CN104487474B - 树脂组合物 - Google Patents
树脂组合物 Download PDFInfo
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- CN104487474B CN104487474B CN201380039675.0A CN201380039675A CN104487474B CN 104487474 B CN104487474 B CN 104487474B CN 201380039675 A CN201380039675 A CN 201380039675A CN 104487474 B CN104487474 B CN 104487474B
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- Prior art keywords
- resin combination
- organic
- group
- moisture
- sulfonium
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- 229920005989 resin Polymers 0.000 title claims abstract description 101
- 239000011347 resin Substances 0.000 title claims abstract description 101
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 33
- 239000003822 epoxy resin Substances 0.000 claims abstract description 31
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000000460 chlorine Substances 0.000 claims abstract description 23
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 23
- 239000012952 cationic photoinitiator Substances 0.000 claims abstract description 14
- 150000002118 epoxides Chemical class 0.000 claims abstract 3
- -1 ether compound Chemical class 0.000 claims description 140
- 238000000034 method Methods 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 44
- 239000000463 material Substances 0.000 claims description 22
- 239000004593 Epoxy Substances 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 239000007767 bonding agent Substances 0.000 claims description 16
- 238000007789 sealing Methods 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 239000003381 stabilizer Substances 0.000 claims description 12
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 11
- 229910000077 silane Inorganic materials 0.000 claims description 11
- 238000007711 solidification Methods 0.000 claims description 9
- 230000008023 solidification Effects 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 7
- 239000000565 sealant Substances 0.000 claims description 7
- 239000005062 Polybutadiene Substances 0.000 claims description 5
- 229920002857 polybutadiene Polymers 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 238000004108 freeze drying Methods 0.000 claims description 2
- 230000035699 permeability Effects 0.000 abstract description 11
- 239000011248 coating agent Substances 0.000 abstract description 6
- 238000000576 coating method Methods 0.000 abstract description 6
- 239000011342 resin composition Substances 0.000 abstract description 4
- 238000003860 storage Methods 0.000 abstract description 3
- 239000002585 base Substances 0.000 description 86
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 67
- 229910052799 carbon Inorganic materials 0.000 description 67
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 41
- 125000000217 alkyl group Chemical group 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
- 239000000126 substance Substances 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 18
- 229910052711 selenium Inorganic materials 0.000 description 16
- 239000011669 selenium Substances 0.000 description 16
- 125000001544 thienyl group Chemical group 0.000 description 16
- 239000002245 particle Substances 0.000 description 15
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
- 150000003983 crown ethers Chemical class 0.000 description 10
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- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 9
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 9
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- 230000000052 comparative effect Effects 0.000 description 7
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 238000000016 photochemical curing Methods 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 230000001235 sensitizing effect Effects 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 7
