Alignment layer composition, liquid crystal display including the alignment layer composition, and manufacturing method of the liquid crystal display

Patent metadata

Field	Value
Publication number	US-9909066-B2
Application number	US-201615240402-A
Country	US
Kind code	B2
Filing date	Aug 18, 2016
Priority date	Apr 21, 2016
Publication date	Mar 6, 2018
Grant date	Mar 6, 2018

Abstract

An alignment layer composition including a copolymer of a dianhydride compound and a diamine compound, wherein the copolymer includes a repeating unit represented by Formula 1:

wherein each of Ar 1 and Ar 2 is independently a substituted or unsubstituted aromatic group comprising 6 to 30 carbon atoms, X is an electron donating group, and

is an ester group, wherein “*” indicates a point of attachment to the aromatic groups Ar 1 and Ar 2 .

First claim

What is claimed is:

1. An alignment layer composition comprising a copolymer of a dianhydride compound and a diamine compound, wherein the copolymer comprises a repeating unit represented by Formula 1:

wherein
each of Ar 1 and Ar 2 is independently a substituted or unsubstituted aromatic group comprising 6 to 30 carbon atoms,
X is a group selected from —C n H 2n+1 , —OC n H 2n+1 , —NH 2 , —NH(C n H 2n+1 ), —N(C n H 2n+1 ) 2 , —OH, —NH(COC n H 2n+1 ), —N(COC n H 2n+1 ) 2 , —OCOC n H 2n+1 , —CH 2 (C n H 2n+1 ), —CH(C n H 2n+1 ) 2 , —C(C n H 2n+1 ) 3 , —F, —Cl, and —Br, wherein n is a natural number from 1 to 10, and

is an ester group, wherein “*” indicates a point of attachment to the aromatic groups Ar 1 and Ar 2 .

2. The alignment layer composition of claim 1 , wherein each of Ar 1 and Ar 2 is independently a substituted or unsubstituted aromatic group comprising 6 carbon atoms.

3. The alignment layer composition of claim 2 , wherein the Formula 1 has a structure represented by Formula 1-1:

wherein X is a group selected from —C n H 2n+1 , —OC n H 2n+1 , —NH 2 , —NH(C n H 2n+1 ), —N(C n H 2n+1 ) 2 , —OH, —NH(COC n H 2n+1 ), —N(COC n H 2n+1 ) 2 , —OCOC n H 2n+1 , —CH 2 (C n H 2n+1 ), —CH(C n H 2n+1 ) 2 , —C(C n H 2n+1 ) 3 , —F, —Cl, and —Br, wherein n is a natural number from 1 to 10.

4. The alignment layer composition of claim 3 , wherein a C—O bond dissociation energy in the ester group of the repeating unit represented by the Formula 1-1 ranges from 2.563 electron volts to 3.019 electron volts.

5. The alignment layer composition of claim 3 , wherein the Formula 1-1 has a structure represented by one of Formulas 2 through 5:

6. The alignment layer composition of claim 1 , wherein the copolymer further comprises a repeating unit represented by Formula 6:

wherein Y is a divalent organic group derived from a diamine compound.

7. The alignment layer composition of claim 6 , wherein the copolymer comprises a repeating unit represented by Formula 7:

wherein
each of Ar 1 and Ar e is independently a substituted or unsubstituted aromatic group comprising 6 to 30 carbon atoms,
X is a group selected from —C n H 2n+1 , —OC n H 2n+1 , —NH 2 , —NH(C n H 2n+1 ), —N(C n H 2n+1 ) 2 , —OH, —NH(COC n H 2n+1 ), —N(COC n H 2n+1 ) 2 , —OCOC n H 2n+1 , —CH 2 (C n H 2n+1 ), —CH(C n H 2n+1 ) 2 , —C(C n H 2n+1 ) 3 , —F, —Cl, and —Br, wherein n is a natural number from 1 to 10, and
Y is a divalent organic group derived from a diamine compound.

8. The alignment layer composition of claim 7 , wherein the Formula 7 has a structure represented by Formula 7-1:

wherein
X is a group selected from —C n H 2n+1 , —OC n H 2n+1 , —NH 2 , —NH(C n H 2n+1 ), —N(C n H 2n+1 ) 2 , —OH, —NH(COC n H 2n+1 ), —N(COC n H 2n+1 ) 2 , —OCOC n H 2n+1 , —CH 2 (C n H 2n+1 ), —CH(C n H 2n+1 ) 2 , —C(C n H 2n+1 ) 3 , —F, —Cl, and —Br, wherein n is a natural number from 1 to 10, and
Y is a divalent organic group derived from a diamine compound.

