CN114957660A - Polyimide resin composition, polyimide resin adhesive layer, laminate, and method for producing electronic component - Google Patents
Polyimide resin composition, polyimide resin adhesive layer, laminate, and method for producing electronic component Download PDFInfo
- Publication number
- CN114957660A CN114957660A CN202110217082.5A CN202110217082A CN114957660A CN 114957660 A CN114957660 A CN 114957660A CN 202110217082 A CN202110217082 A CN 202110217082A CN 114957660 A CN114957660 A CN 114957660A
- Authority
- CN
- China
- Prior art keywords
- polyimide resin
- formula
- diamine
- resin composition
- group
- 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.)
- Pending
Links
- 229920001721 polyimide Polymers 0.000 title claims abstract description 148
- 239000009719 polyimide resin Substances 0.000 title claims abstract description 148
- 239000000203 mixture Substances 0.000 title claims abstract description 76
- 239000012790 adhesive layer Substances 0.000 title claims abstract description 44
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 30
- 150000004985 diamines Chemical class 0.000 claims abstract description 121
- 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 claims abstract description 32
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims abstract description 23
- 239000000758 substrate Substances 0.000 claims description 65
- 239000010410 layer Substances 0.000 claims description 56
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 9
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 26
- 239000000126 substance Substances 0.000 abstract description 18
- 238000006116 polymerization reaction Methods 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 14
- 239000011521 glass Substances 0.000 description 12
- 239000004065 semiconductor Substances 0.000 description 10
- 125000000962 organic group Chemical group 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000006297 dehydration reaction Methods 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- UHIDYCYNRPVZCK-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C(N)=CC=1C(C)(C)C1=CC=C(O)C(N)=C1 UHIDYCYNRPVZCK-UHFFFAOYSA-N 0.000 description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- GPXCORHXFPYJEH-UHFFFAOYSA-N 3-[[3-aminopropyl(dimethyl)silyl]oxy-dimethylsilyl]propan-1-amine Chemical compound NCCC[Si](C)(C)O[Si](C)(C)CCCN GPXCORHXFPYJEH-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- OAXARSVKYJPDPA-UHFFFAOYSA-N tert-butyl 4-prop-2-ynylpiperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(CC#C)CC1 OAXARSVKYJPDPA-UHFFFAOYSA-N 0.000 description 5
- KHYXYOGWAIYVBD-UHFFFAOYSA-N 4-(4-propylphenoxy)aniline Chemical compound C1=CC(CCC)=CC=C1OC1=CC=C(N)C=C1 KHYXYOGWAIYVBD-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- -1 1,3-bis- (2-aminoethylaminomethyl) tetramethyldisiloxane (1,3-bis- (2-aminoethylaminomethyl) tetramethyldisiloxane) Chemical compound 0.000 description 3
- GBDDTZWLDWKSAX-UHFFFAOYSA-N 1-ethylpiperidine Chemical compound CCN1CCCCC1.CCN1CCCCC1 GBDDTZWLDWKSAX-UHFFFAOYSA-N 0.000 description 3
- FJVIHKKXPLPDSV-UHFFFAOYSA-N 4-phenoxybenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1OC1=CC=CC=C1 FJVIHKKXPLPDSV-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 239000002981 blocking agent Substances 0.000 description 3
- 239000003292 glue Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000003825 pressing Methods 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- FFWNCSWLUYKKKA-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1.NC1=CC=CC(O)=C1 FFWNCSWLUYKKKA-UHFFFAOYSA-N 0.000 description 2
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
- LJMPOXUWPWEILS-UHFFFAOYSA-N 3a,4,4a,7a,8,8a-hexahydrofuro[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1C2C(=O)OC(=O)C2CC2C(=O)OC(=O)C21 LJMPOXUWPWEILS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 229920005575 poly(amic acid) Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 229910052594 sapphire Inorganic materials 0.000 description 2
- 239000010980 sapphire Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 239000013585 weight reducing agent Substances 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-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
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- BJINVQNEBGOMCR-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl acetate Chemical compound COCCOCCOC(C)=O BJINVQNEBGOMCR-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
- QRUWUSOUUMPANJ-UHFFFAOYSA-N 2-amino-5-[(4-amino-3-carboxyphenyl)methyl]benzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC=C1CC1=CC=C(N)C(C(O)=O)=C1 QRUWUSOUUMPANJ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- HHCHLHOEAKKCAB-UHFFFAOYSA-N 2-oxaspiro[3.5]nonane-1,3-dione Chemical compound O=C1OC(=O)C11CCCCC1 HHCHLHOEAKKCAB-UHFFFAOYSA-N 0.000 description 1
- HCGFUIQPSOCUHI-UHFFFAOYSA-N 2-propan-2-yloxyethanol Chemical compound CC(C)OCCO HCGFUIQPSOCUHI-UHFFFAOYSA-N 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical compound NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 description 1
- WCXGOVYROJJXHA-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)S(=O)(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 WCXGOVYROJJXHA-UHFFFAOYSA-N 0.000 description 1
- RSFDFESMVAIVKO-UHFFFAOYSA-N 3-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=CC(S)=C1 RSFDFESMVAIVKO-UHFFFAOYSA-N 0.000 description 1
- QMWGSOMVXSRXQX-UHFFFAOYSA-N 3-sulfobenzoic acid Chemical compound OC(=O)C1=CC=CC(S(O)(=O)=O)=C1 QMWGSOMVXSRXQX-UHFFFAOYSA-N 0.000 description 1
- TWISHTANSAOCNX-UHFFFAOYSA-N 4-(1,1,1,3,3,3-hexafluoropropan-2-yl)phthalic acid Chemical compound OC(=O)C1=CC=C(C(C(F)(F)F)C(F)(F)F)C=C1C(O)=O TWISHTANSAOCNX-UHFFFAOYSA-N 0.000 description 1
- VILWHDNLOJCHNJ-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)sulfanylphthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1SC1=CC=C(C(O)=O)C(C(O)=O)=C1 VILWHDNLOJCHNJ-UHFFFAOYSA-N 0.000 description 1
- AVCOFPOLGHKJQB-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)sulfonylphthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 AVCOFPOLGHKJQB-UHFFFAOYSA-N 0.000 description 1
- IWXCYYWDGDDPAC-UHFFFAOYSA-N 4-[(3,4-dicarboxyphenyl)methyl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C(C(O)=O)=C1 IWXCYYWDGDDPAC-UHFFFAOYSA-N 0.000 description 1
- SSDBTLHMCVFQMS-UHFFFAOYSA-N 4-[4-(1,1,1,3,3,3-hexafluoropropan-2-yl)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C(C(F)(F)F)C(F)(F)F)C=C1 SSDBTLHMCVFQMS-UHFFFAOYSA-N 0.000 description 1
- UTDAGHZGKXPRQI-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(S(=O)(=O)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 UTDAGHZGKXPRQI-UHFFFAOYSA-N 0.000 description 1
- CCTOEAMRIIXGDJ-UHFFFAOYSA-N 4-hydroxy-2-benzofuran-1,3-dione Chemical compound OC1=CC=CC2=C1C(=O)OC2=O CCTOEAMRIIXGDJ-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- AQVOMFPTJXMAQE-UHFFFAOYSA-N 4-propylphthalic acid Chemical compound CCCC1=CC=C(C(O)=O)C(C(O)=O)=C1 AQVOMFPTJXMAQE-UHFFFAOYSA-N 0.000 description 1
- LMJXSOYPAOSIPZ-UHFFFAOYSA-N 4-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=C(S)C=C1 LMJXSOYPAOSIPZ-UHFFFAOYSA-N 0.000 description 1
- HWAQOZGATRIYQG-UHFFFAOYSA-N 4-sulfobenzoic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C=C1 HWAQOZGATRIYQG-UHFFFAOYSA-N 0.000 description 1
- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 description 1
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
- NYYMNZLORMNCKK-UHFFFAOYSA-N 5-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1O NYYMNZLORMNCKK-UHFFFAOYSA-N 0.000 description 1
- SMAMQSIENGBTRV-UHFFFAOYSA-N 5-hydroxynaphthalene-2-carboxylic acid Chemical compound OC1=CC=CC2=CC(C(=O)O)=CC=C21 SMAMQSIENGBTRV-UHFFFAOYSA-N 0.000 description 1
- VTUGNNIWJSWUSP-UHFFFAOYSA-N 5-sulfanylnaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1S VTUGNNIWJSWUSP-UHFFFAOYSA-N 0.000 description 1
