TWI823230B - 聚醯亞胺樹脂、包括其之正型光敏性樹脂組成物以及製備其的方法 - Google Patents
聚醯亞胺樹脂、包括其之正型光敏性樹脂組成物以及製備其的方法 Download PDFInfo
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- TWI823230B TWI823230B TW111101923A TW111101923A TWI823230B TW I823230 B TWI823230 B TW I823230B TW 111101923 A TW111101923 A TW 111101923A TW 111101923 A TW111101923 A TW 111101923A TW I823230 B TWI823230 B TW I823230B
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- chemical formula
- polyimide resin
- bonded
- substituted
- resin
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- 229920001721 polyimide Polymers 0.000 title claims abstract description 109
- 239000009719 polyimide resin Substances 0.000 title claims abstract description 108
- 238000000034 method Methods 0.000 title claims abstract description 33
- 239000011342 resin composition Substances 0.000 title claims abstract description 31
- 239000000126 substance Substances 0.000 claims abstract description 83
- 125000000524 functional group Chemical group 0.000 claims abstract description 20
- 229920000642 polymer Polymers 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000000178 monomer Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 239000004094 surface-active agent Substances 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 10
- 239000003431 cross linking reagent Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 150000008065 acid anhydrides Chemical class 0.000 claims description 7
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 description 36
- 238000003786 synthesis reaction Methods 0.000 description 36
- 229910052751 metal Inorganic materials 0.000 description 26
- 239000002184 metal Substances 0.000 description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- -1 Cycloalkane radical Chemical class 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 description 6
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000004381 surface treatment Methods 0.000 description 5
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 4
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical group FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 description 4
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 4
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002861 polymer material Substances 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920002120 photoresistant polymer Polymers 0.000 description 3
