Compound, acid generator, composition, cured product, cured product manufacturing method, and pattern coating manufacturing method

Patent metadata

Field	Value
Publication number	US-2022137507-A1
Application number	US-202017425308-A
Country	US
Kind code	A1
Filing date	Jan 22, 2020
Priority date	Jan 31, 2019
Publication date	May 5, 2022
Grant date	—

Abstract

A compound represented by formula (A) exhibits excellent balance between acid generation sensitivity and capability of providing a composition with reduced discoloration.In formula (A), R1, R11, R12, R13, R14, R15, R16, R17, and n are as defined in the description. R1 is preferably an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms.

First claim

1 . A compound represented by general formula (A):

wherein R 1 represents an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or an optionally substituted heterocyclic group having 2 to 20 carbon atoms, one or more than one methylene group of the aliphatic or aromatic hydrocarbon group or the heterocyclic group being optionally replaced by a divalent group selected from Group I below;
R 2 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or an optionally substituted heterocyclic group having 2 to 20 carbon atoms, one or more than one methylene group of the aliphatic or aromatic hydrocarbon group or the heterocyclic group being optionally replaced by a divalent group selected from Group I below;

R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , and R 17 each independently represent a hydrogen atom, a halogen-atom, a nitro group, a cyano group, a hydroxy group, a carboxy group, R 20 , —OR 20 , —COR 20 , —OCOR 20 , —COOR 20 , —SR 20 , —SOR 20 , —SO 2 R 20 , —NR 21 R 22 , —NR 21 COR 22 , or —CONR 21 R 22 ;
R 20 , R 21 , and R 22 each independently represent an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or an optionally substituted heterocyclic group having 2 to 20 carbon atoms, one or more than one methylene group of the aliphatic or aromatic hydrocarbon group or the heterocyclic group being optionally replaced by a divalent group selected from Group I below;
R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , and R 21 and R 22 may be taken together to form a ring;
a substituent capable of replacing one or more than one hydrogen atom of the aliphatic or aromatic hydrocarbon group or the heterocyclic group being selected from a halogen atom, a cyano group, a nitro group, a hydroxy group, a thiol group, —COOH, —SO 2 H, an isocyanate group, and an alkyl group with 1 to 4 carbon atoms; and
n represents 0 or 1.

Group I: —O—, —COO—, —OCO—, —CO—, —CS—, —S—, —SO—, —SO 2 —, —NR 30 —, —NR 30 —CO—, —CO—NR 30 —, —NR 30 —COO—, —OCO—NR 30 —, and —SiR 30 R 31 —, wherein R 30 and R 31 each independently represent a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms.

2 . The compound according to claim 1 , wherein n is 1.

3 . The compound according to claim 1 , wherein R 1 is an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms.

4 . The compound according to claim 3 , wherein R 1 is an alkyl group having 1 to 10 carbon atoms with one or more than one of its hydrogen atoms replaced by a halogen atom, an aryl group having 6 to 15 carbon atoms, or an aryl group having 6 to 15 carbon atoms with its hydrogen on the ring replaced by an optionally substituted aliphatic hydrocarbon group.

5 . The compound according to claim 1 , wherein R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , and R 17 each independently represent a hydrogen atom, —OR 20 , —COR 20 , —OCOR 20 , —COOR 20 , —SR 20 , —SOR 20 , —SO 2 R 20 , —NR 21 R 22 , —NR 21 COR 22 , or —CONR 21 R 22 .

6 . The compound according to claim 1 , wherein R 11 , R 12 , R 13 , R 14 , R 16 , and R 17 each represent a hydrogen atom.

7 . The compound according to claim 1 , wherein R 15 is a hydrogen atom or —OR 20 .

8 . The compound according to claim 1 , wherein R 2 is an alkyl group with 1 to 10 carbon atoms or an aryl group with 6 to 15 carbon atoms.

9 . An acid generator comprising the compound according to claim 1 .

10 . A composition comprising the compound according to claim 1 and a resin component.

11 . The composition according to claim 10 , wherein the resin component is an acid-reactive component, the acid-reactive component being an acid-curable component or an acid-decomposable component.

12 . A cured product obtained from the composition according to claim 11 , the acid-reactive component being the acid-curable component.

13 . A method for producing a cured product comprising the step of curing the composition according to claim 11 , the acid-reactive component being the acid-curable component.

14 . A method for forming a patterned coating comprising the steps of:
forming a coating using the composition according to claim 11 and causing the compound present in the coating to generate an acid, and developing a part of the coating after the acid is generated from the compound, the acid-reactive component being the acid-decomposable component.

15 . The compound according to claim 2 , wherein R 1 is an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms.

16 . The compound according to claim 2 , wherein R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , and R 17 each independently represent a hydrogen atom, —OR 20 , —COR 20 , —OCOR 20 , —COOR 20 , —SR 20 , —SOR 20 , —SO 2 R 20 , —NR 21 R 22 , —NR 21 COR 22 , or —CONR 21 R 22 .

17 . The compound according to claim 3 , wherein R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , and R 17 each independently represent a hydrogen atom, —OR 20 , —COR 20 , —OCOR 20 , —COOR 20 , —SR 20 , —SOR 20 , —SO 2 R 20 , —NR 21 R 22 , —NR 21 COR 22 , or —CONR 21 R 22 .

18 . The compound according to claim 4 , wherein R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , and R 17 each independently represent a hydrogen atom, —OR 20 , —COR 20 , —OCOR 20 , —COOR 20 , —SR 20 , —SOR 20 , —SO 2 R 20 , —NR 21 R 22 , —NR 21 COR 22 , or —CONR 21 R 22 .

19 . The compound according to claim 2 , wherein R 11 , R 12 , R 13 , R 14 , R 16 , and R 17 each represent a hydrogen atom.

20 . The compound according to claim 3 , wherein R 11 , R 12 , R 13 , R 14 , R 16 , and R 17 each represent a hydrogen atom.

Assignees

• Adeka Corp

Inventors

• Murai Toshihiko
• Fujita Shohei
• Miyake Junya
• Matsui Izumi
• Otsuka Konomi

Classifications

• C07C381/00

  Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00 · CPC title

• C07C2603/74

  Adamantanes · CPC title

• C07C2601/08

  the ring being saturated · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C07C2602/42

  the bicyclo ring system containing seven carbon atoms · CPC title