CN115073656B - 用于抗黄变和抗热裂应用的光聚合物 - Google Patents
用于抗黄变和抗热裂应用的光聚合物 Download PDFInfo
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- CN115073656B CN115073656B CN202210170438.9A CN202210170438A CN115073656B CN 115073656 B CN115073656 B CN 115073656B CN 202210170438 A CN202210170438 A CN 202210170438A CN 115073656 B CN115073656 B CN 115073656B
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- 238000004383 yellowing Methods 0.000 title abstract description 11
- BKUKXOMYGPYFJJ-UHFFFAOYSA-N 2-ethylsulfanyl-1h-benzimidazole;hydrobromide Chemical compound Br.C1=CC=C2NC(SCC)=NC2=C1 BKUKXOMYGPYFJJ-UHFFFAOYSA-N 0.000 title description 2
- 229910000679 solder Inorganic materials 0.000 claims abstract description 49
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000000178 monomer Substances 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- -1 tetrahydrofurfuryl Chemical group 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 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 11
- 239000003822 epoxy resin Substances 0.000 claims description 11
- 229920000647 polyepoxide Polymers 0.000 claims description 11
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 10
- 125000003367 polycyclic group Chemical group 0.000 claims description 9
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
- 229910044991 metal oxide Inorganic materials 0.000 claims description 7
- 150000004706 metal oxides Chemical class 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000005855 radiation Effects 0.000 claims description 4
- 239000004971 Cross linker Substances 0.000 claims description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 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 claims description 3
- 230000009477 glass transition Effects 0.000 abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 3
- 206010034972 Photosensitivity reaction Diseases 0.000 abstract description 2
- 230000036211 photosensitivity Effects 0.000 abstract description 2
- 239000000976 ink Substances 0.000 description 31
- 125000001072 heteroaryl group Chemical group 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 11
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