- NQSLRCGJQDKCHO-UHFFFAOYSA-N 5-sulfanylnaphthalene-2-carboxylic acid Chemical compound SC1=CC=CC2=CC(C(=O)O)=CC=C21 NQSLRCGJQDKCHO-UHFFFAOYSA-N 0.000 description 1
- ZPCQQOXOXNMOIJ-UHFFFAOYSA-N 8-hydroxynaphthalene-2-carboxylic acid Chemical compound C1=CC=C(O)C2=CC(C(=O)O)=CC=C21 ZPCQQOXOXNMOIJ-UHFFFAOYSA-N 0.000 description 1
- PRRFQAVIPFFRRL-UHFFFAOYSA-N 8-sulfanylnaphthalene-2-carboxylic acid Chemical compound C1=CC=C(S)C2=CC(C(=O)O)=CC=C21 PRRFQAVIPFFRRL-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- OBCCPLPLEJDJPG-UHFFFAOYSA-N NC=1C=C(C=CC1O)C(C(F)(F)F)(C(F)(F)F)C1=CC(=C(C=C1)O)N.NC=1C=C(C=CC1O)C(C(F)(F)F)C(F)(F)F Chemical compound NC=1C=C(C=CC1O)C(C(F)(F)F)(C(F)(F)F)C1=CC(=C(C=C1)O)N.NC=1C=C(C=CC1O)C(C(F)(F)F)C(F)(F)F OBCCPLPLEJDJPG-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- NIDNOXCRFUCAKQ-UHFFFAOYSA-N bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1C2C=CC1C(C(=O)O)C2C(O)=O NIDNOXCRFUCAKQ-UHFFFAOYSA-N 0.000 description 1
- CJYIPJMCGHGFNN-UHFFFAOYSA-N bicyclo[2.2.1]heptane-2,3,5,6-tetracarboxylic acid Chemical compound C1C2C(C(O)=O)C(C(=O)O)C1C(C(O)=O)C2C(O)=O CJYIPJMCGHGFNN-UHFFFAOYSA-N 0.000 description 1
- JOEPQSIPGWRIJU-UHFFFAOYSA-N bicyclo[2.2.2]oct-3-ene-2,3,5,6-tetracarboxylic acid Chemical compound C1CC2=C(C(O)=O)C(C(O)=O)C1C(C(=O)O)C2C(O)=O JOEPQSIPGWRIJU-UHFFFAOYSA-N 0.000 description 1
- XQBSPQLKNWMPMG-UHFFFAOYSA-N bicyclo[2.2.2]octane-2,3,5,6-tetracarboxylic acid Chemical compound C1CC2C(C(O)=O)C(C(=O)O)C1C(C(O)=O)C2C(O)=O XQBSPQLKNWMPMG-UHFFFAOYSA-N 0.000 description 1
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- WOSVXXBNNCUXMT-UHFFFAOYSA-N cyclopentane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)C1C(O)=O WOSVXXBNNCUXMT-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1075—Partially aromatic polyimides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/106—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing silicon
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09J179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/67—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere
- H01L21/683—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere for supporting or gripping
- H01L21/6835—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/005—Processes
- H01L33/0095—Post-treatment of devices, e.g. annealing, recrystallisation or short-circuit elimination
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2221/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof covered by H01L21/00
- H01L2221/67—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere
- H01L2221/683—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping
- H01L2221/68304—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support
- H01L2221/6835—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support used as a support during build up manufacturing of active devices
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2221/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof covered by H01L21/00
- H01L2221/67—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere
- H01L2221/683—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping
- H01L2221/68304—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support
- H01L2221/68381—Details of chemical or physical process used for separating the auxiliary support from a device or wafer
- H01L2221/68386—Separation by peeling
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Computer Hardware Design (AREA)
- Manufacturing & Machinery (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
The invention provides a polyimide resin composition, a polyimide resin adhesive layer, a laminate, and a method for manufacturing an electronic component. The polyimide resin composition comprises a polyimide resin, wherein the polyimide resin is substantially obtained by a polymerization reaction of a diamine A and a tetracarboxylic dianhydride B. The diamine A includes a diamine A-1 represented by the following formula (I-1) and a diamine A-2 represented by the following formula (I-2), wherein the molar ratio of the diamine A-1 to the diamine A-2 (A-1: A-2) is 0.1: 0.2 to 0.6. The polyimide resin composition has good chemical resistance and adhesiveness, and is suitable for manufacturing electronic components.
Description
Technical Field
The present invention relates to a resin composition, an adhesive layer, a laminate, and a method for manufacturing an electronic component, and particularly relates to a polyimide resin composition, a polyimide resin adhesive layer, a laminate, and a method for manufacturing an electronic component.
Background
In recent years, with the progress of weight reduction and thickness reduction of electronic devices, in order to meet the demand for electronic devices and facilitate subsequent packaging, the thickness of a substrate applied to the electronic devices is reduced to 1 μm or more and 100 μm or less, and then processed. In the processing step, in order to prevent the electronic device forming substrate from cracking, the electronic device forming substrate is usually fixed to a supporting substrate via a temporary adhesive by means of mechanical pressing, and after the processing step is completed, the processed electronic device forming substrate is peeled from the supporting substrate. Finally, the residual glue on the substrate and the supporting substrate is removed by organic solvent or alkaline solution.
In recent years, with the progress of weight reduction and thickness reduction of electronic devices, in order to meet the demand for electronic devices and facilitate subsequent packaging, the thickness of a substrate applied to the electronic devices is reduced to 1 μm or more and 100 μm or less, and then processed. In the processing step, in order to prevent the electronic device forming substrate from cracking, the electronic device forming substrate is usually fixed to a supporting substrate via a temporary adhesive by means of mechanical pressing, and after the processing step is completed, the processed electronic device forming substrate is peeled off from the supporting substrate. Finally, the residual glue on the substrate and the supporting substrate is removed by organic solvent or alkaline solution.
Disclosure of Invention
In view of the above, the present invention provides a polyimide resin composition having good chemical resistance and adhesion, a polyimide resin adhesive layer formed from the polyimide resin composition, a laminate including the polyimide resin adhesive layer, and a method for manufacturing an electronic component.
The present invention provides a polyimide resin composition comprising: a polyimide resin which is substantially obtained by polymerizing a diamine (A) and a tetracarboxylic dianhydride (B). The diamine (A) includes a diamine (A-1) represented by the following formula (I-1) and a diamine (A-2) represented by the following formula (I-2), wherein the molar ratio of the diamine (A-1) to the diamine (A-2) ((A-1): (A-2)) is 0.1: 0.2 to 0.6.
In the formula (I-1), m1 and m2 are each an integer of 1 to 3, X 1 Each is an alkyl group or an phenylene group having 1 to 5 carbon atoms, wherein when X is 1 When the alkyl group has 1 to 5 carbon atoms, -CH-is any one of the alkyl groups having 1 to 5 carbon atoms 2 -may be substituted by-NH-.
In the formula (I-2), X 2 Is a hydrocarbon group having 1 to 10 carbon atoms, -O-, -S-, -SO 2 -、-NH-、-C(CF 3 ) 2 -or
In an embodiment of the present invention, the diamine (A) further comprises a diamine (A-3) represented by the following formula (I-3), and a molar ratio of the diamine (A) to the diamine (A-3) ((A): (A-3)) is 1: greater than 0 to 4 or less.
In the formula (I-3), Y is-C (CH) 3 ) 2 -、-C(CF 3 ) 2 -、-CH 2 -, -O-, -S-, or-SO 2 -。
In an embodiment of the invention, the diamine (a) further includes 3,4' -diaminodiphenyl ether.
In an embodiment of the invention, the tetracarboxylic dianhydride (B) includes 3,3',4,4' -diphenyl ether tetracarboxylic dianhydride.
