# US 2020/0399539 A1 · Polymerizable compound as well as liquid crystal composition and liquid crystal display device each including polymerizable compound

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2020/0399539 A1
- Document ID: US20200399539A1
- Status: Published application
- Kind: A1
- Application number: 16/968,961
- Filed: 2019-02-14
- Published: 2020-12-24
- Earliest claimed: 2018-03-01
- Assignees: DIC Corporation
- Applicants: DIC Corporation
- Inventors: Masanao Hayashi; Ayaki Hosono; Shota Kosaka
- Web page: https://patentgrep.com/patent/US20200399539A1

## CPC

- C09K 19/56: Aligning agents
- C07C 69/54: Acrylic acid esters; Methacrylic acid esters
- C07C 69/653: Acrylic acid esters; Methacrylic acid esters; Haloacrylic acid esters; Halomethacrylic acid esters
- C09K 19/3066: {in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers}
- C09K 19/3402: {having oxygen as hetero atom (sugars C09K19/0422)}
- C09K 19/38: Polymers
- C09K 19/54: Additives having no specific mesophase {characterised by their chemical composition}
- G02F 1/13: based on liquid crystals, e.g. single liquid crystal display cells
- G02F 1/1337: Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F 1/139: based on orientation effects in which the liquid crystal remains transparent
- C09K 2019/0448: {the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate}
- C09K 2019/3004: {Cy-Cy}
- C09K 2019/3016: {Cy-Ph-Ph}
- C09K 2019/3025: {Cy-Ph-Ph-Ph}
- C09K 2019/3027: {Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene}
- C09K 2019/3425: {Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- G02F: OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS

## Abstract

The present invention provides a compound represented by the general formula (i), which has a partial structure Ki1 represented by one of the general formulae (K-1) to (K-6) and has a ring B with at least one P-Sp- group and with at least one Ri2 (Ri2 denotes a linear or branched alkyl group having 2 to 10 carbon atoms or a linear or branched halogenated alkyl group having 2 to 10 carbon atoms, —CH2— in the alkyl or halogenated alkyl group is optionally substituted with —CH═CH—, —O—, —COO—, or —OCO—, but —O— is not adjacent to another —O—). Thus, the compound in a liquid crystal composition adsorbs to substrates between which the liquid crystal composition (a liquid crystal layer) exists. The compound can hold vertically aligned liquid crystal molecules, can improve alignment stability, and can ensure low-temperature storage stability.

## Claims

### Claim 1

A compound represented by a general formula (i):
wherein
Ri1 denotes a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, or a halogenated alkyl group having 1 to 30 carbon atoms, —CH2— in the alkyl or halogenated alkyl group is optionally substituted with —CH═CH—, —C≡C—, —O—, —NH—, —COO—, —OCO—, or —OCOO—, but —O— is not adjacent to another —O—,
Ri2 denotes a linear or branched alkyl group having 2 to 10 carbon atoms or a linear or branched halogenated alkyl group having 2 to 10 carbon atoms, —CH2— in the alkyl or halogenated alkyl group is optionally substituted with —CH═CH—, —O—, —COO—, or —OCO—, but —O— is not adjacent to another —O—,
a ring A denotes a divalent aromatic group, a divalent alicyclic group, a divalent heterocyclic compound group, a divalent fused ring, or a divalent fused polycyclic ring, a hydrogen atom in these ring structures is optionally substituted with Li1, Li1 denotes a halogen atom, a cyano group, a nitro group, P-Sp-, a monovalent organic group having a group represented by a general formula Ki1, a linear or branched alkyl group having 1 to 10 carbon atoms, or a linear or branched halogenated alkyl group having 1 to 10 carbon atoms, —CH2— in the alkyl or halogenated alkyl group is optionally substituted with —CH═CH—, —C≡C—, —O—, —NH—, —COO—, —OCO—, or —OCOO—, but —O— is not adjacent to another —O—,
a ring B denotes a phenyl group or a naphthyl group, a hydrogen atom in the ring structure is optionally substituted with Li2, Li2 denotes a halogen atom, P-Sp-, a monovalent organic group having a group represented by the general formula Ki1, a linear or branched alkyl group having 1 to 10 carbon atoms, or a linear or branched halogenated alkyl group having 1 to 10 carbon atoms, —CH2— in the alkyl or halogenated alkyl group is optionally substituted with —CH═CH—, —C≡C—, —O—, —COO—, or —OCO—, but —O— is not adjacent to another —O—,
Zi1 denotes a single bond, —O—, —CH═CH—, —CF═CF—, —C≡C—, —COO—, —OCO—, —OCOO—, —CF2O—, —OCF2—, —CH═CHCOO—, —OCOCH═CH—, —CH═C(CH3)COO—, —OCOC(CH3)═CH—, —CH2—CH(CH3)COO—, —OCOCH(CH3)—CH2—, —OCH2CH2O—, or an alkylene group having 1 to 10 carbon atoms, and one —CH2— or two or more nonadjacent —CH2— groups in the alkylene group are optionally substituted with —O—, —COO—, or —OCO—,
Zi3 denotes a single bond, —O—, —CH═CH—, —COO—, —OCO—, —OCOO—, —CH═CHCOO—, —OCOCH═CH—, —CH═C(CH3)COO—, —OCOC(CH3)═CH—, —CH2—CH(CH3)COO—, —OCOCH(CH3)—CH2—, or a linear or branched alkylene group having 1 to 20 carbon atoms, one —CH2— or two or more nonadjacent —CH2— groups in the alkylene group are optionally substituted with —O—, —COO—, or —OCO—,
Ki1 denotes a group represented by one of general formulae (K-1) to (K-6),
RK1 denotes a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, and TK1 independently denotes a group represented by one of general formulae (T-1) to (T-6),
ST1 denotes a single bond, a linear or branched alkylene group having 1 to 15 carbon atoms, or a linear or branched alkenylene group having 2 to 18 carbon atoms, —CH2— in the alkylene or alkylene group is optionally substituted with —O—, —COO—, —C(═O)—, —C(═CH2)—, or —OCO— such that oxygen atoms are not directly adjacent to each other, RT1 denotes an alkyl group having 1 to 5 carbon atoms, —CH2— in the alkyl group is optionally substituted with —O—, —COO—, —C(═O)—, —C(═CH2)—, or —OCO— such that oxygen atoms are not directly adjacent to each other, and RT2 and RT3 independently denote a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and
P denotes a polymerizable group, Sp denotes a spacer group or a single bond, m denotes an integer in the range of 1 to 4, a plurality of As, if present, may be the same or different, a plurality of Zi1s, if present, may be the same or different, a plurality of Ps, if present, may be the same or different, and a plurality of Sps, if present, may be the same or different.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein A in the general formula (i) denotes a ring structure selected from a 1,4-phenylene group, a 1,4-cyclohexylene group, an anthracene-2,6-diyl group, a phenanthrene-2,7-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, an indan-2,5-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and a 1,3-dioxane-2,5-diyl group, and the ring structure is unsubstituted or denotes a group optionally substituted with an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group, or P-Sp-.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein P in the general formula (i) denotes a substituent selected from a group represented by the following general formulae (P-1) to (P-14).