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- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000004408 titanium dioxide Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 125000003636 chemical group Chemical group 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- 239000011929 di(propylene glycol) methyl ether Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- 150000002576 ketones Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000004227 thermal cracking Methods 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001299 aldehydes Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000005336 cracking Methods 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 239000004843 novolac epoxy resin Substances 0.000 description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical group [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 229920005604 random copolymer Polymers 0.000 description 3
- 238000005476 soldering Methods 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- VJSQISKLKLDUTF-UHFFFAOYSA-N [O-][N+](N=NP(O)(SNO)=O)=O Chemical group [O-][N+](N=NP(O)(SNO)=O)=O VJSQISKLKLDUTF-UHFFFAOYSA-N 0.000 description 2
- 229920005603 alternating copolymer Polymers 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- 125000006747 (C2-C10) heterocycloalkyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- 125000005955 1H-indazolyl group Chemical group 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- NEBBLNDVSSWJLL-UHFFFAOYSA-N 2,3-bis(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(OC(=O)C(C)=C)COC(=O)C(C)=C NEBBLNDVSSWJLL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- IGZBSJAMZHNHKE-UHFFFAOYSA-N 2-[[4-[bis[4-(oxiran-2-ylmethoxy)phenyl]methyl]phenoxy]methyl]oxirane Chemical compound C1OC1COC(C=C1)=CC=C1C(C=1C=CC(OCC2OC2)=CC=1)C(C=C1)=CC=C1OCC1CO1 IGZBSJAMZHNHKE-UHFFFAOYSA-N 0.000 description 1
- WBHAUHHMPXBZCQ-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class COC1=CC=CC(C)=C1O WBHAUHHMPXBZCQ-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 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 1
- VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 description 1
