CN115612501A - Liquid crystal composition, liquid crystal medium and electro-optical display element - Google Patents
Liquid crystal composition, liquid crystal medium and electro-optical display element Download PDFInfo
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 107
- 239000000203 mixture Substances 0.000 title claims abstract description 71
- 150000001875 compounds Chemical class 0.000 claims abstract description 104
- 125000000304 alkynyl group Chemical group 0.000 claims description 54
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 41
- 238000006467 substitution reaction Methods 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 230000004044 response Effects 0.000 abstract description 18
- 230000000694 effects Effects 0.000 abstract description 9
- -1 prop-1-enyl Chemical group 0.000 description 43
- 239000000047 product Substances 0.000 description 30
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 230000009286 beneficial effect Effects 0.000 description 10
- 238000007254 oxidation reaction Methods 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 239000013067 intermediate product Substances 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 5
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 3
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000006880 cross-coupling reaction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- YCLAMANSVUJYPT-UHFFFAOYSA-L aluminum chloride hydroxide hydrate Chemical compound O.[OH-].[Al+3].[Cl-] YCLAMANSVUJYPT-UHFFFAOYSA-L 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011978 dissolution method Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
- C09K2019/3408—Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems
Abstract
The application provides a liquid crystal composition, a liquid crystal medium and an electro-optical display element, wherein the liquid crystal composition comprises at least one or more compounds with a formula I, and X and K are introduced into the structure of the formula I 1 、K 2 、A 1 、A 2 、R 1 And R 2 The groups enable the dipole moment of the compound molecules to face the same direction, the polarity of the compound is reduced, the viscosity of the compound is further reduced, the response speed is also improved, the response time is shortened, and the display effect and the performance of the electro-optic display element are improved.
Description
Technical Field
The application relates to the technical field of display, in particular to a liquid crystal composition, a liquid crystal medium and an electro-optical display element.
Background
Liquid crystal compounds are widely used in displays of electronic devices including, but not limited to, watches, mobile phones, televisions, and computers. The contrast and the response time of the display are affected by the optical, electrical and mechanical properties of the liquid crystal compound, so that the contrast and the response time of the display are poor, and the display effect and the performance of the display are affected. For example: at a voltage of 0V, the liquid crystal molecules in a VA (vertical alignment mode) display are aligned in a direction perpendicular to the glass substrate, and incident light perpendicular to the glass substrate cannot pass through the liquid crystal molecules, thereby exhibiting a good dark state effect. The IPS and FFS displays have poor contrast and response speed.
However, the optical, electrical and mechanical properties of the liquid crystal compound depend on its molecular structure and the structure of the substituent groups. Therefore, in order to improve the display effect and performance of the display, it is necessary to develop a liquid crystal material with faster response and higher contrast.
Disclosure of Invention
The application provides a liquid crystal composition, a liquid crystal medium and an electro-optical display element, which are used for solving the technical problem that the display effect of a display is insufficient due to small polarity, high viscosity and low response speed of a liquid crystal material.
In a first aspect, the present application provides a liquid crystal composition comprising at least one or more compounds having formula I:
wherein A is 1 、A 2 Each independently a single bond, O or S;
x is a single bond, -O-, -S-, -CH 2 -、-CH 2 CH 2 -or-CF 2 -；
K 1 、K 2 Each independently is H or F;
R 1 、R 2 each independently is H, F, cl, br, I, CN, SCN, NCS, CF 3 Or SF 5 Or each independently is C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 Alkynyloxy, and C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 The terminal group of the alkynyloxy group can be substituted by H, CN or CF 3 Substituted, and/or C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 Alkynyloxy having at least one CH 2 The radicals being able to be substituted by-O-, -S-, -SO 2 -、-CO-、-C(O)O-、-OC(O)-、-OC(O)O-、-CF 2 O-、-OCF 2 -、 -CH 2 CH 2 -、-CF 2 CF 2 -、-CF 2 CH 2 -、-CH 2 CF 2 -、-CHF-CHF-、-CH 2 O、-OCH 2 -, -CF = CH-, -CH = CF-, -CF = CF-, -CH = CH-or-C ≡ C-substitution, and/or C ≡ C-substitution 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 At least one H of the alkynyloxy groups can be substituted by F, cl, br or I.
Optionally, in some embodiments herein, X is-O-or-S-.
Optionally, in some embodiments of the present application, A 1 、A 2 Each independently is S or O.
Optionally, in some embodiments of the present application, K 1 、K 2 At least one of the two is F.
Optionally, in some embodiments herein, R 1 、R 2 Each independently is C 1-7 Alkyl radical, C 1-7 Alkoxy radical, C 2-7 Alkenyl radical, C 2-7 Alkenyloxy radical, C 2-7 Alkynyl or C 2-7 An alkynyloxy group.
