CN109593040A - Polymerizable compound containing benzothiophene and the composition comprising the compound - Google Patents
Polymerizable compound containing benzothiophene and the composition comprising the compound Download PDFInfo
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- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
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- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
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- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K2019/128—Compounds containing phenylene-1,2-diyl
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Abstract
A kind of polymerizable compound is as shown in formula I:Wherein, Q is indicatedP1、P2Expression independentOrAnd liquid-crystal composition, liquid crystal display device containing I polymerizable compound of formula.
Description
Technical field
The present invention relates to field of liquid crystal display, and in particular to a kind of polymerisable liquid crystal compound containing benzothiophene and with
And the liquid-crystal composition comprising the liquid-crystal compounds, and include the display element or liquid crystal display of the liquid-crystal composition.
Background technique
Thin Film Transistor-LCD (TFT-LCD) experienced very long phase of basic research, realize mass production, quotient
After industry, the advantages that frivolous with its, environmentally friendly, high-performance, has become the main product in LCD application: either small size
Mobile phone screen or large-sized laptop (Notebook PC) or monitor (Monitor), and the liquid crystal of enlargement
TV (LCD-TV), is found everywhere the application of TFT-LCD.
The early stage TFT-LCD product of commercialization uses TN display pattern substantially, and greatest problem is narrow viewing angle.With product
The increase of size, the especially application in the field TV, the IPS display pattern with wide view angle, VA display pattern are successively
It is developed and is applied, be based especially on the improvement of VA display pattern, be taken up in order of priority and broken through in each major company
Property development, this depends primarily on wide angle of visibility, high contrast possessed by VA mode itself and without advantages such as friction matchings,
Have again and be exactly, the contrast that VA mode is shown is to the optical anisotropy (△ n) of liquid crystal, the thickness (d) and incident light of liquid crystal cell
Wavelength (λ) dependency degree it is smaller, will make this mode of VA become great prospect display technology.
But liquid crystal media used in the display element of the active array addressing mode of VA mode etc., itself is simultaneously imperfect,
Such as image retention level will be significantly worse than the display element of positive dielectric anisotropy, the response time is slow, and driving voltage is relatively high
The disadvantages of.At this point, some novel VA display technologies are quietly given birth to: as PSVA technology realizes the similar wide view of MVA/PVA
Wild angle display pattern, also simplifies CF technique, to improve aperture opening ratio while reducing CF cost, can also obtain higher
Brightness, and then obtain higher contrast.Further, since entire liquid crystal has pre-tilt angle, there is no domino delay phenomenon,
The faster response time can also be obtained under the driving voltage maintained like, image retention level will not be affected, but by
The Fine Slit dense distribution electrode in pixel, therefore if electrode width cannot be uniformly distributed, it is easy to there is display unevenness
Problem.As UVVA technology, on the basis of keeping PSVA technical advantage, due to there is no Slit structure in TFT side, there is pixel electricity
Show that improvement is also obtained in uneven problem caused by pole width is uneven.Although display device is constantly developing, people are also
Have been devoted to study new liquid-crystal compounds, obtain so that liquid crystal media and its performance applied to display device constantly to
Preceding development.
Polymerizable mesogenic unit (RMs) is currently the very popular and important project of display industry, the neck of possible application
Domain includes polymer-stabilized alignment (PSA) liquid crystal display, (PS-BP) liquid crystal display of polymer stabilizing blue phase and graphical position phase
Poor film (Pattern Retarder Film) etc..
PSA principle is just being used in different typical LC displays, for example, PSA-VA, PSA-OCB, PS-IPS/FFS and
The liquid crystal displays such as PS-TN.By taking presently the most widely applied PSA-VA display as an example, liquid can be obtained by PSA method
The pre-tilt angle of brilliant box, the pre-tilt angle have active influence to the response time.For PSA-VA display, standard can be used
MVA or PVA pixel and electrode design, but if side electrode design using special graph and do not adopted in the other end
It with the design of protrusion, can significantly simplify production, while display being made to obtain extraordinary contrast and very high light transmission
Rate.
