Liquid crystal composition, liquid crystal display device including the same, and method of manufacturing liquid crystal display device

1. A liquid crystal composition, comprising:

a liquid crystal compound; and

a liquid crystal aligning agent comprising at least one compound represented by Formula 1:

wherein in Formula 1,

X—* is a C 1-20 -alkyl-*,

-L 1 -* is a single bond, *—(CH 2 ) p1 —*, *—O(CH 2 ) p1 —*, *—O—*,

*—CH═CH—*, or *—C≡C—*, wherein p1 is an integer of 1 to 10;

-L 2 -* is a single bond, *—(CH 2 ) p2 —*, *—O(CH 2 ) p2 —*, *—O—*,

*—CH═CH—*, or *—C≡C—*, wherein p2 is an integer of 1 to 10;

-L 3 -* is a single bond, *—(CH 2 ) p3 —*, *—O(CH 2 ) p3 —*, *—O—*,

*—CH═CH—*, or *—C≡C—*, wherein p3 is an integer of 1 to 10;

*-L 1 -*, *-L 2 -*, and *-L 3 -* are identical to or different from one another;

*—C—* is a substituted or unsubstituted cyclic linking group, which is substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

or substituted or unsubstituted

wherein at least one hydrogen in the substituted cyclic linking group is substituted with a C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or a C 1-10 -((meth)acryloxy)alkyl-*;

*—R—* is *—(CH 2 ) q —*, *—O(CH 2 ) q —*, *—(CH 2 ) q Arn-*, or *—O(CH 2 ) q Arn-*, wherein Arn is a substituted or unsubstituted C 6-30 arylene and q is an integer of 1 to 10, wherein at least one hydrogen in the substituted C 6-30 arylene is substituted with a C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or a C 1-10 -((meth)acryloxy)alkyl-*;

*—Y is

wherein n is an integer of 0 to 5;

n 1 is an integer of 1 to 3,

n 2 and m are each independently 0 or 1, and

“*” indicates a point of attachment.

2. The liquid crystal composition of claim 1 ,

wherein X—* is a C 1-20 -alkyl-*, and

wherein the liquid crystal composition further comprises a reactive mesogen comprising at least one compound represented by Formula 2:

P1-SP1-MG-SP2-P2  Formula 2

wherein in Formula 2,

P1-* and *—P2 are each independently

—SP1-* is

and *—SP2-* is

wherein a and b are independently an integer of 0 to 2, each *-L-* is independently *—(CH 2 ) c —*, *—O(CH 2 ) c —*,

*—CH═CH—*, or *—C≡C—*, wherein c is an integer of 1 to 10, *—Z—* is *—(CH 2 ) d —*, wherein d is an integer of 0 to 12, and *—Ar—* is

wherein each A-* is independently H—*, a C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or *—CN; and

*-MG-* is

wherein each A-* is independently H—*, a C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or *—CN.

3. The liquid crystal composition of claim 2 ,

wherein the liquid crystal aligning agent comprises at least one compound represented by Formulae SA 1-1 to SA 1-21:

4. The liquid crystal composition of claim 1 ,

wherein the liquid crystal aligning agent comprises the compound represented by Formula 1,

wherein X—* is

and

wherein the liquid crystal composition does not contain a reactive mesogen having a structure represented by Formula 2:

P1-SP1-MG-SP2-P2  Formula 2

wherein in Formula 2,

P1-* and *—P2 are each independently

—SP1-* is

and *—SP2-* is

wherein a and b are independently an integer of 0 to 2, each *-L-* is independently *—(CH 2 ) c —*, *—O(CH 2 ) c —*,

*—CH═CH—*, or *—C≡C—*, wherein c is an integer of 1 to 10, *—Z—* is *(CH 2 ) d —*, wherein d is an integer of 0 to 12, and *—Ar—* is

wherein each A-* is independently H—*, a C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or *—CN; and

*-MG-* is

wherein each A-* is independently H—*, a C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or *—CN.