Alternatively, in some embodiments herein, the compound having formula I has the following structural formula:
any one of, wherein,
R 7 is C 1-15 Alkyl radical, C 2-15 Alkenyl or C 2-15 Alkynyl, and R 7 In which there are one or two CH 2 The radicals being able to be substituted by-O-, -CO-; -C (O) O-, -OC (O) -, -CF 2 O-、-OCF 2 -、-CH 2 O or-OCH 2 -substitution;
R 2 is H, F, cl, br, I, CN, SCN, NCS, CF 3 Or SF 5 Or is C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 Alkynyloxy, and C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 The terminal group of the alkynyloxy radical being able to be replaced by H, CN or CF 3 Substituted, and/or C 1-15 Alkyl radical, C 1-15 Alkoxy radicalBase, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy, C 2-15 Alkynyl or C 2-15 Alkynyloxy having at least one CH 2 The radicals being able to be substituted by-O-, -S-, -SO 2 -、-CO-、 -C(O)O-、-OC(O)-、-OC(O)O-、-CF 2 O-、-OCF 2 -、-CH 2 CH 2 -、-CF 2 CF 2 -、-CF 2 CH 2 -、 -CH 2 CF 2 -、-CHF-CHF-、-CH 2 O、-OCH 2 -, -CF = CH-, -CH = CF-, -CF = CF-, -CH = CH-or-C ≡ C-substitution, and/or C ≡ C-substitution 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 At least one H of the alkynyloxy groups can be substituted by F, cl, br or I.
Optionally, in some embodiments herein, IB is selected from the following structural formulas:
Optionally, in some embodiments herein, the liquid crystal composition further comprises at least one or more compounds having formula II and/or at least one or more compounds having formula III:
R 3 -R'-R 4 formula II.
Wherein R is 3 、R 4 Each independently is C 1-10 Alkyl radical, C 1-10 Alkoxy radical, C 2-10 Alkenyl radical, C 2-10 Alkenyloxy radical, C 2-10 Alkynyl or C 2-10 Alkynyloxy, and R 3 、R 4 Wherein at least one H atom can be substituted by F, cl, br or I;
r' is:
R 5 -R"-R 6 and (3) a formula III.
Wherein R is 5 、R 6 Each independently is C 1-10 Alkyl radical, C 1-10 Alkoxy radical, C 2-10 Alkenyl radical, C 2-10 Alkenyloxy radical, C 2-10 Alkynyl or C 2-10 Alkynyloxy, and R 5 、R 6 Wherein at least one H atom can be substituted by F, cl, br or I.
R' is:
optionally, in some embodiments of the present application, the mass percentage of the compound having formula I is 1% to 50%, the mass ratio of the compound having formula II is 1% to 90%, and the mass percentage of the compound having formula III is 1% to 90%.
Optionally, in some embodiments of the present application, the mass percentage of the compound having formula I is 1% to 25%, the mass ratio of the compound having formula II is 10% to 70%, and the mass percentage of the compound having formula III is 10% to 70%.
In a second aspect of the present application, there is provided a liquid crystal medium comprising the liquid crystal composition described above.
A third aspect of the present application is to provide an electro-optical display element comprising a liquid crystal layer made of the above liquid crystal medium.
The application provides a liquid crystal composition comprising a compound having formula I by introducing X, K into the structure of formula I 1 、K 2 、A 1 、A 2 、R 1 And R 2 And the like, so that the dipole moments of the molecules of the compound face to the same direction, the polarity of the compound is reduced, the viscosity of the compound is further reduced, the response speed is also improved, the response time is shortened, and the display effect and the performance of the electro-optic display element are improved.
Detailed Description
The technical solutions in the embodiments of the present application will be described clearly and completely below, and it should be understood that the described embodiments are only a part of the embodiments of the present application, and not all embodiments. All other embodiments obtained by a person skilled in the art based on the embodiments in the present application without making any creative efforts shall fall within the protection scope of the present application. Furthermore, it should be understood that the detailed description and specific examples, while indicating preferred embodiments of the present application, are given by way of illustration and explanation only, and are not intended to limit the present application.
The present application provides a liquid crystal composition, a liquid crystal medium, and an electro-optical display element, each of which is described in detail below. It should be noted that the following description of the embodiments is not intended to limit the preferred order of the embodiments in the present application. In the following embodiments, the description of each embodiment has its own emphasis, and reference may be made to the related description of other embodiments for parts that are not described in detail in a certain embodiment.
Embodiments of the present application provide a liquid crystal composition comprising at least one or more compounds having formula I:
wherein, A 1 、A 2 Each independently a single bond, O or S.
X is a single bond, -O-, -S-, -CH 2 -、-CH 2 CH 2 -or-CF 2 -. In one embodiment, X is represented by O, and a dibenzofuran structure is introduced into formula I, which is useful for increasing the polarity of the liquid crystal compound. In another embodiment, X is S, and a dibenzothiophene structure is introduced into the formula I, so that the solubility of the liquid crystal compound is improved.
