Polyamide acid, polyamide acid solution, polyimide, polyimide film, laminate, flexible device, and method of manufacturing polyimide film

Patent metadata

Field	Value
Publication number	US-11260636-B2
Application number	US-201716319832-A
Country	US
Kind code	B2
Filing date	Jul 31, 2017
Priority date	Aug 31, 2016
Publication date	Mar 1, 2022
Grant date	Mar 1, 2022

Abstract

A polyamide acid of the present invention contains, as a diamine component, 2,2-bistrifluoromethylbenzidine and trans-1,4-cyclohexanediamine, and contains, as a tetracarboxylic acid dianhydride component, a pyromellitic acid anhydride and a 3,3,4,4-biphenyltetracarboxylic acid dianhydride. A ratio of the trans-1,4-cyclohexanediamine to a total amount of the diamine is preferably 0.5-40 mol %. A polyimide is obtained by dehydration ring closure of the polyamide acid.

First claim

What is claimed is:

1. A polyamide acid that is a polyaddition reaction product of a diamine and a tetracarboxylic acid dianhydride, wherein
the diamine comprises 2,2′-bistrifluoromethylbenzidine and trans-1,4-cyclohexanediamine, and
the tetracarboxylic acid dianhydride comprises a pyromellitic acid anhydride and a 3,3′,4,4′-biphenyltetracarboxylic acid dianhydride,
wherein a ratio of the trans-1,4-cyclohexanediamine to a total amount of the diamine is from 0.5 to 25 mol %, and
a ratio of the pyromellitic acid anhydride to a total of 100 mol% of the pyromellitic acid anhydride and the 3,3′,4,4′-biphenyltetracarboxylic acid dianhydride is from 5 to 80 mol %.

2. The polyamide acid according to claim 1 , wherein, in the tetracarboxylic acid dianhydride, a ratio of the pyromellitic acid anhydride to a total of 100 mol % of the pyromellitic acid anhydride and the 3,3′,4,4′-biphenyltetracarboxylic acid dianhydride is from 5 to 70 mol %.

3. A polyamide acid solution, comprising:
the polyamide acid according to claim 1 ; and
an organic solvent.

4. The polyamide acid solution according to claim 3 , further comprising:
an imidazole.

5. The polyamide acid solution according to claim 4 , wherein a content of the imidazole with respect to 1 mole of an amide group of the polyamide acid is 0.10 moles or less.

6. The polyamide acid according to claim 1 , wherein a ratio of the trans-1,4-cyclohexanediamine to a total amount of the diamine is from 1.0 to 25 mol %.

7. The polyamide acid according to claim 1 , wherein a ratio of the trans-1,4-cyclohexanediamine to a total amount of the diamine is from 5 to 25 mol %.

8. The polyamide acid according to claim 1 , wherein, in the tetracarboxylic acid dianhydride, a ratio of the pyromellitic acid anhydride to a total of 100 mol % of the pyromellitic acid anhydride and the 3,3′,4,4′-biphenyltetracarboxylic acid dianhydride is from 10 to 70 mol %.

9. The polyamide acid according to claim 1 , wherein, in the tetracarboxylic acid dianhydride, a ratio of the pyromellitic acid anhydride to a total of 100 mol % of the pyromellitic acid anhydride and the 3,3′,4,4′-biphenyltetracarboxylic acid dianhydride is from 20 to 60 mol %.

10. A polyimide that is a polycondensation reaction product of a diamine and a tetracarboxylic acid dianhydride, wherein
the diamine comprises 2,2′-bistrifluoromethylbenzidine and trans-1,4-cyclohexanediamine, and
the tetracarboxylic acid dianhydride comprises a pyromellitic acid anhydride and a 3,3′,4,4′-biphenyltetracarboxylic acid dianhydride.
wherein a ratio of the trans-1,4-cyclohexanediamine to a total amount of the diamine is from 0.5 to 25 mol %, and
a ratio of the pyromellitic acid anhydride to a total of 100 mol % of the pyromellitic acid anhydride and the 3,3′,4,4′-biphenyltetracarboxylic acid dianhydride is from 5 to 80 mol %.

11. The polyimide according to claim 10 , wherein, in the tetracarboxylic acid dianhydride, a ratio of the pyromellitic acid anhydride to a total of 100 mol % of the pyromellitic acid anhydride and the 3,3′,4,4′-biphenyltetracarboxylic acid dianhydride is from 5 to 70 mol %.

12. A polyimide film, comprising:
the polyimide according to claim 10 .

13. The polyimide film according to claim 12 ,
wherein
a light transmittance at a wavelength of 450 nm of the polyimide film is 75% or more,
a haze of the polyimide film is 1.2% or less, and
a coefficient of thermal expansion of the polyimide film during temperature rising and a coefficient of thermal expansion of the polyimide film during temperature lowering at 100 to 300° C. are 15 ppm/K or less.

14. A laminate, comprising:
a base material: and
the polyimide film according to claim 12 provided on the base material.

15. A flexible device, comprising:
the polyimide film according to claim 12 ; and
an electronic element provided on the polyimide film.

16. A method for manufacturing a polyimide film, comprising:
forming a laminate by applying the polyamide acid solution according to claim 3 onto a base material to provide a film comprising the polyamide acid on the base material; and
heating the laminate to imidize the polyamide acid, thereby forming the polyimide film.

17. A method for manufacturing a polyimide film, comprising:
forming a polyimide film by the method according to claim 16 ; and
separating the base material from the polyimide film.

18. The method for manufacturing a polyimide film according to claim 17 , wherein the separating of the base material from the polyimide film is performed by laser irradiation.

Assignees

• Kaneka Corp

Inventors

• Uno Mari

Classifications

• B29C41/12 Primary

  Spreading-out the material on a substrate {, e.g. on the surface of a liquid} · CPC title

• B29K2079/08

  PI, i.e. polyimides or derivatives thereof · CPC title

• C08J2379/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• C08G73/1039

  comprising halogen-containing substituents · CPC title

• B32B27/281 Primary

  comprising polyimides · CPC title