- 229920006122 polyamide resin Polymers 0.000 description 3
- 229920006254 polymer film Polymers 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- JVERADGGGBYHNP-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JVERADGGGBYHNP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000007772 electroless plating Methods 0.000 description 2
- 238000009713 electroplating Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 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
- 125000005843 halogen group Chemical group 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- DMFAHCVITRDZQB-UHFFFAOYSA-N 1-propoxypropan-2-yl acetate Chemical compound CCCOCC(C)OC(C)=O DMFAHCVITRDZQB-UHFFFAOYSA-N 0.000 description 1
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- TVPNSPVSCKWFEU-UHFFFAOYSA-N 2-[[4-[2-[4-[1,1-bis[4-(oxiran-2-ylmethoxy)phenyl]ethyl]phenyl]propan-2-yl]phenoxy]methyl]oxirane Chemical compound C=1C=C(C(C)(C=2C=CC(OCC3OC3)=CC=2)C=2C=CC(OCC3OC3)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 TVPNSPVSCKWFEU-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- ZGDMDBHLKNQPSD-UHFFFAOYSA-N 2-amino-5-(4-amino-3-hydroxyphenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=C(N)C(O)=C1 ZGDMDBHLKNQPSD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- BKBZFJRHYSCZQA-UHFFFAOYSA-N 2-methoxy-2-methylpropanoic acid Chemical compound COC(C)(C)C(O)=O BKBZFJRHYSCZQA-UHFFFAOYSA-N 0.000 description 1
- ICPWFHKNYYRBSZ-UHFFFAOYSA-M 2-methoxypropanoate Chemical compound COC(C)C([O-])=O ICPWFHKNYYRBSZ-UHFFFAOYSA-M 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- ACQVEWFMUBXEMR-UHFFFAOYSA-N 4-bromo-2-fluoro-6-nitrophenol Chemical compound OC1=C(F)C=C(Br)C=C1[N+]([O-])=O ACQVEWFMUBXEMR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- AJQOASGWDCBKCJ-UHFFFAOYSA-N Butoxyacetic acid Chemical compound CCCCOCC(O)=O AJQOASGWDCBKCJ-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 1
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- DIQMPQMYFZXDAX-UHFFFAOYSA-N Pentyl formate Chemical compound CCCCCOC=O DIQMPQMYFZXDAX-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000004840 adhesive resin Substances 0.000 description 1
- 229920006223 adhesive resin Polymers 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 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
