Photosensitive resin composition, and polymer film made therefrom

Patent metadata

Field	Value
Publication number	US-10928730-B2
Application number	US-201816027327-A
Country	US
Kind code	B2
Filing date	Jul 4, 2018
Priority date	May 22, 2018
Publication date	Feb 23, 2021
Grant date	Feb 23, 2021

Abstract

A photosensitive resin composition comprises a modified polyimide polymer having a chemical structural formula of:

photosensitive monomers, a bisphenol A epoxy resin, a photo-initiator, and a pigment. The modified polyimide polymer is made by a reaction of a polyimide polymer having a chemical structural formula of:

and glycidyl methacrylate. The carboxyl group of the polyimide polymer reacts with the epoxy group of glycidyl methacrylate. The polyimide polymer is made by a reaction of dianhydride monomers each having an A group, diamine monomers each having the R group, diamine monomers each having the R 1 group, and diamine monomers each having the R 2 group. The diamine monomer having R group is a diamine compound having R group bonding with the carboxyl group. The diamine monomer having R 1 group is a soft long-chain diamine monomer. R 2 group comprises at least one secondary amine group or tertiary amine group.

First claim

What is claimed is:

1. A photosensitive resin composition comprising:
100 parts by weight of a modified polyimide polymer having a chemical structural formula of

10 parts to 40 parts by weight of photosensitive monomers;
10 parts to 25 parts by weight of a bisphenol-A epoxy resin having a chemical structural formula of

1 part to 10 parts by weight of a photo-initiator; and
1 part to 5 parts by weight of a coloring agent;
wherein the modified polyimide polymer is made by a reaction of a polyimide polymer having a chemical structural formula of

and glycidyl methacrylate, during the reaction, the carboxyl group bonded with R group of the polyimide polymer reacts with the epoxy group of glycidyl methacrylate; the polyimide polymer is made by a polymerization reaction of dianhydride monomers each having an A group, diamine monomers each having a R group, diamine monomers each having a R 1 group, and diamine monomers each having a R 2 group; the diamine monomer having R group is a diamine compound having R group bonded with the carboxyl group, the diamine monomer having R 1 group is a soft long-chain diamine monomer, R 2 group comprises at least one secondary amine group or tertiary amine group; a degree of polymerization x, a degree of polymerization y, and a degree of polymerization z each is a natural number greater than 1, the epoxy resin has an epoxy equivalent weight of about 180 g/Eq to about 2000 g/Eq, the dianhydride monomer having A group is selected from a group consisting of 4,4′-bis(phthalic anhydride)sulfide having a CAS number 25884-43-9, bis-(3-phthalyl anhydride) ether having a CAS number 1823-59-2, bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic acid dianhydride having a CAS number 1719-83-1, N,N′-(5,5′-(perfluoropro-pane-2,2-diyl) bis(2-hydroxy-5,1-phenylene))bis(1,3-dioxo-1,3-dihydroisobenzofuran-5-arboxamide) having a CAS number 223255-30-9, bicyclooctanetetracarboxylic dianhydride having a CAS number 2754-40-7, and any combination thereof; the diamine monomer having R group is selected from a group consisting of 5,5′-methylenebis(2-aminobenzoic acid), 3,5-diaminobenzoic acid, 1,3-bis(4-amino-2-carboxyphenoxy)benzene having a CAS number 1620566-43-9, 3,5-bis(4-Aminophenoxy)Benzoic acid, 5-amino-2-(4-aminophenoxy)benzoic acid having a CAS number 135209-70-0, N-bis(4-aminophenyl)-4-carboxylaniline having a CAS number 1071762-58-7, 3,5-diamino-4-methoxybenzoic acid having a CAS number 177960-30-4, 3,4-diaminobenzoic acid, and any combination thereof; the diamine monomer having R 1 group is selected from a group consisting of (3-aminopropyl)-terminated dimethylsiloxane having a CAS number 97917-34-5, triethylenetetramine, tetraethylenepentamine, polyetheramine having a CAS number 400760-04-5, 796093-55-5, 9046-10-0, or 9046-10-0, and any combination thereof.

2. The photosensitive resin composition of claim 1 , wherein the diamine monomer having R 2 group is selected from a group consisting of 4,4′-diamino-2′-methylbenzanilide having a CAS number 14303-59-4, 4-amino-N-(4-amino-2-methoxyphenyl)benzamide having a CAS number 14071-33-1, 1,4-bis-N,N′-(4′-aminophenyl)terephtalamide having a CAS number 34066-75-6, 4,4′-diaminobenzanilide having a CAS number 785-30-8, N,N′-bis(4-aminobenzoyl)-p-phenylenediamine having a CAS number 2362-26-7, 3-amino-N-(4-aminophenyl)benzamide having a CAS number 2657-93-4, and any combination thereof.

