Di-amine compound, and heat-resistant resin and resin composition using the same

Patent metadata

Field	Value
Publication number	US-11802181-B2
Application number	US-201716343957-A
Country	US
Kind code	B2
Filing date	Aug 28, 2017
Priority date	Nov 10, 2016
Publication date	Oct 31, 2023
Grant date	Oct 31, 2023

Abstract

The present invention relates to a novel di-amine compound, a heat-resistant resin using the di-amine compound, and a resin composition using the heat-resistant resin, and a cured film excellent in chemical resistance and film properties even by a thermal treatment at a low temperature of 200° C. or less can be obtained. The novel di-amine compound is represented by the general formula (1). The heat-resistant resin composition of the present invention or the resin composition can be suitably used in a surface protective film and an interlayer dielectric film of a semiconductor device, a dielectric layer or a planarizing layer of an organic electroluminescent element (organic EL), or the like.

(In the general formula (1), R 1 and R 2 each are a divalent aliphatic group, R 3 and R 4 each are a divalent aliphatic group, aliphatic ring group, aromatic group, a divalent organic group bonded to an aromatic group by —O—, —CO—, —SO 2 —, —CH 2 —, —C(CH 3 ) 2 — or —C(CF 3 ) 2 — (wherein F is fluorine), a divalent organic group in which two or more aromatic groups are bonded by a single bond, or a divalent organic group in which two or more aromatic groups are bonded by —O—, —CO—, —SO 2 —, —CH 2 —, —C(CH 3 ) 2 — or —C(CF 3 ) 2 — (wherein F is fluorine), R 5 and R 6 each are an organic group having any of a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, an aliphatic group, an aromatic group, an acetyl group, a carboxyl group, an ester group, an amide group, an imide group, and a urea group, A is a divalent aliphatic group, aliphatic ring group, aromatic group, a divalent organic group in which two or more aromatic groups are bonded by a single bond, or a divalent organic group in which two or more aromatic groups are bonded by —O—, —S—, —CO—, —SO 2 —, —CH 2 —, —C(CH 3 ) 2 — or —C(CF 3 ) 2 — (wherein F is fluorine), p and q each are an integer number in the range of 0 to 3).

First claim

The invention claimed is:

1. A di-amine compound represented by the general formula (1):

(wherein in the general formula (1), R 1 and R 2 each are a divalent aliphatic group;
R 3 and R 4 each are a divalent aliphatic group, aliphatic ring group, aromatic group, a divalent organic group in which an aromatic group is bonded by —O—, —CO—, —SO 2 —, —CH 2 —, —C(CH 3 ) 2 — or —C(CF 3 ) 2 — (wherein F is fluorine),

a divalent organic group in which two or more aromatic groups are bonded by a single bond, or a divalent organic group in which two or more aromatic groups are bonded by —O—, —CO—, —SO 2 —, —CH 2 —, —C(CH 3 ) 2 — or —C(CF 3 ) 2 — (wherein F is fluorine);
R 5 and R 6 each are a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, an aliphatic group, an aromatic group, an acetyl group, a carboxyl group, or an organic group having any of an ester group, an amide group, an imide group, and a urea group;
A is a divalent aliphatic group, aliphatic ring group, aromatic group, a divalent organic group in which two or more aromatic groups are bonded by a single bond,

or a divalent organic group in which two or more aromatic groups are bonded by —O—, —S—, —CO—, —SO 2 —, —CH 2 —, —C(CH 3 ) 2 — or —C(CF 3 ) 2 — (wherein F is fluorine);
p and q each are an integer number in the range of 0 to 3).

2. The di-amine compound according to claim 1 , which is represented by the general formula (1), wherein R 1 and R 2 in the general formula (1) each are independently a divalent aliphatic group represented by the general formula (2) or the general formula (3),