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- IWPATTDMSUYMJV-UHFFFAOYSA-N butyl 2-methoxyacetate Chemical compound CCCCOC(=O)COC IWPATTDMSUYMJV-UHFFFAOYSA-N 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
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- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Description
本申請案主張於2021年2月4日在韓國智慧財產局中提出申請的韓國專利申請案第10-2021-0015810號的優先權及權益,所述韓國專利申請案的全部內容併入本案供參考。
本申請案是有關於一種聚醯亞胺樹脂以及包括其之正型光敏性樹脂組成物。
目前,作為在用作可撓性印刷電路板及封裝介電材料的聚合物膜材料上形成金屬電路圖案的技術,已經普遍且廣泛使用藉由在使用光阻製程在其上堆疊或沈積薄銅箔的聚合物的表面上形成具有預定形狀的電路圖案、並對銅進行蝕刻來製備金屬電路圖案的方法。
作為在聚合物材料上形成金屬層的方法,已經使用積層法及鑄制法,其中藉由電漿離子對聚合物材料進行表面改質,且然後使用幹表面處理技術(例如濺射或金屬沈積)在聚合物的表
面上形成導電金屬接面層,且然後使用電鍍技術在導電金屬接面層的表面上形成金屬膜層,或者依據產品條件將銅箔直接結合至聚合物材料的表面。
最近,已經開發使用濕表面處理來對聚合物膜材料進行金屬化的製程,但是在此製程中,亦藉由在聚合物材料上形成金屬層且然後使用光阻製程對銅進行蝕刻來形成金屬電路。該些方法的問題在於不容易形成相對均勻的金屬層,且需要高的生產成本。
同時,與電鍍不同,無電鍍覆是一種藉由由溶液中包含的還原劑的氧化反應釋放的電子將金屬離子還原來沈積金屬膜而不使用直流(direct current,DC)電源的方法,且不僅選擇鍍覆溶液的組成物及處理條件非常重要,而且預處理亦非常重要。在多步驟無電鍍覆製程中,催化作用(catalyzation)步驟可以說是影響聚合物與金屬之間的物理性質及黏合強度的最重要的製程,所述催化作用步驟藉由使作為非導體的聚合物的表面活化而使金屬沈澱於聚合物基底的表面上。
然而,在聚合物材料的情況下,在加工期間產生的低潤濕性質及添加劑污染導致觸媒處理及鍍覆製程中的物理干擾及化學干擾,且因此,聚合物與金屬之間的黏合性變得非常低。
為了解決此問題,執行了許多表面處理技術,且通常已使用以下方法:使用氫氧化鉀溶液在聚合物的表面上誘導官能基的化學鍵等,且由於表面不規則性而增加表面積。
然而,上述表面處理技術具有複雜的製程條件,且僅藉由表面處理技術在增強聚合物與金屬之間的黏合性方面具有局限性。因此,在本領域中需要研究一種能夠提高聚合物與金屬之間黏合性的方法。
本申請案致力於提供一種聚醯亞胺樹脂以及包括其之正型光敏性樹脂組成物。
本申請案的示例性實施例提供
一種聚醯亞胺樹脂,其中由以下化學式1或化學式2表示的官能基鍵結至所述聚醯亞胺樹脂的至少一端。
在化學式1及化學式2中,
分別表示將鍵結至所述聚醯亞胺樹脂的位置,R1至R3各自獨立地為氫、經取代或未經取代的烷基、經取代或未經取代的芳基、或者經取代或未經取代的雜芳基,且R2及R3可彼此連接以形成環,且Ar1及Ar2各自獨立地為經取代或未經取代的雜芳基。
此外,本申請案的另一示例性實施例提供一種製備聚醯亞胺樹脂的方法,所述方法包括:製備其中由以下化學式10或化學式11表示的官能基鍵結至聚醯亞胺樹脂的至少一端的所述聚醯亞胺樹脂;以及使由化學式10或化學式11表示的官能基鍵結至的所述聚醯亞胺樹脂與包含硫醇基(-SH)的雜環化合物進行反應,
在化學式10及化學式11中分別表示將鍵結至所述聚醯亞胺樹脂的位置,且R1至R3各自獨立地為氫、經取代或未經取代的烷基、經取代或未經取代的芳基、或者經取代或未經取代的雜芳基,且R2及R3可彼此連接以形成環。
另外,本申請案的又一示例性實施例提供一種正型光敏性樹脂組成物,所述正型光敏性樹脂組成物包括:黏合劑樹脂,包含所述聚醯亞胺樹脂;光活性化合物;交聯劑;表面活性劑;以及溶劑。
根據本申請案的示例性實施例的聚醯亞胺樹脂的特徵在於,藉由在聚醯亞胺樹脂中直接包含對金屬具有優異黏合性的官能基,可提高對金屬的黏合強度。
因此,即使當光敏性樹脂組成物不包含單獨的黏合促進劑時,包含根據本申請案示例性實施例的聚醯亞胺樹脂的光敏性樹脂組成物亦可提高對金屬的黏合強度。
在下文中,將更詳細地闡述本申請案。
在本申請案中,當一個構件設置於另一構件「上」時,此不僅包括所述一個構件與另一構件接觸的情況,而且包括兩個構件之間存在又一構件的情況。
在本申請案中,當一部分「包含」一組成元素時,除非另有具體闡述,否則此並不意味著排除另一組成元素,而是意味著可更包含另一組成元素。
在本說明書中,「聚合物」意指由重複的重複單元(基本單元)組成的化合物。聚合物可由大分子或由大分子組成的化合物來表示。
根據本申請案的示例性實施例的聚醯亞胺樹脂的特徵在於,由以下化學式1或化學式2表示的官能基鍵結至所述聚醯亞胺樹脂的至少一端。
