Photosensitive resin composition, method for producing patterned cured film, semiconductor element and electronic device
View Patent ↗Disclosed is a photosensitive resin composition comprising (A) an alkali-soluble resin having a structural unit represented by the following formula (1), (B) a compound that generates an acid by light, (C) a thermal crosslinking agent, and (D) an acryl resin having a structural unit represented by the following formula (2): wherein R 1 represents a hydrogen atom or a methyl group; R 2 represents an alkyl group having 1 to 10 carbon atoms, or the like; and a represents an integer of 0 to 3, b represents an integer of 1 to 3, and the total of a and b is 5 or less, and wherein R 3 represents a hydrogen atom or a methyl group; and R 4 represents a hydroxyalkyl group having 2 to 20 carbon atoms.
1. A photosensitive resin composition, comprising:
(A) an alkali-soluble resin having a structural unit represented by the following formula (1):
wherein R 1 represents a hydrogen atom or a methyl group; R 2 represents an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms; and a represents an integer of 0 to 3, b represents an integer of 1 to 3, and a total of a and b is 5 or less;
(B) a compound that generates an acid by light;
(C) a thermal crosslinking agent; and
(D) an acryl resin having a structural unit represented by the following formula (2) and a structural unit represented by the following formula (3):
wherein R 3 represents a hydrogen atom or a methyl group; and R 4 represents a hydroxyalkyl group having 2 to 20 carbon atoms;
wherein R 5 represents a hydrogen atom or a methyl group; and R 6 represents a monovalent organic group having a primary, secondary or tertiary amino group wherein the photosensitive resin has a haze value of less than 7%.
2. The photosensitive resin composition according to claim 1 , wherein the (D) component is the acryl resin further having a structural unit represented by the following formula (4):
wherein R 7 represents a hydrogen atom or a methyl group; and R 8 represents an alkyl group having 4 to 20 carbon atoms.
3. The photosensitive resin composition according to claim 1 , wherein the (D) component is the acryl resin further having a structural unit represented by the following formula (5):
wherein R 9 represents a hydrogen atom or a methyl group.
4. The photosensitive resin composition according to claim 1 , wherein the (A) component is the alkali-soluble resin further having a structural unit represented by the following formula (6):
wherein R 10 represents a hydrogen atom or a methyl group; R 11 represents an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms; and c represents an integer of 0 to 3.
5. The photosensitive resin composition according to claim 1 , wherein the (A) component is the alkali-soluble resin further having a structural unit represented by the following formula (7):
wherein R 12 represents a hydrogen atom or a methyl group; and R 13 represents an alkyl group having 1 to 10 carbon atoms or a hydroxyalkyl group having 1 to 10 carbon atoms.
6. The photosensitive resin composition according to claim 1 , wherein the (B) component is an o-quinone diazide compound.
7. The photosensitive resin composition according to claim 1 , wherein the (C) component comprises a thermal crosslinking agent having an alkoxymethyl group; and the photosensitive resin composition further comprises (E) a phenolic low molecular weight compound.
8. The photosensitive resin composition according to claim 7 , wherein the (E) component is a phenolic low molecular weight compound represented by the following formula (13), (14) or (15):
wherein R 18 represents a hydrogen atom or a methyl group; and a1 to f1 represent an integer of 0 to 3, a total of d1 to f1 is 1 or more, a total of a1 and d1 is 5 or less, a total of b1 and e1 is 5 or less, and a total of c1 and f1 is 5 or less;
wherein R 19 represents a hydrogen atom or a methyl group; and a2 to c2 represent an integer of 0 to 3, d2 to f2 represent an integer of 1 to 3, a total of a2 and d2 is 5 or less, a total of b2 and e2 is 5 or less, and a total of c2 and f2 is 5 or less; or
wherein a3, c3, h and i represent an integer of 0 to 3, d3 and f3 represent an integer of 1 to 3, a total of a3 and d3 is 5 or less, a total of c3 and f3 is 5 or less, and a total of h and i is 4 or less.
9. A patterned cured film, being obtained by heating the photosensitive resin composition according to claim 1 .
10. A method for producing a patterned cured film, comprising:
a step of applying and drying the photosensitive resin composition according to claim 1 on a part or the whole of a substrate to thereby form a resin film;
a step of exposing a part or the whole of the resin film;
a step of developing the resin film after the exposure with an alkali aqueous solution to thereby form a patterned resin film; and
a step of heating the patterned resin film.
11. A semiconductor element, having a patterned cured film formed by the method for producing a patterned cured film according to claim 10 , as an interlayer insulating layer.
12. A semiconductor element, having a patterned cured film formed by the method for producing a patterned cured film according to claim 10 , as a surface protecting layer.
13. An electronic device, comprising the semiconductor element according to claim 11 .
14. A photosensitive resin composition, comprising:
(A) an alkali-soluble resin having a structural unit represented by the following formula (1):
wherein R 1 represents a hydrogen atom or a methyl group; R 2 represents an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms; and a represents an integer of 0 to 3, b represents an integer of 1 to 3, and a total of a and b is 5 or less;
(B) a compound that generates an acid by light;
(C) a thermal crosslinking agent; and
(D) an acryl resin having a structural unit represented by the following formula (2) and a structural unit represented by the following formula (4):
wherein R 3 represents a hydrogen atom or a methyl group; and R 4 represents a hydroxyalkyl group having 2 to 20 carbon atoms;
wherein R 7 represents a hydrogen atom or a methyl group; and R 8 represents an alkyl group having 4 to 20 carbon atoms wherein the photosensitive resin has a haze value of less than 7%.
15. The photosensitive resin composition according to claim 14 , wherein the (D) component is the acryl resin further having a structural unit represented by the following formula (5):
wherein R 9 represents a hydrogen atom or a methyl group.
16. The photosensitive resin composition according to claim 14 , wherein the (A) component is the alkali-soluble resin further having a structural unit represented by the following formula (6):
wherein R 10 represents a hydrogen atom or a methyl group; R 11 represents an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms; and c represents an integer of 0 to 3.
17. The photosensitive resin composition according to claim 14 , wherein the (A) component is the alkali-soluble resin further having a structural unit represented by the following formula (7):
wherein R 12 represents a hydrogen atom or a methyl group; and R 13 represents an alkyl group having 1 to 10 carbon atoms or a hydroxyalkyl group having 1 to 10 carbon atoms.
18. The photosensitive resin composition according to claim 14 , wherein the (B) component is an o-quinone diazide compound.
19. The photosensitive resin composition according to claim 14 , wherein the (C) component comprises a thermal crosslinking agent having an alkoxymethyl group; and the photosensitive resin composition further comprises (E) a phenolic low molecular weight compound.
20. The photosensitive resin composition according to claim 19 , wherein the (E) component is a phenolic low molecular weight compound represented by the following formula (13), (14) or (15):
wherein R 18 represents a hydrogen atom or a methyl group; and a1 to f1 represent an integer of 0 to 3, a total of d1 to f1 is 1 or more, a total of a1 and d1 is 5 or less, a total of b1 and e1 is 5 or less, and a total of c1 and f1 is 5 or less;
wherein R 19 represents a hydrogen atom or a methyl group; and a2 to c2 represent an integer of 0 to 3, d2 to f2 represent an integer of 1 to 3, a total of a2 and d2 is 5 or less, a total of b2 and e2 is 5 or less, and a total of c2 and f2 is 5 or less; or
wherein a3, c3, h and i represent an integer of 0 to 3, d3 and f3 represent an integer of 1 to 3, a total of a3 and d3 is 5 or less, a total of c3 and f3 is 5 or less, and a total of h and i is 4 or less.