Vertical alignment layer comprising cyclic olefin copolymer

Patent metadata

Field	Value
Publication number	US-10131843-B2
Application number	US-201515519982-A
Country	US
Kind code	B2
Filing date	Dec 17, 2015
Priority date	Dec 18, 2014
Publication date	Nov 20, 2018
Grant date	Nov 20, 2018

Abstract

The present invention relates to a vertical alignment layer including a cyclic olefin copolymer, and more specifically, the present invention relates to a vertical alignment layer capable of having alignment even in a low temperature process, and exhibiting excellent liquid crystal vertical alignment by including a cyclic olefin copolymer having a specific substituent.

First claim

What is claimed is:

1. A vertical alignment layer comprising:
a cyclic olefin copolymer of a monomer represented by Chemical Formula 1 below:

in Chemical Formula 1,
q is an integer of 0 to 4,
at least one of R1 to R4 is a radical represented by Chemical Formula 1a below,
remaining R1 to R4 except for the radical represented by Chemical Formula 1a below are the same as each other or different from each other, and are each independently selected from the group consisting of hydrogen; halogen; substituted or unsubstituted C1-C20 linear or branched alkyl; substituted or unsubstituted C2-C20 linear or branched alkenyl; substituted or unsubstituted C2-C20 linear or branched alkynyl; substituted or unsubstituted C3-C12 cycloalkyl; substituted or unsubstituted C6-C40 aryl; substituted or unsubstituted C5-C12 arylalkyl; and a polar functional group including at least one selected from oxygen, nitrogen, phosphorus, sulfur, silicon, and boron, and
when R1 to R4 are not hydrogen; halogen; or the polar functional group, at least one combination of R1 and R2 or R3 and R4 may be linked to each other to form a C1-C10 alkylidene group, or R1 or R2 may be linked to any one of R3 and R4 to form a C4-C12 saturated or unsaturated aliphatic ring, or a C6-C24 aromatic ring,

in Chemical Formula 1a,
A and C are each independently a simple bond, or substituted or unsubstituted C1-C5 alkylene,
B is ester,
n1 and n2 are each independently an integer of 0 to 5, and n1+n2 are an integer of 1 to 5, and
X 1 and X 2 are substituents substituted in a benzene ring, and each independently a fluorine atom (F), C1-C5 fluorinated alkyl, C1-C5 fluorinated alkoxy, C6-C20 fluorinated aryl, or C6-C20 fluorinated alkoxyaryl.

2. The vertical alignment layer of claim 1 , wherein:
the polar functional group including at least one selected from oxygen, nitrogen, phosphorus, sulfur, silicon, and boron is selected from the group consisting of functional groups to be listed below:
—OR 6 , —OC(O)OR 6 , —R 5 OC(O)OR 6 , —C(O)OR 6 , —R 5 C(O)R 6 , —C(O)R 6 , —R 5 C(O)R 6 —, —OC(O)R 6 , —(R 5 O)R 6 , —(R 5 O) p —OR 6 , —OR 5p —OR 6 , —C(O)—O—C(O)R 6 , —R 5 C(O)—O—C(O)R 6 , —SR 6 , —R 5 SR 6 , —SSR 6 , —R 5 SSR 6 , —S(═O)R 6 , —R 5 S(═O)R 6 , —R 5 C(═S)R 6 —, —R 5 C(═S)SR 6 , —R 5 SO 3 R 6 , —SO 3 R 6 , —R 5 N═C═S, —N═C═S, —NCO, —R 5 —NCO, —CN, —R 5 CN, —NNC(═S)R 6 , —R 5 NNC(═S)R 6 , —NO 2 , —R 5 NO 2 ,

in the polar functional group, p is each independently an integer of 1 to 10,
R 5 is substituted or unsubstituted C1-C20 linear or branched alkylene; substituted or unsubstituted C2-C20 linear or branched alkenylene; substituted or unsubstituted C2-C20 linear or branched alkynylene; substituted or unsubstituted C3-C12 cycloalkylene; substituted or unsubstituted C6-C40 arylene; substituted or unsubstituted C1-C20 carbonyloxylene; or substituted or unsubstituted C1-C20 alkoxylene, and
R 6 , R 7 and R 8 are each independently selected from the group consisting of hydrogen; halogen; substituted or unsubstituted C1-C20 linear or branched alkyl; substituted or unsubstituted C2-C20 linear or branched alkenyl; substituted or unsubstituted C2-C20 linear or branched alkynyl; substituted or unsubstituted C3-C12 cycloalkyl; substituted or unsubstituted C6-C40 aryl; substituted or unsubstituted C1-C20 alkoxy; and substituted or unsubstituted C1-C20 carbonyloxy.

3. The vertical alignment layer of claim 2 , wherein:
each functional group of R 5 to R 8 is unsubstituted or substituted with a functional group selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, arylalkyl, haloarylalkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl and siloxy.

4. The vertical alignment layer of claim 1 , wherein:
the copolymer is an alignment copolymer including a repeating unit represented by Chemical Formula 2a or 2b below:

in Chemical Formulas 2a and 2b, each independently,
m is 50 to 5000,
q is an integer of 0 to 4,
at least one of R1 to R4 is a radical represented by Chemical Formula 1a below,
remaining R1 to R4 except for the radical represented by Chemical Formula 1a below are the same as each other or different from each other, and are each independently selected from the group consisting of hydrogen; halogen; substituted or unsubstituted C1-C20 linear or branched alkyl; substituted or unsubstituted C2-C20 linear or branched alkenyl; substituted or unsubstituted C2-C20 linear or branched alkynyl; substituted or unsubstituted C3-C12 cycloalkyl; substituted or unsubstituted C6-C40 aryl; substituted or unsubstituted C5-C12 arylalkyl; and a polar functional group including at least one selected from oxygen, nitrogen, phosphorus, sulfur, silicon, and boron, and
when R1 to R4 are not hydrogen; halogen; or the polar functional group, at least one combination of R1 and R2 or R3 and R4 may be linked to each other to form a C1-C10 alkylidene group, or R1 or R2 may be linked to any one of R3 and R4 to form a C4-C12 saturated or unsaturated aliphatic ring, or a C6-C24 aromatic ring,

in Chemical Formula 1a,
A and C are each independently a simple bond, or substituted or unsubstituted C1-C5 alkylene,
B is ester,
n1 and n2 are each independently an integer of 0 to 5, and n1+n2 are an integer of 1 to 5, and
X 1 and X 2 are substituents substituted in a benzene ring, and each independently a fluorine atom (F), C1-C5 fluorinated alkyl, C1-C5 fluorinated alkoxy, C6-C20 fluorinated aryl, or C6-C20 fluorinated alkoxyaryl.

5. A liquid crystal cell comprising the vertical alignment layer of claim 1 and a liquid crystal layer.

6. A display device comprising the vertical alignment layer of claim 1 .

Assignees

• Lg Chemical Ltd

Inventors

• Park Eun Seok
• Park Jung Ha
• Choi Dai Seung
• Hwang Seung Yeon
• Lee Min Hyung

Classifications

• C08G2261/1426

  containing carboxy groups (COOH) and/or -C(=O)O-moieties · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title

• C08L45/00

  Compositions of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; Compositions of derivatives of such polymers (of cyclic anhydrides or imides C08L35/00; of cyclic esters of polyfunctional acids C08L31/00) · CPC title

• G02F1/133711

  by organic films, e.g. polymeric films · CPC title

• C09K19/52 Primary

  characterised by components which are not liquid crystals, e.g. additives {with special physical aspect: solvents, solid particles} · CPC title