Polyamic acid, varnish comprising same and polyimide film

Patent metadata

Field	Value
Publication number	US-9902810-B2
Application number	US-201414781927-A
Country	US
Kind code	B2
Filing date	Apr 1, 2014
Priority date	Apr 3, 2013
Publication date	Feb 27, 2018
Grant date	Feb 27, 2018

Abstract

The present invention addresses the problem of providing: a polyimide film that has a small phase difference in the thickness direction and has a low coefficient of linear thermal expansion; and a polyamic acid and varnish to obtain the same. In order to solve this problem, the present invention provides a polyimide film which comprises polyimide that is produced by reacting a diamine component and a tetracarboxylic dianhydride component, the polyimide film having a coefficient of linear thermal expansion of 35 ppm/K or less over a temperature range of 100 to 200 DEG C, an absolute value of phase difference in the thickness direction of 200 nm or less per 10 μm thickness, a glass transition temperature of 260 DEG C or more, and a total light transmittance of 85% or more.

First claim

The invention claimed is:

1. A polyimide film made of a polyimide obtained by reacting a diamine component with a tetracarboxylic dianhydride component,
wherein a coefficient of linear thermal expansion is 35 ppm/K or less throughout the range from 100° C. to 200° C.,
an absolute value of retardation in a thickness direction is 200 nm or less per thickness of 10 μm,
a glass transition temperature is 260° C. or higher, and
a total light transmittance is 85% or more;
wherein the diamine component includes 5 to 80 mol % based on the total amount of the diamine component of 1,5-diamino naphthalene represented by chemical formula (1), and
the tetracarboxylic dianhydride component includes 0 to 95 mol % based on the total amount of the tetracarboxylic dianhydride component of naphthalene 2,3,6,7-tetracarboxylic dianhydride represented by chemical formula (2A) and/or naphthalene 1,2,5,6-tetracarboxylic dianhydride represented by chemical formula (2B)

and
wherein the tetracarboxylic dianhydride component includes 5 to 50 mol % based on the total amount of the tetracarboxylic dianhydride component of fluorenylidene bis(phthalic anhydride) represented by chemical formula (4)

2. The polyimide film according to claim 1 ,
wherein the diamine component includes 0 to 50 mol % based on the total amount of the diamine component of 9,9-bis(4-aminophenyl)fluorene represented by chemical formula (3)

3. The polyimide film according to claim 1 , wherein the diamine component includes one or more compounds selected from the group consisting of 1,4-bis(aminomethyl)cyclohexane, bis(aminomethyl)norbornane, isophoronediamine, trans-1,4-diaminocyclohexane, and a hydrogenated product of 4,4′-diaminodiphenylmethane.

4. A polyamic acid obtained by reacting a diamine component with a tetracarboxylic dianhydride component,
wherein a coefficient of linear thermal expansion of a polyimide film obtained by imidizing the polyamic acid is 35 ppm/K or less throughout the range from 100° C. to 200° C.,
an absolute value of retardation in a thickness direction of the polyimide film is 200 nm or less per thickness of 10 μm,
a glass transition temperature of the polyimide film is 260° C. or higher, and
a total light transmittance is 85% or more;
wherein the diamine component includes 5 to 80 mol % based on the total amount of the diamine component of 1,5-diamino naphthalene represented by chemical formula (1), and
the tetracarboxylic dianhydride component includes 0 to 95 mol % based on the total amount of the tetracarboxylic dianhydride component of naphthalene 2,3,6,7-tetracarboxylic dianhydride represented by chemical formula (2A) and/or naphthalene 1,2,5,6-tetracarboxylic dianhydride represented by chemical formula (2B)

and
wherein the tetracarboxylic dianhydride component includes 5 to 50 mol % based on the total amount of the tetracarboxylic dianhydride component of fluorenylidene bis(phthalic anhydride) represented by chemical formula (4)

5. The polyamic acid according to claim 4 ,
wherein the diamine component includes 0 to 50 mol % based on the total amount of the diamine component of 9,9-bis(4-aminophenyl)fluorene represented by chemical formula (3)

6. The polyamic acid according to claim 4 , wherein the diamine component includes one or more compounds selected from the group consisting of 1,4-bis(aminomethyl)cyclohexane, bis(aminomethyl)norbornane, isophoronediamine, trans-1,4-diaminocyclohexane, and a hydrogenated product of 4,4′-diaminodiphenylmethane.

