Three-dimensional dye, manufacturing method of three-dimensional dye and photoresist mixture

Patent metadata

Field	Value
Publication number	US-11965101-B2
Application number	US-202017251872-A
Country	US
Kind code	B2
Filing date	Sep 3, 2020
Priority date	Aug 11, 2020
Publication date	Apr 23, 2024
Grant date	Apr 23, 2024

Abstract

A three-dimensional dye, a manufacturing method of the three-dimensional dye, and a photoresist mixture are disclosed. A non-planar three-dimensional dye molecular structure is constructed by adding a three-dimensional structure group into a dye molecule, thereby breaking the strong attraction force between the planar conjugation of the dye molecule. Aggregation of dye molecules are prevented, influence of dye molecules on optical paths is eliminated, and thus optical properties and color rendering properties of color filters made by a photoresist liquid are improved.

First claim

What is claimed is:

1. A three-dimensional dye, wherein a structural formula of the three-dimensional dye is R a -R b , wherein a structural formula of the R a group is

and a structural formula of the R b group is any one of

wherein M is any one of Zn, Cu, Ni, Co, or Fe, and R 1 group, R 2 group, R 3 group and R 4 group are each any one of halogen group, ketone group, aldehyde group, carboxyl group, alkyl group, sulfonate group, or nitrate group.

2. The three-dimensional dye according to claim 1 , wherein a structural formula of the R 4 group is any one of

3. The three-dimensional dye according to claim 1 , wherein the structural formula of the R a group is any one

wherein M is any one of Zn, Cu, Ni, Co, or Fe.

4. A manufacturing method of a three-dimensional dye, comprising steps of:
providing a first reactant, the first reactant is a compound comprising an R a group, a structural formula of the R a group comprises

 wherein R 1 group, R 2 group, and R 3 group are each any one of halogen group, ketone group, aldehyde group, carboxyl group, alkyl group, sulfonate group, or nitrate group, and wherein M is any one of Zn, Cu, Ni, Co, or Fe;
providing a second reactant, the second reactant is a compound comprising an R b group, a structural formula of the R b group comprises any one of

 wherein R 4 group is any one of halogen group, ketone group, aldehyde group, carboxyl group, alkyl group, sulfonate group, or nitrate group; and
reacting the first reactant with the second reactant to produce a three-dimensional dye, wherein a structure: formula of the three-dimensional dye is R a -R b .

5. The manufacturing method of the three-dimensional dye according to claim 4 , wherein the step of providing the first reactant further comprises:
providing a first precursor, wherein the first precursor is reacted to obtain the first reactant; and
wherein a structural formula of the first precursor is

6. The manufacturing method of the three-dimensional dye according to claim 5 , wherein the first precursor is reacted in a first solvent having a first additive to obtain the first reactant; wherein the first solvent comprises one of ester solvent, ether solvent, halogenated hydrocarbon solvent, alcohol solvent, amide solvent, halogenated alkane solvent, or a combination thereof, and the first additive comprises phosphorous chloride.

7. The manufacturing method of the three-dimensional dye according to claim 6 , wherein a structural formula of the first precursor is

the first solvent is N,N-dimethylformamide (DMF), and the first additive is phosphorus oxychloride.

8. The manufacturing method of the three-dimensional dye according to claim 4 , wherein the step of providing the second reactant further comprises:
providing a second precursor, wherein the second precursor is reacted to obtain the second reactant;
wherein a structural formula of the second precursor is

9. The manufacturing method of the three-dimensional dye according to claim 8 , wherein the second precursor is reacted in a second solvent having a second additive to produce the second reactant; wherein the second precursor is reacted in a second solvent having a second additive to obtain the second reactant; wherein the second solvent comprises one of ester solvent, ether solvent, halogenated hydrocarbon solvent, alcohol solvent, amide solvent, halogenated alkane solvent, or a combination thereof, and the second additive comprises One of phosphorous chloride, borohydride, phosphorus compound, or a combination thereof.

10. The manufacturing method of the three-dimensional dye according to claim 9 , wherein the second additive comprises any one of phosphorus oxychloride, sodium borohydride, triphenylphosphine dibromide, or a combination thereof.

11. The manufacturing method of the three-dimensional dye according to claim 10 , wherein the structural formula of the second precursor is

12. The manufacturing method of the three-dimensional dye according to claim 4 , wherein the first reactant and the second reactant are reacted in a third solvent having a catalyst to obtain the third reactant; wherein the third solvent comprises one of ester solvent, ether solvent, halogenated hydrocarbon solvent, alcohol solvent, amide solvent, halogenated alkane solvent, or a combination thereof, and the catalyst comprises a basic type catalyst.

13. The manufacturing method of the three-dimensional dye according to claim 12 , wherein the third solvent is chloroform, and the catalyst is 1,8-diazabicycloundec-7-ene.

14. A photoresist mixture, comprising: a three-dimensional dye, an adhesive resin, a photoinitiator, a polymerizable monomer, a solvent, and an adjuvant, wherein a structural formula of the three-dimensional dye is R a -R b , wherein a structural formula of the R a group is

and a structural formula of the R b group is any one of

wherein M is any one of Zn, Cu, Ni, Co, or Fe, and R 1 group, R 2 group, R 3 group, and R 4 group are each any one of halogen group, ketone group, aldehyde group, carboxyl group, alkyl group, sulfonate group, or nitrate group.

15. The photoresist mixture according to claim 14 , wherein the structural formula of the R 4 group is any one of

16. The photoresist mixture according to claim 14 , wherein the structural formula of the R a group is any one of

or

wherein M is any one of Zn, Cu, Ni, Co, or Fe.

17. The photoresist mixture according to claim 14 , wherein a mass percentage of the three-dimensional dye is 10%46%, a mass percentage of the adhesive resin is 5%-8%, and a mass percentage of the photoinitiator is 0.2%46%, a mass percentage of the polymerizable monomer is 5%-8%, a mass percentage of the solvent is 70%-80%, and a mass percentage of the adjuvant is 0.1%-0.2%.

18. The photoresist mixture according to claim 14 , wherein the adhesive resin is acrylic resin, the photoinitiator is a benzophenone compound, and the polymerizable monomer is acrylate of polyhyd

Assignees

• Tcl China Star Optoelectronics Tech Co Ltd

Inventors

• Ai Lin
• Meng Hong

Classifications

• C09B47/16 Primary

  having alkyl radicals substituted by nitrogen atoms · CPC title

• G03F7/033

  the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers · CPC title

• G03F7/105 Primary

  having substances, e.g. indicators, for forming visible images · CPC title

• C09B47/12

  Obtaining compounds having alkyl radicals, or alkyl radicals substituted by hetero atoms, bound to the phthalocyanine skeleton · CPC title

• G03F7/004

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