CN116068852A - 一种正性光敏性树脂组合物及其制备方法与应用 - Google Patents
一种正性光敏性树脂组合物及其制备方法与应用 Download PDFInfo
- Publication number
- CN116068852A CN116068852A CN202310083992.8A CN202310083992A CN116068852A CN 116068852 A CN116068852 A CN 116068852A CN 202310083992 A CN202310083992 A CN 202310083992A CN 116068852 A CN116068852 A CN 116068852A
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- China
- Prior art keywords
- iodonium
- bis
- positive photosensitive
- photosensitive resin
- dml
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 229920005989 resin Polymers 0.000 claims abstract description 41
- 239000011347 resin Substances 0.000 claims abstract description 41
- 239000000758 substrate Substances 0.000 claims abstract description 36
- 238000011161 development Methods 0.000 claims abstract description 24
- 239000002318 adhesion promoter Substances 0.000 claims abstract description 14
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 11
- 239000003112 inhibitor Substances 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 239000004065 semiconductor Substances 0.000 claims abstract description 6
- 238000004806 packaging method and process Methods 0.000 claims abstract description 4
- -1 iodonium salt compounds Chemical class 0.000 claims description 56
- 239000007822 coupling agent Substances 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 20
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 14
- 125000003700 epoxy group Chemical group 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 11
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical group O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
- 229910052710 silicon Inorganic materials 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 9
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- 150000004984 aromatic diamines Chemical class 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
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- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 8
- 238000002161 passivation Methods 0.000 claims description 8
- 229920002577 polybenzoxazole Polymers 0.000 claims description 8
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- 238000003756 stirring Methods 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
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- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 6
- CQZCVYWWRJDZBO-UHFFFAOYSA-N diphenyliodanium;nitrate Chemical compound [O-][N+]([O-])=O.C=1C=CC=CC=1[I+]C1=CC=CC=C1 CQZCVYWWRJDZBO-UHFFFAOYSA-N 0.000 claims description 6
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 6
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 5
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 claims description 5
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 5
