CN1504538A - Liquid crystal display orientation layer material and preparing method thereof - Google Patents
Liquid crystal display orientation layer material and preparing method thereof Download PDFInfo
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- CN1504538A CN1504538A CNA021538344A CN02153834A CN1504538A CN 1504538 A CN1504538 A CN 1504538A CN A021538344 A CNA021538344 A CN A021538344A CN 02153834 A CN02153834 A CN 02153834A CN 1504538 A CN1504538 A CN 1504538A
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Abstract
The invention relates a polymer having a formula (I) described in the specification, wherein R1, R2, n, x, y and G are defined in the specification. The invention also discloses the process for preparing the polymer, and the use of the polymer as orientation layer material in the LCDs.
Description
Invention field
The present invention relates to be used for liquid-crystal display (Liquid CrystalDisplay, LCD), can make the stable and evenly distributed oriented layer material of liquid crystal property.
Background technology
One of gordian technique of liquid crystal aligning technology system decision liquid-crystal display quality is because the quality of liquid crystal aligning technology can directly influence the quality of final LCD assembly.The high quality liquid-crystal display requires liquid crystal that stable and uniform initial arrangement is arranged, and is called liquid crystal aligning layer and have the thin layer of inducing liquid crystal to align effect.
Present known liquid crystal display (Liquid Crystal Display, LCD) the oriented layer material of Shi Yonging has polystyrene and derivative thereof, polyimide, polyvinyl alcohol, polyester, Resins, epoxy, polyurethane, polysilane etc., but modal then be polyimide (polyimide).These materials can utilize certain methods that liquid crystal aligning is arranged, and carry out little groove facture etc. as film rubbing manipulation (rubbed film), inclination evaporation SiOx embrane method (obliquelyevaporated SiOx) with to film.
In many liquid crystal aligning aligning methods, rubbing method is owing to simple, the convenient most widely used method in liquid-crystal display is made at present that becomes.This method generally is that substrate is pressed onto the Velveting surface of evenly moving, and utilizes friction to reach and aligns.The method of the round roller friction of also useful bag Velveting, this method can produce the observable little groove of electron microscope at substrate surface, and on the surface of this little groove, liquid crystal molecule is parallel or favours the groove direction to be arranged, and can reach the orientation of liquid crystal.Yet rubbing method has a lot of important disadvantages.At first, friction can produce dust, thereby reduces the quality of liquid-crystal display.Secondly, friction can produce static, thereby destroys thin film transistor, makes that the qualification rate of product is not high.Moreover friction can only be implemented at planar surface, and can't be applied to curved surface.Therefore, rubbing manipulation can not meet demand in the market.
Linear polarization photopolymerization reaction (linearly polarized photo-polymerization, liquid crystal aligning technology LPP) are used in existing recently report.This kind technology is the surface with linearly polarized photon irradiated polyethylene alcohol laurate, makes wherein two key groups generations molecule crosslinked and form anisotropic polymeric membrane.Original molecular linkage is regularly arranged at substrate surface, when when polarized ultraviolet shines, causes the generation of anisotropic reactive, and formed polymeric membrane works the effect of aligning to liquid crystal, is called optical alignment film (photo-alignment layer).This kind advanced person's liquid crystal aligning aligning method is called the liquid crystal photo-alignment method.
The liquid crystal photo-alignment method is a kind of contactless surface treatment method, it is applied to the linear polarization light polymerization technique in the manufacturing of liquid-crystal display, not only overcome the above-mentioned shortcoming that rubbing method brings, and make that the manufacturing of display assembly is simple more, convenient, can improve the qualification rate of product, thereby reduce the cost of product.Therefore the liquid crystal photo-alignment method particularly in the manufacturing of large screen display, has good application prospects in high quality lcd, and liquid crystal aligning layer is a critical material of implementing this method.This case inventor finds a kind of epoxide resin polymer through broad research, can be used as the material of orientation layer of liquid crystal display unit.
Summary of the invention
One of the present invention purpose provides the method for making of a kind of epoxide resin polymer and this polymkeric substance.
