IP Library Granted Patent US 10,119,074
Granted Patent B2
US 10,119,074 · App. 15/421,848 · Granted Nov 6, 2018

Liquid crystal composition and display device including the same

Inventors: Ji Eun Jang (Suwon-si, KR); Sun Young Kwon (Seoul, KR); Tae Hoon Kim (Suwon-si, KR); Jong Ho Son (Seoul, KR); Keun Chan Oh (Hwaseong-si, KR); Won Gap Yoon (Suwon-si, KR); Gak Seok Lee (Hwaseong-si, KR); Jin Hyeong Lee (Hwaseong-si, KR); Chang Hun Lee (Hwaseong-si, KR)
Assignee: SAMSUNG DISPLAY CO., LTD.
C09K19/3405C07D307/83G02F1/133723G02F1/134309C09K2019/3408G02F2202/023
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Quick Facts
Patent No.
US 10,119,074
App. No.
15/421,848
Granted
Nov 6, 2018
Kind
B2
Abstract

A liquid crystal composition includes a compound having a structure represented by formula A-1: wherein R A1 is an alkyl group, an alkoxy group, a cyano group, a halogen atom, or a hydrogen atom, R A2 is an alkyl group, a cyano group, a halogen atom, or a hydrogen atom, Z A is *—O—*, *—COO—*, *—OCO—*, *—CF 2 O—*, *—OCF 2 —*, *—CH 2 O—*, *—OCH 2 —*, *—SCH 2 —*, *—CH 2 S—*, *—C 2 F 4 —*, *—CH 2 CF 2 —*, *—CF 2 CH 2 —*, *—(CH 2 ) k —*, *—CH═CH—*, *—CF═CF—*, *—CH═CF—*, *—CF═CH—*, *—C≡C—*, *—CH═CHCH 2 O—*, or a single bond, X is a halogen atom, each of l1 and l2 is independently an integer of 0 to 2, and when l1 is 2 and Z A in a repeating unit defined by l1 are the same or different, wherein k is an integer of 1 to 5 and “*” indicates a point of attachment.

Claims (52)

1. A liquid crystal composition comprising a compound having a structure represented by formula A-1:

wherein

R A1 is an alkyl group, an alkoxy group, a cyano group, a halogen atom, or a hydrogen atom, R A2 is an alkyl group, a cyano group, a halogen atom, or a hydrogen atom, Z A is *—O—*, *—COO—*, *—OCO—*, *—CF 2 O—*, *—OCF 2 —*, *—CH 2 O—*, *—OCH 2 —*, *—SCH 2 —*, *—CH 2 S—*, *—C 2 F 4 —*, *—CH 2 CF 2 —*, *—CF 2 CH 2 —*, *—(CH 2 ) k —*, *—CH═CH—*, *—CF═CF—*, *—CH═CF—*, *—CF═CH—*, *—CH═CHCH 2 O—*, or a single bond, X is a halogen atom, each of l1 and l2 is independently an integer of 0 to 2, and when l1 is 2

and Z A in a repeating unit defined by l1 are the same or different, k is an integer of 1 to 5, and “*” indicates a point of attachment.

2. The liquid crystal composition of claim 1 , wherein the compound having the structure represented by formula A-1 is a compound having a structure represented by formula A-2:

wherein

R A1 is an alkyl group having a carbon number of 1 to 5, an alkoxy group having a carbon number of 1 to 5, a cyano group, a halogen atom, or a hydrogen atom, R A2 is an alkyl group having a carbon number of 1 to 5, a cyano group, a halogen atom, or a hydrogen atom, and Z A , X, l1, and l2 are the same as those in formula A-1.

3. The liquid crystal composition of claim 2 , wherein the compound having the structure represented by formula A-2 is a compound having a structure represented by formula A-3, formula A-4, or formula A-5:

wherein each of

is independently

each of Z A1 and Z A2 is independently *—O—*, *—COO—*, *—OCO—*, *—CF 2 O—*, *—OCF 2 —*, *—CH 2 O—*, *—OCH 2 —*, *—SCH 2 —*, *—CH 2 S—*, *—C 2 F 4 —*, *—CH 2 CF 2 —*, *—CF 2 CH 2 —*, *—(CH 2 ) k —*, *—CH═CH—*, *—CF═CF—*, *—CH═CF—*, *—CF═CH—*, *—C≡C—*, *—CH═CHCH 2 O—*, or a single bond, R A1 , R A2 , X, and l2 are the same as those in formula A-2, and k is an integer of 1 to 5.

4. The liquid crystal composition of claim 3 , wherein the compound having the structure represented by formula A-3, formula A-4, or formula A-5 is a compound having a structure represented by any one of formulas A-6 to A-13:

5. The liquid crystal composition of claim 4 , comprising one or more of the compounds having the structures represented by formulas A-6 to A-13.

6. The liquid crystal composition of claim 4 , wherein the compound having the structure represented by any one of formulas A-6 to A-13 has a refractive index anisotropy of about 0.230 to about 0.260 and a rotational viscosity at 20° C. of about 70 to about 100 millipascal-seconds.

7. The liquid crystal composition of claim 4 , wherein the liquid crystal composition has a refractive index anisotropy of about 0.080 to about 0.120, a dielectric anisotropy of about −5.5 to about −2.8, and a rotational viscosity at 20° C. of about 70 to about 110 millipascal-seconds.

8. The liquid crystal composition of claim 1 , further comprising a compound having a structure represented by formula B-1:

wherein each of

is independently

R B1 is an alkyl group, an alkoxy group, or a hydrogen atom, R B2 is an alkyl group, an alkoxy group, an acetamide group, a hydroxyl group, or a hydrogen atom, each of Z B1 , Z B2 , and Z B3 is independently alkylene group having a carbon number of 1 to 5, an alkenylene group having a carbon number of 2 to 3, *—O—*, *—COO—*, *—OCO—*, *—CF 2 O—*, *—OCF 2 —*, a single bond, or a double bond, and each of m1 and m2 is independently 0 or 1.

