IP Library › Granted Patent US 10,041,001

Granted Patent B2

US 10,041,001 · App. 15/204,290 · Granted Aug 7, 2018

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

Inventors: Ho Lim (Suwon-si, KR); Hyun Ku Ahn (Hwaseong-si, KR); Jae Jin Lyu (Yongin-si, KR)

Assignee: SAMSUNG DISPLAY CO., LTD.

C09K19/56 C09K19/32 C09K19/348 C09K19/3444 C09K19/3475 C09K19/404 C09K2019/0448

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Quick Facts

Patent No.: US 10,041,001
App. No.: 15/204,290
Granted: Aug 7, 2018
Kind: B2

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Abstract

A liquid crystal composition including: a liquid crystal compound and a liquid crystal aligning agent containing at least one compound represented by Formula 1: wherein in the Formula 1, X—*, *-L 1 -*, *-L 2 -*, *-L 3 -*, *—C—*, *—R—*, Y—*, n 1 , n 2 , and m is the same as defined in the specification.

Claims (215)

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 C 1-20 -alkyl-*,

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

*—CH═CH—*, *—C≡C—* (wherein p1 is an integer of 1 to 10), or a combination thereof;

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

*—CH═CH—*, *—C≡C—* (wherein p2 is an integer of 1 to 10), or a combination thereof;

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

*—CH═CH—*, *—C≡C—* (wherein p3 is an integer of 1 to 10), or a combination thereof;

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

*—C—* is a substituted or unsubstituted cyclic linking group selected from substituted or unsubstituted

substituted or unsubstituted

and substituted or unsubstituted

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

2. The liquid crystal composition of claim 1 ,

wherein X—* is 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

(wherein a is an integer of 0 to 2) and *—SP2-* is

(wherein b is an integer of 0 to 2), wherein 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 H—*, C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or CN—*); and

*-MG-* is

(wherein each A-* is H—*, 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 1-8:

4. The liquid crystal composition of claim 1 ,

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

wherein X—* is

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

(wherein a is an integer of 0 to 2) and *—SP2-* is

(wherein b is an integer of 0 to 2), in each of which *-L-* is *—(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 H—*, C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or CN—*); and

*-MG-* is

(wherein each A-* is H—*, 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 2-14:

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 mesogens comprising two or more compounds represented by Formula 2, wherein the polymer of reactive mesogens 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 C 1-20 -alkyl-*;

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

*—CH═CH—*, *—C≡C—* (wherein p1 is an integer of 1 to 10), or a combination thereof;

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

*—CH═CH—*, *—C≡C—* (wherein p2 is an integer of 1 to 10), or a combination thereof;

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

*—CH═CH—*, *—C≡C—* (wherein p3 is an integer of 1 to 10), or a combination thereof;

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

*—C—* is a substituted or unsubstituted cyclic linking group selected from substituted or unsubstituted

substituted or unsubstituted

and substituted or unsubstituted

wherein at least one hydrogen in the substituted cyclic linking group is substituted with C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or (meth)acryloxy-C 1-10 -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 610 arylene is substituted with C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or (meth)acryloxy-C 1-10 -alkyl-*;

Y—* is

(wherein n is an integer of 0 to

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

(wherein a is an integer of 0 to 2) and *—SP2-* is

(wherein b is an integer of 0 to 2), in each of which *-L-* is *—(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 H—*, C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or CN—*); and

*-MG-* is

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

7. The liquid crystal display device of claim 6 ,

wherein the liquid crystal aligning agent comprises at least compound represented by Formulae SA 1-1 to SA 1-8:

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

wherein the liquid crystal device does not include compounds represented by Formula 2:

wherein in Formula 1-1,

X″—* is a polymerizing group selected from

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

*—CH═CH—*, *—C≡C—* (wherein p1 is an integer of 1 to 10), or a combination thereof;

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

*—CH═CH—*, *—C≡C—* (wherein p2 is an integer of 1 to 10), or a combination thereof;

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

*—CH═CH—*, *—C≡C—* (wherein p3 is an integer of 1 to 10), or a combination thereof;

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

*—C—* is a substituted or unsubstituted cyclic linking group selected from substituted or unsubstituted

substituted or unsubstituted

and substituted or unsubstituted

wherein at least one hydrogen in the substituted cyclic linking group is substituted with C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or (meth)acryloxy-C 1-10 -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 610 arylene is substituted with C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or (meth)acryloxy-C 1-10 -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

(wherein a is an integer of 0 to 2) and *—SP2-* is

(wherein b is an integer of 0 to 2), in each of which *-L-* is *—(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 H—*, C 1-10 -alkyl-*, F—*, Br—*, I—*, *—I—*, *—OH, *—NH 2 , or CN—*); and

*-MG-* is

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

9. The liquid crystal display device of claim 8 ,

wherein the liquid crystal aligning agent comprises at least compound represented by Formulae SA 2-1 to SA 2-14:

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 rays when a voltage is applied to the liquid crystal cell.

11. The method of claim 10 ,

wherein X—* is 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

(wherein a is an integer of 0 to 2) and *—SP2-* is

(wherein b is an integer of 0 to 2), in each of which *-L-* is *—(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 H—*, C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or CN—*); and

*-MG-* is

(wherein each A-* is H—*, 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 compound represented by Formulae SA 1-1 to SA 1-8:

13. The method of claim 10 ,

wherein at least one of 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

(wherein a is an integer of 0 to 2) and *—SP2-* is

(wherein b is an integer of 0 to 2), in each of which *-L-* is *—(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 H—*, C 1-10 -alkyl-*, F—*, Br—*, I—*, *—OH, *—NH 2 , or CN—*); and

-MG-* is

(wherein each A-* is H—*, C 1-10 -alkyl-*, F—*, Br—*, *—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 2-14:

Assignments (3)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 4, 2026

From: TCL CHINA STAR OPTOELECTRONICS TECHNOLOGY CO., LTD.

To: LONESTAR CRYSTAL DISPLAY LLC

Reel/Frame 074944/0730 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 21, 2022

From: SAMSUNG DISPLAY CO., LTD.

To: TCL CHINA STAR OPTOELECTRONICS TECHNOLOGY CO., LTD.

Reel/Frame 060778/0543 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 21, 2016

From: LIM, HO; AHN, HYUN KU; LYU, JAE JIN

To: SAMSUNG DISPLAY CO., LTD.

Reel/Frame 039208/0984 →

Priority Claims (1)

KR 10-2016-0007512 · Jan 21, 2016 · national

Continuity (1)

Related Publication 20170210993A1 · Jul 27, 2017