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001723 curing Methods 0.000 description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- LTYMSROWYAPPGB-UHFFFAOYSA-O diphenylsulfanium Chemical compound C=1C=CC=CC=1[SH+]C1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-O 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 150000003568 thioethers Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- 239000005864 Sulphur Substances 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 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 5
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 5
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- UDHAWRUAECEBHC-UHFFFAOYSA-N 1-iodo-4-methylbenzene Chemical compound CC1=CC=C(I)C=C1 UDHAWRUAECEBHC-UHFFFAOYSA-N 0.000 description 4
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 4
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
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- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
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- 150000002391 heterocyclic compounds Chemical class 0.000 description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
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- FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 description 3
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- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 3
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
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- NYWSOZIZKAROHJ-UHFFFAOYSA-N 5-phenylthianthren-5-ium Chemical compound C12=CC=CC=C2SC2=CC=CC=C2[S+]1C1=CC=CC=C1 NYWSOZIZKAROHJ-UHFFFAOYSA-N 0.000 description 2
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- 125000003003 spiro group Chemical group 0.000 description 1
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- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
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- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
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- AXYQQAVHPAUFQX-UHFFFAOYSA-N tris(2-methylphenyl)sulfanium Chemical compound CC1=CC=CC=C1[S+](C=1C(=CC=CC=1)C)C1=CC=CC=C1C AXYQQAVHPAUFQX-UHFFFAOYSA-N 0.000 description 1
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- 238000005303 weighing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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Abstract
本发明提供一种树脂组合物,其含有(A)环氧化合物、(B)环氧树脂、(C)阳离子聚合光引发剂。优选该树脂组合物的水分量为1000ppm以下、氯量为1000ppm以下。该树脂组合物是高精度的涂布性、粘接性、低透湿性、粘接耐久性、保存稳定性优异的能量线固化性树脂组合物。
Description
技术领域
本发明涉及树脂组合物。例如,涉及可用于有机EL元件密封用的粘接剂及固化物。
背景技术
有机EL元件作为能高亮度发光的元件体而备受瞩目。然而,存在因水分而发生劣化、发光特性会降低的课题。
为了解决上述课题,正在研究对有机EL元件进行密封来防止由水分导致的劣化的技术。例如,可举出用由烧结玻璃(fritted glass)形成的密封材料进行密封的方法(参照专利文献1)。
另外,提出了不仅对基材周部进行密封、而且填充基板的层间并使其粘贴的密封方法。在这种情况下,提出了填充层间的树脂组合物(参照专利文献2、专利文献3)。
此外,还提出了满足固化性、粘接性、贮藏稳定性的能量射线固化性树脂组合物(专利文献4)。
需要说明的是,作为用于其它目的的树脂组合物,专利文献5~7中还记载有各种树脂组合物。
另外,在有机EL的密封技术中,记载了将有机EL元件密封用的由(通过紫外线照射不固化的)热固化性树脂材料形成的填充层的含水率设定为0.01wt%以下(专利文献8)。另外,专利文献8中还记载了将有机EL元件密封用的由紫外线固化性树脂材料形成的周边密封层的含水率设定为0.1wt%以下。
需要说明的是,作为用于其它目的的树脂组合物,专利文献9中记载了水解性氯的含量为100ppm以下的感光性添加粘接剂。另外,专利文献10中记载了水解性氯量为600ppm以下的液晶密封剂。
另外,在有机EL的密封技术中,记载了在有机EL元件用的密封剂中添加冠醚(专利文献11)。另外,作为用于其它目的的树脂组合物,记载了在触控面板用光固化性树脂组合物中添加冠醚(专利文献12)。
专利文献1:日本特开平10-74583号公报
专利文献2:日本特开2005-336314号公报
专利文献3:日本特开2008-59945号公报
专利文献4:日本特开2010-248500号公报
专利文献5:日本特开2009-286954号公报
专利文献6:日本特表2010-507696号公报
专利文献7:日本特开2001-181221号公报
专利文献8:日本特开2008-59868号公报
专利文献9:日本特开平10-173336号公报
专利文献10:日本特开2004-61925号公报
专利文献11:日本特开2012-151109号公报
专利文献12:日本特开2011-111598号公报
发明内容
发明要解决的问题
然而,上述文献记载的现有技术在以下方面尚有改善的余地。
在专利文献1中,在进行批量生产时,采用将有机EL元件插入水分透过性低的基材、例如玻璃等中来密封外周部的方法。在这种情况下,由于该结构成为中空密封结构,因此,不能防止水分浸入中空密封结构内部,存在导致有机EL元件劣化的课题。
