CN103468272A - Liquid crystal composite - Google Patents

Liquid crystal composite Download PDF

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CN103468272A
CN103468272A CN2013104030213A CN201310403021A CN103468272A CN 103468272 A CN103468272 A CN 103468272A CN 2013104030213 A CN2013104030213 A CN 2013104030213A CN 201310403021 A CN201310403021 A CN 201310403021A CN 103468272 A CN103468272 A CN 103468272A
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liquid crystal
liquid
monomer
crystal composition
crystal monomer
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CN103468272B (en
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苏峻纬
陈建华
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Suzhou Shengze Science And Technology Pioneer Park Development Co ltd
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CPT Video Wujiang Co Ltd
Chunghwa Picture Tubes Ltd
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Abstract

The invention relates to a liquid crystal composite which comprises a first liquid crystal monomer, a second liquid crystal monomer and a polymerizable material, wherein the content of the first liquid crystal monomer is 5%-10% and the content of the second liquid crystal monomer is 90%-95% in terms of the total weight of the first liquid crystal monomer and the second liquid crystal monomer; the first liquid crystal monomer is selected from a group which consists of compounds with tetracyclic structures as shown in a formula 1 to a formula 6, R is C3-C12 alkyl, X is -COO-, -C is equivalent to C- or -N=N-, and Y is -CN; the second liquid crystal monomer is in a bicyclic or tricyclic structure.