9. The alignment layer composition of claim 1 , wherein the copolymer further comprises a repeating unit represented by Formula 8:

wherein
each of Ar 1 and Ar e is independently a substituted or unsubstituted aromatic group comprising 6 to 30 carbon atoms, and
X is a group selected from —C n H 2n+1 , —OC n H 2n+1 , —NH 2 , —NH(C n H 2n+1 ), —N(C n H 2n+1 ) 2 , —OH, —NH(COC n H 2n+1 ), —N(COC n H 2n+1 ) 2 , —OCOC n H 2n+1 , —CH 2 (C n H 2n+1 ), —CH(C n H 2n+1 ) 2 , —C(C n H 2n+1 ) 3 , —F, —Cl, and —Br, wherein n is a natural number from 1 to 10.

10. The alignment layer composition of claim 9 , wherein the Formula 8 has a structure represented by Formula 8-1:

wherein X is a group selected from —C n H 2n+1 , —OC n H 2n+1 , —NH 2 , —NH(C n H 2n+1 ), —N(C n H 2n+1 ) 2 , —OH, —NH(COC n H 2n+1 ), —N(COC n H 2n+1 ) 2 , —OCOC n H 2n+1 , —CH 2 (C n H 2n+1 ), —CH(C n H 2n+1 ) 2 , —C(C n H 2n+1 ) 3 , —F, —Cl, and —Br, wherein n is a natural number from 1 to 10.

11. The alignment layer composition of claim 1 , wherein the mole ratio of the dianhydride compound and the diamine compound is about 1:1.

12. A liquid crystal display, comprising:
first and second substrates facing each other;
a first alignment layer disposed on a surface of the first substrate that faces the second substrate;
a second alignment layer disposed on a surface of the second substrate that faces the first substrate; and
a liquid crystal layer interposed between the first substrate and the second substrate,
wherein at least one of the first alignment layer and the second alignment layer comprises a copolymer of a dianhydride compound and a diamine compound, and
wherein the copolymer comprises a repeating unit represented by Formula 1:

wherein
each of Ar 1 and Ar 2 is independently a substituted or unsubstituted aromatic group comprising 6 to 30 carbon atoms,
X is a group selected from —C n H 2n+1 , —OC n H 2n+1 , —NH 2 , —NH(C n H 2n+1 ), —N(C n H 2n+1 ) 2 , —OH, —NH(COC n H 2n+1 ), —N(COC n H 2n+1 ) 2 , —OCOC n H 2n+1 , —CH 2 (C n H 2n+1 ), —CH(C n H 2n+1 ) 2 , —C(C n H 2n+1 ) 3 , —F, —Cl, and —Br, wherein n is a natural number from 1 to 10, and

is an ester group, wherein “*” indicates a point of attachment to the aromatic groups Ar 1 and Ar 2 .

13. The liquid crystal display of claim 12 , wherein the copolymer further comprises a repeating unit represented by Formula 6:

wherein Y is a divalent organic group derived from a diamine compound.

14. The liquid crystal display of claim 12 , wherein the copolymer comprises a repeating unit represented by Formula 7:

wherein
each of Ar 1 and Ar 2 is independently a substituted or unsubstituted aromatic group comprising 6 to 30 carbon atoms,
X is a group selected from —C n H 2n+1 , —OC n H 2n+1 , —NH 2 , —NH(C n H 2n+1 ), —N(C n H 2n+1 ) 2 , —OH, —NH(COC n H 2n+1 ), —N(COC n H 2n+1 ) 2 , —OCOC n H 2n+1 , —CH 2 (C n H 2n+1 ), —CH(C n H 2n+1 ) 2 , —C(C n H 2n+1 ) 3 , —F, —Cl, and —Br, wherein n is a natural number from 1 to 10, and
Y is a divalent organic group derived from a diamine compound.

15. The liquid crystal display of claim 12 , wherein the copolymer further comprises a repeating unit represented by Formula 8:

Assignees

• Samsung Display Co Ltd
• Samsung Display Co Ltd

Inventors

• Kim Se Ran
• Kang Suk Hoon
• Kim Hoi Lim
• Cho Young Mi

Classifications

• C09K19/56 Primary

  Aligning agents · CPC title

• C08G73/16

  Polyester-imides · CPC title

• C08G73/1042

  Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds · CPC title

• G02F1/133788

  by light irradiation, e.g. linearly polarised light photo-polymerisation · CPC title

• C09D179/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title