CN115925663A - Organic compound, liquid crystal composition and liquid crystal display panel - Google Patents
Organic compound, liquid crystal composition and liquid crystal display panel Download PDFInfo
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- CN115925663A CN115925663A CN202211551755.1A CN202211551755A CN115925663A CN 115925663 A CN115925663 A CN 115925663A CN 202211551755 A CN202211551755 A CN 202211551755A CN 115925663 A CN115925663 A CN 115925663A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 122
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 55
- 239000000203 mixture Substances 0.000 title claims abstract description 54
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 127
- 150000001875 compounds Chemical class 0.000 claims description 111
- -1 alkenyl ether Chemical compound 0.000 claims description 64
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 239000000758 substrate Substances 0.000 claims description 34
- 125000000304 alkynyl group Chemical group 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 30
- 125000005842 heteroatom Chemical group 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 150000005215 alkyl ethers Chemical class 0.000 claims description 6
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- HAQZDUWRNKKMQY-UHFFFAOYSA-N ac1lapjb Chemical group F[S](F)(F)(F)F HAQZDUWRNKKMQY-UHFFFAOYSA-N 0.000 claims description 3
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 3
- 125000003172 aldehyde group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 9
- 229910052731 fluorine Inorganic materials 0.000 abstract description 7
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 6
- 239000000126 substance Substances 0.000 description 34
- 125000001424 substituent group Chemical group 0.000 description 17
- 150000001721 carbon Chemical group 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 125000006413 ring segment Chemical group 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 239000012769 display material Substances 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 150000002367 halogens Chemical class 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
- 230000010287 polarization Effects 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([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
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011978 dissolution method Methods 0.000 description 1
- 230000000694 effects Effects 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
- 125000005067 haloformyl group Chemical group 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
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 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
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 description 1
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 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
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 238000002834 transmittance 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
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Abstract
The present application relates to an organic compound, a liquid crystal composition, and a liquid crystal display panel. The structural formula of the organic compound contains a tetrafluoroindene derivative group, and contains a parallel-ring structure formed by connecting a five-membered ring and a benzene ring in parallel, wherein a hydrogen atom in the parallel-ring structure is replaced by a fluorine atom, and a fluorine atom substituent is only positioned on one side of the parallel-ring structure, so that stronger polarity is provided for the organic compound. When the organic compound is used as a liquid crystal material of a liquid crystal display, the organic compound has characteristics such as larger polarity and faster response time, and can improve characteristics such as contrast and/or response time of the liquid crystal display.
Description
Technical Field
The present invention relates to the technical field of liquid crystal compound materials, and in particular, to an organic compound, a liquid crystal composition, and a liquid crystal display panel.
Background
In the display field, liquid crystal displays are widely used, for example, mobile phone screens, television screens, computer screens, etc. The light emitting function of the liquid crystal display is mainly achieved by the deflection of liquid crystal molecules. Since liquid crystal molecules have photoelectric properties such as optical anisotropy, a specific arrangement is formed in an electric field, which causes a change in the polarization direction of incident light, resulting in a difference in luminance of emitted light, and the emitted light can generate a Color image that can be observed by human eyes after passing through a Color Filter (CF).
The optical, electrical and mechanical properties of the liquid crystal molecules depend on the structures of the liquid crystal molecules themselves and the side chain groups. The molecular structure of the liquid crystal molecules directly determines the speed of the light reaction, the light polarization direction, the light transmittance and the like, and further influences the display performance. Therefore, it is necessary to improve the structure and/or substituent groups of the existing liquid crystal molecules in order to optimize the electro-optical characteristics of the liquid crystal molecules and thus obtain better display effects.
Disclosure of Invention
An object of some embodiments of the present application is to provide an organic compound, a liquid crystal composition, and a liquid crystal display panel. The organic compound has the characteristics of shorter response time and/or larger-angle deflection and the like when being used as liquid crystal molecules, can be used for preparing a liquid crystal display with faster response and/or higher contrast, and overcomes the defects of long response time and the like of the existing liquid crystal molecules.
In order to solve the above-mentioned drawbacks, some embodiments of the present application provide the following technical solutions:
some embodiments of the present application provide an organic compound having a structural formula shown in formula i:
wherein:
R 1 、R 2 、R 3 、R 4 、R 5 each occurrence may be independently selected from a hydrogen atom, or a halogen group, or a cyano group, or a thiocyano group, or an isothiocyanato group, or a sulfur pentafluoride group, or a trifluoromethyl group, or an alkyl group having 1 to 15 carbon atoms, or an alkenyl group having 2-15 carbon atoms, or an alkynyl group having 2-15 carbon atoms.
Z is selected from carbon-carbon single bond, -O-, -S-, -SO 2 -、-CO-、-COO-、-OCO-、-OCOO-、-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-, -C ≡ C-, or an alkyl group having 1 to 7 carbon atoms, or an alkyl ether having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms, or an alkenyl ether having 2 to 7 carbon atoms, or an alkynyl group having 2 to 7 carbon atoms, or an alkynyl ether having 2 to 7 carbon atoms.
n is selected from 0, 1,2, or 3, in particular from 1,2, or 3. When n is 1, the compound is a compound of formula (I),
is selected from->
Each ≥ when n is greater than or equal to 2>
Are each independently selected from->
In some embodiments, when R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from alkyl having 1 to 15 carbon atoms, alkenyl having 2 to 15 carbon atoms, or alkynyl having 2 to 15 carbon atoms 1 、R 2 、R 3 、R 4 、R 5 Is monosubstituted by a cyano, trifluoromethyl or aldehyde group, or R 1 、R 2 、R 3 、R 4 、R 5 One or more hydrogen atoms of (a) are substituted with a halogen group.