Description

Liquid-crystal composition
Technical field
The invention relates to a kind of liquid-crystal composition, and particularly relevant for a kind of liquid-crystal composition that comprises the liquid crystal monomer with Fourth Ring structure.
Background technology
In recent years, along with scientific and technological development, the transparent liquid crystal indicating meter has become one of direction of utmost point wish development in current opto-electronics.With regard to existing transparent liquid crystal indicating meter, mainly that superpotential the driving with driving forms scattering and the display mode penetrated, so that can not need the situation that attaches Polarizer to be issued to display effect, so it has processing procedure and simply reaches the advantage that cost of manufacture is low.
Yet the liquid crystal used due to existing transparent liquid crystal indicating meter has the poor shortcoming of scattering states usually, will cause the transparent liquid crystal indicating meter to have the bad and standby restricted problem of applicability of display characteristic.Therefore, improving the scattering states of liquid crystal and contrast will be the problem of needing at present solution badly.
Summary of the invention
The invention provides a kind of liquid-crystal composition, it has the characteristic of high scattering states and high contrast after polymerization.
Liquid-crystal composition of the present invention comprises the first liquid crystal monomer and the second liquid crystal monomer, wherein in the gross weight of the first liquid crystal monomer and the second liquid crystal monomer, the content of the first liquid crystal monomer is 5wt% to 10wt%, and the content of the second liquid crystal monomer is 90wt% to 95wt%.The first liquid crystal monomer selects free style 1 to group that the compound that has the Fourth Ring structure shown in formula 6 forms:
Figure BDA0000378358540000021
Wherein R is C 3-C 12alkyl, X is-COO-,-C ≡ C-or-N=N-, and Y is-CN.The second liquid crystal monomer has two rings or tricyclic structure.
Based on above-mentioned, liquid-crystal composition proposed by the invention has the liquid crystal monomer of Fourth Ring structure, makes the liquid-crystal composition after polymerization have the characteristic of high scattering states and high contrast.
For above-mentioned feature and advantage of the present invention can be become apparent, special embodiment below, and coordinate appended graphic being described in detail below.
The accompanying drawing explanation
Fig. 1 is the driving voltage of the testing cassete of the liquid-crystal composition of injection comparative example and the graph of a relation of penetration coefficient.
The driving voltage of the testing cassete of the liquid-crystal composition that Fig. 2 is injection experiments example 1 and the graph of a relation of penetration coefficient.
The driving voltage of the testing cassete of the liquid-crystal composition that Fig. 3 is injection experiments example 2 and the graph of a relation of penetration coefficient.
The driving voltage of the testing cassete of the liquid-crystal composition that Fig. 4 is injection experiments example 3 and the graph of a relation of penetration coefficient.
Embodiment
In this article, sometimes with key line formula (skeletal formula), mean compound structure.This representation can the omission of carbon atom, hydrogen atom and hydrocarbon key.Certainly, have in structural formula and clearly draw the functional group, be as the criterion with the person of illustrating.
In this article, the scope meaned by " numerical value is to another numerical value ", be that a kind of summary that enumerates all numerical value in this scope in specification sheets of avoiding means mode.Therefore, the record of a certain special value scope, contain any number in this numerical range and by any number in this numerical range, defined than the fractional value scope, the same than the fractional value scope with this as in specification sheets, expressly writing out this any number.
In order to prepare the liquid-crystal composition that can reach high scattering states and high contrastive feature, the present invention proposes a kind of liquid-crystal composition, and it can reach above-mentioned advantage.Below, the example that really can implement according to this as the present invention especially exemplified by embodiment.
Liquid-crystal composition provided by the invention comprises the first liquid crystal monomer and the second liquid crystal monomer, wherein in the gross weight of the first liquid crystal monomer and the second liquid crystal monomer, the content of the first liquid crystal monomer is 5wt% to 10wt%, and the content of the second liquid crystal monomer is 90wt% to 95wt%.Below will describe above-mentioned two kinds of components in detail.
The first liquid crystal monomer of the present invention selects free style 1 to group that the compound that has the Fourth Ring structure shown in formula 6 forms:
Figure BDA0000378358540000031
Figure BDA0000378358540000041
Wherein R is C 3-C 12alkyl, X is-COO-,-C ≡ C-or-N=N-, and Y is-CN.
Specifically, the first liquid crystal monomer of the present invention is the compound with Fourth Ring structure.In addition, in one embodiment, the first liquid crystal monomer is for example the compound shown in above-mentioned formula 1.Compound shown in formula 1 can be the compound shown in following formula 7:
The second liquid crystal monomer of the present invention has two rings or tricyclic structure, and wherein ring structure can be phenyl ring, cyclohexane ring or heterocycle.In addition, because the first liquid crystal monomer has the Fourth Ring structure, and the second liquid crystal monomer has two rings or tricyclic structure, therefore compare with the second liquid crystal monomer, the first liquid crystal monomer has high birefringence rate and high clear point.In addition, the second liquid crystal monomer of the present invention is for example commercially available prod.In one embodiment, the second liquid crystal monomer is for example to select free style 8 to group that the compound shown in formula 11 forms:
In addition, although above disclosed formula 8 to the compound shown in formula 11, but the second liquid crystal monomer of the present invention is not limited to this, so long as the known arbitrary liquid crystal monomer with two rings or tricyclic structure of person with usual knowledge in their respective areas all falls into category of the present invention.
Liquid-crystal composition of the present invention can also comprise polymerizable material.In the gross weight of liquid-crystal composition, the content of polymerizable material is about between 20wt% to 50wt%.Polymerizable material comprises polyether glycol acrylic group monomer, polymerizable mesogenic initiator, acrylic resin monomer, polythiol monomer and composition thereof.In the gross weight of polymerizable material, the content that the content that the content that the content of polyether glycol acrylic group monomer is 10wt% to 30wt%, polymerizable mesogenic initiator is 0.5wt% to 5wt%, acrylic resin monomer is 10wt% to 30wt% and polythiol monomer is 10wt% to 30wt%.In addition, polymerizable material can also comprise solvent.
In one embodiment, polyether glycol acrylic group monomer is for example the compound shown in formula 12:
In one embodiment, the polymerizable mesogenic initiator that polymerizable material is used is for example hot initiator or light initiator.Specifically, polymerizable mesogenic initiator of the present invention can be for example that the model of silicon grace exotic materials limited-liability company is the hot initiator that PN-23 or model are PN-31J, or polymerizable mesogenic initiator of the present invention is for example the compound shown in formula 13:
In one embodiment, the acrylic resin monomer is for example the compound shown in formula 14:
Figure BDA0000378358540000053
In one embodiment, the polythiol monomer is for example the compound shown in formula 15:
In one embodiment, the solvent that is used for diluting polymer concentration is for example isopropylcarbinol (isobutyl alcohol, IBA), butanone (methyl ethyl ketone, MEK) or methoxyacetic acid propyl ester (propylene glycol monomethyl ether acetate, PMA).
What deserves to be explained is, as mentioned above, because the first liquid crystal monomer has high birefringence rate and high clear point, therefore after the first liquid crystal monomer and polymerizable material effect (associated description will illustrate below), will produce preferably scattering states coupling, and then make liquid-crystal composition of the present invention there is the characteristic of high scattering states and high contrast.In one embodiment, the scattering states effect of liquid-crystal composition of the present invention is about 1.5% to 3%, penetrate the state effect and be about 80% to 85%, and contrast is about 25 to 50.
Illustrate further, aforesaid liquid-crystal composition is for example heated or irradiation so that after liquid-crystal composition produces polyreaction, can be used as through the liquid-crystal composition of polymerization the liquid crystal layer that is applicable to the transparent liquid crystal indicating meter, its reason is as described below.
Through the acrylic resin monomer in polymerizable material and the effect of polymerizable mesogenic initiator, can impel the polyether glycol acrylic group monomer of property class like interfacial agent, produce polyreaction with the first liquid crystal monomer and second liquid crystal monomer of part, and form the high molecule liquid crystal born of the same parents on the surface of the two substrates be oppositely arranged of transparent liquid crystal indicating meter.In addition, see through polythiol monomer in polymerizable material and can further strengthen the surface of two substrates of transparent liquid crystal indicating meter and high molecule liquid crystal born of the same parents' sticking power, so that the high molecule liquid crystal born of the same parents tend to be dispersed in the surface of substrate.When between two substrates, having potential difference, aforementioned high molecule liquid crystal born of the same parents' optical axis direction is consistent in fact, so the time incident light can pass the transparent liquid crystal indicating meter, and make the part zone of transparent liquid crystal indicating meter present clear state; Otherwise, when the potential difference between two substrates is essentially zero, high molecule liquid crystal born of the same parents' optical axis direction intermeshes in fact, so the time incident light can be by the scattering of high molecule liquid crystal born of the same parents institute, and make the part zone of transparent liquid crystal indicating meter present scattering states.