K 1 、K 2 Each independently is H or F. In one embodiment, K 1 、K 2 At least one of the two is F; when K is 1 、K 2 When both are F, it is advantageous to improve the polarity of the liquid crystal compound. In a specific example, A 1 、A 2 Each independently is O. X is-O-. K is 1 、K 2 Are all F. As shown in the formula I, F and O face to the same side in the molecule, so that the dipole moments of the molecules face to the same direction, which is beneficial to improving the polarity of the liquid crystal compound, thereby being beneficial to reducing the viscosity of the liquid crystal compound and further improving the response speed of the liquid crystal compound.
R 1 、R 2 Each independently of the others being H, F, cl, br, I, CN, SCN, NCS (isothiocyanato), CF 3 Or SF 5 Or each independently is C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 Alkynyloxy, and C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 The terminal group of the alkynyloxy group can be substituted by H, CN or CF 3 Substituted, and/or C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 Alkynyloxy having at least one CH 2 The radicals being able to be substituted by-O-, -S-, -SO 2 -、-CO-、-C(O)O-、-OC(O)-、-OC(O)O-、-CF 2 O-、-OCF 2 -、 -CH 2 CH 2 -、-CF 2 CF 2 -、-CF 2 CH 2 -、-CH 2 CF 2 -、-CHF-CHF-、-CH 2 O、-OCH 2 -, -CF = CH-, -CH = CF-, -CF = CF-, -CH = CH-, or-C ≡ C-substitution. And/or C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 Alkynyloxy groups in which one or more H can be replaced by F, cl, br or I, are preferred, wherein one or more H is replaced by F or Cl.
It should be noted that:
the above-mentioned "alkyl", "alkenyl" or "alkynyl" represents a straight-chain or branched aliphatic hydrocarbon group having 1 to 15 (i.e., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15) carbon atoms.
R in formula I 1 And R 2 Each independently represents an alkyl group, which may be linear or branched. Each of these groups is preferably straight-chain, having 1, 2, 3, 4, 5, 6 or 7 carbon atoms and is accordingly preferably methyl, ethyl, propyl, butyl, pentyl, hexyl or heptyl.
R in the formula I 1 And R 2 Each independently represents an alkenyl or alkynyl group having 2 to 15 carbon atoms, which may be linear or branched and have at least one carbon-carbon double bond or carbon-carbon triple bond. It is preferably a straight-chain alkenyl or alkynyl group having 2 to 7 carbon atoms. Concretely, it is vinyl, prop-1-enyl, prop-2-enyl, but-1-enyl, but-2-enyl, but-3-enyl, pent-1-enyl, pent-2-enyl, pent-3-enyl, pent-4-enyl, hex-1-enyl, hex-2-enyl, hex-3-enyl, hex-4-enyl, hex-5-enyl, hept-1-enyl, hept-2-enyl, hept-3-enyl, hept-4-enyl, hept-5-enyl, hept-6-enyl, ethynyl, prop-1-ynyl, prop-2-ynyl, but-1-ynyl, but-2-ynyl, but-3-ynyl, pent-1-ynyl, pent-2-ynylAlkynyl, pent-3-ynyl, pent-4-ynyl, hex-1-ynyl, hex-2-ynyl, hex-3-ynyl, hex-4-ynyl, hex-5-ynyl, hept-1-ynyl, hept-2-ynyl, hept-3-ynyl, hept-4-ynyl, hept-5-ynyl or hept-6-ynyl, and the alkenyl may be both E and Z isomers. Of alkenyl and alkynyl groups, preferred is prop-2-enyl, but-3-enyl, pent-2-enyl, pent-3-enyl, pent-4-enyl, prop-2-ynyl, but-3-ynyl, pent-2-ynyl, pent-3-ynyl or pent-4-ynyl.
Groups or substituents of the compounds of the formula I according to the above-described embodiments of the present application or in the form of optically active or stereoisomeric groups, substituents or compounds according to the compounds of the formula I themselves, which have an asymmetric or chiral center, are likewise included in the scope of protection of the present application. The compounds of the formula I mentioned above can exist in the form of isomers, such as pure enantiomers, diastereomers, E or Z isomers or as mixtures of a plurality of isomers in any desired ratio, for example as racemates, E/Z isomer mixtures.
In one embodiment, A is defined above as in formula I 1 In the case of O, R 1 And R 2 Preference is given to alkyl having 1 to 7 carbon atoms, particularly preferably 2 to 5 carbon atoms. In which A is 2 In the case of a single bond or O, R 2 Preferably represents alkyl, alkenyl or alkynyl, particularly preferably alkyl having 1 to 7 carbon atoms. At R 1 And R 2 The sum of the carbon atoms is preferably 4, 5, 6, 7, 8, 9, 10, particularly preferably 5, 6, 7, 8, 9.
