CN102464862A - 热固性组合物 - Google Patents
热固性组合物 Download PDFInfo
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- CN102464862A CN102464862A CN201010601898XA CN201010601898A CN102464862A CN 102464862 A CN102464862 A CN 102464862A CN 201010601898X A CN201010601898X A CN 201010601898XA CN 201010601898 A CN201010601898 A CN 201010601898A CN 102464862 A CN102464862 A CN 102464862A
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- epoxy resin
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- 239000000203 mixture Substances 0.000 title claims abstract description 77
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 56
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 52
- 239000003822 epoxy resin Substances 0.000 claims abstract description 51
- 229920005989 resin Polymers 0.000 claims abstract description 21
- 239000011347 resin Substances 0.000 claims abstract description 21
- 239000004593 Epoxy Substances 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 150000003142 primary aromatic amines Chemical class 0.000 claims abstract description 7
- 239000004014 plasticizer Substances 0.000 claims abstract description 6
- 150000003141 primary amines Chemical class 0.000 claims abstract description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 22
- 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 claims description 16
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000004902 Softening Agent Substances 0.000 claims description 12
- -1 aromatic primary amine Chemical class 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
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- 238000006384 oligomerization reaction Methods 0.000 claims description 11
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 claims description 9
- 229910015900 BF3 Inorganic materials 0.000 claims description 9
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- 239000007822 coupling agent Substances 0.000 claims description 7
- JDVIRCVIXCMTPU-UHFFFAOYSA-N ethanamine;trifluoroborane Chemical compound CCN.FB(F)F JDVIRCVIXCMTPU-UHFFFAOYSA-N 0.000 claims description 6
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 6
- 239000013034 phenoxy resin Substances 0.000 claims description 6
- 229920006287 phenoxy resin Polymers 0.000 claims description 6
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 claims description 5
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 4
- 235000012239 silicon dioxide Nutrition 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