(wherein in the general formula (1), R 3 and R 4 each are a divalent aliphatic group, aliphatic ring group, aromatic group,
a divalent organic group in which an aromatic group is bonded by —O—, —CO—, —SO 2 —, —CH 2 —, —C(CH 3 ) 2 — or —C(CF 3 ) 2 — (wherein F is fluorine),
a divalent organic group in which two or more aromatic groups are bonded by a single bond, or a divalent organic group in which two or more aromatic groups are bonded by —O—, —CO—, —SO 2 —, —CH 2 —, —C(CH 3 ) 2 — or —C(CF 3 ) 2 — (wherein F is fluorine);
R 5 and R 6 each are a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, an aliphatic group, an aromatic group, an acetyl group, a carboxyl group, or an organic group having any of an ester group, an amide group, an imide group, and a urea group;
A is a divalent aliphatic group, aliphatic ring group, aromatic group, a divalent organic group in which two or more aromatic groups are bonded by a single bond, or a divalent organic group in which two or more aromatic groups are bonded by —O—, —S—, —CO—, —SO 2 —, —CH 2 —, —C(CH 3 ) 2 — or —C(CF 3 ) 2 — (wherein F is fluorine);

p and q each are an integer number in the range of 0 to 3),
[Chem 3]
* R 7 —O a R 8 —O b R 9 —O c —R 10 —*  (2)

(wherein in the general formula (2), R 7 to R 10 each are independently a C 1 -C 10 alkylene group, and each of a, b and c is an integer number in the range of 1≤a≤20, 0≤b≤20, and 0≤c≤20, and the arrangement of the repeating units may be in a block way or in a random way, and * indicates a chemical bond),

(wherein in the general formula (3), R 11 and R 12 each are independently hydrogen, fluorine, or a C 1 -C 6 alkyl group, and n is an integer number of 1 to 20, and * indicates a chemical bond).

3. The di-amine compound according to claim 1 , which is represented by the general formula (1), wherein R 3 in the general formula (1) is a divalent organic group represented by the formula (4) and R 4 in the general formula (1) is a divalent organic group represented by the formula (5),

(wherein in the general formula (1), R 1 and R 2 each are a divalent aliphatic group,
R 5 and R 6 each are a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, an aliphatic group, an aromatic group, an acetyl group, a carboxyl group, or an organic group having any of an ester group, an amide group, an imide group, and a urea group;
A is a divalent aliphatic group, aliphatic ring group, aromatic group, a divalent organic group in which two or more aromatic groups are bonded by a single bond, or a divalent organic group in which two or more aromatic groups are bonded by —O—, —S—, —CO—, —SO 2 —, —CH 2 —, —C(CH 3 ) 2 — or —C(CF 3 ) 2 — (wherein F is fluorine);

p and q each are an integer number in the range of 0 to 3),

(wherein in the general formula (4), * indicates a chemical bond,)

(wherein in the general formula (5), * indicates a chemical bond).

4. A heat-resistant resin having a structure derived from said di-amine compound according to claim 1 .

5. The heat-resistant resin according to claim 4 , comprising at least one kind selected from the group consisting of polyimides, polyamides, polybenzoxazoles, polybenzimidazoles, polybenzothiazoles, precursors thereof, and copolymers thereof.

6. A resin composition comprising said heat-resistant resin according to claim 4 , (b) a photosensitive compound and (c) a solvent.

7. The resin composition according to claim 6 , further comprising (d) a compound having two or more of at least one of an alkoxymethyl group and a methylol group.

8. A resin sheet formed of said resin composition according to claim 6 .

9. A cured film obtained by curing said resin composition according to claim 6 .

10. A cured film obtained by curing said resin sheet of claim 8 .

11. A method of producing a relief pattern of a cured film, comprising the steps of coating said resin composition according to claim 6 on a substrate or laminating a resin sheet formed of said resin composition, and drying said resin composition or said resin sheet to form a resin film;
exposing said resin film through a mask;
eluting or removing irradiated portion by an alkali solution to develop said resin film; and
and heat-treating said resin film after the development.

12. The method of producing a relief pattern of a cured film according to claim 11 , wherein said step of coating said resin composition on a substrate and drying said resin composition to form said resin film comprises a step of coating said resin composition on a substrate using a slit nozzle.

Assignees

• Toray Industries

Inventors

• Masuda Yuki
• Okuda Ryoji

Classifications

• H10W74/40

  characterised by their materials · CPC title

• H10W74/10

  characterised by their shape or disposition · CPC title

• H10W70/60

  Insulating or insulated package substrates; Interposers; Redistribution layers (leadframes H10W70/40) · CPC title

• H10W72/0198

  batch processes · CPC title

• H10W72/9415

  relative to the surface, e.g. recessed, protruding · CPC title