Another purpose of the present invention provides a kind of liquid crystal orientation layer material that contains this epoxide resin polymer.
Detailed Description Of The Invention
The present invention relates to a kind of epoxide resin polymer, its structure is suc as formula shown in (I):
Wherein:
N is the integer greater than 1, is preferably the integer that reaches up to 5000 greater than 1;
R
1And R
2Respectively be respectively hydrogen atom, halogen, nitro, C
1-C
10Alkyl (is preferably C
1-C
6Alkyl) or C
1-C
10Alkoxyl group (is preferably C
1-C
6Alkoxyl group), and x and y system is respectively 1 to 3 integer, and R
1And R
2System lays respectively at ortho position, a position or the contraposition of phenyl ring; And
G system is selected from following group:
(1) Racemic glycidol ethers
-CH
2-O-R-O-CH
2-
Wherein R system is selected from following groups:
(a) Bisphenol F type
(b) bisphenol S type
(c) Hydrogenated Bisphenol A type
(d) halo type
(2) Racemic glycidol amine
R wherein
3Be C
1-C
6Alkyl;
(3) glycidyl ester class
(4) glycerols Resins, epoxy
(5) glycols Resins, epoxy
-CH
2-O-CH
2-CH
2-O-CH
2-；
(6) silicone based Resins, epoxy
(7) cycloaliphatic epoxy resin class
(8) acid imide Resins, epoxy
R wherein
4Be aryl.
According to the present invention, the R in the above-mentioned acid imide Resins, epoxy
4Together with two nitrogen-atoms that are connected with it is derived from aromaticity two aminates.Be applicable to that aromaticity two aminates among the present invention are to be familiar with those skilled in the art institute well known, it for example can be United States Patent (USP) the 4th, 954, person described in No. 612.The disclosure of this patent is incorporated herein now to be further described at these aromaticity two aminates.
According to preferred embodiment of the present invention, each R in formula of the present invention (I) polymkeric substance
1System is respectively hydrogen, C
1-C
6Alkyl, C
1-C
6Alkoxy or halogen; Be preferably and be selected from adjacent methyl, an ethyl, methoxyl group is reached chloro; And each R
2System is respectively hydrogen, C
1-C
6Alkyl, C
1-C
6Alkoxy or halogen, be preferably be selected from hydrogen, neighbour-methyl ,-ethyl, right-methoxyl group and right-chlorine.
The present invention discloses a kind of method of preparation this formula (I) epoxide resin polymer in addition, and it comprises:
(I) epoxy monomer and aniline monomer are carried out polycondensation under 50-100 ℃ temperature, produce the prepolymer of hydroxyl, wherein epoxy monomer is to be selected from following groups:
(1) Racemic glycidol ethers
Wherein R is:
(a) Bisphenol F type
(b) bisphenol S type
(c) Hydrogenated Bisphenol A type
And
(d) halo type
(2) glycidyl ester class
(3) Racemic glycidol amine
R wherein
3Has definition same as described above;
(4) the alicyclic ring same clan
(5) acid imide
R wherein
4Has definition same as described above;
(6) silicone based
(7) glycerols Resins, epoxy
And
(8) glycols Resins, epoxy
Aniline monomer then is selected from the compound of following (II):
R wherein
2Each is selected from hydrogen atom, halogen, nitro, C respectively
1-C
10Alkyl (is preferably C
1-C
6Alkyl) or C
1-C
10Alkoxyl group (is preferably C
1-C
6Alkoxyl group), and y is 1 to 3 integer, and each R
2System lays respectively at ortho position, a position or the contraposition of phenyl ring; And
(II) acid absorber with cinnyl halide monomer, solvent and use optionally adds in the prepolymer of step (I) gained, temperature of reaction is controlled under 30 to 100 ℃, and with acquisition formula (I) polymkeric substance,
Wherein cinnyl halide monomer system is selected from the compound of following formula (III):
R wherein
1Respectively be respectively hydrogen atom, halogen, nitro, C
1-C
10Alkyl (is preferably C
1-C
6Alkyl) or C
1-C
10Alkoxyl group (is preferably C
1-C
6Alkoxyl group), and x is 1 to 3 integer, and each R
1System lays respectively at ortho position, a position or the contraposition of phenyl ring, and W is a halogen.
