Tetracarboxylic dianhydride, polyimide resin and method for producing the same, photosensitive resin compositions, patterning process, method for forming cured film, interlayer insulating film, surface protective film, and electronic parts

Patent metadata

Field	Value
Publication number	US-10919918-B2
Application number	US-201816196281-A
Country	US
Kind code	B2
Filing date	Nov 20, 2018
Priority date	Dec 5, 2017
Publication date	Feb 16, 2021
Grant date	Feb 16, 2021

Abstract

An object of the present invention is to provide: a tetracarboxylic dianhydride which can lead to a polyimide usable as a base resin of a photosensitive resin composition capable of forming a fine pattern and obtaining high resolution without impairing excellent characteristics such as mechanical strength and adhesiveness; a polyimide resin obtained by using the tetracarboxylic dianhydride; and a method for producing the polyimide resin. The tetracarboxylic dianhydride is shown by the following general formula (1).

First claim

What is claimed is:

1. A tetracarboxylic dianhydride shown by the following general formula (1),

wherein Z represents a linear or branched divalent hydrocarbon group having 4 to 100 carbon atoms optionally containing an oxygen atom therein; R 1 to R 4 each represent an identical or different monovalent hydrocarbon group having 1 to 8 carbon atoms; R 5 represents a trivalent organic group; and “n” represents an integer of 1 to 100.

2. The tetracarboxylic dianhydride according to claim 1 , wherein R 5 in the general formula (1) is shown by the following general formula (2) or (3),

wherein R 6 represents a methylene group or an oxygen atom, and

wherein R 7 represents a linear or branched alkylene group or alkenylene group having 3 to 15 carbon atoms.

3. The tetracarboxylic dianhydride according to claim 1 , wherein Z in the general formula (1) is a divalent organic group shown by the following general formula (4),
CH 2 m O R 15 —O l CH 2 m   (4)

wherein R 15 represents a linear or branched alkylene group having 2 to 15 carbon atoms; “l” represents an integer of 1 to 50; and “m” represents an integer of 2 to 15.

4. A polyimide resin comprising a structural unit shown by the following general formula (5),

wherein Z represents a linear or branched divalent hydrocarbon group having 4 to 100 carbon atoms optionally containing an oxygen atom therein; R 1 to R 4 each represent an identical or different monovalent hydrocarbon group having 1 to 8 carbon atoms; R 5 represents a trivalent organic group; “n” represents an integer of 1 to 100; and X represents a divalent organic group.

5. The polyimide resin according to claim 4 , wherein X in the general formula (5) is a divalent organic group shown by the following general formula (6),

wherein “f” represents 0 or 1; Y represents a divalent bonding group; and f=0 represents direct bonding without a bonding group.

6. The polyimide resin according to claim 5 , wherein Y in the general formula (6) is a divalent group shown by the following formula (7) or (8),

7. A method for producing the polyimide resin according to claim 4 , the method comprising reacting a tetracarboxylic dianhydride shown by the following general formula (1) with a diamine shown by the following general formula (9),

wherein Z represents a linear or branched divalent hydrocarbon group having 4 to 100 carbon atoms optionally containing an oxygen atom therein; R 1 to R 4 each represent an identical or different monovalent hydrocarbon group having 1 to 8 carbon atoms; R 5 represents a trivalent organic group; and “n” represents an integer of 1 to 100,
H 2 N—X—NH 2   (9)

wherein X is as defined above.

8. A positive type photosensitive resin composition comprising:
(A) the polyimide resin according to claim 4 ;
(B) a photosensitive agent which generates an acid by light to increase a dissolution rate in an aqueous alkaline solution and is a compound having a quinonediazide structure; and
(D) a solvent.

9. A positive type photosensitive resin composition comprising:
(A) the polyimide resin according to claim 4 ;
(B) a photosensitive agent which generates an acid by light to increase a dissolution rate in an aqueous alkaline solution and is a compound having a quinonediazide structure;
(C) at least one of a crosslinking agent(s) selected from an amino condensate modified by formaldehyde or formaldehyde-alcohol, a phenol compound having two or more methylol groups or alkoxymethylol groups in one molecule on average, a compound in which a hydrogen atom of a hydroxyl group of a polyvalent phenol is substituted by a glycidyl group or a group having a glycidyl group, a compound in which a hydrogen atom of a hydroxyl group of a polyvalent phenol is substituted by a substituent shown by the following formula (C-1), and a compound containing two or more groups each shown by the following formula (C-2) or (C-2′),

wherein a dotted line represents a bond; Rc represents a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms; and “s” represents 1 or 2; and
(D) a solvent.

10. A negative type photosensitive resin composition comprising:
(A′) the polyimide resin according to claim 4 ;
(B′) a photoacid generator;
(C′) at least one of a crosslinking agent(s) selected from an amino condensate modified by formaldehyde or formaldehyde-alcohol, a phenol compound having two or more methylol groups or alkoxymethylol groups in one molecule on average, a compound in which a hydrogen atom of a hydroxyl group of a polyvalent phenol is substituted by a glycidyl group or a group having a glycidyl group, a compound in which a hydrogen atom of a hydroxyl group of a polyvalent phenol is substituted by a substituent shown by the following formula (C-1), and a compound containing two or more groups each shown by the following formula (C-2) or (C-2′),

wherein a dotted line represents a bond; Rc represents a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms; and “s” represents 1 or 2; and
(D) a solvent.

11. A patterning process comprising the steps of:
(1) coating the positive type photosensitive resin composition according to claim 8 onto a substrate to form a film of a photosensitive material;
(2) after heat treatment, exposing the film of the photosensitive material by a high energy beam with a wavelength of 190 to 500 nm or an electron beam through a photomask; and
(3) developing the film using a developing solution of an aqueous alkaline solution.

12. A patterning process comprising the steps of:
(1) coating the positive type photosensitive resin composition according to claim 9 onto a substrate to form a film of a photosensitive material;
(2) after heat treatment, exposing the film of the photosensitive material by a high energy beam with a wavelength of 190 to 500 nm or an electron beam through a photomask; and
(3) developing the film using a developing solution of an aqueous alkaline solution.

13. A patterning process comprising the steps of:
(I) coating the negative type photosensitive resin composition according to claim 10 onto a substrate to form a film of a photosensitive material;
(II) after heat treatment, exposing the film of the photosensitive material by a high energy beam with a wavelength of 190 to 500 nm or an electron beam through a photomask; and
(III) developing the film using a developing solution of an aqueous alkaline solution.

14. The patterning process according to claim 13 , further comprising a heating step after the exposure between the step (II) and the step (III).

15. A method for forming a cured film, comprising he

Assignees

• Shinetsu Chemical Co

Inventors

• Urano Hiroyuki
• Takano Hiroki
• Iio Masashi
• Takemura Katsuya
• Honda Kazuya

Classifications

• C08G73/1053

  with oxygen only in the tetracarboxylic moiety · CPC title

• C08G73/1039 Primary

  comprising halogen-containing substituents · CPC title

• C08G73/106

  containing silicon · CPC title

• C08G77/045

  containing less than 25 silicon atoms · CPC title

• C08G73/1078

  wholly aromatic in the diamino moiety · CPC title