Resin containing phenolic hydroxyl groups, and resist film

Patent metadata

Field	Value
Publication number	US-10414850-B2
Application number	US-201615775921-A
Country	US
Kind code	B2
Filing date	Nov 17, 2016
Priority date	Dec 2, 2015
Publication date	Sep 17, 2019
Grant date	Sep 17, 2019

Abstract

Provided are a resin containing phenolic hydroxyl groups having excellent developability, heat resistance, and substrate followability, a photosensitive composition, a curable composition, and a resist film which contain the resin containing phenolic hydroxyl group. The resin containing phenolic hydroxyl groups obtained by reacting a novolac resin intermediate obtained by reacting a triarylmethane compound (A) with an aldehyde compound (B) as essential components, with an alkene compound (C) having 9 to 24 carbon atoms, a photosensitive composition, a curable composition, and a resist film which contain the resin containing phenolic hydroxyl groups.

First claim

The invention claimed is:

1. A resin containing phenolic hydroxyl groups, comprising, as a repeating unit, a structural moiety represented by Structural Formula (1):

(wherein R 1 represents any one of a hydrogen atom, an alkyl group, and an aryl group, and X is a structural moiety (α) represented by Structural Formula (2) or a structural moiety (β) represented by Structural Formula (3):

wherein k is any one of 0, 1, and 2, R 2 's each independently represent any one of a hydrogen atom, an aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group, an alkoxy group, and a halogen atom, 1's are each independently an integer of to 4, R 3 represents any one of a hydrogen atom, an aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group, an alkoxy group, and a halogen atom, m is an integer of 1 to 4, asterisks each are a bonding point on any of the three aromatic rings shown in the formula, and two asterisks may be bonded to the same aromatic ring or may be bonded to different aromatic rings:

wherein k is any one of 0, 1, and 2, R 2 's each independently represent any one of a hydrogen atom, an aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group, an alkoxy group, and a halogen atom, 1's are each independently an integer of to 4, R 3 represents any one of a hydrogen atom, an aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group, an alkoxy group, and a halogen atom, n is an integer of 1 to 6, asterisks each are a bonding point on any of the three aromatic rings shown in the formula, and two asterisks may be bonded to the same aromatic ring or may be bonded to different aromatic rings),
wherein at least one of R 2 and R 3 present in the resin is an aliphatic hydrocarbon group having 9 to 24 carbon atoms, and 20 mol % or more of X is a structural moiety in which a value of k is 1.

2. A composition comprising the resin containing phenolic hydroxyl groups according to claim 1 .

3. A cured product, which is formed by curing the composition according to claim 2 .

4. The cured product according to claim 3 , which is a resist film.

5. A method of producing a resin containing phenolic hydroxyl groups, comprising:
reacting a triarylmethane compound (A) having a molecular structure represented by Structural Formula (4) or (5) with an aldehyde compound (B) as essential components, to thereby obtain a novolac resin intermediate, and
reacting the novolac resin intermediate with an alkene compound (C) having 9 to 24 carbon atoms:

(wherein k is any one of 0, 1, and 2, R 2 's each independently represent any one of a hydrogen atom, an aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group, an alkoxy group, and a halogen atom, 1's are each independently an integer of to 4, R 3 represents any one of a hydrogen atom, an aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group, an alkoxy group, and a halogen atom, m is an integer of 1 to 4, and n is an integer of 1 to 6).

Assignees

• Dainippon Ink & Chemicals

Inventors

• Imada Tomoyuki
• Sato Yusuke

Classifications

• G03F7/0236

  Condensation products of carbonyl compounds and phenolic compounds, e.g. novolak resins · CPC title

• C08L61/12

  with polyhydric phenols · CPC title

• C08G8/20 Primary

  with polyhydric phenols · CPC title

• C08G8/04

  of aldehydes · CPC title

• G03F7/023

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