Be applicable to formula (II) aniline compound in the step (a), wherein each R
2Be preferably H, C
1-C
6Alkyl, C
1-C
6Alkoxy or halogen.Be applicable to formula of the present invention (II) aniline compound, such as but not limited to aniline, o-toluidine, m-ethyl aniline, P-nethoxyaniline or p-Chlorobenzoic acid amide.
Be applicable to formula (III) the cinnyl halogenide among the present invention, for example comprise cinnyl chlorination thing, each R in its Chinese style (III)
1Be preferably hydrogen, C
1-C
6Alkyl, C
1-C
6Alkoxy or halogen.Can be used for cinnyl chlorination thing among the present invention such as but not limited to cinnamyl chloride, adjacent methyl cinnamyl chloride, an ethyl cinnamyl chloride, to the methoxyl group cinnamyl chloride or to the chloro cinnamyl chloride.
The used solvent of previous reaction is aprotic polar solvent usually, the preferred solvents system that can be used for this reaction is selected from tetrahydrofuran (THF) (THF), N, dinethylformamide (DMF), methyl-sulphoxide (DMSO), N,N-dimethylacetamide (DMAC), N-Methyl pyrrolidone (NMP) or its mixture.
The employed acid absorber of previous reaction be usually a kind of can with the alkali of acid-respons, its preferable system is selected from pyridine (Py), triethylamine (TEA), N-ethylmorpholine NEM), xylidine (DMAN), or its mixture.
Alleged herein " alkyl " is such as but not limited to methyl, ethyl, propyl group, sec.-propyl, butyl, tributyl, amyl group, hexyl etc.
Alleged herein " alkoxyl group " is such as but not limited to methoxyl group, oxyethyl group, propoxy-, butoxy, the 3rd butoxy etc.
Alleged herein " halogen " is meant fluorine, chlorine, bromine and iodine atom, is preferably chlorine and bromine, and the best is a chlorine.
Epoxide resin polymer of the present invention has the molecular-weight average between about 5,000 to 200,000.Situation on its polyreaction is decided, and the percentage of grafting of this polymkeric substance can be 50% to 100%.
Epoxide resin polymer of the present invention can be used in the liquid crystal orientation layer material of liquid-crystal display, and this liquid crystal orientation layer material can be incorporated epoxide resin polymer of the present invention in the liquid crystal orientation layer material into by known method in any this skill.For example, epoxide resin polymer of the present invention can be dissolved with aprotic solvent, be made into certain density homogeneous solution, by the desk-top even surperficial rotary plating of machine that stir in base material, and shine with polarized ultraviolet (for example wavelength is 365nm), (2+2) cyclization enough takes place in the two bond energys in the contained laurate group of its side chain, makes the polymeric film anisotropy, thereby induces the liquid crystal molecular orientation.This can be applicable to twisted nematic (TN), super-twist nematic (STN), film transistor type (TFT) liquid-crystal display through the layer assembling Liquid crystal module of light orientation, and it has advantages such as giant-screen, on-plane surface, high information content, high resolving power.
Following examples are to be used for that the invention will be further described, rather than in order to limit the scope of the invention.Modification that any those skilled in the art of being familiar with can reach easily and change are included within this case specification sheets disclosure and the claims.
Embodiment
Embodiment 1:
Bisphenol F type glycidyl ether based epoxy resin-aniline prepolymer
Synthetic
Be equipped with in the single port flask of agitator one and add Bisphenol F type glycidyl ether based epoxy resin and aniline respectively, the feed ratio of control functional group is 1: 1.Be reaction 30 to 40 hours under 60 to 80 ℃ the condition with the oil bath controlled temperature, obtain slightly yellowy solid mass.With the gained solid mass with CHCl
3Dissolving precipitates prepolymer with a large amount of acetone then, and there is the thick material of one deck at the bottle end, and it is dry that this material is put into vacuum drying oven, obtains a stratiform solid.