In another embodiment, when A is in formula I above 1 In the case of a single bond, R 1 And R 2 Alkyl groups having 1 to 7 carbon atoms are preferred, with 2 to 5 carbon atoms being particularly preferred. In which A is 2 In the case of a single bond or O, R 2 Preferably represents alkyl, alkenyl or alkynyl, particularly preferably alkyl having 1 to 7 carbon atoms. At R 1 And R 2 The sum of the carbon atoms is preferably 4, 5, 6, 7, 8, 9, 10, particularly preferably 5, 6, 7, 8, 9.
In some embodiments, R 1 、R 2 Each independently represents C 2-7 Alkyl radical, C 3-6 Alkenyl radical, C 3-6 Alkynyl or CF 3 And R 1 And R 2 One or two CH of the group 2 The radicals being substituted by-O-, -CO-) -C (O) O-, -OC (O) -, -CF 2 O-、-OCF 2 -、-CH 2 O or-OCH 2 -substitution.
In other embodiments of the present application, R 1 、R 2 Each independently is C 1-7 Alkyl radical, C 1-7 Alkoxy radical, C 2-7 Alkenyl radical, C 2-7 Alkenyloxy radical, C 2-7 Alkynyl or C 2-7 Alkynyloxy, and C 1-7 Alkyl radical, C 1-7 Alkoxy radical, C 2-7 Alkenyl, C 2-7 Alkenyloxy radical, C 2-7 Alkynyl or C 2-7 Having at least one or more CH groups in alkynyloxy groups 2 The radicals being able to be substituted by-O-, -C (O) O-; -OC (O) -, -CF 2 O-、-OCF 2 -、-CH 2 CH 2 -、-CH 2 O、-OCH 2 -, -CH = CH-or-C ≡ C-substitution; and C 1-7 Alkyl radical, C 1-7 Alkoxy radical, C 2-7 Alkenyl radical, C 2-7 Alkenyloxy radical, C 2-7 Alkynyl or C 2-7 One or more H of the alkynyloxy groups can be substituted by F. In one embodiment, R 1 、R 2 Each independently represents H or F, when R is 1 、R 2 When each is independently represented by F, it is advantageous to increase the polarity of the liquid crystal compound. In another embodiment, R 1 、R 2 Each independently is C 1-7 Alkyl radical, C 1-7 Alkoxy radical, C 2-7 Alkenyl radical, C 2-7 Alkenyloxy radical, C 2-7 Alkynyl or C 2-7 An alkynyloxy group.
In other embodiments of the present application, the compound having formula I has the following structural formula:
any one of (1), wherein R 7 Is C 1-15 Alkyl radical, C 2-15 Alkenyl or C 2-15 Alkynyl, and R 7 In which there are one or two CH 2 The radicals being able to be substituted by-O-, -CO- ] -C (O) O-, -OC (O) -, -CF 2 O-、-OCF 2 -、-CH 2 O or-OCH 2 -substitution. R 2 Is H, F, cl, br, I, CN, SCN, NCS, CF 3 Or SF 5 Or is C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 Alkynyloxy, and C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 The terminal group of the alkynyloxy group can be substituted by H, CN or CF 3 Substituted, and/or C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 Alkynyloxy having at least one CH 2 The radicals being able to be substituted by-O-, -S-, -SO 2 -、-CO-、-C(O)O-、-OC(O)-、-OC(O)O-、-CF 2 O-、-OCF 2 -、-CH 2 CH 2 -、-CF 2 CF 2 -、-CF 2 CH 2 -、-CH 2 CF 2 -、-CHF-CHF-、-CH 2 O、-OCH 2 -, -CF = CH-, -CH = CF-, -CF = CF-, -CH = CH-or-C ≡ C-substitution, and/or C ≡ C-substitution 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 At least one H of the alkynyloxy groups can be substituted by F, cl, br or I.
The structural formula of the IA-IX compound is introduced with a dibenzofuran structure or a dibenzothiophene structure, and the p-K 1 、K 2 、 A 1 And A 2 Optimizing and selecting the preferable group which is beneficial to improving the polarity of the liquid crystal compound to obtain the compound with higher dielectric, higher polarity and low viscosity. It is noted that the liquid crystal composition may comprise one or more of the above-mentioned IA-IX compounds.
In other embodiments of the present application, IB is selected from the following structural formulas:
IH is selected from the following structural formulas:
IN is selected from the following structural formulas:
IQ is selected from the following structural formulas:
IT is selected from the following structural formulae:
In one embodiment, the compounds having formula I may be prepared by the following method:
s1, performing an addition reaction on a first compound to generate an addition product, wherein the first compound has a structural formula:
the structural formula of the addition product is:
s2, carrying out oxidation reaction on the addition product to obtain an oxidation product, wherein the structural formula of the oxidation product is as follows:
s3, carrying out cross coupling reaction on a second compound and the oxidation product to generate a coupling product, wherein the structural formula of the second compound is as follows:
the structural formula of the coupling product is:
s4, carrying out condensation reaction on the coupling product to generate a target product, wherein the structural formula of the target product is as follows:
the reaction process is as follows:
in the structural formulas of the first compound, the addition product, the oxidation product, the second compound, the coupling product and the target product, A 1 、A 2 Each independently a single bond, O or S.