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- GRFQCTQTJBMFGS-UHFFFAOYSA-N NC1=C(C=CC=C1)S(=O)(=O)N.NC1=CC=C(C=C1)S(=O)(=O)N Chemical compound NC1=C(C=CC=C1)S(=O)(=O)N.NC1=CC=C(C=C1)S(=O)(=O)N GRFQCTQTJBMFGS-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
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- 239000001301 oxygen Substances 0.000 claims description 3
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- OSJGPKXDWZYYFT-UHFFFAOYSA-N CCOC(CO[Si](CCCOCC1CO1)(OCC)OCC)(OCC)OC(C)CCCOCC2CO2 Chemical compound CCOC(CO[Si](CCCOCC1CO1)(OCC)OCC)(OCC)OC(C)CCCOCC2CO2 OSJGPKXDWZYYFT-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 229930003836 cresol Natural products 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- HUUCHDRSMXGHFR-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane diethoxy(methyl)silane Chemical compound CCO[SiH](C)OCC.CCO[Si](C)(CCCOCC1CO1)OCC HUUCHDRSMXGHFR-UHFFFAOYSA-N 0.000 claims description 2
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 claims description 2
- ILHOQKCVIFZHGS-UHFFFAOYSA-N n,n-dimethylaniline;trifluoroborane Chemical compound FB(F)F.CN(C)C1=CC=CC=C1 ILHOQKCVIFZHGS-UHFFFAOYSA-N 0.000 claims description 2
- YRZFHTRSHNGOSR-UHFFFAOYSA-N phenylmethanamine;trifluoroborane Chemical compound FB(F)F.NCC1=CC=CC=C1 YRZFHTRSHNGOSR-UHFFFAOYSA-N 0.000 claims description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 claims 1
- QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract description 5
- 125000000524 functional group Chemical group 0.000 abstract description 2
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- 238000012360 testing method Methods 0.000 description 15
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- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
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- 230000000694 effects Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000001291 vacuum drying Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000002742 anti-folding effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
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- 239000011159 matrix material Substances 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- 239000003351 stiffener Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 description 1
- NFVPEIKDMMISQO-UHFFFAOYSA-N 4-[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC=C(O)C=C1 NFVPEIKDMMISQO-UHFFFAOYSA-N 0.000 description 1
- LSAMTNWZBYOWMZ-UHFFFAOYSA-N 4-methylaniline;trifluoroborane Chemical compound FB(F)F.CC1=CC=C(N)C=C1 LSAMTNWZBYOWMZ-UHFFFAOYSA-N 0.000 description 1