- 238000006068 polycondensation reaction Methods 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 claims description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 4
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004849 alkoxymethyl group Chemical group 0.000 claims 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 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 4
- 238000004100 electronic packaging Methods 0.000 claims description 4
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- 229940116333 ethyl lactate Drugs 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 238000009413 insulation Methods 0.000 claims description 4
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 claims description 4
- 229920000647 polyepoxide Polymers 0.000 claims description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 claims description 3
- KUMMBDBTERQYCG-UHFFFAOYSA-N 2,6-bis(hydroxymethyl)-4-methylphenol Chemical compound CC1=CC(CO)=C(O)C(CO)=C1 KUMMBDBTERQYCG-UHFFFAOYSA-N 0.000 claims description 3
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 claims description 3
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 claims description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 3
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 3
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- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 3
- 239000000872 buffer Substances 0.000 claims description 3
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 claims description 3
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 3
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
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- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 claims description 3
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- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 3
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- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 claims description 2
- AYHVNGRMSLNAJQ-UHFFFAOYSA-M (3,5-dichlorophenyl)-(2,4,6-trimethoxyphenyl)iodanium 4-methylbenzenesulfonate Chemical compound Cc1ccc(cc1)S([O-])(=O)=O.COc1cc(OC)c([I+]c2cc(Cl)cc(Cl)c2)c(OC)c1 AYHVNGRMSLNAJQ-UHFFFAOYSA-M 0.000 claims description 2
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- CADOMGBBYLEKSI-UHFFFAOYSA-M (5-fluoro-2-nitrophenyl)-(2,4,6-trimethoxyphenyl)iodanium 4-methylbenzenesulfonate Chemical compound Cc1ccc(cc1)S([O-])(=O)=O.COc1cc(OC)c([I+]c2cc(F)ccc2[N+]([O-])=O)c(OC)c1 CADOMGBBYLEKSI-UHFFFAOYSA-M 0.000 claims description 2
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- RWAOPZVGICHCOI-UHFFFAOYSA-N 2,4-diaminobenzene-1,3-diol Chemical compound NC1=CC=C(O)C(N)=C1O RWAOPZVGICHCOI-UHFFFAOYSA-N 0.000 claims description 2
- RLXBOUUYEFOFSW-UHFFFAOYSA-N 2,5-diaminobenzene-1,4-diol Chemical compound NC1=CC(O)=C(N)C=C1O RLXBOUUYEFOFSW-UHFFFAOYSA-N 0.000 claims description 2