- DMQYPVOQAARSNF-UHFFFAOYSA-N 3-[2,3-bis(3-prop-2-enoyloxypropoxy)propoxy]propyl prop-2-enoate Chemical compound C=CC(=O)OCCCOCC(OCCCOC(=O)C=C)COCCCOC(=O)C=C DMQYPVOQAARSNF-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- ZMDDERVSCYEKPQ-UHFFFAOYSA-N Ethyl (mesitylcarbonyl)phenylphosphinate Chemical compound C=1C=CC=CC=1P(=O)(OCC)C(=O)C1=C(C)C=C(C)C=C1C ZMDDERVSCYEKPQ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- 239000004642 Polyimide Substances 0.000 description 1
- KEEQOKBVDORLIS-UHFFFAOYSA-N S1(C=CC=C1)=O.[N+]1(=CC=CC=C1)[O-] Chemical compound S1(C=CC=C1)=O.[N+]1(=CC=CC=C1)[O-] KEEQOKBVDORLIS-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- INXWLSDYDXPENO-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CO)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C INXWLSDYDXPENO-UHFFFAOYSA-N 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- XWHTVJSRZQUVOT-UHFFFAOYSA-N aminosulfanyl-N-nitroiminophosphonamidic acid Chemical group NSP(=O)(N=N[N+](=O)[O-])O XWHTVJSRZQUVOT-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 239000004842 bisphenol F epoxy resin Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
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- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229910052711 selenium Inorganic materials 0.000 description 1
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Abstract
公开了一种具有高抗黄变性、优异的光敏性、高韧性和高玻璃化转变温度的丙烯酸酯基光聚合物、其制备方法和应用以及包含所述光聚合物的焊料。
Description
技术领域
本公开涉及可用于具有改进的抗黄变和抗热裂特性的阻焊油墨的光聚合物。
背景技术
阻焊层是一层薄的漆状聚合物层,其通常用于印刷电路板(PCB)的铜迹线,用于抗氧化保护并且防止在紧密间隔的焊盘之间形成焊桥。阻焊层是由阻焊油墨进行光固化的,其中光聚合物对阻焊层的光固化、粘附和物理特性起着关键作用。
典型的阻焊油墨通常是绿色的。然而,一些阻焊油墨是白色的,通常用于LED光或灯应用。然而,在汽车LED制造中,白色阻焊层在焊接时可能容易开裂,并且在回流焊接下变黄。
为了克服黄化,一些制造商倾向于添加更多的二氧化钛来增白阻焊层,或者添加更多的蓝色染料来中和黄化,以随着时间的推移保持白色外观。然而,如果添加过多的二氧化钛,则油墨的粘度将增加,导致阻焊油墨加工困难。二氧化钛的增加也可降低阻焊层的韧性和粘附性,这可导致阻焊层开裂和剥落。如果在阻焊油墨中添加较多的蓝色染料,则阻焊层会在开始时呈现蓝白色,这在美学上可能会令人不快。
对于热裂,阻焊层的玻璃化转变温度和韧性非常重要。阻焊层中的高交联密度可以提高Tg,从而可以减少高温下的变形。然而,在快速冷却下时,阻焊层可变得更加易碎。因此,需要引入柔性官能团以增强韧性来对抗大范围且快速的温度变化。
因此,需要能解决或克服至少一些上述问题的改进的阻焊油墨。
发明内容
本公开提供了一种具有高抗黄变性、优异的光敏性、高韧性和高玻璃化转变温度的丙烯酸酯基光聚合物结构。这种化合物可在用于汽车LED应用的白色阻焊油墨中使用。
在第一方面,本文提供了一种光聚合物,其包含:式I的单体单元、式II的单体单元、式III的单体单元和式IV的单体单元:
其中每个R1在每次出现时独立地是氢或甲基;
R2是环烷基或杂环烷基;
R3是烷基;并且
R4是由式V表示的部分:
其中A是-(CR2)nO-或键;
m是选自1-10的整数;
n是选自1-10的整数;
R在每次出现时独立地是氢或烷基;或两个R与它们所连接的碳原子一起形成3-8元环烷基;并且R5是氢或甲基。
在某些实施方案中,R2是C3-C12环烷基或C6-C12多环基。
在某些实施方案中,R2是异冰片基、环己基、环戊基、3,3,5-三甲基环己基、四氢糠基或2-四氢吡喃基。
在某些实施方案中,R3是C1-C12烷基。
