Color resist material, filter, and preparation method thereof

Patent metadata

Field	Value
Publication number	US-11732137-B2
Application number	US-202016768672-A
Country	US
Kind code	B2
Filing date	Apr 8, 2020
Priority date	Mar 24, 2020
Publication date	Aug 22, 2023
Grant date	Aug 22, 2023

Abstract

The present application discloses a color resist material, a filter, and a preparation method thereof. The color resist material is a trimer structure formed by polymerizing phthalocyanine dyes, wherein groups with double bonds are introduced on the phthalocyanine dyes to construct a three-molecule complex by a complexing agent, and the phthalocyanine dyes are connected by the double bonds to form a trimer structure. The color resist material with the trimer structure is stably stored in a photoresist liquid and has excellent solvent resistance, while maintains good solubility. Accordingly, a filter made of the color resist material has high transmittance and good optical performance.

First claim

What is claimed is:

1. A color resist material, having a chemical structure represented by Formula (1):

wherein each of chemical structures U 1 , U 2 and U 3 is represented by Formula (1-2):

wherein Z has an end connected to oxygen and another end connected to a double bond in Formula (1), Z is selected from alkylene and —YOX—, where X is selected from alkylene, and Y is selected from arylene, and
wherein in Formula (1), a benzene ring is also connected with other functional groups, each of the other functional groups is independently selected from one of hydrogen, halogen, alkyl, alkoxy, aryl, aryloxy, and a heterocyclic group, and M represents a metal or a metal halide.

2. The color resist material according to claim 1 , wherein U 1 has a chemical structure represented by Formula (2) or (3), U 2 has a chemical structure represented by Formula (4) or (5), and U 3 has a chemical structure represented by Formula (6) or (7):

wherein each of R 1 to R 36 is independently selected from one of hydrogen, halogen, alkyl, alkoxy, aryl, aryloxy, and a heterocyclic group.

3. The color resist material according to claim 1 , wherein Z is selected from one of alkylene having 2 to 8 carbons and —YOX—, where X is selected from alkylene having 1 to 3 carbons, and Y is selected from arylene having 12 to 24 carbons.

4. The color resist material according to claim 1 , wherein the arylene is a substituted or unsubstituted phenylene, naphthylene, or biphenylene.

5. The color resist material according to claim 1 , wherein the arylene contains —O—R as a substituent, and R is selected from one of the following groups:

6. The color resist material according to claim 1 , wherein each of the other functional groups is independently selected from one of halogen, alkyl having 1 to 8 carbons, alkoxy having 1 to 8 carbons, aryl having 6 to 12 carbons, aryloxy having 6 to 12 carbons, and a heterocyclic group having 3 to 12 carbons.

7. The color resist material according to claim 2 , wherein at least four of R 1 , R 3 , R 4 , R 6 , R 7 , R 9 , R 10 , R 12 , at least four of R 13 , R 15 , R 16 , R 18 , R 19 , R 21 , R 22 , R 24 , and at least four of R 25 , R 27 , R 28 , R 30 , R 31 , R 33 , R 34 , R 36 are selected from halogen, alkyl having 1 to 8 carbons, alkoxy having 1 to 8 carbons, aryl having 6 to 12 carbons, aryloxy having 6 to 12 carbons, and a heterocyclic group having 3 to 12 carbons.

8. A filter, comprising the color resist material according to claim 1 .

9. The filter according to claim 8 , wherein U 1 has a chemical structure represented by Formula (2) or (3), U 2 has a chemical structure represented by Formula (4) or (5), and U 3 has a chemical structure represented by Formula (6) or (7):

wherein each of R 1 to R 36 is independently selected from one of hydrogen, halogen, alkyl, alkoxy, aryl, aryloxy, and a heterocyclic group.

10. The filter according to claim 8 , wherein Z is selected from one of alkylene having 2 to 8 carbons and —YOX—, where X is selected from alkylene having 1 to 3 carbons, and Y is selected from arylene having 12 to 24 carbons.

11. The filter according to claim 8 , wherein the arylene is a substituted or unsubstituted phenylene, naphthylene, or biphenylene.

12. The filter according to claim 8 , wherein the arylene contains —O—R as a substituent, and R is selected from one of the following groups:

13. A method of preparing a color resist material, which comprises the following steps:
dissolving a phthalocyanine dye represented by one of Formula (8), Formula (9), and Formula (10) in a first solvent;
adding tripyridyltriazine to the first solvent, followed by stirring and then standing still to obtain a phthalocyanine complex having a chemical structure of Formula (11);
dissolving the phthalocyanine complex in a second solvent, and adding a catalyst to the second solvent for reaction;
performing quenching, extraction, and separation and purification by column chromatography, to obtain a phthalocyanine trimer of chemical structure (12); and
eluting the phthalocyanine trimer to obtain the color resist material having a chemical structure represented by Formula (1):

wherein each of chemical structures U 1 , U 2 and U 3 is represented by Formula (1-2):

wherein Z has an end connected to oxygen and another end connected to a double bond in Formula (1), Z is selected from alkylene and —YOX—, where X is selected from alkylene, and Y is selected from arylene,
wherein in Formula (1), a benzene ring is also connected with other functional groups, each of the other functional groups is independently selected from one of hydrogen, halogen, alkyl, alkoxy, aryl, aryloxy, and a heterocyclic group, and M represents a metal or a metal halide;
wherein one of Q 1 to Q 4 , one of Q 5 to Q 8 , one of Q 9 to Q 12 , one of Q 13 to Q 16 , one of Q 17 to Q 20 , one of Q 21 to Q 24 , one of Q 25 to Q 28 , one of Q 29 to Q 32 , one of Q 33 to Q 36 , one of Q 37 to Q 40 , one of Q 41 to Q 44 , and one of Q 45 to Q 48 are selected from —O—Z—CH═CH 2 , where Z is selected from one of alkylene and —YOX—, in which X is selected from alkylene, and Y is selected from arylene; each functional group Q 1 to Q 48 is independently selected from one of hydrogen, halogen, alkyl, alkoxy, aryl, aryloxy, and a heterocyclic group; and
wherein M is selected from a metal or a metal halide.

14. The preparation method according to claim 13 , further comprising a step of preparing the phthalocyanine dye represented by one of Formula (8), Formula (9), and Formula (10).

15. The preparation method according to claim 13 , wherein one of Q 2 and Q 3 , one of Q 6 and Q 7 , one of Q 10 and Q 11 , one of Q 14 and Q 15 , one of Q 18 and Q 19 , one of Q 22 and Q 23 , one of Q 26 and Q 27 , one of Q 30 and Q 31 , one of Q 34 and Q 35 , one of Q 38 and Q 39 , one of Q 42 and Q 43 , and one of Q 46 and Q 47 are selected from —O—Z—CH═CH 2 .

16. The preparation method according to claim 13 , wherein Z is selected from alkylenes having 2 to 8 carbons and —YOX—, where X is selected from alkylene having 1 to 3 carbons, and Y is selected from arylene having 12 to 24 carbons.

17. The preparatio

Assignees

• Tcl China Star Optoelectronics Tech Co Ltd

Inventors

• Al Lin
• Chen Hsiaohsien

Classifications

• C09B69/108 Primary

  containing a phthalocyanine dye · CPC title

• C09B47/085

  substituting the central metal atom · CPC title

• C09B47/18

  Obtaining compounds having oxygen atoms directly bound to the phthalocyanine skeleton · CPC title

• G02B1/04 Primary

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title

• G02F2202/04

  dye · CPC title