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- KCFVSHSJPIVGCG-UHFFFAOYSA-N 2-amino-4-[(3-amino-4-hydroxyphenyl)methyl]phenol Chemical compound C1=C(O)C(N)=CC(CC=2C=C(N)C(O)=CC=2)=C1 KCFVSHSJPIVGCG-UHFFFAOYSA-N 0.000 claims description 2
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- CHTZIDLXGXGNMA-UHFFFAOYSA-N 4-(2-trimethylsilylethynyl)aniline Chemical compound C[Si](C)(C)C#CC1=CC=C(N)C=C1 CHTZIDLXGXGNMA-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims description 2
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- RMDKEBZUCHXUER-UHFFFAOYSA-N 4-methylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C=CC1(C)C2 RMDKEBZUCHXUER-UHFFFAOYSA-N 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
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- INRIHDXRFIPNTI-UHFFFAOYSA-N CC[Si](CC)(CCN)O[Si](C)(C)CCN Chemical compound CC[Si](CC)(CCN)O[Si](C)(C)CCN INRIHDXRFIPNTI-UHFFFAOYSA-N 0.000 claims description 2
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Abstract
本发明公开一种正性光敏性树脂组合物及其制备方法与应用。本发明提供的正性光敏性树脂组合物包括下述质量份的组分:正性光敏性树脂100份;光致产酸剂5~40份;热交联剂3~30份;助粘剂1~30份;显影抑制剂1~30份;有机溶剂100~1000份。本发明改善了树脂组合物的储存稳定性,增强了固化树脂薄膜老化前后与Cu与Al的粘结性能,可防止实际应用中出现因老化粘附性降低引起的薄膜剥离等缺陷,使产品可靠性提高,同时不影响在Cu基板上的光刻分辨率,适用于半导体制造与封装领域,尤其适用于涉及到Cu布线层的应用场景。
Description
技术领域
本发明涉及一种正性光敏性树脂组合物及其制备方法与应用,属于高分子材料技术领域。
背景技术
光敏性聚酰亚胺/聚苯并噁唑树脂溶液具有优良的光刻制图工艺性,固化树脂具有高耐热、高电绝缘、高强高韧等优点,广泛应用于半导体制造过程的芯片表面钝化及多层金属互连结构的层间绝缘、先进电子封装(BGA、CSP、SiP等)基板的多层布线及凸点/微焊球制作工艺、塑封电路的应力缓冲层膜、光电显示器件的多层布线工艺等。
负性光敏性聚酰亚胺显影工序中使用的是有机溶剂,不利于环境保护,因此提出了能够用碱水溶液显影的正性感光性树脂,一般采用含酚羟基的聚酰亚胺前体或聚苯并噁唑前体树脂。但是正性感光性树脂的粘附性能较差,常常通过加入偶联剂来改善。
目前专利文献报道较多的偶联剂,主要为含有芳基氨基、脲基、硫脲基、乙烯基苯基、二(2-羟乙基)、丙烯酰氧基等基团的硅烷化合物来提高与基板的粘附性(见CN102540725A,CN102109763B,CN102725694B,CN102713756B、CN 109716235A报道),上述偶联剂或者价格相对较高,或者与金属Cu/Al的粘附性差需要与特殊添加剂配合使用、工艺复杂,因此工业化与应用受到一定限制。
目前市场上常用的含环氧基偶联剂(如KH560,KBM-303),粘结性能好,价格低廉,但是其反应活性较高,致使树脂组合物的储存稳定性差,光敏性降低;此外,该类偶联剂与金属Cu或Al的粘结性能较差,一般通过加入含有N、S、O等杂原子的低分子量化合物(见CN103502889B报道)来改善,然而加入该化合物时,可能该化合物与金属Cu的相互作用力太强,导致在金属Cu基板上光刻时,残胶很难冲洗干净,难以得到高分辨率的图案,且此低分子量化合物在产品使用过程中会缓慢地逸出,影响产品的可靠性。
发明内容
本发明的目的是提供一种正性光敏性树脂组合物及其制备方法及应用。所述正性光敏性树脂组合物储存稳定性好,不仅在Si晶圆上图案分辨率高,特别在Cu基板上也具有高分辨率;经曝光、显影、热固化后形成的树脂薄膜对Cu、Al基板具有高粘附性;同时具有高韧性、高耐热性,低介电常数、低吸水率等优点,适用于半导体制造与封装等领域。
为了实现上述目的,本发明采用的技术方案如下:
本发明提供一种正性光敏性树脂组合物,包括如下组分:正性光敏性树脂100份;光致产酸剂5~40份;热交联剂1~30份;助粘剂1~30份;显影抑制剂1~30份;有机溶剂100~1000份。
优选地,所述正性光敏性树脂组合物,包括如下组分:正性光敏性树脂100份;光致产酸剂12~15份;热交联剂3~10份;助粘剂8~12份;显影抑制剂2~5份;有机溶剂150~200份。
所述正性光敏性树脂由芳香族二酸或其衍生物与含酚羟基芳香族二胺,或芳香族二酸或其衍生物、含酚羟基芳香族二胺与含硅二胺在分子量调节剂存在条件下经缩聚反应得到。
所述正性光敏性树脂的GPC重均分子量为5000~100000,优选为10000-50000,进一步优选为20000-22000;分子量分布为1.6-2.0。
所述芳香族二酸或其衍生物选自二苯醚二甲酰氯、间苯二甲酰氯、对苯二甲酰氯、联苯二甲酰氯、二苯砜二甲酰氯、二苯基甲烷二甲酰氯和二苯酮二甲酰氯中的至少一种;优选为二苯醚二甲酰氯。
所述芳香族二酸或其衍生物的投料方式为:冰浴条件下,将含有所述芳香族二酸或其衍生物的溶液滴加至含有所述含酚羟基芳香族二胺或含有所述含酚羟基芳香族二胺与所述硅二胺的溶液中。
所述含酚羟基芳香族二胺选自2,2-双(3-氨基-4-羟苯基)六氟丙烷、2,2-双(4-氨基-3-羟苯基)六氟丙烷、3,3'-二氨基-4,4'-二羟基二苯砜、2,2-双(3-氨基-4-羟苯基)丙烷、双(3-氨基-4-羟基苯基)甲烷、3,3'-二氨基-4,4'-二羟基二苯醚、4,4'-二氨基-3,3'-二羟基二苯醚、双(3-氨基-4-羟基)联苯、双(3-氨基-4-羟基苯基)芴、3,3'-二氨基-4,4'-二羟基二苯甲酮、4,4'-二氨基-3,3'-二羟基二苯甲酮、1,4-二氨基-2,5二羟基苯、1,3-二氨基-2,4二羟基苯和1,3-二氨基-4,6二羟基苯中的至少一种;优选为2,2-双(3-氨基-4-羟苯基)六氟丙烷。