In some embodiments, when R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from alkyl having 1 to 15 carbon atoms, or alkenyl having 2 to 15 carbon atoms, or alkynyl having 2 to 15 carbon atoms 1 、R 2 、R 3 、R 4 、R 5 One or more CH in 2 The groups are independently substituted with heteroatoms or heterogroups, which are not directly bonded to each other.
The above-mentioned hetero atom may be selected from an oxygen atom or a sulfur atom. The above-mentioned hetero group may be selected from-SO 2 -、-CO-、-COO-、-OCO-、-OCOO-、-CF 2 O-、-OCF 2 -、-CH 2 -CH 2 -、-CF 2 -CF 2 -、-CF 2 -CH 2 -、-CH 2 -CF 2 -、-CHF-CHF-、-OCH 2 -, -CF = CH-, -CH = CF-, -CF = CF-, -CH = CH-, or-C ≡ C-.
In some embodiments, when Z is selected from an alkyl group having 1 to 7 carbon atoms, or an alkyl ether having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms, or an alkenyl ether having 2 to 7 carbon atoms, or an alkynyl group having 2 to 7 carbon atoms, or an alkynyl ether having 2 to 7 carbon atoms, one or more CH in Z is 2 The radicals are substituted by heteroatoms or heterogroups which are not bonded directly to one another, or one or more hydrogen atoms in Z are substituted by halogen radicals.
In some embodiments of the present invention, the,
one or more hydrogen atoms of (a) are replaced by a halogen group.
In some embodiments, when
Is selected from->
When, is greater or less>
One or more non-adjacent-CH in 2 -is independently substituted by-N-.
In some embodiments, when
Is selected from->
When, is greater or less>
Is independently substituted with-N = independently.
In some embodiments, when R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from a hydrogen atom or a halogen group, R 1 、R 2 、R 3 、R 4 、R 5 Not simultaneously hydrogen atoms.
In some embodiments, R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from alkyl having 1 to 7 carbon atoms, or alkenyl having 2 to 7 carbon atoms, or alkynyl having 2 to 7 carbon atoms, R 1 、R 2 、R 3 、R 4 、R 5 One CH in 2 Radicals or two non-adjacent CH 2 The radicals being independently substituted by-O-, -CO-, -COO-, -OCO-, -CF 2 O-、-OCF 2 -、-CH 2 O-or OCH 2 -substitution.
In some embodiments, the structural formula of the organic compound is selected from any one of the following structural formulae:
A R selected from alkyl groups having 1 to 15 carbon atoms, or alkenyl groups having 2-15 carbon atoms, or alkynyl groups having 2-15 carbon atoms.
Some embodiments of the present application also provide a liquid crystal composition comprising: any one of the organic compounds and the first compound in the above embodiments.
Wherein the first compound is selected from one or more compounds with structural formulas of II-1 to II-9:
R 6 and R 7 Each independently selected from an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms, or an alkynyloxy group having 2 to 10 carbon atoms.
The liquid crystal composition provided by the embodiment of the application comprises: an organic compound, a first compound, and a second compound.
Wherein the second compound is selected from one or more compounds with structural formulas of III-1 to III-5:
R 8 and R 9 Each independently selected from an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 2 to 10 carbon atomsAlkynyl, or alkynyloxy having 2 to 10 carbon atoms.
The liquid crystal composition in each embodiment of the application comprises the following components in parts by weight:
1-35 wt% of organic compound;
1wt% -75wt% of the first compound; and
1wt% -50wt% of the second compound.
Embodiments of the present application also provide a liquid crystal display panel, which includes: the liquid crystal display device comprises a first substrate, a second substrate and a liquid crystal layer. The liquid crystal layer is located between the first substrate and the second substrate, and the liquid crystal layer contains any one of the organic compounds in the above embodiments, or contains the liquid crystal composition in any one of the above embodiments. The first substrate is an array substrate or a color film substrate, and the second substrate is a color film substrate or an array substrate. The first substrate and the second substrate have different functions.
Some embodiments of the invention have the following beneficial effects:
some embodiments of the present invention provide an organic compound. The structural formula of the organic compound contains a tetrafluoindene derivative group. The indene tetrafluoride derivative group contains a parallel-ring structure formed by connecting a five-membered ring and a benzene ring in parallel, and a hydrogen atom in the parallel-ring structure is substituted by a fluorine atom, but a fluorine atom substituent group is only positioned on one side of the parallel-ring structure, so that stronger polarity is provided for an organic compound. The experimental result proves that when the organic compound is used as a liquid crystal material of a liquid crystal display, the organic compound has the characteristics of larger polarity, quicker response time and the like, and can improve the characteristics of contrast ratio, response time and the like of the liquid crystal display.
Tetrafluoro indene
Drawings
Fig. 1 is a schematic view of a liquid crystal display device shown in an embodiment of the present invention.
Wherein the drawings are numbered as: the liquid crystal display panel comprises a backlight source 1, a lower polarizer 2, an array substrate 3, a liquid crystal layer 4, a color film substrate 5 and an upper polarizer 6.
Detailed Description
The present application is further described below with reference to specific examples and the accompanying drawings. This application may be embodied in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used herein in the description of the present application is for the purpose of describing particular embodiments only and is not intended to be limiting of the application. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
In the present application, "substituted" means that a hydrogen atom in a substituent is substituted by a substituent. "substituted or unsubstituted" means that the defined group may or may not be substituted. When a defined group is substituted, it is understood to be optionally substituted with art-acceptable groups including, but not limited to: c 1-30 An alkyl group, a heterocyclic group having 3 to 20 ring atoms, an aryl group having 5 to 20 ring atoms, a heteroaryl group having 5 to 20 ring atoms, a silane group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a haloformyl group, a formyl group, a cyano group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, a nitro group or a halogen, and the above groups may be further substituted with a substituent acceptable in the art;
in the present application, the same plurality of occurrences of a substituent may be independently selected from different groups. As shown in the general formula, the compound contains a plurality of R 1 Then R is 1 Can be independently selected from different groups. For example
6R on the benzene ring 1 May be the same as or different from each other.
