US 11,952,525 B2Granted

Compound, composition, liquid crystal composition, and device

AssigneeDIC Corporation

InventorsMasanao Hayashi, Takaya Ikeuchi

Life of this patent

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Abstract

A compound having large refractive index anisotropy (Δn), the effect of increasing the phase transition temperature of a liquid crystal phase, and high solubility, and showing large dielectric anisotropy (Δε) in a high frequency region, a composition containing the compound, a liquid crystal composition, and a device using the liquid crystal composition. The compound has large refractive index anisotropy Δn, sufficiently high Tn-i, and high compatibility with a liquid crystal composition, and shows large dielectric anisotropy in a high frequency region, and is thus useful for a material of an element of a device such as a high-frequency phase shifter, a phased array antenna, an image recognition device, a distance measuring device, a liquid crystal display device, a liquid crystal lens, a birefringent lens for stereoscopic image display.

A compound represented by general formula (I) below,

in the formula,
R1 represents a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl group having 3 to 20 carbon atoms,
any hydrogen atom in the alkyl group may be substituted by a halogen atom,
one or two or more —CH2— in the alkyl group may be each independently substituted by —O—, —S—, —CO—, —CS—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—, —CF═CF—, or —C≡C—, but oxygen atoms are not directly bonded to each other,
A1 and A2 each independently represent a hydrocarbon ring or hetero ring having 3 to 16 carbon atoms, which may be substituted,
when a plurality of A2 are present, they may be the same or different,
L1 and L2 each independently represent 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 linear alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, in which one —CH2— or two or more —CH2— may be each independently substituted by —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—,
oxygen atoms are not directly bonded to each other,
any hydrogen atom in the alkyl group may be substituted by a fluorine atom,
Z1 and Z2 each independently represent a single bond, —CH═CH—, —CF≡CF—, —C≡C—, —COO—, —OCO—, —OCOO—, —CH2O—, —OCH2—, —CF2O—, —OCF2—, —CH═CHCOO—, —OCOCH═CH—, —CH═C(CH3)COO—, —OCOC(CH3)═CH—, —CH2—CH(CH3)COO—, —OCOCH(CH3)—CH2—, —OCH2CH2O—, —CH═N—N═CH—, —CH═N—, —N═CH—, —N═N—, or an alkylene group having 1 to 20 carbon atoms,
one or two or more —CH2— in the alkylene group may be each independently substituted by —O—, —COO—, or —OCO—, but oxygen atoms are not directly bonded to each other,
when a plurality of Z2 are present, they may be the same or different,
m represents 0 or 1, and
n1 represents an integer of 0 to 3.

11 more elements

Facts

Application

18/015,076Filed 29 Jul 2021

Priority

JP 2020-1337166 Aug 2020

Published

US 2023/0313044 A15 Oct 2023

Granted

9 Apr 2024

Term ends

Not estimatedThe source records don’t support an estimate.

Classification13 codes

C09K 19/32
Non-steroidal liquid crystal compounds: containing condensed ring systems, i.e. fused, bridged or spiro ring systems
C09K 19/322
Containing condensed ring systems, i.e. fused, bridged or spiro ring systems: compounds containing a naphthalene ring or a completely or partially…
C07C 25/18
Compounds containing at least one halogen atom bound to a six-membered aromatic ring: polycyclic aromatic halogenated hydrocarbons
C07C 25/24
Compounds containing at least one halogen atom bound to a six-membered aromatic ring: halogenated aromatic hydrocarbons with unsaturated side chains

Abstract

Claims16