所述含硅二胺选自1,3-二(3-氨基丙基)-1,1,3,3-四甲基二硅氧烷、1,3-二(4-氨基丁基)-1,1,3,3-四甲基二硅氧烷、1,3-二(2-氨基乙基)-1,1-二甲基-3,3-二乙基-二硅氧烷、1,5-二(2-氨基乙基)-1,1,3,3,5,5-六甲基三硅氧烷、1,5-二(3-氨基丙基)-1,1,3,3,5,5-六甲基三硅氧烷、1-氨基丙基-5-氨基乙基-1,1,3,3,5,5-六甲基三硅氧烷、1,7-二(2-氨基乙基)-1,1,3,3,5,5,7,7-八甲基四硅氧烷、1,3-二(3-氨基苯基)-1,1,3,3-四甲基二硅氧烷、1,3-二(4-氨基苯基)-1,1,3,3-四甲基二硅氧烷和1,3-二(3-氨基丙基)-1,3-二甲基-1,3-二苯基二硅氧烷中的至少一种;优选为1,3-二(3-氨基丙基)-1,1,3,3-四甲基二硅氧烷。
所述分子量调节剂选自马来酸酐、降冰片烯二酸酐、甲基降冰片烯二酸酐、4-乙炔基邻苯二甲酸酐、4-苯乙炔苯酐、4-乙烯基苯胺、降冰片烯胺、烯丙胺、4-乙炔基苯胺、3-乙炔基苯胺、3-苯基乙炔基苯胺、4-苯基乙炔基苯胺、4-(4-氨基苯乙炔基)苯乙炔、4-[(三甲基硅基)-乙炔基]苯胺、4-(4-氨基-苯基)-2-甲基-丁-3炔-2-醇、(E)-3-氨基肉桂酸和炔丙胺中的至少一种;优选降冰片烯二酸酐。
所述缩聚反应使用的有机溶剂包括N’N-二甲基甲酰胺、N’N-二甲基乙酰胺、N-甲基-ε-己内酰胺、N-甲基吡咯烷酮、γ-丁内酯、乳酸乙酯、1,3-二甲基-2-咪唑烷酮、二甲基亚砜、二甲基砜、四亚甲基砜、四甲基脲、苯酚、m-甲酚、乳酸甲酯、乳酸丙酯、乳酸丁酯、甲苯、二甲苯、均三甲苯、二丙酮醇、甲基异丁基酮、乙酸乙酯、乙酸丁酯、环丁砜、p-甲酚、3-氯苯酚、4-氯苯酚、四氢呋喃、3-乙氧基丙酸乙酯、甲基乙基酮、环戊酮、环己酮、甲基丙基酮、四氢呋喃、四氢吡喃、二氧六环、二氧杂环己烷、乙二醇单甲醚、乙二醇单甲醚乙酸酯、乙二醇单乙醚乙酸酯、丙二醇单甲醚、丙二醇单乙醚和丙二醇单甲醚乙酸酯中的至少一种;优选N-甲基吡咯烷酮。
所述缩聚反应的反应条件为:温度为室温,时间为3-10h。
反应结束后,将反应液在不良溶剂中沉淀析出、洗涤、干燥,即可得到正性光敏性树脂固体树脂。
所述光致产酸剂包括重氮萘醌类化合物、碘鎓盐类化合物和锍盐类化合物中至少一种。
所述重氮萘醌类化合物选自1,2-重氮萘醌-5-磺酰基化合物和/或1,2-重氮萘醌-4-磺酰基化合物。
所述重氮萘醌类化合物通过下述方法中的一种制得:1)重氮萘醌类磺酸与多羟基化合物通过酯化反应生成;2)重氮萘醌类磺酸与多胺基化合物通过磺酰化反应生成;3)重氮萘醌类磺酸与多羟基多胺基化合物通过酯化和/或磺酰化反应生成;其中,所述多羟基多胺基化合物中被所述重氮萘醌类磺酸取代的比例为50%~100%。
所述多羟基化合物选自Bis-Z、BisP-EZ、BisP-AP、TekP-4HBPA、TrisP-HAP、TrisP-PA、TrisP-SA、TrisOCR-PA、BisOCHP-Z、BisP-MZ、BisP-PZ、BisP-IPZ、BisOCP-IPZ、BisP-CP、BisRS-2P、BisRS-3P、BisP-OCHP、Methylenetris-FR-CR、BisRS-26X、DML-MBPC、DML-MBOC、DML-OCHP、DML-PCHP、DML-PC、DML-PTBP、DML-34X、DML-EP、DML-POP、Dimethylol-BisOC-P、DML-PFP、DML-PSBP、DML-MTrisPC、TriML-P、TriML-35XL、TML-BP、TML-HQ、TML-PP-BPF、TML-BPA、TMOM-BP、HML-TPPHBA、HML-TPHAP(以上为商品名,可从本州化学工业(株)获得)、BIR-OC、BIP-PC、BIR-PC、BIR-PTBP、BIR-PCHP、BIP-BIOC-F、4PC、BIR-BIPC-F、TEP-BIP-A、46DMOC、46DMOEP、TM-BIP-A(以上为商品名,旭有机材工业(株)产品)、2,6-二甲氧基甲基-4-叔丁基苯酚、2,6-二甲氧基甲基-对甲酚、2,6-二乙酰氧基甲基-对甲酚、萘酚、2,3,4-三羟基二苯甲酮、2,3,4,4'-四羟基二苯甲酮、没食子酸甲酯、双酚A、双酚E、亚甲基双酚、联苯三酚丙酮树脂、间甲酚醛树脂和酚醛树脂中的任一种。
所述碘鎓盐类化合物选自双(4-叔丁苯基)碘鎓六氟磷酸盐、二苯基碘鎓六氟砷酸盐、二苯基碘鎓六氟磷酸盐、4-异丙基-4'-甲基二苯基碘鎓四(五氟苯基)硼酸盐、二苯基碘嗡三氟甲烷磺酸盐、二苯基碘硝酸盐、[4-(三氟甲基)苯基](2,4,6-三甲基苯基)碘鎓三氟甲磺酸盐、[3-(三氟甲基)苯基](2,4,6-三甲基苯基)碘鎓三氟甲磺酸盐、[(4-三氟甲基)苯基](2,4,6-三甲氧基苯基)碘鎓对甲苯磺酸盐、苯基(2,4,6-三甲氧基苯基)碘鎓对甲苯磺酸盐、苯基[3-(三氟甲基)苯基]碘鎓三氟甲烷磺酸盐、(4-硝基苯基)(苯基)碘鎓三氟甲磺酸盐、(4-甲苯基)(2,4,6-三甲基苯基)碘鎓三氟甲磺酸盐、(3-甲苯基)(2,4,6-三甲基苯基)碘鎓三氟甲磺酸盐、(2-甲苯基)(2,4,6-三甲基苯基)碘鎓三氟甲磺酸盐、4-异丙基-4'-甲基二苯基碘鎓四(五氟苯基)硼酸盐、[4-[(2-羟基十四烷基)氧基]苯基]苯基碘六氟锑酸盐、(5-氟-2-硝基苯基)(2,4,6-三甲氧基苯基)碘鎓对甲苯磺酸盐、二苯基碘鎓六氟磷酸盐、二苯基碘鎓六氟砷酸盐、(3,5-二氯苯基)(2,4,6-三甲氧基苯基)碘鎓对甲苯磺酸盐、(3-溴苯基)(均三甲苯基)碘鎓三氟甲磺酸盐、[4-(溴甲基)苯基](2,4,6-三甲氧基苯基)碘鎓对甲苯磺酸盐、双(2,4,6-三甲基吡啶)碘鎓六氟磷酸盐和4,4'-二甲苯基碘六氟磷酸盐中的至少一种。
所述锍盐类化合物选自1,3-苯并二硫代吡咯四氟化硼盐、环丙基二苯基锍四氟硼酸盐、二甲基(甲硫代)锍四氟硼酸盐、二苯基(甲基)锍四氟硼酸盐、(二氟甲基)双(2,5-二甲基苯基)锍四氟硼酸盐、2-[4-(3-乙氧基-2-羟基丙氧基)苯氨基甲酰]乙基二甲基硫对甲苯磺酸盐、4-羟苯基二甲基锍甲磺酸盐、三苯基锍四氟硼酸盐、三(4-甲苯基)锍六氟磷酸盐、三(4-甲苯基)锍三氟甲烷磺酸盐和三乙基锍双(三氟甲基磺酰)亚胺中的至少一种。
所述光致产酸剂优选为式B1和式B2所示化合物中的至少一种:
式B1、式B2中,R为H或1,2-萘醌二叠氮磺酰基。