In the present application, "alkyl" may mean a linear, branched and/or cyclic alkyl group. The number of carbons in the alkyl group may be any positive integer from 1 to 50, or any positive integer from 2 to 30, or any positive integer from 3 to 20, or any positive integer from 4 to 10, or any positive integer from 5 to 9, or any positive integer from 6 to 8. <xnotran> , , , , , , , ,2- ,3,3- , , , , , , 1- ,3- ,2- , 4- -2- , , 1- ,2- ,2- , , 4- , 4- , , 1- ,2,2- ,2- ,2- , , ,2- ,2- ,2- ,3,7- , , , , ,2- ,2- ,2- ,2- , , ,2- ,2- ,2- ,2- , , , , ,2- ,2- ,2- ,2- , , , , ,2- ,2- ,2- ,2- , </xnotran> N-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc. Other alkyl-containing groups, such as alkoxy, are likewise possible.
The technical scheme of the application is explained in detail as follows:
an organic compound containing an indene tetrafluoride derivative group is provided. The structural formula of the organic compound is shown as a formula I:
wherein:
R 1 、R 2 、R 3 、R 4 、R 5 each occurrence is independently selected from a hydrogen atom (-H), or a halogen group (-F, -Cl, -Br or-I), or a cyano group (-CN), or a thiocyano group (-SCN), or an isothiocyanato group (-NCS), or a sulfur pentafluoride group (-SF) 5 ) Or trifluoromethyl (-CF) 3 ) Or an alkyl group having 1 to 15 carbon atoms, or an alkenyl group having 2 to 15 carbon atoms, or an alkynyl group having 2 to 15 carbon atoms. The alkyl group having 1 to 15 carbon atoms includes a straight chain alkyl group or a branched chain alkyl group, but does not include a cycloalkyl group. In some embodiments, if to ensure greater polarity, R 3 、R 4 May also be-F, and R 2 、R 5 Then F is not present, but substituents that are less electronegative than F, or substituents that do not have electronegativity, may be selected.
Z is independently selected from carbon-carbon single bond, -O-, -S-, -SO 2 -、-CO-、-COO-、-OCO-、-OCOO-、-CF 2 O-、-OCF 2 -、-CH 2 -CH 2 -、-CF 2 -CF 2 -、-CF 2 -CH 2 -、-CH 2 -CF 2 -、-CHF-CHF-、OCH 2 -, -CF = CH-, -CH = CF-, -CF = CF-, -CH = CH-, -C ≡ C-, or an alkyl group having 1 to 7 carbon atoms, or an alkyl ether having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms, or an alkenyl ether having 2 to 7 carbon atoms, or an alkynyl group having 2 to 7 carbon atoms, or an alkynyl ether having 2 to 7 carbon atoms. 1 to 7 carbon atoms means that the number of carbon atoms takes any integer between 1 and 7, and is, for example, 1,2,3,4,5,6, 7.2 to 7 carbon atoms are likewise understood, for example 2,3,4,5,6, 7. The rest of this document is understood as such.
n is selected from any one of 0, 1,2 and 3, and preferably n is not 0. When n is 1, the compound is a compound of formula (I),
is selected from->
Each ≥ when n is greater than or equal to 2>
Are each independently selected from>
I.e. each ≥ when n is greater than or equal to 2>
May be the same or different. Two adjacent are->
They may be connected by carbon-carbon single bonds or directly through a ring atom. In the above groups, the positions not shown in the line connecting the substituents (e.g., F) represent the attachment by a hydrogen atom. Wherein one or more hydrogen atoms may be mono-or polysubstituted by a substituent. The substituent may be any halogen group.
In some embodiments of the present application, when R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from alkyl having 1 to 15 carbon atoms, alkenyl having 2 to 15 carbon atoms, or alkynyl having 2 to 15 carbon atoms 1 、R 2 、R 3 、R 4 、R 5 The hydrogen atom (-H) of the terminal group of (1) is substituted by cyano (-CN), trifluoromethyl (-CF) 3 ) Or mono-substituted with an aldehyde (-CHO). In other embodiments, R 1 、R 2 、R 3 、R 4 、R 5 One or more hydrogen atoms (-H) in (a) are substituted with any one of the halogen groups (-F, -Cl, -Br, or-I). The terminal groups are substituted to provide a certain polarity to the liquid crystal molecules.
In some embodiments of the present application, when R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from alkyl groups having 1 to 15 carbon atoms, or 2-15Alkenyl of carbon atoms, or alkynyl of 2-15 carbon atoms, R 1 、R 2 、R 3 、R 4 、R 5 One or more non-adjacent CH(s) in (2) 2 The groups are independently substituted with heteroatoms or heterogroups, which are not directly bonded to each other. That is, the heteroatoms are not directly bonded to each other, or the hetero groups are not directly bonded to each other, or the heteroatoms and hetero groups are not directly bonded to each other.
In some embodiments herein, the heteroatom is selected from an oxygen atom (-O-) or a sulfur atom (-S-).
In some embodiments of the present application, the heterogroups are selected from-SO 2 -, -CO-, - -COO- (also known as-C (O) O-), -OCO- (also known as-OC (O) -), -CF 2 O-、-OCF 2 -、-CH 2 O-, or-OCH 2 -。-SO 2 -is a sulfone group, and both O' S are each connected to S via a double bond. -CO-represents a carbonyl group, the O atom being linked to C by a double bond. For groups containing two O atoms, the attachment of the O atoms is as follows. -C (O) O-contains a carbonyl group (C = O), O inside the brackets indicating that O is linked to a carbon atom by a double bond, O outside the brackets indicating that O is linked to a carbon atom by a single bond. O inside the parentheses of-OC (O) -means that O is bonded to the carbon atom through the double bond, and O outside the parentheses means that O is bonded to the carbon atom through the single bond. The remaining groups being of the same general structure, e.g. -CH 2 O in O-represents that the O atom is bonded to the C atom by a single bond. The manner of attachment of the groups in the examples of the present application follows the general principles of organic chemistry.
