IP Library Granted Patent US 7,785,488
Granted Patent B2
US 7,785,488 · App. 11/635,652 · Granted Aug 31, 2010

Lateral oxirane compound and polymer thereof

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Quick Facts
Patent No.
US 7,785,488
App. No.
11/635,652
Granted
Aug 31, 2010
Kind
B2
Abstract

The invention relates to compounds represented by Formula (1): wherein R a is alkyl or the like; R b is hydrogen, alkyl or the like; A is 1,4-cyclohexylene, 1,4-phenylene or the like; Z is a single bond, alkylene or the like; Y is a single bond, alkylene or the like; and m and n are each an integer of approximately 0 to approximately 5.

Claims (51)

1. A compound represented by the following Formula (1):

wherein in Formula (1),

R a is independently hydrogen, halogen, cyano, —CF 3 , —CF 2 H, —CFH 2 , —OCF 3 , —OCF 2 H, —N═C═O, —N═C=S or alkyl having a carbon number of approximately 1 to approximately 20; in the alkyl, optional —CH 2 — may be substituted with —O—, —S—, —SO 2 —, —CO—, —COO—, —OCO—, —CH═CH—, —CF═CF— or —C≡C—, and optional hydrogen may be substituted with halogen, wherein R a is not hydrogen when m+n is 0;

R b is hydrogen or alkyl having a carbon number of approximately 1 to approximately 5;

A is independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydronaphthalene-2,6-diyl, fluorene-2,7-diyl or bicyclo[2.2.2]octane-1,4-diyl; in these rings, optional —CH 2 — may be substituted with —O—, optional —CH═ may be substituted with —N═, and optional hydrogen may be substituted with halogen, alkyl having a carbon number of 1 to 5 or halogenated alkyl having a carbon number of approximately 1 to approximately 5;

Z is independently a single bond or alkylene having a carbon number of approximately 1 to approximately 20; in the alkylene, optional —CH 2 — may be substituted with —O—, —CO—, —COO—, —OCO—, —CH═CH—, —CF═CF— or —C≡C—, and optional hydrogen may be substituted with halogen;

Y is a single bond or alkylene having a carbon number of approximately 1 to approximately 20; in the alkylene, optional —CH 2 — may be substituted with —O—, —CO—, —COO—, —OCO—or —CH═CH—, and optional hydrogen may be substituted with halogen; and

m and n are each an integer of approximately 0 to approximately 5.

2. The compound of claim 1 , wherein in Formula (1), m+n is an integer of 1 to 3.

3. The compound of claim 1 , wherein in Formula (I), m+n is 2.

4. The compound of claim 1 , wherein in Formula (1), R a is independently alkyl having a carbon number of approximately 1 to approximately 10, alkoxy having a carbon number of approximately 1 to approximately 10 or alkenyl having a carbon number of approximately 2 to approximately 10, and of which optional hydrogens thereof may be substituted with fluorine;

R b is hydrogen, methyl or ethyl;

A is independently 1,4-cyclohexylene, 1,4-phenylene, pyridine-2,5-diyl, pyridazine-3,6-diyl or pyrimidine-2,5-diyl, and of which optional hydrogens thereof may be substituted with chlorine, fluorine, alkyl having a carbon number of approximately 1 to approximately 3 or fluoroalkyl having a carbon number of approximately 1 to approximately 3;

Z is independently a single bond, —CH 2 O—, —OCH 2 —, —COO—, —OCO—, —CH═CH—, —(CH 2 ) 2 COO—, —OCO(CH 2 ) 2 —, —CH═CH—COO—, —OCO—CH═CH— or —C═C—;

Y is alkylene having a carbon number of approximately 1 to approximately 10; in the alkylene, optional —CH 2 — may be substituted with —O—, —COO— or —OCO—.