K 1 、K 2 Each independently is H or F.
R 1 、R 2 Each independently of the others being H, F, cl, br, I, CN, SCN, NCS (isothiocyanato), CF 3 Or SF 5 Or each independently is C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 Alkynyloxy, and C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 The terminal group of the alkynyloxy group can be substituted by H, CN or CF 3 Substitution; and/or C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 Alkynyloxy having at least one CH 2 The radicals being able to be substituted by-O-, -S-, -SO 2 -、-CO-、-C(O)O-、-OC(O)-、-OC(O)O-、-CF 2 O-、-OCF 2 -、 -CH 2 CH 2 -、-CF 2 CF 2 -、-CF 2 CH 2 -、-CH 2 CF 2 -、-CHF-CHF-、-CH 2 O、-OCH 2 -, -CF = CH-, -CH = CF-, -CF = CF-, -CH = CH-or-C ≡ C-substitution, and/or C ≡ C-substitution 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 Alkynyloxy has one or more H groups which can be substituted by F, cl, br or I.
In another embodiment, the compounds of formula I may be prepared by the following method:
s10, carrying out addition reaction on a first compound to generate an addition product, wherein the first compound has a structural formula as follows:
the structural formula of the addition product is as follows:
s20, carrying out oxidation reaction on the addition product to obtain an oxidation product, wherein the structural formula of the oxidation product is as follows:
s30, carrying out cross coupling reaction on a second compound and an oxidation product to generate a coupling product, wherein the structural formula of the second compound is as follows:
the structural formula of the coupling product is:
s40, carrying out condensation reaction on the coupling product in weak base to generate a first intermediate product, wherein the structural formula of the first intermediate product is as follows:
s50, carrying out rearrangement reaction on the first intermediate product to generate a second intermediate product, wherein the structural formula of the second intermediate product is as follows:
s60, carrying out condensation reaction on the second intermediate product to obtain a target product, wherein the structural formula of the target product is as follows:
the reaction process is as follows:
in the structural formulas of the first compound, the addition product, the oxidation product, the second compound, the coupling product, the first intermediate product, the second intermediate product and the target product, A 1 、A 2 Each independently a single bond, O or S.
K 1 、K 2 Each independently is H or F.
R 1 、R 2 Each independently of the other is H, F, cl, br, I, CN, SCN, NCS (isothiocyanato), CF 3 Or SF 5 Or each independently is C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 Alkynyloxy, and C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 The terminal group of the alkynyloxy radical being able to be replaced by H, CN or CF 3 Substitution; and/or C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 Alkynyloxy having at least one CH 2 The radicals being able to be substituted by-O-, -S-, -SO 2 -、-CO-、-C(O)O-、-OC(O)-、-OC(O)O-、-CF 2 O-、-OCF 2 -、 -CH 2 CH 2 -、-CF 2 CF 2 -、-CF 2 CH 2 -、-CH 2 CF 2 -、-CHF-CHF-、-CH 2 O、-OCH 2 -, -CF = CH-, -CH = CF-, -CF = CF-, -CH = CH-or-C ≡ C-substitution, and/or C ≡ C-substitution 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 Alkynyloxy has one or more H groups which can be substituted by F, cl, br or I.
In other embodiments of the present application, a liquid crystal composition comprises: comprising at least one or more compounds of formula I, at least one or more compounds of formula II, and/or at least one or more compounds of formula III:
the structures of the compounds of formula I are as described above and are therefore not described herein in detail.
The compound having formula II is:
R 3 -R'-R 4 formula II.
Wherein R is 3 、R 4 Each independently is C 1-10 Alkyl radical, C 1-10 Alkoxy radical, C 2-10 Alkenyl radical, C 2-10 Alkenyloxy radical, C 2-10 Alkynyl or C 2-10 Alkynyloxy, and R 3 、R 4 Wherein at least one H atom can be substituted by F, cl, br or I.
R' is:
by adding the compound having formula II to the liquid crystal composition, it is advantageous to reduce the viscosity of the liquid crystal composition, increase the optical anisotropy (Δ n) of the liquid crystal composition, and improve the clearing point (Tni) of the composition.
The compound having formula III is:
R 5 -R″-R 6 formula III.
Wherein R is 5 、R 6 Each independently is C 1-10 Alkyl radical, C 1-10 Alkoxy radical, C 2-10 Alkenyl radical, C 2-10 Alkenyloxy radical, C 2-10 Alkynyl or C 2-10 Alkynyloxy, and R 5 、R 6 Wherein at least one H atom can be substituted by F, cl, br or I.