In some embodiments herein, when Z is selected from an alkyl group having 1 to 7 carbon atoms, or an alkyl ether having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms, or an alkenyl ether having 2 to 7 carbon atoms, or an alkynyl group having 2 to 7 carbon atoms, or an alkynyl ether having 2 to 7 carbon atoms, one or more CH in Z is 2 The groups are substituted with heteroatoms or heterogroups which are not directly bonded to each other, or one or more hydrogen atoms (-H) in Z are substituted with any one of the halogen groups (-F, -Cl, -Br, or-I). The substitution may be mono-or polysubstituted. Definition of hetero atoms or hetero groupsAs above.
In some embodiments of the present application, one
(number is only one) or each>
(when the number is plural) one or more hydrogen atoms in the group is substituted with any one halogen group (-F, -Cl, -Br, or-I).
In some embodiments of the present application, when one is
(number is only one) or each>
(in the case of a plurality of numbers) are each independently selected from->
When, is greater or less>
One or more non-adjacent-CH in 2 -is independently each occurrence-substituted with-N-. adjacent-CH 2 Cannot be simultaneously substituted by-N-.
In some embodiments of the present application, when one is used
(number is only one) or each>
(in the case of a plurality of numbers) are each independently selected from->
When, is greater or less>
Is independently replaced by-N = each. adjacent-CH = cannot be simultaneously substituted by-N-.
In some embodiments of the present application, when R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from a hydrogen atom (-H) or a halogen group (e.g., -F) (-), R 1 、R 2 、R 3 、R 4 、R 5 Not simultaneously hydrogen atoms. The halogen group may be preferably selected from-F because-F is strongly electronegative and can provide stronger polarity to the liquid crystal molecule as a side chain group.
In some embodiments of the present application, R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from alkyl having 1 to 7 carbon atoms, or alkenyl having 2 to 7 carbon atoms, or alkynyl having 2 to 7 carbon atoms, R 1 、R 2 、R 3 、R 4 、R 5 One CH in 2 Radicals or two non-adjacent CH 2 The radicals being independently selected from the group consisting of-O-, -CO-) -COO-, -OCO-, -CF 2 O-、-OCF 2 -、-CH 2 O- (may refer to-CH) 2 -O-), or-OCH 2 - (denoting-O-CH) 2 -) is substituted. The substituents, however, not being directly linked to one another, may be spaced apart from one another, e.g. by CH between two substituents 2 The groups are spaced apart. Alkyl includes straight chain or branched alkyl, but does not include cycloalkyl. In other embodiments, R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from alkyl having 2 to 6 carbon atoms, or alkenyl having 3 to 6 carbon atoms, or alkynyl having 3 to 6 carbon atoms, or CF 3 。
In some embodiments of the present application, R 1 、R 2 、R 3 、R 4 、R 5 Independently of one another, represent H or F and are not simultaneously H. Since H is less polar than F, the side chain group needs to have at least one F to provide a certain polarity to the liquid crystal molecules.
If R in formula I 1 、R 2 、R 3 、R 4 、R 5 Each independently of the other represents an alkyl group, which may be a linear alkyl group or a branched alkyl group. 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.
Furthermore, R in the formula I 1 、R 2 、R 3 、R 4 、R 5 Each independently of the other, represents an alkenyl or alkynyl group having 2 to 15 carbon atoms, which may be linear or branched and has 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. In particular, it may be preferable that 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-alkynyl, but-2-alkynyl, but-3-alkynyl, pent-1-ynyl, pent-2-ynyl, pent-3-ynyl, pent-4-ynyl, hex-1-ynyl, hex-2-ynyl, hex-3-ynyl, hex-4-ynyl, hex-5-ynyl, hex-1-heptynyl, hept-2-ynyl, hex-4-hept-ynyl, Z-6-heptynyl and Z-hept-yl may be isomers. Of alkenyl and alkynyl, 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.
Halogen herein denotes F, cl, br or I, especially F or Cl.
In the present invention, the term "alkyl", "alkenyl" or "alkynyl" may denote a straight 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.
In some embodiments of the present application, the structural formula of the organic compound is selected from any one of the following structural formulas:
wherein A is R Can refer to R 1 Of the kind, e.g. A R May be selected from alkyl groups having 1 to 15 carbon atoms, or alkenyl groups having 2 to 15 carbon atoms, or alkynyl groups having 2 to 15 carbon atoms.
The indene tetrafluoride derivative group is a parallel ring structure formed by connecting a five-membered ring and a benzene ring in parallel, wherein the F substituent is only positioned on one side of the parallel ring structure, so that the parallel ring structure is endowed with larger polarity. The positions of the fused ring structure not substituted by F may be substituted by a substituent R 2 、R 3 、R 4 、R 5 And (4) substitution.
In some embodiments herein, the structural formula of the organic compound is selected from any one of the following structural formulas:
the substances can be used as liquid crystal media in liquid crystal layers of liquid crystal displays.
It should be noted that: IA is not in the higher structural formulae IA1 to IA7, the same applies to the rest of the same. For example, IB is not a generic structural formula for IB1 to IB7, and IC is not a generic structural formula for IC1 to IC7, etc.
The group or substituent of formula I in the liquid crystal composition of the present application, or the formula I in the liquid crystal composition of the present application itself, may be in the form of an optically active or stereoisomeric group, substituent or compound, which has an asymmetric center or a chiral center, and these are also included in the present application. The compounds of the general formula I according to the present application 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.
The present application provides a liquid crystal composition comprising: the organic compound and the first compound.