在化學式1及化學式2中,分別表示將鍵結至聚醯亞胺樹脂的位置,R1至R3各自獨立地為氫、經取代或未經取代的烷基、經取代或未經取代的芳基、或者經取代或未經取代的雜芳基,且R2及R3可彼此連接以形成環,且Ar1及Ar2各自獨立地為經取代或未經取代的雜芳基。
在本申請案的示例性實施例中,化學式1可由以下化學式3或化學式4表示。
在本申請案的示例性實施例中,化學式2可由以下化學式5至化學式9中的任一者表示。
在本申請案中,以下將闡述取代基的實例,但不限於此。
在本申請案中,用語「經取代或未經取代」意指經選自由以下組成的群組中的一或多個取代基取代或不具有取代基:氘;鹵素基;腈基;硝基;羥基;-COOH;烷氧基;烷基;環烷
基;烯基;環烯基;芳基;雜芳基;以及包含一或多個N、O、S或P原子的雜環基。
在本申請案中,鹵素基的實例包括氟、氯、溴或碘。
在本申請案中,烷氧基可為直鏈或支鏈,且碳原子數沒有特別限制,但可為1至30,具體而言為1至20,且更具體而言為1至10。
在本申請案中,烷基可為直鏈或支鏈,且其碳原子數沒有特別限制,但較佳為1至60。根據示例性實施例,烷基的碳原子數為1至30。根據另一示例性實施例,烷基的碳原子數為1至20。根據又一示例性實施例,烷基的碳原子數為1至10。烷基的具體實例包括甲基、乙基、正丙基、異丙基、正丁基、異丁基、第三丁基、正戊基、正己基、正庚基、正辛基等,但不限於此。
在本申請案中,環烷基沒有特別限制,但較佳為具有3至60個碳原子,且根據示例性實施例,環烷基的碳原子數為3至30。根據再一示例性實施例,環烷基的碳原子數為3至20。根據再一示例性實施例,環烷基的碳原子數為3至6。環烷基的具體實例包括環丙基、環丁基、環戊基、環己基、環庚基、環辛基等,但不限於此。
在本申請案中,烯基可為直鏈或支鏈,且其碳原子數沒有特別限制,但較佳為2至60。根據示例性實施例,烯基的碳原子數為2至30。根據另一示例性實施例,烯基的碳原子數為2至20。根據又一示例性實施例,烯基的碳原子數為2至10。烯基的
具體實例較佳為其中芳基(例如均二苯乙烯基(stylbenyl group)及苯乙烯基)被取代的烯基,但不限於此。
在本申請案中,環烯基沒有特別限制,但較佳為具有3至60個碳原子,且根據示例性實施例,環烯基的碳原子數為3至30。根據再一示例性實施例,環烯基的碳原子數為3至20。根據再一示例性實施例,環烯基的碳原子數為3至6。環烯基的實例較佳為環戊烯基及環己烯基,但不限於此。
在本申請案中,芳基沒有特別限制,但較佳為具有6至60個碳原子,且可為單環芳基或多環芳基。根據示例性實施例,芳基的碳原子數為6至30。根據示例性實施例,芳基的碳原子數為6至20。作為芳基的單環芳基的實例,包括苯基、聯苯基、三聯苯基等,但不限於此。多環芳基的實例包括萘基、蒽基、茚基、菲基、芘基、苝基、三苯基、基(chrysenyl group)、芴基等,但不限於此。
在本申請案中,雜環基是包含O、N或S作為雜原子的雜環基,且其碳原子數沒有特別限制,但為2至30,具體而言為2至20。雜環基的實例包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、三唑基、吡啶基、聯吡啶基、三嗪基、吖啶基、噠嗪基、喹啉基、異喹啉基、吲哚基、咔唑基、苯並噁唑基、苯並咪唑基、苯並噻唑基、苯並咔唑基、苯並噻吩基、二苯並噻吩基、苯並呋喃基、二苯並呋喃基、四氫吡喃基等,但不限於此。
在本申請案中,上述關於雜環基的說明可應用於除芳族雜芳基以外的雜芳基。
在本申請案的示例性實施例中,化學式1及化學式2的Ar1及Ar2可各自獨立地由以下結構式中的任一者表示。
在結構式中,*表示將鍵結至化學式1或化學式2的位置。
在本申請案的示例性實施例中,聚醯亞胺樹脂可包括胺系單體與酸酐系單體的聚合物產物。作為胺系單體與酸酐系單體的聚合製程,除使用以下將闡述的胺系單體及酸酐系單體之外,可使用本領域中已知的方法。
胺系單體可選自以下結構式,但不限於此。
酸酐系單體可選自以下結構式,但不限於此
在本申請案的示例性實施例中,聚醯亞胺樹脂可更包括以下結構式的單元。以下結構式可自包含以下結構式的胺系單體、包含以下結構式的酸酐系單體等引入至聚醯亞胺樹脂中等。
在結構式中,
*表示將鍵結至聚醯亞胺樹脂的位置,n各自獨立地為1至30的實數,且x、y及z各自獨立地為1至50的實數。
在本申請案的示例性實施例中,由化學式1或化學式2表示的官能基可鍵結至聚醯亞胺樹脂的兩端。此外,由化學式1或化學式2表示的官能基可鍵結至聚醯亞胺樹脂的任一端,且本領域中已知的端基可鍵結至聚醯亞胺樹脂的另一端。舉例而言,由化學式1或化學式2表示的官能基可鍵結至聚醯亞胺樹脂的任一端,且以下結構式的端基可鍵結至聚醯亞胺樹脂的另一端,但端基不限於此。
在結構式中,*分別表示將鍵結至聚醯亞胺樹脂的位置,且Ar3與Ar4彼此相同或不同,且各自獨立地為氫、羥基、或者經取代或未經取代的烷基。
在本申請案的示例性實施例中,聚醯亞胺樹脂可具有1,000克/莫耳至70,000克/莫耳、更佳為3,000克/莫耳至50,000克/莫耳的重量平均分子量。當聚醯亞胺樹脂的重量平均分子量小於1,000克/莫耳時,生成的聚合物膜可能易碎,且黏合強度可能
劣化。另外,當聚醯亞胺樹脂的重量平均分子量超過70,000克/莫耳時,靈敏度降低且聚醯亞胺樹脂可能不被顯影或可能殘留浮渣,而此並非較佳的。
重量平均分子量是其中分子量不均勻且任何聚合物材料的分子量用作參考的平均分子量中的一者,且是藉由將具有分子量分佈的聚合物化合物的組分分子種類的分子量按重量分數進行平均而獲得的值。
