JP5585022B2 - 感光性ポリイミド - Google Patents
感光性ポリイミド Download PDFInfo
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- JP5585022B2 JP5585022B2 JP2009184778A JP2009184778A JP5585022B2 JP 5585022 B2 JP5585022 B2 JP 5585022B2 JP 2009184778 A JP2009184778 A JP 2009184778A JP 2009184778 A JP2009184778 A JP 2009184778A JP 5585022 B2 JP5585022 B2 JP 5585022B2
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- DDKMFQGAZVMXQV-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CCl DDKMFQGAZVMXQV-UHFFFAOYSA-N 0.000 description 1
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- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
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- IUMRRUPGAXVMIE-UHFFFAOYSA-N [2-ethyl-4-(2-methylprop-2-enoyloxymethyl)hexyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CC)CC(CC)COC(=O)C(C)=C IUMRRUPGAXVMIE-UHFFFAOYSA-N 0.000 description 1
- IALCDEGIETXROH-UHFFFAOYSA-N [2-ethyl-4-(prop-2-enoyloxymethyl)hexyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CC)CC(CC)COC(=O)C=C IALCDEGIETXROH-UHFFFAOYSA-N 0.000 description 1
- OQHMGFSAURFQAF-UHFFFAOYSA-N [2-hydroxy-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)COC(=O)C(C)=C OQHMGFSAURFQAF-UHFFFAOYSA-N 0.000 description 1
- KNSXNCFKSZZHEA-UHFFFAOYSA-N [3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical class C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C KNSXNCFKSZZHEA-UHFFFAOYSA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- NKIDFMYWMSBSRA-UHFFFAOYSA-N [4-(2-methylprop-2-enoyloxymethyl)cyclohexyl]methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1CCC(COC(=O)C(C)=C)CC1 NKIDFMYWMSBSRA-UHFFFAOYSA-N 0.000 description 1
- VEBCLRKUSAGCDF-UHFFFAOYSA-N ac1mi23b Chemical compound C1C2C3C(COC(=O)C=C)CCC3C1C(COC(=O)C=C)C2 VEBCLRKUSAGCDF-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229960000880 allobarbital Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- ZDNFTNPFYCKVTB-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,4-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C=C1 ZDNFTNPFYCKVTB-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 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
- 239000004020 conductor Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- ZDSFBVVBFMKMRF-UHFFFAOYSA-N dimethyl-bis(prop-2-enyl)silane Chemical compound C=CC[Si](C)(C)CC=C ZDSFBVVBFMKMRF-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- PKHHQFAULPTXEW-UHFFFAOYSA-N ethane;prop-2-enoic acid Chemical compound CC.OC(=O)C=C PKHHQFAULPTXEW-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920005650 polypropylene glycol diacrylate Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- CQKAPARXKPTKBK-UHFFFAOYSA-N tert-butylazanium;bromide Chemical compound Br.CC(C)(C)N CQKAPARXKPTKBK-UHFFFAOYSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
