IP Library Granted Patent US 11,851,599
Granted Patent B2
US 11,851,599 · App. 17/319,229 · Granted Dec 26, 2023

Liquid crystal composition and liquid crystal display device thereof

Inventors: Di He (Yangzhong, CN); Wenquan Ding (Yangzhong, CN); Haibin Xu (Yangzhong, CN); Shuang Xu (Yangzhong, CN); Lifang Yao (Yangzhong, CN)
Assignee: Jiangsu Hecheng Display Technology Co., Ltd.
C09K19/12C09K2019/123C09K2019/124
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Quick Facts
Patent No.
US 11,851,599
App. No.
17/319,229
Granted
Dec 26, 2023
Kind
B2
Abstract

A liquid crystal composition and a liquid crystal display device including the liquid crystal composition include at least one compound of general formula I and at least one compound of general formula II. Compared with the prior art, the liquid crystal composition has a smaller voltage change rate at high and low temperatures and a shorter low temperature response time, while maintaining an appropriate optical anisotropy, an appropriate clearing point, an appropriate absolute value of dielectric anisotropy, such that the liquid crystal display device having the liquid crystal composition has a better display and a faster response speed.

Claims (129)

1. A liquid crystal composition, wherein the liquid crystal composition comprises:

at least one compound of general formula I

at least one compound of general formulas II-1, II-2, II-5, II-6, II-7, and II-11 selected from the group consisting of:

at least one compound of general formula III-1

in which,

R 1 represents —H;

R 2 represents —H, halogen, C 1-12 linear alkyl or C 3-12 branched alkyl,

wherein one or more nonadjacent —CH 2 — in the C 1-12 linear alkyl or C 3-12 branched alkyl can each be independently replaced by —CH═CH—, —C≡C—, —O—, —CO—, —CO—O— or —O—CO—, and one or more —H in

can each be independently substituted by —F or —Cl;

R 3 and R 4 each independently represents C 1-12 linear alkyl or C 3-12 branched alkyl,

wherein one or more nonadjacent —CH 2 — in the C 1-12 linear alkyl or C 3-12 branched alkyl can each be independently replaced by —CH═CH—, —C≡C—, —O—, —CO—, —CO—O— or —O—CO—;

ring

represents

wherein one or more —CH 2 — in

can be replaced by —O—, and one or more single bond in the rings can be replaced by double bond, wherein one or more —H on

in the ring

can each be independently substituted by —F, —Cl, —CN, —CH 3 or —OCH 3 , and one or more —CH═ in the ring

can be replaced by —N═;

ring

represents

wherein one or more —CH 2 — in and

can be replaced by —O—, and one or more single bond in the rings can be replaced by double bond, wherein one or more —H on

in the ring

can each be independently substituted by —F, —Cl, —CN, —CH 3 or —OCH 3 , and one or more —CH═ in the ring

can be replaced by —N═;

X 1 represents —O—, —S—, —CO—, —CF 2 —, —NH— or —NF—;

Y 1 and Y 2 each independently represents —H, halogen, C 1-3 halogenated or unhalogenated alkyl, or C 1-3 halogenated or unhalogenated alkoxy;

Z 1 represents —O—, —S—, —CO—O—, —O—CO—, —OCH 2 —, —CH═CH—, —C≡C—, —CH 2 CH 2 —, —CF 2 CF 2 —, —(CH 2 ) 4 —, —CF 2 O— or —OCF 2 —, and Z 2 represents single bond, —O—, —S—, —CO—O—, —O—CO—, —CH 2 O—, —OCH 2 —, —CH═CH—, —C≡C—, —CH 2 CH 2 —, —CF 2 CF 2 —, —(CH 2 ) 4 —, —CF 2 O— or —OCF 2 —;

T 1 , T 2 , T 4 , T 5 , T 6 , and T 8 each independently represents —H, —F, —Cl, —CN, —CH 3 or —OCH 3 ;

R 5 and R 6 each independently represents C 1-10 linear alkyl or C 3-10 branched alkyl,

C 1-9 linear alkyl or C 3-9 branched alkoxy, or C 2-10 linear alkyl or C 3-10 branched alkenyl; and

n 1 represents 1 or 2, n 2 represents 0, 1 or 2, wherein when n 1 =2, ring

can be same or different, and Z 1 can be same or different; wherein when n 2 =2, ring

can be same or different, and Z 2 can be same or different.