在专利文献2及3中,由于这些树脂组合物的水分透过性高,因此会使有机EL元件劣化,并且因无法确保充分的粘接力而存在有机EL元件剥离的课题。另外,由于在有机EL元件上蒸镀金属,因此,存在因金属腐蚀而导致有机EL元件劣化的课题。
在专利文献4中,存在如下课题:在不选择双-(4-叔丁基-苯基)-碘鎓-三(三氟甲烷磺酰基)甲基化物等特定种类的光聚合引发剂的情况下,使用多种光聚合引发剂大范围地研究有机EL元件密封用的树脂组合物的成分组成等是困难的。
专利文献5~7原本是用于其它目的的树脂组合物,对限定水分量也没有记载。
专利文献8虽然限定了水分量,但由于组合包含以碳和氢为主要成分的烯烃树脂或环状烯烃树脂的外涂层、包含(通过紫外线照射不固化的)环氧系的热固化性树脂材料的填充层、和包含环氧系紫外线固化性树脂材料的周边密封层,因此,存在粘接性、粘接耐久性等不充分、有机EL元件的密封工序复杂之类的课题。
专利文献9~10虽然分别限定了氯量,但原本是用于其它目的的树脂组合物,对限定水分量也没有记载。
专利文献11~12记载了在有机EL元件用的密封剂或触控面板用光固化性树脂组合物中添加冠醚,但对限定水分量也没有记载。
本发明是鉴于上述情况而完成的,目的在于提供一种在用于有机EL元件密封用的情况下不容易使有机EL元件劣化的树脂组合物。
用于解决问题的方案
本发明为一种树脂组合物,其含有(A)环氧化合物、(B)环氧树脂、和(C)阳离子聚合光引发剂,并且水分量为1000ppm以下、氯量为1000ppm以下。该树脂组合物在用于有机EL元件密封用的情况下不容易使有机EL元件劣化。
需要说明的是,上述树脂组合物是本发明的一个方式,本发明的粘接剂、有机EL元件用密封剂、固化物、有机EL装置、显示器、它们的制造方法等也具有同样的构成及效果。
发明的效果
根据本发明,可以抑制有机EL元件劣化。
具体实施方式
<术语说明>
在本说明书中,能量射线固化性树脂组合物是指通过照射能量射线能使其固化的树脂组合物。这里,能量射线是指以紫外线、可见光线等为代表的能量射线。
在本说明书中,符号“~”是指两端的值“以上”及“以下”的范围。例如,“A~B”是指为A以上且为B以下。
下面,对本发明的实施方式详细地进行说明。
[实施方式1:树脂组合物]
作为本实施方式的树脂组合物,优选能量射线固化性树脂组合物。能量射线固化性树脂组合物含有(A)环氧化合物、(B)环氧树脂、(C)阳离子聚合光引发剂、(D)光敏剂。
下面,对本实施方式的树脂组合物的成分进行说明。
((A)环氧化合物)
本实施方式的树脂组合物含有(A)环氧化合物。通过使用环氧化合物,本实施方式的树脂组合物显示出优异的粘接性、低透湿性、粘接耐久性。
作为(A)环氧化合物的脂环式环氧化合物,可举出:通过用过氧化氢、高酸等适当的氧化剂将具有至少1个环己烯或环戊烯环、蒎烯环等环烯烃环的化合物进行环氧化而得到的化合物或者其衍生物;将双酚A型环氧化合物等芳香族环氧化合物氢化而得到的氢化环氧化合物等脂环式环氧化合物等。这些化合物可以选择1种或2种以上来使用。
对于环氧化合物的分子量,在透湿性方面,优选低于300、更优选为100~280。分子量是指数均分子量。分子量使用通过GPC(凝胶渗透色谱法)进行测定而得到的聚苯乙烯换算的数均分子量。例如,在以下条件下进行测定。
溶剂(流动相):THF
脱气装置:ERMA公司制ERC-3310
泵:日本分光公司制PU-980
流速1.0ml/min
自动进样器:Tosoh Corporation制AS-8020
柱温箱:日立制作所制L-5030
设定温度40℃
柱构成:2根Tosoh Corporation制TSKguardcolumn MP(×L)6.0mmID×4.0cm、及2根Tosoh Corporation制TSK-GELMULTIPORE HXL-M7.8mmID×30.0cm,共4根
检测器:RI日立制作所制L-3350
数据处理:SIC480数据站
其中,在粘接性、光固化性优异方面,优选为脂环式环氧化合物,更优选为1分子内含有1个以上环氧基和1个以上酯基的脂环式环氧化合物。
作为脂环式环氧化合物,没有特别限制,可举出:3,4-环氧环己烯基甲基-3’,4’-环氧环己烯甲酸酯、3,4-环氧环己基甲基(甲基)丙烯酸酯等之类的1分子内具有1个以上环氧基和1个以上酯基的脂环式环氧化合物、二环戊二烯型环氧化合物等。
((B)环氧树脂)
作为(B)环氧树脂,没有特别限制,可举出:环氧化聚丁二烯树脂、具有环己基的环氧树脂、双酚A型环氧树脂、双酚F型环氧树脂、双酚S型环氧树脂、联苯型环氧树脂、萘型环氧树脂、芴型环氧树脂、苯酚酚醛清漆型环氧树脂、甲酚酚醛清漆型环氧树脂、它们的改性物等。这些环氧树脂可以选择1种或2种以上来使用。其中,在粘接性、光固化性优异方面,优选为不具有芳香族基团的环氧树脂。在不具有芳香族基团的环氧树脂中,在粘接性、光固化性优异方面,优选为由含有环己基的环氧树脂和环氧化聚丁二烯树脂组成的组中的1种或2种以上,更优选为环氧化聚丁二烯树脂。
对于环氧树脂的分子量,在透湿性方面,优选为300~5000。这里,分子量是指数均分子量。分子量使用通过GPC(凝胶渗透色谱法)进行测定而得到的聚苯乙烯换算的数均分子量。
对于(B)成分的用量,在操作性、光固化性、粘接性、透湿性、粘接耐久性方面,在(A)与(B)的合计100质量份中,优选为0.5质量份以上、更优选为1质量份以上、更加优选为3质量份以上、最优选为5质量份以上。对于(B)成分的用量,在操作性、光固化性、粘接性、透湿性、粘接耐久性方面,在(A)与(B)的合计100质量份中,优选为50质量份以下、优选为30质量份以下、优选为25质量份以下、最优选为20质量份以下。
((C)阳离子聚合光引发剂)
本实施方式的树脂组合物含有(C)阳离子聚合光引发剂。在使用阳离子聚合光引发剂的情况下,本实施方式的树脂组合物可以通过紫外线等能量射线照射而固化。
作为(C)阳离子聚合光引发剂,没有特别限制,可举出:芳基锍盐衍生物(例如,DowChemical Company制的Cyracure UVI-6990、Cyracure UVI-6974、旭电化工业公司制的Adeka Optomer SP-150、Adeka Optomer SP-152、Adeka Optomer SP-170、Adeka OptomerSP-172、San-Apro Ltd.制的CPI-100P、CPI-101A、CPI-200K、CPI-210S、LW-S1、Double BondChemical Ind Co.Ltd.制的Chivacure 1190等)、芳基碘鎓盐衍生物(例如,CibaSpecialty Chemicals Inc.制的Irgacure 250、Rhodia Japan公司制的RP-2074)、丙二烯-离子络合物衍生物、重氮鎓盐衍生物、三嗪系引发剂及其它卤化物等产酸剂等。作为阳离子聚合光引发剂的阳离子物质,优选下式(1)所示的鎓盐。
作为(C)阳离子聚合光引发剂,没有特别限制,可举出下式(1)所示的鎓盐。
(化学式1)
(A为VIA族~VIIA族的原子价m的元素。m=1~2。n=0~3。m、n优选为整数。R表示键合于A的有机基团。D为下式(2)所示的结构,
(化学式2)
式(2)中,E表示2价的基团,G为-O-、-S-、-SO-、-SO2-、-NH-、-NR’-、-CO-、-COO-、-CONH-、碳原子数1~3的亚烷基或亚苯基(R’为碳原子数1~5的烷基或碳原子数6~10的芳基)。a=0~5。a+1个E及a个G分别可以相同也可以不同。a优选为整数。这里,R’与前述的R’相同。X-为鎓的抗衡离子,其个数为每1分子为n+1。)
对式(1)的化合物的鎓离子没有特别限制,可举出:4-(苯硫基)苯基二苯基锍、双[4-(二苯基锍基)苯基]硫醚、双〔4-{双[4-(2-羟基乙氧基)苯基]锍基}苯基〕硫醚、双{4-[双(4-氟苯基)锍基]苯基}硫醚、4-(4-苯甲酰基-2-氯苯硫基)苯基双(4-氟苯基)锍、4-(4-苯甲酰基苯硫基)苯基二苯基锍、7-异丙基-9-氧代-10-硫杂-9,10-二氢蒽-2-基二对甲苯基锍、7-异丙基-9-氧代-10-硫杂-9,10-二氢蒽-2-基二苯基锍、2-[(二对甲苯基)锍基]噻吨酮、2-[(二苯基)锍基]噻吨酮、4-[4-(4-叔丁基苯甲酰基)苯硫基]苯基二对甲苯基锍、4-(4-苯甲酰基苯硫基)苯基二苯基锍、5-(4-甲氧基苯基)噻蒽鎓(thianthrenium)、5-苯基噻蒽鎓、二苯基苯甲酰甲基锍、4-羟基苯基甲基苄基锍、2-萘基甲基(1-乙氧羰基)乙基锍、4-羟基苯基甲基苯甲酰甲基锍、十八烷基甲基苯甲酰甲基锍等。
