Abstract: The present invention relates to: a novel diamine compound; a heat-resistant resin which uses this diamine compound; and a resin composition which uses this heat-resistant resin. Consequently the present invention enables the achievement of a cured film that has excellent chemical resistance and film characteristics even in cases where a heat treatment is carried out at such a low temperature as 200°C or less. The novel diamine is represented by general formula (1). A heat-resistant resin or a resin composition according to the present invention is suitable for use in a surface protective film or an interlayer insulating film of a semiconductor device and an insulating layer or a planarization layer of an organic electroluminescent (organic EL) element.
WE CLAIM:
1. A di-amine compound represented by the general formula (1):
[Chem 1]
5 (wherein in the general formula (1), R1 and R2 each are a divalent
aliphatic group;
R3 and R4 each are a divalent aliphatic group, aliphatic ring group,
aromatic group,
a divalent organic group in which an aromatic group is bonded by -0-, 10 -CO-, -SO2-, -CH2-, -C(CH3)2- or -C(CF3)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 -0-, -CO-, -SO2-, -CH2-, -C(CH3)2- or -C(CF3)2- (wherein F is
15 fluorine);
R5 and R6 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;
20 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 -0-, -S-, -CO-, -SO2-, -CH2-, -C(CH3)2- or -C(CF3)2- (wherein
25 F is fluorine);
100
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 R1 and R2 in the general formula (1) each are independently a divalent aliphatic group represented 5 by the general formula (2) or the general formula (3), [C.hem 2]
(wherein in the general formula (1), R3 and R4 each are a divalent
aliphatic group, aliphatic ring group, aromatic group, 10 a divalent organic group in which an aromatic group is bonded by -0-,
-CO-, -SO2-, -CH2-, -C(CH3)2- or -C(CF3)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 15 bonded by -0-, -CO-, -S02-, -CH2-, -C(CH3)2- or -C(CF3)2- (wherein F is
fluorine);
R5 and R6 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 20 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
101
bonded by -0-, -S-, -CO-, -SO2-, -CH2-, -C(CH3)2- or -C(CF3)2- (wherein
F is fluorine);
p and q each are an integer number in the range of 0 to 3),
[Chem 3]
(wherein in the general formula (2), R7 to R10 each are independently a
C1-C10 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 J 10 a chemical bond),
[Chem 4]
(3).
(wherein in the general formula (3), R11 and R12 each are independently hydrogen, fluorine, or a Ci-C6 alkyl group, and n is an integer number of
15 1 to 20, and * indicates a chemical bond).
3. The di-amine compound according to claim 1 or 2, which is
represented by the general formula (1), wherein R3 in the general formula (1) is a divalent organic group represented by the formula (4) and R4 in the general formula (1) is a divalent organic group represented by the
20 formula (5), [Chem 5]
102
(wherein in the general formula (1), R1 and R2 each are a divalent aliphatic group,
R5 and R6 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 -0-, -S-, -CO-, -SO2-, -CH2-, -C(CH3)2- or -C(CF3)2- (wherein F is fluorine);
p and q each are an integer number in the range of 0 to 3), [Chem 6]
(wherein in the general formula (4), * indicates a chemical bond,) [Chem 7]
(wherein in the general formula (5), * indicates a chemical bond).
4. A heat-resistant resin having a structure derived from said
103
di-amine compound according to any one of claims 1 to 3.
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
5 thereof, and copolymers thereof.
6. A resin composition comprising said heat-resistant resin
according to claim 4 or 5, (b) a photosensitive compound and (c) a
solvent.
7. The resin composition according to claim 6, further comprising
10 (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 or 7.
9. A cured film obtained by curing said resin composition according
15 to claim 6 or 7.
10. A cured film obtained by curing said resin sheet of claim 811. A method of producing a relief pattern of a cured film, comprising
the steps of coating said resin composition according to claim 6 or 7 on a
substrate or laminating said resin sheet according to claim 8 on a
20 substrate, 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 25 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
104
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.
13. An organic EL display device, wherein said cured film according
5 to claim 9 or 10 which is patterned or not patterned is arranged in one or
both of a planarizing layer and a dielectric layer of a first electrode of a driving circuit.
14. An electronic component or a semiconductor apparatus, wherein
said cured film according to claim 9 or 10 patterned or not pattered is
10 arranged between rewires as an interlayer dielectric film.
