CN116751152A - Imide structure photosensitive developing resin and preparation method and application thereof - Google Patents
Imide structure photosensitive developing resin and preparation method and application thereof Download PDFInfo
- Publication number
- CN116751152A CN116751152A CN202310708449.2A CN202310708449A CN116751152A CN 116751152 A CN116751152 A CN 116751152A CN 202310708449 A CN202310708449 A CN 202310708449A CN 116751152 A CN116751152 A CN 116751152A
- Authority
- CN
- China
- Prior art keywords
- parts
- imide
- photosensitive developing
- developing resin
- reaction
- 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
- 229920005989 resin Polymers 0.000 title claims abstract description 45
- 239000011347 resin Substances 0.000 title claims abstract description 45
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 125000005462 imide group Chemical group 0.000 title abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 54
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 26
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910000679 solder Inorganic materials 0.000 claims abstract description 16
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 15
- 229920000768 polyamine Polymers 0.000 claims abstract description 13
- 239000003112 inhibitor Substances 0.000 claims abstract description 12
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 11
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229940057499 anhydrous zinc acetate Drugs 0.000 claims abstract description 11
- 235000019253 formic acid Nutrition 0.000 claims abstract description 11
- DJWUNCQRNNEAKC-UHFFFAOYSA-L zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 claims abstract description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims abstract description 10
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 8
- -1 alicyclic acid anhydride Chemical class 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 4
- 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 43
- 239000000047 product Substances 0.000 claims description 32
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 24
- 150000003949 imides Chemical group 0.000 claims description 22
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 21
- 238000010438 heat treatment Methods 0.000 claims description 19
- 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 15
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 15
- 239000000843 powder Substances 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 15
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 14
- 239000012044 organic layer Substances 0.000 claims description 14
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 238000000227 grinding Methods 0.000 claims description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 7
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 7
- 238000002390 rotary evaporation Methods 0.000 claims description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 6
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 claims description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 150000004985 diamines Chemical class 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 claims description 2
- JTTIOYHBNXDJOD-UHFFFAOYSA-N 2,4,6-triaminopyrimidine Chemical compound NC1=CC(N)=NC(N)=N1 JTTIOYHBNXDJOD-UHFFFAOYSA-N 0.000 claims description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims description 2
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 claims description 2
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 claims description 2
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- OXIKYYJDTWKERT-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCC(CN)CC1 OXIKYYJDTWKERT-UHFFFAOYSA-N 0.000 claims description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 2
- 238000000016 photochemical curing Methods 0.000 claims description 2
- 229920001187 thermosetting polymer Polymers 0.000 claims description 2
- 239000004642 Polyimide Substances 0.000 abstract description 4
- 229920001721 polyimide Polymers 0.000 abstract description 4
- 150000008065 acid anhydrides Chemical class 0.000 abstract description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- 239000002131 composite material Substances 0.000 abstract description 2
- 239000002861 polymer material Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000007747 plating Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 238000011161 development Methods 0.000 description 7
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 6
- 229910052737 gold Inorganic materials 0.000 description 6
- 239000010931 gold Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 5
- 238000005530 etching Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000010410 layer Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- 238000009713 electroplating Methods 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 238000012536 packaging technology Methods 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 240000005002 Erythronium dens canis Species 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000007772 electroless plating Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004901 spalling Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Indole Compounds (AREA)
Abstract
The invention belongs to the technical field of high polymer materials, and particularly relates to an imide structure photosensitive developing resin and a preparation method and application thereof. The raw materials of the composite material comprise the following components in parts by weight: 2-6 parts of polyamine, 6-20 parts of dicarboxylic anhydride, 1-6 parts of unsaturated monobasic acid, 0.02-0.08 part of polymerization inhibitor, 0.02-0.08 part of catalyst, 2-10 parts of hydrogen peroxide, 2-6 parts of saturated sodium bicarbonate solution, 1-5 parts of diethyl ether, 3-10 parts of formic acid, 50-70 parts of N-methylpyrrolidone and 2-8 parts of anhydrous zinc acetate. The invention firstly reacts polyamine with alicyclic acid anhydride with double bond to generate a polyimide structure with double bond at the terminal, then epoxidizes the double bond, then uses unsaturated monobasic acid to open loop and esterify, then uses acid anhydride to modify, and introduces carboxyl, finally obtains the photosensitive developing resin with imide structure. The resin has excellent electrical properties, heat resistance, good dimensional stability, excellent adhesion and low dielectric constant, and is suitable for preparing IC carrier plate ink, printed circuit board solder resist ink or chip photoresist.