R' is:
by adding the compound with the formula III into the liquid crystal composition, the viscosity of the liquid crystal composition is favorably reduced, the dielectric of the liquid crystal composition is increased, and the clearing point of the liquid crystal composition is improved, so that the low-temperature performance of the liquid crystal composition is improved.
In some embodiments, the liquid crystal composition comprises the following components in percentage by mass: 1% -50% of a compound having formula I, 1% -90% of a compound having formula II, and 1% -90% of a compound having formula III. In another embodiment, the liquid crystal composition comprises the following components by mass percent: 1% -40% of a compound having formula I, 5% -70% of a compound having formula II, and 5% -70% of a compound having formula III. In another embodiment, the liquid crystal composition comprises the following components by mass percent: 1% -25% of a compound having formula I, 10% -70% of a compound having formula II, and 10% -70% of a compound having formula III. In particular, the liquid crystal composition may include one or more compounds having formula I, and when there are a plurality of compounds having formula I, the mixing ratio of the plurality of compounds having formula I is not limited in this example, and may be mixed in any ratio. The liquid crystal composition may also include one or more compounds having formula II, and when there are a plurality of compounds having formula II, the present embodiment does not limit the mixing ratio of the plurality of compounds having formula II, and the compounds may be mixed in any ratio. The liquid crystal composition may further include one or more compounds having formula III, and when there are a plurality of compounds having formula III, the mixing ratio of the plurality of compounds having formula III is not limited in this example, and may be mixed in any ratio.
In other embodiments of the present application, a liquid crystal medium is provided, which includes the above liquid crystal composition, and the liquid crystal composition is applied to the liquid crystal medium, and the liquid crystal composition has low viscosity, large polarity, fast response, and the like, has positive significance for developing a fast response display device, is suitable for blending of mixed liquid crystal, and is beneficial to improving the polarity of the liquid crystal medium, increasing the dielectric anisotropy of the liquid crystal medium, improving the clearing point (Tni, unit:. Degree. C) of the liquid crystal medium, and improving the low temperature performance of the liquid crystal medium. In some embodiments, the liquid crystal medium containing the liquid crystal composition provided in the embodiments of the present application is applied to a display in VA, ECB, PALC, FFS or IPS mode, and the display effect and performance of the display are improved.
In other embodiments of the present application, an electro-optic display element is provided that includes a liquid crystal layer made from the liquid crystal medium described above. The photoelectric performance of the electro-optical display element is improved, and the display effect and performance of the electro-optical display element are improved.
The technical effects of the present application will be further clarified below with reference to specific examples.
In each of the following examples, the liquid crystal composition was prepared by a thermal dissolution method comprising the steps of:
s100, weighing and preparing the components of the liquid crystal composition according to the mass percentage, wherein the weighing and adding sequence has no specific requirement, and the components are usually weighed and mixed at one time according to the sequence that the melting point of the liquid crystal compound is from low to high.
S200, heating and stirring at the temperature of 60-100 ℃ to fully dissolve and mix the components.
And S300, cooling to room temperature, and packaging to obtain a target sample.
Unless otherwise stated, the percentages in this example are mass percentages, and the temperature units are; tni represents the clearing point (unit:. Degree. C.) of the liquid crystal composition; Δ n represents the optical anisotropy at 25 ℃, n e Is the refractive index of the extraordinary ray; γ 1 represents the rotational viscosity at 25 ℃ (unit: mPas); Δ ε represents the dielectric anisotropy at 25 ℃,. Epsilon ⊥ In the dielectric constant perpendicular to the long axis of the liquid crystal molecules, K11 is a splay elastic constant, and K33 is a bend elastic constant.
Example 1
Providing a liquid crystal composition, which comprises the following components in percentage by mass:
the performance parameters of the liquid crystal composition of this example are as follows in table 1:
TABLE 1
The liquid crystal composition is placed at the temperature of minus 20 ℃ for 480h without crystallization.
Example 2
The liquid crystal composition comprises the following components in percentage by mass:
the performance parameters of the liquid crystal composition of this example are as follows:
TABLE 2
The liquid crystal composition is placed at the temperature of minus 20 ℃ for 480h without crystallization.
Example 3
The liquid crystal composition comprises the following components in percentage by mass:
the performance parameters of the liquid crystal composition of this example are as follows in table 3:
TABLE 3
The liquid crystal composition is placed at the temperature of minus 20 ℃ for 480h without crystallization.
Example 4
The liquid crystal composition comprises the following components in percentage by mass:
the performance parameters of the liquid crystal composition of this example are as follows in Table 4:
TABLE 4
The liquid crystal composition is placed at the temperature of minus 20 ℃ for 480h without crystallization.
Example 5
Providing a liquid crystal composition, which comprises the following components in percentage by mass:
the performance parameters of the liquid crystal composition of this example are as follows:
TABLE 5
The liquid crystal composition is placed at-20 ℃ for 480h without crystallization.