The present invention also provides a polyimide resin composition comprising: a polyimide resin comprising a structural unit represented by the general formula (1).
In the formula (1), Ar 1 Is a tetravalent organic radical, Ar 2 Is a group represented by the following formula (1-1) or a group represented by the following formula (1-2), wherein the molar ratio of the group represented by the formula (1-1) to the group represented by the formula (1-2) is 0.1: 0.2 to 0.6.
In the formula (1-1), m1 and m2 are each an integer of 1 to 3, X 1 Each is an alkyl group or an phenylene group having 1 to 5 carbon atoms, wherein when X is 1 When the alkyl group has 1 to 5 carbon atoms, -CH-is any one of the alkyl groups having 1 to 5 carbon atoms 2 -may be substituted by-NH-representing a bonding site.
In the formula (1-2), X 2 Is a hydrocarbon group having 1 to 10 carbon atoms, -O-, -S-, -SO 2 -、-NH-、-C(CF 3 ) 2 -or
Denotes a bonding site.
In an embodiment of the invention, the polyimide resin further includes a structural unit represented by a general formula (2).
In the formula (2), Ar 1 Is a tetravalent organic radical, Ar 3 Is a group represented by the following formula (2-1), wherein the molar ratio of the group represented by the formula (1-1) to the group represented by the formula (2-1) is 1: greater than 0 to 4 or less.
In the formula (2-1), Y is-C (CH) 3 ) 2 -、-C(CF 3 ) 2 -、-CH 2 -, -O-, -S-, or-SO 2 -.
In an embodiment of the invention, the polyimide resin further includes a structural unit represented by a general formula (3).
In the formula (3), Ar 1 Is a tetravalent organic radical, Ar 4 Is a group represented by the following formula (3-1).
In the formula (3-1), the symbol represents a bonding site.
In an embodiment of the present invention, Ar1 in the above formulas (1) to (3) is a group represented by the following formula (1-a),
in the formula (1-a), a indicates a bonding position.
The invention provides a polyimide resin adhesive layer, which is formed by the polyimide resin composition.
The present invention provides a laminate body comprising: the polyimide resin adhesive layer has a first surface and a second surface opposite to each other; the first substrate is attached to the first surface of the polyimide resin adhesive layer; the release layer is provided with a third surface and a fourth surface which are opposite to each other, and the third surface of the release layer is attached to the second surface of the polyimide resin adhesion layer; the second substrate is attached to the fourth surface of the release layer; and the electronic component is embedded in the polyimide resin adhesion layer and is connected with the release layer.
The invention provides a method for manufacturing an electronic component, which comprises the following steps: providing the laminate as described above; removing the release layer and the second substrate from the laminate to expose the second surface of the polyimide resin adhesive layer and a portion of the electronic component; and removing the polyimide resin adhesive layer and the first substrate.
In an embodiment of the invention, the electronic component is a light emitting diode.
In view of the above, the present invention provides a polyimide resin composition comprising a polyimide resin composition prepared by reacting a diamine having a siloxane bond and a diamine having four benzene rings in a molar ratio of 0.1: 0.2 to 0.6 diamine, and the polyimide resin composition has good chemical resistance and adhesion, and is therefore suitable for the production of electronic components. Also disclosed are a polyimide resin adhesive layer formed from such a polyimide resin composition, a laminate comprising such a temporary adhesive layer, and a method for producing an electronic component.
Drawings
The accompanying drawings are included to provide a further understanding of the invention, and are incorporated in and constitute a part of this specification. The drawings illustrate embodiments of the invention and together with the description serve to explain the principles of the invention.
FIG. 1 is a flow chart of a method of manufacturing an electronic assembly according to an embodiment of the invention;
fig. 2A to 2C are schematic views illustrating a method for manufacturing an electronic device according to an embodiment of the invention.
Detailed Description
The present example provides a polyimide resin composition, a polyimide resin adhesive layer formed from the polyimide resin composition, a laminate, and a method for manufacturing an electronic component. Hereinafter, a detailed description will be given.
It is to be noted that, in this specification, the term "hydrocarbon group" means an organic group composed of only carbon and hydrogen, wherein the organic group is, for example, an alkyl group, an alkenyl group or an alkynyl group. The hydrocarbon group may be a linear hydrocarbon group, a branched hydrocarbon group, or a cyclic hydrocarbon group.
In this context, a "tetravalent organic group" is an organic group having four bonding sites, and the "tetravalent organic group" may form four chemical bonds via the four bonding sites.
In this context, a "divalent organic group" is an organic group having two bonding sites, and the "divalent organic group" can form two chemical bonds via the two bonding sites.
< polyimide resin composition >
A polyimide resin composition according to the present embodiment includes a polyimide resin. The monomers constituting the polyimide resin and the preparation method thereof will be described in detail below.
Monomers of polyimide resin
The polyimide resin is substantially obtained by polymerizing a diamine (A) and a tetracarboxylic dianhydride (B). Hereinafter, the above-mentioned various monomers will be described in detail.
Diamine (A)
The diamine (A) includes diamine (A-1) and diamine (A-2). The diamine (A) may further include a diamine (A-3). In addition, the diamine (A) may further include other diamines (A-4) without affecting the efficacy of the present example.
Diamine (A-1)
The diamine (A-1) is a diamine having a siloxane bond. Specifically, the diamine (A-1) is a compound represented by the following formula (I-1).
In the formula (I-1),
m1 and m2 are each an integer of 1 to 3, preferably both 1;
X 1 each is an alkyl group or an phenylene group having 1 to 5 carbon atoms, wherein when X is 1 When the alkyl group has 1 to 5 carbon atoms, -CH-is any one of the alkyl groups having 1 to 5 carbon atoms 2 -may be substituted by-NH-. X 1 Preferably an alkyl group having 1 to 5 carbon atoms or-CH 2 CH 2 NHCH 2 -。X 1 More preferably, it isAnd (3) a propylene group.
In one embodiment, the diamine (A-1) may be a compound represented by the following formula (I-1-1).
In the formula (I-1-1),
m1 and m2 are each an integer of 1 to 3, preferably both 1;
n1 and n2 are each an integer of 1 to 5, preferably 1 to 3, and more preferably 3.
Specific examples of the diamine (A-1) include, but are not limited to, 1,3-bis (3-aminopropyl) -1,1,3,3-tetramethyldisiloxane, 1,3-bis- (2-aminoethylaminomethyl) tetramethyldisiloxane (1,3-bis- (2-aminoethylaminomethyl) tetramethyldisiloxane), 1,3-bis- (4-aminophenyl) -1,1,3,3-tetramethyldisiloxane (1,3-bis (4-aminophenyl) -1,1,3,3-tetramethyldisiloxane), or a combination thereof, preferably 1,3-bis (3-aminopropyl) -1,1,3, 3-tetramethyldisiloxane.
Diamine (A-2)
The diamine (A-2) is a diamine having four benzene rings. Specifically, the diamine (A-2) is a compound represented by the following formula (I-2).
In the formula (I-2),
x2 is a hydrocarbon group having 1 to 10 carbon atoms, -O-, -S-, -SO 2 -、-NH-、-C(CF 3 ) 2 -or
Preferably an alkyl group having 1 to 5 carbon atoms or-C (CF) 3 ) 2 An alkyl group having 3 carbon atoms is more preferable. Specific example of the alkyl group having 3 carbon atoms is preferably-C (CH) 3 ) 2 -。
Specific examples of the diamine (A-2) include 2,2' -Bis [4- (4-aminophenoxy) phenyl ] propane (2,2' -Bis [4- (4-aminophenoxy) phenyl ] propane, BAPP), 2-Bis [4- (4-aminophenoxy) phenyl ] hexafluoropropane, Bis (4- (4-aminophenoxy) phenyl) sulfone, or a combination thereof, more preferably 2,2' -Bis [4- (4-aminophenoxy) phenyl ] propane.