在某些实施方案中,R3是甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、己基、辛基、癸基或2-乙基己基-2-甲基。
在某些实施方案中,R4选自由以下基团构成的组:
或者R4是/>的混合物,其中R5是氢或甲基。
在某些实施方案中,R2是C3-C12环烷基或C6-C12多环基;R3是C1-C12烷基;并且R4选自由以下基团构成的组:
或者R4是/>的混合物,其中R5是氢或甲基。
在某些实施方案中,R1是甲基;R2是异冰片基或环己基;R3是甲基、异丁基或正己基;并且R4是:
或者/>的混合物。
在某些实施方案中,相对于所述式I的单体单元、所述式II的单体单元、所述式III的单体单元和所述式IV的单体单元的总摩尔数,所述式I的单体单元以1-15mol%或1-10mol%的量存在于所述光聚合物中。
在某些实施方案中,相对于所述式I的单体单元、所述式II的单体单元、所述式III的单体单元和所述式IV的单体单元的总摩尔数,所述式II的单体单元以20-55mol%或35-50mol%的量存在于所述光聚合物中。
在某些实施方案中,相对于所述式I的单体单元、所述式II的单体单元、所述式III的单体单元和所述式IV的单体单元的总摩尔数,所述式III的单体单元以10-30mol%或15-25mol%的量存在于所述光聚合物中。
在某些实施方案中,相对于所述式I的单体单元、所述式II的单体单元、所述式III的单体单元和所述式IV的单体单元的总摩尔数,所述式IV的单体单元以30-55mol%或35-48mol%的量存在于所述光聚合物中。
在某些实施方案中,相对于所述式I的单体单元、所述式II的单体单元、所述式III的单体单元和所述式IV的单体单元的总摩尔数,所述式I的单体单元、所述式II的单体单元、所述式III的单体单元和所述式IV的单体单元分别以1-10mol%、35-50mol%、15-25%mol%和35-48mol%的量存在于所述光聚合物中。
在某些实施方案中,相对于所述式I的单体单元、所述式II的单体单元、所述式III的单体单元和所述式IV的单体单元的总摩尔数,所述式I的单体单元、所述式II的单体单元、所述式III的单体单元和所述式IV的单体单元分别以1-10mol%、35-50mol%、15-25%mol%和35-48mol%的量存在于所述光聚合物中。
在某些实施方案中,所述光聚合物的平均分子量为5,000至80,000amu或10,000至40,000amu。
在某些实施方案中,所述光聚合物选自由以下聚合物构成的组:一种光聚合物,其中R1是甲基;R2是环己基;R3是异丁基;并且R4是的混合物;
一种光聚合物,其中R1是甲基;R2是异冰片基;R3是正己基;并且R4是的混合物;或者
一种光聚合物,其中R1是甲基;R2是环己基;R3是甲基;并且R4是其中相对于所述式I的单体单元、所述式II的单体单元、所述式III的单体单元和所述式IV的单体单元的总摩尔数,所述式I的单体单元、所述式II的单体单元、所述式III的单体单元和所述式IV的单体单元分别以1-10mol%、35-50mol%、15-25%mol%和35-48mol%的量存在于所述光聚合物中。
在某些实施方案中,所述光聚合物的平均分子量为18,000至23,000amu。
在第二方面,本文提供了一种阻焊油墨,所述阻焊油墨包含本文所述的光聚合物和环氧树脂。
在某些实施方案中,所述阻焊油墨还包含光引发剂、交联剂和金属氧化物。
在第三方面,本文提供了一种将本文所述的阻焊油墨涂敷到基板上的方法,所述方法包括:将所述阻焊油墨涂敷到所述基板的表面,并用紫外线辐射照射所述阻焊油墨。
具体实施方式
定义
在整个申请中,当组合物被描述为具有、包括或包含特定组分,或方法被描述为具有、包括或包含特定方法步骤的情况下,则可以设想到,本教导的组合物也可以基本上由或由所列举组分组成,并且本教导的方法也可以基本上由或由所列举的方法步骤组成。
在本申请中,当要素或组分被称为包括于所列举要素或组分的列表中和/或选自所列举要素或组分的列表时,应理解该要素或组分可以是所列举要素或组分中的任一个,或者该要素或组分可以选自所列举要素或组分中的两个或更多个。此外,应理解,本文所述的组合物或方法的要素和/或特征可以在不背离本教导的精神和范围的情况下以各种方式组合,无论在本文中是明确的还是暗示的。
应理解,只要本教导仍然可行,则步骤的顺序或执行某些动作的顺序是不重要的。此外,可以同时进行两个或更多个步骤或动作。
除非另有明确说明,否则本文使用的单数包括复数(反之亦然)。此外,除非另有明确说明,当在定量值之前使用术语“约”时,本教导还包括具体的定量值本身。如本文所用的术语“约”是指相对标称值有±10%、±7%、±5%、±3%、±1%或±0%的变化,除非另有说明或推断。
术语“组合物”旨在涵盖包含指定量的指定成分的产品,以及直接或间接由指定量的指定成分的组合产生的任何产品。
