Polyimide precursor, polyimide resin film produced from said polyimide precursor, display element, optical element, light-receiving element, touch panel and circuit board each equipped with said polyimide resin film, organic EL display, and methods respectively for producing organic EL element and color filter

Patent metadata

Field	Value
Publication number	US-9828469-B2
Application number	US-201415021144-A
Country	US
Kind code	B2
Filing date	Sep 18, 2014
Priority date	Sep 27, 2013
Publication date	Nov 28, 2017
Grant date	Nov 28, 2017

Abstract

The present invention provides a polyimide precursor that serves to produce a cured film that has high light permeability in combination with low birefringence and low linear thermal expansion. The polyimide precursor includes at least an acid dianhydride residue as represented by Formula (1), a diamine residue as represented by Formula (2), and one or more diamine residues as represented by Formula (3), the acid dianhydride residue as represented by Formula (1) accounting for 50 mol % or more of the total quantity of acid dianhydride residues in the polyimide precursor, the diamine residue as represented by Formula (2) accounting for 50 mol % or more of the total quantity of diamine residues in the polyimide precursor, and the diamine residue as represented by Formula (3) accounting for 15 mol % or less of the total quantity of diamine residues in the polyimide precursor.

First claim

The invention claimed is:

1. A polyimide precursor comprising at least
an acid dianhydride residue as represented by Formula (1),
a diamine residue as represented by Formula (2), and
one or more diamine residues as represented by Formula (3),

the acid dianhydride residue as represented by Formula (1) accounting for 50 mol % or more of the total quantity of acid dianhydride residues in the polyimide precursor,
the diamine residue as represented by Formula (2) accounting for 50 mol % or more of the total quantity of diamine residues in the polyimide precursor, and
the diamine residue as represented by Formula (3) accounting for 15 mol % or less of the total quantity of diamine residues in the polyimide precursor:

wherein R 1 to R 8 in Formula (3) are independently each selected from the group consisting of a hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkoxy group, aryl ether group, aryl group, haloalkyl group, cyano group, and silyl group, which may further contain a substituent group and which may contain a condensed ring structure formed of adjacent groups connected to each other; and
wherein A 1 and A 2 , which may be identical to or different from each other, each represent a structure formed of an aromatic ring, aliphatic ring, chain hydrocarbon group, a combination of a plurality thereof, or a combination thereof with one selected from the group consisting of amide group, ester group, ether group, alkylene group, oxyalkylene group, vinylene group, and haloalkylene group.

2. A polyimide precursor as claimed in claim 1 further comprising an acid dianhydride residue as represented by Formula (4):

wherein R 9 to R 16 in Formula (4) are independently each selected from the group consisting of a hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkoxy group, aryl ether group, aryl group, haloalkyl group, cyano group, and silyl group, which may further contain a substituent group and which may contain a condensed ring structure formed of adjacent groups connected to each other; and

B 1 and B 2 , which may be identical to or different from each other, each represent a structure formed of an aromatic ring, aliphatic ring, chain hydrocarbon group, a combination of a plurality thereof, or a combination thereof with one selected from the group consisting of amide group, ester group, ether group, alkylene group, oxyalkylene group, vinylene group, and haloalkylene group.

3. A polyimide precursor as claimed in claim 2 , wherein B 1 and B 2 in Formula (4) each represent one selected from the group of (11) to (17):

wherein X in Formulae (11) to (13) is a single bond, ether group, alkylene group, oxyalkylene group, or vinylene group, and the other bond is connected to a fluorene ring;
Y in Formulae (14) to (17) is an amide group, ester group, ether group, alkylene group, oxyalkylene group, vinylene group, or haloalkylene group;
Z in Formulae (14) to (17) is a single bond and the other bond is connected to the fluorene ring;
R 81 to R 157 in Formula (11) to (17) are independently selected from the group consisting of a hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkoxy group, aryl ether group, aryl group, haloalkyl group, cyano group, hydroxyl group, and silyl group; one of R 81 to R 84 in Formula (11) is a linking group containing X; one of R 85 to R 94 in Formula (12) is a linking group containing X; one of R 98 to R 102 and one of R 103 to R 112 in Formula (14) each are a linking group containing Y; one of R 113 to R 123 and one of R 124 to R 127 in Formula (15) each are a linking group containing Y; one of R 128 to R 132 and one of R 133 to R 136 in Formula (16) each are a linking group containing Y; and one of R 137 to R 147 and one of R 148 to R 157 in Formula (17) each are a linking group containing Y.

4. A polyimide precursor as claimed in claim 2 , wherein the acid dianhydride residue as represented by Formula (4) is at least one tetravalent organic group selected from Formulae (22) to (24):

5. A polyimide precursor as claimed in claim 1 , wherein A 1 and A 2 in Formula (3) each represent one selected from the group of (5) to (10) given below:

wherein X in Formulae (5) to (7) is a single bond, ether group, alkylene group, oxyalkylene group, or vinylene group, and the other bond is connected to a fluorene ring;
Y in Formulae (8) to (10) is an amide group, ester group, ether group, alkylene group, oxyalkylene group, vinylene group, or haloalkylene group;
R 17 to R 80 in Formulae (5) to (10) are independently selected from the group consisting of a hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkoxy group, aryl ether group, aryl group, haloalkyl group, cyano group, hydroxyl group, and silyl group; one of R 17 to R 21 in Formula (5) is a linking group containing X; one of R 22 to R 32 in Formula (6) is a linking group containing X; either of the two ring structures in Formulae (8) to (10) may be connected to the fluorene ring; one of R 33 to R 37 and one of R 38 to R 48 each are a linking group containing Y; one of R 49 to R 53 and one of R 54 to R 58 each are a linking group containing Y; and one of R 59 to R 69 and one of R 70 to R 80 each are a linking group containing Y.

6. A polyimide precursor as claimed in claim 1 , wherein the diamine residue as represented by Formula (3) is at least one divalent organic group selected from Formulae (18) to (21):

7. A polyimide precursor as claimed in claim 1 further comprising at least one acid dianhydride residue selected from the group consisting of Formulae (25) to (28):

8. A polyimide precursor as claimed in claim 7 , wherein the number of moles of the diamine residue as represented by Formula (3) is equal to or smaller than the total number of moles of the at least one acid dianhydride residue selected from the group consisting of Formulae (25) to (28).

9. A polyimide resin film obtainable from a polyimide precursor as claimed in claim 1 .

10. A display element comprising polyimide resin film as claimed in claim 9 .

11. A display element as claimed in claim 10 , wherein the display element is an organic EL emission element.

12. An organic EL display equipped with an organic EL emission element as claimed in claim 11 .

13. An optical element comprising polyimide resin film as claimed in claim 9 .

14. An optical element as claimed in claim 13 , wherein the optical element is a color filter.

15. An organic EL display equipped with a color filter as claimed in claim 14 .

16. A light-receiving element comprising polyimide resin film as claimed in claim 9 .

17

Assignees

• Toray Industries

Inventors

• Wakita Junji
• Arimoto Yukari
• Tomikawa Masao

Classifications

• H10K50/844

  Encapsulations · CPC title

• C08G73/1075

  Partially aromatic polyimides · CPC title

• H10K59/873

  Encapsulations · CPC title

• H10K71/80

  using temporary substrates · CPC title

• H01L27/322

  Electricity · mapped topic