The molar ratio of the diamine (A-1) to the diamine (A-2) ((A-1): (A-2)) may be 0.1: 0.2 to 0.6, preferably 0.4 to 0.6. When the molar ratio of the diamine (A-1) to the diamine (A-2) is in the above range, the polyimide resin composition has good chemical resistance and adhesion, and is suitable for the production of electronic parts. When the molar ratio of the diamine (A-1) to the diamine (A-2) ((A-1): (A-2)) is out of the above range, the polyimide resin composition cannot have both good chemical resistance and good adhesion, and thus cannot be suitably used for the production of electronic parts. Further, when the molar ratio of the diamine (A-1) to the diamine (A-2) ((A-1): (A-2)) is 0.1: when it is more than 0.6, the adhesiveness of the polyimide resin composition is poor. When the molar ratio of diamine (A-1) to diamine (A-2) ((A-1): (A-2)) was 0.1: when the content is less than 0.2, the polyimide resin composition has poor chemical resistance.
Diamine (A-3)
In one embodiment, the diamine (A) may further comprise a diamine (A-3). The diamine (A-3) is a diamine having a phenol structure. Specifically, the diamine (A-3) is a compound represented by the following formula (I-3).
In the formula (I-3), Y is-C (CH) 3 ) 2 -、-C(CF 3 ) 2 -、-CH 2 -, -O-, -S-, or-SO 2 -, preferably-C (CH) 3 ) 2 -or-C (CF) 3 ) 2 -, more preferably-C (CH) 3 ) 2 -。
Specific examples of the diamine (A-3) include 2,2-bis (3-amino-4-hydroxyphenyl) propane (2,2-bis (3-amino-4-hydroxyphenyl) propane, BAHPP), 2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane (2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane), 2-bis (3-amino-4-hydroxyphenyl) sulfone, or a combination thereof, preferably include 2,2-bis (3-amino-4-hydroxyphenyl) propane.
The molar ratio of diamine (A) to diamine (A-3) ((A): (A-3)) may be 1: greater than 0 to 4 or less, preferably 1: 2 to 4. When the molar ratio of the diamine (A) to the diamine (A-3) is in the above range, the polyimide resin composition has better resistance to chemical attack and adhesion.
Other diamines (A-4)
The diamine (A) may further include other diamines (A-4) without affecting the efficacy of this example. The other diamine (A-4) is not particularly limited and may be appropriately selected as required.
Specific examples of the other diamine (A-4) may include 3,4' -diaminodiphenyl ether, 3, 4-diaminodiphenyl ether, 4-diaminodiphenyl ether, 3, 4-diaminodiphenyl sulfone, 4-diaminodiphenyl sulfone, bis [4- (3-aminophenoxy) phenyl ] sulfone, bis (4-amino-3-carboxyphenyl) methane, or a combination thereof; preferably, 3,4' -diaminodiphenyl ether is included.
The molar ratio of diamine (A) to tetracarboxylic dianhydride (B) described later is 0.5 to 1.2: 1, preferably 0.9 to 1.1: 1.
tetracarboxylic dianhydride (B)
The tetracarboxylic dianhydride (B) is not particularly limited, and an appropriate tetracarboxylic dianhydride can be selected as required.
Specific examples of the tetracarboxylic dianhydride (B) may include 3,3',4,4' -diphenylether tetracarboxylic dianhydride (ODPA), Bicyclo [2.2.2] oct-7-ene-2,3,5,6-tetracarboxylic dianhydride (Bicyclo [2.2.2] oct-7-ene-2,3,5,6-tetracarboxylic dianhydride, BTA), 1,2,4, 5-cyclohexanetetracarboxylic dianhydride, 5- (2, 5-dioxotetrahydrofuran) -3-methyl-3-cyclohexene-1, 2-dicarbonic anhydride, 3,3',4,4' -benzophenonetetracarboxylic dianhydride, 2,3,3',4' -diphenylether tetracarboxylic dianhydride, 1,2,3, 4-cyclobutanetetracarboxylic dianhydride, pyromellitic dianhydride, Bis (3, 4-dicarboxyphenyl) ether dianhydride, bis (3, 4-dicarboxyphenyl) sulfide dianhydride, bis (3, 4-dicarboxyphenyl) sulfone dianhydride, bis (3, 4-dicarboxyphenyl) methane dianhydride, 2-bis (3, 4-dicarboxyphenyl) propane dianhydride, 2-bis (3, 4-dicarboxyphenyl) -1,1,1,3,3, 3-hexafluoropropane dianhydride, 1,2,3, 4-cyclopentanetetracarboxylic dianhydride, 1,2,4, 5-cyclohexanetetracarboxylic dianhydride, bicyclo [2.2.1] heptane-2, 3,5,6-tetracarboxylic dianhydride, bicyclo [2.2.2] oct-ene-2, 3,5,6-tetracarboxylic dianhydride, bicyclo [2.2.2] octane-2, 3,5,6-tetracarboxylic dianhydride or a combination thereof, preferably includes 3,3',4,4' -diphenyl ether tetracarboxylic dianhydride, bicyclo [2.2.2] oct-7-ene-2,3,5,6-tetracarboxylic dianhydride, or a combination thereof, more preferably 3,3',4,4' -diphenyl ether tetracarboxylic dianhydride.
Preparation of polyimide resin
The tetracarboxylic dianhydride and the diamine may be first polymerized to form the polyamic acid polymer. Then, dehydration ring-closure reaction is performed, so that the amic acid functional group in the polyamic acid polymer is converted into an imide functional group (i.e., imidized) through dehydration ring-closure reaction, and a polyimide resin including an imide functional group is obtained.
The polymerization and dehydration ring-closure reactions may be carried out in the presence of a solvent. The solvent may include polar solvents such as N-methylpyrrolidone, γ -butyrolactone, dimethylacetamide, methylformamide, diethylacetamide, 1, 3-dimethyl-2-imidazolidinone, N-methylcaprolactam, hexamethylphosphoric triamide, and the like. The above solvents may be used alone or in combination of plural kinds. In view of the solubility of the reactants, the solvent is preferably N-methylpyrrolidone. However, the present embodiment is not limited thereto, and other solvents may be selected as required. The total amount of the tetracarboxylic dianhydride, the diamine and the solvent used in the polymerization reaction is 100 wt%, and the content of the solvent used in the polymerization reaction may be 15 to 45 wt%, preferably 20 to 35 wt%, based on the synthetic polyimide resin.
The temperature of the polymerization reaction can be 50-80 ℃ and the time can be 3-6 hours.
The dehydration ring-closure reaction can be carried out using a high temperature dehydration ring-closure method or a chemical dehydration ring-closure method. The temperature of the high-temperature dehydration closed-loop method can be 250-350 ℃, and the time can be 3-6 hours. The chemical dehydration closed-loop method can add a dehydrating agent and a catalyst into a reaction solution, and react for 3-6 hours at the temperature of 160-180 ℃. Examples of the dehydrating agent include anhydrides such as acetic anhydride, propionic anhydride and trifluoroacetic anhydride, but the present invention is not limited thereto, and other dehydrating agents may be selected as required. The catalyst is, for example, a tertiary amine such as 1-ethylpiperidine, triethylamine, pyridine, lutidine, etc., but the present invention is not limited thereto, and other catalysts may be selected as required.
In addition, in another embodiment of the present invention, a blocking agent may be further added in the polymerization reaction of the tetracarboxylic dianhydride and the diamine in order to control the molecular weight of the polyimide resin. The blocking agent is not particularly limited and may be any known in the art to which the present invention pertains, including, but not limited to, 3-aminophenol (3-aminophenol), phthalic anhydride, maleic anhydride, nadic acid, cyclohexane dicarboxylic anhydride, 3-hydroxyphthalic anhydride, 3-carboxyphenol, 4-carboxyphenol, 3-carboxythiophenol, 4-carboxythiophenol, 1-hydroxy-7-carboxynaphthalene, 1-hydroxy-6-carboxynaphthalene, 1-hydroxy-5-carboxynaphthalene, 1-mercapto-7-carboxynaphthalene, 1-mercapto-6-carboxynaphthalene, 1-mercapto-5-carboxynaphthalene, 3-carboxybenzenesulfonic acid, 4-carboxybenzenesulfonic acid, or a combination thereof.
A polyimide resin according to the present embodiment, wherein the polyimide resin includes a structural unit represented by general formula (1).
In the formula (1), Ar 1 Is a tetravalent organic radical, Ar 2 Is a group represented by the following formula (1-1) or a group represented by the following formula (1-2).
