Photosensitive resin composition and photosensitive material comprising the same

Patent metadata

Field	Value
Publication number	US-9733563-B2
Application number	US-201213353066-A
Country	US
Kind code	B2
Filing date	Jan 18, 2012
Priority date	Jan 18, 2011
Publication date	Aug 15, 2017
Grant date	Aug 15, 2017

Abstract

The present invention relates to a photosensitive resin composition and a photosensitive material comprising the same. The photosensitive resin composition according to an exemplary embodiment of the present invention may comprise two multi-functional monomers where structures of side chains comprising unsaturated double bonds are different from each other while a composition ratio is changed. Accordingly, in the exemplary embodiment of the present invention, processability is excellent, and it is possible to decrease defects by a rupture when a LCD substrate is sealed and substrate separation defects due to an impact to the LCD products by improving an adhesion property to a lower substrate after a hard baking process.

First claim

What is claimed is:

1. A photosensitive resin composition, comprising:
an alkali-soluble binder resin,
a first monomer,
a second monomer,
a photoinitiator,
a solvent, and
adhesion promoting agents,
wherein the first monomer is represented by the following Formula 1 or Formula 2 and the second monomer is represented by the following Formula 5 or Formula 6 or is selected from the group consisting of pentaerythritol tetramethacrylate, pentaerythritol trimethacrylate, dipentaerythritol pentamethacrylate and dipentaerythritol hexamethacrylate,
wherein the photoinitiator comprises a photocrosslinking sensitizer or a curing promoter,
wherein the photocrosslinking sensitizer is selected from the group consisting of benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoylbenzoate, 3,3-dimethyl-4-methoxybenzophenone, 3,3,4,4-tetra(t-butylperoxycarbonyl)benzophenone, 9-fluorenone, 2-chloro-9-fluorenone, 2-methyl-9-fluorenone, thioxantone, 2,4-diethyl thioxantone, 2-chloro thioxantone, 1 -chloro-4-propyloxy thioxantone, isopropylthioxantone, diisopropylthioxantone, xantone, 2-methylxantone, anthraquinone, 2-methyl anthraquinone, 2-ethyl anthraquinone, t-butyl anthraquinone, 2,6-dichloro-9,10- anthraquinone, 9-phenylacridine, 1,7-bis(9-acridinyl)heptane, 1,5-bis(9-acridinylpentane), 1,3-bis(9-acridinyl)propane, benzyl, 1,7,7-trimethyl-bicyclo2,2,1 heptane-2,3 -dione, 9,10-penanthrenequinone, 2,4,6-trimethylbenzoyl diphenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4- trimethylpentyl phosphine oxide, methyl-4-(dimethylamino)benzoate, ethyl-4-(dimethylamino)benzoate, 2-n-butoxyethyl-4-(dimethylamino)benzoate, 2,5-bis(4-diethylaminobenzale)cyclopentanone, 2,6-bis(4-diethylaminobenzale)cyclohexanone, 2,6-bis(4-diethylaminobenzale)-4-methyl-cyclopentanone, 3,3-carbonylvinyl-7-(diethylamino)coumarine, 3-(2-benzothiazolyl)-7-(diethylamino)coumarine, 3-benzoyl-7-(diethylamino)coumarine, 3 -benzoyl-7-methoxy-coumarine, 10,10-carbonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H—C1]-benzopyrano [6,7,8 -ij]-quinolizine-11-one, 4-diethylamino chalcone, 4-azidebenzaleacetophenone, 2-benzoylmethylene, and 3-methyl-b-naphthothiazoline,
wherein the curing promoter is selected from the group consisting of 2-mercaptobenzoimidazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis(3-mercaptopropionate), pentaerythritol-tris(3 -mercaptopropionate), pentaerythritol-tetrakis(2-mercaptoacetate), pentaerythritol-tris(3-mercaptopropionate), pentaerythritol-tetrakis(2-mercaptoacetate), pentaerythritol-tris(2-mercaptoacetate), and trimethylolpropane-tris(2-mercaptoacetate), and trimethylolpropane-tris(3-mercaptopropionate),
wherein the solvent comprises three or more selected from the group consisting of a first solvent having a boiling point in the range of 140 to 159° C., a second solvent having a boiling point in the range of 160 to 179 ° C., and a third solvent having a boiling point in the range of 180 to 280° C.,
wherein an average boiling point of the total solvent in the range of 140 to 170° C.,
wherein the alkali-soluble binder is represented by the following Formula 7, and
wherein the adhesion promoting agents are methaacryloxypropyltrimethoxysilane and octadecyltrimethoxy silane,

