Energy-sensitive resin composition

Patent metadata

Field	Value
Publication number	US-10696845-B2
Application number	US-201615558434-A
Country	US
Kind code	B2
Filing date	Mar 24, 2016
Priority date	Mar 27, 2015
Publication date	Jun 30, 2020
Grant date	Jun 30, 2020

Abstract

An energy-sensitive resin composition with which it is possible, even if the precursor polymer is heat-treated at low temperatures, to produce a film or molded article comprising an imide ring-containing polymer having excellent heat resistance, tensile elongation and chemical resistance with a low dielectric constant, or a film or molded article comprising an oxazole ring-containing polymer having excellent heat resistance, tensile elongation and chemical resistance. A method of manufacturing the film or molded article; a method of forming a pattern using the energy-sensitive resin composition; and a permanent film having excellent heat resistance, tensile elongation and chemical resistance. The energy-sensitive resin composition includes an imidazole compound, a resin precursor component, and a solvent, the resin precursor component being at least one of a monomer component including a diamine compound, a dicarbonyl compound and/or a tetracarboxylic acid dianhydride; and a precursor polymer having a repeating unit.

First claim

The invention claimed is:

1. An energy-sensitive resin composition comprising an imidazole compound (A) represented by the following formula (1a), a resin precursor component (B), and a solvent (S),
wherein the resin precursor component (B) is at least one selected from the group consisting of a monomer component and a precursor polymer, wherein the monomer component comprises (i) a diamine compound represented by the following formula (2) and (ii) a dicarbonyl compound represented by the following formula (3a) and/or a tetracarboxylic dianhydride represented by the following formula (3b), and the precursor polymer is a precursor polymer having a repeating unit represented by the following formula (4):

wherein one R represents a hydrogen atom and the other R represents a monovalent organic group; R 2 represents an optionally substituted aromatic group; each R 4 independently represents a halogen atom, a hydroxyl group, a mercapto group, a sulfide group, a silyl group, a silanol group, a nitro group, a nitroso group, a sulfonato group, a phosphino group, a phosphinyl group, a phosphonato group, or an organic group; n is an integer from 0 to 3; and
the R which represents a monovalent organic group may be bonded to R 2 to form a cyclic structure;

wherein R BN represents an organic group having a valence of (2+q), and q is an integer from 0 to 2;

wherein R BCa represents a divalent organic group; A 1 and A 2 each independently represents a hydrogen atom or a halogen atom;

wherein R BCb represents a tetravalent organic group;

wherein R BN and q are as defined above; R BC represents an organic group having a valence of (2+m); R B3 represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms; and m is an integer from 0 to 2,
wherein m+q>0 is satisfied.

2. The energy-sensitive resin composition according to claim 1 , wherein the imidazole compound (A) comprises a compound represented by the following formula (1):

wherein R 2 , R 4 , and n are as defined for the formula (1a); R 1 represents a hydrogen atom or an alkyl group; R 3 represents an optionally substituted alkylene group, and
R 3 may be bonded to R 2 to form a cyclic structure.

3. The energy-sensitive resin composition according to claim 1 , wherein the resin precursor component (B) is at least one selected from the group consisting of:
(B1) an imide ring forming polymer (excluding a polymer of the following (B3)) obtained by reacting the tetracarboxylic dianhydride and the diamine compound with each other;
(B2) an oxazole ring forming polymer (excluding a polymer of the following (B3)) obtained by reacting a diamine diol represented by the following formula (2a) and the dicarbonyl compound represented by the formula (3a) with each other; and
(B3) an imide ring—oxazole ring forming polymer comprising a repeating unit represented by the following formula (4c) as a main component:

wherein R BNa represents a tetravalent organic group having adjacent two carbon atoms to which each pair of an amino group and a hydroxyl group of two pairs of amino groups and hydroxyl groups included in the diamine diol represented by the formula (2a) are bonded;

wherein R BNa , R BCa , R BCb and R B3 are each independently as defined above; R BNb represents a divalent organic group; R BNd represents an organic group having a valence of (2+q2); R BCd represents an organic group having a valence of (2+m2); m2 and q2 are each independently 1 or 2; a, b, and c are each independently an integer of 0 or more, and a bonding order among repeating units of a pieces of repeating units, b pieces of repeating units, and c pieces of repeating units is not limited to the order described in the formula (4c),
wherein a>0 and b>0 are satisfied, or c>0 is satisfied.

4. The energy-sensitive resin composition according to claim 1 , wherein the imidazole compound (A) comprises a compound represented by the following formula (1-1a):

wherein in the formula (1-1a), R 4 , and n are as defined for the formula (1a) and R is the monovalent organic group; R 5 , R 6 , R 7 , R 8 , and R 9 each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, a sulfide group, a silyl group, a silanol group, a nitro group, a nitroso group, a sulfino group, a sulfo group, a sulfonato group, a phosphino group, a phosphinyl group, a phosphono group, a phosphonato group, an amino group, an ammonio group, or an organic group, wherein at least one of R 5 , R 6 , R 7 , R 8 , and R 9 is a group other than a hydrogen atom;
at least two of R 5 , R 6 , R 7 , R 8 , and R 9 may be bonded to each other to form a cyclic structure; and
R may be bonded to R 7 to form a cyclic structure.

5. The energy-sensitive resin composition according to claim 1 , wherein the imidazole compound (A) is a compound represented by the following formula (1-1):

wherein in the formula (1-1), R 1 represents a hydrogen atom or an alkyl group; R 3 represents an optionally substituted alkylene group; each R 4 independently represents a halogen atom, a hydroxyl group, a mercapto group, a sulfide group, a silyl group, a silanol group, a nitro group, a nitroso group, a sulfonato group, a phosphino group, a phosphinyl group, a phosphonato group, or an organic group; n is an integer from 0 to 3; R 7 , R 8 , and R 9 each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, a sulfide group, a silyl group, a silanol group, a nitro group, a nitroso group, a sulfino group, a sulfo group, a sulfonato group, a phosphino group, a phosphinyl group, a phosphono group, a phosphonato group, an amino group, an ammonio group, or an organic group;
at least two of R 5 , R 6 , R 7 , R 8 , and R 9 may be bonded to each other to form a cyclic structure; and
R 3 may be bonded to R 7 to form a cyclic structure.

6. The energy-sensitive resin composition according to claim 1 , wherein the solvent (S) is a solvent comprising a compound (Si) represented by the following formula (5):

wherein, in the formula (5), R S1 and R S2 each independently represents an alkyl group having 1 to 3 carbon atoms; and R S3 is a group represented by the following formula (5-1) or the following formula (5-2);

wherein in the formula (5-1), R S4 is a hydrogen atom or a hydroxyl group; R S5 and R S6 each independently represents an alkyl group having 1 to 3 carbon atoms, and

Assignees

• Tokyo Ohka Kogyo Co Ltd

Inventors

• Noda Kunihiro
• Chisaka Hiroki
• Shiota Dai

Classifications

• G03F7/038 Primary

  Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) · CPC title

• C08L79/08 Primary

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• C08L79/04

  Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors · CPC title

• C08K5/3445

  Five-membered rings · CPC title

• C08G73/1032

  characterised by the solvent(s) used · CPC title