5. A compound represented by any of Formulas (I), (II) and (III):

wherein in Formulas (I), (II) and (III),

R a is independently hydrogen, halogen, cyano, —CF 3 , —CF 2 H, —CFH 2 , —OCF 3 , —OCF 2 H, —N═C═O, —N═C═S or alkyl having a carbon number of approximately 1 to approximately 20; in the alkyl, optional —CH 2 — may be substituted with —O—, —S—, —SO 2 —, —CO—, —COO—, —OCO—, —CH═CH—, —CF═CF— or —C≡C—, and of which optional hydrogen may be substituted with halogen;

R b is hydrogen or alkyl having a carbon number of approximately 1 to approximately 5;

A is independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydronaphthalene-2,6-diyl, fluorene-2,7-diyl or bicyclo[2.2.2]octane-1,4-diyl; in these rings, optional —CH 2 — may be substituted with —O—, optional —CH═ may be substituted with —N═, and optional hydrogen may be substituted with halogen, alkyl having a carbon number of approximately 1 to approximately 5 or halogenated alkyl having a carbon number of approximately 1 to approximately 5;

Z is independently a single bond or alkylene having a carbon number of approximately 1 to approximately 20; in the alkylene, optional —CH 2 — may be substituted with —O—, —CO—, —OCO—, —OCO—, —CH═CH—, —CF═CF— or —C≡C—, and optional hydrogen may be substituted with halogen;

Y is a single bond or alkylene having a carbon number of approximately 1 to approximately 20; in the alkylene, optional —CH 2 — may be substituted with —O—, —CO—, —COO—, —OCO—or —CH═CH—, and optional hydrogen may be substituted with halogen.

6. The compound of claim 5 , wherein in Formulas (I), (II) and (III),

R a is independently alkyl having a carbon number of approximately 1 to approximately 10, alkoxy having a carbon number of approximately 1 to approximately 10 or alkenyl having a carbon number of approximately 2 to approximately 10, and optional hydrogens thereof may be substituted with fluorine;

R b is hydrogen, methyl or ethyl;

A is independently 1,4-cyclohexylene, 1,4-phenylene, pyridine-2,5-diyl, pyridazine-3,6-diyl or pyrimidine-2,5-diyl, and optional hydrogens thereof may be substituted with chlorine, fluorine, alkyl having a carbon number of approximately 1 to approximately 3 or fluoroalkyl having a carbon number of approximately 1 to approximately 3;

Z is independently a single bond, —CH 2 O—, —OCH 2 —, —COO—, —OCO—, —CH═CH—, —(CH 2 ) 2 COO—, —OCO(CH 2 ) 2 —, —CH═CH—COO—, —OCO—CH═CH— or —C═C—;

Y is alkylene having a carbon number of approximately 1 to approximately 10; in the alkylene, optional —CH 2 — may be substituted with —O—, —OCO—or —OCO—.

7. The compound of claim 5 , wherein in Formulas (I), (II) and R a is independently alkyl having a carbon number of approximately 1 to approximately 10 or alkoxy having a carbon number of approximately 1 to approximately 10;

R b is hydrogen;

A is independently 1,4-cyclohexylene or 1,4-phenylene;

Z is independently a single bond, —OCO—, —OCO—, —CH═CH—, —(CH 2 ) 2 COO—, —OCO(CH 2 ) 2 —, —CH═CH—COO—, —OCO—CH═CH— or —C≡C—;

Y is alkylene having a carbon number of approximately 1 to approximately 10; in the alkylene, —CH 2 — adjacent to the ring may be substituted with —O—, —COO— or —OCO—.

8. A composition comprising at least one compound of claim 1 .

9. The composition of claim 8 , further comprising a polymerizable compound which is different from the compounds of claim 1 .

10. The composition of claim 8 , further comprising a polymerizable optically active compound which is different from the compounds of claim 1 .

11. The composition of claim 8 , further comprising a non-polymerizable liquid crystalline compound.

12. The composition of claim 8 , further comprising a non-polymerizable optically active compound.

13. The composition of claim 8 , further comprising a polymerization initiator.

14. The composition of claim 8 , further comprising a solvent.

15. A polymer obtained by polymerizing the composition of claim 8 .

16. The polymer of claim 15 , wherein the weight average molecular weight of said polymer is from approximately 500 to approximately 1,000,000.

17. The polymer of 15 , wherein the weight average molecular weight of said polymer is from approximately 1,000 to approximately 500,000.

18. The polymer of claim 15 , wherein said polymer is optically active.

19. A film comprising the polymer of claim 15 .

20. A molded article having an optical anisotropy comprising the polymer of claim 15 .

21. A liquid crystal display element comprising the composition of claim 8 .

22. A liquid crystal display element comprising the polymer of claim 15 .

23. A liquid crystal display element comprising the film of claim 19 .

24. A liquid crystal display element comprising the molded article having an optical anisotropy of claim 20 .

25. The compound of claim 1 , wherein in Formula (1), m+n is not 0.