Reactive mesogen and liquid crystal composition including the same

Patent metadata

Field	Value
Publication number	US-11066602-B2
Application number	US-201916420110-A
Country	US
Kind code	B2
Filing date	May 22, 2019
Priority date	Jul 22, 2016
Publication date	Jul 20, 2021
Grant date	Jul 20, 2021

Abstract

Provided are a reactive mesogen that may improve display quality of a liquid crystal display, and a liquid crystal composition including the same. The reactive mesogen is represented by the following Formula:BZ1b1XZ2b2Pawhere X, Z1, Z2, B, and Pa are specified in the disclosure, and each of b1 and b2 is independently an integer between 0 to 6, inclusive.

First claim

What is claimed is:

1. A reactive mesogen represented by the following Formula 2:
B Z 1 b1 X Z 2 b2 Pa
where X is one of the following X-1 to X-17,

each of Z 1 and Z 2 is independently a direct linkage, —O—, —S—, —CO—, —COO—, —OCOO—, —O(CH 2 ) m1 —, —S(CH 2 ) m1 —, —O(CF 2 ) m1 —, —S(CF 2 ) m1 —, —(CH 2 ) m1 —, —CF 2 CH 2 —, —(CF 2 ) m1 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, —(CH 2 ) m1 —COO—, —(CH 2 ) m1 —COO—(CH 2 ) m2 —O—, —CH—(S p —Pa)—, —CH 2 CH—(S p —Pa)—, or —(CH—(S p —Pa)—CH—(S p —Pa))—,
each of m1 and m2 is independently an integer of 0 to 4,
S p is a direct linkage, or a spacer group,
Each of b1 and b2 is independently an integer of 0 to 6,
Pa is a polymerizable group,
B is an unsubstituted heterocycle, a substituted or unsubstituted crown ether group, or

n1 and n2 are each independently an integer of 1 to 12, T 1 and T 2 are each independently —OH, —CH 3 , —CF 3 , —CHF 2 , —CH 2 F, —CH 2 Br, —CHBr 2 , —CHCl 2 , or —CH 2 Cl,
at least one of T 1 and T 2 is —OH, and
each * is a connection to X, Z 1 , Z 2 , B, or Pa.

2. The reactive mesogen of claim 1 , wherein B is one of the following B-1 to B-20 and E-1 to E-13:

and
wherein each * is a connection to X or Z 1 .

3. The reactive mesogen of claim 1 , wherein Pa is one of the following P-1 to P-9:

and
wherein each * is a connection to X or Z 2 .

4. A liquid crystal composition, comprising:
a liquid crystal compound; and
a first reactive mesogen represented by the following Formula 3:

where A 1 , A 2 , and A 3 are each independently a substituted or unsubstituted divalent hydrocarbon ring, or a substituted or unsubstituted divalent heterocycle,
a1, b1, and b2 are each independently an integer of 0 to 6,
a2 and a3 are each independently 0 or 1,
L 1 and L 2 are each independently a direct linkage, —O—, —S—, —CO—, —COO—, —OCOO—, —O(CH 2 ) k1 —, —S(CH 2 ) k1 —, —O(CF 2 ) k1 —, —S(CF 2 ) k1 —, —(CH 2 ) k1 —, —CF 2 CH 2 —, —(CF 2 ) k1 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, or —(CH 2 ) k1 —COO—(CH 2 ) k2 —O—,
k1 and k2 are each independently an integer of 0 to 4,
Z 1 and Z 2 are each independently a direct linkage, —O—, —S—, —CO—, —COO—, —OCOO—, —O(CH 2 ) m1 —, —S(CH 2 ) m1 —, —O(CF 2 ) m1 —, —S(CF 2 ) m1 —, —(CH 2 ) m1 —, —CF 2 CH 2 —, —(CF 2 ) m1 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, —(CH 2 ) m1 —COO—, —(CH 2 ) m1 —COO—(CH 2 ) m2 —O—, —CH—(S p —Pa)—, —CH 2 CH—(S p —Pa)—, or —(CH—(S p —Pa)—CH—(S p —Pa))—,
m1 and m2 are each independently an integer of 0 to 4,
S p is a direct linkage, or a spacer group,
Pa is a polymerizable group,
B is an unsubstituted heterocycle, a substituted or unsubstituted crown ether group, or

n1 and n2 are each independently an integer of 1 to 12, T 1 and T 2 are each independently —OH, —CH 3 , —CF 3 , —CHF 2 , —CH 2 F, —CH 2 Br, —CHBr 2 , —CHCl 2 , or —CH 2 Cl, and
at least one of T 1 and T 2 is —OH, and
each * is a connection to Z 1 or A 1 .

5. The liquid crystal composition of claim 4 , wherein B is one of the following B-1 to B-20 and E-1 to E-13:

and
wherein each * is a connection to Z 1 or A 1 .

6. The liquid crystal composition of claim 4 , further comprising a second reactive mesogen represented by the following Formula 4:

where Pa and Pb are each independently one of the following polymerizable groups P-1 to P-10, wherein a group where Pa and Pb are P-10 at the same time is excluded, and p is an integer of 1 to 20, and
each of A 1 , A 2 , A 3 , L 1 , L 2 , Z 1 , Z 2 , a1, a2, a3, b1, and b2 are the same as defined in claim 4 :

and
wherein each * is a connection to X or Z 1 , Z 2 , A 1 or A 3 .

7. The liquid crystal composition of claim 6 , further comprising a third reactive mesogen represented by the following Formula 5:
B Z 1 b1 X Z 2 b2 Pa   [Formula 5]

where X is one of the following X-1 to X-17,

and
Z 1 , Z 2 , B, and Pa are the same as defined in claim 4 ,
and wherein each * is a connection to X or Z 1 , Z 2 , B or Pa.

8. The liquid crystal composition of claim 4 , wherein the first reactive mesogen is comprised in an amount 0.1 to 2 parts by weight on the basis of 100 parts by weight of the liquid crystal compound.

9. The liquid crystal composition of claim 7 , wherein the third reactive mesogen is comprised in an amount 1 to 10 parts by weight on the basis of 100 parts by weight of a sum of the first reactive mesogen and the second reactive mesogen.

10. The liquid crystal composition of claim 4 , wherein the liquid crystal compound comprises a nematic liquid crystal compound.

11. The liquid crystal composition of claim 4 , wherein the liquid crystal compound comprises at least one of the following L-1 to L-10:

Assignees

• Samsung Display Co Ltd

Inventors

• Lim Ho

Classifications

• C09K19/3405 Primary

  the heterocyclic ring being a five-membered ring · CPC title

• C07D273/00

  Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 · CPC title

• C09K2019/0448

  the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate · CPC title

• C09K19/34

  containing at least one heterocyclic ring · CPC title

• C09K2019/122

  Ph-Ph · CPC title