- OTZFCCQPIUGYIF-UHFFFAOYSA-N C1=CC=CC=C1.NC1=CC=C(OC2=CC(=CC=C2)OC2=CC=C(C=C2)N)C=C1 Chemical compound C1=CC=CC=C1.NC1=CC=C(OC2=CC(=CC=C2)OC2=CC=C(C=C2)N)C=C1 OTZFCCQPIUGYIF-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- VQKFNUFAXTZWDK-UHFFFAOYSA-N alpha-methylfuran Natural products CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
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- 238000006731 degradation reaction Methods 0.000 description 1
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- 238000005516 engineering process Methods 0.000 description 1
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- 239000011521 glass Substances 0.000 description 1
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- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
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- 230000000630 rising effect Effects 0.000 description 1
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- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/182—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents
- C08G59/184—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents with amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/066—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with chain extension or advancing agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/226—Mixtures of di-epoxy compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/02—Applications for biomedical use
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/842—Containers
- H10K50/8426—Peripheral sealing arrangements, e.g. adhesives, sealants
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- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
本发明提供一种热固性组合物,包括以下成分:(a)寡聚合物,其中寡聚合物系由液态环氧树脂与具有4个反应氢原子之芳族伯胺反应(aromaticprimary amine)而得,该环氧树脂与该伯胺之当量摩尔比为1∶0.15~1∶2.50,且该寡聚物占该热固性组合物为约1~35重量百分比;(b)长分子链树脂,其中长分子链树脂占该热固性组合物为约5~10重量百分比;(c)具有两个或两个以上环氧官能团(epoxy functional groups)之环氧树脂,其中环氧树脂占该热固性组合物为约50~80重量百分比;以及(d)增塑剂(plasticizer),其中增塑剂占该热固性组合物为约5~15重量百分比。
Description
【技术领域】
本发明系有关于一种电子元件的封装材料,且特别是有关于一种有机电致发光元件(organic electroluminescent device)封装用的热固性组合物(thermosetting composition)。
【背景技术】
有机电致发光元件因为轻薄、低消耗功率(low power consumption)、高响应速率(rapid response speed)、宽视角(wide viewing angle)等优点,已成为平面显示器(flat display)的明日之星。
传统的有机电致发光元件使用紫外光型环氧树脂(UV light curingepoxy),此类的树脂较为硬脆,未来不适合于软性基材(flexible substrate)的封装。此外,使用紫外光型环氧树脂进行整面型涂布封装(entire surface-coatedsealing)时,紫外光的能量会造成元件中的有机材料劣化(degradation),或者是硬化过程由于快速反应的应力(stress)变化造成阴极与有机层剥离(peeling)问题,或者是树脂硬化不完全的问题。