如本文所用,“烷基”是指直链或支链的饱和烃基。烷基基团的例子包括甲基、乙基、丙基(例如,正丙基和异丙基)、丁基(例如,正丁基、异丁基、仲丁基、叔丁基)、戊基(例如,1-甲基丁基、2-甲基丁基、异戊基、叔戊基、1,2-二甲基丙基、新戊基和1-乙基丙基)、己基等。在各种实施方案中,烷基可具有1至40个碳原子(即C1-C40烷基),例如1-30个碳原子(即C1-C30烷基)。在某些实施方案中,烷基可具有1至6个碳原子,并且可称为“低级烷基”。低级烷基的例子包括甲基、乙基、丙基(例如,正丙基和异丙基)和丁基(例如,正丁基、异丁基、仲丁基、叔丁基)。在某些实施方案中,烷基可以如本文所述被任选地取代。烷基通常不被另一个烷基、烯基或炔基取代。
如本文所用,“环烷基”本身或作为另一取代基的一部分意味着(除非另有说明)在环体系中具有在3-12个的碳原子的单环烃,并且包括氢、直链、支链和/或环状取代基。示例性环烷基包括环丙基、环丁基、环戊基、环己基、环庚基等。
术语“多环基”或“多环基团”是本领域公认的,并且是指两个或更多个环(例如,环烷基、环烯基、环炔基、芳基和/或杂环基),其中两个或更多个碳是两个邻接环共有的,例如,这些环是“稠环”。通过非相邻原子连接的环称为“桥”环。多环的每个环可以被如上所述的取代基取代,所述取代基例如卤素、烷基、芳烷基、烯基、炔基、环烷基、羟基、氨基、硝基、巯基、亚氨基、酰胺基、膦酸酯、次膦酸酯、羰基、羧基、甲硅烷基、醚、烷硫基、磺酰基、酮、醛、酯、杂环基、芳族或杂芳族部分、-CF3、-CN等。
如本文所用,“稠环”或“稠环部分”是指具有至少两个环的多环体系,其中至少一个环是芳族的并且这种芳族环(碳环或杂环的)与可以是芳族或非芳族且碳环或杂环的至少一个其他环具有共同的键。这些多环体系可以是高度p-共轭的并且如本文所述被任选取代。
如本文所用,“杂芳基”是指含有至少一个选自氧(O)、氮(N)、硫(S)、硅(Si)和硒(Se)的环杂原子的芳族单环体系,或其中存在于环体系中的至少一个环是芳族的并且包含至少一个环杂原子的多环体系。多环杂芳基包括具有两个或更多个杂芳基环稠合在一起的基团,以及具有至少一个单环杂芳基环与一个或多个芳族碳环、非芳族碳环和/或非芳族环杂烷基环稠合的基团。杂芳基整体上可以具有例如5-24个环原子并且含有1-5个环杂原子(即,5-20元杂芳基)。杂芳基可以在任何杂原子或碳原子处连接到定义的化学结构上,从而产生稳定的结构。通常,杂芳基环不含有O-O、S-S或S-O键。然而,杂芳基中的一个或多个N或S原子可以被氧化(例如,吡啶N-氧化物噻吩S-氧化物、噻吩S,S-二氧化物)。杂芳基的例子包括例如以下所示的5或6元单环和5-6元双环体系:其中T是O、S、NH、N-烷基、N-芳基、N-(芳基烷基)(例如,N-苄基)、SiH2、SiH(烷基)、Si(烷基)2、SiH(芳基烷基)、Si(芳基烷基)2或Si(烷基)(芳基烷基)。此类杂芳基环的例子包括:吡咯基、呋喃基、噻吩基、吡啶基、嘧啶基、哒嗪基、吡嗪基、三唑基、四唑基、吡唑基、咪唑基、异噻唑基、噻唑基、噻二唑基、异噁唑基、噁唑基、噁二唑基、吲哚基、异吲哚基、苯并呋喃基、苯并噻吩基、喹啉基、2-甲基喹啉基、异喹啉基、喹喔啉基、喹唑啉基、苯并三唑基、苯并咪唑基、苯并噻唑基、苯并异噻唑基、苯并异噁唑基、苯并噁二唑基、苯并噁唑基、噌啉基、1H-吲唑基、2H-吲唑基、吲嗪基、异苯并呋喃基、萘啶基、酞嗪基、蝶啶基、嘌呤基、噁唑并吡啶基、噻唑并吡啶基、咪唑并吡啶基、呋喃并吡啶基、噻吩并吡啶基、吡啶并嘧啶基、吡啶并吡嗪基、吡啶并哒嗪基、噻吩并噻唑基、噻吩并噁唑基、噻吩并咪唑基等。杂芳基的另外的例子包括4,5,6,7-四氢吲哚基、四氢喹啉基、苯并噻吩并吡啶基、苯并呋喃并吡啶基等。在一些实施方案中,杂芳基可以如本文所述被任选取代。杂环可以在一个或多个位置被如本文所述的取代基取代,所述取代基例如卤素、烷基、芳烷基、烯基、炔基、环烷基、羟基、氨基、硝基、巯基、亚氨基、酰胺基、膦酸酯、次膦酸酯、羰基、羧基、甲硅烷基、醚、烷硫基、磺酰基、酮、醛、酯、杂环基、芳族或杂芳族部分、-CF3、-CN等。
术语“任选地取代”是指化学基团,如烷基、环烷基、芳基、杂芳基等,其中一个或多个氢可以被如本文所述的取代基替代,所述取代基例如卤素、叠氮化物、烷基、芳烷基、烯基、炔基、环烷基、羟基、烷氧基、氨基、硝基、巯基、亚氨基、酰胺基、膦酸酯、次膦酸酯、羰基、羧基、甲硅烷基、醚、烷硫基、磺酰基、磺酰胺基、酮、醛、酯、杂环基、芳族或杂芳族部分、-CF3、-CN等。
如本文所用,“聚合化合物”(或“聚合物”)是指包括多个通过共价化学键连接的一个或多个重复单元的分子。聚合化合物可由通式I表示:
*-(-(Ma)x—(Mb)y—)z*
通式I
其中Ma和Mb各自为重复单元或单体单元。聚合化合物可以仅具有一种类型的重复单元,也可以具有两种或更多种类型的不同重复单元。当聚合化合物仅具有一种类型的重复单元时,它可以称为均聚物。当聚合化合物具有两种或更多种类型的不同重复单元时,可以使用术语“共聚物”或“共聚化合物”来代替。例如,共聚化合物可以包括重复单元,其中Ma和Mb表示两种不同的重复单元。除非另有说明,否则在共聚物中重复单元的组装可以是头对尾、头对头或尾对尾。此外,除非另有说明,否则共聚物可以是无规共聚物、交替共聚物或嵌段共聚物。例如,通式I可用于表示在共聚物中具有x摩尔分数的Ma和y摩尔分数的Mb的Ma和Mb的共聚物,其中共聚单体单元Ma和Mb的重复方式可以是交替的、无规的、区域无规的、区域规整的或嵌段的,其中最多存在z个共聚单体单元。除了其组成外,聚合化合物还可以通过其聚合度(n)和摩尔质量(例如,数均分子量(M)和/或重均分子量(Mw),取决于测量技术)进一步表征。
