Coloring agent dispersion, photosensitive resin composition, cured product, organic el element, method for forming pattern, and method for producing photosensitive resin composition

Patent metadata

Field	Value
Publication number	US-10416560-B2
Application number	US-201715791667-A
Country	US
Kind code	B2
Filing date	Oct 24, 2017
Priority date	Oct 25, 2016
Publication date	Sep 17, 2019
Grant date	Sep 17, 2019

Abstract

A coloring agent dispersion which contains a satisfactorily dispersed pigment, and results in a photosensitive resin composition capable of forming a cured film when mixed in the photosensitive resin composition; a photosensitive resin composition containing the coloring agent dispersion; a cured product of the composition; an organic EL element provided with the cured product; a method for forming a pattern using the composition; and a method for producing a photosensitive resin composition using the dispersion. In a coloring agent dispersion including a coloring agent which contains a pigment and a dispersant, a dispersant containing a silsesquioxane compound of a specific structure is used.

First claim

What is claimed is:

1. A coloring agent dispersion comprising a coloring agent (E), wherein the coloring agent (E) contains a pigment (E1) and a dispersant (E2),
a content of the pigment (E1) is 30% by mass or more and 95% by mass or less based on the mass of the total solid component of the coloring agent dispersion,
the dispersant (E2) contains a silsesquioxane compound including a constituent unit represented by the following formula (e2a):

wherein R e1 is a monovalent organic group, and
the silsesquioxane compound comprises at least one selected from the group consisting of an amide bond and a urethane bond.

2. The coloring agent dispersion according to claim 1 , wherein the Re1 includes at least one selected from the group consisting of an aromatic group, an amide bond, and a urethane bond.

3. The coloring agent dispersion according to claim 1 , wherein the R e1 is a group represented by the following formula (e2a-I):
—X e —B e —Y e —COOH  (e2a-I)

or a group represented by the following formula (e2a-II):
—Z e —A e   (e2a-II)

wherein X e is a single bond, an alkylene group having 1 or more and 6 or less carbon atoms, an arylene group having 6 or more and 12 or less carbon atoms, or a group represented by —R e6 —NH—R e7 —,
R e6 and R e7 each independently represent an alkylene group having 1 or more and 3 or less carbon atoms, Y e is a divalent cyclic organic group, or a straight-chain aliphatic hydrocarbon group having 1 to 20 carbon atoms, B e is —NH—CO—, —CO—NH—, —NH—CO—O—, —O—CO—NH—, or —NH—CO—NH—,
X e and Y e each independently may be substituted with one or more groups selected from the group consisting of a (meth)acryloyloxy group, a vinyl group, and an epoxy group-containing organic group,
Z e is a single bond, an alkylene group having 1 to 6 carbon atoms, or an arylene group having 6 or more and 12 or less carbon atoms, and
A e is a (meth)acryloyloxy group, a vinyl group, or an epoxy group-containing organic group, and wherein the silsesquioxane compound includes, as a constituent unit represented by the formula (e2a), a constituent unit (A) having a group represented by the formula (e2a-I) as the R e1 , and wherein in all of the constituent units (A) in the silsesquioxane compound, when the R e1 is not substituted with a (meth)acryloyloxy group, a vinyl group, or an epoxy group-containing organic group,
the silsesquioxane compound includes a constituent unit (B) which is represented by the formula (e2a) and has a group represented by the formula (e2c) as the R e1 .

4. The coloring agent dispersion according to claim 1 , wherein the amount of the dispersant (E2) is 5% by mass or more and 70% by mass or less based on the mass of the total solid component of the coloring agent dispersion.

5. The coloring agent dispersion according to claim 1 , wherein the pigment (E1) contains a light shielding agent.

6. A photosensitive resin composition comprising an alkali-soluble resin (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), and the coloring agent dispersion according to claim 1 .

7. The photosensitive resin composition according to claim 6 , wherein the content of the pigment (E1) is within a range of 5% by mass or more and 80% by mass or less based on the mass of the total solid component of the photosensitive resin composition.

8. The photosensitive resin composition according to claim 6 , wherein the alkali-soluble resin (A) contains a resin including a cardo skeleton.

9. The photosensitive resin composition according to claim 8 , wherein the resin including a cardo skeleton is a resin represented by the following formula (a-1):

Wherein X a represents a group represented by the following formula (a-2):

wherein R a1 each independently represent a hydrogen atom, a hydrocarbon atom having 1 or more and 6 or less carbon atoms, or a halogen atom, R a2 each independently represent a hydrogen atom or a methyl group, R a3 each independently represent a straight-chain or branched-chain alkylene group, m2 represents 0 or 1, and W a represents a group represented by the following formula (a-3):

Wherein a ring A represents an aliphatic ring which may be fused with an aromatic ring and may have a substituent, R a0 is a hydrogen atom or a group represented by —CO—Y a —COOH, Y a represents a divalent residue in which an acid anhydride group is eliminated from dicarboxylic anhydride, and Z a represents a tetravalent residue in which two acid anhydride groups are eliminated from tetracarboxylic dianhydride, and
wherein, in the formula (a-1), m1 represents an integer of 0 or more and 20 or less.

10. The photosensitive resin composition according to claim 6 , further comprising a polyfunctional crosslinkable compound (D) having plural epoxy groups or oxetanyl groups in one molecule, wherein
epoxy equivalent or oxetanyl equivalent of the polyfunctional crosslinkable compound (D) is 50 g/eq or more and 350 g/eq or less.

11. The photosensitive resin composition according to claim 10 , wherein the polyfunctional crosslinkable compound (D) contains an epoxy compound having two or more epoxy groups per one molecule.

12. A cured product obtained by curing the photosensitive resin composition according to claim 6 .

13. An organic electroluminescent (EL) element comprising the cured product according to claim 12 .

14. A method for forming a pattern, the method comprising:
applying the photosensitive resin composition according to claim 6 to form a coating film;
subjecting the coating film to regioselective exposure; and
developing the exposed coating film.

15. A method for producing the photosensitive resin composition according to claim 6 , the method comprising:
dispersing the pigment (E1) in a liquid in the presence of the dispersant (E2) to prepare the coloring agent dispersion; and
mixing the coloring agent dispersion, the alkali-soluble resin (A), the photopolymerizable monomer (B), and the photopolymerization initiator (C).

16. A coloring agent dispersion comprising a coloring agent (E), wherein
the coloring agent (E) comprises a pigment (E1) and a dispersant (E2),
the content of the pigment (E1) is 30% by mass or more and 95% by mass or less based on the mass of the total solid component of the coloring agent dispersion,
the dispersant (E2) contains a silsesquioxane compound including a constituent unit represented by the following formula (e2a):

wherein, in the formula (e2a), R e1 is a monovalent organic group, and
the dispersant (E2) does not include an acryl resin-based dispersant.

17. The coloring agent dispersion according to claim 1 , wherein the silsesquioxane compound does not comprise a (meth)acryloyloxy group.

18. The coloring agent dispersion according to claim 1 , wherein the silsesquioxane compound does not comprise an acryl resin-based constituent unit.

Assignees

• Tokyo Ohka Kogyo Co Ltd

Inventors

• Matsumoto naozumi
• Ohuchi Yasuhide
• Ishikawa Tatsuro
• Kuroko Mayumi
• Shiota Dai

Classifications

• G03F7/0007

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

• G03F7/26

  Processing photosensitive materials; Apparatus therefor (G03F7/12 - G03F7/24 take precedence) · CPC title

• C09B57/00

  Other synthetic dyes of known constitution · CPC title

• G03F7/038

  Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) · CPC title

• G03F7/027

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