5. The liquid crystal composition of claim 4 ,

wherein the liquid crystal aligning agent comprises at least one compound represented by Formulae SA 2-1 to SA 2-17:

6. A liquid crystal display device, comprising:

a first electrode;

a second electrode facing the first electrode;

a liquid crystal layer comprising a liquid crystal compound, wherein the liquid crystal layer is disposed between the first electrode and the second electrode;

a liquid crystal aligning agent comprising at least one compound represented by Formula 1-1, wherein the liquid crystal layer is adsorbed on a surface of at least one of the first electrode and the second electrode to align the liquid crystal compound; and

a polymer of reactive mesogen comprising two or more compounds represented by Formula 2, wherein the polymer of reactive mesogen is adsorbed on the surface of at least one of the first electrode and the second electrode to align the liquid crystal compound:

wherein in Formula 1-1,

X′—* is a C 1-20 -alkyl-*;

*-L 1 -* is a single bond, *—(CH 2 ) p1 —*, *—O(CH 2 ) p1 —*, *—O—*,

*—CH═CH—*, or *—C≡C—*, wherein p1 is an integer of 1 to 10;

*-L 2 -* is a single bond, *—(CH 2 ) p2 —*, *—O(CH 2 ) p2 —*, *—O—*,

*—CH═CH—*, or *—C≡C—*, wherein p2 is an integer of 1 to 10;

*-L 3 -* is a single bond, *—(CH 2 ) p3 —*, *—O(CH 2 ) p3 —*, *—O—*,

*—CH═CH—*, or *—C≡C—*, wherein p3 is an integer of 1 to 10;

*-L 1 -*, *-L 2 -*, and *-L 3 -* are identical to or different from one another;

*—C—* is a substituted or unsubstituted cyclic linking group, which is substituted or unsubstituted

substituted or unsubstituted

substituted or

unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

or substituted or unsubstituted

wherein at least one hydrogen in the substituted cyclic linking group is substituted with a C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or C 1-10 -((meth)acryloxy)alkyl-*;

*—R—* is *—(CH 2 ) q —*, *—O(CH 2 ) q —*, *—(CH 2 ) q Arn-*, or *—O(CH 2 ) q Arn-*, wherein Arn is a substituted or unsubstituted C 6-30 arylene, and q is an integer of 1 to 10, wherein at least one hydrogen in the substituted C 6-30 arylene is substituted with a C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or a C 1-10 -((meth)acryloxy)alkyl-*;

*—Y is

wherein n is an integer of 0 to 5;

n 1 is 1, and

n 2 and m are each independently 0 or 1;

P1-SP1-MG-SP2-P2  Formula 2

wherein in Formula 2,

P1-* and *—P2 are each independently

—SP1-* is

and *—SP2-* is

wherein a and b are independently an integer of 0 to 2, each *-L-* is independently *—(CH 2 ) c —*, *—O(CH 2 ) c —*,

*—CH═CH—*, or *—C≡C—*, wherein c is an integer of 1 to 10, *—Z—* is *—(CH 2 ) d —*, wherein d is an integer of 0 to 12, and *—Ar—* is

wherein each A-* is independently H—*, a C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or *—CN;

*-MG-* is

wherein each A-* is independently H—*, a C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or *—CN; and

“*” indicates a point of attachment.

7. The liquid crystal display device of claim 6 ,

wherein the liquid crystal aligning agent comprises at least one compound represented by Formulae SA 1-1 to SA 1-21:

8. A liquid crystal display device, comprising:

a first electrode;

a second electrode facing the first electrode;

a liquid crystal layer comprising a liquid crystal compound, wherein the liquid crystal layer is disposed between the first electrode and the second electrode; and

a polymer of a liquid crystal aligning agent comprising two or more compounds represented by Formula 1-2, wherein the polymer of liquid crystal aligning agent is adsorbed on a surface of at least one of the first electrode and the second electrode to align the liquid crystal compound,

wherein the liquid crystal layer does not contain a compound represented by Formula 2:

wherein in Formula 1-1,

X″—* is

L 1 -* is a single bond, *—(CH 2 ) p1 —*, *—O(CH 2 ) p1 —*, *—O(CH 2 ) p1 O—*, *—O—*,

*—CH═CH—*, or *—C≡C—*, wherein p1 is an integer of 1 to 10;

*-L 2 -* is a single bond, *—(CH 2 ) p2 —*, *—O(CH 2 ) p2 —*, *—O—*,

*—CH═CH—*, or *—C≡C—*, wherein p2 is an integer of 1 to 10;

*-L 3 -* is a single bond, *—(CH 2 ) p3 —*, *—O(CH 2 ) p3 —*,

*—CH═CH—*, or *—C≡C—*, wherein p3 is an integer of 1 to 10;

