CN109988536A - 显示器用封装剂 - Google Patents
显示器用封装剂 Download PDFInfo
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- CN109988536A CN109988536A CN201811523517.3A CN201811523517A CN109988536A CN 109988536 A CN109988536 A CN 109988536A CN 201811523517 A CN201811523517 A CN 201811523517A CN 109988536 A CN109988536 A CN 109988536A
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- Prior art keywords
- display
- encapsulant
- ingredient
- liquid crystal
- methyl
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- 239000008393 encapsulating agent Substances 0.000 title claims abstract description 81
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 65
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 239000004615 ingredient Substances 0.000 claims description 66
- -1 alcohol radical Chemical class 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 17
- 239000011256 inorganic filler Substances 0.000 claims description 11
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 11
- 239000007870 radical polymerization initiator Substances 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 9
- 150000002118 epoxides Chemical class 0.000 claims description 9
- 230000003287 optical effect Effects 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000012766 organic filler Substances 0.000 claims description 6
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical group CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 2
- 150000004693 imidazolium salts Chemical class 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 14
- 238000012360 testing method Methods 0.000 abstract description 9
- 230000008569 process Effects 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 230000006866 deterioration Effects 0.000 abstract 1
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- 238000004519 manufacturing process Methods 0.000 description 32
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- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical class COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 22
- 239000000758 substrate Substances 0.000 description 21
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- 239000000853 adhesive Substances 0.000 description 19
- 230000001070 adhesive effect Effects 0.000 description 19
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 19
- 239000003822 epoxy resin Substances 0.000 description 18
- 229920000647 polyepoxide Polymers 0.000 description 18
- 238000001723 curing Methods 0.000 description 16
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 14
- 239000004593 Epoxy Substances 0.000 description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 229940106691 bisphenol a Drugs 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 238000013007 heat curing Methods 0.000 description 7
- 239000000565 sealant Substances 0.000 description 7
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 7
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
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- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 5
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- 125000005843 halogen group Chemical group 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
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- 125000006850 spacer group Chemical group 0.000 description 5
- 238000001029 thermal curing Methods 0.000 description 5
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 150000001469 hydantoins Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- QDZXJOMXPRWGFG-UHFFFAOYSA-N CCC1=NC=NC=N1.O=C1NC(=O)NC(=O)N1 Chemical compound CCC1=NC=NC=N1.O=C1NC(=O)NC(=O)N1 QDZXJOMXPRWGFG-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229930192627 Naphthoquinone Natural products 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 229920000800 acrylic rubber Polymers 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 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 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 150000002791 naphthoquinones Chemical class 0.000 description 3
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 3
- LLEMOWNGBBNAJR-UHFFFAOYSA-N ortho-phenyl-phenol Natural products OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
- 150000003053 piperidines Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
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- 235000012222 talc Nutrition 0.000 description 3
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- MFEWNFVBWPABCX-UHFFFAOYSA-N 1,1,2,2-tetraphenylethane-1,2-diol Chemical compound C=1C=CC=CC=1C(C(O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(O)C1=CC=CC=C1 MFEWNFVBWPABCX-UHFFFAOYSA-N 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- QCBSYPYHCJMQGB-UHFFFAOYSA-N 2-ethyl-1,3,5-triazine Chemical compound CCC1=NC=NC=N1 QCBSYPYHCJMQGB-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
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- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
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- WWDJHYHOVFASKF-UHFFFAOYSA-N NNC(=O)CN1C(=O)NC(=O)NC1=O Chemical class NNC(=O)CN1C(=O)NC(=O)NC1=O WWDJHYHOVFASKF-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
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- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
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- 210000002858 crystal cell Anatomy 0.000 description 2
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- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- 229940005561 1,4-benzoquinone Drugs 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及显示器用封装剂。本发明的目的在于提供一种显示器用封装剂,其由热引起的反应快,在工序中对液晶的污染性极低,并且与取向膜等有机膜的胶粘性优良,另外,由耐湿可靠性试验引起的性能劣化少。一种显示器用封装剂,其含有:(A)在分子内具有与芳香环键合的羧基的化合物、(B)固化性化合物。
Description
技术领域
本发明涉及一种显示器用封装剂,其由热引起的反应快,在工序中对液晶的污染性极低,并且与取向膜等有机膜的胶粘性优良,另外,由耐湿可靠性试验引起的性能劣化少。
背景技术
关于显示器用封装剂,可以列举例如液晶显示器用密封剂、有机EL显示器用封装剂、触控面板用胶粘剂等。作为这些材料,共同点是,需要具有优良的固化性,并且不管被粘物如何都具有高胶粘性,而且耐湿热可靠性优良。
例如,以液晶密封剂为例,以下进行说明。
近年来,随着液晶显示元件的小型化,产生由于液晶显示元件的阵列基板的金属布线部分、滤色器基板的黑色矩阵部分而光照射不到液晶密封剂的遮光部,密封附近的显示不良的问题变得比以前更严重。即,由于存在遮光部而导致利用光进行的一次固化变得不充分,在液晶密封剂中残留大量未固化成分。在该状态下进行到利用热进行的二次固化工序的情况下,导致该未固化成分在液晶中的溶解由于热而被促进这样的结果,引起密封附近的显示不良。
为了解决该问题,进行了改良热反应性的各种各样的研究。存在如下尝试:在上述遮光部中,使利用光未充分固化的液晶密封剂从低温起迅速反应,以抑制液晶污染。例如,在专利文献1、2中公开了一种使用热自由基引发剂的方法。另外,在专利文献3~5中公开了一种使用多元羧酸作为固化促进剂的方法。
然而,在这些方法中,虽然热反应性提高,但是存在如下问题:所使用的热自由基引发剂、固化促进剂自身溶出到液晶中,引起显示不良。另外,在使用羧酸作为固化促进剂的情况下,产生如下问题:不并入固化体系的羧酸以原样的状态残留,使耐湿可靠性降低。
另外,由于近年来液晶面板的窄框化,因而将液晶密封剂描绘在取向膜上的情况变多,由于液晶密封剂与取向膜的胶粘性差,因而产生了液晶面板剥离这样的问题。以往一直使用的摩擦处理式的取向膜存在如下问题:由于在摩擦处理时发生的摩擦而导致产生异物或者液晶的取向变得不均匀,近年来正在进行从摩擦处理式的取向膜向光取向处理式的取向膜的变更,但是通常光取向处理式的取向膜与液晶密封剂的胶粘性弱,液晶面板剥离的问题变得显著。
为了解决液晶密封剂与取向膜的胶粘性的问题,提出了各种各样的技术。例如在专利文献6中提出了一种不使用无机填充剂的密封剂,但是未提及光取向处理式的取向膜。在专利文献7中提出了一种含有在一分子中具有3个以上环氧基的脂肪族环氧化合物等的密封材料,但是未提及光取向处理式的取向膜。
上述的固化性、耐湿可靠性、与不同的被粘物的胶粘性的问题不限于液晶密封剂,也被认为是显示器用封装剂的问题。
现有技术文献
专利文献
专利文献1:日本特开2004-126211号公报
专利文献2:日本特开2009-8754号公报
专利文献3:国际公开2007/138870
专利文献4:日本特开2008-15155号公报
专利文献5:日本特开2009-139922号公报
专利文献6:日本特开2010-85712号公报
专利文献7:日本特开2010-170069号公报
发明内容
发明所要解决的问题
本发明提出一种显示器用封装剂,其由热引起的反应快,在工序中对液晶的污染性极低,并且与取向膜等有机膜的胶粘性优良,另外,由耐湿可靠性试验引起的性能劣化少。
用于解决问题的手段
本发明人深入研究的结果发现,含有在分子内具有与芳香环键合的羧基的化合物的显示器用封装剂的热反应性优良,其结果是,可以抑制液晶污染性,而且胶粘性、耐湿热可靠性也优良,从而完成了本发明。
需要说明的是,本说明书中,在本说明书中“(甲基)丙烯酸”是指“丙烯酸”和/或“甲基丙烯酸”。
即,本发明涉及:
[1]一种显示器用封装剂,其含有:(A)在分子内具有与芳香环键合的羧基的化合物、(B)固化性化合物;
[2]根据前项[1]所述的显示器用封装剂,其中,所述成分(A)为还具有羧基、羟基、硫醇基的化合物;
[3]根据前项[1]或[2]所述的显示器用封装剂,其中,所述成分(B)为(B-1)(甲基)丙烯酸类化合物;
[4]根据前项[1]至[3]中任一项所述的显示器用封装剂,其中,所述成分(B)为成分(B-1)(甲基)丙烯酸类化合物与成分(B-2)环氧化合物的混合物;
[5]根据前项[1]至[4]中任一项所述的显示器用封装剂,其中,所述显示器用封装剂还含有(C)有机填料;
[6]根据前项[1]至[5]中任一项所述的显示器用封装剂,其中,所述显示器用封装剂还含有(D)无机填料;
[7]根据前项[1]至[6]中任一项所述的显示器用封装剂,其中,所述显示器用封装剂还含有(E)硅烷偶联剂;
[8]根据前项[1]至[7]中任一项所述的显示器用封装剂,其中,所述显示器用封装剂还含有(F)固化催化剂;
[9]根据前项[8]所述的显示器用封装剂,其中,所述成分(F)为咪唑化合物;
[10]根据前项[1]至[9]中任一项所述的显示器用封装剂,其中,所述显示器用封装剂还含有(G)光自由基聚合引发剂;
[11]根据前项[1]至[10]中任一项所述的显示器用封装剂,其中,所述显示器用封装剂还含有(H)热自由基聚合引发剂;
[12]一种液晶显示器,其通过利用前项[1]至[11]中任一项所述的显示器用封装剂进行封装而得到。
发明效果
对于本发明的显示器用封装剂而言,由于热固化时的反应速度快,因而即使在光难以到达的布线下也具有充分的固化性,因此可以确保面板的布线设计的自由度,可以容易地进行可靠性高的显示面板的制造。另外,与不同的被粘物的胶粘性、耐湿热可靠性也优良,因而也有助于显示器的长期可靠性。
