IP Library Granted Patent US 9,976,087
Granted Patent B2
US 9,976,087 · App. 15/206,740 · Granted May 22, 2018

Liquid crystal composition and liquid crystal optical device

Inventors: Satoshi Niiyama (Chiyoda-ku, JP); Remi Kawakami (Chiyoda-ku, JP)
Assignee: Asahi Glass Company, Limited
C09K19/56C09K2019/0448G02F1/133365G02F1/133723G02F2001/13398G02F2001/133302G02F2001/133742G02F2201/124
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Quick Facts
Patent No.
US 9,976,087
App. No.
15/206,740
Granted
May 22, 2018
Kind
B2
Abstract

To provide a high quality liquid crystal optical device irrespective of the size of the liquid crystal optical device, while simplifying the production process, and a liquid crystal composition suitable for such a liquid crystal optical device. The liquid crystal composition of the present invention is a liquid crystal composition comprising a liquid crystal compound which shows liquid crystallinity and which is a non-curable compound, a liquid crystalline curable compound having a polymerizable functional group, and a non-liquid crystalline curable compound having a polymerizable functional group, wherein the content of the non-liquid crystalline curable compound is larger than the content of the liquid crystalline curable compound, and the total amount of the liquid crystalline curable compound and the non-liquid crystalline curable compound is at least 8 mass % and less than 20 mass % of the entirety.

Claims (50)

1. A liquid crystal composition, comprising:

a liquid crystal compound which shows liquid crystallinity and which is a non-curable compound;

a liquid crystalline curable compound having a polymerizable functional group; and

at least one non-liquid crystalline curable compound having a polymerizable functional group,

wherein the non-liquid crystalline curable compound is included at a content larger than a content of the liquid crystalline curable compound,

the liquid crystalline curable compound and the non-liquid crystalline curable compound are included in a total amount of at least 8 mass% and less than 20 mass% with respect to an entire amount of the liquid crystal composition,

the at least one non-liquid crystalline curable compound comprises a compound of formula (1):

A 1 -(OR 1 ) n —O—Z—O—(R 2 O) m -A 2   Formula (1)

where A 1 and A 2 are each independently an acryloyl group, a methacryloyl group, a glycidyl group or an allyl group, R 1 and R 2 are each independently a C 2-6 alkylene group, Z is a divalent mesogenic structure moiety, and n and m are each independently an integer of from 1 to 10, and

the non-liquid crystalline curable compound further includes a compound of formula (2):

where A 3 to A 5 are each independently an acryloyloxy group, a methacryloyloxy group, a vinyl ether group, a vinyl group or a glycidyl ether group, R 3 is a linear or branched C 1-50 mono- to tri-valent organic group which may have one or more etheric oxygen atoms between carbon atoms, and p, q and r are each independently from 0 to 3, provided p+q+r=1 to 3.

2. The liquid crystal composition according to claim 1 , wherein

in the formula (1) n and m are each independently an integer of from 1 to 4.

3. The liquid crystal composition according to claim 2 , wherein

in the formula (2) A 3 to A 5 are each independently an acryloyloxy group, a methacryloyloxy group, or a vinyl ether group.

4. The liquid crystal composition according to claim 1 , wherein the liquid crystalline curable compound is included at a content of less than 10 mass% of the total amount of the liquid crystal composition.

5. The liquid crystal composition according to claim 1 , wherein the liquid crystalline curable compound is a bifunctional curable compound.

6. A liquid crystal optical device, comprising:

a pair of substrates, at least one of which is transparent;

an electrooptical functional layer sandwiched between the pair of substrates; and

an electric field applying device configured to generate an electric field in the electrooptical functional layer,

wherein the electrooptical functional layer includes a liquid crystal compound and an alignment controlling material which controls an alignment of the liquid crystal compound,

the alignment controlling material is included in an amount of at least 8 mass % and less than 20 mass % based on an entire electrooptical functional layer, and the alignment controlling material includes one derived from a non-liquid crystalline curable compound at a larger proportion than one derived from a liquid crystalline curable compound,

the at least one non-liquid crystalline curable compound comprises a compound of formula (1):

