及びその硬化物 |
| US8730435B2 (en) | 2009-07-17 | 2014-05-20 | Jnc Corporation | Liquid crystal display device having retardation film formed of liquid crystalline polyimide having photoreactive group |
| JP5803076B2 (ja) * | 2009-10-13 | 2015-11-04 | Jnc株式会社 | 重合性液晶化合物ならびにその重合体 |
| WO2011125684A1 (ja) * | 2010-03-31 | 2011-10-13 | Jsr株式会社 | 感放射線性樹脂組成物、レジストパターン形成方法、重合体及び化合物 |
| JP5962945B2 (ja) * | 2011-10-21 | 2016-08-03 | Dic株式会社 | 重合性キラル化合物 |
| US9360593B2 (en) | 2012-11-07 | 2016-06-07 | Mitsubishi Gas Chemical Company, Inc. | Polycarbonate resin, production method therefor, and optical molded body |
| CN105579488B (zh) * | 2013-09-26 | 2017-07-21 | 田冈化学工业株式会社 | 具有联萘骨架的环氧树脂 |
| CN110199008A (zh) * | 2017-03-17 | 2019-09-03 | 捷恩智株式会社 | 液晶组合物及液晶显示元件 |
| JP2019137713A (ja) * | 2018-02-06 | 2019-08-22 | 株式会社ダイセル | 熱硬化性組成物 |
| WO2022059648A1 (ja) * | 2020-09-16 | 2022-03-24 | ポリプラスチックス株式会社 | 熱硬化性組成物及びその硬化物並びにフィルム |
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| GB2298202B (en) * | 1995-02-24 | 1998-09-16 | Merck Patent Gmbh | Chiral polymerizable binaphthol derivatives |
| DE60118776T2 (de) * | 2000-10-04 | 2007-06-06 | Koninklijke Philips Electronics N.V. | Polymerisierbare, flüssigkristalline dioxetane, deren herstellung und verwendung |
| JP2004206102A (ja) * | 2002-12-12 | 2004-07-22 | Dainippon Printing Co Ltd | 配向膜組成物及びそれを用いた光学素子の製造方法 |
| JP2004206100A (ja) * | 2002-12-12 | 2004-07-22 | Dainippon Printing Co Ltd | 配向膜用組成物、配向膜の製造方法、及び光学素子の製造方法 |
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