JP5922035B2 - ポリアミック酸樹脂組成物及びその製造方法、並びにこれを用いたポリイミド金属積層体 - Google Patents
ポリアミック酸樹脂組成物及びその製造方法、並びにこれを用いたポリイミド金属積層体 Download PDFInfo
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- JP5922035B2 JP5922035B2 JP2012545850A JP2012545850A JP5922035B2 JP 5922035 B2 JP5922035 B2 JP 5922035B2 JP 2012545850 A JP2012545850 A JP 2012545850A JP 2012545850 A JP2012545850 A JP 2012545850A JP 5922035 B2 JP5922035 B2 JP 5922035B2
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- polyimide
- metal laminate
- polyamic acid
- acid resin
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- 239000002184 metal Substances 0.000 title claims description 60
- 229910052751 metal Inorganic materials 0.000 title claims description 60
- 239000004642 Polyimide Substances 0.000 title claims description 57
- 229920001721 polyimide Polymers 0.000 title claims description 57
- 229920005575 poly(amic acid) Polymers 0.000 title claims description 24
- 239000011342 resin composition Substances 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title description 12
- 239000010410 layer Substances 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 19
- 239000004593 Epoxy Substances 0.000 claims description 18
- 239000011888 foil Substances 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 10
- 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 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 150000004984 aromatic diamines Chemical class 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims description 3
- NBNOYIPKKPUGKE-UHFFFAOYSA-N 1h-imidazole;triazine Chemical compound C1=CNC=N1.C1=CN=NN=C1 NBNOYIPKKPUGKE-UHFFFAOYSA-N 0.000 claims description 3
- 239000012790 adhesive layer Substances 0.000 claims description 3
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000001723 curing Methods 0.000 description 8
- 230000000704 physical effect Effects 0.000 description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- -1 3-aminophenoxy Chemical group 0.000 description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical group NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000011229 interlayer Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 239000011889 copper foil Substances 0.000 description 2
- 230000032798 delamination Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 description 1
- DKKYOQYISDAQER-UHFFFAOYSA-N 3-[3-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=C(OC=3C=C(N)C=CC=3)C=CC=2)=C1 DKKYOQYISDAQER-UHFFFAOYSA-N 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- QYIMZXITLDTULQ-UHFFFAOYSA-N 4-(4-amino-2-methylphenyl)-3-methylaniline Chemical group CC1=CC(N)=CC=C1C1=CC=C(N)C=C1C QYIMZXITLDTULQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZNVDOKOOMPHOSP-UHFFFAOYSA-N 4-amino-n-(4-amino-2-methoxyphenyl)benzamide Chemical compound COC1=CC(N)=CC=C1NC(=O)C1=CC=C(N)C=C1 ZNVDOKOOMPHOSP-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 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
- 239000004305 biphenyl Substances 0.000 description 1
- TUQQUUXMCKXGDI-UHFFFAOYSA-N bis(3-aminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(N)C=CC=2)=C1 TUQQUUXMCKXGDI-UHFFFAOYSA-N 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
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
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
- C08G73/1071—Wholly aromatic 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of 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 C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- 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
-
- 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
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
- C08G73/105—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the diamino moiety
-
- 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
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
- Y10T428/31681—Next to polyester, polyamide or polyimide [e.g., alkyd, glue, or nylon, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Laminated Bodies (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Description
[化学式1]
(前記化学式1中、X1、X2はそれぞれ独立して、−CmH2m−CH3で置換または非置換され、Y-1またはY2-のうち何れか一つ以上は、
または
(p、qは1〜5の整数)から選択され、m、nは1〜5の整数、rは1〜10の自然数である。)
[化学式1]
(前記化学式1中、X1、X2はそれぞれ独立して、−CmH2m−CH3で置換または非置換され、Y1またはY2のうち何れか一つ以上は、