重量平均分子量可藉由凝膠滲透層析法(gel permeation chromatography,GPC)方法進行量測。
根據本申請案的示例性實施例的聚醯亞胺樹脂的特徵在於,藉由在聚醯亞胺樹脂中直接包含由化學式1或化學式2表示的官能基作為對金屬具有優異黏合性的官能基,可提高對金屬的黏合強度。
此外,本申請案的另一示例性實施例提供一種製備聚醯亞胺樹脂的方法,所述方法包括:製備聚醯亞胺樹脂,其中由以下化學式10或化學式11表示的官能基鍵結至聚醯亞胺樹脂的至少一端;以及使由化學式10或化學式11表示的官能基鍵結至的聚醯亞胺樹脂與包含硫醇基(-SH)的雜環化合物反應。
在化學式10及化學式11中,分別表示將鍵結至聚醯亞胺樹脂的位置,且R1至R3各自獨立地為氫、經取代或未經取代的烷基、經取代或未經取代的芳基、或者經取代或未經取代的雜芳基,且R2與R3可彼此連接以形成環。
在本申請案的示例性實施例中,在以下將闡述的實施例中具體對使聚醯亞胺樹脂與包含硫醇基(-SH)的雜環化合物反應的方法進行闡述,其中所述聚醯亞胺樹脂為由化學式10或化學式11表示的官能基鍵結至的聚醯亞胺樹脂。
在本申請案的示例性實施例中,包含硫醇基(-SH)的雜環化合物可選自以下化合物。
另外,本申請案的另一示例性實施例提供一種正型光敏性樹脂組成物,所述正型光敏性樹脂組成物包括:黏合劑樹脂,包含聚醯亞胺樹脂;光活性化合物;交聯劑;表面活性劑;以及溶劑。
在本申請案的示例性實施例中,基於100重量份的包含聚醯亞胺樹脂的黏合劑樹脂,可包含:1重量份至40重量份的光活性化合物;5重量份至50重量份的交聯劑;0.05重量份至5重量份的表面活性劑;以及50重量份至500重量份的溶劑。
當正型光敏性樹脂組成物中包含上述重量份範圍的各組成元素時,聚醯亞胺樹脂在鹼性顯影劑中顯影,且可不僅具有高的機械性質及耐熱性,而且提高對金屬的黏合強度。
光活性化合物具體可為醌二疊氮(quinonediazide)化合
物。作為醌二疊氮化合物,例如可使用由美源商事有限公司(Miwon Commercial Co.,Ltd.)製造的TPA529、THA515或PAC430,但是所述化合物不限於此。
交聯劑沒有特別限制,且只要交聯劑應用於本領域則可不受限制地使用。舉例而言,作為交聯劑,可使用由國都化工有限公司(Kukdo Chemical Co.,Ltd.)製造的2-[[4-[2-[4-[1,1-雙[4-(環氧乙烷-2-基甲氧基)苯基]乙基]苯基]丙-2-基]苯氧基]甲基]環氧乙烷、4,4'-亞甲基雙(N,N-雙(環氧乙烷-2-基甲基)苯胺)、YD-127、YD-128、YD-129、YDF-170、YDF-175及YDF-180,由迪愛生公司(DIC Corporation)製造的EXA-4850等。
表面活性劑是矽酮系表面活性劑或氟系表面活性劑,且具體而言,作為矽酮系表面活性劑,可使用由畢克化學有限公司(BYK-Chemie Co.,Ltd.)製造的BYK-077、BYK-085、BYK-300、BYK-301、BYK-302、BYK-306、BYK-307、BYK-310、BYK-320、BYK-322、BYK-323、BYK-325、BYK-330、BYK-331、BYK-333、BYK-335、BYK-341v344、BYK-345v346、BYK-348、BYK-354、BYK-355、BYK-356、BYK-358、BYK-361、BYK-370、BYK-371、BYK-375、BYK-380、BYK-390等,且作為氟系表面活性劑,可使用由大日本油墨化學工業有限公司(DaiNippon Ink & Chemicals,Inc.(DIC))製造的F-114、F-177、F-410、F-411、F-450、F-493、F-494、F-443、F-444、F-445、F-446、F-470、F-471、F-472SF、F-474、F-475、F-477、F-478、F-479、F-480SF、F-482、F-483、
F-484、F-486、F-487、F-172D、MCF-350SF、TF-1025SF、TF-1117SF、TF-1026SF、TF-1128、TF-1127、TF-1129、TF-1126、TF-1130、TF-1116SF、TF-1131、TF1132、TF1027SF、TF-1441、TF-1442等,但表面活性劑不限於此。
作為溶劑,可使用本發明所屬領域中已知的能夠形成光敏性樹脂組成物的化合物,而沒有特別限制。作為非限制性實例,溶劑可為選自由酯、醚、酮、芳烴及亞碸組成的群組中的一或多種化合物。
酯溶劑可為乙酸乙酯、乙酸正丁酯、乙酸異丁酯、甲酸戊酯、乙酸異戊酯、丙酸丁酯、丁酸異丙酯、丁酸乙酯、丁酸丁酯、乳酸甲酯、乳酸乙酯、γ-丁內酯、ε-己內酯、δ-戊內酯、烷基氧基乙酸酯(例如:甲基氧基乙酸酯、乙基氧基乙酸酯、丁基氧基乙酸酯(例如,甲氧基乙酸甲酯、甲氧基乙酸乙酯、甲氧基乙酸丁酯、乙氧基乙酸甲酯、乙氧基乙酸乙酯等))、3-氧基丙酸烷基酯(例如:3-氧基丙酸甲酯、3-氧基丙酸乙酯等(例如,3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸甲酯、3-乙氧基丙酸乙酯等))、2-氧基丙酸烷基酯(例如:2-氧基丙酸甲酯、2-氧基丙酸乙酯、2-氧基丙酸丙酯等(例如,2-甲氧基丙酸甲酯、2-甲氧基丙酸乙酯、2-甲氧基丙酸丙酯、2-乙氧基丙酸甲酯、2-乙氧基丙酸乙酯))、2-氧基-2-甲基丙酸甲酯及2-氧基-2-甲基丙酸乙酯(例如,2-甲氧基-2-甲基丙酸甲酯、2-乙氧基-2-甲基丙酸乙酯等)、丙酮酸甲酯、丙酮酸乙酯、丙酮酸丙酯、乙醯乙酸甲酯、乙醯乙酸