The prior art has been found that the application aspect of LC mixture and RMs in PSA display still has the shortcomings that.It is first
It first, is not up to the present that each desired solvable RM is suitable for PSA display；Simultaneously, if it is desired to by means of UV
Light is polymerize (this may be advantageous for certain applications) without adding photoinitiator, then selection becomes smaller；In addition,
LC mixture (hereinafter also referred to as " LC body mixture ") combines " material system " to be formed with selected polymerizable components and answers
With minimum rotary viscosity and best photoelectric properties, for increasing " voltage retention " (VHR) to reach effect.In PSA-
It in terms of VA, is very important using the high VHR after the irradiation of (UV) light, otherwise will lead to final display and image retention etc. occur and ask
Topic.Up to the present, the combination of not all LC mixture and polymerizable components composition is adapted to PSA display.This
Mainly due to there is no inclination angle to occur or occur insufficient to incline after polymerizable unit is too short for UV sensibility wavelength or illumination
The homogeneity of angle or polymerizable components after illumination is poor, or because VHR is lower for TFT display application after UV
Etc. influence.
Summary of the invention
The present invention provides a kind of polymerizable compound of four polymer-based groups containing acrylic, and contains such compound
Negative liquid crystal composition, and liquid crystal display element or liquid crystal display comprising the liquid-crystal composition are particularly suitable for showing
The PSA-IPS liquid-crystal composition of the PSVA liquid-crystal composition and IPS mode of device or TV application, especially polymerizable compound
With faster polymerization speed and low-residual.
The liquid-crystal composition has lower viscosity, quick response may be implemented, while having moderate dielectric respectively to different
Property Δ ε, moderate optical anisotropy Δ n (0.09-0.11), the high stability to light and heat.Include the liquid-crystal composition
Liquid crystal display element or liquid crystal display have wider nematic temperature range, suitable or higher birefringence respectively to
The performances such as anisotropic Δ n, very high resistivity, good anti-ultraviolet property, high charge retention rate and low-steam pressure.
In order to realize above-mentioned advantageous effects, the present invention provides one kind polymerizable compounds as shown in formula I:
Wherein, Q is indicatedP1、P2It each independently represents
The present invention also provides one kind include one or more type I compounds, II compound of one or more formulas and
The liquid-crystal composition of one or more III compounds of formula,
Wherein, Q is indicatedP1、P2It each independently represents
R1、R2、R3、R4Each independently representing alkyl, fluorine-substituted carbon atom number that carbon atom number is 1-10 is 1-10's
The chain that alkoxy that alkoxy that alkyl, carbon atom number are 1-10, fluorine-substituted carbon atom number are 1-10, carbon atom number are 2-10
The alkenyloxy or fluorine-substituted carbon atom number that alkenyl that alkenyl, fluorine-substituted carbon atom number are 2-10, carbon atom number are 3-8
For the alkenyloxy of 3-8, and R3、R4Any one or more disjunct CH in shown group2It can be by cyclopenta, cyclobutyl
Or cyclopropyl replaces；
Z1、Z2Each independently represent singly-bound ,-CH2CH2Or-CH2O-；
It each independently represents
It each independently represents
And/orOne of or it is a variety of；
M indicates 1,2；
N indicates 0,1,2.
Compound shown in one or more formulas I is preferably one of compound shown in formula I -1 to I -2 or a variety ofization
Close object；Compound shown in one or more formulas II is preferably one or two kinds of compounds of II -1 to II -14 compound of formula；
Compound shown in one or more formulas III is preferably one of compound shown in formula III -1 to III -11 or a variety of chemical combination
Object,
Wherein, R3、R4Each independently representing alkyl, fluorine-substituted carbon atom number that carbon atom number is 1-10 is 1-10's
The chain that alkoxy that alkoxy that alkyl, carbon atom number are 1-10, fluorine-substituted carbon atom number are 1-10, carbon atom number are 2-10
The alkenyloxy or fluorine-substituted carbon atom number that alkenyl that alkenyl, fluorine-substituted carbon atom number are 2-10, carbon atom number are 3-8
For the alkenyloxy of 3-8, and R3、R4Any one or more disjunct CH in shown group2It can be by cyclopenta, cyclobutyl
Or cyclopropyl replaces.
Using in these displays of these liquid-crystal compositions, compound shown in Formulas I is added in LC medium, and is being drawn
After entering into LC box, applies between electrode and by UV photo polymerization or be crosslinked under voltage, the pre-dumping of liquid crystal molecule can be formed
Tiltedly.This is advantageous for simplifying LCD production process, raising response speed, reducing threshold voltage.
Compound shown in Formulas I provided by the invention has and that other monomers intersolubility is good, ultraviolet light tolerance is good etc. is excellent
Point.Have good intersolubility, charge conservation rate (VHR) height, polymerization activity high (monomer residue is few) as reactive mesogen (RM)
The advantages that, it is very suitable for as RM for PSA (orientation that polymer is supported), the liquid crystal of PS (polymer stabilizing) pattern formula
Mixture, especially in PSA-VA, PSA-IPS.