9. The liquid crystal composition of claim 8 , wherein the compound having the structure represented by formula B-1 is a compound having a structure represented by formula B-2:

wherein each of

is independently

R B1 is an alkyl group having a carbon number of 1 to 5, an alkoxy group having a carbon number of 1 to 5, or a hydrogen atom, R B2 is an alkyl group having a carbon number of 1 to 4, an alkoxy group having a carbon number of 1 to 4, an acetamide group, a hydroxyl group or a hydrogen atom, and Z B1 , Z B2 , Z B3 , m1, and m2 are the same as those in formula B-1.

10. The liquid crystal composition of claim 9 , wherein the compound having the structure represented by formula B-2 is a compound having a structure represented by formula B-3, formula B-4, or formula B-5:

wherein

R B1 , R B2 , Z B1 , Z B2 , and Z B3 are the same as those in formula B-2.

11. The liquid crystal composition of claim 10 , wherein the compound having the structure represented by formula B-3, formula B-4, or formula B-5 is a compound having a structure represented by any one of formulas B-6 to B-9:

12. The liquid crystal composition of claim 8 , further comprising a compound having a structure represented by formula C-1:

wherein each of R C1 and R C2 is independently

Z C is an alkylene group, an alkyleneoxy group, an ether group, or a single bond, X is a halogen atom, n1 is an integer of 2 to 4, each of n2 and n3 is independently 0 or 1, and each of n4 to n6 is independently an integer of 0 to 2.

13. The liquid crystal composition of claim 12 , wherein the compound having the structure represented by formula C-1 is a compound having a structure represented by formula C-2:

wherein R C1 , R C2 , Z C , X, and n1 to n6 are the same as those in formula C-1.

14. The liquid crystal composition of claim 13 , wherein the compound having the structure represented by formula C-2 is a compound having a structure represented by formula C-3 or formula C-4:

wherein R C1 , R C2 , Z C , X, n1, n4, and n6 are the same as those in formula C-1.

15. The liquid crystal composition of claim 14 , wherein the compound having the structure represented by formula C-3 or formula C-4 is a compound having a structure represented by any one of formulas C-5 to C-8:

16. A display device comprising:

an insulating substrate; and

a liquid crystal layer disposed on the insulating substrate and comprising a compound having a structure represented by formula A-1:

wherein

R A1 is an alkyl group, an alkoxy group, a cyano group, a halogen atom, or a hydrogen atom, R A2 is an alkyl group, a cyano group, a halogen atom or a hydrogen atom, Z A is *—O—*, *—COO—*, *—OCO—*, *—CF 2 O—*, *—OCF 2 —*, *—CH 2 O—*, *—OCH 2 —*, *—SCH 2 —*, *—CH 2 S—*, *—C 2 F 4 —*, *—CH 2 CF 2 —*, *—CF 2 CH 2 —*, *—(CH 2 ) k —*, *—CH═CH—*, *—CF═CF—*, *—CH═CF—*, *—CF═CH—*, *—C≡C—*, *—CH═CHCH 2 O—*, or a single bond, X is a halogen atom, l1 is an integer of 0 to 2, l2 is an integer of 0 to 3, and when l1 is 2

and Z A in a repeating unit defined by l1 are the same or different, k is an integer of 1 to 5, and “*” indicates a point of attachment.

17. The display device of claim 16 , wherein the liquid crystal layer further comprises a compound having a structure represented by formula B-1:

wherein each of

is independently

R B1 is an alkyl group, an alkoxy group, or a hydrogen atom, R B2 is an alkyl group, an alkoxy group, an acetamide group, a hydroxyl group, or a hydrogen atom, each of Z B1 , Z B2 and Z B3 is independently an alkylene group having a carbon number of 1 to 5, an alkenylene group having a carbon number of 2 to 3, *—O—*, *—COO—*, *—OCO—*, *—CF 2 O—*, *—OCF 2 —*, a single bond, or a double bond, and each of m1 and m2 is independently 0 or 1.

18. The display device of claim 17 , further comprising an alignment layer disposed between the insulating substrate and the liquid crystal layer, wherein the alignment layer comprises a main alignment layer, which comprises a main chain having an imide group as a repeating unit, and an alignment stabilization layer comprising a crosslinked polymer comprising a compound having a structure represented by formula C-1:

wherein each of R C1 and R C2 is independently

Z C is an alkylene group, an alkyleneoxy group, an ether group or a single bond, X is a halogen atom, n1 is an integer of 2 to 4, each of n2 and n3 is independently 0 or 1, and each of n4 to n6 is independently an integer of 0 to 2.

19. The display device of claim 18 , wherein the liquid crystal layer further comprises the compound having the structure represented by formula C-1, wherein the compound having the structure represented by formula C-1 is present in an amount of about 100 ppm or less based on a total weight of the liquid crystal layer.

20. The display device of claim 19 , further comprising:

a first electrode disposed between the insulating substrate and the alignment layer; and

a second electrode facing the first electrode, and the liquid crystal layer disposed between the first electrode and the second electrode.

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 Feb 6, 2017
From: JANG, JI EUN; KWON, SUN YOUNG; KIM, TAE HOON; SON, JONG HO; OH, KEUN CHAN; YOON, WON GAP; LEE, GAK SEOK; LEE, JIN HYEONG; LEE, CHANG HUN
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 041630/0579 →
Priority Claims (1)
KR 10-2016-0123995 · Sep 27, 2016 · national
Continuity (1)
Related Publication 20180086981A1 · Mar 29, 2018