为了解决上述问题,有不少专利提出热固性树脂(thermosetting resin)。JP 10-135255提出热固性树脂,其以酸酐系(anhydride)作为硬化剂,咪唑(imidazole)作为硬化促进剂(curing accelerating agent),然而,此方法需要较高的硬化温度。JP 2006-228708提出热固性树脂,其使用酸酐作为硬化剂,以2,4,6-三(二甲胺基甲基)苯酚(2,4,6-tris(dimethylaminomethyl)phenol)作为促进剂,然而,此成分需要在100℃1小时以上才能使树脂反应完全。
因此,业界极需发展一种有机电致发光元件封装用之热固性组合物,此组合物不但不会对元件造成不良的影响,且适用于软性基材。
【发明内容】
本发明提供一种热固性组合物,包括以下成分:(a)寡聚合物,其中该寡聚合物系由液态环氧树脂与具有4个反应氢原子之芳族伯胺反应(aromaticprimary amine)而得,该环氧树脂与该伯胺之当量摩尔比为1∶0.15~1∶2.50,且该寡聚物占该热固性组合物为约1~35重量百分比;(b)长分子链树脂,其中该长分子链树脂占该热固性组合物为约5~10重量百分比;(c)具有两个或两个以上环氧官能团(epoxy functional groups)之环氧树脂,其中该环氧树脂占该热固性组合物为约50~80重量百分比;以及(d)增塑剂(plasticizer),其中该增塑剂占该热固性组合物为约5~15重量百分比。
为让本发明之上述和其他目的、特征、和优点能更明显易懂,下文特举出较佳实施例,并配合所附图式,作详细说明如下:
【具体实施方式】
本发明提供一种热固性组合物,其成份中包括成分(a)寡聚物(低分子量的聚合物,其分子量通常小于10,000~20,000),此寡聚合物系由液态环氧树脂与具有4个反应氢原子的芳族伯胺反应(aromatic primary amine)而得,环氧树脂与伯胺的当量摩尔比为1∶0.15~1∶2.50,且寡聚物占热固性组合物为约1~35重量百分比。
此外,本发明热固性组合物亦包括其他成份,如成分(b)长分子链树脂(高分子量的聚合物,其分子量通常大于20,000~30,000),其中长分子链树脂占热固性组合物为约5~10重量百分比;成分(c)具有两个或两个以上环氧官能团的环氧树脂,且环氧树脂占热固性组合物为约50~80重量百分比;以及成分(d)增塑剂(plasticizer),其中增塑剂占热固性组合物为约5~15重量百分比。
上述成分(a)中液态环氧树脂包括双酚A系环氧树脂(bisphenol A epoxy)、或双酚F系(bisphenol F epoxy)环氧树脂、或脂肪族环氧树脂(aliphatic epoxy)、脂环族环氧树脂(cycloaliphatic epoxy)或上述之衍生物。而成分(a)中具有4个反应氢原子的芳族伯胺包括4,4′-二氨基二苯砜(4,4′-Diaminodiphenylsulfone)、氨基苯磺酰胺(4-Aminobenzenesulfonamide)、4,4′-二氨基二苯醚(4,4′-diaminodiphenyl ether)、1,3-双(4′-氨基苯氧基)苯(4,4′-(1,3-Phenylenedioxy)dianiline)、4,4′-二氨基二苯甲烷(4,4′-Diaminodiphenyl methane)或上述之衍生物。
于一实施例中,使用双酚A环氧树脂与4,4′-二氨基二苯砜(4,4′-Diaminodiphenyl sulfone)于温度为约100℃~150℃的条件下进行反应,可制得寡聚物。于另一实施例中,使用双酚A环氧树脂与氨基苯磺酰胺(4-Aminobenzenesulfonamide)于温度为约100℃~150℃的条件下进行反应,可制得另一寡聚物。
上述成分(b)长分子链树脂的平均分子量为约大于5万,其包括苯氧基树脂(phenoxy resin)、双酚A系环氧树脂、或双酚F系环氧树脂、或双酚A/双酚F系环氧树脂或上述之衍生物。
上述成分(c)之环氧树脂包括甲酚-可溶酚醛(cresol novolac)环氧树脂、或可溶可熔酚醛(phenol novolac)环氧树脂、双酚A系环氧树脂、或双酚F系环氧树脂、脂肪族环氧树脂、脂环族环氧树脂或上述之衍生物。
上述成分(d)之增塑剂的室温黏度为约20,000~52,000cps,其包括聚氨酯丙烯酸酯寡聚物(urethane acrylate oligmer)、聚酯丙烯酸酯寡聚物(polyesteracrylate oligmer)、丙烯酸类寡聚物(acrylic oligmer)、邻苯二甲酸酯类(phthalateesters)或上述之衍生物。
此处须注意的是,成分(a)作为热固性组合物的刚性部分(rigidity),可作为热硬化剂,成分(b)与成分(c)作为热固性组合物的主要基质(matrix),再额外搭配添加成分(d)增塑剂,以增加热固性组合物的附着力(adhesion)。
此外,本发明热固性组合物亦可加入其他添加剂,例如其他热硬化剂、填充物或偶联剂。热硬化剂包括三氟化硼乙胺(boron trifluoridemonoethylamine)、三氟化硼甲苯胺(boron trifluoride p-toluidine)、三氟化硼二甲基苯胺(boron trifluoride dimethyl aniline)、三氟化硼苄胺(boron trifluoridebenzyl amine)、或三氟化硼二甲基胺(boron trifluoride N,N-dimethyl amine)。
填充物的作用在于增加热固性组合物的阻水气、氧气之效果,其包括二氧化硅(silicon dioxide)、滑石粉(talcum powder)、氧化铝(aluminum oxide)、黏土(clay)。
偶联剂(coupling agent)的作用同样是增加热固性组合物之附着力,其中偶联剂包括3-环氧丙氧基丙基三甲氧基硅烷(3-glycidoxypropyltrimethoxysilane)、2-(3,4-环氧基环己基)乙基三甲氧基硅烷(2-(3,4epoxycyclohexyl)-ethyltrimethoxysilane)、3-环氧丙氧基丙基甲基二乙氧基硅烷(3-glycidoxypropylmethyl diethoxy silane)或3-环氧丙氧基丙基三乙氧基(3-glycidoxypropyltriethoxysilane)。