如本文中关于化学基团或部分所使用的表示“”旨在表示上述化学基团或部分与另一个化学基团或部分共价键合的共价键。
本公开提供了一种光聚合物,所述光聚合物包含:式I的单体单元、式II的单体单元、式III的单体单元和式IV的单体单元:
其中每个R1在每次出现时独立地是氢或甲基;
R2是环烷基或杂环烷基;
R3是烷基;并且
R4是由式V表示的部分:
其中A是-(CR2)nO-或键;
m是选自1-10的整数;
n是选自1-10的整数;
R在每次出现时独立地是氢或烷基;或两个R与它们所连接的碳原子一起形成3-8元环烷基;并且R5是氢或甲基。
所述光聚合物可以是无规共聚物、交替共聚物或嵌段共聚物。在某些实施方案中,所述光聚合物是无规共聚物。
在某些实施方案中,R2是C3-C12环烷基、C3-C10环烷基、C3-C8环烷基、C3-C7环烷基、C3-C6环烷基、C3-C5环烷基、C2-C12杂环烷基、C2-C10杂环烷基、C2-C8杂环烷基、C2-C6杂环烷基、C3-C6杂环烷基、C3-C5杂环烷基或C3-C4杂环烷基,其中所述杂环烷基包含至多三个选自O、S和N的杂原子。在某些实施方案中,R2是异冰片基、环己基、环戊基、3,3,5-三甲基环己基、四氢糠基或2-四氢吡喃基。在某些实施方案中,R2是异冰片基或环己基。
在某些实施方案中,R3是C1-C12烷基、C1-C10烷基、C1-C8烷基、C1-C6烷基、C4-C6烷基、C1-C4烷基或C1-C2烷基,其中所述烷基是直链或支链的。在某些实施方案中,R3是甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、己基、辛基、癸基或2-乙基己基。在某些实施方案中,R3是甲基、异丁基或正己基。
在某些实施方案中,m是选自1-8、1-7、1-6、1-5、1-4、1-3或1-2的整数。
在某些实施方案中,n是选自2-8、2-7、2-6、2-5、3-5、2-4或2-3的整数。
在某些实施方案中,R在每次出现时独立地是氢、C1-C6烷基、C1-C5烷基、C1-C4烷基、C1-C3烷基或C1-C2烷基;或者两个R与它们所连接的碳原子一起形成3-8、3-7、3-6、5-6、3-5或3-4元环烷基。
在某些实施方案中,R4是由式VI表示的部分:
其中m是选自1-10的整数;
R在每次出现时独立地是氢或烷基;或两个R与它们所连接的碳原子一起形成3-8元环烷基;并且R5是氢或甲基。
在某些实施方案中,R4是由式VII表示的部分:
其中R在每次出现时独立地是氢或烷基;并且R5是氢或甲基。
在某些实施方案中,R4是由式VIII表示的部分:
其中p是选自0-3的整数;
其中q是选自0-3的整数;
其中r是选自0-3的整数;
R在每次出现时独立地是氢或烷基;并且
R5是氢或甲基。
在某些实施方案中,p是1;q是2;并且r是1。
在某些实施方案中,R4选自:
或者R4是/>的混合物,其中R5是氢或甲基。
在某些实施方案中,相对于所述式I的单体单元、所述式II的单体单元、所述式III的单体单元和所述式IV的单体单元的总摩尔数,所述式I的单体单元以1-15mol%、1-14mol%、1-13mol%、1-12mol%、1-11mol%、1-10mol%或5-10mol%的量存在于所述光聚合物中。
在某些实施方案中,相对于所述式I的单体单元、所述式II的单体单元、所述式III的单体单元和所述式IV的单体单元的总摩尔数,所述式II的单体单元以20-55mol%、25-55mol%、30-55mol%、30-50mol%或35-50mol%的量存在于所述光聚合物中。
在某些实施方案中,相对于所述式I的单体单元、所述式II的单体单元、所述式III的单体单元和所述式IV的单体单元的总摩尔数,所述式III的单体单元以10-30mol%或15-25mol%的量存在于所述光聚合物中。
在某些实施方案中,相对于所述式I的单体单元、所述式II的单体单元、所述式III的单体单元和所述式IV的单体单元的总摩尔数,所述式IV的单体单元以30-55mol%、30-50mol%、30-45mol%、35-45mol%或35-48mol%的量存在于所述光聚合物中。
在某些实施方案中,所述光聚合物的平均分子量为5,000至80,000amu、5,000至70,000amu、5,000至60,000amu、5,000至50,000amu、10,000至40,000amu、10,000至30,000amu、15,000至30,000amu、15,000至30,000amu、15,000至25,000amu或18,000至23,000amu。
本公开还提供了一种阻焊油墨,所述阻焊油墨包含至少一种本文所述的光聚合物和环氧树脂。
环氧树脂可以是任何常规环氧树脂。示例性环氧树脂包括但不限于甲酚酚醛环氧树脂、苯酚酚醛环氧树脂、双酚A环氧树脂、双酚F环氧树脂、双酚A-酚醛环氧树脂、萘环氧树脂、联苯环氧树脂、联苯芳烷基环氧树脂、聚丙烯酸酯环氧树脂及其组合。
在某些实施方案中,所述阻焊油墨还包含至少一种选自由光引发剂、交联剂、金属氧化物和流平剂组成的组的添加剂。
光引发剂应适合于在将其施加到基板上之后引起阻焊油墨的聚合(即固化)。对于大多数丙烯酸酯基的涂料配方,可以使用光引发剂,如酮类光引发添加剂和/或氧化膦添加剂。当用于本文所述的阻焊油墨中时,光引发剂以足以提供快速紫外线固化的量存在。