Wherein the first compound is selected from one or more compounds with structural formulas of II-1 to II-9:
wherein the terminal group R 6 And R 7 Each independently selected from an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms, or an alkynyloxy group having 2 to 10 carbon atoms. Alkyl includes straight chain or branched alkyl, but does not include cycloalkyl. In some embodiments, R 6 And R 7 The H atom in (A) may be mono-or polysubstituted by F, cl, br, I. Or, R 6 And R 7 Is independently substituted with-F, -Cl, -Br or-I. The number of carbon atoms of 1 to 10 is an integer of 1,2,3,4,5,6,7,8,9 or 10.
The present application provides a liquid crystal composition comprising: the organic compound, the first compound, and the second compound described above.
Wherein the second compound is selected from one or more compounds having the structural formula III-1 to III-5:
wherein the terminal group R 8 And R 9 Each independently selected from an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms, or an alkynyloxy group having 2 to 10 carbon atoms. Alkyl groups may be straight chain alkyl or branched chain alkyl groups, but are not cycloalkyl groups. In some embodiments, R 8 And R 9 The H atom in (A) can be mono-or polysubstituted by F, cl, br, I. Or, R 8 And R 9 Wherein one or more hydrogen atoms are independently substituted with-F, -Cl, -Br, or-I.
In the above formula of the second compound, one or more hydrogen atoms are independently substituted by-F, -Cl, -Br, or-I. Thus, the second compound may also have the following structural formula:
in some embodiments of the present application, there is provided a liquid crystal composition comprising:
1-35 wt% of organic compound;
1wt% -75wt% of the first compound; and
1wt% -50wt% of the second compound.
The weight ratio of the organic compound to the first compound to the second compound is 100wt%.
Wherein the organic compound may include any one of the following ranges: 2 to 30wt%, 3 to 28wt%, 5 to 25wt%, etc., but is not limited to this range. The first compound may include any one of the following ranges: 5wt% to 70wt%, 15wt% to 50wt%, 20wt% to 45wt%, etc., but is not limited to this range. The second compound may include any one of the following ranges: 5 to 45wt%, 15 to 40wt%, 25 to 30wt%, but is not limited to this range.
In other embodiments of the present application, the liquid crystal composition comprises:
1wt% -25wt% of organic compound;
45wt% -75wt% of the first compound; and
10wt% -40wt% of the second compound.
In other embodiments of the present application, the liquid crystal composition comprises:
1wt% -15wt% of organic compound;
50wt% -70wt% of the first compound; and
15wt% -30wt% of the second compound.
The liquid crystal composition is used in a liquid crystal layer of a liquid crystal display panel, and the sum of the weight parts of the organic compound, the first compound and the second compound is 100wt%. The same or similar features in the respective embodiments of the present application may be arbitrarily combined without inventive labor, for example, any one of the values of 1wt% to 35wt% of the organic compound may be arbitrarily combined with any one of the values of 45wt% to 75wt% of the first compound and 1wt% to 50wt% of the second compound, as long as the sum of the parts by weight of the respective components is 100wt%.
In other embodiments of the present application, the liquid crystal composition comprises:
(1) 1-20% of a compound represented by formula IA; formula IA may be selected from any specific substance in the structural formulas IA1 to IA7, but is not limited to these structural formulas;
(2) 0-10% of a compound represented by formula IB; formula IB can be selected from any specific material in the structural formulas of IB1 to IB7, but is not limited to these structural formulas;
(3) 0-10% of a compound represented by formula IC; the formula IC may be selected from any specific substance in the structural formulas of IC1 to IC7, but is not limited to these structural formulas;
(4) 0-10% of a compound represented by formula ID; the formula ID can be selected from any specific substance in the structural formulas from ID1 to ID7, but is not limited to the structural formulas;
(5) 0-10% of a compound represented by formula IE; the formula IE can be selected from any specific substance in the structural formulas of IE1 to IE7, but is not limited to the structural formulas;
(6) 0-10% of a compound represented by formula IF; the formula IF can be selected from any specific substance in the structural formulas from IF1 to IF7, but is not limited to the structural formulas;
(7) 0-10% of a compound represented by formula IG; formula IG may be selected from any specific substance in the formulae IG1 to IG7, but is not limited to these formulae;
(8) 0-10% of a compound represented by formula IH; the formula IH may be selected from any specific substance in the structural formulas of IH1 to IH7, but is not limited to these structural formulas;
(9) 0-10% of a compound represented by formula II; the formula II may be selected from any specific substance in the structural formulas II1 to II7, but is not limited to these structural formulas;
(10) 0-10% of a compound represented by formula IJ; the formula IJ may be selected from any specific substance in the structural formulas IJ1 to IJ7, but is not limited to these structural formulas;
(11) 0-10% of a compound represented by formula IK; the formula IK may be selected from any specific substance in the structural formulae of IK1 to IK7, but is not limited to these structural formulae;
(12) 0-10% of a compound represented by formula IL; the formula IL may be selected from any specific substance in the structural formulas of IL1 to IL7, but is not limited to these structural formulas;
(13) 45-70% of a compound represented by any one of formula II-1 to formula II-9 (i.e., the first compound);
(14) 10-40% of a compound represented by any one of formulae III-1 to III-5 (i.e., the second compound).
Wherein, the components (1) to (12) belong to organic compounds, and the structural formula follows the structural formula shown in formula I. The sum of the weight percentages of the components is 100wt%. In the above numerical range, 0 to 10% means that the minimum value of the above compounds may be 0%, the maximum value may be 10%, or any one of 0 to 10%, but it is necessary to ensure that the sum of the weight percentages of the above components is 100wt%. For example, the endpoints of a range of values can be 0.5%, 1%, 1.5%, 2%, 3.2%, 4.1%, 5%, 7%, 8%, 9%, or 9.5%, and the like.