Description
Technical Field
The invention belongs to the technical field of high polymer materials, and particularly relates to an imide structure photosensitive developing resin and a preparation method and application thereof.
Background
The last century of IC carrier technology originates in Japan in the 80 th year, and has been developed for more than 30 years so far, and early and IC integrated packaging technologies coexist, and currently, high-end ICs basically adopt carrier packaging technologies as precise connection devices between core chips and conventional Printed Circuit Boards (PCBs). The IC carrier plate is manufactured by the copper-clad plate through the processes of photoetching, solder resist photosensitive development, gold plating and the like, and is different from the traditional copper plate of the PCB in several aspects. Firstly, the base material used by the IC carrier plate copper-clad plate is different from the epoxy/glass fiber composite material of the traditional copper-clad plate, and BT resin, ABF insulating Film (Ajinomoto Build-up Film of Weisu company) and MIS polymer are mainly adopted as the base material of the copper-clad plate (Film), and the three base materials are monopolized by foreign enterprises. Secondly, the IC carrier board is manufactured from a special copper-clad plate (film), and the circuit etching and the solder mask photosensitive development processing are required to be finer than the conventional PCB manufacturing, namely, the etching and solder mask development resolution is higher, and the line width is usually controlled within the range of tens of micrometers. Thirdly, the solder resist photosensitive developing ink is used as a permanent fine protective thin layer material, and is required to have severe heat resistance, thermal expansion resistance, hardness, scratch resistance and impact resistance on an IC carrier plate, and even certain application occasions also require the solder resist layer to have lower dielectric constant so as to meet the requirement of high-frequency communication. Fourth, most of the back-end processing of the IC carrier plate adopts electroless gold plating (industrial abbreviated as gold plating), but electroless plating, and gold plating liquid medicine generally has stronger acidity or alkalinity, thus the solder mask of the IC carrier plate is required to have higher gold plating resistance (namely corrosion resistance), and the defects of color change, denaturation, easy spalling and the like of the solder mask are avoided. Therefore, compared with the traditional PCB solder resist ink, the IC carrier solder resist ink has more stringent requirements on indexes such as development resolution, development quality, thermal expansion resistance, gold melting resistance and the like, and the technical key of the IC carrier solder resist ink is photosensitive development main resin and a photoinitiation system. Therefore, it is necessary to improve the performance index of the photosensitive developing main resin to meet the requirements of the IC carrier.
Disclosure of Invention
The first object of the present invention is to provide an imide-structured photosensitive developing resin, the second object of the present invention is to provide a method for producing the photosensitive developing resin, and the third object of the present invention is to provide an application of the photosensitive developing resin.
According to a first aspect of the present invention, there is provided an imide-structured photosensitive developing resin comprising, in parts by weight: 2-6 parts of polyamine, 6-20 parts of dicarboxylic anhydride, 1-6 parts of unsaturated monobasic acid, 0.02-0.08 part of polymerization inhibitor, 0.02-0.08 part of catalyst, 2-10 parts of hydrogen peroxide, 2-6 parts of saturated sodium bicarbonate solution, 1-5 parts of diethyl ether, 3-10 parts of formic acid, 50-70 parts of N-methylpyrrolidone and 2-8 parts of anhydrous zinc acetate.
In some embodiments, the polyamine is selected from one or more of 4,4 '-diaminodicyclohexylmethane, 1, 4-cyclohexanedimethylamine, 1, 3-cyclohexanedimethylamine, 4' - (p-dimethylamino) diphenylmethane, isophorone diamine, 1, 8-octanediamine, polyoxyethylene diamine, 2,4, 6-triaminopyrimidine. The toughness and film forming property of the chain polyamine derived imide structure photosensitive developing resin can be improved; the alicyclic polyamine derived imide structure photosensitive developing resin is rigid and tough and has better balance performance; the performance of the imide structure photosensitive developing resin derived from aromatic polyamine is biased to rigidity, brittleness and poor solubility and film forming property. Therefore, the three components are generally matched, and the balance performance is balanced by opposite impact.
In some embodiments, the dicarboxylic acid anhydride is selected from one or more of tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyl tetrahydrophthalic anhydride.
In some embodiments, the unsaturated monoacid is selected from one or more of acrylic acid, methacrylic acid, butenoic acid.
In some embodiments, the polymerization inhibitor is selected from at least one of hydroquinone, p-tert-butylcatechol, catechol.