本发明热固性组合物之形成方法,系先将液态环氧树脂与具有4个反应氢原子之芳族伯胺进行反应,以合成寡聚物,再混合寡聚物、长分子链树脂、具有两个或两个以上环氧官能团之环氧树脂与增塑剂,于为约70-90℃的条件下反应约15~30分钟,即可完成硬化反应,相较于先前技术(需大于100℃且需1小时以上),本发明之反应温度较低,且反应时间较短。
本发明之热固性组合物经由抗折测试(flexibility test),实验结果显示此组合物可历经3000次弯折而不会有明显的裂痕,证明本发明之组合物具有良好的挠曲性(flexible ability)。另外,本发明之热固性组合物经由抗撕强度测试(peel strength),实验结果显示抗撕强度为约2.5~3.5公斤,代表本发明之热固性组合物与基材之间具有优异的附着力,此组合物不仅可以应用于软性基材之封装,更可以应用在金属薄片或玻璃基板的封装。再者,本发明之热固性组合物亦具有抑制暗点(dark spot)的产生且具有优异的阻气能力。
【实施例】
寡聚物的合成
100份重量的液态双酚A环氧树脂(EPON 828,Shell Chemicals公司)与35份重量的4,4′-二氨基二苯砜(4,4′-diaminodiphenyl sulfone;DDS,Alfa Aesar公司)混合后(当量摩尔比为1∶1.063),置于130℃油浴器内反应约1小时,合成EO-01寡聚合物。
100份重量的液态双酚A环氧树脂(EPON 828)与35份重量的对氨基苯磺酰胺(4-aminobenzenesulfonamide,TCI公司)混合后(当量摩尔比为1∶1.533),置于130℃油浴器内反应约1小时,合成EO-02寡聚合物。
100份重量的液态双酚A环氧树脂(EPON 828)与5份重量的4,4′-二氨基二苯砜(4,4′-diaminodiphenyl sulfone;DDS)混合后(当量摩尔比为1∶0.152),置于130℃油浴器内反应约1小时,合成EO-03寡聚合物。
100份重量的液态双酚A环氧树脂(EPON 828)与80份重量的4,4′-二氨基二苯砜(4,4′-diaminodiphenyl sulfone;DDS)混合后(当量摩尔比为1∶2.429),置于130℃油浴器内反应约1小时,合成EO-04寡聚合物。
(2)热固性组合物的形成
将上述寡聚物(EO-01、EO-02、EO-03、或EO-04);
长分子链树脂(PKHH(苯氧基树脂,phenoxy resin,InChem公司)、EPIKOTE 1256(双酚A型环氧树脂,bisphenol A type epoxy resin,Mw>51,000,Japan Epoxy Resins公司)、EPIKOTE 4250(双酚A/F(50/50)型环氧树脂,bisphenol A/F(50/50)type epoxy resin,Mw>59,000,Japan Epoxy Resins公司));
具有两个或两个以上环氧官能团之环氧树脂(ECN 1299(甲基酚醛环氧树脂,cresol formaldehyde novolac epoxy resin,Ciba公司)、EPON 828(双酚A环氧树脂,bisphenol A epoxy resin,Shell Chemicals公司));
增塑剂(CN997(聚氨酯丙烯酸酯寡聚物(urethane acrylate oligmer,Sartomer公司),于25℃下的黏度为25,000cps)、CN2200(聚酯丙烯酸酯寡聚物(polyester acrylate oligmer,Sartomer公司),于25℃下的黏度为52,000cps)、DOUBLEMER 3710(丙烯酸寡聚物(acylic oligmer,Sartomer公司),于25℃下的黏度为52,000cps);
以及有机溶剂丙二醇甲醚醋酸酯(propylene glycol mono-methyl etheracetate,Aldrich公司)于100~130℃进行融熔混合,接着降至室温后额外再分别加入滑石粉与热硬化剂(BF3-MEA,boron trifluoride monoethylamine,三氟化硼乙胺,TCI公司),再经由三滚筒研磨,即可制得实施例1-实施例13。
(3)物理性质测量
(i)抗折测试(flexibility test):将组合物涂布于60μm金属箔上(4×4.5cm2),先于烘箱70℃烘烤1小时,然后置于真空烘箱45℃烘烤15小时,再弯折3000次,以显微镜观察直径5公分范围内的裂痕,其中表示无裂痕,而×表示有裂痕。
(ii)抗撕强度测试(peel strength test):将组合物涂布于金属箔上(4×4.5cm2),先于烘箱70℃烘烤1小时,再于真空烘箱45℃烘烤15小时,然后此封装盖先置放90℃环境5~15分钟预反应,接着在60~90℃下与聚酰亚胺(PI)塑胶基材进行贴合,之后置于90℃环境30分钟完成硬化反应,使用双柱式拉力机(QC Teck)测试上述完成之样品,当测试所得数值越高,表示附着力越好。
(iii)水气测试(WVTR test(water vapor transmission rate test)):将组合物涂布于PET离型膜上(15×15cm2),先于烘箱70℃烘烤1小时,再于真空烘箱45℃烘烤15小时,然后此封装盖先置放90℃环境30分钟完成硬化反应,于40℃下,90%湿度的条件下使用水气渗透仪测试上述完成之样品,当测试所得数值越低,表示抗水气效果越好。
(iv)暗点测试:将组合物涂布于金属箔上(4×4.5cm2),先于烘箱70℃烘烤1小时,再于真空烘箱45℃烘烤15小时,然后此封装盖先置放90℃环境5~15分钟预反应,接着将此封装盖与已蒸镀完成之有机电致发光元件(OLED)在60~90℃下进行压合,之后置于90℃环境30分钟完成硬化反应。