Optionally, the liquid crystal composition comprises:
(1) 1-15% of a compound represented by formula IA; formula IA may be selected from any specific substance in the structural formulas IA1 to IA7, but is not limited to these structural formulas;
(2) 0-5% of a compound represented by formula IB; formula IB may be selected from any one of the specific structural formulas of IB1 to IB7, but is not limited to these structural formulas;
(3) 0-5% of a compound represented by formula IC; the formula IC may be selected from any specific substance in the structural formulas of IC1 to IC7, but is not limited to these structural formulas;
(4) 0-5% of a compound represented by formula ID; the formula ID can be selected from any specific substance in the structural formulas from ID1 to ID7, but is not limited to the structural formulas;
(5) 0-5% of a compound represented by formula IE; the formula IE can be selected from any specific substance in the structural formulas of IE1 to IE7, but is not limited to the structural formulas;
(6) 0-5% of a compound represented by formula IF; the formula IF can be selected from any specific substance in the structural formulas from IF1 to IF7, but is not limited to the structural formulas;
(7) 0-5% of a compound represented by formula IG; the formula IG can be selected from any specific substance in the structural formulas of IG1 to IG7, but is not limited to these structural formulas;
(8) 0-5% of a compound represented by formula IH; the formula IH may be selected from any specific substance in the structural formulas of IH1 to IH7, but is not limited to these structural formulas;
(9) 0-5% of a compound represented by formula II; the formula IH may be selected from any one specific substance in the structural formulae II1 to II7, but is not limited to these structural formulae;
(10) 0-5% of a compound represented by formula IJ; the formula IJ may be selected from any specific substance in the structural formulas IJ1 to IJ7, but is not limited to these structural formulas;
(11) 0-5% of a compound represented by formula IK; the formula IK may be selected from any specific substance in the structural formulae of IK1 to IK7, but is not limited to these structural formulae;
(12) 0-5% of a compound represented by formula IL; the formula IL may be selected from any specific substance in the structural formulas of IL1 to IL7, but is not limited to these structural formulas;
(13) 45-70% of a compound represented by any one of formula II-1 to formula II-9 (i.e., the first compound);
(14) 10-35% of a compound represented by any one of formula III-1 to formula III-5 (i.e., the second compound). The sum of the weight percentages of the components is only required to be 100wt%.
Optionally, the liquid crystal composition comprises:
(1) 3-13% of a compound represented by formula IA; formula IA may be selected from any specific substance in the structural formulas IA1 to IA7, but is not limited to these structural formulas;
(2) 0-5% of a compound represented by formula IB; formula IB can be selected from any specific material in the structural formulas of IB1 to IB7, but is not limited to these structural formulas;
(3) 0-5% of a compound represented by formula IC; the formula IC may be selected from any specific substance in the structural formulas of IC1 to IC7, but is not limited to these structural formulas;
(4) 0-5% of a compound represented by formula ID; the formula ID can be selected from any specific substance in the structural formulas from ID1 to ID7, but is not limited to the structural formulas;
(5) 0-5% of a compound represented by formula IE; the formula IE can be selected from any specific substance in the structural formulas of IE1 to IE7, but is not limited to the structural formulas;
(6) 0-5% of a compound represented by formula IF; the formula IF can be selected from any specific substance in the structural formulas from IF1 to IF7, but is not limited to the structural formulas;
(7) 0-5% of a compound represented by formula IG; the formula IG can be selected from any specific substance in the structural formulas of IG1 to IG7, but is not limited to these structural formulas;
(8) 0-5% of a compound represented by formula IH; the formula IH may be selected from any specific substance in the structural formulas of IH1 to IH7, but is not limited to these structural formulas;
(9) 0-5% of a compound represented by formula II; the formula IH may be selected from any one of the specific substances in the structural formulae II1 to II7, but is not limited to these structural formulae;
(10) 0-5% of a compound represented by formula IJ; the formula IJ may be selected from any specific substance in the structural formulas IJ1 to IJ7, but is not limited to these structural formulas;
(11) 0-5% of a compound represented by formula IK; the formula IK may be any specific substance selected from the structural formulae of IK1 to IK7, but is not limited to these structural formulae;
(12) 0-5% of a compound represented by formula IL; the formula IL may be selected from any specific substance in the structural formulas of IL1 to IL7, but is not limited to these structural formulas;
(13) 45-70% of a compound represented by any one of formula II-1 to formula II-9 (i.e., the first compound);
(14) 15-30% of a compound represented by any one of formula III-1 to formula III-5 (i.e., a second compound). The sum of the weight percentages of the components is 100wt%.
The application of the organic compound represented by the general formula I in preparing a liquid crystal mixture, a liquid crystal composition, a liquid crystal display material or an electro-optical display element material, and the liquid crystal mixture, the liquid crystal composition, the liquid crystal display material or the electro-optical display element material containing the liquid crystal compound represented by the general formula I also belong to the protection scope of the application.
The principle of the technical solution of the present application is briefly described below. It should be noted that the following principle explanations are possible principle explanations and do not represent the only principle explanations. It is understood that the following explanation of the principles may be applied to the same or similar materials according to various factors such as the advancement of technology or academic parlance, and therefore, the following explanation of the principles does not limit the technical solutions of the present application and other reasonable explanations of the principles may exist.
As shown in the above structural formula, the organic compound in the embodiment of the present application has a parallel ring structure. The fused ring structure is formed by connecting a five-membered ring and a benzene ring in parallel. And two F atom substituents are present on the carbon atom at position 1 and one F atom substituent is present on each of the carbon atoms at positions 6 and 7 in the cyclic structure. Thus, the F substituents on the fused ring structure are all located on one side of the fused ring structure. Since the F atom has a strong electronegativity and a strong electron-withdrawing ability, and the benzene ring belongs to an electron-rich system, the electron distribution is biased to one side of the fused ring structure, which gives the organic compound a strong polarity. When the organic compound is used for the liquid crystal layer, rapid deflection of liquid crystal molecules can be achieved, thereby improving the response speed of the liquid crystal display. However, in other embodiments of the present application, R is not required to be very polar when the liquid crystal mixture is being formulated 2 And/or R 5 And may also be fluorine atoms to allow the polar moiety to cancel out.
