# US 10,767,113 B2 · Liquid crystal compound containing 2,3,4-trisubstituted benzene and composition thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,767,113 B2 - Document ID: US10767113B2 - Status: Granted - Kind: B2 - Application number: 15/714,234 - Filed: 2017-09-25 - Published: 2018-04-05 - Granted: 2020-09-08 - Earliest claimed: 2016-09-29 - Assignees: Shijiazhuang Chengzhi Yonghua Display Material Co., Ltd. - Applicants: Shijiazhuang Chengzhi Yonghua Display Material Co.,Ltd. - Inventors: Guoliang Yun; Hongmei Cui; Mingxia Wang; Sumin Kang; Yongtao Zhang; Yong Chen - Web page: https://patentgrep.com/patent/US10767113B2 ## CPC - C09K 19/3402: {having oxygen as hetero atom (sugars C09K19/0422)} - C09K 19/04: characterised by the chemical structure of the liquid crystal components {, e.g. by a specific unit} - C09K 19/3003: {Compounds containing at least two rings in which the different rings are directly linked (covalent bond)} - G02F 1/137: characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering - C09K 2019/0437: {the specific unit being an optically active chain used as linking group between rings or as end group} - C09K 2019/0466: {the linking chain being a -CF2O- chain} - C09K 2019/122: {Ph-Ph} - C09K 2019/123: {Ph-Ph-Ph} - C09K 2019/124: {Ph-Ph-Ph-Ph} - C09K 2019/3004: {Cy-Cy} - C09K 2019/3009: {Cy-Ph} - C09K 2019/301: {Cy-Cy-Ph} - C09K 2019/3016: {Cy-Ph-Ph} - C09K 2019/3021: {Cy-Ph-Ph-Cy} - C09K 2019/3025: {Cy-Ph-Ph-Ph} - C09K 2019/3027: {Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene} - C09K 2019/3096: {Cyclobutane rings} - C09K 2019/3422: {the heterocyclic ring being a six-membered ring} - G02F 1/13706: {the liquid crystal having positive dielectric anisotropy} - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE - 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 Provided is a liquid crystal compound containing 2,3,4-trisubstituted benzene, a liquid crystal composition thereof, and a liquid crystal display element or a liquid crystal display comprising the liquid crystal compound or the liquid crystal composition, wherein the liquid crystal composition has a lower viscosity, can achieve a quick response, and further has a moderate dielectric anisotropy Δε, a moderate optical anisotropy Δn, and high stability to heat and light. The liquid crystal display element or liquid crystal display comprising the liquid crystal composition has the properties of a wider nematic phase temperature range, an appropriate birefringence anisotropy, a very high electrical resistivity, a good ultraviolet resistant property, a high charge retention rate, a low vapor pressure etc., and particularly, the liquid crystal compound or the liquid crystal composition has the advantage of a high light transmittance. ## Claims ### Claim 1 A liquid crystal composition, wherein the liquid crystal composition comprises one or more compounds of formula I and one or two compounds of formula II-B, wherein R1 represents an alkyl group having a carbon atom number of 1-10, a fluoro-substituted alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluoro-substituted alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluoro-substituted alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluoro-substituted alkenoxy group having a carbon atom number of 3-8, and any one or more non-connected CH2 in the groups represented by R1 may be substituted with cyclobutyl, cyclopropyl or —O—; Y represents ethyl or vinyl; R2 represents F, OCF3, OCHF2 or OCH2F; each independently represent one of and any fluorobenzene; and m and n each independently represent 1 or 2. ### Claim 2 (depends on 1) The liquid crystal composition according to claim 1, wherein said one or more compounds represented by formula I are one or more of compounds represented by formulas I1 to I24; said liquid crystal composition further comprises one or more compounds represented by formulas II1 to II10; and said one or two compounds represented by formula II-B are one or two of compounds represented by formulas II-B-1 and II-B-2; wherein R11 each independently represents an alkyl having a carbon atom number of 1-6 or an alkenyl group having an atom number of 2-6. ### Claim 3 (depends on 1) The liquid crystal composition according to claim 1, wherein in said liquid crystal composition, the total content in mass percentage of the compounds represented by formula I is 0.5-50%, the total content in mass percentage of the compounds represented by formula II-B is 5-65%. ### Claim 4 (depends on 1) The liquid crystal composition according to claim 1, wherein said liquid crystal composition is a positive liquid crystal composition, and said liquid crystal composition further comprises one or more compounds represented by formula III wherein R4 represents an alkyl group having a carbon atom number of 1-10, a fluoro-substituted alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluoro-substituted alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluoro-substituted alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluoro-substituted alkenoxy group having a carbon atom number of 3-8; and any one or more CH2 in the groups represented by R4 may be substituted with cyclopentyl, cyclobutyl or cyclopropyl; each independently represent: one or two of m represents 1 or 2; Z1 and Z2 each independently represent a single bond, —CF2O—, —CH2CH2— or —CH2O—; and Y2 represents F, a fluoro-substituted alkyl group having a carbon atom number of 1-5, a fluoro-substituted alkoxy group having a carbon atom number of 1-5, a fluoro-substituted alkenyl group having a carbon atom number of 2-5, or a fluoro-substituted alkenoxy group having a carbon atom number of 3-8. ### Claim 5 (depends on 4) The liquid crystal composition according to claim 4, wherein said one or more compounds represented by formula III are one or more of compounds represented by formulae III1 to III26 wherein X1 and X2 each independently represent H or F, but can be neither F nor H at the same time in the same molecular