Liquid crystal device, method for producing same, and compound

Patent metadata

Field	Value
Publication number	US-10982148-B2
Application number	US-201816486835-A
Country	US
Kind code	B2
Filing date	Feb 2, 2018
Priority date	Feb 20, 2017
Publication date	Apr 20, 2021
Grant date	Apr 20, 2021

Abstract

This liquid crystal display device is provided with: a pair of substrates which have conductive films, respectively; a liquid crystal layer which is arranged between the pair of substrates and contains a liquid crystal; and a liquid crystal control layer which is formed on the substrate-side interface of the liquid crystal layer by means of polymerization of a polymerizable monomer, and which controls the alignment of the liquid crystal. With respect to this liquid crystal display device, at least one of the pair of substrates is not provided with a liquid crystal alignment film, and the liquid crystal control layer contains a compound that has at least one partial structure which is selected from the group consisting of a fluorene structure-containing group, an aromatic amino group and a nitrogen-containing aromatic heterocyclic group.

First claim

The invention claimed is:

1. A liquid crystal device, comprising:
a pair of substrates each having a conductive film;
a liquid crystal layer which is disposed between the pair of substrates and contains a liquid crystal; and
a liquid crystal control layer which is formed at an interface on a side of the substrate of the liquid crystal layer through polymerization of polymerizable monomers and controls alignment of the liquid crystal,
wherein no liquid crystal alignment film is formed on at least one of the pair of substrates, and
wherein the liquid crystal control layer contains a compound [A] having at least one partial structure selected from the group consisting of an aromatic amino group and a nitrogen-containing aromatic heterocyclic group.

2. The liquid crystal device according to claim 1 ,
wherein the compound [A] is at least one selected from the group consisting of the following (i) and (ii):
(i) a polymer of a compound including at least one selected from the group consisting of a partial structure derived from a compound represented by the following Formula (1) and a nitrogen-containing aromatic heterocyclic group, and a radically polymerizable group in the same molecule; and
(ii) a compound including at least one selected from the group consisting of a partial structure derived from a compound represented by the following Formula (1), and a nitrogen-containing aromatic heterocyclic group, and at least one group selected from the group consisting of an alkoxysilyl group, a hydroxysilyl group, a hydroxyl group, a carboxyl group or salts thereof, a sulfo group or salts thereof, an amino group, a quaternary ammonium base, a phosphate group or salts thereof, a phosphoric acid ester group, a phosphonium base and a carbamoyl group in the same molecule:

in Formula (1), R 1 is a monovalent aromatic ring group, and R 2 and R 3 are each independently a hydrogen atom or a monovalent organic group having 1 to 30 carbon atoms, and here, R 2 and R 3 may be mutually bonded to form a ring structure together with the nitrogen atoms to which R 2 and R 3 are bonded, and R 1 and R 3 may be mutually bonded to form a nitrogen-containing condensed ring structure including the nitrogen atoms to which R 1 and R 3 are bonded in the ring.

3. The liquid crystal device according to claim 1 ,
wherein the liquid crystal control layer is formed by a liquid crystal composition that contains at least one selected from the group consisting of a polymerization initiator, a photosensitizer and a polymerization inhibitor.

4. The liquid crystal device according to claim 1 ,
wherein the liquid crystal control layer contains a compound having a partial structure represented by the following Formula (3):
*-L 1 -X 1 —X 2 —X 3 —X 4   (3)

in Formula (3), L 1 is —O—, —CO—, —COO—* 1 , —OCO—* 1 , —NX 5 —, —NX 5 —CO—* 1 , —CO—NX 5 —* 1 , an alkanediyl group having 1 to 6 carbon atoms, —O—X 6 —* 1 , or —X 6 —O—* 1 , here, X 5 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, and X 6 is an alkanediyl group having 1 to 3 carbon atoms, * 1 indicates a bond with X 1 ,
X 1 and X 3 are each independently a single bond, a phenylene group or a cycloalkylene group,
X 2 is a single bond, a phenylene group, a cycloalkylene group, —X 7 —B 1 —* 2 , or —B 1 —* 2 , or —B 1 —X 7 —* 2 , here, X 7 is a phenylene group or a cycloalkylene group, B 1 is a single bond, —COO—* 3 , —OCO—* 3 , or an alkanediyl group having 1 to 3 carbon atoms, * 2 indicates a bond with X 3 , and * 3 indicates a bond with X 7 ,
X 4 is a hydrogen atom, a fluorine atom, an alkyl group having 1 to 18 carbon atoms, a fluoroalkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a fluoroalkoxy group having 1 to 18 carbon atoms, or a hydrocarbon group having a steroid structure and having 17 to 51 carbon atoms, and may include a photoinitiator group, here, when X 4 is a hydrogen atom, a fluorine atom or has 1 to 3 carbon atoms, not all of X 1 , X 2 and X 3 may be a single bond, * indicates a bond.