Synthesizing of cinnamyl chloride
Be equipped with in one and add 14.8 gram (0.1 mole) styracins in the there-necked flask of reflux condensing tube and gas absorber, stir down and add 7.5 milliliters of (12.3 grams gradually with dropping funnel, 0.105 thionyl chloride mole), with reaction under the condition of in 50 to 80 ℃ of water-bath controlled temperature 6 to 10 hours, obtain white solid.
Synthesizing of photosensitive polymers
Be equipped with in one and add the gained prepolymer in the there-necked flask of reflux exchanger, obtain colourless solution, add a spot of anhydrous pyridine again with the anhydrous tetrahydro furan dissolving.In flask, slowly add the anhydrous tetrahydrofuran solution that is dissolved with cinnamyl chloride then, the proportioning-OH of control functional group: COCl=1: 1.5, reacted 4 to 12 hours under 30 to 60 ℃ condition with the water-bath controlled temperature, must slightly yellowy polymers soln.Polymers soln is added the precipitation that makes in the methanol solution gradually, through suction filtration, wash, place vacuum drying oven to dry, the white powder solid.
The preparation liquid crystal orientation layer material
The photosensitivity Bisphenol F type glycidyl ether based epoxy resin class material of above gained is dissolved with chloroform,, carried out photo-crosslinking according to 5 to 30 minutes, promptly obtain a liquid crystal photo-alignment layer material with polarized ultraviolet (365nm) with desk-top spreader rotary plating on substrate.
Embodiment 2
Repeat the step of embodiment 1, only styracin is changed into adjacent tolyl acrylic acid.
Embodiment 3
Repeat the step of embodiment 1, only styracin is changed into a tolyl acrylic acid.
Embodiment 4
Repeat the step of embodiment 1, only styracin is changed into tolyl acrylic acid.
Embodiment 5
Repeat the step of embodiment 1, only styracin is changed into chloro-cinnamic acid.
Embodiment 6
Repeat the step of embodiment 1, only styracin is changed into nitrocinnamic acid.
Embodiment 7
Repeat the step of embodiment 1, only change styracin into p-methoxycinnamic acid.
Embodiment 8
Repeat the step of embodiment 1, only styracin is changed into ethyl-cinnamic acid.
Embodiment 9
Repeat the step of embodiment 1, only styracin is changed into ethoxy-cinnamic acid.
Embodiment 10
Repeat the step of embodiment 1, only styracin is changed into ethoxy-cinnamic acid.
Embodiment 11 to 20
Repeat the step of embodiment 1 to 10, only change Bisphenol F type glycidyl ether based epoxy resin into bisphenol-s epoxy resin.
Embodiment 21 to 30
Repeat the step of embodiment 1 to 10, only change Bisphenol F type glycidyl ether based epoxy resin into '-biphenyl diphenol type glycidyl ether based epoxy resin.
Embodiment 31 to 40
Repeat the step of embodiment 1 to 10, only change Bisphenol F type glycidyl ether based epoxy resin into Hydrogenated Bisphenol A type glycidyl ether based epoxy resin.
Embodiment 41 to 50
Repeat the step of embodiment 1 to 10, only change Bisphenol F type glycidyl ether based epoxy resin into halo type glycidyl ether based epoxy resin.
Embodiment 51 to 60
Repeat the step of embodiment 1 to 10, only change Bisphenol F type glycidyl ether based epoxy resin into the glycidyl ester based epoxy resin.
Embodiment 61 to 70
Repeat the step of embodiment 1 to 10, only change Bisphenol F type glycidyl ether based epoxy resin into the Racemic glycidol amine epoxy resin.
Embodiment 71 to 80
Repeat the step of embodiment 1 to 10, only change Bisphenol F type glycidyl ether based epoxy resin into aliphatic epoxy resin.