具体实施方式
[(A)在分子内具有与芳香环键合的羧基的化合物]
本发明的显示器用封装剂含有(A)在分子内具有与芳香环键合的羧基的化合物(以下也简称为“成分(A)”)。该化合物与环氧基迅速地反应,因而不是作为固化促进剂发挥作用,而是作为固化剂发挥作用。因此,羧基不残留在体系中,不对耐湿可靠性产生不良影响。另外,其反应性高,固化物的交联密度高且耐热性优良,因而长期可靠性优良。
另外,通过与适当的固化催化剂并用,与丙烯酰基也发生反应。由此,可以使在布线遮光下无法进行光固化的丙烯酸类成分热固化,成为耐液晶污染性优良的封装剂。
关于成分(A),是指羧基与芳香环直接键合的成分。此处,芳香环是指:苯环、萘环、蒽环、菲环等、或噻吩环、呋喃环、吡咯环、噻唑环、唑环、吡唑环、咪唑环、异噻唑环、异唑环、吡唑环、噻二唑环、二唑环、三唑环、吡啶环、哒嗪环、嘧啶环和吡嗪环等杂环。从反应性的观点考虑,芳香环优选为苯环。
另外,该芳香环可以具有除上述羧基以外的取代基。作为该取代基,可以列举例如:卤素原子、另外的羧基、氨基甲酰基、磺基、氨基磺酰基、羟基、硫醇基、氨基、氰基、二氧磷基(ホスホ基)、膦基(ホスフィノ基)、氧膦基氧基(ホスフィニルオキシ基)、氧膦基氨基(ホスフィニルアミノ基)、硝基、甲硅烷基、酰基、C1~C6烷基(可以被选自卤素原子、羟基、羧基、氨基甲酰基、磺基和氨基磺酰基中的1个或2个以上取代基取代)、C1~C6烷氧基(可以被选自卤素原子、羟基、羧基、氨基甲酰基、磺基和氨基磺酰基中的1个或2个以上取代基取代)、C1~C6磺基烷基(可以被选自卤素原子、羟基、羧基、氨基甲酰基、磺基和氨基磺酰基中的1个或2个以上取代基取代)、C1~C6烷基硫基(可以被选自卤素原子、羟基、羧基、氨基甲酰基、磺基和氨基磺酰基中的1个或2个以上取代基取代)、C1~C6烷基氨基(可以被选自卤素原子、羟基、羧基、氨基甲酰基、磺基和氨基磺酰基中的1个或2个以上取代基取代)、或酰基氨基、芳氧基、杂环基、杂环氧基、芳基硫基、杂环硫基、芳基氨基、杂环氨基、芳基磺酰基、杂环磺酰基等。
这些取代基中,优选具有羧基、羟基、硫醇基的情况,进一步优选这些取代基与芳香环直接键合。这是因为,这些取代基可以与环氧基(根据情况也与(甲基)丙烯酰基)反应,提高固化物的交联密度。另外,从保存稳定性的观点考虑,优选羟基。
在除羧基以外的取代基为1个的情况下,其取代位置相对于羧基优选为邻位或对位,更优选为对位。在除羧基以外的取代基为2个的情况下,其取代位置优选为2,4-位。特别优选的是,除羧基以外的取代基为1个,其取代位置为对位。
需要说明的是,在本发明的显示器用封装剂中,在显示器用封装剂的总量中,成分(A)的配合量通常为0.1质量%~20质量%,优选为0.1质量%~10质量%,特别优选为0.5质量%~5质量%。
作为成分(A),可以例示出表1中所示的化合物。
表1
[(B)固化性化合物]
本发明的显示器用封装剂含有固化性化合物作为成分(B)(以下也简称为“成分(B)”)。
作为成分(B),只要是利用光、热等进行固化的化合物就没有特别限定,但是优选为成分(B-1)(甲基)丙烯酸类化合物(以下也简称为“成分(B-1)”)的情况。
此处“(甲基)丙烯酸”是指“丙烯酸”和/或“甲基丙烯酸”。(以下相同。)作为成分(B-1),可列举例如(甲基)丙烯酸酯化合物、环氧(甲基)丙烯酸酯化合物等。
[(B-1)(甲基)丙烯酸类化合物]
作为(甲基)丙烯酸酯化合物的具体例,可以列举:N-丙烯酰氧基乙基六氢邻苯二甲酰亚胺、丙烯酰基吗啉、(甲基)丙烯酸2-羟基丙酯、(甲基)丙烯酸4-羟基丁酯、环己烷-1,4-二甲醇单(甲基)丙烯酸酯、(甲基)丙烯酸四氢糠酯、(甲基)丙烯酸苯氧基乙酯、苯基聚乙氧基(甲基)丙烯酸酯、(甲基)丙烯酸2-羟基-3-苯氧基丙酯、邻苯基苯酚单乙氧基(甲基)丙烯酸酯、邻苯基苯酚聚乙氧基(甲基)丙烯酸酯、(甲基)丙烯酸对枯基苯氧基乙酯、(甲基)丙烯酸异冰片酯、(甲基)丙烯酸三溴苯氧基乙酯、(甲基)丙烯酸四氢二聚环戊二烯基酯、(甲基)丙烯酸二氢二聚环戊二烯基酯、(甲基)丙烯酸二氢二聚环戊二烯基氧基乙酯、1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、1,9-壬二醇二(甲基)丙烯酸酯、三环癸烷二甲醇(甲基)丙烯酸酯、双酚A聚乙氧基二(甲基)丙烯酸酯、双酚A聚丙氧基二(甲基)丙烯酸酯、双酚F聚乙氧基二(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、三(丙烯酰氧基乙基)异氰脲酸酯、季戊四醇四(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、三季戊四醇六(甲基)丙烯酸酯、三季戊四醇五(甲基)丙烯酸酯、三羟甲基丙烷三(甲基)丙烯酸酯、三羟甲基丙烷聚乙氧基三(甲基)丙烯酸酯、二(三羟甲基丙烷)四(甲基)丙烯酸酯、新戊二醇与羟基特戊酸的酯的二丙烯酸酯、新戊二醇与羟基特戊酸的酯的ε-己内酯加成物的二丙烯酸酯等单体类。优选地,可以列举N-丙烯酰氧基乙基六氢邻苯二甲酰亚胺、(甲基)丙烯酸苯氧基乙酯、(甲基)丙烯酸二氢二聚环戊二烯基氧基乙酯。
环氧(甲基)丙烯酸酯化合物可以通过环氧化合物与(甲基)丙烯酸的反应利用公知的方法得到。作为原料的环氧化合物没有特别限定,但是优选为双官能以上的环氧化合物,可列举例如:间苯二酚二缩水甘油基醚、双酚A型环氧化合物、双酚F型环氧化合物、双酚S型环氧化合物、苯酚酚醛清漆型环氧化合物、甲酚酚醛清漆型环氧化合物、双酚A酚醛清漆型环氧化合物、双酚F酚醛清漆型环氧化合物、脂环式环氧化合物、脂肪族链状环氧化合物、缩水甘油基酯型环氧化合物、缩水甘油基胺型环氧化合物、乙内酰脲型环氧化合物、异氰脲酸酯型环氧化合物、具有三羟苯基甲烷骨架的苯酚酚醛清漆型环氧化合物、以及邻苯二酚、间苯二酚等双官能酚类的二缩水甘油基醚化物、双官能醇类的二缩水甘油基醚化物、以及它们的卤化物、氢化物等。它们之中,从液晶污染性的观点考虑,优选双酚A型环氧化合物、间苯二酚二缩水甘油基醚。另外,环氧基与(甲基)丙烯酰基的比率没有限定,从工序适合性的观点考虑适当选择。需要说明的是,优选使用将环氧基的一部分进行丙烯酸酯化的部分环氧(甲基)丙烯酸酯。在该情况下的丙烯酸化的比例优选为约30%~约70%。