乙酯、2-氧代丁酸甲酯、2-氧代丁酸乙酯等。
醚溶劑可為二乙二醇二甲醚、四氫呋喃、乙二醇單甲醚、乙二醇單乙醚、甲基溶纖劑乙酸酯、乙基溶纖劑乙酸酯、二乙二醇單甲醚、二乙二醇單乙醚、二乙二醇單丁醚、丙二醇單甲醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙二醇單丙醚乙酸酯等。
酮溶劑可為甲基乙基酮、環己酮、環戊酮、2-庚酮、3-庚酮、N-甲基-2-吡咯啶酮等。
芳烴溶劑可為甲苯、二甲苯、大茴香醚、檸檬烯等。
亞碸溶劑可為二甲基亞碸等。
本申請案的另一示例性實施例提供一種包含正型光敏性樹脂組成物或其固化產物的絕緣膜。
絕緣膜可原樣包含正型光敏性樹脂組成物。
絕緣膜可包含正型光敏性樹脂組成物的固化產物。
用於對根據本申請案的示例性實施例的光敏性樹脂組成物進行固化的光源的實例包括汞蒸汽弧、碳弧、Xe弧等,其等發射波長為250奈米至450奈米的光,但不總是限於此。
視需要,在將正型光敏性樹脂組成物固化之後,絕緣膜可進一步經受對正型光敏性樹脂組成物進行熱處理的步驟。熱處理可藉由加熱工具(例如熱板、熱空氣循環爐及紅外線爐)來執行,且可在180℃至250℃或190℃至220℃的溫度下執行。
所述絕緣膜表現出優異的耐化學性及機械性質,且因此
可較佳地應用於半導體裝置的絕緣膜、用於重佈線層的層間絕緣膜等。此外,絕緣膜可應用於光阻、抗蝕劑、焊頂抗蝕劑等。
絕緣膜可包括支撐件或基底。
支撐件或基底沒有特別限制,且可使用本領域已知的支撐件或基底。舉例而言,可舉例說明用於電子組件的基底或在所述基底上形成的預定佈線圖案。基底的實例包括金屬(例如矽、氮化矽、鈦、鉭、鈀、鈦鎢、銅、鉻、鐵、鋁、金及鎳)基底、玻璃基底等。作為佈線圖案的材料,例如可使用銅、焊料、鉻、鋁、鎳、金等,但所述材料不限於此。
應用方法沒有特別限制,但可使用噴塗法、輥塗法、旋塗法等,且一般而言廣泛使用旋塗法。此外,形成應用膜,且然後在一些情況下,可在減壓下部分移除殘留溶劑。
在本申請案的示例性實施例中,絕緣膜可具有1微米至100微米的厚度。當滿足絕緣膜的厚度範圍時,可獲得不僅在本申請案中期望的耐化學性及機械性質方面優異而且在對金屬的黏合強度方面亦優異的絕緣膜。絕緣膜的厚度可使用掃描電子顯微鏡(scanning electron microscope,SEM)來量測。
本申請案的另一示例性實施例提供一種包括所述絕緣膜的半導體裝置。
除絕緣膜之外,可藉由更包括本領域中通常使用的各種部件來製造半導體裝置。
在下文中,將參照用於具體闡述本申請案的實例來詳細闡述本申請案。然而,根據本申請案的實例可以各種形式進行修改,且不解釋為將本申請案的範圍限定於下述實例。提供本申請案的實例是為了向熟習此項技術者更完整地闡釋本申請案。
<合成例1>聚醯亞胺樹脂A1的合成
在將100毫莫耳2,2-雙(3-胺基-4-羥基苯基)六氟丙烷(2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane,Bis-APAF)及300克丙二醇甲醚乙酸酯(PGMEA)依序添加至1,000毫升圓底燒瓶,將溫度升高至120℃並對所得混合物進行攪拌並使其完全溶解。將燒瓶冷卻至80℃,向其中添加97毫莫耳均苯四甲酸二酐(1,2,4,5-Benzenetetracarboxylic anhydride,PMDA)及6毫莫耳具有以下結構式的馬來酸酐(maleic anhydride,MA),且在150℃下將所得混合物與30克甲苯一起攪拌。在組分完全溶解後,將所得溶液冷卻至50℃,且然後用10克丙二醇單甲基乙酸酯對3毫莫耳γ戊內酯(gamma valerolactone,γ-VL)及7毫莫耳三乙胺進行稀釋,並將所得溶液引入至其中。在安裝迪安-斯塔克(Dean-Stark)蒸餾設備使得水可藉由所述設備在反應中移除後,將混合物在175℃下攪拌16小時。在將添加至混合溶液的甲苯移除後,將溶液冷卻至室溫並回收。使用凝膠滲透層析法(GPC)確認回收的聚合物的重量平均分子量(weight average molecular weight,Mw),且確定為16,112克/莫耳。另外,製備的聚合物的
多分散性指數(polydispersity index,PDI)為2.18。
<合成例2>聚醯亞胺樹脂B1的合成
除分別使用2,2'-雙(三氟甲基)-4,4'-二胺基聯苯(2,2'-bis(trifluoromethyl)benzidine,TFMB)及聯苯基-四羧酸二酐(biphenyltetracarboxylic di-anhydride,BPDA)代替Bis-APAF及PMDA之外,以與聚醯亞胺樹脂A1的合成中相同的方式合成聚醯亞胺樹脂B1。回收的聚合物的重量平均分子量(Mw)及多分散性指數(PDI)分別為15,998克/莫耳及2.16。
<合成例3>聚醯亞胺樹脂C1的合成
除使用50毫莫耳Bis-APAF及50毫莫耳4,4'-二胺基二苯醚(4,4'-diaminodiphenyl ether,ODA)代替100毫莫耳Bis-APAF、以及使用47毫莫耳PMDA及50毫莫耳4,4'-氧雙鄰苯二甲酸酐(4,4-Oxydiphthalic anhydride,ODPA)代替97毫莫耳PMDA之外,以與聚醯亞胺樹脂A1的合成中相同的方式合成聚醯亞胺樹脂C1。回收的聚合物的重量平均分子量(Mw)及多分散性指數(PDI)分別為18,055克/莫耳及2.29。
