Compound, liquid-crystal composition, and radio frequency phase shifter

Patent metadata

Field	Value
Publication number	US-11613701-B2
Application number	US-202117363011-A
Country	US
Kind code	B2
Filing date	Jun 30, 2021
Priority date	Jul 14, 2020
Publication date	Mar 28, 2023
Grant date	Mar 28, 2023

Abstract

A compound is represented by general formula (I), a liquid-crystal composition contains this compound, and devices are made using this liquid-crystal composition. Having a large refractive-index anisotropy Δn and a sufficiently high Tni, highly compatible with liquid-crystal compositions, and exhibiting a high dielectric anisotropy in the radio frequency range, the compound is a useful material for RF phase shifters, phased-array antennae, image recognition devices, distance meters, liquid-crystal displays, liquid-crystal lenses, and birefringent lenses for 3D image display, among other devices.

First claim

What is claimed is:

1. A compound represented by general formula (1):

where R 1 denotes a hydrogen atom or a C1 to C20 linear or C3 to C20 branched or cyclic alkyl group, the alkyl group optionally having any hydrogen atom therein replaced with a halogen atom and optionally having one —CH 2 —therein, or each of two or more independently, replaced with —O—, —S—, —CO—, —CS—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—, —CF═CF—, or —C≡C—, with the proviso that no oxygen atoms are bound directly to one another;
R 2 denotes a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, or a C1 to C20 linear or C3 to C20 branched or cyclic alkyl group optionally having one —CH 2 —therein, or each of two or more independently, replaced with —O—, —S—, —CO—, —CS—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, with the proviso that no oxygen atoms are bound directly to one another, the alkyl group optionally having any hydrogen atom therein replaced with a fluorine atom;
A 1 and A 2 each independently denote a substituted or unsubstituted C3 to C16 hydrocarbon ring or heterocycle, and a plurality of A 2 s may be the same or different;
L 1 and L 2 each independently denote a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a C1 to C20 linear or C3 to C20 branched or cyclic alkyl group optionally having one —CH 2 — therein, or each of two or more independently, replaced with —O—, —S—, —CO—, —CS—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF≡CF—, or with the proviso that no oxygen atoms are bound directly to one another, the alkyl group optionally having any hydrogen atom therein replaced with a fluorine atom;
Z 1 on each occurrence independently denotes a single bond, —CH═CH or —C≡, a plurality of Z 1 s may be the same or different, and at least one of the Z 1 s, or the Z 1 if there is only one Z 1 , denotes C≡C—; and
n1 denotes an integer of 1 to 3.

2. The compound according to claim 1 , wherein:
in general formula (I), A 1 and A 2 each independently denote a group selected from the group consisting of:
(a) a 1,4-cyclohexylene group optionally having one —CH 2 —or two or more nonadjacent —CH 2 —s therein replaced with —O— or —S—;
(b) a 1,4-phenylene group optionally having one —CH═ or two or more nonadjacent —CH═s therein replaced with —N═;
(c) a 1,4-cyclohexenylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, decahydronaphthalene-2,6-diyl, anthracene-2,6-diyl, anthracene-1,4-diyl, anthracene-9,10-diyl, or phenanthrene-2,7-diyl group optionally having at least one hydrogen atom therein replaced with a fluorine or chlorine atom, the naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 5,6,7,8-tetrahydronaphthalene- 1,4-diyl, anthracene-2,6-diyl, anthracene- 1,4-diyl, anthracene-9,10-diyl, or phenanthrene-2,7-diyl group optionally having one —CH— or two or more —CH=s therein replaced with —N═; and
(d) a thiophene-2,5-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, or thieno [3,2-b]thiophene-2,5-diyl group optionally having one —CH═ or two or more nonadjacent —CH=s therein replaced with —N═, unsubstituted or substituted with one or more substituents L 3 , and a plurality of A 2 s may be the same or different;
L 3 on each occurrence independently denotes a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a C1 to C20 linear or C3 to C20 branched or cyclic alkyl group optionally having one —CH 2 — therein, or each of two or more independently, replaced with —O—, —S—, —CO—, —CS—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —CC—, with the proviso that no oxygen atoms are bound directly to one another, the alkyl group optionally having any hydrogen atom therein replaced with a fluorine atom.

3. The compound according to claim 1 , wherein:
general formula (I) is represented by general formula (I-i):

where R 11 on each occurrence independently denotes a hydrogen atom or a C1 to C20 linear or C3 to C20 branched alkyl group, the alkyl group optionally having any hydrogen atom therein replaced with a halogen atom and optionally having one —CH 2 —therein, or each of two or more independently, replaced with —O—, —S—, —CH═CH—, —CF═CF—, or —C≡C—;
R 21 denotes a fluorine atom, a chlorine atom, a nitro group, a cyano group, an isocyano group, or a C1 to C20 linear or C3 to C20 branched or cyclic alkyl group, the alkyl group optionally having any hydrogen atom therein replaced with a fluorine atom and optionally having one —CH 2 — therein, or each of two or more independently, replaced with —O—, —S—, —CH═CH—, —CF═CF—, or —C≡C—;
A 11 and A 21 each independently denote a 1,4-cyclohexylene, tetrahydropyrane-2,5-diyl, dioxane-2,5-diyl, 1,4-phenylene, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 5,6,7,8-tetrahydronaphthalene-1,4-diyl, phenanthrene-2,7-diyl, benzothiophene-2,5-diyl, benzothiophene-2,6-diyl, benzothiazole-2,5-diyl, benzothiazole-2,6-diyl, dibenzothiophene-3,7-diyl, dibenzothiophene-2,6-diyl, or thieno[3,2-b]thiophene-2,5-diyl group, a plurality of A 21 s may be the same or different, and the groups A 11 and A 21 may be unsubstituted or substituted with one or more substituents L 31 ;
L 11 and L 21 each independently denote a hydrogen atom, a fluorine atom, a chlorine atom, or a C1 to C20 linear or C3 to C20 branched or cyclic alkyl group, the alkyl group optionally having any hydrogen atom therein replaced with a fluorine atom and optionally having one —CH 2 —therein, or each of two or more independently, replaced with —O—, —S—, —CF═CF—, or —C≡C—;
L 31 on each occurrence independently denotes a fluorine atom, a chlorine atom, or a C1 to C20 linear or C3 to C20 branched or cyclic alkyl group, the alkyl group optionally having any hydrogen atom therein replaced with a fluorine atom and optionally having one —CH 2 — therein, or each of two or more independently, replaced with —O—, —S—, —CH═CH—, —CF═CF—, and a plurality of L 31 s may be the same or different;
Z 11 on each occurrence independently denotes a single bond or —C≡C—, a plurality of Z 11 s may be the same or different, and at least one of the Z 11 s, or the Z 11 if there is only one Z 11 , denotes C≡C—; and
n11 denotes an integer of 1 to 3.

4. The compound according to claim 1 , wherein:
g

Assignees

• Dainippon Ink & Chemicals

Inventors

• Ikeuchi Takaya
• Hayashi Masanao

Classifications

• C07C319/20

  by reactions not involving the formation of sulfide groups · CPC title

• C09K2019/122

  Ph-Ph · CPC title

• C09K2019/3027

  Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene · CPC title

• C09K19/322

  Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring · CPC title

• C09K19/3066

  in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers · CPC title