所述热交联剂选自在加热条件下或在路易斯酸作用下,可发生交联反应的含有环氧基团的化合物和/或含有羟甲基或烷氧基甲基的化合物。
所述含有环氧基团的化合物选自双酚A型环氧树脂、双酚F型环氧树脂、丙二醇二缩水甘油基醚、聚丙二醇二缩水甘油基醚、聚甲基(缩水甘油基氧基丙基)和含有环氧基的有机硅中的至少一种;优选为3,3'-[氧基双亚甲基]双[3-乙基]氧杂环丁烷、1,4-丁二醇二缩水甘油醚、2,2-双(4-环氧丙氧基苯基)丙烷、9,9-双(4-环氧丙基氧-3-甲苯基)芴、9,9-双(4-环氧丙基氧基苯基)芴、1,3-双[2-(7-氧杂双环[4.1.0]庚-3-基)乙基]-1,1,3,3-四甲基二硅氧烷、1,2-环己烷二羧酸二缩水甘油酯、1,2,7,8-二环氧辛烷、4-环己烯-1,2-二羧酸二缩水甘油酯、异氰脲酸三缩水甘油酯、4,4'-亚甲基双(N,N-二环丙氧基苯胺)、新戊二醇二缩水甘油醚、2,2'-(2,2,3,3,4,4,5,5-八氟己烷-1,6-二基)双(环氧乙烷)、季戊二醇二缩水甘油醚、乙烯基环己烯二缩水甘油醚、聚乙二醇二缩水甘油醚(聚合度为1-15)、聚丙二醇二缩水甘油醚(聚合度为1~15)、聚二甲基硅氧烷二缩水甘油醚(聚合度为1-15)、丁二醇二缩水甘油醚、二缩水甘油苯胺、三羟甲基丙烷三缩水甘油醚、甘油三缩水甘油醚、5,5-二甲基-1,3-二(环氧乙烷基甲基)咪唑烷-2,4-二酮、2,2',2”-[次甲基-三(亚苯氧基亚甲基)]三(环氧乙烷)、1,1,1-三(4-羟基苯基)乙基三缩水甘油醚、双(2,3-环氧基环戊基)醚、3,4-环氧基-6-甲基环己基甲酸-3',4'-环氧基-6'-甲基环己基甲酯、乙烯基环己烯而环氧化合物、3,4-环氧基环己基甲酸-3',4'-环氧基环己基甲酯、二异戊二烯二环氧化合物、四苯基缩水甘油醚乙烷、三苯基缩水甘油醚基甲烷、三缩水甘油基-p-氨基苯酚、三缩水甘油基三聚异氰酸酯、四缩水甘油基二氨基二苯基甲烷、四缩水甘油基二甲苯二胺和四缩水甘油基-1,3-双氨基甲基环己烷中的至少一种;有商品名的产品可以列举出HP-850、HP-4032、HP-7200、HP-820、HP-4700、EXA-4710、HP-4770、EXA-859CRP、EXA-1514、EXA-4880、EXA-4850-150、EXA-4850-1000、EXA-4816、EXA-4822、BEO-60E、BPO-20E、HBE-100、DME-100、NC-3000、NC-6000(日本化药株式会社)。
所述含有羟甲基或烷氧基甲基的化合物选自46DMOC、46DMOEP(以上为商品名,旭有机材工业社制)、DML-PC、DML-PEP、DML-OC、DML-OEP、DML-34X、DML-PTBP、DML-PCHP、DML-OCHP、DML-PFP、DML-PSBP、DML-POP、DML-MBOC、DMLMBPC、DML-MTrisPC、DML-BisOC-Z、DML-BisOCHP-Z、DML-BPC、DMLBisOC-P、DMOM-PC、DMOMPTBP、DMOM-MBPC、TriML-P、TriML-35XL、TML-HQ、TML-BP、TML-pp-BPF、TML-BPE、TML-BPA、TML-BPAF、TML-BPAP、TMOM-BP、TMOM-BPE、TMOM-BPA、TMOM-BPAF、TMOM-BPAP、HML-TPPHBA、HML-TPHAP、HMOM-TPPHBA、HMOM-TPHAP(以上为商品名,可从本州化学工业株式会社获得)、“NIKALAC”MX-290、“NIKALAC”MX-280、“NIKALAC”MX-270、“NIKALAC”MX-279、“NIKALAC”MW-100LM、“NIKALAC”MX-750LM(三和化学株式会社)中的至少一种。
所述热交联剂优选为下述式C1、式C2和式C3所示化合物中的至少一种:
所述助粘剂由含活泼环氧基团的偶联剂钝化制得。
所述含活泼环氧基团的偶联剂选自γ-缩水甘油醚氧基丙基三甲氧基硅烷、γ-缩水甘油醚氧基丙基三乙氧基硅烷、2-(3,4-环氧环己烷)乙基三甲氧基硅烷、2-(3,4-环氧环己烷)乙基三乙氧基硅烷、5,6-环氧己基三乙氧基硅烷、3-缩水甘油醚氧基丙基甲基二乙氧基硅烷、3-[(2,3)-环氧丙氧]丙基甲基二甲氧基硅烷、(3-环氧丙氧基丙基)二甲基乙氧基硅烷、环氧丁基三甲氧基硅烷和环氧丁基三乙氧基硅烷中的至少一种;优选γ-缩水甘油醚氧基丙基三甲氧基硅烷和/或2-(3,4-环氧环己烷)乙基三甲氧基硅烷。
所述钝化使用的钝化剂选自含有N或S杂原子的脂肪族氨基化合物。所述钝化剂可在较温和的条件下将所述偶联剂上的活泼环氧基团钝化,不仅降低了其活性,而且工艺简单,不引入杂质,易于工业化生产。
所述钝化剂选自N-氨基吗啉、N,N-二乙基乙二胺、N-氨乙基哌嗪、N-甲基乙二胺、巯基乙胺、2-氨基-4,5-二氢噻唑-4-酮、2-(乙硫基)乙胺、2-(硫代甲基)乙胺、3-甲基硫代丙胺、2-(硫代叔丁基)乙胺、4-(2-胺乙基)硫代吗啉、(2-吗啉-4-乙基)-肼和4-甲基-1-哌嗪乙胺中的至少一种;优选巯基乙胺和/或N,N-二乙基乙二胺。本发明最突出的特点就是通过钝化偶联剂,改善了树脂组合物的储存稳定性,增强了固化树脂薄膜老化前后与Si、Cu与Al的粘结性能,同时不影响Cu基板上的光刻分辨率。
所述钝化的条件为:温度为30~50℃,时间为5-6h。
所述显影抑制剂选自曝光后可以阻碍正性光敏性树脂在碱性水溶液中的溶解、有助于调节留膜率和显影时间的化合物。所述显影抑制剂选自二苯基碘鎓硝酸盐、双(对叔丁基苯基)碘鎓硝酸盐、二苯基碘鎓溴化物、二苯基碘鎓氯化物和二苯基碘鎓碘化物中的至少一种;优选二苯基碘鎓硝酸盐。
所述有机溶剂选自N-甲基吡咯烷酮、N,N’-二甲基乙酰胺、N,N’-二甲基甲酰胺、二甲基亚砜、γ-丁内酯、乙酸乙酯、乙酸丁酯、乙酸正丙酯、乳酸甲酯、乳酸乙酯、乳酸丙酯、乳酸丁酯、甲苯、二甲苯、均三甲苯、二丙酮醇、甲基异丁基酮、环戊酮、环己酮、甲基乙基酮、甲基丙基酮、四氢呋喃、四氢吡喃、二氧六环、二氧杂环己烷、乙二醇单甲醚、乙二醇单甲醚乙酸酯、乙二醇单乙醚乙酸酯、丙二醇单甲醚、丙二醇单乙醚和丙二醇单甲醚乙酸酯中的至少一种。
本发明还提供所述正性光敏性树脂组合物的制备方法,包括如下步骤:
搅拌条件下,所述正性光敏性树脂、所述光致产酸剂、所述热交联剂、所述助粘剂及所述显影抑制剂分批次加入所述有机溶剂中形成均相溶液,经过滤得到正性光敏性树脂溶液。
本发明还提供一种图案化聚苯并噁唑树脂薄膜的制备方法,包括如下步骤:
所述正性光敏性树脂组合物经涂膜、曝光、显影、固化后,形成图案化聚苯并噁唑树脂薄膜。
所述图案化聚苯并噁唑树脂薄膜按照如下步骤进行制备:
1)将所述正性光敏性树脂组合物涂覆在基质表面,得到液态胶膜;