Example 6
Providing a liquid crystal composition, which comprises the following components in percentage by mass:
the performance parameters of the liquid crystal composition of this example are as follows in Table 6:
TABLE 6
The liquid crystal composition is placed at the temperature of minus 20 ℃ for 480h without crystallization.
The performance parameters of the liquid crystal compositions of the above examples show that the liquid crystal compositions of the present application have a large polarity as a whole, i.e., Δ ∈, and play a favorable role in the response speed of liquid crystals. The response speed of displays such as IPS and FFS is determined by gamma 1/K 11 Judging, wherein the smaller the ratio is, the faster the response speed is; the response speed of VA display is based on gamma 1/K 33 It is judged that the smaller the ratio, the faster the response speed. As can be shown by the performance parameters of the above examples, the liquid crystal composition of the present application has the advantages of large polarity, low viscosity, fast response, etc.
The foregoing provides a detailed description of the present application, and the principles and embodiments of the present application are described herein using specific examples, which are merely used to help understand the method and the core ideas of the present application; meanwhile, for a person skilled in the art, according to the idea of the present application, there may be variations in specific embodiments and application ranges, and in summary, the content of the present specification should not be construed as a limitation to the present application.
Claims (12)
1. A liquid crystal composition comprising at least one or more compounds having formula I:
wherein A is 1 、A 2 Each independently a single bond, O or S;
x is a single bond, -O-, -S-, -CH 2 -、-CH 2 CH 2 -or-CF 2 -；
K 1 、K 2 Each independently is H or F;
R 1 、R 2 each independently is H, F, cl, br, I, CN, SCN, NCS, CF 3 Or SF 5 Or each independently is C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 Alkynyloxy, and C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 The terminal group of the alkynyloxy radical being able to be replaced by H, CN or CF 3 Substituted, and/or C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 Alkynyloxy having at least one CH 2 The radicals being able to be substituted by-O-, -S-, -SO 2 -、-CO-、-C(O)O-、-OC(O)-、-OC(O)O-、-CF 2 O-、-OCF 2 -、-CH 2 CH 2 -、-CF 2 CF 2 -、-CF 2 CH 2 -、-CH 2 CF 2 -、-CHF-CHF-、-CH 2 O、-OCH 2 <xnotran> -, -CF = CH-, -CH = CF-, -CF = CF-, -CH = CH- -C ≡ C- , / C </xnotran> 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 At least one H of the alkynyloxy groups can be substituted by F, cl, br or I.
2. The liquid crystal composition according to claim 1, wherein X is-O-or-S-.
3. Liquid crystal composition according to claim 1 or 2, characterized in that A is 1 、A 2 Each independently is S or O.
4. The liquid crystal composition according to claim 1 or 2, wherein K is 1 、K 2 At least one of the two is F.
5. The liquid crystal composition according to claim 1 or 2, wherein R is 1 、R 2 Each independently is C 1-7 Alkyl radical, C 1-7 Alkoxy radical, C 2-7 Alkenyl radical, C 2-7 Alkenyloxy radical, C 2-7 Alkynyl or C 2-7 An alkynyloxy group.
6. The liquid crystal composition of claim 1, wherein the compound having formula I has the following structural formula:
any one of, wherein,
R 7 is C 1-15 Alkyl radical, C 2-15 Alkenyl or C 2-15 Alkynyl, and R 7 In which there are one or two CH 2 The radicals being able to be substituted by-O-, -CO- ] -C (O) O-, -OC (O) -, -CF 2 O-、-OCF 2 -、-CH 2 O or-OCH 2 -substitution;
R 2 is H, F, cl, br, I, CN, SCN, NCS, CF 3 Or SF 5 Or is C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 Alkynyloxy, and C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 The terminal group of the alkynyloxy group can be substituted by H, CN or CF 3 Substituted, and/or C 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 Alkynyloxy having at least one CH 2 The radicals being able to be substituted by-O-, -S-, -SO 2 -、-CO-、-C(O)O-、-OC(O)-、-OC(O)O-、-CF 2 O-、-OCF 2 -、-CH 2 CH 2 -、-CF 2 CF 2 -、-CF 2 CH 2 -、-CH 2 CF 2 -、-CHF-CHF-、-CH 2 O、-OCH 2 -, -CF = CH-, -CH = CF-, -CF = CF-, -CH = CH-or-C ≡ C-substitution, and/or C ≡ C-substitution 1-15 Alkyl radical, C 1-15 Alkoxy radical, C 2-15 Alkenyl radical, C 2-15 Alkenyloxy radical, C 2-15 Alkynyl or C 2-15 At least one H of the alkynyloxy groups can be substituted by F, cl, br or I.