In some embodiments, the catalyst is selected from one or more of benzyltriethylammonium chloride, benzyldiamine, triethylamine, diethylamine, triphenylphosphine.
According to a second aspect of the present invention, there is provided a method for producing the above imide-structured photosensitive developing resin, comprising the steps of:
s1, mixing dicarboxylic anhydride accounting for 40-60% of the total dicarboxylic anhydride, polyamine, anhydrous zinc acetate, polymerization inhibitor accounting for 20-30% of the total polymerization inhibitor and N-methylpyrrolidone, heating to 70-80 ℃ in a nitrogen atmosphere, stirring for 0.5-2h, then heating to 140-160 ℃, continuously stirring for 15-18 h, cooling the reaction solution to 20-35 ℃ after the reaction is finished, filtering, washing with absolute ethyl alcohol, drying and grinding the product to obtain bismaleimide solid powder;
s2, mixing the bismaleimide solid powder prepared in the step S1 with formic acid, stirring for 1-3 hours at 50-60 ℃, then adding hydrogen peroxide, continuing to react for 3-5 hours, adding saturated sodium bicarbonate solution and diethyl ether into a reaction product after the reaction is completed, shaking uniformly, standing for layering, separating an organic layer, washing the organic layer with water for 2-3 times, removing diethyl ether by rotary evaporation, adding anhydrous magnesium sulfate, drying overnight, and filtering to remove magnesium sulfate to obtain a product;
s3, mixing the product obtained in the step S2 with the rest of polymerization inhibitor and catalyst, heating the system to 90-100 ℃, then adding unsaturated monobasic acid, heating to 110-120 ℃ after the addition, continuing to react for 2-3h, cooling the temperature of the reaction system to 70-90 ℃ after the reaction is completed, then adding the rest of dicarboxylic anhydride, and reacting for 6-8h to obtain the catalyst.
In step S1, anhydrous zinc acetate is used for adsorbing water generated in the reaction, and N-methylpyrrolidone is used as a solvent.
In the step S1, a staged heating mode is adopted, so that all reaction raw materials are uniformly mixed at a lower temperature (70-80 ℃) to avoid local explosion polymerization in the subsequent high-temperature (140-160 ℃) reaction.
In step S2, the formic acid mainly serves to provide a weak acid environment to enhance the oxidizing property of hydrogen peroxide.
In step S2, the diethyl ether serves to provide the organic phase in the extraction.
In the step S3, the main reaction raw materials, the polymerization inhibitor and the catalyst are uniformly mixed, the temperature is increased to 90-100 ℃, at this time, unsaturated monoacid is added, self-polymerization is not easy to occur, and the temperature is increased to 110-120 ℃ after uniform stirring, so that the explosion polymerization of the unsaturated monoacid can be further prevented.
The invention introduces the imide structure into the photosensitive development main resin, and continues grafting to increase the functionality of the resin on the basis of the generated polyimide. The invention firstly reacts polyamine with alicyclic acid anhydride with double bond to generate a polyimide structure with double bond at the terminal, then epoxidizes the double bond, then uses unsaturated monobasic acid to open loop and esterify, then uses acid anhydride to modify, and introduces carboxyl, finally obtains the photosensitive developing resin with imide structure. The resin has the advantages of excellent electrical property, heat resistance, good dimensional stability, excellent adhesion, low dielectric constant and the like.
When the dicarboxylic anhydride is tetrahydrophthalic anhydride, the polyamine is 1, 3-cyclohexanedimethylamine, and the unsaturated monoacid is acrylic acid, the synthetic route of the invention is schematically shown in figure 1.
In some embodiments, in step S1, the product is dried in a vacuum oven at 50℃for 4-6 hours, after which the bismaleimide solid powder is obtained.
In some embodiments, in step S2, hydrogen peroxide is slowly added dropwise, and the adding time is controlled to be 2-4h.
In some embodiments, the rotational speed of the stirring is 600-800rpm.
According to a third aspect of the present invention, there is provided an application of the above-mentioned imide-structured photosensitive developing resin in preparing an IC carrier plate solder resist ink, a printed circuit board solder resist ink or a chip photoresist.
According to a fourth aspect of the present invention, there is provided a dry film obtained by photo-curing or thermosetting the above-mentioned imide-structured photosensitive developing resin.
In some embodiments, the imide structure photosensitive developing resin is printed on a carrier and baked at 70-80 ℃ for 20-30 minutes to obtain a dry film.
According to a fifth aspect of the present invention there is provided the use of a dry film as described above in the preparation of an IC carrier board or printed circuit board.