3. The photosensitive resin composition of claim 1 , wherein the modified polyimide polymer has a molar mass of about 5000 g/mol to about 20000 g/mol, the epoxy resin has an epoxy equivalent weight of about 180 g/Eq to about 2000 g/Eq.

4. The photosensitive resin composition of claim 1 , wherein the photosensitive monomer is an acrylate compound containing ethoxy groups.

5. The photosensitive resin composition of claim 4 , wherein the number of the ethoxy groups is greater than or equal to 10.

6. The photosensitive resin composition of claim 5 , wherein the photosensitive monomer is selected from at least one of polyethylene glycol di(meth)acrylate, ethoxylated 1,6-hexanediol diacrylate, ethoxylted bisphenyl fluorene diacrlate, ethoxylated bisphenol-A di(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, ethoxylated pentaerythritol tetraacrylate, ethoxylated dipentaerythritol hexaacrylate, and any combination thereof.

7. The photosensitive resin composition of claim 1 , wherein the photosensitive resin composition further comprises 5 parts to 30 parts of inorganic filler particles.

8. A polymer film made by curing a photosensitive resin composition, the photosensitive resin composition comprising:
100 parts by weight of a modified polyimide polymer having a chemical structural formula of

10 parts to 40 parts by weight of photosensitive monomers;
10 parts to 25 parts by weight of a bisphenol-A epoxy resin having a chemical structural formula of

1 part to 10 parts by weight of a photo-initiator; and
1 part to 5 parts by weight of a coloring agent;
wherein the modified polyimide polymer is made by a reaction of a polyimide polymer having a chemical structural formula of

and glycidyl methacrylate, during the reaction, the carboxyl group bonded with R group of the polyimide polymer reacts with the epoxy group of glycidyl methacrylate; the polyimide polymer is made by a polymerization reaction of dianhydride monomers each having an A group, diamine monomers each having a R group, diamine monomers each having a R 1 group, and diamine monomers each having a R 2 group; the diamine monomer having R group is a diamine compound having R group bonded with the carboxyl group, the diamine monomer having R 1 group is a soft long-chain diamine monomer, R 2 group comprises at least one secondary amine group or tertiary amine group; a degree of polymerization x, a degree of polymerization y, and a degree of polymerization z each is a natural number greater than 1, the epoxy resin has an epoxy equivalent weight of about 180 g/Eq to about 2000 g/Eq, the dianhydride monomer having A group is selected from a group consisting of 4,4′-bis(phthalic anhydride)sulfide having a CAS number 25884-43-9, bis-(3-phthalyl anhydride) ether having a CAS number 1823-59-2, bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic acid dianhydride having a CAS number 1719-83-1, N,N′-(5,5′-(perfluoropro-pane-2,2-diyl) bis(2-hydroxy-5,1-phenylene))bis(1,3-dioxo-1,3-dihydroisobenzofuran-5-arboxamide) having a CAS number 223255-30-9, bicyclooctanetetracarboxylic dianhydride having a CAS number 2754-40-7, and any combination thereof; the diamine monomer having R group is selected from a group consisting of 5,5′-methylenebis(2-aminobenzoic acid), 3,5-diaminobenzoic acid, 1,3-bis(4-amino-2-carboxyphenoxy)benzene having a CAS number 1620566-43-9, 3,5-bis(4-Aminophenoxy)Benzoic acid, 5-amino-2-(4-aminophenoxy)benzoic acid having a CAS number 135209-70-0, N-bis(4-aminophenyl)-4-carboxylaniline having a CAS number 1071762-58-7, 3,5-diamino-4-methoxybenzoic acid having a CAS number 177960-30-4, 3,4-diaminobenzoic acid, and any combination thereof; the diamine mono

Assignees

• Zhen Ding Tech Co Ltd

Inventors

• Yen Chen-Feng
• Hsiang Shou-Jui
• Wu Pei-Jung
• Su Szu-Hsiang

Classifications

• G03F7/004

  Photosensitive materials (G03F7/12, G03F7/14 take precedence) · CPC title

• G03F7/0387 Primary

  Polyamides or polyimides · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title

• G03F7/027

  Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence) · CPC title

• C08F2/50

  with sensitising agents · CPC title