- PLCFYBDYBCOLSP-UHFFFAOYSA-N tris(prop-2-enyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound C=CCOC(=O)CC(O)(CC(=O)OCC=C)C(=O)OCC=C PLCFYBDYBCOLSP-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 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
- C08G73/12—Unsaturated polyimide precursors
- C08G73/121—Preparatory processes from unsaturated precursors and polyamines
-
- 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
- C08G73/12—Unsaturated polyimide precursors
- C08G73/123—Unsaturated polyimide precursors the unsaturated precursors comprising halogen-containing substituents
-
- 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
- C08G73/12—Unsaturated polyimide precursors
- C08G73/124—Unsaturated polyimide precursors the unsaturated precursors 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
- C08G73/12—Unsaturated polyimide precursors
- C08G73/126—Unsaturated polyimide precursors the unsaturated precursors being wholly aromatic
-
- 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
- C08G73/12—Unsaturated polyimide precursors
- C08G73/126—Unsaturated polyimide precursors the unsaturated precursors being wholly aromatic
- C08G73/127—Unsaturated polyimide precursors the unsaturated precursors being wholly aromatic 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
- C08G73/14—Polyamide-imides
-
- 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
- C08L79/085—Unsaturated polyimide precursors
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0387—Polyamides or polyimides
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/037—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polyamides or polyimides
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
- H05K3/285—Permanent coating compositions
- H05K3/287—Photosensitive compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Materials For Photolithography (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
Description
式中、
Aは、少なくとも1個の変性基R1を有する4価の有機基を表し、
B及びDは、同一又は異なっており、それぞれ2価の有機基を表し、
Cは、変性基R1を全く有さない4価の有機基を表し、
mは、0を超える整数を表し、
nは、0又は0を超える整数を表しており、
この場合、この変性基R1は、
(式中、R2はビニル基を含有する不飽和基を表す)からなる群から選択され、不飽和基を含有する前記ビニル基は、下記:
(式中、R3は、H又はメチルであり、o及びpは、それぞれ整数0〜6、好ましくは2〜4を表す)から選択されることが好ましい。
(式中、R1は、
から選択される有機基である)から選択されることが好ましく、上式において、
R2は、本明細書において上記に定義した通りであり、
R4は、−CH2−、−O−、−S−、−CO−、−SO2−、−C(CH3)2−又は−C(CF3)2−であり、
R5は、−H又は−CH3であり、
Xは、−O−、−NH−又は−S−である。
(式中、
R7は、H、メチル又はエチルであり、