5. The liquid crystal device according to claim 1 ,
wherein the liquid crystal has negative dielectric anisotropy.

6. A method for producing a liquid crystal device which includes a pair of substrates each having a conductive film, and in which no liquid crystal alignment film is formed on at least one of the pair of substrates, the method comprising:
step (I) of constituting a liquid crystal cell by disposing the pair of substrates to face each other with a layer of a liquid crystal composition including a liquid crystal and polymerizable monomers therebetween; and
step (II) of emitting light to the liquid crystal cell when a voltage is applied between the conductive films,
wherein the liquid crystal composition contains a compound [B] having at least one partial structure selected from the group consisting of an aromatic amino group and a nitrogen-containing aromatic heterocyclic group.

7. The method for producing a liquid crystal device according to claim 6 ,
wherein a content of the compound [B] is 0.01 mass % or more and 10 mass % or less with respect to a total amount of the liquid crystal composition.

8. The method for producing a liquid crystal device according to claim 6 ,
wherein the step (I) is a step in which the liquid crystal composition is applied to one surface of the pair of substrates by ink jet coating, and bonding with the other substrate is then performed to constitute the liquid crystal cell.

9. The method for producing a liquid crystal device according to claim 6 ,
wherein, before the step (I), a step of applying a silane coupling agent to a surface on which the conductive film is formed on at least one of the pair of substrates is provided.

10. The method for producing a liquid crystal device according to claim 6 ,
wherein a step of an annealing treatment is provided between the step (I) and the step (II).

11. The method for producing a liquid crystal device according to claim 6 ,
wherein the step (II) includes a first step of emitting light to the liquid crystal cell when a voltage lower than a voltage at which the liquid crystal is driven is applied and a second step of emitting light to the liquid crystal cell when the voltage at which the liquid crystal is driven is applied after the first step.

12. The liquid crystal device according to claim 2 ,
wherein the liquid crystal control layer is formed by a liquid crystal composition that contains at least one selected from the group consisting of a polymerization initiator, a photosensitizer and a polymerization inhibitor.

13. The liquid crystal device according to claim 2 ,
wherein the liquid crystal control layer contains a compound having a partial structure represented by the following Formula (3):
*-L 1 -X 1 —X 2 —X 3 —X 4   (3)

in Formula (3), L 1 is —O—, —CO—, —COO—* 1 , —OCO—* 1 , —NX 5 —, —NX 5 —CO—* 1 , —CO—NX 5 —* 1 , an alkanediyl group having 1 to 6 carbon atoms, —O—X 6 —* 1 , or —X 6 —O—* 1 , here, X 5 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, and X 6 is an alkanediyl group having 1 to 3 carbon atoms, * 1 indicates a bond with X 1 ,
X 1 and X 3 are each independently a single bond, a phenylene group or a cycloalkylene group,
X 2 is a single bond, a phenylene group, a cycloalkylene group, —X 7 —B 1 —* 2 , or —B 1 —X 7 —* 2 , here, X 7 is a phenylene group or a cycloalkylene group, B 1 is a single bond, —COO—* 3 , —OCO—* 3 , or an alkanediyl group having 1 to

Assignees

• Jsr Corp

Inventors

• Uesaka Yuusuke

Classifications

• C08G77/38

  Polysiloxanes modified by chemical after-treatment · CPC title

• C07D295/096

  with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings · CPC title

• C07D207/09

  Radicals substituted by nitrogen atoms, not forming part of a nitro radical · CPC title

• C07D213/74

  Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals · CPC title

• C07D209/88 Primary

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system · CPC title