R为键合于A的有机基团,表示碳原子数6~30的芳基、碳原子数4~30的杂环基、碳原子数1~30的烷基、碳原子数2~30的烯基或碳原子数2~30的炔基,这些基团可以用选自由烷基、羟基、烷氧基、烷基羰基、芳基羰基、烷氧羰基、芳氧羰基、芳硫羰基、酰氧基、芳硫基、烷硫基、芳基、杂环、芳氧基、烷基亚磺酰基、芳基亚磺酰基、烷基磺酰基、芳基磺酰基、亚烷基氧基、氨基、氰基、硝基的各基团及卤素组成的组中的至少1种取代。R的个数为m+n(m-1)+1,分别可以彼此相同,也可以不同。另外,2个以上的R可以彼此直接或借助-O-、-S-、-SO-、-SO2-、-NH-、-NR’-、-CO-、-COO-、-CONH-、碳原子数1~3的亚烷基或者亚苯基键合而形成包含元素A的环结构。在此,R’为碳原子数1~5的烷基或碳原子数6~10的芳基。
上述中作为碳原子数6~30的芳基,可举出:苯基等单环式芳基及萘基、蒽基、菲基、芘基、基、并四苯基、苯并蒽基、蒽醌基、芴基、萘醌基、蒽醌基等稠环式芳基。
作为碳原子数4~30的杂环基,可举出包含1~3个氧、氮、硫等杂原子的环状基团,这些基团可以相同,也可以不同,作为具体例,可举出:噻吩基、呋喃基、吡喃基、吡咯基、噁唑基、噻唑基、吡啶基、嘧啶基、吡嗪基等单环式杂环基及吲哚基、苯并呋喃基、异苯并呋喃基、苯并噻吩基、异苯并噻吩基、喹啉基、异喹啉基、喹喔啉基、喹唑啉基、咔唑基、吖啶基、吩噻嗪基、吩嗪基、呫吨基、噻蒽基、吩噁嗪基、吩噁噻基、色满基、异色满基、二苯并噻吩基、呫吨酮基、噻吨酮基、二苯并呋喃基等稠环式杂环基。
作为碳原子数1~30的烷基,可举出:甲基、乙基、丙基、丁基、戊基、辛基、癸基、十二烷基、十四烷基、十六烷基、十八烷基等直链烷基;异丙基、异丁基、仲丁基、叔丁基、异戊基、新戊基、叔戊基、异己基等支链烷基;环丙基、环丁基、环戊基、环己基等环烷基;苄基、萘基甲基、蒽基甲基、1-苯基乙基、2-苯基乙基那样的芳烷基等。另外,作为碳原子数2~30的烯基,可举出:乙烯基、烯丙基、1-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-1-丙烯基、1-甲基-2-丙烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-1-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1,2-二甲基-1-丙烯基、1-癸烯基、2-癸烯基、8-癸烯基、1-十二碳烯基、2-十二碳烯基、10-十二碳烯基等直链或支链状的烯基;2-环己烯基、3-环己烯基等环烯基;或者苯乙烯基、肉桂基那样的芳基烯基等。进而,作为碳原子数2~30的炔基,可举出:乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、1,1-二甲基-2-丙炔基、1-戊炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-癸炔基、2-癸炔基、8-癸炔基、1-十二炔基、2-十二炔基、10-十二炔基等直链状或支链状的炔基或者苯基乙炔基等芳基炔基等。
上述碳原子数6~30的芳基、碳原子数4~30的杂环基、碳原子数1~30的烷基、碳原子数2~30的烯基或碳原子数2~30的炔基可以具有至少1种取代基,作为取代基的例子,可举出:甲基、乙基、丙基、丁基、戊基、辛基、癸基、十二烷基、十四烷基、十六烷基、十八烷基等碳原子数1~18的直链烷基;异丙基、异丁基、仲丁基、叔丁基、异戊基、新戊基、叔戊基、异己基等碳原子数1~18的支链烷基;环丙基、环丁基、环戊基、环己基等碳原子数3~18的环烷基;羟基;甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、仲丁氧基、叔丁氧基、己氧基、癸氧基、十二烷氧基等碳原子数1~18的直链或支链的烷氧基;乙酰基、丙酰基、丁酰基、2-甲基丙酰基、庚酰基、2-甲基丁酰基、3-甲基丁酰基、辛酰基、癸酰基、十二烷酰基、十八烷酰基等碳原子数2~18的直链或支链的烷基羰基;苯甲酰基、萘甲酰基等碳原子数7~11的芳基羰基;甲氧羰基、乙氧羰基、丙氧羰基、异丙氧羰基、丁氧羰基、异丁氧羰基、仲丁氧羰基、叔丁氧羰基、辛氧羰基、十四烷氧羰基、十八烷氧羰基等碳原子数2~19的直链或支链的烷氧羰基;苯氧羰基、萘氧羰基等碳原子数7~11的芳氧羰基;苯硫羰基、萘氧硫羰基等碳原子数7~11的芳硫羰基;乙酰氧基、乙基羰氧基、丙基羰氧基、异丙基羰氧基、丁基羰氧基、异丁基羰氧基、仲丁基羰氧基、叔丁基羰氧基、辛基羰氧基、十四烷基羰氧基、十八烷基羰氧基等碳原子数2~19的直链或支链的酰氧基;苯硫基、2-甲基苯硫基、3-甲基苯硫基、4-甲基苯硫基、2-氯苯硫基、3-氯苯硫基、4-氯苯硫基、2-溴苯硫基、3-溴苯硫基、4-溴苯硫基、2-氟苯硫基、3-氟苯硫基、4-氟苯硫基、2-羟基苯硫基、4-羟基苯硫基、2-甲氧基苯硫基、4-甲氧基苯硫基、1-萘硫基、2-萘硫基、4-[4-(苯硫基)苯甲酰基]苯硫基、4-[4-(苯硫基)苯氧基]苯硫基、4-[4-(苯硫基)苯基]苯硫基、4-(苯硫基)苯硫基、4-苯甲酰基苯硫基、4-苯甲酰基-2-氯苯硫基、4-苯甲酰基-3-氯苯硫基、4-苯甲酰基-3-甲硫基苯硫基、4-苯甲酰基-2-甲硫基苯硫基、4-(4-甲硫基苯甲酰基)苯硫基、4-(2-甲硫基苯甲酰基)苯硫基、4-(对甲基苯甲酰基)苯硫基、4-(对乙基苯甲酰基)苯硫基、4-(对异丙基苯甲酰基)苯硫基、4-(对叔丁基苯甲酰基)苯硫基等碳原子数6~20的芳硫基;甲硫基、乙硫基、丙硫基、异丙硫基、丁硫基、异丁硫基、仲丁硫基、叔丁硫基、戊硫基、异戊硫基、新戊硫基、叔戊硫基、辛硫基、癸硫基、十二烷硫基等碳原子数1~18的直链或支链的烷硫基;苯基、甲苯基、二甲基苯基、萘基等碳原子数6~10的芳基;噻吩基、呋喃基、吡喃基、吡咯基、噁唑基、噻唑基、吡啶基、嘧啶基、吡嗪基、吲哚基、苯并呋喃基、苯并噻吩基、喹啉基、异喹啉基、喹喔啉基、喹唑啉基、咔唑基、吖啶基、吩噻嗪基、吩嗪基、呫吨基、噻蒽基、吩噁嗪基、吩噁噻基、色满基、异色满基、二苯并噻吩基、呫吨酮基、噻吨酮基、二苯并呋喃基等碳原子数4~20的杂环基;苯氧基、萘氧基等碳原子数6~10的芳氧基;甲基亚磺酰基、乙基亚磺酰基、丙基亚磺酰基、异丙基亚磺酰基、丁基亚磺酰基、异丁基亚磺酰基、仲丁基亚磺酰基、叔丁基亚磺酰基、戊基亚磺酰基、异戊基亚磺酰基、新戊基亚磺酰基、叔戊基亚磺酰基、辛基亚磺酰基等碳原子数1~18的直链或支链的烷基亚磺酰基;苯基亚磺酰基、甲苯基亚磺酰基、萘基亚磺酰基等碳原子数6~10的芳基亚磺酰基;甲基磺酰基、乙基磺酰基、丙基磺酰基、异丙基磺酰基、丁基磺酰基、异丁基磺酰基、仲丁基磺酰基、叔丁基磺酰基、戊基磺酰基、异戊基磺酰基、新戊基磺酰基、叔戊基磺酰基、辛基磺酰基等碳原子数1~18的直链或支链的烷基磺酰基;苯基磺酰基、甲苯基磺酰基(甲苯磺酰基)、萘基磺酰基等碳原子数6~10的芳基磺酰基;下式(3)所示的亚烷基氧基(Q表示氢原子或甲基,k为1~5的整数);
(化学式3)
无取代的氨基以及用碳原子数1~5的烷基和/或碳原子数6~10的芳基单取代或者二取代的氨基(作为碳原子数1~5的烷基的具体例,可举出:甲基、乙基、丙基、丁基、戊基等直链烷基、异丙基、异丁基、仲丁基、叔丁基、异戊基、新戊基、叔戊基等支链烷基、环丙基、环丁基、环戊基等环烷基。作为碳原子数6~10的芳基的具体例,可举出:苯基、萘基等);氰基;硝基;氟、氯、溴、碘等卤素等。
另外,作为2个以上的R彼此直接或借助-O-、-S-、-SO-、-SO2-、-NH-、-NR’-(R’为碳原子数1~5的烷基或碳原子数6~10的芳基。作为碳原子数1~5的烷基的具体例,可举出:甲基、乙基、丙基、丁基、戊基等直链烷基、异丙基、异丁基、仲丁基、叔丁基、异戊基、新戊基、叔戊基等支链烷基、环丙基、环丁基、环戊基等环烷基等。作为碳原子数6~10的芳基的具体例,可举出:苯基、萘基等)、借助-CO-、-COO-、-CONH-、碳原子数1~3的亚烷基或者亚苯基键合而形成包含元素A的环结构的例子,可以举出下述环结构。
等
[A为VIA族~VIIA族(CAS表示法)的元素,L表示-O-、-S-、-SO-、-SO2-、-NH-、-NR’-、-CO-、-COO-、-CONH-。R’与前述相同。]
在式(1)中,键合于原子价m的VIA族~VIIA族(CAS表示法)的元素A的m+n(m-1)+1个的R彼此可以相同,也可以不同,R的至少1个、进一步优选所有R为可以具有前述取代基的碳原子数6~30的芳基或碳原子数4~30的杂环基。
式(1)中的D用下式(2)的结构表示。
(化学式2)
式(2)中的E表示亚甲基、亚乙基、亚丙基等碳原子数1~8的直链状、支链状或环状的亚烷基;亚苯基、亚二甲苯基、亚萘基、亚联苯基、亚蒽基等碳原子数6~20的亚芳基;二苯并呋喃二基、二苯并噻吩二基、呫吨二基、吩噁噻二基、噻蒽二基、双噻吩二基、双呋喃二基、噻吨酮二基、呫吨酮二基、咔唑二基、吖啶二基、吩噻嗪二基、吩嗪二基等碳原子数8~20的杂环化合物的2价基团。在此,杂环化合物的2价基团是指从杂环化合物的不同的2个环碳原子上各去掉1个氢原子而形成的2价基团。