The beneficial effects of the invention include:
the photosensitive developing resin with the imide structure has lower molecular weight, and the low molecular weight polybasic imide structure oligomer can lead the cured film obtained after the resin is cured to have higher glass transition temperature and lower thermal expansion performance, and meanwhile, the polyimide cured film is formed by crosslinking and curing a plurality of imide structures through double bonds, so that the photosensitive developing resin has excellent heat resistance, thermal expansion resistance and dimensional stability, and can meet the severe requirements of IC carrier plate solder resist ink on line width precision and thermal deformation resistance.
Drawings
FIG. 1 is a schematic diagram of the synthetic route of example 1 of the present invention.
Detailed Description
The following examples are given for the purpose of illustration only and are not intended to limit the scope of the invention. The process steps not disclosed in the examples are prior art. Unless otherwise specified, the following materials are all commercially available.
In the examples below, the stirring speed was 600rpm.
Example 1
The preparation method of the imide structure photosensitive developing resin comprises the following steps:
(1) 50.00g of tetrahydrophthalic anhydride, 46.74g of 1, 3-cyclohexanedimethylamine, 60.30g of anhydrous zinc acetate, 0.16g of hydroquinone and 1.00L N-methylpyrrolidone were placed in a 3L round bottom four neck flask equipped with a nitrogen inlet and thermometer, and the mixture was heated to 80℃under nitrogen and stirred for half an hour, then heated to 150℃and stirred for 16 hours. After the reaction was completed, the reaction solution was cooled to room temperature, suction-filtered and washed 3 times with absolute ethanol, and the product was dried in a vacuum oven at 50 ℃ for 4 hours, followed by grinding to obtain bismaleimide solid powder.
(2) 29.35g of the bismaleimide solid powder obtained in the step (1) and 75.85g of formic acid are added into a three-necked flask, stirred for 2 hours at 50 ℃, then 48.89g of hydrogen peroxide is slowly added dropwise for about 3 hours, the reaction is continued for 5 hours after the dropwise addition is completed, the reaction product is poured into a separating funnel after the completion of the reaction, then 50g of saturated sodium bicarbonate solution and 25g of diethyl ether are added, the mixture is uniformly shaken and then is left to stand for layering, the organic layer is separated, then the organic layer is washed 3 times by distilled water, the washed product is poured into a beaker, diethyl ether is removed by rotary evaporation, then 30g of anhydrous magnesium sulfate is added for overnight and dried, and then the magnesium sulfate is removed by filtration, thus obtaining a dried product.
(3) Adding 31.32g of the dried product obtained in the step (2) into another three-mouth bottle, adding 0.48g of hydroquinone and 0.32g of benzyl triethyl ammonium chloride, heating the system to 90 ℃, then dropwise adding 28.53g of acrylic acid into the three-mouth bottle, heating to 110 ℃ after the dropwise adding is finished, continuing to react for 2.5h, reducing the temperature of the reaction system to 80 ℃ after the reaction is finished, adding 60.23g of tetrahydrophthalic anhydride, and reacting for 6h to obtain the finished product.
Example 2
The preparation method of the imide structure photosensitive developing resin comprises the following steps:
(1) 50.00g of tetrahydrophthalic anhydride, 46.23g of 1, 8-octanediamine, 60.30g of anhydrous zinc acetate, 0.16g of hydroquinone and 1.00L N-methylpyrrolidone were placed in a 3L round-bottomed four-necked flask equipped with a nitrogen inlet and thermometer, and the mixture was heated to 80℃under nitrogen atmosphere and stirred for half an hour, then heated to 150℃and stirred for 16 hours. After the reaction was completed, the reaction solution was cooled to room temperature, suction-filtered and washed 3 times with absolute ethanol, and the product was dried in a vacuum oven at 50 ℃ for 4 hours, followed by grinding to obtain bismaleimide solid powder.
(2) 29.35g of the bismaleimide solid powder obtained in the step (1) and 75.85g of formic acid are added into a three-necked flask, stirred for 2 hours at 50 ℃, then 48.89g of hydrogen peroxide is slowly added dropwise for about 3 hours, the reaction is continued for 5 hours after the dropwise addition is completed, the reaction product is poured into a separating funnel after the completion of the reaction, then 50g of saturated sodium bicarbonate solution and 25g of diethyl ether are added, the mixture is uniformly shaken and then is left to stand for layering, the organic layer is separated, then the organic layer is washed 3 times by distilled water, the washed product is poured into a beaker, diethyl ether is removed by rotary evaporation, then 30g of anhydrous magnesium sulfate is added for overnight and dried, and then the magnesium sulfate is removed by filtration, thus obtaining a dried product.