Specifically, Ar 1 The tetravalent organic group may be derived from the tetracarboxylic dianhydride (B) described above. In one embodiment, Ar 1 The group may be a group represented by the following formula (1-a) or a group represented by the following formula (1-b), and a group represented by the following formula (1-a) is preferred.
Wherein the group represented by the formula (1-a) is derived from 3,3',4,4' -diphenyl ether tetracarboxylic dianhydride; and the group represented by the formula (1-b) may be derived from bicyclo [2.2.2] oct-7-ene-2,3,5,6-tetracarboxylic dianhydride.
In the formula (1-1),
m1 and m2 are each an integer of 1 to 3, preferably both 1;
x1 is independently an alkyl group having 1 to 5 carbon atoms or an phenylene group, wherein when X is 1 When the alkyl group has 1 to 5 carbon atoms, -CH-is any one of the alkyl groups having 1 to 5 carbon atoms 2 -may be substituted by-NH-. X 1 Preferably each alkyl group having 1 to 5 carbon atoms.
In one embodiment, Ar 2 May be a group represented by the following formula (1-1-a).
In the formula (1-1-a),
m1 and m2 are each an integer of 1 to 3, preferably both 1;
n1 and n2 are each an integer of 1 to 5, preferably 1 to 3, more preferably 3;
denotes a bonding site.
Specific examples of the formula (1-1) include, but are not limited to, a group represented by the following formula (1-1-1), a group represented by the following formula (1-1-2), and a group represented by the following formula (1-1-3), preferably a group represented by the following formula (1-1-1).
The group represented by the formula (1-1-1) may be derived from 1,3-bis (3-aminopropyl) -1,1,3, 3-tetramethyldisiloxane. The group represented by the formula (1-1-2) may be derived from 1,3-bis- (2-aminoethylaminomethyl) tetramethyldisilane. The group represented by the formula (1-1-3) may be derived from 1,3-bis- (4-aminophenyl) -1,1,3, 3-tetramethyldisilane (1,3-bis (4-aminophenyl) -1,1,3, 3-tetramethylisiloxane).
X 2 Is a hydrocarbon group having 1 to 10 carbon atoms, -O-, -S-, -SO 2 -、-NH-、-C(CH 3 ) 2 -、-C(CF 3 ) 2 -or, preferably, alkyl having 1 to 5 carbon atoms or-C (CF) 3 ) 2 -more preferably an alkyl group having 3 carbon atoms;
denotes a bonding site.
Specific example of the alkyl group having 3 carbon atoms is preferably-C (CH) 3 ) 2 -。
The formula (1-2) may be a group represented by any one of the following formulae (1-2-1) to (1-2-8), and preferably a group represented by the formula (1-2-6).
In one embodiment, the molar ratio of the group represented by formula (1-1) to the group represented by formula (1-2) is 0.1: 0.2 to 0.6, preferably 0.4 to 0.6. When the molar ratio of the group represented by the formula (1-1) to the group represented by the formula (1-2) is in the above range, the polyimide resin composition has good chemical resistance and adhesion, and is suitable for the production of electronic parts. When the molar ratio of the group represented by the formula (1-1) to the group represented by the formula (1-2) is out of the above range, the polyimide resin composition cannot have both good chemical resistance and good adhesion, and thus cannot be suitably used for the production of electronic parts. Further, when the molar ratio of the group represented by the formula (1-1) to the group represented by the formula (1-2) is 0.1: when it is more than 0.6, the adhesiveness of the polyimide resin composition is poor. When the group represented by the formula (1-1) and the group represented by the formula (1-2) are 0.1: when the content is less than 0.2, the polyimide resin composition has poor chemical resistance.
In one embodiment, the polyimide resin may further include a structural unit represented by general formula (2).
In the formula (2), Ar 1 Is a tetravalent organic radical, Ar 3 Is a group represented by the following formula (2-1).
Ar in the formula (2) 1 Description of (2) and Ar in the formula (1) 1 The descriptions are the same, and are not repeated herein.
In the formula (2-1),
y is-C (CH) 3 ) 2 -、-C(CF 3 ) 2 -、-CH 2 -, -O-, -S-, or-SO 2 -, preferably-C (CH) 3 ) 2 -or-C (CF) 3 ) 2 -, more preferably-C (CH) 3 ) 2 -；
Denotes a bonding site.
The molar ratio of the group represented by the formula (1-1) to the group represented by the formula (2-1) is 1: greater than 0 to 4, preferably 1: 2 to 4. When the molar ratio of the group represented by the formula (1-1) to the group represented by the formula (2-1) is in the above range, the polyimide resin composition can have better resistance to chemical attack and adhesion.
The formula (2-1) is preferably a group represented by the following formula (2-1-1) or formula (2-1-2), more preferably a group represented by the formula (2-1-1). Wherein the group represented by the formula (2-1-1) is derived from 2,2-bis (3-amino-4-hydroxyphenyl) propane; and the group represented by the formula (2-1-2) may be derived from 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane.
In one embodiment, the polyimide resin may further include a structural unit represented by general formula (3).
In the formula (3), the reaction mixture is,
Ar 1 is a tetravalent organic radical;
Ar 4 is a group represented by the following formula (3-1), wherein the group represented by the formula (3-1) can be derived from 3,4' -diaminodiphenyl ether.
Ar in formula (3) 1 Description of (1) and Ar in the formula (1) 1 The descriptions are the same, and are not repeated herein.
In the formula (3-1), a indicates a bonding site.
In one embodiment, Ar in the above formulas (1) to (3) 1 Is a group represented by the following formula (1-a),
in the formula (1-a), the symbol represents a bonding site.
The weight average molecular weight of the polyimide resin is 5,000 to 50,000, preferably 10,000 to 40,000, and more preferably 25,000 to 35,000.
Solvent (C)
In one embodiment, the polyimide resin composition may further include a solvent (C). The solvent (C) is not particularly limited as long as it can dissolve the polyimide resin and other components in the polyimide resin composition and does not react with the other components of the polyimide resin composition. The solvent (C) is preferably a solvent used for synthesizing the polyimide resin.
Specific examples of the solvent (C) include, but are not limited to, N-methylpyrrolidone, γ -butyrolactone, γ -butyrolactam, 4-hydroxy-4-methyl-2-pentanone, ethylene glycol monomethyl ether, butyl lactate, butyl acetate, methyl methoxypropionate, ethyl ethoxypropionate, ethylene glycol methyl ether, ethylene glycol ethyl ether, ethylene glycol N-propyl ether, ethylene glycol isopropyl ether, ethylene glycol N-butyl ether (ethylene glycol N-butyl ether), ethylene glycol dimethyl ether, ethylene glycol ethyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate or N, N-dimethylformamide or N, N-dimethylacetamide (N, n-dimethylacetamide), or combinations of the foregoing solvents.
The solvent (C) is used in an amount of 800 to 4000 parts by weight, preferably 900 to 3500 parts by weight, and more preferably 1000 to 3000 parts by weight, based on 100 parts by weight of the polyimide resin (a).
Additive (D)
In one embodiment, the polyimide resin composition may further include an additive (D) in addition to the polyimide resin, without affecting the efficacy of the embodiment. The additive is not particularly limited and may be appropriately selected as required. Specifically, the additives may include inorganic particles, antioxidants, aging inhibitors, or combinations thereof.
< method for producing electronic component >
FIG. 1 is a flow chart of a method of manufacturing an electronic assembly, particularly for use in manufacturing Micro light emitting diodes (Micro LEDs), according to one embodiment of the present invention. More specifically, the method for manufacturing the electronic device can realize Mass Transfer (Mass Transfer) when used for manufacturing the Micro LED, and achieve the effect of transferring the Mass Micro LED to a specific substrate at a time. In this embodiment, the method of manufacturing an electronic component includes: step S1: providing a laminated body comprising a polyimide resin adhesive layer, a first substrate, a release layer, a second substrate and an electronic assembly; step S2: removing the release layer and the second substrate from the laminate to expose the second surface of the polyimide resin adhesive layer and a portion of the electronic component; and step S3: the polyimide resin adhesive layer and the first substrate are removed.
