CN103113230B - Photo-sensitive monomer, liquid crystal material, liquid crystal panel and preparation method thereof, optoelectronic equipment and preparation method thereof - Google Patents
Photo-sensitive monomer, liquid crystal material, liquid crystal panel and preparation method thereof, optoelectronic equipment and preparation method thereof Download PDFInfo
- Publication number
- CN103113230B CN103113230B CN201310036025.2A CN201310036025A CN103113230B CN 103113230 B CN103113230 B CN 103113230B CN 201310036025 A CN201310036025 A CN 201310036025A CN 103113230 B CN103113230 B CN 103113230B
- Authority
- CN
- China
- Prior art keywords
- liquid crystal
- atom
- group
- follows
- photo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Abstract
A kind of photo-sensitive monomer inclusion compound IV, its chemical formulation is as follows:
" R " is " A-Sp-P " base." A " is selected from Sauerstoffatom, sulphur atom, methoxyl group, carbonyl, carboxyl, amine formyl, methylthio group, ethenecarbonyl, carbonyl vinyl and singly-bound." Sp " is spacer, and it is selected from straight chained alkyl, branched-chain alkyl and singly-bound." P " is polymerizable groups." Z " is selected from Sauerstoffatom, sulphur atom, methoxyl group, carbonyl, carboxyl, amine formyl, methylthio group, ethenecarbonyl, carbonyl vinyl and singly-bound." L
1", " L
2", " L
3", " L
4", " L
5", " L
6" the alkane carbonyl oxygen base that is independently selected from hydrogen atom, intert-gas atoms, halogen atom, cyano group, alkyl, alkyl carbonyl, carbalkoxy and there is 1 ~ 7 carbon atom wherein at least one hydrogen atom by fluorine atom or chlorine atom replace.
Description
The application is the applying date is on February 6th, 2007, and application number is: 201010556618.8, and name is called: the divisional application of the application for a patent for invention of " photo-sensitive monomer, liquid crystal material, liquid crystal panel and preparation method thereof, optoelectronic equipment and preparation method thereof ".And application number is: to be application numbers be in the application for a patent for invention of 201010556618.8: the divisional application of 200710006788.7.
Technical field
The present invention relates to a kind of optoelectronic equipment and preparation method thereof, particularly relate to and a kind ofly apply polymerization macromolecule optoelectronic equipment of assisting alignment technique and preparation method thereof.
Background technology
In recent years, liquid crystal panel develops one and is referred to as polymerization macromolecule and assists orientation (Polymer-StabilizingAlignment, PSA) alignment technique, this technology is mixed in liquid crystal layer by photo-sensitive monomer, treat its arrange after irradiating ultraviolet light, allow photo-sensitive monomer aggregate into orientation polymkeric substance, guide Liquid Crystal Molecules Alignment.
In order to shorten polymerization time, light initiator (initiator) can be mixed into again in above-mentioned liquid crystal layer, help photo-sensitive monomer rapid polymerization.But though light initiator can accelerate the time of making, but produced liquid crystal panel can produce the problem of image residue (imagesticking).That is, when switching to another image display after liquid crystal panel shows same image for a long time, image above can remain and be overlapped on subsequent images for a long time.
Summary of the invention
The object of the invention is to a kind of photo-sensitive monomer, liquid crystal material, liquid crystal panel and preparation method thereof and optoelectronic equipment and preparation method thereof, the photo-sensitive monomer added in its liquid crystal material can rapid polymerization, shortens preparation time.
The present invention proposes a kind of photo-sensitive monomer, at least one in inclusion compound I, II, III and IV, and chemical compounds I is as follows with chemical formulation:
wherein n>=3;
Compound ii is as follows with chemical formulation:
Compound III is as follows with chemical formulation:
Wherein, m >=2, n=1 ~ 5;
Compounds Ⅳ is as follows with chemical formulation:
Wherein, m >=2, n=1 ~ 5;
" R " is " A-Sp-P " base, and " R
1", " R
2, " R
3", " R
4", " R
5" and " R
6" at least two substituting groups be A-Sp-P base;
" A " is selected from Sauerstoffatom, sulphur atom, methoxyl group (methyoxy), carbonyl (carbonyl), carboxyl (caroboxyl), amine formyl (carbamoyl), methylthio group (methylthio), ethenecarbonyl (ethenylcarbonyl), carbonyl vinyl (carbonylethenyl) and singly-bound;
" Sp " is spacer, is selected from straight chained alkyl, branched-chain alkyl and singly-bound;
" P " is polymerizable groups;
" Z " is selected from Sauerstoffatom, sulphur atom, methoxyl group (methyoxy), carbonyl (carbonyl), carboxyl (caroboxyl), amine formyl (carbamoyl), methylthio group (methylthio), ethenecarbonyl (ethenylcarbonyl), carbonyl vinyl (carbonylethenyl) and singly-bound;
" L
1", " L
2", " L
3", " L
4", " L
5", " L
6", " L
7", " L
8" alkane carbonyl oxygen base (alkylcarbonyloxy) that is independently selected from hydrogen atom, intert-gas atoms, halogen atom, cyano group (cyanogroup), alkyl (alkyl), alkyl carbonyl (alkylcarbonyl), carbalkoxy (alkoxycarbonyl) and there is 1 ~ 7 carbon atom wherein at least one hydrogen atom by fluorine atom or chlorine atom replace.
