Polyimide and alicyclic tetracarboxylic dianhydride used for producing the same

Patent metadata

Field	Value
Publication number	US-9399703-B2
Application number	US-201314424314-A
Country	US
Kind code	B2
Filing date	Aug 29, 2013
Priority date	Aug 31, 2012
Publication date	Jul 26, 2016
Grant date	Jul 26, 2016

Abstract

A polyimide containing at least one of repeating units represented by the following general formulae (1) and (2):

wherein the formulae (1) and (2), R 1 , R 2 , and R 3 each independently represents a hydrogen atom or the like, R 4 represents an aryl group having 6 to 40 carbon atoms, and n represents an integer of 0 to 12, wherein a total amount of the repeating units represented by the general formulae (1) and (2) is 90% by mole or more relative to all repeating units.

First claim

The invention claimed is:

1. A polyimide comprising at least one of repeating units represented by the following general formulae (1) and (2):

wherein
the formulae (1) and (2), R 1 , R 2 , and R 3 each independently represent one selected from the group consisting of a hydrogen atom, alkyl groups having 1 to 10 carbon atoms, and a fluorine atom, R 4 represents an aryl group having 6 to 40 carbon atoms, and n represents an integer of 0 to 12, and
wherein as to the polyimide comprising at least one of repeating cis-endo-endo and trans-endo-endo units, a total amount of those repeating units represented by the general formulae (1) and (2) is 90% by mole or more relative to all repeating units.

2. The polyimide according to claim 1 , wherein R 4 in the general formulae (1) and (2) is one of groups represented by the following general formulae (3) to (6):

wherein the formula (5), R 5 represents one selected from the group consisting of a hydrogen atom, a fluorine atom, a methyl group, an ethyl group, and a trifluoromethyl group, and in the formula (6), Q represents one selected from the group consisting of groups represented by the formulae: —O—, —S—, —CO—, —CONH—, —C 6 H 4 —, —COO—, —SO 2 —, —C(CF 3 ) 2 —, —C(CH 3 ) 2 —, —CH 2 —, —O—C 6 H 4 —C(CH 3 ) 2 —C 6 H 4 —O—, —O—C 6 H 4 —SO 2 —C 6 H 4 —O—, —C(CH 3 ) 2 —C 6 H 4 —C(CH 3 ) 2 —, —O—C 6 H 4 —C 6 H 4 —O—, and —O—C 6 H 4 —O—.

3. The polyimide according to claim 1 , wherein the polyimide has a linear expansion coefficient of 15 ppm/° C. or less, the linear expansion coefficient being determined by measuring change in length under a nitrogen atmosphere under a condition of a rate of temperature rise of 5° C./minute in a temperature range from 50° C. to 200° C.

4. The polyimide according to claim 1 , wherein the total amount of the repeating units represented by the general formulae (1) and (2) is 95 to 100% by mole relative to all the repeating units.

5. An alicyclic tetracarboxylic dianhydride used for production of the polyimide according to claim 1 , the alicyclic tetracarboxylic dianhydride comprising at least one of trans-endo-endo-norbornane-2-spiro-α-cycloalkanone-α′-spiro-2″-norbornane-5,5″,6,6″-tetracarboxylic dianhydrides represented by the following general formula (7):

wherein the formula (7), R 1 , R 2 , R 3 , and n have the same meanings as those of R 1 , R 2 , R 3 , and n in the general formulae (1) and (2) and
the cis-endo-endo-norbornane-2-spiro-α-cycloalkanone-α′-spiro-2″-norbornane-5,5″,6,6″-tetracarboxylic dianhydrides represented by the following general formula (8):

wherein
the formula (8), R 1 , R 2 , R 3 , and n have the same meanings as those of R 1 , R 2 , R 3 , and n in the general formulae (1) and (2), and
a total amount of the alicyclic tetracarboxylic dianhydrides represented by the general formulae (7) and (8) is 90% by mole or more.

6. A polyamic acid comprising at least one of repeating units represented by the following general formulae (15) and (16):

wherein the formulae (15) and (16), R 1 , R 2 and R 3 each independently represent one selected from the group consisting of a hydrogen atom, alkyl groups having 1 to 10 carbon atoms, and a fluorine atom, R 4 represents an aryl group having 6 to 40 carbon atoms, and n represents an integer of 0 to 12, and
wherein as to the polyamic acid comprising at least one of repeating cis-endo-endo and trans-endo-endo units, a total amount of those repeating units represented by the general formulae (15) and (16) is 90% by mole or more relative to all repeating units.

7. A polyamic solution comprising the polyamic acid according to claim 6 , and an organic solvent.

8. A polyimide solution comprising the polyimide according to claim 1 , and an organic solvent.

9. A film comprising the polyimide according to claim 1 .

10. A substrate comprising the polyimide according to claim 1 .

11. A liquid crystal orientation film comprising the polyimide according to claim 1 .

12. A flexible printed wiring board comprising the polyimide according to claim 1 .

13. A polyimide coating material comprising the polyimide according to claim 1 .

14. A reflection plate comprising the polyimide according to claim 1 .

15. A coating film comprising the polyimide according to claim 1 .

Assignees

• Jx Nippon Oil & Energy Corp

Inventors

• Komatsu Shinichi
• FUJISHIRO Rieko
• Fujiwara Miki
• Watanabe Daisuke
• Shibashi Akira
• Matsumoto Takaya

Classifications

• C08G73/1007

  from tetracarboxylic acids or derivatives and diamines · CPC title

• C08G73/1078

  wholly aromatic in the diamino moiety · CPC title

• C08G73/10

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

• C08G73/1067 Primary

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

• C07C2603/93

  Spiro compounds · CPC title