Fig. 2A to 2C are schematic views illustrating a method for manufacturing an electronic device according to an embodiment of the invention.
First, please refer to fig. 1 and fig. 2A simultaneously. In step S1, the multilayer body 10 is provided. The laminate 10 includes a polyimide resin adhesive layer 12, a first substrate 14, a release layer 16, a second substrate 18, and an electronic component 20. The polyimide resin adhesive layer 12 has a first surface 12a and a second surface 12b opposite to each other. The release layer 16 has a third surface 16a and a fourth surface 16b opposite to each other. The first substrate 14 is attached to the first surface 12a of the polyimide resin adhesive layer 12. The third surface 16a of the release layer 16 is attached to the second surface 12b of the polyimide resin adhesive layer 12. The second substrate 18 is attached to the fourth surface 16b of the release layer 16. The electronic component 20 is embedded in the polyimide resin adhesive layer 12, and the electronic component 20 is connected with the release layer 16.
The polyimide resin adhesive layer 12 is formed of the polyimide resin composition described above.
The first substrate 14 is a hard substrate such as a glass substrate, a quartz substrate, or a sapphire substrate.
The release layer 16 is a layer that can be separated from the polyimide resin adhesive layer 12 by a mechanical peeling method, such as a metal layer or a polymer layer. The metal layer may be a copper layer or an aluminum layer, and the polymer layer may be made of polypropylene oxide (PPO), polyethylene terephthalate (PET), epoxy resin, acrylic or fluorine resin (fluorine resin), or other high temperature resistant polymers.
The second substrate 18 is, for example, a glass substrate, a quartz substrate, or a sapphire substrate, but not limited thereto.
The electronic component 20 is, for example, a light emitting diode 20. As shown in fig. 2A, the light emitting diode 20 includes an epitaxial layer 22 and two electrodes 24. Two electrodes 24 are disposed on the epitaxial layer 22. In the embodiment, the two electrodes 24 may be disposed on the same side of the epitaxial layer 22, but the invention is not limited thereto, and the two electrodes 24 may also be disposed on two opposite sides of the epitaxial layer 22, respectively. In addition, the light emitting diode 20 is embedded in the polyimide resin adhesive layer 12, and the exposed portion of the light emitting diode 20 can be connected to the release layer 16 through the polyimide resin adhesive layer. In one embodiment, the led 20 is connected to the release layer 16 through the epitaxial layer 22. The epitaxial layer 22 may include a first type semiconductor layer (not shown), a second type semiconductor layer (not shown) and a light emitting layer (not shown), wherein the light emitting layer is located between the first type semiconductor layer and the second type semiconductor layer. The first type semiconductor layer and the second type semiconductor layer are electrically connected to the two electrodes 24, respectively. The first type semiconductor layer is, for example, an N-type semiconductor layer, and the second type semiconductor layer is, for example, a P-type semiconductor layer, but not limited thereto. The light-emitting layer is not particularly limited, and an appropriate material may be selected as required. The two electrodes 24 are, for example, a conductive metal such as gold, silver, copper, etc., but not limited thereto. In one embodiment, the led 20 may further include a transparent conductive layer (not shown), such as indium tin oxide, aluminum-doped zinc oxide, or indium zinc oxide.
The method of laminating the laminate 10 is not particularly limited, and for example, the polyimide resin composition is coated on the first substrate 14 to form the polyimide resin adhesive layer 12; embedding the electronic component 20 in the polyimide resin adhesive layer 12 and exposing a portion of the electronic component 20; and sequentially laminating the release layer 16 and the second substrate 18 on the second surface 12b of the polyimide resin adhesive layer 12 and the exposed portion of the electronic component 20.
Next, referring to fig. 1 and fig. 2B, in step S2, the release layer 16 and the second substrate 18 are removed from the laminate 10 to expose the second surface 12B of the polyimide resin adhesive layer 12 and portions of the electronic components 20. The method for removing the release layer 16 and the second substrate 18 is not particularly limited, and for example, the release layer 16 and the second substrate 18 are mechanically peeled off from the second surface of the polyimide resin adhesive layer 12.
Next, please refer to fig. 1 and fig. 2C simultaneously. In step S3, the polyimide resin adhesive layer 12 and the first substrate 14 are removed. The method for removing the polyimide resin adhesive layer 12 and the first substrate 14 is not particularly limited, and may be, for example, the mechanical peeling method, the solvent peeling method, or a combination thereof. The conditions of the mechanical peeling method are not particularly limited, and may be performed at room temperature, for example. The first organic solvent used in the solvent stripping method is not particularly limited as long as the polyimide resin adhesive layer 12 can be dissolved and the electronic component 20 is not damaged. In addition, in other embodiments of the present invention, an organic structural layer (not shown) may also be formed on the electronic component 20.
In the method for manufacturing an electronic device according to an embodiment, after step S1, a pressing step may be further included, so that the electronic device 20 can be reliably embedded in the polyimide resin adhesive layer 12 and fixed between the first substrate 14 and the second substrate 18. The pressurizing step is not particularly limited, and an appropriate pressurizing method may be selected as required.
In the method for manufacturing an electronic device according to an embodiment, after the step S3, a step of removing residual glue on the first substrate 14 and the second substrate 18 with a second organic solvent or an alkaline solution may be further included. The second organic solvent is not particularly limited as long as the polyimide resin adhesive layer 12 can be dissolved and the first substrate 14 and the second substrate 18 are not damaged. Here, the second organic solvent is preferably the same as the first organic solvent.
Hereinafter, the present invention will be described in detail with reference to experimental examples. The following experimental examples are provided for describing the present invention, and the scope of the present invention includes the scope described in the following claims and substitutes and modifications thereof, and is not limited to the scope of the experiments.
Experimental examples and comparative examples of polyimide resin
The following will describe experimental examples 1 and 2 and comparative examples 1 to 4 of polyimide resin compositions:
experimental example 1
8.981 g (0.036 mol) of 1,3-bis (3-aminopropyl) -1,1,3,3-tetramethyldisiloxane, 59.340 g (0.145 mol) of 2,2' -bis [4- (4-aminophenoxy) phenyl ] propane, 37.340 g (0.145 mol) of 2,2-bis (3-amino-4-hydroxyphenyl) propane, 7.236 g (0.036 mol) of 3, 4-diaminodiphenyl ether and 112.103 g (0.36 mol) of 3,3',4,4' -diphenylether tetracarboxylic dianhydride were charged into a 1000 ml three-necked flask which was purged with nitrogen and equipped with a mechanical stirrer, and 673.200 g of N-methylpyrrolidone as a solvent were then added and stirred at 70 ℃ for 4 hours. Then, 1.800 g of 1-Ethylpiperidine (1-Ethylpiperidine) was added as a catalyst, and the temperature was raised to 180 ℃ and stirred for 4 hours. After cooling, the polyimide resin composition solution of experimental example 1 was obtained.
Experimental example 2 and comparative examples 1 and 3
The polyimide resin compositions of experimental example 2 and comparative examples 1 and 3 were prepared in the same procedure as in experimental example 1, and they were different in that: the kinds of components and the amounts thereof used in the polyimide resin composition were changed (as shown in table 1). The obtained polyimide resin composition was formed into a film and evaluated in the following evaluation manners, and the results thereof are shown in table 1.
Comparative example 2
17.101 g (0.069 mol) of 1,3-bis (3-aminopropyl) -1,1,3,3-tetramethyldisiloxane, 88.878 g (0.344 mol) of 2,2-bis (3-amino-4-hydroxyphenyl) propane, 48.226 g (0.241 mol) of 3, 4-diaminodiphenyl ether and 170.785 g (0.688 mol) of bicyclo [2.2.2] oct-7-ene-2,3,5,6-tetracarboxylic dianhydride were added to a 1000 ml three-neck round-bottomed flask which was purged with nitrogen and equipped with a mechanical stirrer, and 647.20 g of γ -butyrolactone was then added as a solvent and stirred at 70 ℃ for 4 hours. Then, 7.509 g (0.069 mol) of blocking agent 3-aminophenol (3-aminophenol) was added thereto, and the mixture was stirred at 70 ℃ for another 4 hours. Then, 2.660 g of 1-ethylpiperidine was further added as a catalyst, and the temperature was raised to 180 ℃ and stirred for 4 hours. After cooling, the polyimide resin composition solution of comparative example 2 was obtained.