2. The liquid crystal composition according to claim 1 , wherein the compound of general formula I is selected from a group consisting of the following compounds:

in which,

ring

represents

wherein one or more —CH 2 — in

can be replaced by —O—, and one or more single bond in the rings can be replaced by double bond, wherein one or more —H on

in the ring

can each be independently substituted by —F, —Cl, —CN, —CH 3 or —OCH 3 , and one or more —CH═ in the ring

can be replaced by —N═;

Z 1 ′ represents —O—, —S—, —CO—O—, —O—CO—, —OCH 2 —, —CH═CH—, —C≡C—, —CH 2 CH 2 —, —CF 2 CF 2 —, —(CH 2 ) 4 —, —CF 2 O— or —OCF 2 —; and

X 1 represents —O—, —S— or —CO—.

3. The liquid crystal composition according to claim 1 , further comprising a compound selected from a group consisting

wherein R 3 and R 4 each independently represents C 1-12 linear alkyl or C 3-12 branched alkyl,

wherein one or more nonadjacent —CH 2 — in the C 1-12 linear alkyl or C 3-12 branched alkyl can each be independently replaced by —CH═CH—, —C≡C—, —O—, —CO—, —CO—O— or —O—CO—.

4. The liquid crystal composition according to claim 1 , wherein the compound of general formula I provides 0.1-40 wt. % of the total weight of the liquid crystal composition; and the compound of general formulas II-1, II-2, II-5, II-6, II-7, and II-11 provides 0.1-70 wt. % of the total weight of the liquid crystal composition.

5. The liquid crystal composition according to claim 1 ,

wherein the liquid crystal composition further comprises at least one compound of general formula III-2:

in which,

T 9 , T 10 and T 11 each independently represents —H, —F, —Cl, —CN, —CH 3 or —OCH 3 ; and

X 2 represents —F, —CF 3 , —OCF 3 or —CH 2 CH 2 CH═CF 2 .

6. The liquid crystal composition according to claim 5 , wherein the compounds of general formulas III-1 and III-2 provide 0.1-50 wt. % of the total weight of the liquid crystal composition.

7. The liquid crystal composition according to claim 1 , wherein the liquid crystal composition further comprises at least one compound of general formula M:

in which,

R M1 and R M2 each independently represents C 1-12 linear alkyl or C 3-12 branched alkyl,

wherein one or more nonadjacent —CH 2 — in the C 1-12 linear alkyl or C 3-12 branched alkyl can each be independently replaced by —CH═CH—, —C≡C—, —O—, —CO—, —CO—O— or —O—CO—;

ring

ring

and ring

each independently represents

wherein one or more —CH 2 — on

in the rings

can be replaced by —O—, one or more single bond in the ring can be replaced by double bond, wherein at most one —H on

in the rings

can be substituted by halogen;

Z M1 and Z M2 each independently represents single bond, —CO—O—, —O—CO—, —CH 2 O—, —OCH 2 —, —C≡C—, —CH═CH—, —CH 2 CH 2 — or —(CH 2 ) 4 —; and

n M represents 0, 1 or 2, wherein when n M =2, ring

can be same or different, Z M2 can be same or different; and

when n M =1 or 2, at least one of ring

ring

and ring

is non-aromatic ring.

8. The liquid crystal composition according to claim 1 , wherein the liquid crystal composition further comprises at least one compound of general formula N:

in which,

R N1 and R N2 each independently represents C 1-12 linear alkyl or C 3-12 branched alkyl,

wherein one or more nonadjacent —CH 2 — in the C 1-12 linear alkyl or C 3-12 branched alkyl can each be independently replaced by —CH═CH—, —C≡C—, —O—, —CO—, —CO—O— or —O—CO—;

ring

and ring

each independently represents or

wherein one or more —CH 2 — on

in the rings

and

can be replaced by —O—, and one or more single bond in the ring can be replaced by double bond, wherein one or more —H on

in the rings

can each be independently substituted by —F, —Cl, —CN, —CH 3 or —OCH 3 , and one or more —CH═ in the ring can be replaced by —N═;

Z N1 and Z N2 each independently represents single bond, —CO—O—, —O—CO—, —CH 2 O—, —OCH 2 —, —CH═CH—, —C≡C—, —CH 2 CH 2 —, —CF 2 CF 2 —, —(CH 2 ) 4 —, —CF 2 O— or —OCF 2 —;

L N1 and L N2 each independently represents —H, C 1-3 alkyl or halogen;

n N1 represents 0, 1, 2 or 3, n N2 represents 0 or 1, and 0≤n N1 +n N2 ≤3, wherein when n N1 =2 N 1 or 3, ring

can be same or different, Z N1 can be same or different;

when 0≤n N1 +n N2 ≤2, compounds of general formula N do not comprise terphenyl structure; and

when n N1 +n N2 =3, compounds of general formula N do not comprise quaterphenyl structure.