成分(B-1)可以单独使用,也可以将2种以上混合。在本发明的显示器用封装剂中,在使用成分(B-1)的情况下,在显示器用封装剂总量中,通常为5质量%~50质量%,优选为5质量%~30质量%。
[(B-2)环氧化合物]
作为本发明的方式,进一步优选在上述成分(B)中还含有成分(B-2)环氧化合物(以下也简称为“成分(B-2)”)的情况。
作为环氧化合物,没有特别限定,但是优选双官能以上的环氧化合物,可列举例如:间苯二酚二缩水甘油基醚、双酚A型环氧树脂、双酚F型环氧树脂、双酚S型环氧树脂、苯酚酚醛清漆型环氧树脂、甲酚酚醛清漆型环氧树脂、双酚A酚醛清漆型环氧树脂、双酚F酚醛清漆型环氧树脂、脂环式环氧树脂、脂肪族链状环氧树脂、缩水甘油基酯型环氧树脂、缩水甘油基胺型环氧树脂、乙内酰脲型环氧树脂、异氰脲酸酯型环氧树脂、具有三羟苯基甲烷骨架的苯酚酚醛清漆型环氧树脂、以及邻苯二酚、间苯二酚等双官能酚类的二缩水甘油基醚化物、双官能醇类的二缩水甘油基醚化物、以及它们的卤化物、氢化物等。它们之中,从液晶污染性的观点考虑,优选双酚A型环氧树脂、间苯二酚二缩水甘油基醚。
成分(B-2)可以单独使用,也可以将2种以上混合。在本发明的显示器用封装剂中,在使用成分(B-2)的情况下,在显示器用封装剂总量中,通常为5质量%~50质量%,优选为5质量%~30质量%。
需要说明的是,在本发明的显示器用封装剂中,在显示器用封装剂的总量中,成分(B)的配合量通常为10质量%~80质量%,优选为20质量%~70质量%。
[(C)有机填料]
本发明的显示器用封装剂可以含有有机填料作为成分(C)(以下也简称为“成分(C)”)。作为上述有机填料,可列举例如:聚氨酯微粒、丙烯酸类聚合物微粒、苯乙烯类聚合物微粒、苯乙烯-烯烃共聚物微粒以及聚硅氧烷微粒。需要说明的是,作为聚硅氧烷微粒,优选KMP-594、KMP-597、KMP-598(信越化学工业制造),TorayfilRTME-5500、9701、EP-2001(东丽道康宁公司制造),作为聚氨酯微粒,优选JB-800T、HB-800BK(根上工业株式会社),作为苯乙烯类聚合物微粒,优选RabalonRTMT320C、T331C、SJ4400、SJ5400、SJ6400、SJ4300C、SJ5300C、SJ6300C(三菱化学制造),作为苯乙烯-烯烃共聚物微粒,优选SEPTONRTMSEPS2004、SEPS2063。
这些有机填料可以单独使用,也可以并用2种以上。另外,也可以使用2种以上制成核壳结构。它们之中,优选丙烯酸类聚合物微粒、聚硅氧烷微粒。
在使用上述丙烯酸类聚合物微粒的情况下,优选为包含2种丙烯酸类橡胶的核壳结构的丙烯酸类橡胶的情况,特别优选为核层为丙烯酸正丁酯、壳层为甲基丙烯酸甲酯的丙烯酸类橡胶。其以ZefiacRTMF-351的形式由爱克工业株式会社销售。
另外,作为上述聚硅氧烷微粒,可列举有机聚硅氧烷交联物粉体、直链二甲基聚硅氧烷交联物粉体等。另外,作为复合硅橡胶,可列举在上述硅橡胶的表面被覆有聚硅氧烷树脂(例如,聚有机倍半硅氧烷树脂)的复合硅橡胶。这些微粒之中,特别优选的是,直链二甲基聚硅氧烷交联粉末的硅橡胶、或聚硅氧烷树脂被覆直链二甲基聚硅氧烷交联粉末的复合硅橡胶微粒。这些微粒可以单独使用,也可以并用2种以上。另外,优选地,对于橡胶粉末的形状而言,添加后的粘度的增加少的球形是良好的。在本发明的显示器用封装剂中,在使用成分(C)的情况下,在显示器用封装剂的总量中,通常为5质量%~50质量%,优选为5质量%~40质量%。
[(D)无机填料]
本发明的显示器用封装剂可以含有无机填料作为成分(D)(以下也简称为成分(D))。作为本发明中含有的无机填料,可列举:二氧化硅、碳化硅、氮化硅、氮化硼、碳酸钙、碳酸镁、硫酸钡、硫酸钙、云母、滑石、粘土、氧化铝、氧化镁、氧化锆、氢氧化铝、氢氧化镁、硅酸钙、硅酸铝、硅酸锂铝、硅酸锆、钛酸钡、玻璃纤维、碳纤维、二硫化钼、石棉等,优选地可列举:熔融二氧化硅、结晶二氧化硅、氮化硅、氮化硼、碳酸钙、硫酸钡、硫酸钙、云母、滑石、粘土、氧化铝、氢氧化铝、硅酸钙、硅酸铝,优选为二氧化硅、氧化铝、滑石。这些无机填料可以混合使用2种以上。
无机填料的平均粒径过大时,成为在制造窄间隙的液晶显示单元时无法良好地进行上下玻璃基板的贴合时的间隙形成等的不良因素,因而2000nm以下是适当的,优选为1000nm以下,进一步优选为300nm以下。另外,优选的下限为约10nm,进一步优选为约100nm。粒径可以利用激光衍射·散射式粒度分布测定器(干式)(株式会社清新企业制;LMS-30)进行测定。
在本发明的显示器用封装剂中,在使用无机填料的情况下,在显示器用封装剂的总量中,通常为5质量%~50质量%,优选为5质量%~40质量%。在无机填料的含量低于5质量%的情况下,对玻璃基板的胶粘强度降低,另外,耐湿可靠性差,因而有时吸湿后的胶粘强度的降低变大。另外,在无机填料的含量多于50质量%的情况下,由于填料含量过多,因而有时不易压溃,无法形成液晶单元的间隙。
[(E)硅烷偶联剂]
本发明的显示器用封装剂可以通过添加硅烷偶联剂作为成分(E)(以下也简称为“成分(E)”)而实现胶粘强度、耐湿性的提高。
作为成分(E),可列举:3-环氧丙氧基丙基三甲氧基硅烷、3-环氧丙氧基丙基甲基二甲氧基硅烷、3-环氧丙氧基丙基甲基二乙氧基硅烷、2-(3,4-环氧环己基)乙基三甲氧基硅烷、N-苯基-γ-氨基丙基三甲氧基硅烷、N-(2-氨基乙基)-3-氨基丙基甲基二甲氧基硅烷、N-(2-氨基乙基)-3-氨基丙基甲基三甲氧基硅烷、3-氨基丙基三乙氧基硅烷、3-巯基丙基三甲氧基硅烷、乙烯基三甲氧基硅烷、N-(2-(乙烯基苄基氨基)乙基)-3-氨基丙基三甲氧基硅烷盐酸盐、3-甲基丙烯酰氧基丙基三甲氧基硅烷、3-氯丙基甲基二甲氧基硅烷、3-氯丙基三甲氧基硅烷等。这些硅烷偶联剂以KBM系列、KBE系列等形式由信越化学工业株式会社等销售,因而可以容易从市场获得。在本发明的显示器用封装剂中,在使用成分(E)的情况下,在显示器用封装剂总量中,0.05质量%~3质量%是适合的。
[(F)固化催化剂]
本发明的显示器用封装剂可以通过添加固化催化剂作为成分(F)(以下也简称为“成分(F)”)而实现反应性的提高。如上所述,通过使用固化催化剂而使成分(A)与丙烯酰基也发生反应。因此,在丙烯酸类成分不进行光固化的情况下,发挥特别重要的作用。
作为固化催化剂,可以列举胺类、咪唑类,特别优选咪唑类。作为咪唑类,可列举:2-甲基咪唑、2-苯基咪唑、2-十一烷基咪唑、2-十七烷基咪唑、2-苯基-4-甲基咪唑、1-苄基-2-苯基咪唑、1-苄基-2-甲基咪唑、1-氰基乙基-2-甲基咪唑、1-氰基乙基-2-苯基咪唑、1-氰基乙基-2-十一烷基咪唑、2,4-二氨基-6-(2’-甲基咪唑(1’))乙基均三嗪、2,4-二氨基-6-(2’-十一烷基咪唑(1’))乙基均三嗪、2,4-二氨基-6-(2’-乙基-4-甲基咪唑(1’))乙基均三嗪、2,4-二氨基-6-(2’-甲基咪唑基(1’))乙基均三嗪·异氰脲酸加成物、2-甲基咪唑异氰脲酸的2:3加成物、2-苯基咪唑异氰脲酸加成物、2-苯基-3,5-二羟甲基咪唑、2-苯基-4-羟甲基-5-甲基咪唑、1-氰基乙基-2-苯基-3,5-二氰基乙氧基甲基咪唑等。它们之中,优选地可列举2,4-二氨基-6-(2’-甲基咪唑基(1’))乙基均三嗪·异氰脲酸加成物。
[(G)光自由基聚合引发剂]
本发明的显示器用封装剂可以含有光自由基聚合引发剂作为成分(G)(以下也简称为“成分(G)”)。作为光自由基聚合引发剂,只要是通过照射紫外线或可见光而产生自由基或酸并引发链式聚合反应的化合物,就没有特别限定,可以列举例如:苄基二甲基缩酮、1-羟基环己基苯基甲酮、二乙基噻吨酮、二苯甲酮、2-乙基蒽醌、2-羟基-2-甲基苯丙酮、2-甲基-[4-(甲硫基)苯基]-2-吗啉基-1-丙烷、2,4,6-三甲基苯甲酰基二苯基氧化膦、樟脑醌、9-芴酮、二苯基二硫醚等。具体地可以列举IRGACURERTM651、184、2959、127、907、369、379EG、819、784、754、500、OXE01、OXE02、DAROCURERTM1173、LUCIRINRTM TPO(均为巴斯夫公司制造),SEIKUOLRTMZ、BZ、BEE、BIP、BBI(均为精工化学株式会社制造)等。
另外,从液晶污染性的观点考虑,优选使用在分子内具有(甲基)丙烯酰基的光自由基聚合引发剂,例如优选使用2-甲基丙烯酰氧基乙基异氰酸酯与1-[4-(2-羟基乙氧基)苯基]-2-羟基-2-甲基-1-丙烷-1-酮的反应产物。该化合物可以利用国际公开第2006/027982号中记载的方法进行制造而得到。
在本发明的显示器用封装剂中,在使用成分(G)的情况下,在显示器用封装剂总量中,通常为0.001质量%~3质量%,优选为0.002质量%~2质量%。
[(H)热自由基聚合引发剂]
本发明的显示器用封装剂可以通过含有(H)热自由基聚合引发剂(以下也简称为“成分(H)”)而提高固化速度、固化性。
对于热自由基聚合引发剂而言,只要是通过加热而产生自由基并引发链式聚合反应的化合物就没有特别限定,可列举有机过氧化物、偶氮化合物、苯偶姻化合物、苯偶姻醚化合物、苯乙酮化合物、苯频哪醇等,优选使用苯频哪醇。例如,作为有机过氧化物,可以以市售品的形式获得KayamekRTMA、M、R、L、LH、SP-30C;Perkadox CH-50L、BC-FF;Cadox B-40ES;Perkadox 14;TrigonoxRTM22-70E、23-C70、121、121-50E、121-LS50E、21-LS50E、42、42LS;KayaesterRTMP-70、TMPO-70、CND-C70、OO-50E、AN;KayabutylRTMB;Perkadox 16;KayacarbonRTMBIC-75、AIC-75(日本化药AKZO株式会社制造);PermekRTMN、H、S、F、D、G;PerhexaRTMH、HC、TMH、C、V、22、MC;PercureRTMAH、AL、HB;PerbutylRTMH、C、ND、L;PercumylRTMH、D;PeroylRTMIB、IPP;PeroctaRTMND(日油株式会社制造)等。
另外,作为偶氮化合物,可以以市售品的形式获得VA-044、086、V-070、VPE-0201、VSP-1001(和光纯药工业株式会社制造)等。
作为成分(H)的含量,在本发明的显示器用封装剂的总量中,优选为0.0001质量%~10质量%,进一步优选为0.0005质量%~5质量%,特别优选为0.001质量%~3质量%。
在本发明的显示器用封装剂中,可以进一步根据需要配合自由基聚合抑制剂、除了成分(A)以外的热固化剂、颜料、流平剂、消泡剂、溶剂等添加剂。
[自由基聚合抑制剂]
作为上述自由基聚合抑制剂,只要是通过与由光自由基聚合引发剂或热自由基聚合引发剂等产生的自由基进行反应而抑制聚合的化合物就没有特别限定,可以使用醌类、哌啶类、受阻酚类、亚硝基类等。具体地可列举:萘醌、2-羟基萘醌、2-甲基萘醌、2-甲氧基萘醌、2,2,6,6-四甲基哌啶-1-氧基、2,2,6,6-四甲基-4-羟基哌啶-1-氧基、2,2,6,6-四甲基-4-甲氧基哌啶-1-氧基、2,2,6,6-四甲基-4-苯氧基哌啶-1-氧基、氢醌、2-甲基氢醌、2-甲氧基氢醌、对苯醌、丁基化羟基苯甲醚、2,6-二叔丁基-4-乙基苯酚、2,6-二叔丁基甲酚、β-(3,5-二叔丁基-4-羟基苯基)丙酸硬脂酯、2,2’-亚甲基双(4-乙基-6-叔丁基苯酚)、4,4’-硫代双(3-甲基-6-叔丁基苯酚)、4,4’-亚丁基双(3-甲基-6-叔丁基苯酚)、3,9-双[1,1-二甲基-2-[β-(3-叔丁基-4-羟基-5-甲基苯基)丙酰氧基]乙基]-2,4,8,10-四氧杂螺[5.5]十一烷、四[亚甲基-3-(3’,5’-二叔丁基-4’-羟基苯基)丙酸酯]甲烷、1,3,5-三(3’,5’-二叔丁基-4’-羟基苄基)均三嗪-2,4,6-(1H,3H,5H)三酮、对甲氧基苯酚、4-甲氧基-1-萘酚、硫代二苯基胺、N-亚硝基苯基羟胺的铝盐、商品名ADK STAB LA-81、商品名ADK STAB LA-82(株式会社艾迪科制造)等,但是不限定于这些。它们之中,优选萘醌类、氢醌类、亚硝基类、哌啶类的自由基聚合抑制剂,进一步优选萘醌、2-羟基萘醌、氢醌、2,6-二叔丁基对甲酚、Polystop7300P(伯东株式会社制造),最优选Polystop 7300P(伯东株式会社制造)。
作为自由基聚合抑制剂的含量,在本发明的显示器用封装剂的总量中,优选为0.0001质量%~1质量%,进一步优选为0.001质量%~0.5质量%,特别优选为0.01质量%~0.2质量%。