(3) Adding 31.32g of the dried product obtained in the step (2) into another three-mouth bottle, adding 0.48g of hydroquinone and 0.32g of benzyl triethyl ammonium chloride, heating the system to 90 ℃, then dropwise adding 28.53g of acrylic acid into the three-mouth bottle, heating to 110 ℃ after the dropwise adding is finished, continuing to react for 2.5h, reducing the temperature of the reaction system to 80 ℃ after the reaction is finished, adding 60.23g of tetrahydrophthalic anhydride, and reacting for 6h to obtain the finished product.
Example 3
The preparation method of the imide structure photosensitive developing resin comprises the following steps:
(1) 50.00g of tetrahydrophthalic anhydride, 41.23g of polyoxyethylene diamine, 60.30g of anhydrous zinc acetate, 0.16g of hydroquinone and 1.00L N-methylpyrrolidone are placed in a 3L round-bottomed four-necked flask equipped with a nitrogen inlet and thermometer, and the mixture is heated to 80℃under nitrogen atmosphere and stirred for half an hour, then heated to 150℃and stirred for 16 hours. After the reaction is completed, the reaction solution is cooled to room temperature, filtered by suction and washed with absolute ethyl alcohol for 2 times, the product is dried in a vacuum oven at 50 ℃ for 4 hours, and the bismaleimide solid powder is obtained after grinding.
(2) 27.74g of the bismaleimide solid powder obtained in the step (1) and 75.85g of formic acid are added into a three-necked flask, stirred for 2 hours at 50 ℃, 48.89g of hydrogen peroxide is slowly added dropwise, the dropwise addition time is about 3 hours, the reaction is continued for 5 hours after the dropwise addition is completed, the reaction product is poured into a separating funnel, 50g of saturated sodium bicarbonate solution and 25g of diethyl ether are added, the mixture is uniformly shaken and then is left to stand for layering, the organic layer is washed 3 times by distilled water after the organic layer is separated, the washed product is poured into a beaker, diethyl ether is removed by rotary evaporation, 30g of anhydrous magnesium sulfate is added for overnight drying, and then the magnesium sulfate is removed by filtration, so that a dried product is obtained.
(3) Adding 31.32g of the dried product obtained in the step (2) into another three-mouth bottle, adding 0.48g of hydroquinone and 0.32g of benzyl triethyl ammonium chloride, heating the system to 90 ℃, then dropwise adding 28.53g of acrylic acid into the three-mouth bottle, heating to 110 ℃ after the dropwise adding is finished, continuing to react for 2.5h, reducing the temperature of the reaction system to 80 ℃ after the reaction is finished, adding 60.23g of tetrahydrophthalic anhydride, and reacting for 6h to obtain the finished product.
Example 4
The preparation method of the imide structure photosensitive developing resin comprises the following steps:
(1) 50.00g of tetrahydrophthalic anhydride, 23.37g of 1, 3-cyclohexanedimethylamine, 20.62g of polyoxyethylene diamine, 60.30g of anhydrous zinc acetate, 0.16g of hydroquinone and 1.00L N-methylpyrrolidone were placed in a 3L round-bottomed four-necked flask equipped with a nitrogen inlet and thermometer, and the mixture was heated to 80℃under nitrogen atmosphere and stirred for half an hour, then heated to 150℃and stirred for 16 hours. After the reaction is completed, the reaction solution is cooled to room temperature, filtered by suction and washed with absolute ethyl alcohol for 2 times, the product is dried in a vacuum oven at 50 ℃ for 4 hours, and the bismaleimide solid powder is obtained after grinding.
(2) 28.79g of the bismaleimide solid powder obtained in the step (1) and 75.85g of formic acid are added into a three-necked flask, stirred for 2 hours at 50 ℃, 48.89g of hydrogen peroxide is slowly added dropwise, the dropwise addition time is about 3 hours, the reaction is continued for 5 hours after the dropwise addition is completed, the reaction product is poured into a separating funnel after the reaction is completed, 50g of saturated sodium bicarbonate solution and 25g of diethyl ether are added, the mixture is kept stand for layering after shaking uniformly, the organic layer is separated, the organic layer is washed 3 times by distilled water, the washed product is poured into a beaker, diethyl ether is removed by rotary evaporation, 30g of anhydrous magnesium sulfate is added for overnight drying, and then magnesium sulfate is removed by filtration, so that a dried product is obtained.