Comparative example 4
The polyimide resin composition of comparative example 4 was prepared in the same procedure as in comparative example 2, and was different therefrom in that: the kinds of components and the amounts of the components used in the polyimide resin composition were changed (as shown in table 1). The film of the polyimide resin composition thus obtained was evaluated in the following evaluation methods, and the results are shown in Table 1.
The sources of the ingredients/compounds in table 1 are as in table 2 below.
[ Table 2]
< evaluation mode >
I. Resistance to chemical attack
The polyimide resin composition solutions prepared in the experimental examples and comparative examples were applied onto a first glass substrate by spin coating (spin coater model Clean Track MK-8, manufactured by Tokyo Electron Limited, TEL, at a rotation speed of 1200 rpm). Then, soft baking was performed at a temperature of 110 ℃ for 300 seconds to form a polyimide resin composition film having a thickness of 1.5. mu.m.
The polyimide resin composition film was immersed in tetramethylammonium hydroxide (TMAH) or Propylene Glycol Monomethyl Ether Acetate (PGMEA) at a concentration of 2.38 wt% for 5 minutes, respectively, and then the change of the polyimide resin composition film was observed.
The evaluation criteria for the resistance were as follows:
o: the polyimide resin composition film was not cracked and dissolved.
Gamma rays: the polyimide resin composition film cracks or dissolves.
Adhesive Property II
The polyimide resin composition solutions prepared in the experimental examples and comparative examples were applied onto a first glass substrate by spin coating (spin coater model Clean Track MK-8, manufactured by Tokyo Electron Limited, TEL, at a rotation speed of 1200 rpm). Then, soft baking was performed at a temperature of 110 ℃ for 300 seconds to form a polyimide resin composition film having a thickness of 1.5. mu.m. Then, a second glass substrate is covered on the polyimide resin composition film so that the polyimide resin composition film is sandwiched between the first glass substrate and the second glass substrate. Then, 500 kg of pressure was applied to the first glass substrate and the second glass substrate. Finally, the mixture was placed in an oven at 170 ℃ for 15 minutes. Whether or not the polyimide resin composition film and the glass substrate were bonded was visually observed.
The evaluation criteria for adhesion are as follows:
o: the polyimide resin composition film was bonded to a glass substrate.
Gamma rays: the polyimide resin composition film and the glass substrate cannot be bonded to each other.
< evaluation results >
As can be seen from table 1, when the molar ratio of the diamine having a siloxane bond to the diamine having four benzene rings is 0.1: when the amount is in the range of 0.2 to 0.6 (examples 1 and 2), the polyimide resin composition has good chemical resistance and adhesion.
In contrast, when the molar ratio of the diamine having a siloxane bond to the diamine having four benzene rings is not 0.1: when the amount is in the range of 0.2 to 0.6 (comparative examples 1 to 4), the polyimide resin composition cannot have both good chemical resistance and good adhesion. Further, when the molar ratio of the diamine having four benzene rings is 0.1: when the amount is more than 0.6 (comparative example 1), the adhesiveness of the polyimide resin composition is poor. When the molar ratio of diamine having four benzene rings is 0.1: when the content is less than 0.2 (comparative examples 2 to 4), the polyimide resin composition is poor in chemical resistance.
In summary, the present invention provides a polyimide resin composition comprising a polyimide resin composition prepared by mixing a diamine having a siloxane bond and a diamine having four benzene rings in a molar ratio of 0.1: 0.2 to 0.6 diamine, and the polyimide resin composition has good chemical resistance and adhesion, and is therefore suitable for the production of electronic components. Also disclosed are a polyimide resin adhesive layer formed from such a polyimide resin composition, a laminate comprising such a polyimide resin adhesive layer, and a method for producing an electronic component.
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention.
Claims (12)
1. A polyimide resin composition comprising a polyimide resin obtained by substantially polymerizing a diamine A and a tetracarboxylic dianhydride B,
said diamine A comprises diamine A-1 represented by the following formula (I-1) and diamine A-2 represented by the following formula (I-2), wherein said diamine A-1 is characterized in that the molar ratio of said diamine A-2 (A-1: A-2) is 0.1: 0.2 to 0.6 of a surfactant,
in the formula (I-1), m1 and m2 are each an integer of 1 to 3, X 1 Each is an alkyl group or a phenylene group having 1 to 5 carbon atoms, wherein when X 1 When the alkyl group has 1 to 5 carbon atoms, -CH-is any one of the alkyl groups having 1 to 5 carbon atoms 2 -may be substituted by-NH-,
in the formula (I-2), X 2 Is a hydrocarbon group having 1 to 10 carbon atoms, -O-, -S-, -SO 2 -、-NH-、-C(CF 3 ) 2 -or
2. The polyimide resin composition according to claim 1, wherein the diamine a further comprises a diamine a-3 represented by the following formula (I-3), and the molar ratio (a: a-3) of the diamine a to the diamine a-3 is 1: greater than 0 to not more than 4,
in the formula (I-3), Y is-C (CH) 3 ) 2 -、-C(CF 3 ) 2 -、-CH 2 -, -O-, -S-, or-SO 2 -。
3. The polyimide resin composition according to claim 1, wherein the diamine a further comprises 3,4' -diaminodiphenyl ether.
4. The polyimide resin composition according to claim 1, wherein the tetracarboxylic dianhydride B comprises 3,3,4,4' -diphenyl ether tetracarboxylic dianhydride.
5. A polyimide resin composition comprising a polyimide resin comprising a structural unit represented by the general formula (1),
in the formula (1), Ar 1 Is a tetravalent organic radical, Ar 2 Is a group represented by the following formula (1-1) or a group represented by the following formula (1-2), wherein the molar ratio of the group represented by the formula (1-1) to the group represented by the formula (1-2) is 0.1: 0.2 to 0.6 of a total of,
in the formula (1-1), m1 and m2 are each an integer of 1 to 3, X 1 Each is an alkyl group or an phenylene group having 1 to 5 carbon atoms, wherein when X is 1 When the alkyl group has 1 to 5 carbon atoms, -CH-is any one of the alkyl groups having 1 to 5 carbon atoms 2 -may be substituted by-NH-representing a bonding site,
in the formula (1-2), X 2 Is a hydrocarbon group having 1 to 10 carbon atoms, -O-, -S-, -SO 2 -、-NH-、-C(CF 3 ) 2 -or
Denotes a bonding position.
6. The polyimide resin composition according to claim 5, wherein the polyimide resin further comprises a structural unit represented by the general formula (2),
in the formula (2), Ar 1 Is a tetravalent organic radical, Ar 3 Is a group represented by the following formula (2-1), wherein the molar ratio of the group represented by the formula (1-1) to the group represented by the formula (2-1) is 1: greater than 0 to not more than 4,
in the formula (2-1), Y is-C (CH) 3 ) 2 -、-C(CF 3 ) 2 -、-CH 2 -, -O-, -S-, or-SO 2 -.
7. The polyimide resin composition according to claim 5, wherein the polyimide resin further comprises a structural unit represented by the general formula (3),
in the formula (3), Ar 1 Is a tetravalent organic radical, Ar 4 Is a group represented by the following formula (3-1),
in the formula (3-1), the symbol represents a bonding site.
8. The polyimide resin composition according to any one of claims 5 to 7, wherein Ar in the formulae (1) to (3) 1 Is a group represented by the following formula (1-a),
in the formula (1-a), the symbol represents a bonding site.
9. A polyimide resin adhesive layer formed of the polyimide resin composition according to any one of claims 1 to 8.
10. A laminate body, comprising:
the polyimide resin adhesive layer of claim 9, having a first surface and a second surface opposite to each other;
a first substrate attached to the first surface of the polyimide resin adhesive layer;
the release layer is provided with a third surface and a fourth surface which are opposite to each other, and the third surface of the release layer is attached to the second surface of the polyimide resin adhesion layer;
the second substrate is attached to the fourth surface of the release layer; and
and the electronic component is embedded in the polyimide resin adhesion layer and is connected with the release layer.