### Claim 4 (depends on 1)

The compound according to claim 1, wherein Ki1 in the general formula (i) is represented by the general formula (K-1) or (K-2).

### Claim 5 (depends on 1)

A liquid crystal composition comprising: a compound represented by the general formula (i) according to claim 1; a polymerizable compound different from the compound represented by the general formula (i); and a nonpolymerizable liquid crystal compound.

### Claim 6 (depends on 5)

The liquid crystal composition according to claim 5, wherein the polymerizable compound is one or two or more compounds represented by a general formula (P):
wherein
Zp1 denotes a fluorine atom, a cyano group, a hydrogen atom, an alkyl group having 1 to 15 carbon atoms in which a hydrogen atom is optionally substituted with a halogen atom, an alkoxy group having 1 to 15 carbon atoms in which a hydrogen atom is optionally substituted with a halogen atom, an alkenyl group having 1 to 15 carbon atoms in which a hydrogen atom is optionally substituted with a halogen atom, an alkenyloxy group having 1 to 15 carbon atoms in which a hydrogen atom is optionally substituted with a halogen atom, or -Spp2-Rp2,
Rp1 and Rp2 denote one of the following formulae (R-I) to (R-VIII),
wherein
* is bonded to Spp1,
R2 to R6 independently denote a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms,
W denotes a single bond, —O—, or a methylene group,
T denotes a single bond or —COO—, and
p, t, and q independently denote 0, 1, or 2,
Spp1 and Spp2 denote a spacer group,
Lp1 and Lp2 independently denote a single bond, —O—, —S—, —CH2—, —OCH2—, —CH2O—, —CO—, —C2H4—, —COO—, —OCO—, —OCOOCH2—, —CH2OCOO—, —OCH2CH2O—, —CO—NRa—, —NRa—CO—, —SCH2—, —CH2S—, —CH═CRa—COO—, —CH═CRa—OCO—, —COO—CRaCH—, —OCO—CRa═CH—, —COO—CRa═CH—COO—, —COO—CRa═CH—OCO—, —OCO—CRa═CH—COO—, —OCO—CRa═CH—OCO—, —(CH2)z—C(═O)—O—, —(CH2)z—O—(C═O)—, —O—(C═O)—(CH)z—, —(C═O)—O—(CH2)z—, —CH2(CH3)C—C(═O)—O—, —CH2(CH3)C—O—(C═O)—, —O—(C═O)—C(CH3)CH2, —(C═O)—O—C(CH3)—CH2, —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —CF—, —CF2O—, —OCF2—, —CF2CH2—, —CH2CF2—, —CF2CF2—, or —C≡C— (wherein Ra independently denotes a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and z denotes an integer in the range of 1 to 4,
Mp2 denotes a 1,4-phenylene group, a 1,4-cyclohexylene group, an anthracene-2,6-diyl group, a phenanthrene-2,7-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, an indan-2,5-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 1,3-dioxane-2,5-diyl group, or a single bond, MP2 is unsubstituted or optionally substituted with an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group, or —Rp1,
Mp1 denotes one of the following formulae (i-11) to (ix-11),
wherein * is bonded to Spp1, and ** is bonded to Lp1, Lp2, or Zp1,
Mp3 denotes one of the following formulae (i-13) to (ix-13),
wherein * is bonded to Zp1, and ** is bonded to Lp2,
mp2 to mp4 independently denote 0, 1, 2, or 3,
mp1 and mp5 independently denote 1, 2, or 3, and
a plurality of Zp1s, if present, may be the same or different, a plurality of Rp1s, if present, may be the same or different, a plurality of Rp2s, if present, may be the same or different, a plurality of Spp1s, if present, may be the same or different, a plurality of Spp2s, if present, may be the same or different, a plurality of Lp1s, if present, may be the same or different, and a plurality of Mp2s, if present, may be the same or different.

### Claim 7 (depends on 5)

A liquid crystal display device in which at least one of two substrates with the liquid crystal compositions according to claim 5 has no alignment film.