合适的光引发剂包括但不限于1-羟基环己基苯基酮(例如,Irgacure 184,购自Ciba Specialty Chemical(霍索恩,纽约州)、双(2,6-二甲氧基苯甲酰基)-2,4,4-三甲基戊基氧化膦(例如,商业共混物Irgacure 1800、1850和1700,购自Ciba SpecialtyChemical)、2,2-二甲氧基-2-苯基苯乙酮(例如,Irgacure 651,购自Ciba SpecialtyChemical)、双(2,4,6-三甲基苯甲酰基)苯基-氧化膦(Irgacure 819)、(2,4,6-三甲基苯甲酰基)二苯基氧化膦(Lucerin TPO,购自BASF(慕尼黑,德国))、乙氧基(2,4,6-三甲基苯甲酰基)苯基氧化膦(来自BASF的Lucerin TPO-L)及其组合。在某些实施方案中,光引发剂是TPO。
交联剂可以是二醇的二丙烯酸酯,如乙二醇、聚乙二醇和丙二醇的二丙烯酸酯;多元醇的聚丙烯酸酯,如己二醇、三羟甲基丙烷、季戊四醇、二季戊四醇或异氰脲酸三羟乙酯的聚丙烯酸酯;聚缩水甘油醚,如三羟甲基丙烷三缩水甘油醚和异氰脲酸三缩水甘油酯、三(4-羟基苯基)甲烷三缩水甘油醚、甘油丙氧基三丙烯酸酯、甘油三甲基丙烯酸酯、二醇的其他三丙烯酸酯和1,1,1,三(4-羟基苯基)乙烷;或其组合。在某些实施方案中,交联剂是异氰脲酸三缩水甘油酯和二季戊四醇五/六丙烯酸酯。
金属氧化物可以是二氧化钛、氧化铜、氧化锆或其组合。在某些实施方案中,金属氧化物是二氧化钛。
流平剂可以是以商品名/>-354出售的聚丙烯酸酯基的试剂。
本文所述的光聚合物可以以10%-60%wt/wt、10%-50%wt/wt、10%-40%wt/wt、10%-30%wt/wt、20%-30%wt/wt或25%-30%wt/wt的量存在于阻焊油墨中。
环氧树脂可以以10%-50%wt/wt、10%-40%wt/wt、10%-30%wt/wt、20%-30%wt/wt或25%-30%wt/wt的量存在于阻焊层中。
金属氧化物可以以10%-50%wt/wt、10%-40%wt/wt、10%-30%wt/wt、20%-30%wt/wt或25%-30%wt/wt的量存在于阻焊层中。
交联剂可以以1%-20%wt/wt、1%-10%wt/wt或5%-10%wt/wt的量存在于阻焊层中。
光引发剂可以以1%-10%wt/wt、1%-5%wt/wt或3%-5%wt/wt的量存在于阻焊层中。
阻焊油墨还可包含溶剂,如醇或醚,如二(丙二醇)甲基醚。
本公开还提供了一种将本文所述的阻焊油墨施加到基板上的方法,所述方法包括:将所述阻焊油墨施加到所述基板的表面,并用紫外线辐射照射所述阻焊油墨。
所述基板可以是任何材料,包括但不限于玻璃,金属如金、银、钯、镍/金、镍、锡、锡/铅、铝、锡/铝和铜,有机树脂,纸/树脂复合材料或树脂/玻璃纤维复合材料,陶瓷,聚酯或聚酰亚胺。
在某些实施方案中,所述方法还包括在用紫外线辐射照射所述阻焊油墨的步骤之前固化所述阻焊油墨。
阻焊油墨可在50-100℃、50-90℃、50-80℃、60-80℃或70-80℃的温度下固化。
实施例
实施例1-化合物1的合成
在第一步骤中,将二(丙二醇)甲基醚添加到反应器中并且用氮气脱气。然后缓慢添加偶氮二异丁腈(21.4g,0.13mol)、甲基丙烯酸环己酯(98g,0.58mol)、甲基丙烯酸甲酯(216g,2.16mol)和甲基丙烯酸(295g,3.43mol)。反应在95℃下搅拌8小时,然后在120℃下再搅拌1小时。
在第二步骤中,在冷却至90℃后,添加三苯基膦(9.0g,0.034mol)、4-甲氧基苯酚(2.1g,0.017mol),随后缓慢添加甲基丙烯酸缩水甘油酯(301g,2.12mol)。反应在90℃下再搅拌27小时以产生所需产物。
对于化合物1,w、x、y和z表示每种单体单元的mol%。对于本实施例,mol%为w=9.4%,x=35.1%,y=21.2%和z=34.3%。
实施例2-化合物2的合成
使用与化合物1类似的方法合成化合物2。
对于化合物2,w、x、y和z表示每种单体单元的mol%。对于本实施例,mol%为w=9.4%,x=35.1%,y=21.2%和z=34.3%。
实施例3-化合物3的合成
使用与化合物1类似的方法合成化合物3。
对于化合物3,w、x、y和z表示每种单体单元的mol%。对于本实施例,mol%为w=9.4%,x=35.1%,y=21.2%和z=34.3%。
实施例4–阻焊油墨的制备
A部分:
B部分:
将A部分和B部分的材料在二(丙二醇)甲基醚中预混合。将A部分和B部分以3:1的重量比率混合形成阻焊层。
将厚度约为25μm的阻焊油墨丝网印刷在具有1oz铜的PCB FR4上。印刷后,将板在75℃预烘45分钟,然后在强度为600mJ/cm2的紫外光下曝光20秒,随后用1%碳酸钠溶液显影。然后在测试前将板在150℃下后固化一小时。
实施例5–阻焊油墨测试
将化合物1、2和3在二(丙二醇)甲基醚中以50%的固体含量使用,与环氧树脂、光引发剂、交联剂、金属氧化物混合,得到白色阻焊油墨。光聚合物和油墨的性能,如玻璃化转变温度、油墨显影、铅笔硬度、抗黄变、抗热裂和光泽度,如表1所示。
表1.
