Photosensitive resin composition, method for producing hardened relief pattern, semiconductor device and display device

Patent metadata

Field	Value
Publication number	US-9575410-B2
Application number	US-201214363557-A
Country	US
Kind code	B2
Filing date	Dec 6, 2012
Priority date	Dec 9, 2011
Publication date	Feb 21, 2017
Grant date	Feb 21, 2017

Abstract

Provided is a photosensitive resin composition which comprises: (A-1) a resin containing a structure represented by general formula (1); and (B) a photo-acid generating agent. In general formula (1), X, R 1 to R 7 , m 1 to m 4 , n 1 , n 2 , Y and W are each as defined in the description.

First claim

The invention claimed is:

1. A photosensitive resin composition comprising:
(A-1) a resin containing a structure represented by following formula (1) and
(B) a photoacid generator:

wherein in formula (1),
each X is independently a monovalent group selected from the group consisting of a hydrogen atom, an alkoxycarbonyl group having a carbon number of 2 to 20, an alkoxycarbonylmethyl group having a carbon number of 2 to 20, an alkoxyalkyl group having a carbon number of 2 to 20, a silyl group substituted with at least one alkyl group having a carbon number of 1 to 10, a tetrahydropyranyl group, and a tetrahydrofuranyl group;
each m 1 is independently an integer of 1 to 3,
each m 2 is independently an integer of 0 to 2, and 2≦(m 1 +m 2 )≦4;
each of m 3 and m 4 is independently an integer of 0 to 4;
each of n 1 and n 2 is independently an integer of 1 to 500, and
n 1 /(n 1 +n 2 ) is from 0.35 to 0.95;
each R 1 is independently a monovalent group selected from the group consisting of a hydrocarbon group having a carbon number of 1 to 10, an alkoxy group having a carbon number of 1 to 10, a nitro group, a cyano group, and a group represented by following formula (5) or (6);
when m 2 is 2, the plurality of R 1 may be the same as or different from each other;
each of R 2 to R 5 is independently a hydrogen atom, a monovalent aliphatic group having a carbon number of 1 to 10, or a monovalent aliphatic group having a carbon number of 1 to 10, in which some hydrogen atoms or all hydrogen atoms are substituted with a fluorine atom;
each of R 6 and R 7 is independently a halogen atom, a hydroxyl group or a monovalent organic group;
when m 3 is an integer of 2 to 4, the plurality of R 6 may be the same as or different from each other; when m 4 is an integer of 2 to 4, the plurality of R 7 may be the same as or different from each other;
Y is a divalent organic group represented by following formula (3) or (4);
W is a divalent group selected from the group consisting of a single bond, a chain aliphatic group having a carbon number of 1 to 10, a chain aliphatic group having a carbon number of 1 to 10, in which some hydrogen atoms or all hydrogen atoms are substituted with a fluorine atom, an alicyclic group having a carbon number of 3 to 20, an alicyclic group having a carbon number of 3 to 20, in which some hydrogen atoms or all hydrogen atoms are substituted with a fluorine atom, an alkylene oxide group having from 1 to 20 repeating units, and groups represented by following formula (2):

and the polymer structure may be a random structure or a block structure;
—CR 8 R 9 —  (3)

wherein in formula (3),
each of R 8 and R 9 is independently a hydrogen atom, a monovalent organic group having a carbon number of 1 to 11, or a group containing a carboxyl group, a sulfonic acid group or a phenolic hydroxyl group;

wherein in formula (4),
each of R 11 to R 14 is independently a hydrogen atom, a monovalent aliphatic group having a carbon number of 1 to 10, or a monovalent aliphatic group having a carbon number of 1 to 10, in which some hydrogen atoms or all hydrogen atoms are substituted with a fluorine atom; m 5 is an integer of 1 to 4;
when m 5 is 1, R 10 is a hydroxyl group, a carboxyl group or a sulfonic acid group, and when m 5 is an integer of 2 to 4, at least one R 10 is a hydroxyl group and the remaining R 10 are a halogen atom, a hydroxyl group, a monovalent organic group, a carboxyl group or a sulfonic acid group; and all R 10 may be the same or different;