In addition, any one in the following product comprising compound shown in Formulas I, also belongs to protection scope of the present invention:
1) liquid-crystal composition；
2) optically anisotropic body of liquid-crystal composition；
I polymerizable compound of formula is due to the difference of substituent group, and the solubility property in liquid crystal, which can slightly have, to be distinguished, still
Mass ratio 1% and above additive amount may be implemented.
The additive amount (mass ratio) of I polymerizable compound of formula in a liquid crystal composition is preferably between 0.01-1%, into one
It walks between preferred 0.03-0.2%.
The additive amount (mass ratio) of compound shown in the formula II in a liquid crystal composition preferably between 15-60%, into
The preferred 20-40% of one step.
The additive amount (mass ratio) of compound shown in the formula III in a liquid crystal composition preferably between 20-60%, into
The preferred 30-50% of one step.
The liquid-crystal composition can be negativity liquid-crystal composition, can also include chemical combination shown in one or more formulas IV
Object
Wherein, R5、R6Each independently representing alkyl, fluorine-substituted carbon atom number that carbon atom number is 1-10 is 1-10's
The chain that alkoxy that alkoxy that alkyl, carbon atom number are 1-10, fluorine-substituted carbon atom number are 1-10, carbon atom number are 2-10
The alkenyloxy or fluorine-substituted carbon atom number that alkenyl that alkenyl, fluorine-substituted carbon atom number are 2-10, carbon atom number are 3-8
For the alkenyloxy of 3-8, and R5、R6Any one or more CH in shown group2It can be by cyclopenta, cyclobutyl or cyclopropyl
Substitution；
W indicates O, S or-CH2O-。
IV compound represented of formula is preferred are as follows:
R61Each independently representing carbon atom number is 2-6 alkyl.
The liquid-crystal composition can also include one or more V compounds represented of formula
Wherein, R7、R8Each independently representing alkyl, fluorine-substituted carbon atom number that carbon atom number is 1-10 is 1-10's
The chain that alkoxy that alkoxy that alkyl, carbon atom number are 1-10, fluorine-substituted carbon atom number are 1-10, carbon atom number are 2-10
The alkenyloxy or fluorine-substituted carbon atom number that alkenyl that alkenyl, fluorine-substituted carbon atom number are 2-10, carbon atom number are 3-8
For the alkenyloxy of 3-8；
Each independently represent 1,4- phenylene, 1,4- cyclohexylidene, 1,4- cyclohexadienylidene.
V compound represented of formula is preferred are as follows:
Wherein, R71、R81Each independently represent the alkyl that carbon atom number is 2-6 or the alkenyl that atomicity is 2-6；
R82Indicate that carbon atom number is the alkoxy of 1-5；
R71、R81Further preferably vinyl, 2- acrylic, 3- pentenyl.
The different proportion of each ingredient of liquid-crystal composition can show slightly discrepant performance, such as dielectric anisotropy Δ
ε, optical anisotropy Δ n, liquid crystal nematic phase be converted into transition temperature point CP, the low temperature stability inferior of liquid all can be poor
It is different, but identical feature is its rotary viscosity γ1It is lower.Applied to liquid crystal display device, quick response may be implemented.Liquid crystal
Composition has the high stability to light and heat.Liquid crystal display element or liquid crystal display comprising the liquid-crystal composition have
It is wider nematic temperature range, suitable or higher birefringence anisotropy Δ n, very high resistivity, good
The performances such as anti-ultraviolet property, high charge retention rate and low-steam pressure.The PSVA liquid crystal group applied suitable for display or TV
Object is closed, especially after long-play, is not had or significantly reduced image retention (image sticking).
The dopant of various functions can also be added in liquid-crystal compounds provided by the present invention, dopant content is preferred
Between 0.01-1%, these dopants are mainly antioxidant, ultraviolet absorbing agent, chiral agent.
Antioxidant, ultraviolet absorbing agent are preferred:
The integer of S expression 1-10.
The invention further relates to liquid crystal display elements or liquid crystal display comprising any one of the above liquid-crystal composition；It is described
Display element or display are active matrix display element or display or passive matrix display element or display.
The liquid crystal display element or the preferred active array addressing liquid crystal display element of liquid crystal display or liquid crystal display.
The active matrix display element or display are specially PSVA-TFT or IPS-TFT liquid crystal display element or display
Device.
Detailed description of the invention
Fig. 1 is compound spectra figure shown in b-2 in embodiment 2.
Specific embodiment
The present invention is further elaborated combined with specific embodiments below, but the present invention is not limited to following embodiments.Institute
State method is conventional method unless otherwise instructed.The raw material can be gotten from open business unless otherwise instructed.