Other components of the liquid crystal composition of the present application can be formulated by those skilled in the art according to the professional knowledge and the requirements of device parameters. The addition of the organic compounds of the present application can improve the overall performance of the liquid crystal composition. The liquid crystal composition has the characteristics of higher polarity, lower viscosity, higher transparency point, faster response and the like, has positive significance for developing a display device with fast response, and is very suitable for blending of a liquid crystal mixture or a liquid crystal composition. The liquid crystal composition In some embodiments of the present application is suitable for a display In a Vertical Alignment (VA) mode, a birefringence (ECB) mode, a Plasma Addressed Liquid Crystal (PALC) mode, a Fringe Field Switching (FFS) mode, or an In-plane switching (IPS) mode because of its properties of larger polarity, lower viscosity, higher transparency, and faster response speed.
Some embodiments of the present application also provide a liquid crystal display panel, including: the liquid crystal display device comprises a first substrate, a second substrate and a liquid crystal layer. The liquid crystal layer is positioned between the first substrate and the second substrate. The liquid crystal layer comprises the liquid crystal composition. Experiments prove that when the liquid crystal composition in the embodiment of the application is used for a liquid crystal layer, the formed liquid crystal layer has low rotational viscosity, high bright point, optical anisotropy of a use range and ideal liquid crystal equivalent properties in a wide temperature range.
The first substrate is an array substrate, and the second substrate is a color film substrate, or the first substrate is a color film substrate and the second substrate is an array substrate. But the first substrate functions differently from the second substrate.
In some embodiments of the present application, the first alignment film and/or the second alignment film are further disposed on both sides of the liquid crystal layer. The first alignment film and/or the second alignment film is used for realizing the alignment function of liquid crystal molecules. The liquid crystal molecules are given a stable pretilt angle (Pre-tilt angle). The aligned liquid crystal molecules can be deflected in an electric field according to a predetermined deflection angle, so that the direction of light can be changed according to specific needs. The material of the first alignment film and/or the second alignment film may be Polyimide (PI).
In other embodiments of the present application, an upper polarizer and a lower polarizer are further disposed on both sides of the liquid crystal layer.
As shown in fig. 1, a structure of a liquid crystal display panel provided by an embodiment of the present application may include: the liquid crystal display panel comprises a backlight source 1, a lower polarizer 2, an array substrate 3, a liquid crystal layer 4, a color film substrate 5, an upper polarizer 6 and the like. But is not limited solely to this structure and variations or modifications may be made to the structure by those skilled in the art. In addition, the liquid crystal display panel may also include other structures.
The present application will be described in conjunction with embodiments but is not limited to the following embodiments, it being understood that the appended claims are intended to cover all such modifications and changes as fall within the true spirit and scope of the application, which are intended to be covered by the claims appended hereto, as those skilled in the art should understand that within the spirit and scope of the present application as defined by the present inventive concepts. The compounds in the following examples may be numbered the same as those of the aforementioned compounds, but have different structures. That is, the numbers of the compounds in the following respective embodiments are independent of the numbers of the respective compounds described above. It is not necessary to compare whether the numbers and structures of the compounds in the following respective examples are identical to those of the aforementioned respective compounds, and descriptions of different parts need to be treated separately.
Preparation method
In various embodiments of the present application, the organic compound (e.g., a structure shown in formula I) can be synthesized by, for example, the following scheme, wherein R is 1 ，R 2 ，R 3 ，R 4 And R 5 Has the meaning of formula I:
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
The following embodiments of the present application provide a method for preparing a liquid crystal composition, which all use a thermal dissolution method, including the steps of:
1. weighing corresponding liquid crystal compounds (including organic compounds, first compounds and/or second compounds) by using a balance according to the mass percentages in the following table, wherein the weighing and adding sequence has no specific requirement, and the liquid crystal compounds are generally weighed and mixed at one time in the sequence of the melting points of the liquid crystal compounds from low to high; the total weight of the liquid crystal composition formed may be determined according to specific needs, and if the amount is large, the total weight may be a large value, for example, 15kg to 550kg. If smaller amounts are used, the total weight can be taken to smaller values for laboratory studies, for example from 1kg to 12kg.
2. Heating and stirring at 60-100 deg.C to dissolve and mix the components;
3. cooling to room temperature, and packaging to obtain a target sample, thereby obtaining the liquid crystal composition.
Unless otherwise indicated, the percentages in the present invention are weight 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 Refractive index for extraordinary rays(ii) a γ 1 represents the rotational viscosity at 25 ℃ (unit: mPas); Δ ∈ represents dielectric anisotropy at 25 ℃, ∈ is the dielectric constant perpendicular to the long axis of the liquid crystal molecule. The liquid crystal compositions of the various examples have the following composition ratios and performance parameters:
table 1 component distribution and performance parameters of the liquid crystal composition of example 1
In the formula IJ7 of the present embodiment, two adjacent
Are of different kinds, are structurally different and are directly connected through a ring atom.
Table 2 component distribution and performance parameters of the liquid crystal composition of example 2
In the formula IG7 of the present embodiment, two adjacent
Are different in kind and structure and are connected by a carbon-carbon single bond.
Table 3 component distribution and performance parameters for the liquid crystal composition of example 3
In the formulas IH1 and IF1 of the present embodiment, two adjacent formulas are
Are different in kind and structure and are connected by a carbon-carbon single bond.
Table 4 component distribution and performance parameters for the liquid crystal composition of example 4
In the formula IA1 of this example, only 1
TABLE 5 component distribution and Performance parameters for the liquid Crystal composition of example 5
In the formula IA4 of this example, only 1
In formula IJ7 of the present embodiment, two adjacent ^ s>
Are different in kind and structure and are connected by a carbon-carbon single bond.