*-L 1 -*, *-L 2 -*, and *-L 3 -* are identical to or different from one another;

*—C—* is a substituted or unsubstituted cyclic linking group, which is substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

substituted or unsubstituted

or substituted or unsubstituted

wherein at least one hydrogen in the substituted cyclic linking group is substituted with a C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or a C 1-10 -((meth)acryloxy)alkyl-*;

*—R—* is *—(CH 2 ) q —*, *—O(CH 2 ) q —*, *—(CH 2 ) q Arn-*, or *—O(CH 2 ) q Arn-*, wherein Arn is a substituted or unsubstituted C 6-30 arylene, and q is an integer of 1 to 10; wherein at least one hydrogen in the substituted C 6-30 arylene is substituted with a C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or a C 1-10 -((meth)acryloxy)alkyl-*;

*—Y is

wherein n is an integer of 0 to 5;

n 1 is an integer of 1 to 3, and

n 2 and m are each independently 0 or 1,

P1-SP1-MG-SP2-P2  Formula 2

wherein in Formula 2,

P1-* and *—P2 are each independently

—SP1-* is

and *—SP2-* is

wherein a and b are independently an integer of 0 to 2, each *-L-* is independently *—(CH 2 ) c —*, *—O(CH 2 ) c —*,

*—CH═CH—*, or *—C≡C—*, wherein c is an integer of 1 to 10, *—Z—* is *—(CH 2 ) d —*, wherein d is an integer of 0 to 12, and *—Ar—* is

wherein each A-* is independently H—*, a C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or *—CN;

*-MG-* is

wherein each A-* is independently H—*, a C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or *—CN; and

“*” indicates a point of attachment.

9. The liquid crystal display device of claim 8 ,

wherein the liquid crystal aligning agent comprises at least one compound represented by Formulae SA 2-1 to SA 2-17:

10. A method of manufacturing a liquid crystal display device, comprising:

disposing the liquid crystal composition of claim 1 between a first electrode and a second electrode facing the first electrode to manufacture a liquid crystal cell; and

irradiating the liquid crystal cell with ultraviolet light while applying a voltage to the liquid crystal cell.

11. The method of claim 10 ,

wherein the liquid crystal aligning agent comprises the compound represented by Formula 1, wherein in Formula 1 X—* is a C 1-20 -alkyl-*, and

wherein the liquid crystal composition further comprises a reactive mesogen comprising at least one compound represented by Formula 2:

P1-SP1-MG-SP2-P2  Formula 2

wherein in Formula 2,

P1-* and *—P2 are each independently

—SP1-* is

and *—SP2-* is

wherein a and b are independently an integer of 0 to 2, each *-L-* is independently *—(CH 2 ) c —*, *—O(CH 2 ) c —*,

*—CH═CH—*, or *—C≡C—*, wherein c is an integer of 1 to 10, *—Z—* is *—(CH 2 ) d —*, wherein d is an integer of 0 to 12, and *—Ar—* is

wherein each A-* is independently H—*, a C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or *—CN); and

*-MG-* is

wherein each A-* is independently H—*, a C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or *—CN.

12. The method of claim 11 ,

wherein the liquid crystal aligning agent comprises at least one compound represented by Formulae SA 1-1 to SA 1-21:

13. The method of claim 10 , wherein the liquid crystal aligning agent comprises the compound represented by Formula 1, wherein X—* is

and

wherein the liquid crystal composition does not include a reactive mesogen comprising at least one compound represented by Formula 2:

P1-SP1-MG-SP2-P2  Formula 2

wherein in Formula 2,

P1-* and *—P2 are each independently

—SP1-* is

and *—SP2-* is

wherein a and b are independently an integer of 0 to 2, each *-L-* is independently *—(CH 2 ) c —*, *—O(CH 2 ) c —*,

*—CH═CH—*, or *—C≡C—*, wherein c is an integer of 1 to 10, *—Z—* is *—(CH 2 ) d —*, wherein d is an integer of 0 to 12, and *—Ar—* is

wherein each A-* is independently H—*, a C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or *—CN; and

*-MG-* is

wherein each A-* is independently H—*, a C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or *—CN.

14. The method of claim 13 ,

wherein the liquid crystal aligning agent comprises at least one compound represented by Formulae SA 2-1 to SA 2-17: