IP Library › Granted Patent US 7,527,746
Granted Patent B2
US 7,527,746 · App. 11/315,874 · Granted May 5, 2009

Liquid crystal polyfunctional acrylate derivative and polymer thereof

Assignees: Chisso Corporation; Chisso Petrochemical Corporation
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Quick Facts
Patent No.
US 7,527,746
App. No.
11/315,874
Granted
May 5, 2009
Kind
B2
Abstract

A compound represented by the following general formula (1a) or (1b), a liquid crystal composition containing the compound, and a polymer obtained by polymerizing the compound or the composition: wherein R 1 represents a fluorine atom, an alkyl group or the like; Y 1 and Y 2 each independently represents alkylene or the like; A 1 , A 2 , B 1 and B 2 each independently represents 1,4-cyclohexylene, 1,4-phenylene or the like; X 1 and X 2 each independently represents a single bond, —COO—, —OCO— or the like; m represents 0, 1 or 2; and G represents hydrogen, methyl or the like.

Claims (30)

1. A compound represented by the following general formula (1a) or (1b):

wherein R 1 represents a hydrogen atom, a fluorine atom, a chlorine atom, —CN, —NO 2 or an alkyl group having from 1 to 20 carbon atoms, provided that in the alkyl group, an arbitrary hydrogen atom may be replaced by a fluorine atom or a chlorine atom, and arbitrary one or two —CH 2 — groups may be replaced by —O—, —S—, —COO—, —OCO—, —CO—, —CH═CH— or —C≡C—, in which R 1 may be an optically active group; Y 1 and Y 2 each independently represents an alkylene group having from 1 to 20 carbon atoms, provided that in the alkylene group, an arbitrary hydrogen atom may be replaced by a fluorine atom or a chlorine atom, an arbitrary —CH 2 — may be replaced by —O—, arbitrary one or two —CH 2 — groups may be replaced by —COO— or —OCO—, and arbitrary one —CH 2 — may be replaced by —CH═CH— or —C≡C—, in which Y 1 and Y 2 each may be an optically active group; A 1 , A 2 , B 1 and B 2 each independently represents a group selected from 1,4-cyclohexylene, 1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, tetrahydronaphthalene-2,6-diyl, fluorene-2,7-diyl, 9-methylfluorene-2,7-diyl, 9-ethylfluorene-2,7-diyl, 9,9-dimethylfluorene-2,7-diyl, 9-chlorofluorene-2,7-diyl, 9,9-dichlorofluorene-2,7-diyl, and groups represented by the following formulae (K1), (K2) and (K3), provided that in the 1,4-phenylene group, an arbitrary hydrogen atom may be replaced by a fluorine atom or a chlorine atom, and arbitrary one or two hydrogen atoms may be replaced by a cyano group, a methyl group, a methoxy group, a hydroxyl group, a formyl group, an acetoxy group, an acetyl group, a trifluoroacetyl group, a difluoromethyl group or a trifluoromethyl group; X 1 and X 2 each independently represents a single bond, —COO—, —OCO—, —OCH 2 —, —CH 2 O—, —CONH—, —NHCO—, —CH═CH—COO—, —COO—HC═CH—, —(CH 2 ) 2 —COO—, —OOC—(CH 2 ) 2 —, —(CH 2 ) 2 — or —C≡C—; m represents 0, 1 or 2, provided that when m is 2, two groups represented by A 1 may be the same groups or different groups, and two groups represented by X 1 may be the same groups or different groups; and G represents a hydrogen atom, a fluorine atom, a methyl group, a cyano group or a trifluoromethyl group, provided that a plurality of groups represented by G may be the same groups or different groups:

2. The compound according to claim 1 , wherein in the formulae (1a) and (1b), R 1 represents a fluorine atom, a chlorine atom, —CN, —NO 2 , —OCF 3 , an alkyl group having from 1 to 15 carbon atoms or an alkoxy group having from 1 to 15 carbon atoms; Y 1 and Y 2 each independently represents —O—, —(CH 2 ) r —, —O—(CH 2 ) r —, —(CH 2 ) r —O—, —O—(CH 2 ) r —O— and —O—(CH 2 CH 2 O) s —, wherein r represents an integer of from 1 to 10, and s represents an integer of from 1 to 5; A 1 , A 2 , B 1 and B 2 each independently represents a group selected from 1,4-cyclohexylene, 1,4-phenylene, naphthalene-2,6-diyl, fluorene-2,7-diyl, 9-methylfluorene-2,7-diyl, 9-ethylfluorene-2,7-diyl, 9,9-dimethylfluorene-2,7-diyl, and groups represented by the following formulae (K1), (K2) and (K3), provided that in the 1,4-phenylene group, an arbitrary hydrogen atom may be replaced by a fluorine atom, arbitrary one hydrogen atom may be replaced by a methyl group, a trifluoromethyl group, a methoxy group, an acetoxy group or an acetyl group, and arbitrary two hydrogen atoms may be replaced by a trifluoroacetyl group; X 1 and X 2 each independently represents a single bond, —COO—, —OCO—, —CH═CH—COO—, —OOC—HC═CH—, —(CH 2 ) 2 —COO—, —OOC—(CH 2 ) 2 —, —(CH 2 ) 2 — or —C≡C—; m represents 0 or 1; and G represents a methyl group, a fluorine atom or a hydrogen atom.

3. A compound represented by one of the following general formulae (3) to (6):

wherein R 1 represents —CN, —OCF 3 , an alkyl group having from 1 to 10 carbon atoms or an alkoxy group having from 1 to 10 carbon atoms; A 1 and A 2 each independently represents 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, 2-methyl-1,4-phenylene or 2-trifluoromethyl-1,4-phenylene; B 1 and B 2 each independently represents 1,4-cyclohexylene, 1,4-phenylene, naphthalene-2,6-diyl, fluorene-2,7-diyl, 9-methylfluorene-2,7-diyl, 9-ethylfluorene-2,7-diyl, 9,9-dimethylfluorene-2,7-diyl, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,3,5,6-tetrafluoro-1,4-phenylene, 2-methyl-1,4-phenylene, 2-trifluoromethyl-1,4-phenylene, 2-methoxy-1,4-phenylene, 2-acetyl-1,4-phenylene or 2,3-ditrifluoromethyl-1,4-phenylene; X 1 and X 2 each independently represents a single bond, —COO—, —OCO—, —CH═CH—COO—, —OOC—HC═CH—, —(CH 2 ) 2 —COO—, —OOC—(CH 2 )2—, —(CH 2 ) 2 — or —C≡C—; X 3 represents a single bond or —O—; and q represents an integer of from 0 to 10, provided that a plurality of groups represented by X 3 may be the same groups or different groups, and a plurality of integers represented by q may be the same or different.

4. The compound according to claim 3 , wherein in the formulae (3) to (6), R 1 represents —CN, —OCF 3 , an alkyl group having from 1 to 10 carbon atoms or an alkoxy group having from 1 to 10 carbon atoms; A 1 and A 2 each independently represents 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene or 2-methyl-1,4-phenylene; B 1 and B 2 each independently represents 1,4-cyclohexylene, 1,4-phenylene, 9-methylfluorene-2,7-diyl, 9,9-dimethylfluorene-2,7-diyl, 2-fluoro-1,4-phenylene, 2-methyl-1,4-phenylene, 2-trifluoromethyl-1,4-phenylene or 2,3-ditrifluoromethyl-1,4-phenylene; X 1 and X 2 each independently represents a single bond, —COO— or —OCO—; X 3 represents a single bond or —O—; and q represents an integer of from 0 to 10.

5. The compound according to claim 3 , wherein the compound is represented by the formula (3), and in the formula (3), R 1 represents —CN; A 2 represents 1,4-phenylene; B 1 represents 1,4-phenylene; X 2 represents a single bond; X 3 represents a single bond or —O—; and q represents an integer of from 0 to 10.

6. The compound according to claim 3 , wherein the compound is represented by the formula (5), and in the formula (5), A 2 represents 1,4-phenylene; B 2 represents 1,4-phenylene; X 2 represents —COO—; X 3 represents a single bond or —O—; and q represents an integer of from 0 to 10.

7. The compound according to claim 3 , wherein the compound is represented by the formula (6), and in the formula (6), A 1 and A 2 each represents 1,4-phenylene; B 2 represents 1,4-phenylene, 9-methylfluorene-2,7-diyl or 2-methyl-1,4-phenylene; X 1 and X 2 each independently represents —COO— or —OCO—; X 3 represents a single bond or —O—; and q represents an integer of from 0 to 10.

8. A composition comprising, as a first component, at least one of the compound according to claim 1 .

9. A composition comprising, as a first component, at least one of the compound according to claim 3 .

10. The composition according to claim 9 , wherein the composition further comprises, as a second component, a polymerizable compound that is different from the compounds according to claim 1 .