上述亚烷基、亚芳基或杂环化合物的2价基团可以具有至少1种取代基,作为取代基的具体例,可举出:甲基、乙基、丙基、丁基、戊基、辛基等碳原子数1~8的直链烷基;异丙基、异丁基、仲丁基、叔丁基等碳原子数1~8的支链烷基;环丙基、环己基等碳原子数3~8的环烷基;甲氧基、乙氧基、丙氧基、丁氧基、己氧基等碳原子数1~8的烷氧基;苯基、萘基等碳原子数6~10的芳基;羟基;氰基;硝基或氟、氯、溴、碘等卤素。
式(2)中的G表示-O-、-S-、-SO-、-SO2-、-NH-、-NR’-(R’与上述相同)、-CO-、-COO-、-CONH-、碳原子数1~3的亚烷基或亚苯基。作为碳原子数1~3的亚烷基,可举出亚甲基、亚乙基、亚丙基等直链或支链状的亚烷基。
式(2)中的a为0~5的整数。a+1个E及a个G分别可以彼此相同,也可以不同。
在式(1)中,以下示出式(2)所示的D的代表例。
a=0的情况下
a=1的情况下
a=2的情况下
a=3的情况下
式(1)中的n表示[D-A+Rm-1]键合的重复单元数,优选为0~3的整数。
作为式(1)中的鎓离子[A+],优选的鎓离子为锍、碘鎓、硒鎓,作为代表例,可举出以下鎓离子。
作为锍离子,可举出:三苯基锍、三对甲苯基锍、三邻甲苯基锍、三(4-甲氧基苯基)锍、1-萘基二苯基锍、2-萘基二苯基锍、三(4-氟苯基)锍、三-1-萘基锍、三-2-萘基锍、三(4-羟基苯基)锍、4-(苯硫基)苯基二苯基锍、4-(对甲苯基硫基)苯基二对甲苯基锍、4-(4-甲氧基苯硫基)苯基双(4-甲氧基苯基)锍、4-(苯硫基)苯基双(4-氟苯基)锍、4-(苯硫基)苯基双(4-甲氧基苯基)锍、4-(苯硫基)苯基二对甲苯基锍、双[4-(二苯基锍基)苯基]硫醚、双〔4-{双[4-(2-羟基乙氧基)苯基]锍基}苯基〕硫醚、双{4-[双(4-氟苯基)锍基]苯基}硫醚、双{4-[双(4-甲基苯基)锍基]苯基}硫醚、双{4-[双(4-甲氧基苯基)锍基]苯基}硫醚、4-(4-苯甲酰基-2-氯苯硫基)苯基双(4-氟苯基)锍、4-(4-苯甲酰基-2-氯苯硫基)苯基二苯基锍、4-(4-苯甲酰基苯硫基)苯基双(4-氟苯基)锍、4-(4-苯甲酰基苯硫基)苯基二苯基锍、7-异丙基-9-氧代-10-硫杂-9,10-二氢蒽-2-基二对甲苯基锍、7-异丙基-9-氧代-10-硫杂-9,10-二氢蒽-2-基二苯基锍、2-[(二对甲苯基)锍基]噻吨酮、2-[(二苯基)锍基]噻吨酮、4-[4-(4-叔丁基苯甲酰基)苯硫基]苯基二对甲苯基锍、4-[4-(4-叔丁基苯甲酰基)苯硫基]苯基二苯基锍、4-[4-(苯甲酰基苯硫基)]苯基二对甲苯基锍、4-[4-(苯甲酰基苯硫基)]苯基二苯基锍、5-(4-甲氧基苯基)噻蒽鎓、5-苯基噻蒽鎓、5-甲苯基噻蒽鎓、5-(4-乙氧基苯基)噻蒽鎓、5-(2,4,6-三甲基苯基)噻蒽鎓等三芳基锍;二苯基苯甲酰甲基锍、二苯基4-硝基苯甲酰甲基锍、二苯基苄基锍、二苯基甲基锍等二芳基锍;苯基甲基苄基锍、4-羟基苯基甲基苄基锍、4-甲氧基苯基甲基苄基锍、4-乙酰羰氧基苯基甲基苄基锍、2-萘基甲基苄基锍、2-萘基甲基(1-乙氧羰基)乙基锍、苯基甲基苯甲酰甲基锍、4-羟基苯基甲基苯甲酰甲基锍、4-甲氧基苯基甲基苯甲酰甲基锍、4-乙酰羰氧基苯基甲基苯甲酰甲基锍、2-萘基甲基苯甲酰甲基锍、2-萘基十八烷基苯甲酰甲基锍、9-蒽基甲基苯甲酰甲基锍等单芳基锍;二甲基苯甲酰甲基锍、苯甲酰甲基四氢噻吩鎓、二甲基苄基锍、苄基四氢噻吩鎓、十八烷基甲基苯甲酰甲基锍等三烷基锍等。
作为碘鎓离子,可举出:二苯基碘鎓、二对甲苯基碘鎓、双(4-十二烷基苯基)碘鎓、双(4-甲氧基苯基)碘鎓、(4-辛氧基苯基)苯基碘鎓、双(4-癸氧基苯基)碘鎓、4-(2-羟基十四烷氧基)苯基苯基碘鎓、4-异丙基苯基(对甲苯基)碘鎓、4-异丁基苯基(对甲苯基)碘鎓等。
作为硒鎓离子,可举出:三苯基硒鎓、三对甲苯基硒鎓、三邻甲苯基硒鎓、三(4-甲氧基苯基)硒鎓、1-萘基二苯基硒鎓、三(4-氟苯基)硒鎓、三-1-萘基硒鎓、三-2-萘基硒鎓、三(4-羟基苯基)硒鎓、4-(苯硫基)苯基二苯基硒鎓、4-(对甲苯基硫基)苯基二对甲苯基硒鎓等三芳基硒鎓;二苯基苯甲酰甲基硒鎓、二苯基苄基硒鎓、二苯基甲基硒鎓等二芳基硒鎓;苯基甲基苄基硒鎓、4-羟基苯基甲基苄基硒鎓、苯基甲基苯甲酰甲基硒鎓、4-羟基苯基甲基苯甲酰甲基硒鎓、4-甲氧基苯基甲基苯甲酰甲基硒鎓等单芳基硒鎓;二甲基苯甲酰甲基硒鎓、苯甲酰甲基四氢硒吩鎓、二甲基苄基硒鎓、苄基四氢硒吩鎓、十八烷基甲基苯甲酰甲基硒鎓等三烷基硒鎓等。
在这些鎓中,优选的鎓为锍和碘鎓,特别优选的鎓可举出由下述锍离子和下述碘鎓离子组成的组中的1种以上,所述锍离子包括:三苯基锍、三对甲苯基锍、4-(苯硫基)苯基二苯基锍、双[4-(二苯基锍基)苯基]硫醚、双〔4-{双[4-(2-羟基乙氧基)苯基]锍基}苯基〕硫醚、双{4-[双(4-氟苯基)锍基]苯基}硫醚、4-(4-苯甲酰基-2-氯苯硫基)苯基双(4-氟苯基)锍、4-(4-苯甲酰基苯硫基)苯基二苯基锍、7-异丙基-9-氧代-10-硫杂-9,10-二氢蒽-2-基二对甲苯基锍、7-异丙基-9-氧代-10-硫杂-9,10-二氢蒽-2-基二苯基锍、2-[(二对甲苯基)锍基]噻吨酮、2-[(二苯基)锍基]噻吨酮、4-[4-(4-叔丁基苯甲酰基)苯硫基]苯基二对甲苯基锍、4-[4-(苯甲酰基苯硫基)]苯基二苯基锍、5-(4-甲氧基苯基)噻蒽鎓、5-苯基噻蒽鎓、二苯基苯甲酰甲基锍、4-羟基苯基甲基苄基锍、2-萘基甲基(1-乙氧羰基)乙基锍、4-羟基苯基甲基苯甲酰甲基锍和十八烷基甲基苯甲酰甲基锍等;所述碘鎓离子包括:二苯基碘鎓、二对甲苯基碘鎓、双(4-十二烷基苯基)碘鎓、双(4-甲氧基苯基)碘鎓、(4-辛氧基苯基)苯基碘鎓、双(4-癸氧基)苯基碘鎓、4-(2-羟基十四烷氧基)苯基苯基碘鎓、4-异丙基苯基(对甲苯基)碘鎓和4-异丁基苯基(对甲苯基)碘鎓等。
在式(1)中,X-为抗衡离子。其个数为每1分子为n+1。在抗衡离子中,没有特别限制,有硼化合物、磷化合物、锑化合物、砷化合物、烷基磺酸化合物等的卤化物、甲基化物等。例如,可举出:F-、Cl-、Br-、I-等卤离子;OH-;ClO4 -;FSO3 -、ClSO3 -、CH3SO3 -、C6H5SO3 -、CF3SO3 -等磺酸根离子类;HSO4 -、SO4 2-等硫酸根离子类;HCO3 -、CO3 2-等碳酸根离子类;H2PO4 -、HPO4 2-、PO4 3-等磷酸根离子类;PF6 -、PF5OH-、氟化烷基氟磷酸根离子等氟磷酸根离子类;BF4 -、B(C6F5)4 -、B(C6H4CF3)4 -等硼酸根离子类;AlCl4 -;BiF6 -等。此外,还可举出SbF6 -、SbF5OH-等氟锑酸根离子类、或者AsF6 -、AsF5OH-等氟砷酸根离子类等。
作为氟化烷基氟磷酸根离子,可举出下式(4)等所示的氟化烷基氟磷酸根离子。
式(4)
[(Rf)bPF6-b]-
在式(4)中,Rf表示用氟原子取代而成的烷基。Rf的个数b为1~5,优选为整数。b个Rf分别可以相同,也可以不同。Rf的个数b更优选为2~4、最优选为2~3。
在式(4)所示的氟化烷基氟磷酸根离子中,Rf表示用氟原子取代而成的烷基,优选的碳原子数为1~8、进一步优选的碳原子数为1~4。作为烷基,可举出:甲基、乙基、丙基、丁基、戊基、辛基等直链烷基;异丙基、异丁基、仲丁基、叔丁基等支链烷基;以及环丙基、环丁基、环戊基、环己基等环烷基等。作为具体例,可举出:CF3、CF3CF2、(CF3)2CF、CF3CF2CF2、CF3CF2CF2CF2、(CF3)2CFCF2、CF3CF2(CF3)CF、(CF3)3C等。
作为优选的氟化烷基氟磷酸根阴离子的具体例,可举出:[(CF3CF2)2PF4]-、[(CF3CF2)3PF3]-、[((CF3)2CF)2PF4]-、[((CF3)2CF)3PF3]-、[(CF3CF2CF2)2PF4]-、[(CF3CF2CF2)3PF3]-、[((CF3)2CFCF2)2PF4]-、[((CF3)2CFCF2)3PF3]-、[(CF3CF2CF2CF2)2PF4]-及[(CF3CF2CF2CF2)3PF3]-等。
对于阳离子聚合光引发剂,为了使其在环氧化合物、环氧树脂中容易溶解,可以使用预先溶解于溶剂类的阳离子聚合光引发剂。作为溶剂类,例如,可举出:甲醇、乙醇、正丙基醇、异丙基醇、正丁醇、异丁醇等醇类;丙酮、甲基乙基酮、甲基异丁基酮、甲基正丁基酮、甲基正丙基酮、环戊酮、环己酮等酮类;乙醚、乙基-叔丁基醚、四氢呋喃、1,3-二氧杂环己烷、1,4-二氧杂环己烷等醚类;碳酸亚丙酯、碳酸亚乙酯、碳酸1,2-亚丁酯、碳酸二甲酯、碳酸二乙酯等碳酸酯类;乙酸乙酯、乳酸乙酯、丁基溶纤剂乙酸酯、卡必醇乙酸酯、β-丙内酯、β-丁内酯、γ-丁内酯、δ-戊内酯、ε-己内酯等酯类;乙二醇单甲基醚、乙二醇单乙基醚、丙二醇单甲基醚、丙二醇单乙基醚、二乙二醇单甲基醚、二乙二醇单乙基醚、二丙二醇单甲基醚、二丙二醇单乙基醚、三乙二醇单甲基醚、三乙二醇单乙基醚、三丙二醇单甲基醚、三丙二醇单乙基醚等单烷基二醇醚类;乙二醇二甲基醚、乙二醇二乙醚、丙二醇二甲基醚、丙二醇二乙醚、二乙二醇二甲基醚、二乙二醇二乙醚、二丙二醇二甲基醚、二丙二醇二乙醚、三乙二醇二甲基醚、三乙二醇二乙醚、三丙二醇二甲基醚、三丙二醇二乙醚等二烷基二醇醚类;乙二醇单甲基醚乙酸酯、乙二醇单乙基醚乙酸酯、丙二醇单甲基醚乙酸酯、丙二醇单乙基醚乙酸酯等单烷基二醇醚的脂肪族羧酸酯类;甲苯、二甲苯、四甲基苯等芳香族烃类;己烷、辛烷、癸烷等脂肪族烃类;石油醚、石脑油、氢化石脑油、溶剂石脑油等石油系溶剂类;乙腈等腈类等。