2)将所述液态胶膜进行烘烤,得到固态胶膜;
3)将所述固态胶膜表面覆盖掩膜版后进行紫外线曝光;
4)将所述紫外线曝光后的所述固态胶膜进行显影,溶解除掉曝光区域;
5)将所述显影后的所述固态胶膜进行清洗,得到未固化的图案化树脂膜;
6)将所述图案化树脂膜进行固化,得到固化后图案化聚苯并噁唑树脂薄膜。
步骤1)中,所述基质表面选自Si晶圆或溅射有Cu或Al的Si晶圆。
步骤1)中,所述正性光敏性树脂组合物是通过旋转涂覆在所述基质表面的。
步骤2)中,所述烘烤的条件为:温度为80~130℃,时间为1~30min。
步骤3)中,所述紫外线为i线或i线与g线组合。
步骤4)中,所述显影使用的显影剂选自四甲基氢氧化铵、氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、氢氧化胆碱、二乙醇胺、二乙基氨基乙醇三乙胺、二乙胺、甲胺、二甲胺、乙酸二甲氨基乙酯、二甲基氨基乙醇、甲基丙烯酸二甲氨基乙酯、环己胺、乙二胺和1,6-己二胺中的至少一种。
步骤5)中,所述清洗使用的漂洗液选自水或含有醇类或酯类的水溶液;所述醇类选自甲醇、乙醇、异丙醇等;所述酯类选自乳酸乙酯、丙二醇单甲醚醋酸酯等。
步骤6)中,所述固化的条件为:温度为300℃~350℃,氧含量低于100ppm。
本发明提供的所述正性光敏性树脂组合物的主要性能如表1所示。
表1正性光敏性树脂组合物的主要性能
本发明还提供所述正性光敏性树脂组合物作为半导体制造过程的芯片表面钝化、多层金属互连结构的层间绝缘、先进电子封装(BGA、CSP、SiP等)基板的多层布线及凸点/微焊球制作工艺、塑封电路的应力缓冲层膜中膜材料的应用。优选所述正性光敏性树脂组合物作为先进电子封装基板的Cu布线层中膜材料的应用。
本发明取得的有益效果如下:
本发明提供的正性光敏性树脂组合物的储存稳定性好,在Cu基板上具有与Si晶圆上同样优异的光刻性能;经曝光、显影、热固化后形成的树脂薄膜对Si、Cu、Al基板具有高粘附性;同时具有高韧性、高耐热性、低介电常数、低吸水率等优点。此外,由于未添加含N、S、O等杂原子的低分子量化合物,产品可靠性高,且钝化工艺简单、不引入杂质,易于工业化生产,因此具有显著的有益效果。
附图说明
图1为采用实施例1提供的正性光敏性树脂组合物制备的Cu基板在光刻显影后的无残胶的显微镜照片,其中右图为左图中线条的局部放大图。
图2为采用对比例6提供的正性光敏性树脂组合物制备的的Cu基板在光刻显影后的有残胶的显微镜照片,其中右图为左图中线条的局部放大图。
具体实施方式
下面结合具体实施方式对本发明进行进一步的详细描述,给出的实施例仅为了阐明本发明,而不是为了限制本发明的范围。
下述实施例中所用的材料、试剂等,如无特殊说明,均可从商业途径得到。
下述实施例中各性能指标测试或评价方法:
(1)分子量测试
采用GPC法测试重均分子量,标样为PS。使用LiBr(0.03mol/l)、H3PO4(0.06mol/l)的NMP溶液作为淋洗剂,聚合物浓度为1mg/ml。
(2)光刻性能评价
将正性光敏性树脂组合物溶液旋涂在6吋Si晶圆表面;在80~130℃下前烘处理1~30min,得到固态胶膜;在其表面放置掩膜板,采用紫外线i线曝光;然后用2.38wt%四甲基氢氧化铵水溶液显影液进行显影,经去离子水漂洗后,得到未固化的图案化树脂膜。用光干涉式膜厚仪测定显影后未曝光部分的膜厚,与显影前的膜厚相比,即为留膜率。
a.分辨率与灵敏度
用光学显微镜观察显影后的L/S=10μm/10μm的图形,将图形边缘光滑且无浮渣的显影时间定为基准,将该基准下所能观察到的最小图形尺寸设为分辨率L/S(μm),该分辨率所需要的最低曝光能量即为灵敏度(mJ/mm2)。
b.Cu基板分辨率
按照上述光刻性能评价方法中的在Si晶圆上匀胶、光刻、显影程序,在溅射有100nm铜层厚度的6吋Si晶圆(以下简称Cu基板)上进行光刻,按照分辨率评价方法进行评价,即得到Cu上的分辨率。
(3)储存稳定性评价
将配制的胶液在23±2℃,50±5RH%环境下放置14天,使用Brookfield粘度计测试胶液放置前后粘度变化并进行光刻性能评价:
若粘度变化率且灵敏度变化率均≤5%,其储存稳定性评价为良好;
若粘度变化率或灵敏度变化率>5%,其储存稳定性评价为不良;
粘度变化率(%)={(初始粘度-放置后粘度)绝对值}×100/初始粘度;
灵敏度变化率(%)={(初始灵敏度-放置后灵敏度)绝对值}×100/初始灵敏度。
(4)耐老化性能评价
将正性光敏性树脂组合物溶液分别旋涂于6吋Si晶圆、溅射有100nm铜层与铝层厚度的6吋Si晶圆(以下简称Cu基板与Al基板)上,在氮气保护的鼓风烘箱中于150℃固化30min,接着升温至320℃固化1h,得到固化膜;然后将固化膜放置于老化箱中,经Uhast96(130℃/85RH%/96h)老化处理。参照国家标准《GB/T 9286-1998色漆和清漆漆膜的划格试验》方法,使用划格器将上述老化前后的固化膜划出10行×10列方格,然后采用专用3M胶带进行剥离试验,按照“X/100”格式记录,“X”表示总剥离数,同时观察方格线条是否完整、光滑;
若分别在Si、Cu、Al基板上剥离下的方格数均不大于5且方格线条完整光滑,其耐老化性能评价为良好;
若任一基板上剥离下的方格数在5以上,或者方格线条不光滑、有毛刺,其耐老化性能评价为不良。
合成例1、苯并噁唑前驱体树脂A1的制备
在一个装有机械搅拌器、温度计和氮气保护装置的1L三口圆底烧瓶中,依次加入36.63g 2,2-双(3-氨基-4-羟苯基)六氟丙烷与146.5g NMP,搅拌使其溶解形成均相透明二胺溶液;采用冰浴将其冷却至5℃以下,一边搅拌一边向上述二胺溶液中滴加26.56g 4,4’-二苯醚二甲酰氯与106.2g NMP的混合溶液,滴加时间0.5h;然后,在室温下反应3h;再加入3.28g降冰片烯二酸酐,继续搅拌1h;将反应液倒入5L去离子水中,析出固体、过滤、真空干燥,得到苯并噁唑前驱体树脂A1-含酚羟基聚酰胺树脂,GPC测试重均分子量Mw=21500,分子量分布1.63。
合成例2、苯并噁唑前驱体树脂A2的制备
在一个装有机械搅拌器、温度计和氮气保护装置的1L三口圆底烧瓶中,依次加入34.79g 2,2-双(3-氨基-4-羟苯基)六氟丙烷、1.24g 1,3-二(3-氨基丙基)-1,1,3,3-四甲基二硅氧烷与144g NMP,搅拌使其溶解形成均相透明二胺溶液;采用冰浴将其冷却至5℃以下,一边搅拌一边向上述二胺溶液中滴加26.56g 4,4’-二苯醚二甲酰氯与106.2g NMP的混合溶液,滴加时间0.5h;然后,在室温下反应10h;再加入3.28g降冰片烯二酸酐,继续搅拌1h;将反应液倒入5L去离子水中,析出固体、过滤、真空干燥,得到苯并噁唑前驱体树脂A2-含酚羟基聚酰胺树脂,GPC测试重均分子量Mw=20600,分子量分布1.75。
