Liquid crystal composition and liquid crystal optical device

• US 9,976,087 B2
• Filed: 07/11/2016
• Issued: 05/22/2018
• Est. Priority Date: 08/06/2015
• Status: Active Grant

• Current Assignee: AGC, Inc.
• Original Assignee: Asahi Glass Company, Limited (AGC, Inc.)
• Inventors: Niiyama, Satoshi, Kawakami, Remi
• Primary Examiner(s): Visconti, Geraldina
• Application Number:
  US15/206,740
• Publication Number:
  US 20170037317A1
• Time in Patent Office: 680 Days
• Field of Search: 25229901, 428 11
• CPC Class Codes: C09K 19/56 Aligning agents
• CPC Class Codes: C09K 2019/0448 the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
• CPC Class Codes: G02F 1/133302 Rigid substrates, e.g. inorganic substrates
• CPC Class Codes: G02F 1/133365 Cells in which the active layer comprises a liquid crystalline polymer
• CPC Class Codes: G02F 1/133723 Polyimide, polyamide-imide
• CPC Class Codes: G02F 1/133742 for homeotropic alignment
• CPC Class Codes: G02F 1/13398 Spacer materials; Spacer properties
• CPC Class Codes: G02F 2201/124 interdigital

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

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);

A¹-(OR¹)_n—

O—

Z—

O—

(R²O)_m-A²  

 

Formula (1)

where A¹ and A² are each independently an acryloyl group, a methacryloyl group, a glycidyl group or an allyl group, R¹ and R² 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);

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) A³ to A⁵ 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.

8. The liquid crystal composition according to claim 1, wherein in the formula (2) R³ is

—

R⁴—

or

(R⁵—

O)_n—

R⁵—

where R⁴ is a C_2-20linear or branched alkylene group, R⁵ 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 R³ is —

R⁴—

where R⁴is a C_2-20 linear alkylene group.

10. The liquid crystal composition according to claim 8, wherein R³is (R⁵—

O)_n—

R⁵—

where R⁵ is —

(CH₂)_s—

, —

CH₂—

CH(CH₃)—

, —

CH₂—

CH₂—

CH(CH₃)—

or —

CH₂—

CH₂—

C(CH₃)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 A³-R³-A⁴.

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):

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);

A¹-(OR¹)_n—

O—

Z—

O—

(R²O)_m-A² 

 

Formula (1)

where A¹ and A² are each independently an acryloyl group, a methacryloyl group, a glycidyl group or an allyl group, R¹ and R² 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);

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.

13. The liquid crystal optical device according to claim 6, wherein in the formula (2) R³ is

—

R⁴—

or

(R⁵—

O)_n—

R⁵—

where R⁴ is a C_2-20 linear or branched alkylene group, R⁵ 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 R³ is —

R⁴—

where R⁴ is a C_2-20 linear alkylene group.

15. The liquid crystal optical device according to claim 13, wherein R³ is (R⁵—

O)_n—

R⁵—

where R⁵ is —

(CH₂)_s—

, —

CH₂—

(CH₃)—

, —

CH₂—

CH₂—

CH(CH₃)—

or —

CH₂—

CH₂—

C(CH₃)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 A³-R³-A⁴.