または
(p、qは1〜5の整数)から選択され、m、nは1〜5の整数、rは1〜10の自然数である。)
[化学式2]
(前記化学式2中、iは0〜10の自然数である。)
[化学式3]
(前記化学式3中、jは0〜10の自然数である。)
[化学式4]
(前記化学式4中、kは0〜10の自然数である。)
ポリアミック酸樹脂組成物は、4,4´−ジアミノジフェニルエーテル(ODA)、パラフェニレンジアミン(PDA)、3,3´,4,4´−ビフェニルテトラカルボン酸ジアンヒドリド(BPDA)、N、N−ジメチルアセトアミド(DMAc)で構成され、エポキシ化合物であるYDCN500−90P(国都化学製)、YDPN−638(国都化学製)、N865(国都化学製)を使用する。下記表1はポリアミック酸樹脂組成物の組成比を示す。
前記表1の組成物Eを12μmの電解(Electro deposited;ED、以下「ED」とする)銅箔にコーティングして第一の層を形成する。ポリイミドの厚さは5μmになるようにする。このようにコーティングして形成された第一の層は140℃にて10分間乾燥する。次に、組成物Bをポリイミドの厚さが10、20、30、40μmになるように前記第一の層にコーティングして第二の層を形成した後、140℃にて10分間乾燥する。その後、ロールツーロール硬化装置で分当たり40℃の昇温速度で常温から380℃まで昇温しながら硬化し、ポリイミドフレキシブル金属積層体を製造した。以下、下記の物性を評価し、その結果を表2に示した。
ブリスタリング数:10cm×10cmで発生するブリスタリング数の5回の平均値を記録する。ブリスタリングのない場合には「なし」と記録し、全面にブリスタリングが発生して測定が不可能な場合には「層間完全分離」と記録する。
前記表1の組成物Bの代わりに組成物Cを使用することを除き実施例1と同一の方法でポリイミドフレキシブル金属積層体を製造した。その後、下記の物性を評価し、その結果を表2に示した。
前記表1の組成物Bの代わりに組成物Dを使用することを除き実施例1と同一の方法でポリイミドフレキシブル金属積層体を製造した。その後、下記の物性を評価し、その結果を表2に示した。
前記表1の組成物Fを12μmのED銅箔にコーティングして第一の層を形成する。ポリイミドの厚さは5μmになるようにする。このようにコーティングして形成された第一の層は140℃にて10分間乾燥する。次に、組成物Aをポリイミドの厚さが10、20、30、40μmになるように前記第一の層にコーティングして第二の層を形成した後、140℃にて10分間乾燥する。その後、ロールツーロール硬化装置で分当たり2℃の昇温速度で常温から380℃まで昇温しながら硬化し、ポリイミドフレキシブル金属積層体を製造した。その後、下記の物性を評価し、その結果を表2に示した。
前記表1の組成物Fの代わりに組成物Gを使用することを除き実施例5と同一の方法でポリイミドフレキシブル金属積層体を製造した。その後、下記の物性を評価し、その結果を表2に示した。
前記表1の組成物Bの代わりに組成物Aを使用することを除き実施例1と同一の方法でポリイミドフレキシブル金属積層体を製造した。その後、下記の物性を評価し、その結果を表2に示した。
Claims (4)
- 金属箔上に2層以上のポリイミド層を形成したポリイミド金属積層体であって、下記化学式1’から選択される何れか一つ以上のエポキシ化合物を含むポリアミック酸樹脂組成物からなるポリイミド層を一つ以上含む、ポリイミド金属積層体。
[化学式1’]
(前記化学式1’中、X1、X2はそれぞれ独立して、−CmH2m−CH3で置換または非置換され、Y1またはY2のうち何れか一つ以上は、
または
(p、qは1〜5の整数)から選択され、mは1〜5の整数、rは1〜10の自然数である。) - 金属箔とポリイミド層との間に、ビスマレイミド系、イミダゾール系又はイミダゾールトリアジン系化合物を添加したポリアミック酸樹脂組成物からなる接着剤層をさらに含む請求項1に記載のポリイミド金属積層体。
- エポキシ化合物を全組成物に対して1〜10重量%含有することを特徴とする請求項1又は2に記載のポリイミド金属積層体。
- ポリアミック酸樹脂組成物は、芳香族ジアミンと、下記化学式1’から選択される何れか一つ以上のエポキシ化合物と、芳香族ジアンヒドリドと、溶媒とを含む、請求項1〜3のいずれかに記載のポリイミド金属積層体。
[化学式1’]
(前記化学式1’中、X1、X2はそれぞれ独立して、−CmH2m−CH3で置換または非置換され、Y1またはY2のうち何れか一つ以上は、
または
(p、qは1〜5の整数)から選択され、mは1〜5の整数、rは1〜10の自然数である。)
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KR1020090128726A KR101439496B1 (ko) | 2009-12-22 | 2009-12-22 | 폴리아믹산 수지 조성물과 이의 제조방법 및 이를 이용한 폴리이미드 금속적층체 |
KR10-2009-0128726 | 2009-12-22 | ||
PCT/KR2010/009156 WO2011078553A2 (en) | 2009-12-22 | 2010-12-21 | Polyamic acid resin composition, method for preparing the same and polyimide metal clad laminate using the same |
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JP (1) | JP5922035B2 (ja) |
KR (1) | KR101439496B1 (ja) |
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US1989488A (en) * | 1929-12-27 | 1935-01-29 | Capstan Glass Co | Temperature control and regulating device and method |
US1997567A (en) * | 1934-06-20 | 1935-04-16 | Wilbur R Bennett | Treatment of ferrous metals |
US4883718A (en) * | 1985-02-12 | 1989-11-28 | Mitsui Toatsu Chemicals, Inc. | Flexible copper-clad circuit substrate |
US5171826A (en) * | 1989-03-23 | 1992-12-15 | Hitachi Chemical Company, Ltd. | Heat resistant adhesive composition and bonding method using the same |
JP3221756B2 (ja) * | 1992-12-28 | 2001-10-22 | 新日鐵化学株式会社 | プリント基板用耐熱性接着剤フィルム及びその使用方法並びにこれを用いたプリント基板の製造方法 |
JP2000022288A (ja) * | 1998-06-29 | 2000-01-21 | Sony Chem Corp | フレキシブルプリント基板及びその製造方法 |
JP3075472B2 (ja) * | 1998-08-07 | 2000-08-14 | 東邦レーヨン株式会社 | ポリイミド/エポキシ樹脂複合体及びその製法 |
WO2001057112A1 (fr) * | 2000-02-01 | 2001-08-09 | Nippon Steel Chemical Co., Ltd. | Resine polyimide adhesive et stratifie adhesif |
US6893681B2 (en) * | 2001-09-27 | 2005-05-17 | Fujitsu Limited | Surface conductive resin, a coaxial cable, a wiring board, and process for manufacturing the same |
JP4804705B2 (ja) * | 2003-04-24 | 2011-11-02 | 三井化学株式会社 | 金属張積層板 |
JP4525906B2 (ja) * | 2004-07-06 | 2010-08-18 | Jsr株式会社 | 液晶配向剤および液晶表示素子 |
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US20090130468A1 (en) * | 2007-11-16 | 2009-05-21 | Li-Hua Wang | Polyamic acid composition, method for preparing the same, method for preparing polyimide and polyimide flexible metal-clad laminates |
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CN102753625B (zh) | 2014-07-23 |
US20120315494A1 (en) | 2012-12-13 |
KR101439496B1 (ko) | 2014-09-12 |
WO2011078553A3 (en) | 2011-11-10 |
WO2011078553A2 (en) | 2011-06-30 |
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