Thus, utilize above-mentioned clear state and the display mode of scattering states, the transparent liquid crystal indicating meter that comprises liquid-crystal composition of the present invention is picture capable of displaying image and do not need to use Polarizer, and sees through and use the first liquid crystal monomer, and the display characteristic of transparent liquid crystal indicating meter can be raised.In addition, in one embodiment, described transparent liquid crystal indicating meter can be penetration indicating meter or reflected displaying device.
Below will enumerate the liquid-crystal composition of comparative example and a plurality of experimental example 1-3, and the through characteristic under different voltage is measured to each liquid-crystal composition, so that the liquid crystal characteristic of each liquid-crystal composition to be described.
Prepare the main raw that the liquid-crystal composition of comparative example and experimental example 1-3 uses as follows:
The first liquid crystal monomer: the compound shown in formula 7;
The second liquid crystal monomer: formula 8 is to the compound shown in formula 11;
Polymerizable material: formula 12 to the compound shown in formula 15 and solvent is isopropylcarbinol.
The method for preparing the liquid-crystal composition of comparative example and experimental example 1-3 comprises mixes above-mentioned the first liquid crystal monomer, the second liquid crystal monomer with polymerizable material, wherein composition and the ratio thereof of the first liquid crystal monomer in the liquid-crystal composition of comparative example and embodiment 1-3 and the second liquid crystal monomer are listed in table 1 in detail, and in the liquid-crystal composition of comparative example and experimental example 1-3, the shared weight percent of polymerizable material is 20% to 50%, and polymerizable material has identical proportion of composing.Specifically, in described polymerizable material, the shared weight percent of the compound shown in formula 12 is 10% to 30%, the shared weight percent of compound shown in formula 13 is 0.5% to 5%, the shared weight percent of compound shown in formula 14 be 10% to 30% and formula 15 shown in the shared weight percent of compound be 10% to 30%.
Table 1
Figure BDA0000378358540000081
Liquid-crystal composition to comparative example and experimental example 1-3 carries out the measurement of penetration coefficient, and its measurement as shown in Figures 1 to 4.
Fig. 1 is the driving voltage of the testing cassete (Test Cell) of the liquid-crystal composition of injection comparative example and the graph of a relation of penetration coefficient.The driving voltage of the testing cassete of the liquid-crystal composition that Fig. 2 is injection experiments example 1 and the graph of a relation of penetration coefficient.The driving voltage of the testing cassete of the liquid-crystal composition that Fig. 3 is injection experiments example 2 and the graph of a relation of penetration coefficient.The driving voltage of the testing cassete of the liquid-crystal composition that Fig. 4 is injection experiments example 3 and the graph of a relation of penetration coefficient.In this, measurement step comprises provides testing cassete, and it comprises two substrates that are oppositely arranged with conducting film; Liquid-crystal composition is injected between described two substrates; Then make described testing cassete through the irradiation processing procedure.
From Fig. 1 to Fig. 4, with the liquid-crystal composition of the comparative example that does not contain the first liquid crystal monomer, compare, when the liquid-crystal composition of the experimental example 1-3 that contains the first liquid crystal monomer is zero (being scattering states) at driving voltage, present lower penetration coefficient (approximately 3%), and, when clear state, present suitable penetration coefficient (approximately 83%).And, from also above-mentioned, with the testing cassete of the liquid-crystal composition that injects the comparative example do not contain the first liquid crystal monomer, to compare, the testing cassete that injects the liquid-crystal composition of the experimental example 1-3 that contains the first liquid crystal monomer has higher contrast (approximately 28).In other words, by the driving voltage of testing cassete and penetration coefficient, concern that susceptible of proof liquid-crystal composition of the present invention has the characteristic of high scattering states and high contrast really, and adopt the display characteristic of transparent liquid crystal indicating meter of this liquid-crystal composition made good.
In sum, liquid-crystal composition proposed by the invention has the liquid crystal monomer of Fourth Ring structure, makes the liquid-crystal composition after polymerization have the characteristic of high scattering states and high contrast.In addition, liquid-crystal composition proposed by the invention is applicable to the transparent liquid crystal indicating meter, and can promote its display characteristic.

