Photosensitive resin composition containing a triazine compound and a pre-sensitized plate using the same, and photosensitive resin composition containing acridine and triazine compounds and a color filter and a pre-sensitized plate using the same

• US 6,010,824 A
• Filed: 07/08/1997
• Issued: 01/04/2000
• Est. Priority Date: 11/10/1992
• Status: Expired due to Fees

• Current Assignee: Tokyo OHKA Kogyo Company Limited
• Original Assignee: Tokyo OHKA Kogyo Company Limited
• Inventors: Ohta, Katsuyuki, Uchikawa, Kiyoshi, Iwai, Takeshi, Komano, Hiroshi, Aoyama, Toshimi
• Primary Examiner(s): Nguyen, Nam
• Assistant Examiner(s): VERSTEEG, STEVEN H
• Application Number:
  US08/889,566
• Time in Patent Office: 910 Days
• Field of Search: 430/281.1, 430/288.1, 430/915, 430/920, 430/925, 522/26, 522/63
• US Class Current: 430/281.1
• CPC Class Codes: G03F 7/029 Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
• CPC Class Codes: G03F 7/0295 Photolytic halogen compounds
• CPC Class Codes: Y10S 430/116 Redox or dye sensitizer
• CPC Class Codes: Y10S 430/121 Nitrogen in heterocyclic ring
• CPC Class Codes: Y10S 430/126 Halogen compound containing

Abstract

A photosensitive resin composition comprising a polymeric binder, an ethylenically unsaturated monomer and a photopolymerization initiator is disclosed. Also, a PS plate using the same is disclosed. The photopolymerization initiator comprises at least one compound selected from specific triazine compounds having a bromine atom on the substituted phenyl nucleus thereof and specific trihalomethyl-containing triazine compounds. The composition has high photosensitivity sufficient for exposure with an argon laser light and satisfactory developability. Additionally disclosed is a photosensitive resin composition comprising a polymeric binder, a monomer having an ethylenically unsaturated double bond and photopolymerization initiators including an acridine compound and a specific triazine compound. This second photosensitive resin composition has high sensitivity, high resolution and a wide development margin. Using this photosensitive resin composition, color filters and PS plates can be produced that have high sensitivity and resolution even to low-energy visible light and which assure high pattern reproducibility.

Claims

1. A photosensitive resin composition comprising a polymeric binder, a monomer having an ethylenically unsaturated double bond and photopolymerization initiators, said resin composition containing an acridine compound and at least one triazine compound represented by the following formulae (VII), (VIII) and (IX) as said photopolymerization initiators:

##STR13## wherein R⁹ and R¹⁰ each independently represents an alkyl group having 1 to 3 carbon atoms.

2. The photosensitive resin composition as claimed in claim 1, wherein said acridine compound is at least one compound selected from the group consisting of 9-phenylacridine, 1,7-bis(9-acridinyl)heptane, 1,5-bis(9-acridinyl)pentane and 1,3-bis(9-acridinyl)propane.

3. The photosensitive resin composition as claimed in claim 2, wherein said acridine compound is 9-phenylacridine.

4. The photosensitive resin composition as claimed in claim 1, wherein said triazine compound is at least one compound selected from the group consisting of 2-(3'"'"'-bromo-4'"'"'-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(3'"'"'-bromo-4'"'"'-ethoxyphenyl)-4,6-bis-(trichloromethyl)-s-triazine, 2-(3'"'"'-bromo-4'"'"',5'"'"'-methylenedioxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(3'"'"'-bromo-4'"'"'-methoxystyryl)-4,6-bis(trichloromethyl)-s-triazine and 2-(3'"'"'-bromo-4'"'"'-ethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine.

5. The photosensitive resin composition as claimed in claim 4, wherein said triazine compound is 2-(3'"'"'-bromo-4'"'"'-ethoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(3'"'"'-bromo-4'"'"',5'"'"'-methylenedioxyphenyl)-4,6-bis(trichloromethyl)-s-triazine or 2-(3'"'"'-bromo-4'"'"'-ethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine.