R8は、H、C1〜C4アルキル、C1〜C4ペルフルオロアルキル、メトキシ、エトキシ、ハロゲン、OH、COOH、NH2又はSHであり、
aは0を超える整数であり、
bは0を超える整数であり、
cは0〜4の整数であり、
dは0〜4の整数であり、
R9は、共有結合、又は
(式中、w及びxはそれぞれ0を超える整数を表し、R11は、−S(O)2−、−C(O)−、共有結合、又は置換された若しくは非置換のC1〜C18有機基である)から選択される基である)からなる群から選択されることが好ましい。
(式中、R3はH又はメチルであり、o及びpはそれぞれ0〜6の整数、好ましくは2〜4の整数を表す)であることが好ましいが、それらに限定されない。
(a)式H2N−P−NH2のジアミンモノマーを、式
の酸二無水物モノマー、及び他の酸二無水物モノマー
と反応させて、次の式(1):
(式中、Gは、OH、COOH又はNH2の基などの反応性官能基である)の化合物を形成するステップ、並びに、GがCOOHである場合、次のステップ:
(b)エポキシ化合物、例えばメタクリル酸グリシジルを、ステップ(a)から得られた生成物に添加して、式(2):
(式中、f+g=iである)の化合物を形成するステップ
を実施する方法などの重合方法により生成させることができる。
(式中、
R7は、H、メチル又はエチルを表し、
R8は、H、C1〜C4アルキル、C1〜C4ペルフルオロアルキル、メトキシ、エトキシ、ハロゲン、OH、COOH、NH2又はSHを表し、
aは0を超える整数であり、
bは0を超える整数であり、
cは0〜4の整数であり、
dは0〜4の整数であり、
R9は、共有結合、又は
(式中、w及びxはそれぞれ0を超える整数を表し、R11は、−S(O)2−、−C(O)−、共有結合、又は置換された若しくは非置換のC1〜C18有機基である)から選択される基である)が含まれるが、それらに限定されない。
(式中、
R4は、−CH2−、−O−、−S−、−CO−、−SO2−、−C(CH3)2−又は−C(CF3)2−を表し、
R5は、−H又は−CH3を表し、
R6は、OH、COOH又はNH2を表し、
Xは、−O−、−NH−又は−S−である)から選択することができる。
(式中、
E、F及びHは、それぞれ共有結合、又は置換された若しくは非置換のC1〜C20飽和若しくは不飽和、環状若しくは鎖状有機基であり、
R20は、共有結合、又は下記から選択される基を表す)が含まれるが、それらに限定されない:
6FDA:4,4’−ヘキサフルオロイソプロピリデン−2,2−ビス−(無水フタル酸
DMDB:2,2’−ジメチルビフェニル−4,4’−ジアミン
ODA:4,4’−オキシジアニリン
GMA:メタクリル酸グリシジル
TBAB:臭化tert−ブチルアンモニウム
MEHQ:メチルヒドロキノ
DMAc:ジメチルアセトアミド
NMP:N−メチルピロリドン
64.85g(0.2モル)のDA1及び42.46g(0.2モル)のDMDBを、300mLのNMPに添加した。この混合物を、室温で1時間撹拌し、次いで50℃まで加温し、4時間撹拌した。その後、50mLのキシレンを添加し、ディーン−スターク(dean−stark)装置により130℃で水分を除去した。水分を完全に除去した後、この溶液を室温まで冷却し、6.11g(0.05モル)のGMA、0.015gのTBAB及び0.06gのMEHQを添加した。この添加が終わった後、溶液を90℃まで加温し、12時間撹拌して、P1を得た。
73.256g(0.2モル)のDA2及び42.46g(0.2モル)のDMDBを、350mLのNMPに添加した。この混合物を、室温で1時間撹拌し、次いで50℃まで加温し、4時間撹拌した。その後、50mLのキシレンを添加し、ディーン−スターク装置により130℃で水分を除去した。水分を完全に除去した後、この溶液を室温まで冷却し、6.11g(0.05モル)のGMA、0.015gのTBAB及び0.06gのMEHQを添加した。この添加が終わった後、溶液を90℃まで加温し、12時間撹拌して、P2を得た。
100.074g(0.2モル)のDA3及び42.46g(0.2モル)のDMDBを、450mLのNMPに添加した。この混合物を、室温で1時間撹拌し、次いで50℃まで加温し、4時間撹拌した。その後、50mLのキシレンを添加し、ディーン−スターク装置により130℃で水分を除去した。水分を完全に除去した後、この溶液を室温まで冷却し、6.11g(0.05モル)のGMA、0.015gのTBAB及び0.06gのMEHQを添加した。この添加が終わった後、溶液を90℃まで加温し、12時間撹拌して、P3を得た。
124.1g(0.2モル)のDA4及び42.46g(0.2モル)のDMDBを、550mLのNMPに添加した。この混合物を、室温で1時間撹拌し、次いで50℃まで加温し、4時間撹拌した。その後、50mLのキシレンを添加し、ディーン−スターク装置により130℃で水分を除去した。水分を完全に除去した後、この溶液を室温まで冷却し、12.22g(0.1モル)のGMA、0.03gのTBAB及び0.06gのMEHQを添加した。この添加が終わった後、溶液を90℃まで加温し、12時間撹拌して、P4を得た。
126.9g(0.2モル)のDA5及び42.46g(0.2モル)のDMDBを、550mLのNMPに添加した。この混合物を、室温で1時間撹拌し、次いで50℃まで加温し、4時間撹拌した。その後、50mLのキシレンを添加し、ディーン−スターク装置により130℃で水分を除去した。水分を完全に除去した後、この溶液を室温まで冷却し、12.22g(0.1モル)のGMA、0.03gのTBAB及び0.06gのMEHQを添加した。この添加が終わった後、溶液を90℃まで加温し、12時間撹拌して、P5を得た。
115.7g(0.2モル)のDA6及び42.46g(0.2モル)のDMDBを、500mLのNMPに添加した。この混合物を、室温で1時間撹拌し、次いで50℃まで加温し、4時間撹拌した。その後、50mLのキシレンを添加し、ディーン−スターク装置により130℃で水分を除去した。水分を完全に除去した後、この溶液を室温まで冷却し、6.11g(0.05モル)のGMA、0.015gのTBAB及び0.06gのMEHQを添加した。この添加が終わった後、溶液を90℃まで加温し、12時間撹拌して、P6を得た。