化合物1 | 化合物2 | 化合物3 | |
玻璃化转变温度 | 132℃ | 130℃ | 128℃ |
预烘温度 | 73℃x 45min | 73℃x 45min | 73℃x 45min |
显影 | 良好 | 良好 | 良好 |
铅笔硬度 | 6H | 6H | 6H |
抗黄变 | 通过 | 通过 | 通过 |
抗热裂 | 通过 | 通过 | 通过 |
光泽度(60°) | 65 | 66 | 69 |
通过使用1%碳酸钠溶液进行显影;抗黄变测试在270℃进行5分钟,并且重复3次;抗热裂在焊炉中于288℃下进行10秒,并且重复3次。
实施例6–阻焊油墨测试
评价了改变每种单体单元的mol%和平均分子量对化合物1的物理化学性能的影响。这些测试的结果呈现于表2中。
表2.
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Claims (14)
1.一种光聚合物,所述光聚合物包含:式I的单体单元、式II的单体单元、式III的单体单元和式IV的单体单元:
其中每个R1在每次出现时独立地是氢或甲基;
R2是环烷基或杂环烷基;
R3是烷基;并且
R4是由式V表示的部分:
其中:
m是选自1-10的整数;
r是选自0-3的整数;并且
R5是氢或甲基,
其中所述光聚合物的平均分子量为15,000至30,000amu,并且
其中相对于所述式I的单体单元、所述式II的单体单元、所述式III的单体单元和所述式IV的单体单元的总摩尔数,所述式I的单体单元、所述式II的单体单元、所述式III的单体单元和所述式IV的单体单元分别以5-13mol%、35-50mol%、15-25mol%和30-45mol%的量存在于所述光聚合物中。
2.根据权利要求1所述的光聚合物,其中R2是C3-C12环烷基或C6-C12多环基。
3.根据权利要求1所述的光聚合物,其中R2是异冰片基、环己基、环戊基、3,3,5-三甲基环己基、四氢糠基或2-四氢吡喃基。
4.根据权利要求1所述的光聚合物,其中R3是C1-C12烷基。
5.根据权利要求1所述的光聚合物,其中R3是甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、己基、辛基、癸基或2-乙基己基。
6.根据权利要求1所述的光聚合物,其中R4选自由以下基团构成的组:
7.根据权利要求1所述的光聚合物,其中R2是C3-C12环烷基或C6-C12多环基;R3是C1-C12烷基;并且R4选自由以下基团构成的组:
8.根据权利要求1所述的光聚合物,其中R1是甲基;R2是异冰片基或环己基;R3是甲基、异丁基或正己基;并且R4是:
9.根据权利要求1所述的光聚合物,其中所述光聚合物的平均分子量为18,000至23,000amu。
10.根据权利要求1所述的光聚合物,其中所述光聚合物选自由以下聚合物组成的组:
一种光聚合物,其中R1是甲基;R2是环己基;R3是异丁基;并且R4是
一种光聚合物其中R1是甲基;R2是异冰片基;R3是正己基;并且R4是或者
一种光聚合物,其中R1是甲基;R2是环己基;R3是甲基;并且R4是
11.根据权利要求10所述的光聚合物,其中所述光聚合物的平均分子量为18,000至23,000amu。
12.一种阻焊油墨,包含根据权利要求1所述的光聚合物和环氧树脂。
13.根据权利要求12所述的阻焊油墨,所述阻焊油墨还包含光引发剂、交联剂和金属氧化物。
14.一种将根据权利要求13所述的阻焊油墨施加到基板的方法,所述方法包括:将所述阻焊油墨施加到所述基板的表面,并用紫外辐射照射所述阻焊油墨。
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CN109415572A (zh) * | 2016-06-28 | 2019-03-01 | 大日本印刷株式会社 | 色材分散液、着色树脂组合物、滤色器、液晶显示设备和发光显示设备 |
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