6. The photosensitive resin composition as claimed in claim 1, wherein the compositional ratio by weight of said acridine compound to said triazine compound ranges from 1:

80 to 8;

1.

7. The photosensitive resin composition as claimed in claim 6, wherein the compositional ratio by weight of said acridine compound to said triazine compound ranges from 1:

10 to 2;

1.

8. The photosensitive resin composition as claimed in claim 1, wherein the content of said photopolymerization initiators ranges from 1 to 40 parts by weight per 100 parts by weight of the solids content in said photosensitive resin composition.

9. The photosensitive resin composition as claimed in claim 1, which contains 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butane-1-one as an additional photopolymerization initiator.

10. The photosensitive resin composition as claimed in claim 9, wherein the compositional ratio by weight between said 2-benzyl-2-dimethylamino-1-(4-morpholino-phenyl)-butane-1-one, said acridine compound and said triazine compound is 1:

(0.05-2);

(0.25-4).

11. The photosensitive resin composition as claimed in claim 10, wherein the compositional ratio by weight between said 2-benzyl-2-dimethylamino-1-(4-morpholino-phenyl)-butane-1-one, said acridine compound and said triazine compound is 1:

(0.2-1);

(0.5-2).

12. The photosensitive resin composition as claimed in claim 9, which contains 2-(o-chlorophenyl)-4,5-diphenylimidazolyl dimer as an additional photopolymerization initiator.

13. The photosensitive resin composition as claimed in claim 12, wherein the content of said 2-(o-chlorophenyl)-4,5-diphenylimidazolyl dimer ranges from 0.05 to 2 parts by weight per part by weight of said triazine compound.

14. The photosensitive resin composition as claimed in claim 1, which contains 2-(o-chlorophenyl)-4,5-diphenylimidazolyl dimer as an additional photopolymerization initiator.

15. The photosensitive resin composition as claimed in claim 14, wherein the content of said 2-(o-chlorophenyl)-4,5-diphenylimidazolyl dimer ranges from 0.05 to 2 parts by weight of said triazine compound.

16. The photosensitive resin composition as claimed in claim 1, which contains a titanocene compound as an additional photopolymerization initiator.

17. The photosensitive resin composition as claimed in claim 16, wherein said titanocene compound is represented by the following formula (XIV):

##STR14##

18. The photosensitive resin composition as claimed in claim 1, which further contains a pigment.

19. The photosensitive resin composition as claimed in claim 1, which further contains 3-methoxybutyl acetate or 3-methyl-3-methoxybutyl acetate as a solvent component.

20. The photosensitive resin composition as claimed in claim 1, wherein the ethylenically unsaturated monomer is a polyfunctional monomer having functional groups.

21. The photosensitive resin composition as claimed in claim 1, wherein the triazine compound is used in a total amount of from 0.1 to 15 parts by weight based on 100 parts of the total solids content of the photosensitive resin composition.

22. The photosensitive resin composition as claimed in claim 1, wherein at least one additive selected from the group consisting of fine metal particles, fine metal oxide particles and fine plastic particles is added to the photosensitive resin composition in an amount of from 1 to 40 parts by weight per 100 parts by weight of the total solids content of the photosensitive resin composition.

23. The photosensitive resin composition as claimed in claim 1, wherein the polymeric binder is used in an amount of from 10 to 60 parts by weight, the ethylenically unsaturated monomer is used in an amount of from 20 to 70 parts by weight, and the photopolymerization initiator is used in an amount of from 0.1 to 30 parts by weight each based on 100 parts by weight of the total solids content of the photosensitive resin composition.

24. The photosensitive resin composition as claimed in claim 1, wherein alkylene glycol monoalkyl ether, alkylene glycol dialkyl ether, ketone, alcohol, or carboxylic acid ester is added as a solvent to the photosensitive resin composition.