IP Library Granted Patent US 7,919,009
Granted Patent B2
US 7,919,009 · App. 12/519,865 · Granted Apr 5, 2011

Polymerizable compounds and polymerizable compositions

Assignee: Adeka Corporation
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Quick Facts
Patent No.
US 7,919,009
App. No.
12/519,865
Granted
Apr 5, 2011
Kind
B2
Abstract

A polymerizable compound represented by general formula (1) of the invention has good solvent solubility and excellent alignment control properties and optical characteristics. In formula (1), M 1 and M 2 are each hydrogen or methyl; X 1 and X 2 are each a single bond, or an optionally branched C1-10 alkylene, alkyleneoxy or alkyleneoxycarbonyloxy; X 3 is optionally branched C1-10 alkylene; Y 1 and Y 2 are each an ester linkage, etc.; and rings A, B, C, and D are each a cyclic structure, such as 2,6-naphthlene.

Claims (39)

1. A polymerizable compound represented by general formula (1):

wherein

M 1 and M 2 each independently represent a hydrogen atom or a methyl group;

X 1 and X 2 each independently represent a single bond, an optionally branched alkylene group having 1 to 10 carbon atoms, an optionally branched alkyleneoxy group having 1 to 10 carbon atoms bonded to the adjacent ring at the oxygen atom thereof, or an optionally branched alkyleneoxycarbonyloxy group having 1 to 10 carbon atoms;

X 3 represents an optionally branched alkylene group having 1 to 10 carbon atoms, the —CH 2 — moiety of which may be displaced with an oxygen atom, provided that no two oxygen atoms are adjacent to each other;

Y 1 and Y 2 each independently represent a linking group selected from a single bond, an ester linkage, an ether linkage, an optionally branched alkylene group having 2 to 8 carbon atoms which may have an unsaturated bond, and a combination thereof; and

rings A, B, C, and D each independently represent a cyclic structure selected from the group consisting of 1,4-phenylene, 1,4-cyclohexylene, and 2,6-naphthylene, the cyclic structure being optionally substituted with a substituent selected from a halogen atom, an optionally branched alkyl group having 1 to 10 carbon atoms, an optionally branched alkoxy group having 1 to 10 carbon atoms, —CO—O—R 1 , —CO—R 2 , or —O—CO—R 3 , wherein R 1 , R 2 , and R 3 each represent an optionally branched alkyl group having 1 to 10 carbon atoms.

2. The polymerizable compound according to claim 1 , wherein at least one of the cyclic structures represented by rings A, B, C, and D is 2,6-naphthylene.

3. The polymerizable compound according to claim 1 , wherein Y 1 and Y 2 are each —CO—O— or —O—CO—.

4. A polymerizable composition comprising the polymerizable compound according to claim 1 .

5. The polymerizable composition according to claim 4 , further comprising at least one liquid crystal compound.

6. The polymerizable composition according to claim 5 , wherein the polymerizable compound is present in an amount of 1 to 30 parts by mass per 100 parts by mass of the sum of the polymerizable compound and the liquid crystal compound.

7. The polymerizable composition according to claim 5 , wherein the liquid crystal compound is represented by general formula (2):

wherein

M 3 and M 4 each independently represent a hydrogen atom, a halogen atom, or a methyl group;

X 4 and X 5 each independently represent a single bond, an optionally branched alkylene group having 1 to 10 carbon atoms, an optionally branched alkyleneoxy group having 1 to 10 carbon atoms bonded to the adjacent ring at the oxygen atom thereof, or an optionally branched alkyleneoxycarbonyloxy group having 1 to 10 carbon atoms;

Y 3 and Y 4 each independently represent a linking group selected from a single bond, an ester linkage, an ether linkage, an optionally branched alkylene group having 2 to 8 carbon atoms which may have an unsaturated bond, and a combination thereof; and

rings E, F, and G each independently represent a cyclic structure selected from the group consisting of 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexenylene, and 2,6-naphthylene, the cyclic structure being optionally substituted with a substituent selected from a halogen atom, an optionally branched alkyl group having 1 to 10 carbon atoms, an optionally branched alkoxy group having 1 to 10 carbon atoms, —CO—O—R 4 , —O—CO—R 5 , and —CO—R 6 , wherein R 4 , R 5 , and R 6 each represent an optionally branched alkyl group having 1 to 10 carbon atoms;

m represents an integer of 0 to 3; and

when m is 2 or greater, the Y 4 s and the rings G may be the same or different.

8. The polymerizable composition according to claim 4 , further comprising a radical polymerization initiator.

9. A polymer obtained by photopolymerizing the polymerizable composition according to claim 4 .

10. An optical film for a display device, which is formed of the polymer according to claim 9 .

11. The polymerizable compound according to claim 2 , wherein Y 1 and Y 2 are each —CO—O— or —O—CO—.

12. A polymerizable composition comprising the polymerizable compound according to claim 2 .

13. A polymerizable composition comprising the polymerizable compound according to claim 4 .

14. The polymerizable composition according to claim 6 , wherein the liquid crystal compound is represented by general formula (2):

wherein

M 3 and M 4 each independently represent a hydrogen atom, a halogen atom, or a methyl group;

X 4 and X 5 each independently represent a single bond, an optionally branched alkylene group having 1 to 10 carbon atoms, an optionally branched alkyleneoxy group having 1 to 10 carbon atoms bonded to the adjacent ring at the oxygen atom thereof, or an optionally branched alkyleneoxycarbonyloxy group having 1 to 10 carbon atoms;

Y 3 and Y 4 each independently represent a linking group selected from a single bond, an ester linkage, an ether linkage, an optionally branched alkylene group having 2 to 8 carbon atoms which may have an unsaturated bond, and a combination thereof; and

rings E, F, and G each independently represent a cyclic structure selected from the group consisting of 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexenylene, and 2,6-naphthylene, the cyclic structure being optionally substituted with a substituent selected from a halogen atom, an optionally branched alkyl group having 1 to 10 carbon atoms, an optionally branched alkoxy group having 1 to 10 carbon atoms, —CO—O—R 4 , —O—CO—R 5 , and —CO—R 6 , wherein R 4 , R 5 , and R 6 each represent an optionally branched alkyl group having 1 to 10 carbon atoms;

m represents an integer of 0 to 3; and when m is 2 or greater, the Y 4 s and the rings G may be the same or different.

15. The polymerizable composition according to claim 5 , further comprising a radical polymerization initiator.

16. The polymerizable composition according to claim 6 , further comprising a radical polymerization initiator.

17. The polymerizable composition according to claim 7 , further comprising a radical polymerization initiator.

18. A polymer obtained by photopolymerizing the polymerizable composition according to claim 5 .

19. A polymer obtained by photopolymerizing the polymerizable composition according to claim 6 .

20. A polymer obtained by photopolymerizing the polymerizable composition according to claim 7 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 21, 2018
From: CORPORATION, ADEKA
To: DIC CORPORATION
Reel/Frame 045864/0779 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 18, 2009
From: ITANO, KAZUYUKI; FUKUNAGA, HIROYA; IRISAWA, MASATOMI; KOBAYASHI, TATSUNORI; HASEGAWA, MINEKI
To: ADEKA CORPORATION
Reel/Frame 022842/0973 →
Priority Claims (1)
JP 2007-086364 · Mar 29, 2007 · national
Continuity (1)
Related Publication 20100032621A1 · Feb 11, 2010