11. A method of manufacturing an electronic assembly, comprising:
providing a laminate according to claim 10;
removing the release layer and the second substrate from the laminate to expose the second surface of the polyimide resin adhesive layer and a portion of the electronic component; and
and removing the polyimide resin adhesive layer and the first substrate.
12. The method of manufacturing an electronic component according to claim 11, wherein the electronic component is a light emitting diode.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110217082.5A CN114957660A (en) | 2021-02-26 | 2021-02-26 | Polyimide resin composition, polyimide resin adhesive layer, laminate, and method for producing electronic component |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110217082.5A CN114957660A (en) | 2021-02-26 | 2021-02-26 | Polyimide resin composition, polyimide resin adhesive layer, laminate, and method for producing electronic component |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114957660A true CN114957660A (en) | 2022-08-30 |
Family
ID=82973406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110217082.5A Pending CN114957660A (en) | 2021-02-26 | 2021-02-26 | Polyimide resin composition, polyimide resin adhesive layer, laminate, and method for producing electronic component |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114957660A (en) |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09286859A (en) * | 1996-04-19 | 1997-11-04 | Sumitomo Bakelite Co Ltd | Polyimide resin and production of film adhesive therefrom |
| JPH11335652A (en) * | 1998-05-22 | 1999-12-07 | Sumitomo Bakelite Co Ltd | Film adhesive |
| JP2007056167A (en) * | 2005-08-25 | 2007-03-08 | Hitachi Chem Co Ltd | Adhesive film and semiconductor apparatus using the same |
| JP2008091478A (en) * | 2006-09-29 | 2008-04-17 | Nippon Steel Chem Co Ltd | Manufacturing method for flexible board |
| JP2011063678A (en) * | 2009-09-16 | 2011-03-31 | Toray Ind Inc | Adhesive composition for semiconductor and semiconductor device using the composition |
| CN103739842A (en) * | 2013-12-20 | 2014-04-23 | 深圳瑞华泰薄膜科技有限公司 | Thermoplastic polyimide and method for preparing flexible copper-clad plate from thermoplastic polyimide |
| KR20150027599A (en) * | 2013-09-04 | 2015-03-12 | 주식회사 두산 | Polyimide-base poymer, polyamic acid, and flexible metal-clad laminate and printed circuit board using the polymer or the polyamic acid |
| CN105001421A (en) * | 2015-07-03 | 2015-10-28 | 中科院广州化学有限公司南雄材料生产基地 | Preparation of polyimide solid powder containing phenolic hydroxyl group and application thereof |
| TW201612016A (en) * | 2014-09-18 | 2016-04-01 | Mortech Corp | Polyimide metal laminate and a method of fabricating the same |
| CN106029744A (en) * | 2014-02-26 | 2016-10-12 | 东丽株式会社 | Polyimide resin, resin composition using same, and laminated film |
| CN112029098A (en) * | 2020-08-28 | 2020-12-04 | 中国科学院深圳先进技术研究院 | Polyimide composite material and preparation method and application thereof |
-
2021
- 2021-02-26 CN CN202110217082.5A patent/CN114957660A/en active Pending
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09286859A (en) * | 1996-04-19 | 1997-11-04 | Sumitomo Bakelite Co Ltd | Polyimide resin and production of film adhesive therefrom |
| JPH11335652A (en) * | 1998-05-22 | 1999-12-07 | Sumitomo Bakelite Co Ltd | Film adhesive |
| JP2007056167A (en) * | 2005-08-25 | 2007-03-08 | Hitachi Chem Co Ltd | Adhesive film and semiconductor apparatus using the same |
| JP2008091478A (en) * | 2006-09-29 | 2008-04-17 | Nippon Steel Chem Co Ltd | Manufacturing method for flexible board |
| JP2011063678A (en) * | 2009-09-16 | 2011-03-31 | Toray Ind Inc | Adhesive composition for semiconductor and semiconductor device using the composition |
| KR20150027599A (en) * | 2013-09-04 | 2015-03-12 | 주식회사 두산 | Polyimide-base poymer, polyamic acid, and flexible metal-clad laminate and printed circuit board using the polymer or the polyamic acid |
| CN103739842A (en) * | 2013-12-20 | 2014-04-23 | 深圳瑞华泰薄膜科技有限公司 | Thermoplastic polyimide and method for preparing flexible copper-clad plate from thermoplastic polyimide |
| CN106029744A (en) * | 2014-02-26 | 2016-10-12 | 东丽株式会社 | Polyimide resin, resin composition using same, and laminated film |
| TW201612016A (en) * | 2014-09-18 | 2016-04-01 | Mortech Corp | Polyimide metal laminate and a method of fabricating the same |
| CN105001421A (en) * | 2015-07-03 | 2015-10-28 | 中科院广州化学有限公司南雄材料生产基地 | Preparation of polyimide solid powder containing phenolic hydroxyl group and application thereof |
| CN112029098A (en) * | 2020-08-28 | 2020-12-04 | 中国科学院深圳先进技术研究院 | Polyimide composite material and preparation method and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5240363B2 (en) | Photosensitive resin composition, photosensitive resin composition film, and semiconductor device using the same | |
| KR102260081B1 (en) | Adhesive for temporary bonding, adhesive layer, method for manufacturing wafer work piece and semiconductor device using same, polyimide copolymer, polyimide mixed resin, and resin composition | |
| US20040010062A1 (en) | Polyimide copolymer and methods for preparing the same | |
| CN108603028B (en) | Resin composition, resin layer, temporary adhesive, laminated film, wafer processed body, and application thereof | |
| CN106916306B (en) | Resin composition, and insulating substrate and circuit board comprising same | |
| JP2011514266A (en) | High adhesion polyimide copper clad laminate and method for producing the same | |
| JPWO2006132165A1 (en) | Adhesive composition for semiconductor, semiconductor device using the same, and method for manufacturing semiconductor device | |
| CN108138013A (en) | Temporary adhesion laminate film uses the substrate processome of temporary adhesion laminate film and the manufacturing method of multilayer board processome and the manufacturing method using their semiconductor devices | |
| JPH04262593A (en) | Multilayer interconnection structure and multilayers laminating method therefor | |
| KR101924829B1 (en) | Polyamide acid and resin composition containing same | |
| JP2020072198A (en) | Metal-clad laminate, circuit board, multilayer circuit board, and manufacturing method thereof | |
| JP5139986B2 (en) | POLYIMIDE RESIN COMPOSITION, PROCESS FOR PRODUCING THE SAME, AND METAL LAMINATE | |
| TW200825123A (en) | Flexible light guide and laminate board for optical/electrical composite wiring board | |
| JP2013080876A (en) | Substrate manufacturing method and substrate | |
| KR100627404B1 (en) | Flexible metal laminate and heat-resistant adhesive composition | |
| KR20150016329A (en) | Adhesive sheet for production of semiconductor device having bump electrodes and production method for semiconductor device | |
| JP5103870B2 (en) | Adhesive composition for semiconductor, semiconductor device using the same, and method for manufacturing semiconductor device | |
| JP2003213130A (en) | Polyimide resin composition and fire-resistant adhesive | |
| CN114957660A (en) | Polyimide resin composition, polyimide resin adhesive layer, laminate, and method for producing electronic component | |
| JP2001262116A (en) | Adhesive polyimide resin for electronic component | |
| KR20220124824A (en) | Polyimide, polyimide solution composition, polyimide film, and substrate | |
| TWI739715B (en) | Polyimide resin composition, polyimide resin adhesive layer, laminate, and manufacturing method of electronic component | |
| JP2019131704A (en) | Resin composition for temporary protective film, and manufacturing method of semiconductor electronic component using the same | |
| TW202233416A (en) | Polyimide resin composition, adhesive composition, film adhesive material, adhesive sheet, copper foil with resin, copper clad laminate, printed wiring board and polyimide film a polyimide resin layer with low dielectric constant, low dielectric loss tangent and excellent solder heat resistance | |
| KR101999926B1 (en) | Polyamic acid Composition for Preparing Polyimide Resin with Superior Adhesive Strength and Polyimide Resin Prepared Therefrom |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |