JP5311054B2

JP5311054B2 - 液晶配向剤、液晶表示素子およびその製造方法

液晶配向剤、液晶表示素子およびその製造方法 Download PDF

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Publication number: JP5311054B2
Authority: JP; Japan
Prior art keywords: liquid crystal; group; aligning agent; crystal aligning; meth
Prior art date: 2009-02-19
Legal status : Active

Application number

JP2009277360A

Other languages

English (en)

Japanese (ja)

Other versions

JP2010217866A (ja

Inventor

純司吉澤

香織白土

Current Assignee

JSR Corp

Original Assignee

JSR Corp

Priority date

2009-02-19

Filing date

2009-12-07

Publication date

2013-10-09

2009-12-07 Application filed by JSR Corp filed Critical JSR Corp

2009-12-07 Priority to JP2009277360A priority Critical patent/JP5311054B2/ja

2010-09-30 Publication of JP2010217866A publication Critical patent/JP2010217866A/ja

2013-10-09 Application granted granted Critical

2013-10-09 Publication of JP5311054B2 publication Critical patent/JP5311054B2/ja

Status Active legal-status Critical Current

2029-12-07 Anticipated expiration legal-status Critical

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239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 341
239000003795 chemical substances by application Substances 0.000 title claims abstract description 89
238000004519 manufacturing process Methods 0.000 title claims description 37
150000001875 compounds Chemical class 0.000 claims abstract description 62
229920000642 polymer Polymers 0.000 claims abstract description 45
125000000962 organic group Chemical group 0.000 claims abstract description 15
-1 silane compound Chemical class 0.000 claims description 168
239000000758 substrate Substances 0.000 claims description 64
239000011248 coating agent Substances 0.000 claims description 52
238000000576 coating method Methods 0.000 claims description 52
210000002858 crystal cell Anatomy 0.000 claims description 50
229910000077 silane Inorganic materials 0.000 claims description 42
229920005575 poly(amic acid) Polymers 0.000 claims description 41
125000004432 carbon atom Chemical group C* 0.000 claims description 38
239000004642 Polyimide Substances 0.000 claims description 30
229920001721 polyimide Polymers 0.000 claims description 30
125000000217 alkyl group Chemical group 0.000 claims description 23
125000003118 aryl group Chemical group 0.000 claims description 13
230000001678 irradiating effect Effects 0.000 claims description 7
230000003301 hydrolyzing effect Effects 0.000 claims description 6
125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 2
125000003700 epoxy group Chemical group 0.000 claims description 2
238000000034 method Methods 0.000 abstract description 63
239000002253 acid Substances 0.000 abstract description 12
238000010438 heat treatment Methods 0.000 abstract description 7
229920001296 polysiloxane Polymers 0.000 abstract description 3
239000004952 Polyamide Substances 0.000 abstract description 2
229920002647 polyamide Polymers 0.000 abstract description 2
229920003055 poly(ester-imide) Polymers 0.000 abstract 1
239000000243 solution Substances 0.000 description 48
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 43
125000005595 acetylacetonate group Chemical group 0.000 description 37
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 33
238000003786 synthesis reaction Methods 0.000 description 29
230000015572 biosynthetic process Effects 0.000 description 28
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 23
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239000010936 titanium Substances 0.000 description 23
239000007983 Tris buffer Substances 0.000 description 21
239000003960 organic solvent Substances 0.000 description 21
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 20
229910052726 zirconium Inorganic materials 0.000 description 20
238000011156 evaluation Methods 0.000 description 18
125000006158 tetracarboxylic acid group Chemical group 0.000 description 18
239000002904 solvent Substances 0.000 description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
230000018044 dehydration Effects 0.000 description 14
238000006297 dehydration reaction Methods 0.000 description 14
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230000002194 synthesizing effect Effects 0.000 description 12
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238000002360 preparation method Methods 0.000 description 11
238000003860 storage Methods 0.000 description 11
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
238000007363 ring formation reaction Methods 0.000 description 9
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 8
239000004988 Nematic liquid crystal Substances 0.000 description 8
239000000853 adhesive Substances 0.000 description 8
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239000010410 layer Substances 0.000 description 7
150000004756 silanes Chemical class 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
239000011521 glass Substances 0.000 description 6
238000006358 imidation reaction Methods 0.000 description 6
230000007774 longterm Effects 0.000 description 6
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230000008569 process Effects 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
239000002994 raw material Substances 0.000 description 6
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XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 5
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
239000003822 epoxy resin Substances 0.000 description 5
VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 4
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 4
YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 description 4
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FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
229910006404 SnO 2 Inorganic materials 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
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125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
125000004391 aryl sulfonyl group Chemical group 0.000 description 4
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
238000005227 gel permeation chromatography Methods 0.000 description 4
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 4
150000002430 hydrocarbons Chemical group 0.000 description 4
150000003949 imides Chemical group 0.000 description 4
XAOGXQMKWQFZEM-UHFFFAOYSA-N isoamyl propanoate Chemical compound CCC(=O)OCCC(C)C XAOGXQMKWQFZEM-UHFFFAOYSA-N 0.000 description 4
229910001507 metal halide Inorganic materials 0.000 description 4
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150000007524 organic acids Chemical class 0.000 description 4
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
238000006798 ring closing metathesis reaction Methods 0.000 description 4
239000000565 sealant Substances 0.000 description 4
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150000005846 sugar alcohols Polymers 0.000 description 4
SGHZCASSRKVVCL-UHFFFAOYSA-N tri(butan-2-yloxy)-ethylsilane Chemical compound CCC(C)O[Si](CC)(OC(C)CC)OC(C)CC SGHZCASSRKVVCL-UHFFFAOYSA-N 0.000 description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 3
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 3
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JYCTWJFSRDBYJX-UHFFFAOYSA-N 5-(2,5-dioxooxolan-3-yl)-3a,4,5,9b-tetrahydrobenzo[e][2]benzofuran-1,3-dione Chemical compound O=C1OC(=O)CC1C1C2=CC=CC=C2C(C(=O)OC2=O)C2C1 JYCTWJFSRDBYJX-UHFFFAOYSA-N 0.000 description 3
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ITCGQBAPLXQYCA-UHFFFAOYSA-N 5-(2,5-dioxooxolan-3-yl)-8-methyl-3a,4,5,9b-tetrahydrobenzo[e][2]benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C2=CC(C)=CC=C2C1C1CC(=O)OC1=O ITCGQBAPLXQYCA-UHFFFAOYSA-N 0.000 description 3
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FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
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BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 3
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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 description 3
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PHPGKIATZDCVHL-UHFFFAOYSA-N trimethyl(propoxy)silane Chemical compound CCCO[Si](C)(C)C PHPGKIATZDCVHL-UHFFFAOYSA-N 0.000 description 3
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