11. The composition according to claim 10 , wherein the second component is at least one compound selected from the group consisting of compounds represented by the following formulae (M1), (M2) and (M3):

wherein B 3 represents 1,4-phenylene, 2-fluoro-1,4-phenylene, 2-methyl-1,4-phenylene, 2-trifluoromethyl-1,4-phenylene, 2,3-ditrifluoro-1,4-phenylene, naphthalene-2,6-diyl, 9-methylfluorene-2,7-diyl, 9-ethylfluorene-2,7-diyl or 9,9-dimethylfluorene-2,7-diyl; R 2 represents a fluorine atom, —OCF 3 , —CN, an alkyl group having from 1 to 20 carbon atoms or an alkoxy group having from 1 to 20 carbon atoms; X 5 each independently represents a single bond, —(CH 2 ) 2 — or —C═C—; X 6 represents a single bond, —COO—, —OCO—, —CH═CH—COO—, —OOC—HCαCH— or —C≡C—; p and t each independently represents an integer of from 1 to 20; G 2 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group; W 1 , W 2 , W 3 , W 4 and W 5 each independently represents a hydrogen atom or a fluorine atom; and W 6 and W 7 each independently represents a hydrogen atom or a methyl group, provided that a carbon atoms attached with an asterisk is a asymmetric carbon atom, a plurality of groups represented by X 5 may be the same groups or different groups, a plurality of integers represented by t may be the same or different, and a plurality of groups represented by G 2 may be the same groups or different groups.

12. The composition according to claim 11 , wherein the composition comprises,

as the first component, at least one compound selected from the group consisting of the compound represented by the formula (6) according to claim 3 , in the formula (6), A 1 and A 2 each represents 1,4-phenylene; B 2 represents 1,4-phenylene, 9-methylfluorene-2,7-diyl or 2-methyl-1,4-phenylene; X 1 and X 2 each independently represents —COO— or —OCO—; X 3 represents a single bond or —O—; and q represents an integer of from 0 to 10, and

as the second component, at least one compound selected from the group consisting of the compound represented by the formula (M1), in the formula (M1), B 3 represents 1,4-phenylene, 2-methyl-1,4-phenylene, 2,3-ditrifluoro-1,4-phenylene, 9-methylfluorene-2,7-diyl or 9,9-dimethylfluorene-2,7-diyl; X 5 represents a single bond or —(CH 2 ) 2 —; p and t each independently represents an integer of from 1 to 20; G 2 represents a hydrogen atom; and W 1 , W 2 , W 3 and W 4 each independently represents a hydrogen atom or a fluorine atom, and

a content of the first component is from 20 to 80% by weight, and a content of the second component is from 20 to 80% by weight, with respect to a total amount of the first and second components being 100% by weight.

13. The composition according to claim 11 , wherein the composition comprises,

as the first component, at least one compound selected from the group consisting of the compound represented by the formula (6) according to claim 3 , in the formula (6), A 1 and A 2 each represents 1,4-phenylene; B 2 represents 1,4-phenylene, 9-methylfluorene-2,7-diyl or 2-methyl-1,4-phenylene; X 1 and X 2 each independently represents —COO— or —OCO—; X 3 represents a single bond or —O—; and q represents an integer of from 0 to 10, and

as the second component, at least one compound selected from the group consisting of the compound represented by the formula (M3), in the formula (M3), G 2 represents a hydrogen atom; and W 6 and W 7 each independently represents a hydrogen atom or a methyl group, and

a content of the first component is from 20 to 80% by weight, and a content of the second component is from 20 to 80% by weight, with respect to a total amount of the first and second components being 100% by weight.

14. A polymer obtained by polymerizing the compound according to claim 1 .

15. A polymer obtained by polymerizing the composition according to claim 8 .

16. A molded article having optical anisotropy comprising the polymer according to claim 14 .

17. A liquid crystal display device comprising the molded article according to claim 16 .

18. Use of the polymer according to claim 14 as a molded article having optical anisotropy.

19. A molded article having optical anisotropy comprising the polymer according to claim 15 .

20. A liquid crystal display device comprising the molded article according to claim 19 .

21. Use of the polymer according to claim 15 as a molded article having optical anisotropy.

Assignments (3)
CHANGE OF NAME Recorded Jun 1, 2012
From: CHISSO PETROCHEMICAL CORPORATION
To: JNC PETROCHEMICAL CORPORATION
Reel/Frame 028300/0565 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 2, 2011
From: CHISSO CORPORATION
To: JNC CORPORATION
Reel/Frame 026207/0653 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 22, 2005
From: SYUNDO, RYUSHI
To: CHISSO CORPORATION; CHISSO PETROCHEMICAL CORPORATION
Reel/Frame 017410/0391 →
Priority Claims (1)
JP 2005-020955 · Jan 28, 2005 · national
Continuity (1)
Related Publication 20060172090A1 · Aug 3, 2006