64.85g(0.2モル)のDA1及び40.05g(0.2モル)のODAを、300mLのDMAcに添加した。この混合物を、室温で1時間撹拌し、次いで50℃まで加温し、4時間撹拌した。その後、50mLのキシレンを添加し、ディーン−スターク装置により130℃で水分を除去した。水分を完全に除去した後、この溶液を室温まで冷却し、6.11g(0.05モル)のGMA、0.015gのTBAB及び0.06gのMEHQを添加した。この添加が終わった後、溶液を90℃まで加温し、12時間撹拌して、P7を得た。
73.26g(0.2モル)のDA2及び40.05g(0.2モル)のODAを、350mLのDMAcに添加した。この混合物を、室温で1時間撹拌し、次いで50℃まで加温し、4時間撹拌した。その後、50mLのキシレンを添加し、ディーン−スターク装置により130℃で水分を除去した。水分を完全に除去した後、この溶液を室温まで冷却し、6.11g(0.05モル)のGMA、0.015gのTBAB及び0.06gのMEHQを添加した。この添加が終わった後、溶液を90℃まで加温し、12時間撹拌して、P8を得た。
100.074g(0.2モル)のDA3及び40.05g(0.2モル)のODAを、450mLのDMAcに添加した。この混合物を、室温で1時間撹拌し、次いで50℃まで加温し、4時間撹拌した。その後、50mLのキシレンを添加し、ディーン−スターク装置により130℃で水分を除去した。水分を完全に除去した後、この溶液を室温まで冷却し、6.11g(0.05モル)のGMA、0.015gのTBAB及び0.06gのMEHQを添加した。この添加が終わった後、溶液を90℃まで加温し、12時間撹拌して、P9を得た。
124.1g(0.2モル)のDA4及び40.05g(0.2モル)のODAを、550mLのDMAcに添加した。この混合物を、室温で1時間撹拌し、次いで50℃まで加温し、4時間撹拌した。その後、50mLのキシレンを添加し、ディーン−スターク装置により130℃で水分を除去した。水分を完全に除去した後、この溶液を室温まで冷却し、12.22g(0.1モル)のGMA、0.03gのTBAB及び0.06gのMEHQを添加した。この添加が終わった後、溶液を90℃まで加温し、12時間撹拌して、P10を得た。
126.9g(0.2モル)のDA5及び40.05g(0.2モル)のODAを、550mLのDMAcに添加した。この混合物を、室温で1時間撹拌し、次いで50℃まで加温し、4時間撹拌した。その後、50mLのキシレンを添加し、ディーン−スターク装置により130℃で水分を除去した。水分を完全に除去した後、この溶液を室温まで冷却し、12.22g(0.1モル)のGMA、0.03gのTBAB及び0.06gのMEHQを添加した。この添加が終わった後、溶液を90℃まで加温し、12時間撹拌して、P11を得た。
115.7g(0.2モル)のDA6及び40.05g(0.2モル)のODAを、550mLのDMAcに添加した。この混合物を、室温で1時間撹拌し、次いで50℃まで加温し、4時間撹拌した。その後、50mLのキシレンを添加し、ディーン−スターク装置により130℃で水分を除去した。水分を完全に除去した後、この溶液を室温まで冷却し、6.11g(0.05モル)のGMA、0.015gのTBAB及び0.06gのMEHQを添加した。この添加が終わった後、溶液を90℃まで加温し、12時間撹拌して、P12を得た。
57.85g(0.1モル)のDA4、44.42g(0.1モル)の6FDA及び40.05g(0.2モル)のODAを、500mLのDMAcに添加した。この混合物を、室温で1時間撹拌し、次いで50℃まで加温し、4時間撹拌した。その後、50mLのキシレンを添加し、ディーン−スターク装置により130℃で水分を除去した。水分を完全に除去した後、この溶液を室温まで冷却し、6.11g(0.05モル)のGMA、0.015gのTBAB及び0.06gのMEHQを添加した。この添加が終わった後、溶液を90℃まで加温し、12時間撹拌して、P13を得た。
63.45g(0.1モル)のDA5、44.42g(0.1モル)の6FDA及び40.05g(0.2モル)のODAを、500mLのDMAcに添加した。この混合物を、室温で1時間撹拌し、次いで50℃まで加温し、4時間撹拌した。その後、50mLのキシレンを添加し、ディーン−スターク装置により130℃で水分を除去した。水分を完全に除去した後、この溶液を室温まで冷却し、6.11g(0.05モル)のGMA、0.015gのTBAB及び0.06gのMEHQを添加した。この添加が終わった後、溶液を90℃まで加温し、12時間撹拌して、P14を得た。
Claims (10)
- 請求項1に記載の感光性ポリイミドと光開始剤とを含む、感光性組成物。
- 反応性モノマー又はオリゴマーをさらに含む、請求項8に記載の感光性組成物。
- 液状フォトレジスト又はドライフィルムレジストにおいて使用するための、請求項8に記載の感光性組成物。
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US9285680B2 (en) | 2014-07-16 | 2016-03-15 | Taiflex Scientific Co., Ltd. | Photosensitive polyimide composition, base agent thereof, method of making the base agent, and solder-resistant polyimide thin film made from the composition |
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