这些阳离子聚合光引发剂可以选择1种或2种以上来使用。
作为(C)阳离子聚合光引发剂的阴离子物质,可举出硼化合物、磷化合物、锑化合物、砷化合物、烷基磺酸化合物等的卤化物等。这些阴离子物质可以选择1种或2种以上来使用。其中,在光固化性优异、粘接性、粘接耐久性提高方面,优选为氟化物。在氟化物中,优选为六氟锑酸盐。
对于(C)阳离子聚合光引发剂的用量,相对于(A)成分与(B)成分的合计100质量份,优选为0.01~5质量份,更优选为0.05~3质量份。如果阳离子聚合光引发剂的用量为0.01质量份以上,则不会使光固化性变差,如果为5质量份以下,则不会使粘接耐久性降低。
((D)光敏剂)
本实施方式的树脂组合物含有(D)光敏剂。光敏剂是指吸收能量射线、由阳离子聚合光引发剂高效地生成阳离子的化合物。
作为光敏剂,没有特别限制,可举出:二苯甲酮衍生物、吩噻嗪衍生物、苯基酮衍生物、萘衍生物、蒽衍生物、菲衍生物、并四苯衍生物、衍生物、苝衍生物、并五苯衍生物、吖啶衍生物、苯并噻唑衍生物、苯偶姻衍生物、芴衍生物、萘醌衍生物、蒽醌衍生物、呫吨衍生物、呫吨酮衍生物、噻吨衍生物、噻吨酮衍生物、香豆素衍生物、香豆素酮衍生物、花青衍生物、吖嗪衍生物、噻嗪衍生物、噁嗪衍生物、吲哚衍生物、薁衍生物、三烯丙基甲烷衍生物、酞菁衍生物、螺吡喃衍生物、螺噁嗪衍生物、硫代螺吡喃衍生物、有机钌络合物等。其中,优选为2-羟基-2-甲基-1-苯基-丙烷-1-酮等苯基酮衍生物和/或9,10-二丁氧基蒽等蒽衍生物,更优选为苯基酮衍生物,最优选为2-羟基-2-甲基-1-苯基-丙烷-1-酮。
对于(D)光敏剂的用量,在固化性不变差、贮藏稳定性不降低方面,相对于(A)成分与(B)成分的合计100质量份,优选为0.1~10质量份,更优选为0.5~5质量份,最优选为1~3质量份。
((E)稳定剂)
本实施方式的树脂组合物可以含有(E)稳定剂。通过含有稳定剂,本实施方式的树脂组合物显示出优异的贮藏稳定性。
作为稳定剂,没有特别限制,可举出抗氧化剂、醚化合物或它们的混合物。其中,优选为醚化合物,例如有:聚乙二醇、聚丙二醇、聚氧丁二醇等聚环氧烷、环状的冠醚等。其中,特别优选使用冠醚。
在上述稳定剂中,特别优选使用冠醚。通过使用冠醚,可以实现对于添加量而言适于制造有机EL显示装置的优异的固化性。
在使用聚环氧烷作为上述稳定剂的情况下,作为上述聚环氧烷的末端,没有特别限制,可以是羟基,也可以通过其它化合物进行醚化、酯化,还可以形成环氧基等官能团。其中,羟基、环氧基等因与上述光聚合性化合物反应而优选。
进而,作为上述聚环氧烷,还优选使用加成聚环氧烷的双酚衍生物,更优选使用特别是末端具有羟基或环氧基的化合物。
上述稳定剂优选分子内具有2个以上聚乙二醇和/或聚丙二醇。
在上述稳定剂中,作为分子内具有2个以上聚乙二醇的稳定剂的市售品,例如,可举出“RIKARESIN BEO-60E”、“RIKARESIN EO-20”(均为新日本理化公司制)等。
另外,作为分子内具有2个以上聚丙二醇的稳定剂的市售品,例如,可举出“RIKARESIN BPO-20E”、“RIKARESIN PO-20”(均为新日本理化公司制)等。
作为上述冠醚,没有特别限制,例如,可举出:12-冠醚-4、15-冠醚-5、18-冠醚-6、二环己烷并-18-冠醚-6等。
通过含有稳定剂,不仅能提高贮藏稳定性,而且能调节固化速度,可以形成从光照射开始经过一定时间后进行固化的光后固化性树脂组合物。
对于稳定剂的用量,相对于(A)成分与(B)成分的合计100质量份,优选为0.05~20质量份,更优选为0.1~10质量份。如果为0.05质量份以上,则贮藏稳定性提高,如果为20质量份以下,则也不会使固化性降低。
((F)硅烷偶联剂)
本实施方式的树脂组合物可以含有(F)硅烷偶联剂。通过含有硅烷偶联剂,本实施方式的树脂组合物显示出优异的粘接性及粘接耐久性。
作为硅烷偶联剂,没有特别限制,可举出:γ-氯丙基三甲氧基硅烷、乙烯基三甲氧基硅烷、乙烯基三氯硅烷、乙烯基三乙氧基硅烷、乙烯基-三(β-甲氧基乙氧基)硅烷、γ-甲基丙烯酰氧基丙基三甲氧基硅烷、γ-丙烯酰氧基丙基三甲氧基硅烷、β-(3,4-环氧环己基)乙基三甲氧基硅烷、γ-环氧丙氧基丙基三甲氧基硅烷、γ-环氧丙氧基丙基三乙氧基硅烷、γ-巯基丙基三甲氧基硅烷、γ-氨基丙基三乙氧基硅烷、N-β-(氨基乙基)-γ-氨基丙基三甲氧基硅烷、N-β-(氨基乙基)-γ-氨基丙基甲基二甲氧基硅烷和γ-脲基丙基三乙氧基硅烷等。这些硅烷偶联剂可以选择1种或2种以上来使用。其中,优选为由β-(3,4-环氧环己基)乙基三甲氧基硅烷、γ-环氧丙氧基丙基三甲氧基硅烷、γ-环氧丙氧基丙基三乙氧基硅烷、γ-甲基丙烯酰氧基丙基三甲氧基硅烷、γ-丙烯酰氧基丙基三甲氧基硅烷组成的组中的1种或2种以上。
对于硅烷偶联剂的用量,在可以得到粘接性、粘接耐久性方面,相对于(A)成分与(B)成分的合计100质量份,优选为0.1~10质量份,更优选为0.5~5质量份。
本实施方式的树脂组合物还可以含有脂肪族环氧化合物、氧杂环丁烷化合物、乙烯基醚化合物等其它阳离子聚合性化合物。
本实施方式的树脂组合物可以使用丙烯酸橡胶、氨基甲酸酯橡胶等各种弹性体、甲基丙烯酸甲酯-丁二烯-苯乙烯系接枝共聚物、丙烯腈-丁二烯-苯乙烯系接枝共聚物等接枝共聚物、无机填充剂、溶剂、增量材料、增强材料、增塑剂、增稠剂、染料、颜料、阻燃剂、表面活性剂等添加剂。
((G)微粒)
本实施方式的树脂组合物可以进一步含有微粒。对微粒没有特别限制,可以使用无机系或有机系的透明微粒等。
作为无机系的微粒,可举出:二氧化硅颗粒、玻璃填料、球状氧化铝、破碎氧化铝、氧化镁、氧化铍、氧化钛、氧化锆、氧化锌等氧化物类、氮化硼、氮化硅、氮化铝等氮化物类、碳化硅等碳化物类、氢氧化铝、氢氧化镁等氢氧化物类、铜、银、铁、铝、镍、钛等金属类、合金类、金刚石、碳等碳系填充材料、碳酸钙、硫酸钡、滑石、云母等。这些微粒可以用脂肪酸、有机硅偶联剂、钛酸酯系偶联剂等实施表面处理。另外,作为有机系的微粒,可举出:交联苯乙烯系颗粒、交联丙烯酸系颗粒、进行了氟改性的交联丙烯酸系颗粒、交联苯乙烯-丙烯酸系颗粒、交联有机硅系颗粒等。50%粒径优选为0.001μm以上且为30μm以下的范围。通过为上述范围,不会发生粒径过小而变得容易凝聚,也不会发生粒径过大而变得容易沉降。另外,微粒根据需要也可以使用它们的2种以上。
在此,所谓的50%粒径是指体积分布的累积频率为50%时的粒径。
作为粒径的测定方法,没有特别限制,例如,可举出激光衍射粒度分布仪、激光多普勒粒度分布仪、动态光散射粒度分布仪、超声波粒度分布仪等。
对于微粒的用量,相对于(A)成分与(B)成分的合计100质量份,优选为0.01~20质量份,更优选为0.1~10质量份。
(水分量)
对于本实施方式的树脂组合物的水分量,在抑制有机EL元件劣化方面,优选为1000ppm以下,更优选为500ppm以下,最优选为100ppm以下。在该水分量超过1000ppm的情况下,无法防止树脂组合物中所含的水分与有机EL元件接触,导致有机EL元件劣化。需要说明的是,该水分量可以是100ppm、200ppm、300ppm、400ppm、500ppm、600ppm、700ppm、800ppm、900ppm、1000ppm、1100ppm、1200ppm、1300ppm、1400ppm、1500ppm中的任一个值以下。
(氯量)
对于本实施方式的树脂组合物的氯量,在抑制有机EL元件劣化方面,优选为1000ppm以下,更优选为800ppm以下,更加优选为700ppm以下,最优选低于100ppm。在该氯量超过1000ppm的情况下,无法防止树脂组合物中所含的氯与有机EL元件接触,导致有机EL元件劣化。需要说明的是,该氯量可以是100ppm、200ppm、300ppm、400ppm、500ppm、600ppm、700ppm、800ppm、900ppm、1000ppm、1100ppm、1200ppm、1300ppm、1400ppm、1500ppm中的任一个值以下。
(粘度)