合成例3、助粘剂的制备
向氮气保护的250mL洁净三口瓶中依次加入溶剂丙二醇甲醚或γ-丁内酯以及偶联剂,搅拌使其混合均匀,分别加入等摩尔量的钝化剂,30~50℃下反应6h,得到固含量为30%的助粘剂溶液,配胶时直接使用。该工艺中涉及到的偶联剂与钝化剂见表2中D1~D5所示。
表2中所示D6~D8偶联剂或其它添加剂作为助粘剂直接使用。
表2偶联剂与钝化剂的种类
树脂组合物用其它组分选择如下:
光致产酸剂B1为TPPA250(商品名)。
光致产酸剂B2为2,3,4-三羟基二苯甲酮-1,2-重氮萘醌-5-磺酸酯。
热交联剂为下述式C1、式C2和式C3所示化合物中的一种:
显影抑制剂为二苯基碘鎓硝酸盐。
实施例与对比例
在配有黄光灯的千级洁净间内,相对于100重量份上述苯并噁唑前驱体树脂,按照下述表3的加入量依次将光致产酸剂、热交联剂、助粘剂、显影抑制剂添加到溶剂F中(溶剂F是由GBL和PGEMA按照重量比9/1混合而成),室温下搅拌6h,经0.2μm孔径过滤器压滤,得到正性光敏性树脂组合物溶液。
表3各实施例及对比例配方
备注:表3中,()内表示相对于100重量份苯并噁唑前驱体树脂的添加量(质量份)。
将上述实施例及对比例中的正性光敏性树脂组合物溶液旋涂在6吋Si晶圆及Cu基板上,120℃烘烤3min后,得到8-10μm的前烘膜;在其表面上放置掩膜版,采用紫外灯i线曝光,用2.38wt%TMAH水溶液显影,去离子水冲洗后,得到立体光刻图案。
将实施例1~10与对比例1~6按照储存稳定性评价方法进行评价,其结果列于表4。
表4储存稳定性评价结果
表4中实施例1~10所得正性光敏性树脂组合物室温放置14天后,粘度与灵敏度变化均较小,说明采用含有N和S基团的脂肪族氨基化合物对活泼偶联剂完成了钝化作用,降低了偶联剂活性,不仅改善了树脂组合物的储存稳定性,而且不影响其光刻性能,在Cu基板上具有与Si晶圆上同样优异的光刻性能。
对比例1~6所得树脂组合物室温放置14天后,粘度均有大幅度上升,树脂组合物在同样的光刻工艺条件下灵敏度变差或者分辨率下降,说明其助粘剂仍然很活泼。其中对比例1~2粘度上升,可能因为3-氨基苯乙炔和2-巯基苯并咪唑活性较低,未将偶联剂钝化;对比例6在Cu基板光刻显影后有残胶,可能因为苯并三氮唑与Cu相互作用力较强,导致其在光刻显影后很难冲洗干净。
将实施例1~10与对比例1~6所得树脂组合物按照耐老化性能评价方法进行评价,结果列于表5。
表5耐老化性能评价
由表5实施例1~10可见,本发明的正性光敏性树脂组合物在Uhast96(130℃/85RH%/96h)老化处理前后与Si、Cu、Al的粘结性能均较好,说明采用含N和S杂原子的脂肪族氨基化合物对偶联剂进行钝化,增强了与金属Cu、Al的粘结性能。
对比例1中的钝化剂3-氨基苯乙炔虽然没有起到对偶联剂的钝化作用,但可以增强与金属Cu与Al的粘结性能;对比例2虽然与金属Cu、Al的粘结性能优良,但是划格时线条边缘有毛刺、不光滑,可能因为2-巯基苯并咪唑与Cu络合形成一层保护膜,导致划格时该保护膜因力学性能差在线条边缘出现毛刺、不光滑现象;对比例3、对比例4及对比例5的树脂组合物在Uhast96(130℃/85RH%/96h)老化处理后与金属Cu、Al的粘结性能差,划格时线条边缘有毛刺、不光滑;对比例6加入的含N杂原子低分子量化合物苯并三氮唑虽然可以改善树脂组合物与金属Al与Cu的粘结性能,但老化后与Cu的粘结性能急剧降低,说明其耐老化性能差,产品可靠性差。
由以上分析可知,本发明采用含N和S杂原子的脂肪族氨基化合物对偶联剂进行钝化,不仅改善了树脂组合物的储存稳定性,增强了固化树脂薄膜老化前后与Cu与Al的粘结性能,可防止实际应用中出现因老化粘附性降低引起的薄膜剥离等缺陷,使产品可靠性提高,同时不影响在Cu基板上的光刻分辨率。
综上所述,本发明提供的正性光敏性树脂组合物储存稳定性好,在Cu基板上具有与Si晶圆上同样优异的光刻性能;经曝光、显影、热固化后形成的树脂薄膜对Si、Cu、Al基板具有高粘附性;同时具有高韧性、高耐热性,低介电常数、低吸水率等优点,具有显著的有益效果,可满足半导体制造与封装领域的使用需求。
虽然,上文中已经用一般性说明及具体实施方案对本发明作了详尽的描述,但在本发明基础上,可以对之作一些修改或改进,这对本领域技术人员而言是显而易见的。因此,在不偏离本发明精神的基础上所做的这些修改或改进,均属于本发明要求保护的范围。
Claims (10)
1.一种正性光敏性树脂组合物,包括如下组分:
正性光敏性树脂100份;光致产酸剂5~40份;热交联剂1~30份;助粘剂1~30份;显影抑制剂1~30份;有机溶剂100~1000份。
2.根据权利要求1所述的正性光敏性树脂组合物,其特征在于:所述正性光敏性树脂由芳香族二酸或其衍生物与含酚羟基芳香族二胺,或芳香族二酸或其衍生物、含酚羟基芳香族二胺与含硅二胺经缩聚反应得到;所述缩聚反应在分子量调节剂存在的条件下进行。
3.根据权利要求2所述的正性光敏性树脂组合物,其特征在于:所述芳香族二酸或其衍生物选自二苯醚二甲酰氯、间苯二甲酰氯、对苯二甲酰氯、联苯二甲酰氯、二苯砜二甲酰氯、二苯基甲烷二甲酰氯和二苯酮二甲酰氯中的至少一种;
所述含酚羟基芳香族二胺选自2,2-双(3-氨基-4-羟苯基)六氟丙烷、2,2-双(4-氨基-3-羟苯基)六氟丙烷、3,3'-二氨基-4,4'-二羟基二苯砜、2,2-双(3-氨基-4-羟苯基)丙烷、双(3-氨基-4-羟基苯基)甲烷、3,3'-二氨基-4,4'-二羟基二苯醚、4,4'-二氨基-3,3'-二羟基二苯醚、双(3-氨基-4-羟基)联苯、双(3-氨基-4-羟基苯基)芴、3,3'-二氨基-4,4'-二羟基二苯甲酮、4,4'-二氨基-3,3'-二羟基二苯甲酮、1,4-二氨基-2,5二羟基苯、1,3-二氨基-2,4二羟基苯和1,3-二氨基-4,6二羟基苯中的至少一种;
所述含硅二胺选自1,3-二(3-氨基丙基)-1,1,3,3-四甲基二硅氧烷、1,3-二(4-氨基丁基)-1,1,3,3-四甲基二硅氧烷、1,3-二(2-氨基乙基)-1,1-二甲基-3,3-二乙基-二硅氧烷、1,5-二(2-氨基乙基)-1,1,3,3,5,5-六甲基三硅氧烷、1,5-二(3-氨基丙基)-1,1,3,3,5,5-六甲基三硅氧烷、1-氨基丙基-5-氨基乙基-1,1,3,3,5,5-六甲基三硅氧烷、1,7-二(2-氨基乙基)-1,1,3,3,5,5,7,7-八甲基四硅氧烷、1,3-二(3-氨基苯基)-1,1,3,3-四甲基二硅氧烷、1,3-二(4-氨基苯基)-1,1,3,3-四甲基二硅氧烷和1,3-二(3-氨基丙基)-1,3-二甲基-1,3-二苯基二硅氧烷中的至少一种;