15. The electronic component or a semiconductor apparatus according
to claim 14, wherein said rewires are copper metal wires, and the width of
said copper metal wires and the distance between adjacent wires are 5 urn
or less.
15 16. An electronic component or a semiconductor apparatus, wherein said cured film according to claim 9 or 10 patterned or not patterned is arranged between rewires as an interlayer dielectric film on an encapsulation resin substrate on which a silicon chip has been arranged. .17. The semiconductor electronic component or the semiconductor
20 apparatus according to any one of claims 14 to 16, wherein said rewires are copper metal wires and are connected with a semiconductor chip via a
bump.
18. The semiconductor electronic component or the semiconductor
apparatus according to any one of claims 14 to 17, wherein, for said
25 rewires, the width of metal wires and the distance between adjacent wires get thinner as the wires get closer to said semiconductor chip.
19. The semiconductor electronic component or the semiconductor
105
apparatus according to any one of claims 14 to 18, wherein the thickness of said interlayer dielectric film arranged between said rewires gets thinner as said interlayer dielectric film gets closer to said semiconductor chip. 5 20. A method of producing an electronic component or a
semiconductor apparatus; comprising the steps of arranging said cured film according to claim 9 or 10 on a support substrate on which a . temporary attachment material has been arranged as an interlayer dielectric film between rewires; 10 arranging a silicon chip and an encapsulation resin thereon; and,
detaching said support substrate on which said temporary attachment material has been arranged and said rewires.
106
| # | Name | Date |
|---|---|---|
| 1 | 201947018365-FORM 3 [10-10-2019(online)].pdf | 2019-10-10 |
| 1 | 201947018365.pdf | 2019-05-08 |
| 2 | Correspondence by Agent_Form 1_20-05-2019.pdf | 2019-05-20 |
| 2 | 201947018365-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [08-05-2019(online)].pdf | 2019-05-08 |
| 3 | 201947018365-STATEMENT OF UNDERTAKING (FORM 3) [08-05-2019(online)].pdf | 2019-05-08 |
| 3 | 201947018365-CLAIMS UNDER RULE 1 (PROVISIO) OF RULE 20 [08-05-2019(online)].pdf | 2019-05-08 |
| 4 | 201947018365-COMPLETE SPECIFICATION [08-05-2019(online)].pdf | 2019-05-08 |
| 4 | 201947018365-PROOF OF RIGHT [08-05-2019(online)].pdf | 2019-05-08 |
| 5 | 201947018365-DECLARATION OF INVENTORSHIP (FORM 5) [08-05-2019(online)].pdf | 2019-05-08 |
| 5 | 201947018365-PRIORITY DOCUMENTS [08-05-2019(online)].pdf | 2019-05-08 |
| 6 | 201947018365-POWER OF AUTHORITY [08-05-2019(online)].pdf | 2019-05-08 |
| 6 | 201947018365-DRAWINGS [08-05-2019(online)].pdf | 2019-05-08 |
| 7 | 201947018365-FORM 1 [08-05-2019(online)].pdf | 2019-05-08 |
| 8 | 201947018365-POWER OF AUTHORITY [08-05-2019(online)].pdf | 2019-05-08 |
| 8 | 201947018365-DRAWINGS [08-05-2019(online)].pdf | 2019-05-08 |
| 9 | 201947018365-PRIORITY DOCUMENTS [08-05-2019(online)].pdf | 2019-05-08 |
| 9 | 201947018365-DECLARATION OF INVENTORSHIP (FORM 5) [08-05-2019(online)].pdf | 2019-05-08 |
| 10 | 201947018365-COMPLETE SPECIFICATION [08-05-2019(online)].pdf | 2019-05-08 |
| 10 | 201947018365-PROOF OF RIGHT [08-05-2019(online)].pdf | 2019-05-08 |
| 11 | 201947018365-CLAIMS UNDER RULE 1 (PROVISIO) OF RULE 20 [08-05-2019(online)].pdf | 2019-05-08 |
| 11 | 201947018365-STATEMENT OF UNDERTAKING (FORM 3) [08-05-2019(online)].pdf | 2019-05-08 |
| 12 | Correspondence by Agent_Form 1_20-05-2019.pdf | 2019-05-20 |
| 12 | 201947018365-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [08-05-2019(online)].pdf | 2019-05-08 |
| 13 | 201947018365-FORM 3 [10-10-2019(online)].pdf | 2019-10-10 |