<合成例4>聚醯亞胺樹脂D1的合成
除使用50毫莫耳TFMB及50毫莫耳3,3-二羥基聯苯胺(3,3'-Dihydroxybenzidine,HAB)代替100毫莫耳Bis-APAF、以及使用47毫莫耳BPDA及50毫莫耳ODPA代替97毫莫耳PMDA之外,以與聚醯亞胺樹脂A1的合成中相同的方式合成聚合物樹脂D1。回收的聚合物的重量平均分子量(Mw)及多分散性指數(PDI)分別為14,911克/莫耳及2.62。
<合成例5>聚醯亞胺樹脂E1的合成
除使用50毫莫耳Bis-APAF及50毫莫耳聚醚胺(ED-900,吉夫胺(Jeffamine))代替100毫莫耳Bis-APAF、以及使用ODPA代替PMDA之外,以與聚醯亞胺樹脂A1的合成中相同的方式合成聚醯亞胺樹脂E1。回收的聚合物的重量平均分子量(Mw)及多分散性指數(PDI)分別為15,618克/莫耳及2.26。
<合成例6>聚醯亞胺樹脂A2的合成
除使用以下結構式的iBF代替MA之外,以與聚醯亞胺樹脂A1的合成中相同的方式合成聚醯亞胺樹脂A2。回收的聚合物的重量平均分子量(Mw)及多分散性指數(PDI)分別為18,485克/莫耳及2.46。
<合成例7>聚醯亞胺樹脂B2的合成
除使用iBF代替MA之外,以與聚醯亞胺樹脂B1的合成中相同的方式合成聚醯亞胺樹脂B2。回收的聚合物的重量平均分子量(Mw)及多分散性指數(PDI)分別為17,489克/莫耳及2.41。
<合成例8>聚醯亞胺樹脂C2的合成
除使用iBF代替MA之外,以與聚醯亞胺樹脂C1的合成中相同的方式合成聚醯亞胺樹脂C2。回收的聚合物的重量平均分子量(Mw)及多分散性指數(PDI)分別為17,918克/莫耳及2.45。
<合成例9>聚醯亞胺樹脂D2的合成
除使用iBF代替MA之外,以與聚醯亞胺樹脂D1的合成中相同的方式合成聚醯亞胺樹脂D2。回收的聚合物的重量平均分子量(Mw)及多分散性指數(PDI)分別為18,007克/莫耳及2.46。
<合成例10>聚醯亞胺樹脂E2的合成
除使用iBF代替MA之外,以與聚醯亞胺樹脂E1的合成中相同的方式合成聚醯亞胺樹脂E2。回收的聚合物的重量平均分子量(Mw)及多分散性指數(PDI)分別為15,152克/莫耳及2.12。
<合成例11>聚醯亞胺樹脂A3的合成
除使用3-胺基吡啶(3-Aminopyridine,3AP)代替MA
之外,以與聚醯亞胺樹脂A1的合成中相同的方式合成聚醯亞胺樹脂A3。回收的聚合物的重量平均分子量(Mw)及多分散性指數(PDI)分別為17,475克/莫耳及2.35。
<合成例12>聚醯亞胺樹脂B3的合成
除使用聚醯胺(Polyamide,PA)代替MA之外,以與聚醯亞胺樹脂B1的合成中相同的方式合成聚醯亞胺樹脂B3。回收的聚合物的重量平均分子量(Mw)及多分散性指數(PDI)分別為16,341克/莫耳及2.23。
<實例1至實例20>
1)聚醯亞胺樹脂及硫醇的合成
將以下表1中所示的2當量硫醇化合物及1當量聚醯亞胺樹脂以及0.1當量光起始劑(二苯甲酮)放入燒瓶中,並在室溫下用350奈米的紫外(ultraviolet,UV)照射4小時。在反應後,將聚醯亞胺溶解於四氫呋喃(Tetrahydrofuran,THF)中,並使用己烷捕獲沈澱,以移除未反應的物質及雜質。
2)正型光敏性樹脂組成物的製備
以1)中製備的100重量份的聚醯亞胺樹脂計,藉由將15重量份的光活性化合物(TPA529)、25重量份的交聯劑(2-[[4-[2-[4-[1,1-雙[4-(環氧乙烷-2-基甲氧基)苯基]乙基]苯基]丙-2-基]苯氧基]甲基]環氧乙烷)、0.1重量份的表面活性劑(BYK-307,由畢克化學製造)及200重量份的溶劑(PGMEA)混合來製備正型光敏性樹脂組成物。
<比較例1至比較例5>
除應用以下表1中所示的聚醯亞胺樹脂之外,以與實例中相同的方式製備正型光敏性樹脂組成物。
<比較例6及比較例7>
除應用以下表1中所示的聚醯亞胺樹脂並以1當量的聚醯亞胺樹脂計添加2當量的硫醇化合物T1之外,以與實例中相同的方式製備正型光敏性樹脂組成物。
實例及比較例中製備的正型光敏性樹脂組成物能夠經過0.2微米過濾器,並藉由移除溶液中的雜質進行評估。
使用在其上氣相沈積至100奈米或大於100奈米的厚度的Ti及Cu的晶圓,使用所製備的正型光敏性樹脂組成物對晶圓進行旋塗,並塗佈至6微米的厚度後,藉由在105℃或大於105℃的溫度下進行烘烤以移除溶劑來完全移除殘留在晶圓上的溶劑。在使用發射i線(i-line)波長的步進機以100毫焦耳/平方厘米(mJ/cm2)至900毫焦耳/平方厘米的恆定曝光對晶圓進行照射之後,使用顯影劑對晶圓進行顯影達120秒,經歷使用沖洗溶液的沖洗製程,且然後在200℃或小於200℃的溫度下進行後烘烤達2小時。
[正型光敏性樹脂組成物的評估條件]
預烘烤:105℃/120秒
曝光:i-線步進機,100毫焦耳/平方厘米至900毫焦耳/平方
厘米
顯影:2.38重量%氫氧化四甲銨(TMAH)溶液,23℃/120秒
沖洗:去離子(deionized,DI)水沖洗
後烘烤:200℃/2小時
使用已經完全後烘烤的晶圓來確認圖案特性,將塗佈在晶圓上的光敏性樹脂組成物固化,且然後形成膜,並量測其機械性質及熱特性。
對於圖案可顯影性,使用掃描電子顯微鏡(SEM)來量測圖案的形狀及大小,且使用萬能試驗機(universal testing machine,UTM)來量測機械性質。
[圖案可顯影性]