所述分子量调节剂选自马来酸酐、降冰片烯二酸酐、甲基降冰片烯二酸酐、4-乙炔基邻苯二甲酸酐、4-苯乙炔苯酐、4-乙烯基苯胺、降冰片烯胺、烯丙胺、4-乙炔基苯胺、3-乙炔基苯胺、3-苯基乙炔基苯胺、4-苯基乙炔基苯胺、4-(4-氨基苯乙炔基)苯乙炔、4-[(三甲基硅基)-乙炔基]苯胺、4-(4-氨基-苯基)-2-甲基-丁-3炔-2-醇、(E)-3-氨基肉桂酸和炔丙胺中的至少一种。
4.根据权利要求1所述的正性光敏性树脂组合物,其特征在于:所述光致产酸剂包括重氮萘醌类化合物、碘鎓盐类化合物和锍盐类化合物中的至少一种;
所述重氮萘醌类化合物选自1,2-重氮萘醌-5-磺酰基化合物和/或1,2-重氮萘醌-4-磺酰基化合物;
所述碘鎓盐类化合物选自双(4-叔丁苯基)碘鎓六氟磷酸盐、二苯基碘鎓六氟砷酸盐、二苯基碘鎓六氟磷酸盐、4-异丙基-4'-甲基二苯基碘鎓四(五氟苯基)硼酸盐、二苯基碘嗡三氟甲烷磺酸盐、二苯基碘硝酸盐、[4-(三氟甲基)苯基](2,4,6-三甲基苯基)碘鎓三氟甲磺酸盐、[3-(三氟甲基)苯基](2,4,6-三甲基苯基)碘鎓三氟甲磺酸盐、[(4-三氟甲基)苯基](2,4,6-三甲氧基苯基)碘鎓对甲苯磺酸盐、苯基(2,4,6-三甲氧基苯基)碘鎓对甲苯磺酸盐、苯基[3-(三氟甲基)苯基]碘鎓三氟甲烷磺酸盐、(4-硝基苯基)(苯基)碘鎓三氟甲磺酸盐、(4-甲苯基)(2,4,6-三甲基苯基)碘鎓三氟甲磺酸盐、(3-甲苯基)(2,4,6-三甲基苯基)碘鎓三氟甲磺酸盐、(2-甲苯基)(2,4,6-三甲基苯基)碘鎓三氟甲磺酸盐、4-异丙基-4'-甲基二苯基碘鎓四(五氟苯基)硼酸盐、[4-[(2-羟基十四烷基)氧基]苯基]苯基碘六氟锑酸盐、(5-氟-2-硝基苯基)(2,4,6-三甲氧基苯基)碘鎓对甲苯磺酸盐、二苯基碘鎓六氟磷酸盐、二苯基碘鎓六氟砷酸盐、(3,5-二氯苯基)(2,4,6-三甲氧基苯基)碘鎓对甲苯磺酸盐、(3-溴苯基)(均三甲苯基)碘鎓三氟甲磺酸盐、[4-(溴甲基)苯基](2,4,6-三甲氧基苯基)碘鎓对甲苯磺酸盐、双(2,4,6-三甲基吡啶)碘鎓六氟磷酸盐和4,4'-二甲苯基碘六氟磷酸盐中的至少一种;
所述锍盐类化合物选自1,3-苯并二硫代吡咯四氟化硼盐、环丙基二苯基锍四氟硼酸盐、二甲基(甲硫代)锍四氟硼酸盐、二苯基(甲基)锍四氟硼酸盐、(二氟甲基)双(2,5-二甲基苯基)锍四氟硼酸盐、2-[4-(3-乙氧基-2-羟基丙氧基)苯氨基甲酰]乙基二甲基硫对甲苯磺酸盐、4-羟苯基二甲基锍甲磺酸盐、三苯基锍四氟硼酸盐、三(4-甲苯基)锍六氟磷酸盐、三(4-甲苯基)锍三氟甲烷磺酸盐和三乙基锍双(三氟甲基磺酰)亚胺中的至少一种。
5.根据权利要求1所述的正性光敏性树脂组合物,其特征在于:所述热交联剂选自含有环氧基团的化合物和/或含有羟甲基或烷氧基甲基的化合物;
所述含有环氧基团的化合物选自双酚A型环氧树脂、双酚F型环氧树脂、丙二醇二缩水甘油基醚、聚丙二醇二缩水甘油基醚、聚甲基(缩水甘油基氧基丙基)和含有环氧基的有机硅中的至少一种;
所述含有羟甲基或烷氧基甲基的化合物选自46DMOC、46DMOEP、DML-PC、DML-PEP、DML-OC、DML-OEP、DML-34X、DML-PTBP、DML-PCHP、DML-OCHP、DML-PFP、DML-PSBP、DML-POP、DML-MBOC、DMLMBPC、DML-MTrisPC、DML-BisOC-Z、DML-BisOCHP-Z、DML-BPC、DMLBisOC-P、DMOM-PC、DMOMPTBP、DMOM-MBPC、TriML-P、TriML-35XL、TML-HQ、TML-BP、TML-pp-BPF、TML-BPE、TML-BPA、TML-BPAF、TML-BPAP、TMOM-BP、TMOM-BPE、TMOM-BPA、TMOM-BPAF、TMOM-BPAP、HML-TPPHBA、HML-TPHAP、HMOM-TPPHBA、HMOM-TPHAP、“NIKALAC”MX-290、“NIKALAC”MX-280、“NIKALAC”MX-270、“NIKALAC”MX-279、“NIKALAC”MW-100LM和“NIKALAC”MX-750LM中的至少一种。
6.根据权利要求1所述的正性光敏性树脂组合物,其特征在于:所述助粘剂由含活泼环氧基团的偶联剂钝化所得;
所述含活泼环氧基团的偶联剂选自γ-缩水甘油醚氧基丙基三甲氧基硅烷、γ-缩水甘油醚氧基丙基三乙氧基硅烷、2-(3,4-环氧环己烷)乙基三甲氧基硅烷、2-(3,4-环氧环己烷)乙基三乙氧基硅烷、5,6-环氧己基三乙氧基硅烷、3-缩水甘油醚氧基丙基甲基二乙氧基硅烷、3-[(2,3)-环氧丙氧]丙基甲基二甲氧基硅烷、(3-环氧丙氧基丙基)二甲基乙氧基硅烷、环氧丁基三甲氧基硅烷和环氧丁基三乙氧基硅烷中的至少一种;
所述钝化使用的钝化剂选自N-氨基吗啉、N,N-二乙基乙二胺、N-氨乙基哌嗪、N-甲基乙二胺、巯基乙胺、2-氨基-4,5-二氢噻唑-4-酮、2-(乙硫基)乙胺、2-(硫代甲基)乙胺、3-甲基硫代丙胺、2-(硫代叔丁基)乙胺、4-(2-胺乙基)硫代吗啉和(2-吗啉-4-乙基)-肼和4-甲基-1-哌嗪乙胺中的至少一种;
所述显影抑制剂选自二苯基碘鎓硝酸盐、双(对叔丁基苯基)碘鎓硝酸盐、二苯基碘鎓溴化物、二苯基碘鎓氯化物和二苯基碘鎓碘化物中的至少一种;
所述有机溶剂选自N-甲基吡咯烷酮、N,N’-二甲基乙酰胺、N,N’-二甲基甲酰胺、二甲基亚砜、γ-丁内酯、乙酸乙酯、乙酸丁酯、乙酸正丙酯、乳酸甲酯、乳酸乙酯、乳酸丙酯、乳酸丁酯、甲苯、二甲苯、均三甲苯、二丙酮醇、甲基异丁基酮、环戊酮、环己酮、甲基乙基酮、甲基丙基酮、四氢呋喃、四氢吡喃、二氧六环、二氧杂环己烷、乙二醇单甲醚、乙二醇单甲醚乙酸酯、乙二醇单乙醚乙酸酯、丙二醇单甲醚、丙二醇单乙醚和丙二醇单甲醚乙酸酯中的至少一种。
7.权利要求1-6任一所述正性光敏性树脂组合物的制备方法,包括如下步骤:
搅拌条件下,所述正性光敏性树脂、所述光致产酸剂、所述热交联剂、所述助粘剂及所述显影抑制剂分批次加入所述有机溶剂中形成均相溶液,经过滤得到所述正性光敏性树脂组合物。
8.一种图案化聚苯并噁唑树脂薄膜的制备方法,包括如下步骤:
权利要求1-6任一所述正性光敏性树脂组合物经涂膜、曝光、显影、固化,形成图案化聚苯并噁唑树脂薄膜。
9.权利要求1-7任一所述正性光敏性树脂组合物作为半导体制造过程的芯片表面钝化、多层金属互连结构的层间绝缘、先进电子封装基板的多层布线及凸点/微焊球制作工艺、塑封电路的应力缓冲层膜中膜材料的应用。
10.根据权利要求9所述的应用,其特征在于:所述正性光敏性树脂组合物作为先进电子封装基板的Cu布线层中膜材料的应用。
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