The present invention also proposes a kind of liquid crystal material and comprises liquid crystal molecule and above-mentioned photo-sensitive monomer.
The present invention also proposes a kind of liquid crystal panel and comprises above-mentioned liquid crystal material, and its photo-sensitive monomer comprised is aggregated into polymeric film, to be used as alignment film.
The present invention also proposes a kind of optoelectronic equipment and comprises above-mentioned liquid crystal panel.
The present invention also proposes a kind of manufacture method of liquid crystal panel, comprises step: (a) provides a pair substrate; B () injects liquid crystal material, between this is to substrate, and liquid crystal material comprises liquid crystal molecule and above-mentioned photo-sensitive monomer; And (c) applies energy source at this to substrate, be convenient to form polymeric film at this at least one substrate in substrate, using as alignment film to be polymerized photo-sensitive monomer.
The present invention also proposes a kind of manufacture method of optoelectronic equipment, comprises the manufacture method of above-mentioned liquid crystal panel.
For foregoing of the present invention can be become apparent, a preferred embodiment cited below particularly, and coordinate institute's accompanying drawings, be described in detail below:
Accompanying drawing explanation
Figure 1A ~ 1D represents a kind of liquid crystal panel Making programme figure according to present pre-ferred embodiments.
Fig. 2 represents the schematic diagram of the optoelectronic equipment of present pre-ferred embodiments.
[major parts nomenclature]
100: liquid crystal panel
110,120: a pair substrates
130: liquid crystal molecule
140: photo-sensitive monomer
145: polymeric film
150: electronic component
200: optoelectronic equipment
Embodiment
The present invention mainly proposes a kind of photo-sensitive monomer, when it is applied to the making method of liquid crystal panel and optoelectronic equipment, can shorten polymerization time, and improve the problem of image residue.The chemical general formula of photo-sensitive monomer, preferred embodiment and synthetic method are below described, and the method being applied to by these photo-sensitive monomers and making optoelectronic equipment and liquid crystal panel is described.
Photo-sensitive monomer
The present invention mainly proposes a kind of photo-sensitive monomer, has at least two polymerizable groups in monomer whose, therefore when photo-sensitive monomer receive light stimulus carry out polyreaction time, its polymerization rate is very fast, reaches that to be polymerized required time completely also shorter.At least one in the photo-sensitive monomer inclusion compound I, II, III and IV that the present invention proposes.
Chemical compounds I is as follows with chemical formulation:
" R " is " A-Sp-P " base.
" A " is selected from Sauerstoffatom, sulphur atom, methoxyl group (methyoxy ,-OCH
2-), carbonyl (carbonyl ,-C=O-), carboxyl (caroboxyl ,-COO-), amine formyl (carbamoyl ,-CO-N
0r-,-N
0r-CO-), methylthio group (methylthio ,-SCH
2-,-CH
2s-), ethenecarbonyl (ethenylcarbonyl ,-CH=CH-COO-), carbonyl vinyl (carbonylethenyl ,-COO-CH=CH-) and singly-bound.
" Sp " is spacer, and it is selected from straight chained alkyl, branched-chain alkyl and singly-bound.It is preferred that when " SP " be selected from straight or branched alkyl time, the carbon atom number comprised between 1 ~ 8, in addition, one or two non-conterminous-CH
2-Ji is replaced by Sauerstoffatom or sulphur atom.
" P " is polymerizable groups.It is preferred that " P " is selected from acrylate-based (acrylate), methacrylate based (methacrylate), vinyl (vinyl), vinyloxy group (vinyloxy), propylene ether (propenylether), epoxy group(ing) (expoxy), group V, VI, VII, VIII and Ⅸ.Wherein " P " select be methacrylate based time, there is the fastest speed of response.