9. A liquid crystal display device comprising the liquid crystal composition of claim 1 .

10. A liquid crystal composition, wherein the liquid crystal composition comprises:

at least one compound of general formula I

at least one compound of general formulas II-1, II-2, II-5, II-6, II-7, and II-11 selected from the group consisting of:

at least one compound of general formula III-1

in which,

R 1 represents —H;

R 2 represents —H, halogen, C 1-12 linear alkyl or C 3-12 branched alkyl,

wherein one or more nonadjacent —CH 2 — in the C 1-12 linear alkyl or C 3-12 branched alkyl can each be independently replaced by —CH═CH—, —C≡C—, —O—, —CO—, —CO—O— or —O—CO—, and one or more —H in

can each be independently substituted by —F or —Cl;

R 3 and R 4 each independently represents C 1-12 linear alkyl or C 3-12 branched alkyl,

wherein one or more nonadjacent —CH 2 — in the C 1-12 linear alkyl or C 3-12 branched alkyl can each be independently replaced by —CH═CH—, —C≡C—, —O—, —CO—, —CO—O— or —O—CO—;

ring

represents

wherein one or more —CH 2 — in

can be replaced by —O—, and one or more single bond in the rings can be replaced by double bond, wherein one or more —H on

in the ring

can each be independently substituted by —F, —Cl, —CN, —CH 3 or —OCH 3 , and one or more —CH═ in the ring

can be replaced by —N═;

ring

represent

wherein one or more —CH 2 — in

can be replaced by —O—, and one or more single bond in the rings can be replaced by double bond, wherein one or more —H on

in the ring

can each be independently substituted by —F, —Cl, —CN, —CH 3 or —OCH 3 , and one or more —CH═ in the ring

can be replaced by —N═;

X 1 represents —O—, —S—, —CO—, —CF 2 —, —NH— or —NF—;

Y 1 and Y 2 each independently represents —H, halogen, C 1-3 halogenated or unhalogenated alkyl, or C 1-3 halogenated or unhalogenated alkoxy;

Z 1 and Z 2 each independently represents single bond, —O—, —S—, —CO—O—, —O—CO—, —CH 2 O—, —OCH 2 —, —CH═CH—, —C≡C—, —CH 2 CH 2 —, —CF 2 CF 2 —, —(CH 2 ) 4 —, —CF 2 O— or —OCF 2 —;

T 1 , T 2 , T 4 , T 5 , T 6 , and T 8 each independently represents —H, —F, —Cl, —CN, —CH 3 or —OCH 3 ;

R 5 and R 6 each independently represents C 1-10 linear alkyl or C 3-10 branched alkyl,

C 1-9 linear alkyl or C 3-9 branched alkoxy, or C 2-10 linear alkyl or C 3-10 branched alkenyl; and

n 1 represents 1 or 2, n 2 represents 1 or 2, wherein when n 1 =2, ring

can be same or different, and Z 1 can be same or different; wherein when n 2 =2, ring

can be same or different, and Z 2 can be same or different.

Assignments (2)
DECLARATION ON CHANGE OF ADDRESS Recorded Nov 8, 2022
From: JIANGSU HECHENG DISPLAY TECHNOLOGY CO., LTD.
To: JIANGSU HECHENG DISPLAY TECHNOLOGY CO., LTD.
Reel/Frame 061896/0854 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 13, 2021
From: HE, DI; DING, WENQUAN; XU, HAIBIN; XU, SHUANG; YAO, LIFANG
To: JIANGSU HECHENG DISPLAY TECHNOLOGY CO., LTD.
Reel/Frame 056228/0681 →
Priority Claims (1)
CN 202010413412.3 · May 15, 2020 · national
Continuity (1)
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