(3) Adding 31.32g of the dried product obtained in the step (2) into another three-mouth bottle, adding 0.48g of hydroquinone and 0.32g of benzyl triethyl ammonium chloride, heating the system to 90 ℃, then dropwise adding 28.53g of acrylic acid into the three-mouth bottle, heating to 110 ℃ after the dropwise adding is finished, continuing to react for 2.5h, reducing the temperature of the reaction system to 80 ℃ after the reaction is finished, adding 60.23g of tetrahydrophthalic anhydride, and reacting for 6h to obtain the finished product.
Example 5
The preparation method of the imide structure photosensitive developing resin comprises the following steps:
(1) 50.00g of tetrahydrophthalic anhydride, 23.37g of 1, 3-cyclohexanedimethylamine, 23.12g of 1, 8-octanediamine, 60.30g of anhydrous zinc acetate, 0.16g of hydroquinone and 1.00L N-methylpyrrolidone are placed in a 3L round-bottomed four-necked flask equipped with a nitrogen inlet and thermometer, and the mixture is heated to 80℃under nitrogen atmosphere and stirred for half an hour, then heated to 150℃and stirred for 16 hours. After the reaction is completed, the reaction solution is cooled to room temperature, filtered by suction and washed with absolute ethyl alcohol for 2 times, the product is dried in a vacuum oven at 50 ℃ for 4 hours, and the bismaleimide solid powder is obtained after grinding.
(2) 29.78g of the bismaleimide solid powder obtained in the step (1) and 75.85g of formic acid are added into a three-necked flask, stirred for 2 hours at 50 ℃, 48.89g of hydrogen peroxide is slowly added dropwise, the dropwise addition time is about 3 hours, the reaction is continued for 5 hours after the dropwise addition is completed, the reaction product is poured into a separating funnel after the reaction is completed, 50g of saturated sodium bicarbonate solution and 25g of diethyl ether are added, the mixture is kept stand for layering after shaking uniformly, the organic layer is separated, the organic layer is washed 3 times by distilled water, the washed product is poured into a beaker, diethyl ether is removed by rotary evaporation, 30g of anhydrous magnesium sulfate is added for overnight drying, and then magnesium sulfate is removed by filtration, so that a dried product is obtained.
(3) Adding 31.32g of the dried product obtained in the step (2) into another three-mouth bottle, adding 0.48g of hydroquinone and 0.32g of benzyl triethyl ammonium chloride, heating the system to 90 ℃, then dropwise adding 28.53g of acrylic acid into the three-mouth bottle, heating to 110 ℃ after the dropwise adding is finished, continuing to react for 2.5h, reducing the temperature of the reaction system to 80 ℃ after the reaction is finished, adding 60.23g of tetrahydrophthalic anhydride, and reacting for 6h to obtain the finished product.
The imide-structured photosensitive developing resins prepared in examples 1 to 5 were subjected to the following performance test, as follows:
(1) Photosensitivity: printing an imide structure photosensitive developing resin on a copper-clad plate, baking for 20 minutes at 75 ℃, placing a 21-level light gradient ruler above the film layer, exposing and developing under an exposure machine of an LED light source, and taking the time of 7 grids remained on the film layer as a standard.
(2) Minimum line width: the test was carried out according to the method of GB/T29846-2013 printing plate with photoimaging plating resist.
(3) Etch resistance: the etching resistance is tested according to the method of using the photoimaging electroplating-resistant resist of the GB/T29846-2013 printed board, so that the visual pattern is complete after etching, the line edge is neat, no wrinkling and falling off or the dog tooth shape is good, the wrinkling and falling off are poor.
(4) Plating resistance: the plating resistance was tested according to the method of using photoimaging plating resist for GB/T29846-2013 printed boards, and the visual inspection pattern after plating showed no, no bubbles and poor plating, no dropping was good.
(5) Film-removing property: the test sample plate is placed in a NaOH aqueous solution with the temperature of 50 ℃ and the weight percentage of 3 percent, and the quality of film removal performance is observed, so that the quality of film removal performance is good when the film is completely removed within 60 seconds, the film is completely removed within 60-120 seconds, and the film is completely removed without residues after 120 seconds.
The test results are shown in Table 1.
TABLE 1 results of Performance test of imide structured photosensitive developing resins of examples 1-5
As can be seen from Table 1, the photosensitive developing resin with imide structure of the present invention has excellent photosensitivity, etching resistance, electroplating resistance, film stripping property, etc., and is suitable for preparing IC carrier plates.