[除了成分(A)以外的热固化剂]
除了成分(A)以外的热固化剂是指利用非共用电子对或分子内的阴离子进行亲核反应的物质,可列举例如多元胺类、多元酚类、有机酸酰肼化合物等。但是不限定于这些。可列举例如:作为芳香族酰肼的对苯二甲酸二酰肼、间苯二甲酸二酰肼、2,6-萘甲酸二酰肼、2,6-吡啶二酰肼、1,2,4-苯三酰肼、1,4,5,8-萘甲酸四酰肼、均苯四酸四酰肼等。另外,如果是脂肪族酰肼化合物,则可列举例如:甲酰肼、乙酰肼、丙酰肼、草酸二酰肼、丙二酸二酰肼、琥珀酸二酰肼、戊二酸二酰肼、己二酸二酰肼、庚二酸二酰肼、癸二酸二酰肼、1,4-环己烷二酰肼、酒石酸二酰肼、苹果酸二酰肼、亚氨基二乙酸二酰肼、N,N’-六亚甲基双氨基脲、柠檬酸三酰肼、次氮基乙酸三酰肼、环己烷三甲酸三酰肼、1,3-双(肼基羰基乙基)-5-异丙基乙内酰脲等具有乙内酰脲骨架、优选缬氨酸乙内酰脲骨架(乙内酰脲环的碳原子被异丙基取代后的骨架)的二酰肼化合物、三(1-肼基羰基甲基)异氰脲酸酯、三(2-肼基羰基乙基)异氰脲酸酯、三(1-肼基羰基乙基)异氰脲酸酯、三(3-肼基羰基丙基)异氰脲酸酯、双(2-肼基羰基乙基)异氰脲酸酯等。从固化反应性与潜伏性的平衡考虑,优选为间苯二甲酸二酰肼、丙二酸二酰肼、己二酸二酰肼、三(1-肼基羰基甲基)异氰脲酸酯、三(1-肼基羰基乙基)异氰脲酸酯、三(2-肼基羰基乙基)异氰脲酸酯、三(3-肼基羰基丙基)异氰脲酸酯,特别优选为三(2-肼基羰基乙基)异氰脲酸酯。
除了成分(A)以外的热固化剂可以单独使用,也可以将2种以上混合。在本发明的显示器用封装剂中,在使用除了成分(A)以外的热固化剂的情况下,在显示器用封装剂总量中,通常为0.1质量%~10质量%,优选为0.1质量%~5质量%。
需要说明的是,对于本发明的显示器用封装剂而言,不包含酰肼类固化剂的情况是一个优选的方式。在此情况下,在显示器用封装剂总量中,酰肼类固化剂的含有率优选为1.0质量%以下,进一步优选实质上不含有的情况。
作为得到本发明的显示器用封装剂的方法的一个例子,有以下所示的方法。首先,在成分(B)中根据需要将成分(G)加热溶解。接着冷却至室温,然后添加成分(A)、根据需要的成分(C)、(D)、(E)、(F)、(H)、消泡剂、以及流平剂、溶剂等,利用公知的混合装置、例如三辊机、砂磨机、球磨机等均匀地混合,利用金属网进行过滤,由此可以制造本发明的显示器用封装剂。
另外,本发明的显示器用封装剂作为液晶显示单元用胶粘剂、特别是作为液晶密封剂非常有用。关于使用了本发明的显示器用封装剂作为液晶密封剂的情况下的液晶显示单元,以下示出例子。
使用本发明的液晶显示单元用胶粘剂制造的液晶显示单元通过以下方式得到:将在基板上形成有规定的电极的一对基板以规定的间隔相对配置,将周围利用本发明的液晶密封剂密封,在其间隙封入液晶。封入的液晶的种类没有特别限定。此处,基板由包含玻璃、石英、塑料、硅等且至少一者具有光透射性的组合基板构成。作为其制法,在本发明的液晶密封剂中添加玻璃纤维等间隔物(间隙控制材料),然后在该一对基板中的一者上使用分配器或者丝网印刷装置等涂布该液晶密封剂,然后根据需要在80℃~120℃下进行预固化。然后,在该液晶密封剂的围堰的内侧滴加液晶,在真空中重叠另一个玻璃基板,形成间隙。形成间隙后,在90℃~130℃下固化30分钟~2小时,由此可以得到本发明的液晶显示单元。另外,在以光热并用型的形式使用的情况下,利用紫外线照射机对液晶密封剂部照射紫外线而进行光固化。紫外线照射量优选为500mJ/cm2~6000mJ/cm2,更优选为1000mJ/cm2~4000mJ/cm2的照射量。然后,根据需要在90℃~130℃下固化30分钟~2小时,由此可以得到本发明的液晶显示单元。以这样的方式得到的本发明的液晶显示单元没有由液晶污染引起的显示不良,并且胶粘性、耐湿可靠性优良。作为间隔物,可列举例如玻璃纤维、二氧化硅微珠、聚合物微珠等。其直径根据目的而不同,通常为2μm~8μm,优选为4μm~7μm。相对于本发明的液晶密封剂100质量份,其使用量通常为约0.1质量份~约4质量份,优选为约0.5质量份~约2质量份,进一步优选为约0.9质量份~约1.5质量份。
本发明的显示器用封装剂非常适合用于要求固化性、与不同的被粘物的胶粘性、耐湿热可靠性的领域的胶粘剂用途。例如为液晶密封剂、有机EL用封装剂、触控面板用胶粘剂。
实施例
以下,通过实施例更详细地说明本发明,但是本发明并不限定于实施例。需要说明的是,除非另有说明,本文中“份”和“%”为质量基准。
[实施例1~9、比较例1]
按下述表1中所示的比例将成分(B)、(G)在90℃加热溶解,然后冷却至室温,添加成分(A)、(C)、(D)、(E)、(F)、(H),进行搅拌,然后利用三辊机进行分散,用金属网(635目)进行过滤,从而制备了显示器用封装剂的实施例1~9。另外,使用成分(O-4)来代替成分(A),制备了比较例1。
[评价]
[胶粘强度]
(初始胶粘强度坯玻璃(素ガラス))
在实施例和比较例中制造的液晶密封剂100g中添加作为间隔物的5μm的玻璃纤维1g并进行混合搅拌。将该液晶密封剂以复制1cm×1cm角部的方式涂布在玻璃基板上,贴合相对的玻璃基板并利用UV照射机照射3000mJ/cm2的紫外线,然后投入烘箱中并在120℃下热固化1小时。利用粘接试验仪(西进商事株式会社制造:SS-30WD)以按压角部的方式测定了该玻璃基板的剥离胶粘强度。将强度示于表2。
(初始胶粘强度 光取向膜)
将取向膜液(日产化学工业株式会社制造:RN2880)旋涂在玻璃基板上,利用80℃热板进行3分钟预烘,在230℃烘箱中烘烤30分钟。然后,利用UV照射机对该带有取向膜的基板照射500mJ/cm2(测定波长:254nm)的紫外线,然后在230℃烘箱中烘烤30分钟。
在实施例和比较例中制造的液晶密封剂100g中添加作为间隔物的5μm的玻璃纤维1g并进行混合搅拌。在涂布有取向膜的玻璃基板上以复制1cm×1cm角部的方式涂布该液晶密封剂,贴合相对的涂布有取向膜的基板并利用UV照射机照射3000mJ/cm2的紫外线,然后投入烘箱中并在120℃下热固化1小时。利用粘接试验仪(西进商事株式会社制造:SS-30WD)以按压角部的方式测定了该涂布有取向膜的玻璃基板的剥离胶粘强度。将强度示于表2。