对于本实施方式的树脂组合物的粘度,为了得到优异的涂布性,如果剪切粘度为5mPa·s以上,则粘接剂不会润开至超过必要的程度,故优选。如果剪切粘度为2000mPa·s以下,则能用分配器等市售的涂布装置高精度地进行涂布,故优选。剪切粘度更优选为1000mPa·s以下。需要说明的是,该粘度可以是5mPa·s、10mPa·s、25mPa·s、50mPa·s、75mPa·s、100mPa·s、250mPa·s、500mPa·s、750mPa·s、1000mPa·s、2500mPa·s、5000mPa·s、7000mPa·s中任意2个值的范围内。
[实施方式2:固化物]
本实施方式的树脂组合物可以通过照射能量射线使其固化而形成固化物。此时,在本实施方式中,通过照射使用有下述光源的能量射线,可以进行树脂组合物的固化。
[光源]
作为用于本实施方式的树脂组合物的固化、粘接的光源,没有特别限制,可举出:卤素灯、金属卤化物灯、大功率金属卤化物灯(含有铟等)、低压汞灯、高压汞灯、超高压汞灯、氙气灯、氙气准分子灯、氙气闪光灯、发光二极管(以下称为LED)等。这些光源在可高效地进行与各个光聚合引发剂的反应波长相适应的能量射线的照射方面优选。
上述光源的各辐射波长、能量分布不同。因此,上述光源可根据光聚合引发剂的反应波长等来适当选择。另外,自然光(太阳光)也能成为反应引发光源。
作为上述光源的照射,可以进行直接照射、利用反射镜等的聚光照射、利用纤维等的聚光照射。也可以使用低波长截止滤光片、热射线截止滤光片、冷光镜等。
对于本实施方式的树脂组合物,为了促进光照射后的固化速度,可以进行后加热处理。对于后加热的温度,在用于有机EL元件的密封的情况下,在不会对有机EL元件带来损害方面,优选为120℃以下,更优选为80℃以下。
[实施方式3:粘接剂]
本实施方式的树脂组合物可以作为粘接剂使用。本实施方式的粘接剂可以优选用于有机EL元件等的封装等的粘接。
[实施方式4:树脂组合物的制造方法]
对于本实施方式的树脂组合物的制造方法,只要能将上述成分充分混合即可,没有特别限制。作为各成分的混合方法,没有特别限制,可举出:利用伴随螺旋桨的旋转的搅拌力的搅拌方法、利用基于自转公转的行星式搅拌机等普通的分散机的方法等。这些混合方法在能以低成本进行稳定的混合方面优选。
[降低水分量的方法]
本实施方式的树脂组合物的制造方法优选包括降低水分量的工序。作为降低水分量的方法,没有特别限制,可举出以下方法。
(1)通过干燥剂去除水分。在去除水分后,通过倾析或过滤将干燥剂分离。作为干燥剂,只要对树脂组合物没有影响即可,没有特别限制,可举出:高分子吸附剂(分子筛、合成沸石、氧化铝、硅胶等)、无机盐(氯化钙、无水硫酸镁、生石灰、无水硫酸钠、无水硫酸钙等)、固体碱类(氢氧化钠、氢氧化钾等)等。
(2)在减压条件下行进行加热,去除水分。
(3)在减压条件下进行蒸馏纯化。
(4)将干燥氮气、干燥氩气等非活性气体吹入各成分而去除水分。
(5)通过冷冻干燥去除水分。
对于降低水分量而言,可以对混合前的各成分分别降低水分,也可以在各成分混合后降低水分。降低水分量的工序可以使用1种或同时使用2种以上。在降低水分量的工序后,为了防止水分再次混入,优选在非活性气体气氛下进行处理。
[降低氯量的方法]
本实施方式的树脂组合物的制造方法优选包括降低氯量的工序。作为降低氯量的方法,没有特别限制,可举出以下方法。
环氧树脂通常通过使多元醇类和表氯醇反应来得到。在该制造方法中,产生由表氯醇引起的杂质氯。作为降低该杂质氯的方法,没有特别限制,可举出蒸馏等纯化方法等。此外,还可举出下述方法:在该反应时通过使用醇类(日本特开昭54-13596公报)、二氧杂环己烷等醚化合物(日本特开昭58-189223号公报)、二甲基亚砜(DMSO)等(日本特开昭63-254121号公报)高沸点非质子性极性溶剂,分别使多元醇化合物和表氯醇在高碱存在下反应的方法(例如,在碱金属氢氧化物存在下使其反应的方法)来降低杂质氯的产生。
[实施方式5:有机EL显示装置的制造方法]
作为使用本实施方式的固化性树脂组合物来制造有机EL显示装置的方法,例如,在一个基板(背面板)上涂布本实施方式的树脂组合物,对该树脂组合物照射光而使其活化,然后,隔断光,借助该组合物使背面板与形成有EL元件的基板粘贴,由此可以将有机EL元件在不暴露于光、热的情况下进行密封。
另外,也可以使用下述方法来制造有机EL显示装置:使用本树脂组合物,在一个基板上涂布本实施方式的树脂组合物,借助树脂组合物使其粘贴另一个基板,对本实施方式的树脂组合物照射光。
即,本实施方式的有机EL显示装置的制造方法是,将含有上述稳定剂的本实施方式的有机EL元件用密封剂涂布在防湿性基材的整个面或一部分后,照射光,在直至前述该树脂组合物发生固化的期间,将前述防湿性基材和有机EL元件粘贴来进行密封。
在本实施方式的有机EL显示装置的制造方法中,优选将防湿性基材与有机EL元件粘贴后进行加热。通过将上述防湿性基材与有机EL元件粘贴后进行加热,可以加速该树脂组合物的固化速度。
[实施例]
下面,举出实施例及比较例,进一步详细地说明本申请发明。本实施方式并不限定于这些例子。只要没有特别说明,则在23℃、相对湿度50质量%的条件下进行试验。
在实施例及比较例中,使用以下化合物。
作为(A)成分的环氧化合物,使用下述化合物。
(A-1)3,4-环氧环己烯基甲基-3’,4’-环氧环己烯甲酸酯(Daicel ChemicalIndustries,Ltd.制“Celloxide 2021P”)
(A-2)3,4-环氧环己基甲基甲基丙烯酸酯(Daicel公司制“CYM M100”)
作为(B)成分的环氧树脂,使用下述化合物。
(B-1)环氧化聚丁二烯树脂(日本曹达公司制“JP-200”、分子量2000~2600)
(B-2)2,2-双(羟甲基)-1-丁醇的1,2-环氧-4-(2-环氧乙烷基)环己烷加成物(Daicel Chemical Industries,Ltd.制“Celloxide EHPE3150”、分子量340~380)
(B-3)二环戊二烯型环氧化合物(ADEKA公司制“EP-4088S”分子量300~340)
(B-4)双酚A型环氧树脂(三井化学株式会社制“jER828”、分子量360~390)
(B-5)双酚F型环氧树脂(三井化学株式会社制“jER806”、分子量320~340)
(B-6)双酚F型环氧树脂(三井化学株式会社制“YL983U”、分子量360~380)
(B-7)氢化双酚A型环氧树脂(三井化学株式会社制“YX8000”、分子量380~430)
(B-8)双酚F型环氧树脂(ADEKA公司制“KRM-2490”、分子量340~380)
作为(C)成分的阳离子聚合光引发剂,使用下述化合物。
(C-1)三芳基锍六氟锑酸盐(ADEKA公司制“Adeka Optomer SP-170”、阴离子物质为六氟锑酸盐)
(C-2)三芳基锍盐(San-Apro公司制“CPI-200K”、阴离子物质为磷化合物)
作为(D)成分的光敏剂,使用下述化合物。
(D-1)2-羟基-2-甲基-1-苯基-丙烷-1-酮(BASF公司制“DAROCUR1173”)
(D-2)9,10-二丁氧基蒽(川崎化成工业公司制“ANTHRACURE UVS-1331”)
作为(E)成分的稳定剂,使用下述化合物。
(E-1)18-冠-6-醚(日本曹达公司制“Crown ether O-18”)
(E-2)15-冠-5-醚(日本曹达公司制“Crown ether O-15”)
(E-3)二环己烷并-18-冠-6-醚(东京化成工业公司制)
作为(F)成分的硅烷偶联剂,使用下述化合物。
(F-1)γ-环氧丙氧基丙基三甲氧基硅烷(Shin-Etsu Silicones Co.Ltd.,制“KBM-403”)
(F-2)γ-环氧丙氧基丙基三乙氧基硅烷(Shin-Etsu Silicones Co.Ltd.,制“KBE-403”)
(F-3)3-甲基丙烯酰氧基丙基三甲氧基硅烷(Momentive Performance MaterialsInc.制“A-174”)
作为(G)成分的微粒,使用下述化合物。
(G-1)二氧化硅(电气化学工业公司制“SFP-30M”)
(G-2)偶联剂表面处理二氧化硅(电气化学工业公司制“SFP-30MHE”)
(G-3)疏水性表面处理二氧化硅(Aerosil公司制“R-974”)
(G-4)氧化铝(电气化学工业公司制“ASFP-30”)
将表1~4所示的种类的原材料以表1~4所示的组成比例进行混合,制备实施例及比较例的树脂组合物。组成比例的单位为质量份。
在实施例及比较例中,根据需要进行下述去除水分的工序。
将各成分充分混合后,在非活性气体(氮气)气氛下,相对于树脂组合物100质量份,加入15质量份分子筛3A,在搅拌速度50~200rpm的条件下搅拌5~70小时。通过过滤搅拌后的树脂组合物,得到具有表1所示的水分量的树脂组合物。分子筛使用在200℃以上加热2小时以上、冷却后在装有硅胶的干燥器内保管的分子筛。在实施例及比较例中,根据需要进行蒸馏等之类的去除氯的工序。
