IP Library Granted Patent US 9,417,522
Granted Patent B2
US 9,417,522 · App. 14/580,902 · Granted Aug 16, 2016

Photosensitive resin composition and method for producing resist pattern

Inventors: Hisanori Akimaru (Minato-ku, JP); Hirokazu Sakakibara (Minato-ku, JP); Hidefumi Ishikawa (Minato-ku, JP); Shingo Naruse (Minato-ku, JP)
Assignee: JSR CORPORATION
G03F7/031G03F7/027G03F7/0388G03F7/30
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Quick Facts
Patent No.
US 9,417,522
App. No.
14/580,902
Granted
Aug 16, 2016
Kind
B2
Abstract

The present invention provides a photosensitive resin composition comprising: an alkali-soluble resin (A); a compound having at least one ethylenically unsaturated double bond per molecule (B); a photo radical polymerization initiator having a keto oxime ester structure (C); and a compound represented by the Formula (1) or (2) below (D); wherein the content of the photo radical polymerization initiator (C) is 0.5 to 5 times the content of the compound (D), and the content of the photo radical polymerization initiator (C) with respect to 100 parts by mass of the compound (B) is 3 to 20 parts by mass. In Formula (1), the six R 1 s each independently represent a hydrogen atom or an electron-donating group, and n represents 0 or 1. In Formula (2), the six R 2 s each independently represent a hydrogen atom or an electron-donating group, and m represents 0 or 1. By use of the photosensitive resin composition of the present invention, formation of a resist pattern having excellent resolution is possible even without using an oxygen inhibition layer. By the method for producing a resist pattern of the present invention, formation of a resist pattern having excellent resolution is possible even without using an oxygen inhibition layer.

Claims (49)

1. A photosensitive resin composition, comprising:

(A) an alkali-soluble resin;

(B) a compound comprising an ethylenically unsaturated double bond per molecule;

(C) a photo radical polymerization initiator comprising a keto oxime ester structure; and

(D) a compound of Formula (1) or Formula (2):

wherein, in Formula (1):

each R 1 independently represents a hydrogen atom or an electron-donating group; and

n represents 0 or 1,

wherein, in Formula (2):

each R 2 independently represents a hydrogen atom or an electron-donating group; and

m represents 0 or 1,

wherein a content by mass of the photo radical polymerization initiator (C) is 0.5 to 5 times of a content by mass of the compound (D), and

wherein a content of the photo radical polymerization initiator (C) with respect to 100 parts by mass of the compound (B) is 4 to 12 parts by mass.

2. The photosensitive resin composition according to claim 1 , wherein the keto oxime ester structure of the photo radical polymerization initiator (C) is a structure represented by Formula (3):

3. A method for producing a resist pattern, the method comprising:

applying the photosensitive resin composition according to claim 2 to a base material to forma resin coating;

exposing the resin coating to obtain an exposed resin coating; and

developing the exposed resin coating using an alkaline developer to allow pattern formation.

4. The photosensitive resin composition according to claim 2 , wherein the keto oxime ester structure of the photo radical polymerization initiator (C) is bound to a pbenylcarbazole group.

5. A method for producing a resist pattern, the method comprising:

applying the photosensitive resin composition according to claim 1 to a base material to form a resin coating;

exposing the resin coating to obtain an exposed resin coating; and

developing the exposed resin coating using an alkaline developer to allow pattern formation.

6. The photosensitive resin composition according to claim 1 , wherein the content by mass of the photo radical polymerization initiator (C) is 0.6 to 4 times of the content by mass of the compound (D).

7. The photosensitive resin composition according to claim 1 , wherein the photo radical polymerization initiator (C) has formula (5):

8. The photosensitive resin composition according to claim 1 , wherein the photo radical polymerization initiator (C) has formula (6):

9. The photosensitive resin composition according to claim 1 , wherein the compound (D) has formula (1) and is selected from the group consisting of 1,4-dihydroxynaphthalene, 2,5-di-tert-butylhydroquinone, and methylhydroquinone.

10. The photosensitive resin composition according to claim 1 , wherein the compound (D) has formula (1) and is 2,5-di-tert-butylhydroquinone.

11. The photosensitive resin composition according to claim 1 , wherein the compound (D) has formula (2) and is 1,4-naphthoquinone.

12. A photosensitive resin composition, comprising:

(A) an alkali-soluble resin;

(B) a compound comprising an ethylenically unsaturated double bond per molecule;

(C) a photo radical polymerization initiator comprising a keto oxime ester structure; and

(D) a compound of Formula (1) or Formula (2):

wherein, in Formula (1):

each R′ independently represents a hydrogen atom or an electron-donating group; and

n represents 0 or 1,

wherein, in Formula (2):

each R 2 independently represents a hydrogen atom or an electron-donating group; and

m represents 0 or 1,

wherein a content by mass of the photo radical polymerization initiator (C) is 0.6 to 4 times of a content by mass of the compound (D), and

wherein a content of the photo radical polymerization initiator (C) with respect to 100 parts by mass of the compound (B) is 3 to 20 parts by mass.

13. A photosensitive resin composition, comprising:

(A) an alkali-soluble resin;

(B) a compound comprising an ethylenically unsaturated double bond per molecule;

(C) a photo radical polymerization initiator comprising a keto oxime ester structure; and

(D) a compound selected from the group consisting of 1,4-dihydroxynaphthalene, 2,5-di-tert-butylhydroquinone, methylhydroquinone, and 1,4-naphthoquinone,

wherein a content by mass of the photo radical polymerization initiator (C) is 0.5 to 5 times of a content by mass of the compound (D), and

wherein a content of the photo radical polymerization initiator (C) with respect to 100 parts by mass of the compound (B) is 3 to 20 parts by mass.

Assignments (3)
MERGER Recorded Mar 23, 2026
From: JSR CORPORATION
To: JICC-02, CO., LTD
Reel/Frame 075191/0149 →
CHANGE OF NAME Recorded Mar 23, 2026
From: JICC-02 CO., LTD
To: JSR CORPORATION
Reel/Frame 075192/0023 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 23, 2014
From: AKIMARU, HISANORI; SAKAKIBARA, HIROKAZU; ISHIKAWA, HIDEFUMI; NARUSE, SHINGO
To: JSR CORPORATION
Reel/Frame 034577/0143 →
Priority Claims (2)
JP 2013-271806 · Dec 27, 2013 · national
JP 2014-215332 · Oct 22, 2014 · national
Continuity (1)
Related Publication 20150185604A1 · Jul 2, 2015