For reaction process generally by the process of TLC monitoring reaction, the post-processing for reacting end is usually to wash, extract, closing
And solvent being evaporated off under dry after organic phase, decompression, and recrystallization, column chromatography, those skilled in the art can be under
The present invention is realized in the description in face.
Percentage in this specification is mass percent, and temperature is degree Celsius (DEG C), the specific meaning of other symbols and
Test condition is as follows:
Cp indicates clearing point (DEG C), the test of DSC sizing technique；
S-N indicates the crystalline state of liquid crystal to nematic fusing point (DEG C)；
Δ n indicates optical anisotropy, noFor the refractive index of ordinary light, neFor the refractive index of extraordinary ray, test condition is
25 ± 2 DEG C, 589nm, Abbe refractometer test；
Δ ε indicates dielectric anisotropy, Δ ε=ε∥-ε⊥, wherein ε∥For the dielectric constant for being parallel to molecular axis, ε⊥It is vertical
Directly in the dielectric constant of molecular axis, test condition is 25 ± 0.5 DEG C, 20 microns of parallel boxes, INSTEC:ALCT-IR1 test；
γ 1 indicates rotary viscosity (mPas), and test condition is 25 ± 0.5 DEG C, 20 microns of parallel boxes, INSTEC:ALCT-
IR1 test；
ρ indicates resistivity (Ω cm), and test condition is 25 ± 2 DEG C, and test equipment is TOYOSR6517 high resistant instrument and LE-
21 liquid electrodes.
VHR indicates voltage retention (%), and test condition is 20 ± 2 DEG C, voltage is ± 5V, pulse width 10ms, electricity
Press retention time 16.7ms.Test equipment is TOYOModel6254 liquid crystal property comprehensive tester.
τ indicate response time (ms), test equipment be DMS-501, test condition be 25 ± 0.5 DEG C, testing cassete 3.3
Micron IPS testing cassete, electrode spacing and electrode width are 10 microns, and frictional direction and electrode angle are 10 °.
T (%) indicates transmitance, and T (%)=100%* illuminated state (Vop) brightness/light-source brightness, test equipment DMS501 are surveyed
Strip part is 25 ± 0.5 DEG C, and testing cassete is 3.3 microns of IPS testing cassetes, and electrode spacing and electrode width are 10 microns, friction
Direction and electrode angle are 10 °.
Compound synthesis route shown in formula I:
K indicates H, CH3、CF3
Triethylamine, methylene chloride react 4 hours at room temperature.
The present patent application embodiment liquid crystal monomer structure indicates with code, liquid crystal ring structure, end group, linking group code
Representation method see the table below (one), table (two)
Table (one): the correspondence code of ring structure
Table (two): the corresponding code of end group and the link group
Citing:
C(5)CCV1
C(5)CB(2F,3F)O2
Embodiment 1
0.1mol (a-1) 26.6g is dissolved in 150ml methylene chloride, triethylamine 30.3g is added, first is added dropwise at room temperature
Base acryloyl chloride 0.25mol26g is stirred lower reaction four hours.
Washing removes remaining acid.
Lower solvent evaporated is depressurized, petroleum ether dissolution crosses silica gel column chromatography, solvent evaporated.Dehydrated alcohol recrystallization.It obtains
20.1g (a-2), yield 50%, HPLC:98.88%.
Embodiment 2:
Raw material are changed to (b-1)Synthetic method same as Example 1, obtains(b-2) (a-2), (b-2) compound have in a liquid crystal composition dissolubility it is good, in UV light
Under the conditions of the fast advantage of polymerization speed.
Embodiment 3:
Embodiment 4
The composition is kept for 1000 hours at -30 DEG C, is precipitated without (b-2), has extraordinary dissolution in low temperature.
Embodiment 5
Under identical UV polymerizing condition: 72mW/cm2@365nm, 200s；5mW/cm2@365nm90min, (b-2) monomer are residual
Allowance (50ppm) is lower than existing
Embodiment 6
Liquid-crystal composition of the invention has lower rotary viscosity γ 1, is used for liquid crystal display, quick sound may be implemented
It answers.It is particularly suitable for PSVA mode liquid crystal material.