表1显示实施例1~实施例13之热固性组合物各成分之组成与其物性结果。
表1
注1:phr(parts per hundreds of resin):每100单位树脂中,某物质所添加的量。
接续表1
接续表1
由表1之数据可得知,热固性组合物用于有机电致发光元件封止时,除了拥有优异的抑制暗点(Dark Spots)与阻气能力之外,更有良好的挠曲性与基材附着力的表现。
表2显示比较例1~比较例4之热固性组合物各成分之组成与其物性结果。
表2
由表2的数据可得知,当组合物仅有寡聚合物(EO-01Oligmer)时,其对基材之附着力几乎为零;而当组合物无寡聚合物存在时,其对基材的附着力低于2公斤重;再者,当组合物无增塑剂(CN997、CN2200或DOUBLEMER3710)时,其对基材的附着力低于1公斤重。另外,比较例中之组成皆无法有效抑制暗点的产生。
虽然本发明已以数个较佳实施例揭露如上,然其并非用以限定本发明,任何本领域技术人员,在不脱离本发明之精神和范围内,当可作任意之更动与润饰,因此本发明之保护范围当视后附之申请专利范围所界定者为准。
Claims (12)
1.一种热固性组合物,包括以下成分:
(a)寡聚合物,其中该寡聚合物系由液态环氧树脂与具有4个反应氢原子的芳族伯胺反应(aromatic primary amine)而得,该环氧树脂与该伯胺之当量摩尔比为1∶0.15~1∶2.50,且该寡聚物占该热固性组合物为1~35重量百分比;
(b)长分子链树脂,其中该长分子链树脂占该热固性组合物为5~10重量百分比;
(c)具有两个或两个以上环氧官能团的环氧树脂,其中该环氧树脂占该热固性组合物为50~80重量百分比;以及
(d)增塑剂(plasticizer),其中该增塑剂占该热固性组合物为5~15重量百分比。
2.如权利要求1所述的热固性组合物,其中成分(a)中该液态环氧树脂包括双酚A系环氧树脂(bisphenol A epoxy)、或双酚F系(bisphenol F epoxy)环氧树脂、或脂肪族环氧树脂(aliphatic epoxy)、脂环族环氧树脂(cycloaliphaticepoxy)、或上述之衍生物。
3.如权利要求1所述的热固性组合物,其中成分(a)中该具有4个反应氢原子的芳族伯胺包括4,4′-二氨基二苯砜(4,4′-Diaminodiphenyl sulfone)、氨基苯磺酰胺(4-Aminobenzenesulfonamide)、4,4′-二氨基二苯醚(4,4′-diaminodiphenyl ether)、1,3-双(4′-氨基苯氧基)苯(4,4′-(1,3-Phenylenedioxy)dianiline)、4,4′-二氨基二苯甲烷(4,4′-Diaminodiphenyl methane)、或上述之衍生物。
4.如权利要求1所述的热固性组合物,其中成分(b)中该长分子链树脂包括苯氧基树脂(phenoxy resin)、双酚A系环氧树脂、或双酚F系环氧树脂、或双酚A/双酚F系环氧树脂或上述之衍生物。
5.如权利要求1所述的热固性组合物,其中成分(c)中该环氧树脂包括甲酚-可溶酚醛(cresol novolac)环氧树脂、或可溶可熔酚醛(phenol novolac)环氧树脂、双酚A系环氧树脂、或双酚F系环氧树脂、脂肪族环氧树脂、脂环族环氧树脂或上述之衍生物。
6.如权利要求1所述的热固性组合物,其中该成分(d)中增塑剂包括聚氨酯丙烯酸酯寡聚物(urethane acrylate oligmer)、聚酯丙烯酸酯寡聚物(polyester acrylate oligmer)、丙烯酸类寡聚物(acrylic oligmer)、邻苯二甲酸酯类(phthalate esters)、或上述之衍生物。
7.如权利要求1所述的热固性组合物,还包括热硬化剂。
8.如权利要求7所述的热固性组合物,其中该热硬化剂包括三氟化硼乙胺(boron trifluoride monoethylamine)、三氟化硼甲苯胺(boron trifluoridep-toluidine)、三氟化硼二甲基苯胺(boron trifluoride dimethyl aniline)、三氟化硼苄胺(boron trifluoride benzyl amine)、或三氟化硼二甲基胺(borontrifluoride N,N-dimethyl amine)。
9.如权利要求1所述的热固性组合物,还包括填充物(filler)。
10.如权利要求9所述的热固性组合物,其中该填充物包括二氧化硅(silicon dioxide)、滑石粉(talcum powder)、氧化铝(aluminum oxide)、或黏土(clay)。
11.如权利要求1所述的热固性组合物,还包括偶联剂(coupling agent)。
12.如权利要求11所述的热固性组合物,其中该偶联剂包括3-环氧丙氧基丙基三甲氧基硅烷(3-glycidoxypropyltrimethoxysilane)、2-(3,4-环氧基环己基)乙基三甲氧基硅烷(2-(3,4-epoxycyclohexyl)-ethyltrimethoxysilane)、3-环氧丙氧基丙基甲基二乙氧基硅烷(3-glycidoxypropylmethyl diethoxy silane)、或3-环氧丙氧基丙基三乙氧基(3-glycidoxypropyltriethoxysilane)。
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US20120123039A1 (en) | 2012-05-17 |
US8604102B2 (en) | 2013-12-10 |
TW201221533A (en) | 2012-06-01 |
CN102464862B (zh) | 2014-09-10 |
TWI491638B (zh) | 2015-07-11 |
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