Embodiment 81 to 90
Repeat the step of embodiment 1 to 10, only change Bisphenol F type glycidyl ether based epoxy resin into acid imide Resins, epoxy.
Embodiment 91 to 100
Repeat the step of embodiment 1 to 10, only change Bisphenol F type glycidyl ether based epoxy resin into silicone based Resins, epoxy.
Embodiment 101 to 110
Repeat the step of embodiment 1 to 10, only change Bisphenol F type glycidyl ether based epoxy resin into glycerols Resins, epoxy.
Embodiment 111 to 120
Repeat the step of embodiment 1 to 10, only change Bisphenol F type glycidyl ether based epoxy resin into glycols Resins, epoxy.
Test result
Corresponding prepolymer and photosensitive polymers that the reaction of above-mentioned various epoxy resins and various phenyl amines linear condensation is obtained see through infrared spectra, nuclear magnetic resonance spectrum and dsc analysis, can prove and obtain purified polymer, and have higher molecular weight, percentage of grafting can be up near 100%.
With dissolution with solvents, with desk-top spreader rotary plating on substrate, (260～365nm) shine into capable photo-crosslinking with UV-light with gained photosensitive polymers material.Find that the polymkeric substance after the illumination no longer is dissolved in all kinds of SOLVENTS, it is crosslinked to illustrate that polymkeric substance may take place.C=C the absorption peak (～1630cm in the infrared spectrum of illumination front and back is found in the relatively variation of infrared spectrogram before and after the illumination
-1) reduce significantly, illustrate that photo-crosslinking has taken place position of double bond.As seen the DSC that observes illumination post polymerization thing schemes, and the vitrifying tansition temperature of illumination post polymerization thing has disappeared, and also further specifies polymkeric substance photo-crosslinking has taken place really.
Photosensitive polymers rotary plating on substrate with gained, it is crosslinked to shine into capable directional light with polarized ultraviolet, the assembling liquid crystal cell pours into liquid crystal, is placed under the polarizing microscope and observes, the visual field is even, when the rotation liquid crystal cell, can see that tangible light and shade changes, and illustrates that oriented film makes liquid crystal that directive action has taken place really, that is the various polymkeric substance of institute's synthetic of the present invention have the performance of anticipation really.
Claims (17)
1. the polymkeric substance of a tool formula (I) structure,
Wherein:
N is the integer greater than 1;
R
1And R
2Be respectively hydrogen atom, halogen, nitro, C
1-C
10Alkyl or C
1-C
10Alkoxyl group, and x and y system is respectively 1 to 3 integer, and R
1And R
2System lays respectively at ortho position, a position or the contraposition of phenyl ring; And
G system is selected from following group:
(1) Racemic glycidol ethers
-CH
2-O-R-O-CH
2-
Wherein R system is selected from group that following groups constitutes:
(a) Bisphenol F type
(b) bisphenol S type
(c) Hydrogenated Bisphenol A type
(d) halo type
(2) Racemic glycidol amine
R wherein
3Be C
1-C
6Alkyl;
(3) glycidyl ester class
(4) glycerols Resins, epoxy
(5) glycols Resins, epoxy
-CH
2-O-CH
2-CH
2-O-CH
2-；
(6) silicone based Resins, epoxy
(7) cycloaliphatic epoxy resin class
(8) acid imide Resins, epoxy
R wherein
4Be aryl.
2. polymkeric substance as claimed in claim 1, wherein each R
1Be to be respectively hydrogen, C
1-C
6Alkyl, C
1-C
6Alkoxy or halogen.
3. polymkeric substance as claimed in claim 2, wherein R
1Be be selected from adjacent methyl, an ethyl, to methoxyl group and to chloro.
4. polymkeric substance as claimed in claim 1, wherein each R
2Be to be respectively hydrogen, C
1-C
6Alkyl, C
1-C
6Alkoxy or halogen.
5. polymkeric substance as claimed in claim 4, wherein R
2Be be selected from hydrogen, neighbour-methyl ,-ethyl, right-methoxyl group and right-chloro.