Claims (8)
1. a kind of polymerizable compound as shown in formula I:
Wherein, Q is indicatedP1、P2It each independently represents
2. a kind of liquid-crystal composition, which is characterized in that include one or more type I compounds, II chemical combination of one or more formulas
III compound of object and one or more formulas,
Wherein, Q is indicatedP1、P2It each independently represents
R1、R2、R3、R4Each independently represent alkyl that alkyl, fluorine-substituted carbon atom number that carbon atom number is 1-10 are 1-10,
Alkenyl that alkoxy that alkoxy that carbon atom number is 1-10, fluorine-substituted carbon atom number are 1-10, carbon atom number are 2-10,
The alkenyloxy or fluorine-substituted carbon atom number that alkenyl that fluorine-substituted carbon atom number is 2-10, carbon atom number are 3-8 are 3-8
Alkenyloxy, and R3、R4Any one or more disjunct CH in shown group2It can be by cyclopenta, cyclobutyl or cyclopropyl
Base replaces；
Z1、Z2Each independently represent singly-bound ,-CH2CH2Or-CH2O-；
It each independently represents
It each independently represents
And/orOne of or it is a variety of；
M indicates 1,2；
N indicates 0,1,2.
3. liquid-crystal composition according to claim 2, which is characterized in that compound shown in one or more formulas I is
One of compound shown in formula I -1 to I -2 or multiple compounds；Compound shown in one or more formulas II is formula II -1
To one or two kinds of compounds of II -14 compound；Compound shown in one or more formulas III is III -1 to III -11 institute of formula
Show one of compound or multiple compounds,
Wherein, R3、R4Each independently represent alkyl that alkyl, fluorine-substituted carbon atom number that carbon atom number is 1-10 are 1-10,
Alkenyl that alkoxy that alkoxy that carbon atom number is 1-10, fluorine-substituted carbon atom number are 1-10, carbon atom number are 2-10,
The alkenyloxy or fluorine-substituted carbon atom number that alkenyl that fluorine-substituted carbon atom number is 2-10, carbon atom number are 3-8 are 3-8
Alkenyloxy, and R3、R4Any one or more disjunct CH in shown group2It can be by cyclopenta, cyclobutyl or cyclopropyl
Base replaces.
4. liquid-crystal composition according to claim 2, which is characterized in that the liquid-crystal composition is negativity liquid crystal combination
Object also includes one or more IV compounds represented of formula
Wherein, R5、R6Each independently represent alkyl that alkyl, fluorine-substituted carbon atom number that carbon atom number is 1-10 are 1-10,
Alkenyl that alkoxy that alkoxy that carbon atom number is 1-10, fluorine-substituted carbon atom number are 1-10, carbon atom number are 2-10,
The alkenyloxy or fluorine-substituted carbon atom number that alkenyl that fluorine-substituted carbon atom number is 2-10, carbon atom number are 3-8 are 3-8
Alkenyloxy, and R5、R6Any one or more CH in shown group2It can be substituted by cyclopenta, cyclobutyl or cyclopropyl；
W indicates O, S or-CH2O-。
5. liquid-crystal composition according to claim 2, which is characterized in that the liquid-crystal composition is negativity liquid crystal combination
Object also includes one or more V compounds represented of formula
Wherein, R7、R8Each independently represent alkyl that alkyl, fluorine-substituted carbon atom number that carbon atom number is 1-10 are 1-10,
Alkenyl that alkoxy that alkoxy that carbon atom number is 1-10, fluorine-substituted carbon atom number are 1-10, carbon atom number are 2-10,
The alkenyloxy or fluorine-substituted carbon atom number that alkenyl that fluorine-substituted carbon atom number is 2-10, carbon atom number are 3-8 are 3-8
Alkenyloxy；
Each independently represent 1,4- phenylene, 1,4- cyclohexylidene, 1,4- cyclohexadienylidene.
6. liquid crystal display element or liquid crystal display comprising any liquid-crystal composition in claim 2-5；The display
Element or display are active matrix display element or display or passive matrix display element or display.
7. liquid crystal display element according to claim 6 or liquid crystal display, it is characterised in that: the Active Matrix LCD At
Element or display are PSVA-TFT liquid crystal display element or display.
8. the optically anisotropic body that the liquid-crystal composition comprising compound described in claim 1 is formed.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710919266.XA CN109593040B (en) | 2017-09-30 | 2017-09-30 | Polymerizable compound containing propenyl tetrapolymerized group and composition comprising the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710919266.XA CN109593040B (en) | 2017-09-30 | 2017-09-30 | Polymerizable compound containing propenyl tetrapolymerized group and composition comprising the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109593040A true CN109593040A (en) | 2019-04-09 |
| CN109593040B CN109593040B (en) | 2023-03-07 |
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| CN114957000A (en) * | 2022-06-24 | 2022-08-30 | 陕西科技大学 | Biomass-based active diluent double-bonded magnolol and preparation method and application thereof |
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