wherein in formula (5),
R 15 is a monovalent group selected from the group consisting of a hydroxyl group, an aliphatic group having a carbon number of 1 to 12, an alicyclic group having a carbon number of 3 to 12, an aromatic group having a carbon number of 6 to 18, —NH 2 , and groups represented by —NH—R 19 , —N(R 19 ) 2 and —O—R 19 wherein R 19 is a monovalent group selected from an aliphatic group having a carbon number of 1 to 12, an alicyclic group having a carbon number of 3 to 12, and an aromatic group having a carbon number of 6 to 18;

wherein in formula (6), each of R 16 and R 17 ′ is independently a monovalent group selected from the group consisting of a hydrogen atom, an aliphatic group having a carbon number of 1 to 12, an alicyclic group having a carbon number of 3 to 12, and an aromatic group having a carbon number of 6 to 18, and R 16 and R 17 ′ may form a ring.

2. The photosensitive resin composition according to claim 1 , wherein in formula (1), all X are a hydrogen atom.

3. The photosensitive resin composition according to claim 1 , wherein Y in formula (1) is a resin containing a structure represented by following formula (11) or (12):
—CHR 8 —  (11)

wherein R 8 is a hydrogen atom or a monovalent organic group having a carbon number of 1 to 11;

wherein in formula (12),
R 17 is a hydrocarbon group having a carbon number of 1 to 10 or an alkoxy group having a carbon number of 1 to 10,
m 6 is an integer of 0 to 3, and
when m 6 is 2 or 3, the plurality of R 17 may be the same or different.

4. The photosensitive resin composition according to claim 1 , wherein
R 1 in formula (1) is at least one member selected from the group consisting of a hydrocarbon group having a carbon number of 1 to 10, an alkoxy group having a carbon number of 1 to 10, and a group represented by formula (5),
W in formula (1) is a single bond, and R 15 in formula (5) is a monovalent group selected from the group consisting of a hydroxyl group, —NH 2 , and groups represented by —NH—R 19 , —N(R 19 ) 2 and —O—R 19 wherein R 19 is a monovalent group selected from an aliphatic group having a carbon number of 1 to 12, an alicyclic group having a carbon number of 3 to 12, and an aromatic group having a carbon number of 6 to 18.

5. The photosensitive resin composition according to claim 1 , wherein resin (A-1) is a resin containing a structure represented by following formula (13):

wherein in formula (13),
each m 2 is independently an integer of 0 to 2;
each of m 3 and m 4 is independently an integer of 0 to 4;
each of n 1 and n 2 is independently an integer of 1 to 500, and n 1 /(n 1 +n 2 ) is from 0.35 to 0.8;
each R 1 is independently a monovalent group having a carbon number of 1 to 10 selected from a hydrocarbon group and an alkoxy group;
when m 2 is 2, the plurality of R 1 may be the same as or different from each other;
each of R 2 to R 5 is independently a hydrogen atom, a monovalent aliphatic group having a carbon number of 1 to 10, or a monovalent aliphatic group having a carbon number of 1 to 10, in which some hydrogen atoms or all hydrogen atoms are substituted with a fluorine atom;
each of R 6 and R 7 is independently a halogen atom, a hydroxyl group or a monovalent organic group;
when m 3 is 2 to 4, the plurality of R 6 may be the same as or different from each other;

Assignees

• Asahi Kasei E Materials Corp

Inventors

• Shibui Satoshi
• Hirata Tatsuya
• Sasaki Takahiro
• Yamada Taisuke

Classifications

• H10W74/47

  comprising organic materials, e.g. plastics or resins · CPC title

• H10W74/01

  Manufacture or treatment · CPC title

• G03F7/023 Primary

  Macromolecular quinonediazides; Macromolecular additives, e.g. binders {(G03F7/0226 takes precedence)} · CPC title

• C08L65/00

  Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C08L7/00 - C08L57/00, C08L61/00 take precedence); Compositions of derivatives of such polymers · CPC title

• C08G8/22

  Resorcinol · CPC title