藉由使用SEM來量測自5微米的厚度至10微米的接觸孔圖案下部部分的完全顯影部分來量測圖案的形狀及大小,且將其中10微米的孔圖案完全顯影的情況闡述為良好。將其中圖案下部部分未顯影的情況闡述為差。
良好:◎
次級:△
差:X
[黏合強度]
在使用樹脂塗佈晶圓並將樹脂固化之後,使用單刃刀片在膜上以2毫米的間隔切割10列、10行的格子形狀。藉由使用玻
璃紙膠帶(註冊商標)剝離來對其上部的100個單元中剝離的單元數進行計數,以對金屬材料與樹脂固化膜之間的黏合特性進行評估。
小於10:◎
10或大於10且小於20:△
20或大於20:X
如結果中所示,根據本申請案的示例性實施例的聚醯亞胺樹脂的特徵在於,藉由在聚醯亞胺樹脂中直接包含對金屬具有優異黏合性的官能基,可提高對金屬的黏合強度。
此外,比較例6及比較例7是其中硫醇化合物單獨包含於光敏性樹脂組成物中的情況,而並非如本申請案的實例中所示般應用其中硫醇系官能基直接鍵結至聚醯亞胺樹脂的聚醯亞胺樹脂。如結果中所示,可確認在比較例6及比較例7的情況下,當與本申請案的實例相比時,圖案可顯影性及黏合強度特性不佳。
因此,即使當光敏性樹脂組成物不包含單獨的黏合促進劑時,包含根據本申請案的示例性實施例的聚醯亞胺樹脂的光敏性樹脂組成物亦可提高對金屬的黏合強度。
Claims (9)
- 如請求項1所述的聚醯亞胺樹脂,其中所述聚醯亞胺樹脂包含胺系單體與酸酐系單體的聚合物產物。
- 一種正型光敏性樹脂組成物,包括:黏合劑樹脂,包含如請求項1至6中任一項所述的聚醯亞胺樹脂;光活性化合物;交聯劑;表面活性劑;以及溶劑。
- 如請求項8所述的正型光敏性樹脂組成物,其中以100重量份的包含所述聚醯亞胺樹脂的所述黏合劑樹脂計,包含1重量份至40重量份的所述光活性化合物;5重量份至50重量份的所述交聯劑;0.05重量份至5重量份的所述表面活性劑;以及 50重量份至500重量份的所述溶劑。
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CN107709407A (zh) * | 2015-05-29 | 2018-02-16 | 富士胶片株式会社 | 聚酰亚胺前体组合物、感光性树脂组合物、固化膜、固化膜的制造方法、半导体器件及聚酰亚胺前体组合物的制造方法 |
TW201927982A (zh) * | 2017-10-11 | 2019-07-16 | 南韓商塔科馬科技有限公司 | 黏合樹脂及包含其的光敏樹脂組成物或塗覆溶液 |
CN110147031A (zh) * | 2012-12-20 | 2019-08-20 | 东丽株式会社 | 感光性树脂组合物、耐热性树脂膜的制造方法及显示装置 |
US20200004150A1 (en) * | 2018-06-27 | 2020-01-02 | Tokyo Ohka Kogyo Co., Ltd. | Chemically amplified positive-type photosensitive resin composition, photosensitive dry film, method of manufacturing photosensitive dry film, method of manufacturing patterned resist film, method of manufacturing substrate with template, method of manufacturing plated article, and nitrogen-containing aromatic heterocyclic compound |
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CN110147031A (zh) * | 2012-12-20 | 2019-08-20 | 东丽株式会社 | 感光性树脂组合物、耐热性树脂膜的制造方法及显示装置 |
CN107709407A (zh) * | 2015-05-29 | 2018-02-16 | 富士胶片株式会社 | 聚酰亚胺前体组合物、感光性树脂组合物、固化膜、固化膜的制造方法、半导体器件及聚酰亚胺前体组合物的制造方法 |
TW201927982A (zh) * | 2017-10-11 | 2019-07-16 | 南韓商塔科馬科技有限公司 | 黏合樹脂及包含其的光敏樹脂組成物或塗覆溶液 |
US20200004150A1 (en) * | 2018-06-27 | 2020-01-02 | Tokyo Ohka Kogyo Co., Ltd. | Chemically amplified positive-type photosensitive resin composition, photosensitive dry film, method of manufacturing photosensitive dry film, method of manufacturing patterned resist film, method of manufacturing substrate with template, method of manufacturing plated article, and nitrogen-containing aromatic heterocyclic compound |
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