formula; R4 each independently represents an alkyl group having a carbon atom number of 1-10, a fluoro-substituted alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluoro-substituted alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluoro-substituted alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluoro-substituted alkenoxy group having a carbon atom number of 3-8, and any CH2 in the groups represented by R4 may be substituted with cyclopentyl, cyclobutyl or cyclopropyl; the (F)s each independently represent H or F; and Y2 each independently represents F, a fluoro-substituted alkyl group having a carbon atom number of 1-5, a fluoro-substituted alkoxy group having a carbon atom number of 1-5, a fluoro-substituted alkenyl group having a carbon atom number of 2-5, or a fluoro-substituted alkenoxy group having a carbon atom number of 3-8. ### Claim 6 (depends on 1) The liquid crystal composition according to claim 1, wherein said liquid crystal composition is a negative liquid crystal composition, and said liquid crystal composition further comprises one or more compounds represented by formula IV wherein R5 and R6 each independently represents an alkyl group having a carbon atom number of 1-10, a fluoro-substituted alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluoro-substituted alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluoro-substituted alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluoro-substituted alkenoxy group having a carbon atom number of 3-8, and any CH2 in the groups represented by R5 and R6 may be substituted with cyclopentyl, cyclobutyl or cyclopropyl; Z3 and Z4 each independently represent a single bond, —CH2CH2— or —CH2O—; each independently represent one or more of m represents 1 or 2; n represents 0, 1 or 2. ### Claim 7 (depends on 6) The liquid crystal composition according to claim 6, wherein said one or more compounds represented by formula IV are one or more of compounds represented by formulae IV1 to IV11 wherein R5 and R6 each independently represents an alkyl group having a carbon atom number of 1-10, a fluoro-substituted alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluoro-substituted alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluoro-substituted alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluoro-substituted alkenoxy group having a carbon atom number of 3-8, and any CH2 in the groups represented by R5 and R6 may be substituted with cyclopentyl, cyclobutyl or cyclopropyl. ### Claim 8 (depends on 1) The liquid crystal composition according to claim 1, wherein said liquid crystal composition is a negative liquid crystal composition, and said liquid crystal composition further comprises one or more compounds represented by formula V wherein R7 and R8 each independently represents an alkyl group having a carbon atom number of 1-10, a fluoro-substituted alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluoro-substituted alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluoro-substituted alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluoro-substituted alkenoxy group having a carbon atom number of 3-8, and any CH2 in the groups represented by R7 and R8 may be substituted with cyclopentyl, cyclobutyl or cyclopropyl. ### Claim 9 (depends on 4) The liquid crystal composition according to claim 4, wherein said liquid crystal composition further comprises one or more compounds represented by formula VI wherein R91 represents an alkyl group having a carbon atom number of 1-5 or an alkenyl group having a carbon atom number of 2-5; R92 represents an alkyl group having a carbon atom number of 1-5, an alkoxy group having a carbon atom number of 1-5 or an alkenyl group having a carbon atom number of 2-5; and represents ### Claim 10 A compound, represented by formula I2-I4, I6-I13, I15, I16, or I18-I24: wherein R11 each independently represents an alkyl having a carbon atom number of 1-6 or an alkenyl group having an atom number of 2-6. ### Claim 11 (depends on 1) A liquid crystal display element or liquid crystal display comprising the liquid crystal compound or liquid crystal composition of claim 1, wherein said liquid crystal display element or liquid crystal display is an active matrix display element or display or a passive matrix display element or display. ### Claim 12 (depends on 6) The liquid crystal composition according to claim 6, wherein said liquid crystal composition further comprises one or more compounds represented by formula VI wherein R91 represents an alkyl group having a carbon atom number of 1-5 or an alkenyl group having a carbon atom number of 2-5; R92 represents an alkyl group having a carbon atom number of 1-5, an alkoxy group having a carbon atom number of 1-5 or an alkenyl group having a carbon atom number of 2-5; and represents ### Claim 13 (depends on 8) The liquid crystal composition according to claim 8, wherein said liquid crystal composition further comprises one or more compounds represented by formula VI wherein R91 represents an alkyl group having a carbon atom number of 1-5 or an alkenyl group having a carbon atom number of 2-5; R92 represents an alkyl group having a carbon atom number of 1-5, an alkoxy group having a carbon atom number of 1-5 or an alkenyl group having a carbon atom number of 2-5; and represents ### Claim 14 (depends on 10) A liquid crystal display element or liquid crystal display comprising the compound of claim 10, wherein said liquid crystal display element or liquid crystal display is an active matrix display element or display or a passive matrix display element or display. ### Claim 15 (depends on 2) The liquid crystal composition according to claim 2, wherein in said liquid crystal composition, the total content in mass percentage of the compounds represented by formula I is 0.5-50%, the total content in mass percentage of the compounds represented by formula II-B is 5-65%, and the total content in mass percentage of the compounds represented by formula II-1˜II-10 is no more than 30%.