(PCT后胶粘强度 光取向膜)
在上述涂布有取向膜的基板上涂布液晶密封剂,对固化后的试验片实施PCT试验(条件:温度121℃、湿度100%、气压2个大气压、试验时间12小时),同样地测定胶粘强度。将强度示于表2。
[玻璃化转变温度测定]
将实施例、比较例中制造的液晶密封剂夹在聚对苯二甲酸乙二醇酯(PET)膜之间并制成厚度100μm的薄膜,对于所得到的薄膜利用UV照射机照射3000mJ/cm2的紫外线,然后投入烘箱中并在120℃热固化1小时。固化后将PET膜剥离,从而得到密封剂固化膜,然后将其切割为50mm×5mm的短条状,从而制成样品片。利用动态粘弹性测定装置(DMS-6100:SIINanoTechnology公司制造)的拉伸模式在频率10Hz、升温温度3℃/分钟的条件下对该样品片进行测定,得到损耗系数Tanδ和将损耗系数Tanδ的曲线中达到最大值的温度作为玻璃化转变温度的结果。将结果示于表2。
[透湿度]
将实施例和比较例中制造的液晶密封剂夹在聚对苯二甲酸乙二醇酯(PET)膜之间并制成厚度100μm的薄膜,对于所得到的薄膜利用UV照射机照射3000mJ/cm2的紫外线,然后投入烘箱中在120℃热固化1小时,固化后将PET薄膜剥离,从而制成样品。利用透湿度测定仪(Lessy公司制造:L80-5000)测定样品的60℃、90%下的透湿度。将结果示于表2。
[电压保持率]
在带有透明电极的基板上涂布取向膜液(日产化学株式会社制造:NRB),进行烘烤,实施UV取向处理。按照在该基板上贴合所得到的液晶密封剂后的线宽为0.6mm的方式涂布主密封以及假密封(ダミーシール),接着将液晶(JC-5015LA:JNC株式会社制造)的微小液滴滴加在密封图案的框内。然后,在另一块经摩擦处理后的基板上散布面内间隔物(Natoco株式会社制造:Natoco Spacer KSEB-525F;贴合后的间隙宽度5μm),进行热固定,使用贴合装置在真空中贴合之前的滴加液晶后的基板。向大气敞开而形成间隙,然后仅对密封图案框内进行掩蔽并利用UV照射机照射100mJ/cm2的紫外线,然后投入烘箱中并在120℃热固化1小时,从而制成评价用液晶测试单元。利用液晶物性评价系统(东阳科技制造:6254型)测定所制成的评价用液晶单元在5V、1Hz、60℃条件下的电压保持率,将测定得到的结果示于表2。
表2
A-1:4-羟基苯甲酸
A-2:硫代水杨酸
A-3:对苯二甲酸
A-4:柠嗪酸
A-5:4-氨基苯甲酸
A-6:4-(氨基甲基)苯甲酸
A-7:2-巯基烟酸
B-1:双酚A型环氧丙烯酸酯(利用一般合成方法合成,例如日本特开2016-24243号公报)
B-2:双酚A型部分环氧丙烯酸酯(利用一般合成方法合成,例如在日本特开2016-24243号公报中按照50%当量进行反应)
B-3:EB3702(Daicel-Allnex株式会社制造)
B-4:EB3708(Daicel-Allnex株式会社制造)
B-5:双酚A型环氧树脂(RE310S:日本化药制造)
B-6:双酚S型环氧树脂(RE203:日本化药制造)
C-1:聚甲基丙烯酸酯类有机微粒(爱克工业株式会社制造:F-351S)
D-1:球形二氧化硅(德山株式会社制造:Sunseal SSP-07M)
E-1:3-环氧丙氧基丙基三甲氧基硅烷(JNC株式会社制造:Sila-Ace S-510)
F-1:2,4-二氨基-6-(2’-甲基咪唑基(1)’)乙基均三嗪·异氰脲酸加成物(四国化成制造:2MAOK-PW)
G-1:OXE04(巴斯夫公司制造)
H-1:1,2-双(三甲基甲硅烷氧基)-1,1,2,2-四苯基乙烷(由参考合成例2合成,粉碎成平均粒径1.9μm)
O-1:亚硝基类哌啶衍生物(伯东株式会社制造:Polystop 7300P)
O-2:三(2-肼基羰基乙基)异氰脲酸酯微粉碎品
O-3:丙二酸二酰肼(大塚化学制造)
O-4:三(2-羧基乙基)异氰脲酸酯(四国化成工业株式会社制造:CIC酸、利用气流粉碎机微粉碎成平均粒径1.5μm)
根据表1的结果可知,作为以往使用的酰肼固化体系的比较例1的电压保持率、玻璃化转变温度、胶粘强度均低,PCT后胶粘强度降低至初始值的一半。另一方面确认了,使用了成分(A)的实施例1~9在胶粘强度、玻璃化转变温度、透湿度、电压保持率的任一方面都优良。特别是,玻璃化转变温度和电压保持率与比较例1相比显著良好,确认了成分(A)的反应性高。
根据以上结果确认了,使用了成分(A)的本发明的显示器用封装剂的与有机膜的胶粘强度高,可以实现高可靠性。
产业实用性
本发明的显示器用封装剂的作业性优良,因而可以实现液晶显示单元的稳定生产,而且也有助于确保液晶显示单元的长期可靠性。
Claims (12)
1.一种显示器用封装剂,其含有:(A)在分子内具有与芳香环键合的羧基的化合物、(B)固化性化合物。
2.根据权利要求1所述的显示器用封装剂,其中,所述成分(A)为还具有羧基、羟基或硫醇基的化合物。
3.根据权利要求1或2所述的显示器用封装剂,其中,所述成分(B)为(B-1)(甲基)丙烯酸类化合物。
4.根据权利要求1至3中任一项所述的显示器用封装剂,其中,所述成分(B)为成分(B-1)(甲基)丙烯酸类化合物与成分(B-2)环氧化合物的混合物。
5.根据权利要求1至4中任一项所述的显示器用封装剂,其中,所述显示器用封装剂还含有(C)有机填料。
6.根据权利要求1至5中任一项所述的显示器用封装剂,其中,所述显示器用封装剂还含有(D)无机填料。
7.根据权利要求1至6中任一项所述的显示器用封装剂,其中,所述显示器用封装剂还含有(E)硅烷偶联剂。
8.根据权利要求1至7中任一项所述的显示器用封装剂,其中,所述显示器用封装剂还含有(F)固化催化剂。
9.根据权利要求8所述的显示器用封装剂,其中,所述成分(F)为咪唑化合物。
10.根据权利要求1至9中任一项所述的显示器用封装剂,其中,所述显示器用封装剂还含有(G)光自由基聚合引发剂。
11.根据权利要求1至10中任一项所述的显示器用封装剂,其中,所述显示器用封装剂还含有(H)热自由基聚合引发剂。
12.一种液晶显示器,其通过利用权利要求1至11中任一项所述的显示器用封装剂进行封装而得到。
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