6. polymkeric substance as claimed in claim 1, wherein the percentage of grafting scope of this polymkeric substance is between 50% to 100%.
7. polymkeric substance as claimed in claim 1, wherein the molecular-weight average of this polymkeric substance is between 5,000 to 200,000.
8. method for preparing polymkeric substance as claimed in claim 1, it comprises the following step:
(I) epoxy monomer and aniline monomer are carried out polycondensation, produce the prepolymer of hydroxyl, wherein epoxy monomer is to be selected from following groups:
(1) Racemic glycidol ethers
Wherein R is:
(a) Bisphenol F type
(b) bisphenol S type
(c) Hydrogenated Bisphenol A type
(d) halo type
(2) glycidyl ester class
(3) Racemic glycidol amine
R wherein
3Be C
1-C
6Alkyl;
(4) the alicyclic ring same clan
(5) acid imide
R wherein
4Have and the described identical definition of claim 1;
(6) silicone based
(7) glycerols Resins, epoxy
(8) glycols Resins, epoxy
Aniline monomer then is selected from the compound of following (II):
R wherein
2Each is selected from hydrogen atom, halogen, nitro, C respectively
1-C
10Alkyl or C
1-C
10Alkoxyl group, and y is 1 to 3 integer, and each R
2System lays respectively at ortho position, a position or the contraposition of phenyl ring; And
(II) acid absorber with cinnamyl chloride monomer, solvent and use optionally adds in the prepolymer of step (I) gained, with acquisition formula (I) polymkeric substance,
Wherein the cinnamyl chloride single mass system is selected from the compound of following formula (III)
R wherein
1Be hydrogen atom, halogen, nitro, C
1-C
10Alkyl or C
1-C
10Alkoxyl group, x are 1 to 3 integer, and each R
1System lays respectively at ortho position, a position or the contraposition of phenyl ring, and W is a halogen.
9. method as claimed in claim 8, the wherein R in the aniline compound of this formula (II)
2Be to be selected from H, C
1-C
6Alkyl, C
1-C
6Alkoxyl group and halogen.
10. method as claimed in claim 8, wherein the aniline compound of this formula (II) is to be selected from aniline, o-toluidine, m-ethyl aniline, P-nethoxyaniline and p-Chlorobenzoic acid amide.
11. method as claimed in claim 8, the wherein R in the meat etheride of this formula (III)
1Be to be selected from H, C
1-C
6Alkyl, C
1-C
6Alkoxyl group and halogen.
12. method as claimed in claim 8, wherein this cinnyl halogenide be selected from cinnamyl chloride, adjacent methyl cinnamyl chloride, an ethyl cinnamyl chloride, to the methoxyl group cinnamyl chloride and to the chloro cinnamyl chloride.
13. method as claimed in claim 8, wherein solvent is an aprotic polar solvent.
14. method as claimed in claim 13, wherein aprotic polar solvent is to be selected from tetrahydrofuran (THF), N, dinethylformamide, methyl-sulphoxide, N,N-dimethylacetamide, N-Methyl pyrrolidone or its mixture.
15. method as claimed in claim 8, wherein acid absorber is to be selected from pyridine, triethylamine, N-ethylmorpholine and xylidine, or its mixture.
16. polymkeric substance as claimed in claim 1, it is used for liquid-crystal display as the oriented layer material.
17. a liquid crystal orientation layer material, it contains polymkeric substance as claimed in claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA021538344A CN1504538A (en) | 2002-11-28 | 2002-11-28 | Liquid crystal display orientation layer material and preparing method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA021538344A CN1504538A (en) | 2002-11-28 | 2002-11-28 | Liquid crystal display orientation layer material and preparing method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1504538A true CN1504538A (en) | 2004-06-16 |
Family
ID=34235321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA021538344A Pending CN1504538A (en) | 2002-11-28 | 2002-11-28 | Liquid crystal display orientation layer material and preparing method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1504538A (en) |
-
2002
- 2002-11-28 CN CNA021538344A patent/CN1504538A/en active Pending
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