Claims (9)

1. a liquid-crystal composition comprises:
The first liquid crystal monomer, it selects free style 1 to group that the compound that has the Fourth Ring structure shown in formula 6 forms:
Wherein R is C 3-C 12alkyl, X is-COO-,-C ≡ C-or-N=N-, and Y is-CN; And
The second liquid crystal monomer, it has two rings or tricyclic structure,
Wherein, in the gross weight of this first liquid crystal monomer and this second liquid crystal monomer, the content of this first liquid crystal monomer is 5wt% to 10wt%, and the content of this second liquid crystal monomer is 90wt% to 95wt%.
2. liquid-crystal composition as claimed in claim 1, is characterized in that, this first liquid crystal monomer as shown in Equation 1:
Figure FDA0000378358530000012
3. liquid-crystal composition as claimed in claim 1, is characterized in that, this first liquid crystal monomer as shown in Equation 7:
Figure FDA0000378358530000013
4. liquid-crystal composition as claimed in claim 1, is characterized in that, this second liquid crystal monomer is to select free style 8 to group that the compound shown in formula 11 forms:
Figure FDA0000378358530000021
5. liquid-crystal composition as claimed in claim 1, it is characterized in that, also comprise polymerizable material, it comprises polyether glycol acrylic group monomer, polymerizable mesogenic initiator, acrylic resin monomer, polythiol monomer and composition thereof, wherein, in the gross weight of this liquid-crystal composition, the content of this polymerizable material is 20wt% to 50wt%.
6. liquid-crystal composition as claimed in claim 5, is characterized in that, this polyether glycol acrylic group monomer comprises:
Figure FDA0000378358530000022
7. liquid-crystal composition as claimed in claim 5, is characterized in that, this polymerizable mesogenic initiator comprises:
8. liquid-crystal composition as claimed in claim 5, is characterized in that, this acrylic resin monomer comprises:
Figure FDA0000378358530000031
9. liquid-crystal composition as claimed in claim 5, is characterized in that, this polythiol monomer comprises:
Figure FDA0000378358530000032
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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2080820A (en) * 1980-06-27 1982-02-10 Secr Defence Liquid crystal composition containing a cyanobiphenyl and a phenyl benzoate
JPH06287559A (en) * 1993-02-03 1994-10-11 Merck Patent Gmbh Liquid crystal medium
GB2280681A (en) * 1993-08-06 1995-02-08 Merck Patent Gmbh Mesogenic menthol derivatives for thermochromic liquid crystalline media and inks
US5518654A (en) * 1989-12-14 1996-05-21 The Secretary Of State For Defence In Her Britannic Majesty's Government Of The U.K. Of Gt. Britain And Northern Ireland Light modulating material comprising polymer dispersed liquid crystals
GB2393966A (en) * 2002-08-14 2004-04-14 Merck Patent Gmbh High-twist liquid-crystalline medium and liquid-crystal display
CN102031121A (en) * 2009-09-29 2011-04-27 奇美电子股份有限公司 Liquid crystals composition and liquid crystal display
CN102876334A (en) * 2012-11-23 2013-01-16 福建华映显示科技有限公司 Liquid crystal composition, liquid crystal display panel and preparation method thereof

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2080820A (en) * 1980-06-27 1982-02-10 Secr Defence Liquid crystal composition containing a cyanobiphenyl and a phenyl benzoate
US5518654A (en) * 1989-12-14 1996-05-21 The Secretary Of State For Defence In Her Britannic Majesty's Government Of The U.K. Of Gt. Britain And Northern Ireland Light modulating material comprising polymer dispersed liquid crystals
JPH06287559A (en) * 1993-02-03 1994-10-11 Merck Patent Gmbh Liquid crystal medium
GB2280681A (en) * 1993-08-06 1995-02-08 Merck Patent Gmbh Mesogenic menthol derivatives for thermochromic liquid crystalline media and inks
GB2393966A (en) * 2002-08-14 2004-04-14 Merck Patent Gmbh High-twist liquid-crystalline medium and liquid-crystal display
CN102031121A (en) * 2009-09-29 2011-04-27 奇美电子股份有限公司 Liquid crystals composition and liquid crystal display
CN102876334A (en) * 2012-11-23 2013-01-16 福建华映显示科技有限公司 Liquid crystal composition, liquid crystal display panel and preparation method thereof

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Effective date of registration: 20230509

Address after: No. two, No. 1188 West Ring Road, Shengze Town, Wujiang District, Jiangsu, Suzhou

Patentee after: Suzhou Shengze science and Technology Pioneer Park Development Co.,Ltd.

Address before: No. 555 Jiangxing East Road, Tongli District, Wujiang Economic Development Zone, Suzhou City, Jiangsu Province, 215217

Patentee before: CPTW (WUJIANG) Co.,Ltd.

Patentee before: Chunghwa Picture Tubes, Ltd.