A 1 -(OR 1 ) n —O—Z—O—(R 2 O) m -A 2   Formula (1)

where A 1 and A 2 are each independently an acryloyl group, a methacryloyl group, a glycidyl group or an allyl group, R 1 and R 2 are each independently a C 2-6 alkylene group Z is a divalent mesogenic structure moiety, and n and m are each independently an integer of from 1 to 10, and

the non-liquid crystalline curable compound further includes a compound of formula (2):

where A 3 to A 5 are each independently an acryloyloxy group, a methacryloyloxy group, a vinyl ether group, a vinyl group or a glycidyl ether group, R 3 is a linear or branched C 1-50 mono- to tri-valent organic group which may have one or more etheric oxygen atoms between carbon atoms, and p, q and r are each independently from 0 to 3, provided p+q+r=1 to 3.

7. The liquid crystal optical device according to claim 6 , which exhibits a transparent state when no voltage is applied and exhibits a state to scatter incident light when a voltage is applied.

8. The liquid crystal composition according to claim 1 , wherein in the formula (2) R 3 is

—R 4 — or

(R 5 —O) n —R 5 —

where R 4 is a C 2-20 linear or branched alkylene group, R 5 is a C 2-8 linear or branched alkylene group, and n is an integer of from 1 to 10.

9. The liquid crystal composition according to claim 8 , wherein R 3 is —R 4 — where R 4 is a C 2-20 linear alkylene group.

10. The liquid crystal composition according to claim 8 , wherein R 3 is (R 5 —O) n —R 5 — where R 5 is —(CH 2 ) s —, —CH 2 —CH(CH 3 )—, —CH 2 —CH 2 —CH(CH 3 )— or —CH 2 —CH 2 —C(CH 3 ) 2 —, and s is an integer of from 2 to 5.

11. The liquid crystal composition according to claim 10 , wherein n is an integer of from 1 to 6.

12. The liquid crystal composition according to claim 1 , wherein the compound of formula (2) has a formula of A 3 -R 3 -A 4 .

13. The liquid crystal optical device according to claim 6 , wherein in the formula (2) R 3 is

—R 4 — or

(R 5 —O) n —R 5 —

where R 4 is a C 2-20 linear or branched alkylene group, R 5 is a C 2-8 linear or branched alkylene group, and n is an integer of from 1 to 10.

14. The liquid crystal optical device according to claim 13 , wherein R 3 is —R 4 — where R 4 is a C 2-20 linear alkylene group.

15. The liquid crystal optical device according to claim 13 , wherein R 3 is (R 5 —O) n —R 5 — where R 5 is —(CH 2 ) s —, —CH 2 —(CH 3 )—, —CH 2 —CH 2 —CH(CH 3 )— or —CH 2 —CH 2 —C(CH 3 ) 2 —, and s is an integer of from 2 to 5.

16. The liquid crystal optical device according to claim 15 , wherein n is an integer of from 1 to 6.

17. The liquid crystal optical device according to claim 6 , wherein the compound of formula (2) has a formula of A 3 -R 3 -A 4 .

18. The liquid crystal composition according to claim 1 , wherein the compound of formula (2) is a compound of one of Formulas (7) to (11):

19. The liquid crystal composition according to claim 1 , wherein the liquid crystalline curable compound is a compound of one of Formulas (12) to (28):

20. The liquid crystal composition according to claim 1 , wherein the at least one non-liquid crystalline curable compound comprises at least one of a compound of formula (a) and a compound of formula (d):

and

the liquid crystalline curable compound is a compound of formula (b) or a compound of formula (c):

Assignments (2)
CHANGE OF NAME Recorded Aug 7, 2018
From: ASAHI GLASS COMPANY, LIMITED
To: AGC INC.
Reel/Frame 046730/0786 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 11, 2016
From: NIIYAMA, SATOSHI; KAWAKAMI, REMI
To: ASAHI GLASS COMPANY, LIMITED
Reel/Frame 039123/0451 →
Priority Claims (1)
JP 2015-155776 · Aug 6, 2015 · national
Continuity (1)
Related Publication 20170037317A1 · Feb 9, 2017