7. A polyamic acid varnish comprising the polyamic acid according to claim 4 .

8. A dry film comprising the polyamic acid according to claim 4 .

9. A polyimide obtained by curing the polyamic acid according to claim 4 .

10. A method of manufacturing a polyimide laminate in which a substrate and a polyimide layer are laminated, the method comprising:
coating a substrate with the polyamic acid varnish according to claim 7 ; and
heating a film of the coated polyamic acid varnish in an inert gas atmosphere.

11. A method of manufacturing a polyimide laminate in which a substrate and a polyimide layer are laminated, the method comprising:
coating a substrate with the polyamic acid varnish according to claim 7 ; and
heating a film of the coated polyamic acid varnish under an atmosphere of 15 kPa or less.

12. A polyimide film obtained by peeling off the substrate from the polyimide laminate obtained by the manufacturing method of claim 10 .

13. A method of manufacturing a display apparatus, comprising:
peeling off the substrate from the polyimide laminate obtained by the manufacturing method of claim 10 , thereby obtaining a polyimide film; and
forming a device on the polyimide film.

14. A method of manufacturing a display apparatus, comprising:
forming a device on the polyimide layer of the polyimide laminate obtained by the manufacturing method of claim 10 ; and
peeling off the polyimide layer on which the device is formed from the substrate.

15. A touch panel display obtained by the method of manufacturing the display apparatus according to claim 13 .

16. A liquid crystal display obtained by the method of manufacturing the display apparatus according to claim 13 .

17. An organic EL display obtained by the method of manufacturing the display apparatus according to claim 13 .

18. A touch panel display obtained by the method of manufacturing the display apparatus according to claim 14 .

19. A liquid crystal display obtained by the method of manufacturing the display apparatus according to claim 14 .

20. An organic EL display obtained by the method of manufacturing the display apparatus according to claim 14 .

21. A polyimide film obtained by peeling off the substrate from the polyimide laminate obtained by the manufacturing method of claim 11 .

22. A method of manufacturing a display apparatus, comprising:
peeling off the substrate from the polyimide laminate obtained by the manufacturing method of claim 11 , thereby obtaining a polyimide film; and
forming a device on the polyimide film.

23. A method of manufacturing a display apparatus, comprising:
forming a device on the polyimide layer of the polyimide laminate obtained by the manufacturing method of claim 11 ; and
peeling off the polyimide layer on which the device is formed from the substrate.

24. A touch panel display obtained by the method of manufacturing the display apparatus according to claim 22 .

25. A liquid crystal display obtained by the method of manufacturing the display apparatus according to claim 22 .

26. An organic EL display obtained by the method of manufacturing the display apparatus according to claim 22 .

27. A touch panel display obtained by the method of manufacturing the display apparatus according to claim 23 .

Assignees

• Mitsui Chemicals Inc

Inventors

• Urakami Tatsuhiro
• Okazaki Masaki
• Fukukawa Kenichi
• Sakata Yoshihiro
• Okubo Atsushi

Classifications

• C08G73/1067 Primary

  Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound · CPC title

• H01L27/323

  Electricity · mapped topic

• B32B3/08 Primary

  characterised by added members at particular parts {(layer formed of separate pieces of material which are juxtaposed side-by-side B32B3/14, B32B3/18)} · CPC title

• B32B2457/20

  Displays, e.g. liquid crystal displays, plasma displays · CPC title

• C08G73/126

  the unsaturated precursors being wholly aromatic · CPC title