TABLE 6 component partitioning and Performance parameters for the liquid Crystal composition of example 6
In the formulas II1 and IL1 of the present example, two adjacent ones
Are different in kind and structure and are connected by a carbon-carbon single bond.
Experiments prove that the liquid crystal composition has the characteristics of higher polarity, lower viscosity, higher transparency point, higher dielectric anisotropy (delta epsilon) and/or faster response and the like, and can be used for preparing a liquid crystal display device with high response speed and/or high contrast.
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that various changes and modifications can be made by those skilled in the art without departing from the spirit of the invention, and these changes and modifications are all within the scope of the invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (12)
1. An organic compound having a structural formula shown in formula i:
wherein:
R 1 、R 2 、R 3 、R 4 、R 5 each occurrence is independently selected from a hydrogen atom, or a halogen group, or a cyano group, or a thiocyano group, or an isothiocyanato group, or a sulfur pentafluoride group, or a trifluoromethyl group, or an alkyl group having 1 to 15 carbon atoms, or an alkenyl group having 2 to 15 carbon atoms, or an alkynyl group having 2 to 15 carbon atoms;
z is selected from carbon-carbon single bond, -O-, -S-, -SO 2 -、-CO-、-COO-、-OCO-、-OCOO-、-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-, -C ≡ C-, or alkyl having 1 to 7 carbon atoms, or alkyl ether having 1 to 7 carbon atoms, or alkenyl having 2 to 7 carbon atomsAn alkenyl ether of 7 carbon atoms, or an alkynyl group having 2 to 7 carbon atoms, or an alkynyl ether having 2 to 7 carbon atoms;
n is selected from 1,2 or 3; when n is 1, the compound is a compound of formula (I),
selected from the group consisting of>
Each ≥ when n is greater than or equal to 2>
Are each independently selected from>
2. An organic compound according to claim 1, wherein when R is 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from alkyl having 1 to 15 carbon atoms, or alkenyl having 2 to 15 carbon atoms, or alkynyl having 2 to 15 carbon atoms 1 、R 2 、R 3 、R 4 、R 5 Is monosubstituted by a cyano, trifluoromethyl or aldehyde group, or R 1 、R 2 、R 3 、R 4 、R 5 One or more hydrogen atoms of (a) are substituted with a halogen group.
3. An organic compound according to claim 1, wherein when R is 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from the group consisting of having 1 to 15 carbon atomsOr alkenyl having 2 to 15 carbon atoms, or alkynyl having 2 to 15 carbon atoms, R 1 、R 2 、R 3 、R 4 、R 5 One or more CH in 2 Independently substituted with a heteroatom or a heterogroup, said heteroatom and/or said heterogroup not being directly bonded to each other;
the heteroatom is selected from an oxygen atom or a sulfur atom;
the hetero group is selected from-CO-) -COO-, -OCO-, -CF 2 O-、-OCF 2 -、-CH 2 O-or-OCH 2 -。
4. The organic compound of claim 1, wherein when Z is selected from an alkyl group having 1 to 7 carbon atoms, or an alkyl ether having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms, or an alkenyl ether having 2 to 7 carbon atoms, or an alkynyl group having 2 to 7 carbon atoms, or an alkynyl ether having 2 to 7 carbon atoms, one or more CH in Z is 2 The group is substituted by a heteroatom or a heterogroup, said heteroatom and/or said heterogroup not being directly bonded to each other, or one or more hydrogen atoms in Z are substituted by a halogen group.
5. An organic compound according to claim 1,
one or more hydrogen atoms of (a) are substituted with a halogen group; and/or +>
When in use
Selected from the group consisting of>
When, is greater or less>
One or more non-adjacent-CH in 2 -independently is substituted by-N-; and/or
When in use
Is selected from->
When, is greater or less>
Is independently substituted with-N = independently.
6. An organic compound according to claim 1, wherein when R is 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from a hydrogen atom or a halogen group, R 1 、R 2 、R 3 、R 4 、R 5 Not being hydrogen atoms at the same time; and/or
When R is 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from alkyl having 1 to 7 carbon atoms, alkenyl having 2 to 7 carbon atoms, or alkynyl having 2 to 7 carbon atoms 1 、R 2 、R 3 、R 4 、R 5 One CH in 2 Radicals or two non-adjacent CH 2 The radicals being independently substituted by-O-, -CO-, -COO-, -OCO-, -CF 2 O-、-OCF 2 -、-CH 2 O-or-OCH 2 -substitution.
7. The organic compound according to claim 1, wherein the structural formula of the organic compound is selected from any one of the following structural formulae:
A R selected from alkyl groups having 1 to 15 carbon atoms, orAlkenyl having 2 to 15 carbon atoms, or alkynyl having 2 to 15 carbon atoms.
8. The organic compound of claim 1, wherein the structural formula of the organic compound is selected from any one of the following structural formulas:
9. a liquid crystal composition, comprising: an organic compound according to any one of claims 1 to 8; and a first compound;
the first compound is selected from one or more compounds with structural formulas II-1 to II-9:
R 6 and R 7 Each independently selected from an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms, or an alkynyloxy group having 2 to 10 carbon atoms.
10. The liquid crystal composition of claim 9, further comprising a second compound;
the second compound is selected from one or more compounds with structural formulas of III-1 to III-5:
R 8 and R 9 Each independently selected from an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms, or an alkynyloxy group having 2 to 10 carbon atoms.
11. The liquid crystal composition of claim 10, wherein the liquid crystal composition comprises:
1-35 wt% of organic compound;
1wt% -75wt% of a first compound; and
1wt% -50wt% of the second compound.
12. A liquid crystal display panel, comprising: a first substrate, a second substrate, and a liquid crystal layer between the first substrate and the second substrate, the liquid crystal layer containing the organic compound according to any one of claims 1 to 8, or containing the liquid crystal composition according to any one of claims 9 to 11.
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