7. The liquid crystal composition of claim 6, wherein IB is selected from the following structures:
The IE is selected from the following structural formulas:
The IH is selected from the following structural formula:
The IN is selected from the following structural formulas:
said IQ is selected from the following structural formulas:
The IT is selected from the following structural formulas:
8. The liquid crystal composition of claim 1, further comprising at least one or more compounds having formula II and/or at least one or more compounds having formula III:
R 3 -R'-R 4 in the formula II, the compound is shown in the specification,
wherein R is 3 、R 4 Each independently is C 1-10 Alkyl radical, C 1-10 Alkoxy radical, C 2-10 Alkenyl radical, C 2-10 Alkenyloxy radical, C 2-10 Alkynyl or C 2-10 Alkynyloxy, and R 3 、R 4 Wherein at least one H atom can be substituted by F, cl, br or I;
r' is:
R 5 -R"-R 6
in the formula (III), the compound is shown in the formula,
wherein R is 5 、R 6 Each independently is C 1-10 Alkyl radical, C 1-10 Alkoxy radical, C 2-10 Alkenyl radical, C 2-10 Alkenyloxy radical, C 2-10 Alkynyl or C 2-10 Alkynyloxy, and R 5 、R 6 Wherein at least one H atom can be substituted by F, cl, br or I;
r' is:
9. the liquid crystal composition according to claim 8, wherein the mass percentage of the compound having the formula I is 1-50%, the mass ratio of the compound having the formula II is 1-90%, and the mass percentage of the compound having the formula III is 1-90%.
10. The liquid crystal composition according to claim 9, wherein the mass percentage of the compound having the formula I is 1-25%, the mass ratio of the compound having the formula II is 10-70%, and the mass percentage of the compound having the formula III is 10-70%.
11. A liquid crystal medium comprising the liquid crystal composition according to any one of claims 1 to 10.
12. An electro-optical display element comprising a liquid crystal layer made of a liquid crystal medium according to claim 11.
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Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1942461A (en) * | 2004-04-14 | 2007-04-04 | 默克专利股份有限公司 | Dibenzofuran-, dibenzothiophene- and fluorene derivatives |
| US20150299161A1 (en) * | 2014-04-22 | 2015-10-22 | Merck Patent Gmbh | 4,6-difluorodibenzothiophene derivatives |
| CN113508168A (en) * | 2018-12-19 | 2021-10-15 | 默克专利股份有限公司 | Compound, liquid crystal medium and liquid crystal display comprising same |
| CN113698942A (en) * | 2020-05-22 | 2021-11-26 | 江苏和成显示科技有限公司 | Liquid crystal compound with negative dielectric anisotropy, liquid crystal composition and display device thereof |
| CN113845920A (en) * | 2020-06-28 | 2021-12-28 | 江苏和成显示科技有限公司 | Liquid crystal composition containing dibenzo derivative and liquid crystal display device |
| CN113845922A (en) * | 2020-06-28 | 2021-12-28 | 江苏和成显示科技有限公司 | Liquid crystal composition containing dibenzo derivative and liquid crystal display device |
| CN113845921A (en) * | 2020-06-28 | 2021-12-28 | 江苏和成显示科技有限公司 | Liquid crystal composition containing dibenzo derivative and liquid crystal display device thereof |
| WO2022084168A1 (en) * | 2020-10-19 | 2022-04-28 | Merck Patent Gmbh | 4,6-difluorodibenzothiophene derivatives and liquid-crystal medium containing these |
-
2022
- 2022-08-04 CN CN202210935726.9A patent/CN115612501A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1942461A (en) * | 2004-04-14 | 2007-04-04 | 默克专利股份有限公司 | Dibenzofuran-, dibenzothiophene- and fluorene derivatives |
| US20150299161A1 (en) * | 2014-04-22 | 2015-10-22 | Merck Patent Gmbh | 4,6-difluorodibenzothiophene derivatives |
| CN113508168A (en) * | 2018-12-19 | 2021-10-15 | 默克专利股份有限公司 | Compound, liquid crystal medium and liquid crystal display comprising same |
| CN113698942A (en) * | 2020-05-22 | 2021-11-26 | 江苏和成显示科技有限公司 | Liquid crystal compound with negative dielectric anisotropy, liquid crystal composition and display device thereof |
| CN113845920A (en) * | 2020-06-28 | 2021-12-28 | 江苏和成显示科技有限公司 | Liquid crystal composition containing dibenzo derivative and liquid crystal display device |
| CN113845922A (en) * | 2020-06-28 | 2021-12-28 | 江苏和成显示科技有限公司 | Liquid crystal composition containing dibenzo derivative and liquid crystal display device |
| CN113845921A (en) * | 2020-06-28 | 2021-12-28 | 江苏和成显示科技有限公司 | Liquid crystal composition containing dibenzo derivative and liquid crystal display device thereof |
| WO2022084168A1 (en) * | 2020-10-19 | 2022-04-28 | Merck Patent Gmbh | 4,6-difluorodibenzothiophene derivatives and liquid-crystal medium containing these |
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