IP Library Granted Patent US 11,573,490
Granted Patent B2
US 11,573,490 · App. 16/879,160 · Granted Feb 7, 2023

Positive-type photosensitive resin composition and cured film prepared therefrom

Inventors: Ji Ung Kim (Gyeonggi-do, KR); Geun Huh (Gyeonggi-do, KR); Ju-Young Jung (Gyeonggi-do, KR); JinKyu Im (Gyeonggi-do, KR); Yeonok Kim (Gyeonggi-do, KR)
G03F7/0226G03F7/027G03F7/0233G03F7/033G03F7/0757
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Quick Facts
Patent No.
US 11,573,490
App. No.
16/879,160
Granted
Feb 7, 2023
Kind
B2
Abstract

The present invention relates to a positive-type photosensitive resin composition and a cured film prepared therefrom. The positive-type photosensitive resin composition comprises a nonpolar organic solvent, thereby suppressing the reactivity of the epoxy group in the composition to reduce the production of diol compounds. When a cured film is prepared from the composition, an appropriate level of developability can be maintained to further enhance the pattern adhesiveness, resolution, and sensitivity. Further, since the composition of the present invention has a small difference in the film retention rates at room temperature and low temperatures, the composition may have stable stability over time.

Claims (30)

1. A positive-type photosensitive resin composition, which comprises:

(A) an acrylic copolymer;

(B) a siloxane copolymer;

(C) a 1,2-quinonediazide compound; and

(D) a solvent,

wherein the solvent (D) comprises a nonpolar organic solvent whose boiling point is 155 to 200° C. at 25° C. and 1 atm,

wherein the nonpolar organic solvent comprises a compound represented by the following Formula 4:

R 6 O(C m H 2m O) 2 R 7   [Formula 4]

in the above Formula 4, R 6 and R 7 are each independently hydrogen or C 1-4 alkyl, and m is 2 or 3,

wherein the solvent (D) comprises the nonpolar organic solvent in an amount of 1 to 30% by weight of based on the total weight of the solvent (D).

2. The positive-type photosensitive resin composition of claim 1 , wherein the acrylic copolymer (A) comprises (a-1) a structural unit derived from an ethylenically unsaturated carboxylic acid, an ethylenically unsaturated carboxylic anhydride, or a combination thereof; (a-2) a structural unit derived from an unsaturated compound containing an epoxy group; and (a-3) a structural unit derived from an ethylenically unsaturated compound different from the structural units (a-1) and (a-2).

3. The positive-type photosensitive resin composition of claim 2 , wherein the structural unit (a-3) comprises a structural unit (a-3-1) represented by the following Formula 1:

in the above Formula 1, R 1 is C 1-4 alkyl.

4. The positive-type photosensitive resin composition of claim 3 , wherein the structural unit (a-3) comprises a structural unit (a-3-2) represented by the following Formula 2:

in the above Formula 2, R 2 and R 3 are each independently C 1-4 alkyl.

5. The positive-type photosensitive resin composition of claim 4 , wherein the structural unit (a-3-1) and the structural unit (a-3-2) have a content ratio of 1:99 to 80:20.

6. The positive-type photosensitive resin composition of claim 1 , wherein the siloxane copolymer (B) comprises a structural unit derived from a silane compound represented by the following Formula 3:

(R 4 ) n Si(OR 5 ) 4-n   3

in the above Formula 3,

n is an integer of 0 to 3;

R 4 is each independently C 1-12 alkyl, C 2-10 alkenyl, C 6-15 aryl, C 3-12 heteroalkyl, C 4-10 heteroalkenyl, or C 6-15 heteroaryl; and

R 5 is each independently hydrogen, C 1-6 alkyl, C 2-6 acyl, or C 6-15 aryl,

wherein the heteroalkyl, the heteroalkenyl, and the heteroaryl groups each independently have at least one heteroatom selected from the group consisting of O, N, and S.

7. The positive-type photosensitive resin composition of claim 1 , which comprises the siloxane copolymer (B) in an amount of 20 to 80 parts by weight based on 100 parts by weight of the acrylic copolymer (A).

8. The positive-type photosensitive resin composition of claim 1 , wherein the nonpolar organic solvent comprises at least one selected from the group consisting of diethylene glycol monomethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl propyl ether, diethylene glycol methyl isopropyl ether, diethylene glycol methyl ethyl ether, dipropylene glycol methyl ether, and dipropylene glycol dimethyl ether.

9. The positive-type photosensitive resin composition of claim 1 , which further comprises a multifunctional monomer.

10. The positive-type photosensitive resin composition of claim 9 , wherein the multifunctional monomer is a tri- to octa-functional compound.

11. The positive-type photosensitive resin composition of claim 9 , wherein the multifunctional monomer comprises an ethylenically unsaturated double bond.

12. The positive-type photosensitive resin composition of claim 9 , which comprises the multifunctional monomer in an amount of 1 to 30 parts by weight based on 100 parts by weight of the acrylic copolymer (A).

13. The positive-type photosensitive resin composition of claim 1 , which further comprises an epoxy compound.

Assignments (2)
CHANGE OF NAME Recorded Oct 17, 2024
From: ROHM & HAAS ELECTRONIC MATERIALS KOREA LTD
To: DUPONT SPECIALTY MATERIALS KOREA LTD
Reel/Frame 069185/0438 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 21, 2022
From: KIM, JI UNG; HUH, GEUN; JUNG, JU-YOUNG; IM, JINKYU; KIM, YEONOK
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 062170/0791 →