The above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above examples, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present invention should be made in the equivalent manner, and the embodiments are included in the protection scope of the present invention.
Claims (10)
1. The imide structure photosensitive developing resin is characterized by comprising the following raw materials in parts by weight: 2-6 parts of polyamine, 6-20 parts of dicarboxylic anhydride, 1-6 parts of unsaturated monobasic acid, 0.02-0.08 part of polymerization inhibitor, 0.02-0.08 part of catalyst, 2-10 parts of hydrogen peroxide, 2-6 parts of saturated sodium bicarbonate solution, 1-5 parts of diethyl ether, 3-10 parts of formic acid, 50-70 parts of N-methylpyrrolidone and 2-8 parts of anhydrous zinc acetate.
2. The imide structure photosensitive developing resin of claim 1, wherein the polyamine is selected from one or more of 4,4 '-diaminodicyclohexylmethane, 1, 4-cyclohexanedimethylamine, 1, 3-cyclohexanedimethylamine, 4' - (p-dimethylamino) diphenylmethane, isophorone diamine, 1, 8-octanediamine, polyoxyethylene diamine, 2,4, 6-triaminopyrimidine.
3. The imide-structured photosensitive developing resin according to claim 1 or 2, wherein the dicarboxylic acid anhydride is selected from one or more of tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride; the unsaturated monoacid is selected from one or more of acrylic acid, methacrylic acid and butenoic acid.
4. The imide-structured photosensitive developing resin according to claim 1 or 2, wherein the polymerization inhibitor is selected from at least one of hydroquinone, p-t-butylcatechol, catechol; the catalyst is selected from one or more of benzyl triethyl ammonium chloride, benzyl diamine, triethylamine, diethylamine and triphenylphosphine.
5. The method for producing an imide-structured photosensitive developing resin as claimed in any one of claims 1 to 4, comprising the steps of:
s1, mixing dicarboxylic anhydride accounting for 40-60% of the total dicarboxylic anhydride, polyamine, anhydrous zinc acetate, polymerization inhibitor accounting for 20-30% of the total polymerization inhibitor and N-methylpyrrolidone, heating to 70-80 ℃ in a nitrogen atmosphere, stirring for 0.5-2h, then heating to 140-160 ℃, continuously stirring for 15-18 h, cooling the reaction solution to 20-35 ℃ after the reaction is finished, filtering, washing with absolute ethyl alcohol, drying and grinding the product to obtain bismaleimide solid powder;
s2, mixing the bismaleimide solid powder prepared in the step S1 with formic acid, stirring for 1-3 hours at 50-60 ℃, then adding hydrogen peroxide, continuing to react for 3-5 hours, adding saturated sodium bicarbonate solution and diethyl ether into a reaction product after the reaction is completed, shaking uniformly, standing for layering, separating an organic layer, washing the organic layer with water for 2-3 times, removing diethyl ether by rotary evaporation, adding anhydrous magnesium sulfate, drying overnight, and filtering to remove magnesium sulfate to obtain a product;
s3, mixing the product obtained in the step S2 with the rest of polymerization inhibitor and catalyst, heating the system to 90-100 ℃, then adding unsaturated monobasic acid, heating to 110-120 ℃ after the addition, continuing to react for 2-3h, cooling the temperature of the reaction system to 70-90 ℃ after the reaction is completed, then adding the rest of dicarboxylic anhydride, and reacting for 6-8h to obtain the catalyst.
6. The method for producing an imide-structured photosensitive developing resin as claimed in claim 5, wherein in step S2, hydrogen peroxide is slowly added dropwise with the time of addition being controlled to be 2 to 4 hours.
7. The method for producing an imide-structured photosensitive developing resin as claimed in claim 5 or 6, wherein the rotational speed of stirring is 600 to 800rpm.
8. Use of the imide structure photosensitive developing resin according to any one of claims 1-4 in the preparation of IC carrier board solder resist ink, printed circuit board solder resist ink or chip photoresist.
9. A dry film obtained by photo-curing or thermosetting the imide-structured photosensitive developing resin described in any one of claims 1 to 4.