wherein
at least one of R 1 to R 4 and at least one of R 6 to R 11 are represented by the following Formula 3, and remains are each independently hydrogen, a halogen group, or represented by the following Formula 4,

wherein
R 12 is an alkyleneoxide group or 6 -hexanoate group, and
m is 1 to 18,

wherein
at least two of R 13 to R 16 and at least two of R 17 to R 22 are represented by Formula 4 , and remains are each independently hydrogen or a halogen group, and

wherein Rx is a structure that forms an ester bond by addition reacting pentanary cyclic carboxylic anhydride or diisocyanate, Ry is selected from hydrogen, acryloyl, and methacrylolyl and n is 3 to 8.

2. The photosensitive resin composition according to claim 1 , wherein a content of the first monomer is 30 to 70 wt% on the basis of a total weight of the first and second monomers.

3. The photosensitive resin composition according to claim 1 , wherein the second monomer comprises one or more selected from the group consisting of pentaerythritol tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

4. The photosensitive resin composition according to claim 1 , wherein a content of the first and second monomers is 1 to 10 wt% on the basis of a total weight of the photosensitive resin composition.

5. The photosensitive resin composition according to claim 1 , wherein a content of the alkali-soluble binder resin is 1 to 10 wt%, a content of the photoinitiator is 0.5 to 5 wt%, and a content of the solvent is 65 to 90 wt% on the basis of the total weight of the photosensitive resin composition.

6. The photosensitive resin composition according to claim 1 , further comprising:
a colorant.

7. The photosensitive resin composition according to claim 6 , wherein a content of the colorant is 5 to 20 wt% on the basis of a total weight of the photosensitive resin composition.

8. The photosensitive resin composition according to claim 1 , further comprising:
one or more additives selected from the group consisting of a dispersing agent, an antioxidant, a UV absorbing agent, a thermal polymerization inhibitor, and a leveling agent.

9. A photosensitive material formed by using a method of manufacturing a photosensitive material, comprising:
(1) coating the photosensitive resin composition according to claim 1 on a substrate, and
(2) exposing by light and developing the coated photosensitive resin composition.

10. The photosensitive material according to claim 9 , wherein the photosensitive material is selected from the group consisting of a pigment dispersed photosensitive material for manufacturing a color filter, a photosensitive material for forming a black matrix, a photosensitive material for forming an overcoat layer, a column spacer photosensitive material, and a photosensitive material for a printed circuit board.

11. A method of manufacturing a photosensitive material, comprising:
1) coating the photosensitive resin composition according to claim 1 on a substrate, and
2) exposing to light and developing the coated photosensitive resin composition.

Assignees

• Ji Ho Chan
• Kim Sunghyun
• Choi Dongchang
• Choi Kyung Soo
• Cha Geun Young
• Lee Sang Chul
• Lg Chemical Ltd

Inventors

• Ji Ho Chan
• Kim Sunghyun
• Choi Dongchang
• Choi Kyung Soo
• Cha Geun Young
• Lee Sang Chul

Classifications

• G03F7/0007 Primary

  Filters, e.g. additive colour filters; Components for display devices · CPC title

• G03F7/0048

  characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents · CPC title

• G03F7/027

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

• G03F7/032

  with binders · CPC title