对于实施例及比较例的树脂组合物,进行下述各测定。将其结果示于表1~4。
〔粘度〕
组合物的粘度(剪切粘度)用E型粘度计在温度25℃、转速10rpm的条件下进行测定。
〔水分量〕
树脂组合物的水分量用卡尔费休水分仪进行测定。
〔氯量〕
树脂组合物的氯量如下操作进行测定。在燃烧烧瓶中秤量试料约30mg和过氧化氢水(浓度0.5%)10mL,燃烧后,进行振荡,加入超纯水,制备成100mL。然后,使用离子色谱分析仪(DIONEX公司制)进行氯的定量分析,测定氯量。
〔光固化条件〕
在评价树脂组合物的固化物性及粘接性时,通过下述光照射条件,使树脂组合物固化。通过搭载无电极放电金属卤化物灯的UV固化装置(Fusion,Co.,Ltd.制),在波长365nm的累计光量4000mJ/cm2的条件下,使树脂组合物光固化后,在80℃的烘箱中实施30分钟的后加热处理,得到固化物。
〔透湿度〕
在前述光固化条件下制作厚度0.1mm的片状固化物,依照JIS Z0208“防湿包装材料的透湿度试验方法(杯法)”,使用氯化钙(无水)作为吸湿剂,在气氛温度60℃、相对湿度90%的条件下进行测定。透湿度优选为120g/(m2·24hr)以下。
〔拉伸剪切粘接强度〕
使用2片硼硅酸玻璃试验片(纵25mm×横25mm×厚2.0mm、TEMPAX(注册商标)玻璃),以粘接面积0.5cm2、粘接厚度80μm在上述光固化条件下使树脂组合物固化。固化后,使用通过由该树脂组合物形成的粘接剂接合的试验片,在温度23℃、相对湿度50%的环境下以拉伸速度10mm/分钟测定拉伸剪切粘接强度(单位:MPa)。
〔粘接耐久性(PCT)〕
使用2片硼硅酸玻璃试验片(纵25mm×横25mm×厚2.0mm、TEMPAX(注册商标)玻璃),以粘接面积0.5cm2、粘接厚度80μm在上述光固化条件下使树脂组合物固化。固化后,使用通过由该树脂组合物形成的粘接剂接合的试验片,在高压锅(以下称为PCT)121℃、相对湿度100质量%、2atm的气氛下暴露10小时,在温度23℃、相对湿度50%的环境下以拉伸速度10mm/分钟测定暴露后的试验片的拉伸剪切粘接强度(单位:MPa),通过下述(式1)求出粘接保持率。粘接保持率优选为25%以上、更优选为50%以上。
(式1)
粘接保持率(%)=(PCT后的拉伸剪切粘接强度)÷(初始的拉伸剪切粘接强度)×100
〔有机EL的评价〕
〔有机EL元件基板的制作〕
分别用丙酮、异丙醇清洗带ITO电极的玻璃基板。然后,通过真空蒸镀法依次蒸镀以下化合物以使其形成薄膜,得到有机EL元件基板。
·铜酞菁
·N,N’-二苯基-N,N’-二萘基联苯胺(α-NPD)
·三(8-羟基喹啉)铝
·氟化锂
·铝
〔有机EL元件的制作〕
在氮气气氛下用涂布装置将实施例及比较例中得到的树脂组合物涂布在玻璃上,与有机EL元件基板粘贴,以粘接厚度10μm在前述光固化条件下使由该树脂组合物形成的粘接剂固化,制作有机EL元件(有机EL评价)。
〔初始〕
对于刚制作后的有机EL元件,施加6V的电压,通过目视与显微镜观察有机EL元件的发光状态,测定暗斑的直径。
〔耐久性〕
对于刚制作后的有机EL元件,在85℃、相对湿度85质量%的条件下暴露1000小时后,施加6V的电压,通过目视与显微镜观察有机EL元件的发光状态,测定暗斑的直径。
暗斑的直径优选为300μm以下、更优选为50μm以下、最优选没有暗斑。
[保存稳定性试验]
在测定组合物的初始粘度(V0)后,在装入容器中并加盖的状态(密闭体系)下通过约40℃的高温环境下的促进试验测定4周后的组合物的粘度(V4)。然后,依据式:V4/V0求出粘度变化率。将粘度变化率为2以下的情况判断为保存稳定性良好。
[表1]
[表2]
[表3]
[表4]
由上述实验例判明以下内容。
本实施方式可以以微量的用量提供高精度的涂布性、粘接性、低透湿性、粘接耐久性优异的树脂组合物。本实施方式的树脂组合物具有低透湿性证实了是因为透湿度小的缘故。例如,在使用(D)成分的情况下,有机EL的耐久性提高(实施例1~9、实施例14~18与实施例10~13的比较)。
产业上的可利用性
本发明的树脂组合物具有较高的粘接性、较高的低透湿性,不会使有机EL元件劣化。在电子产品、尤其是有机EL等显示器部件、CCD、CMOS之类的图像传感器等电子部件、以及半导体部件等中使用的元件封装等的粘接中,可以优选应用本发明的树脂组合物。尤其是在有机EL用的密封用的粘接中最适宜,满足对有机EL元件等的元件封装用粘接剂所要求的特性。
Claims (18)
1.一种树脂组合物,其含有(A)数均分子量低于300的环氧化合物、(B)数均分子量为300至5000的环氧树脂、和(C)阳离子聚合光引发剂,并且水分量为1000ppm以下、氯量为1000ppm以下。
2.根据权利要求1所述的树脂组合物,其进一步含有(D)敏化剂。
3.根据权利要求1或2所述的树脂组合物,其进一步含有(E)稳定剂。
4.根据权利要求3所述的树脂组合物,其中,(E)稳定剂为醚化合物。
5.根据权利要求3所述的树脂组合物,其中,(E)稳定剂为环状醚化合物。
6.根据权利要求1或2所述的树脂组合物,其中,(A)环氧化合物为脂环式环氧化合物。
7.根据权利要求1或2所述的树脂组合物,其中,(B)环氧树脂不具有芳香族基团。
8.根据权利要求1或2所述的树脂组合物,其中,(B)环氧树脂为环氧化聚丁二烯。
9.根据权利要求1或2所述的树脂组合物,其含有(F)硅烷偶联剂。
10.一种粘接剂,其包含权利要求1~9中的任一项所述的树脂组合物。
11.一种制造权利要求1~9中的任一项所述的树脂组合物的方法,其包括如下工序:
(1)对混合前的各成分分别降低水分、并将各成分混合的工序;和/或
(2)在各成分混合后降低水分的工序。
12.根据权利要求11所述的制造方法,其中,(1)或(2)的降低水分量的工序包括选自由如下(a)~(e)的工序组成的组中的1种或2种以上的工序:
(a)工序,通过干燥剂去除水分,并在去除水分后通过倾析或过滤将干燥剂分离;
(b)工序,在减压条件下进行加热而去除水分;
(c)工序,在减压条件下进行蒸馏纯化;
(d)工序,将非活性气体吹入各成分中而去除水分;
(e)工序,通过冷冻干燥去除水分。
13.一种有机EL元件用密封剂,其包含权利要求1~9中的任一项所述的树脂组合物或权利要求10所述的粘接剂。
14.一种固化物,其是将权利要求1~9中的任一项所述的树脂组合物或权利要求10所述的粘接剂进行固化而成的。
15.一种有机EL装置,其使用权利要求1~9中的任一项所述的树脂组合物或权利要求10所述的粘接剂形成。
16.一种显示器,其使用权利要求1~9中的任一项所述的树脂组合物或权利要求10所述的粘接剂形成。
17.一种具有挠性的显示器或有机EL装置,其使用权利要求1~9中的任一项所述的树脂组合物或权利要求10所述的粘接剂形成。
18.一种有机EL装置的制造方法,其具有如下工序:
将权利要求13所述的有机EL元件用密封剂涂布在基材的整个面或一部分后照射光的工序;和
在直至所述有机EL元件用密封剂发生固化的期间,将所述基材和有机EL元件粘贴来密封所述有机EL元件的工序。
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JPWO2014017524A1 (ja) | 2016-07-11 |
KR102085332B1 (ko) | 2020-03-05 |
US10273389B2 (en) | 2019-04-30 |
JP2018090806A (ja) | 2018-06-14 |
TW201410720A (zh) | 2014-03-16 |
TWI637974B (zh) | 2018-10-11 |
JP6678219B2 (ja) | 2020-04-08 |
JP2019070120A (ja) | 2019-05-09 |
US20150210905A1 (en) | 2015-07-30 |
KR20150039757A (ko) | 2015-04-13 |
SG11201500481RA (en) | 2015-04-29 |
CN104487474A (zh) | 2015-04-01 |
SG10201706103VA (en) | 2017-09-28 |
KR20190073590A (ko) | 2019-06-26 |
KR102091871B1 (ko) | 2020-03-20 |
EP2878611A1 (en) | 2015-06-03 |
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JP6578339B2 (ja) | 2019-09-18 |
WO2014017524A1 (ja) | 2014-01-30 |
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