10. Use of the dry film of claim 9 for the preparation of an IC carrier board or a printed circuit board.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310708449.2A CN116751152A (en) | 2023-06-14 | 2023-06-14 | Imide structure photosensitive developing resin and preparation method and application thereof |
| PCT/CN2024/096221 WO2024255602A1 (en) | 2023-06-14 | 2024-05-30 | Photosensitive developing resin having imide structure, preparation method therefor, and use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310708449.2A CN116751152A (en) | 2023-06-14 | 2023-06-14 | Imide structure photosensitive developing resin and preparation method and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116751152A true CN116751152A (en) | 2023-09-15 |
Family
ID=87949121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310708449.2A Pending CN116751152A (en) | 2023-06-14 | 2023-06-14 | Imide structure photosensitive developing resin and preparation method and application thereof |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN116751152A (en) |
| WO (1) | WO2024255602A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024255602A1 (en) * | 2023-06-14 | 2024-12-19 | 广东三求光固材料股份有限公司 | Photosensitive developing resin having imide structure, preparation method therefor, and use thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE59403359D1 (en) * | 1993-05-14 | 1997-08-21 | Ocg Microelectronic Materials | Process for the production of relief structures by i-line radiation |
| JPH07118368A (en) * | 1993-10-27 | 1995-05-09 | Nippon Kayaku Co Ltd | Resin composition, resist ink composition and cured product thereof |
| JP3931370B2 (en) * | 1997-03-04 | 2007-06-13 | 日立化成工業株式会社 | Photosensitive resin composition |
| CN103145988B (en) * | 2013-02-28 | 2014-11-05 | 中山大学 | Polyimide oligomer and liquid photoimagable solder resist ink |
| CN110673441B (en) * | 2019-11-11 | 2023-05-26 | 新东方油墨有限公司 | Photosensitive solder resist resin and preparation method thereof |
| CN116751152A (en) * | 2023-06-14 | 2023-09-15 | 广东三求光固材料股份有限公司 | Imide structure photosensitive developing resin and preparation method and application thereof |
-
2023
- 2023-06-14 CN CN202310708449.2A patent/CN116751152A/en active Pending
-
2024
- 2024-05-30 WO PCT/CN2024/096221 patent/WO2024255602A1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024255602A1 (en) * | 2023-06-14 | 2024-12-19 | 广东三求光固材料股份有限公司 | Photosensitive developing resin having imide structure, preparation method therefor, and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2024255602A1 (en) | 2024-12-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN114456205B (en) | Triazole-based silane coupling agent and preparation method and application thereof | |
| CN105301906B (en) | Positive photosensitive polyimide resin composition | |
| CN103145988B (en) | Polyimide oligomer and liquid photoimagable solder resist ink | |
| JP7261836B2 (en) | Modified maleimide compounds, methods of preparation and uses thereof | |
| CN114450350A (en) | Resin composition, resin composition film, cured film, hollow structure using the same, and semiconductor device | |
| CN116751152A (en) | Imide structure photosensitive developing resin and preparation method and application thereof | |
| CN114280887A (en) | Negative photosensitive solid glue film developed by alkaline water system and preparation method thereof | |
| TW202134348A (en) | Resin composition, resin sheet, multilayer printed wiring board, and semiconductor device | |
| CN114755883A (en) | Photosensitive resin composition, and preparation method and application thereof | |
| CN115160569A (en) | Photosensitive polyamic acid ester resin, resin composition and electronic component | |
| CN114536905B (en) | Epoxy glass cloth-based copper-clad plate and preparation method thereof | |
| TW202301027A (en) | Resin composition, resin sheet, multilayer printed wiring board, and semiconductor device | |
| KR100411757B1 (en) | Photosensitive resin composition and semiconductor apparatus using the same | |
| CN109627440B (en) | Soluble polyimide-based resin polymer material and application thereof | |
| JP4033426B2 (en) | Photosensitive resin composition | |
| CN109880091A (en) | A kind of semi-aromatic thermosetting polyimide resin and its preparation method and use | |
| TWI742945B (en) | Low-dissipation flexible copper-coated laminate, manufacturing method thereof, and electronic device | |
| JP4258690B2 (en) | Photosensitive resin composition | |
| CN115872869A (en) | Star alicyclic structure photosensitive alkali developing resin and preparation method and application thereof | |
| CN118373967B (en) | Glycerol carbonate modified epoxy resin and preparation method and application thereof | |
| CN118771994B (en) | A fluorine-containing diamine and a photosensitive resin composition | |
| CN116685050B (en) | Manufacturing method of PCB | |
| CN116178890B (en) | Thermosetting resin composition, prepreg for PCB and copper clad laminate for PCB | |
| CN117430812B (en) | Photosensitive polyamic acid ester resin, resin composition and application | |
| CN116954022B (en) | Chip carrier plate photosensitive solder resist dry film and forming method thereof |
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 |