Group V is as follows with chemical formulation:
" U " is selected from hydrogen atom, methyl (methyl), fluorine atom, trifluoromethyl (trifluoromethyl ,-CF
3) and phenyl (Phenyl);
Group VI is as follows with chemical formulation:
" X " is selected from hydrogen atom, methyl (methyl), fluorine atom, trifluoromethyl (trifluoromethyl ,-CF
3) and phenyl (Phenyl);
Group VII is pyrroles-2,5-diketone (pyrrole-2,5-dione), as follows with chemical formulation:
Group VIII is as follows with chemical formulation:
" Y " is selected from hydrogen atom, methyl (methyl), fluorine atom, trifluoromethyl (trifluoromethyl ,-CF
3) and phenyl (Phenyl);
Group Ⅸ is as follows with chemical formulation:
" Q " is selected from hydrogen atom, methyl (methyl), fluorine atom, trifluoromethyl (trifluoromethyl ,-CF
3) and phenyl (Phenyl).
For elaborating for the structure of chemical compounds I and synthetic method thereof; elaborate for enumerating compound [I-1] for example below; but chemical compounds I of the present invention is not limited thereto, as long as meet above-mentioned chemical general formula and group restriction compound all belong to the present invention institute for protect scope.Chemical compounds I is such as compound [I-1], and " A " in wherein n=3, " R " (A-Sp-P) base is selected from Sauerstoffatom and " Sp " is singly-bound, and " P " is methacrylate based (methacrylate).For example, the synthesis mode of compound [I-1] is expressed as follows with chemical equation (1):
In order to synthesize the compound [I-1] as shown in chemical equation (1), first by 1 of 1 mmole, 3,5-Trihydroxyl-beneze (compound of chemical formula [1]) adds 250mL reaction unit (as: two-neck bottle or other), bleeds with deaeration in condenser de-watering apparatus.After input nitrogen three times, liquid-adding device (as: funnel or other) connects nitrogen, makes reactive system be in anaerobic anhydrous state.Then, at room temperature the tetrahydrofuran (THF) (Tetrahydrofuran, THF) of the triethylamine (triethylamine, TEA) of 3.5 mmoles and 50 milliliters after dewatering is added and be stirred to dissolving.Afterwards, inject the methacrylic chloride (methacryloylchloride) of 3.5 mmoles under ice bath, at room temperature reaction is to every other day.Then, air exhaust filtering also rinses with tetrahydrofuran (THF) (THF), collects filtrate, by its concentrating under reduced pressure, extracts by ethyl acetate (EthylAcetate, EA) and water, with magnesium sulfate (MgSO
4) dewater and air exhaust filtering, then concentrate and vacuumize, obtain yellow solid.Finally, do recrystallize with normal hexane (hexane), can obtain outward appearance is white solid, compound [I-the 1] (C of productive rate about 60%
19h
20o
5).
Compound ii is as follows with chemical formulation:
" R
1", " R
2, " R
3", " R
4", " R
5" and " R
6" at least two substituting groups be A-Sp-P base, wherein " A ", " Sp ", in " P " group and above-claimed cpd I " A ", " Sp ", " P " group feature is identical, does not repeat them here.
" L
1", " L
2", " L
3", " L
4" be selected from hydrogen atom, intert-gas atoms, halogen atom, cyano group (cyanogroup), alkyl (alkyl), alkyl carbonyl (alkylcarbonyl), carbalkoxy (alkoxycarbonyl) and there is alkane carbonyl oxygen base (alkylcarbonyloxy) of 1 ~ 7 carbon atom.Halogen atom comprises fluorine (F), chlorine (Cl), bromine (Br), iodine (I).It is preferred that the alkane carbonyl oxygen base with 1 ~ 7 carbon atom wherein at least one hydrogen atom by fluorine atom or chlorine atom replace.
For elaborating for the structure of compound ii and synthetic method thereof; below enumerate compound [II-1] for example to elaborate; but compound ii of the present invention is not limited thereto, as long as meet above-mentioned chemical general formula and group restriction compound all belong to the present invention institute for protect scope.Compound ii is such as compound [II-1], wherein " R
1", " R
2, " R
3", " R
4", " R
5" and " R
6" in " A " be Sauerstoffatom, " Sp " is selected from singly-bound, and " P " is methacrylate based (methacrylate), " L
1", " L
2", " L
3", " L
4" be all hydrogen atom.For example, the synthesis mode of compound [II-1] is expressed as follows with chemical equation (2):
In order to synthesize the compound [II-1] as shown in chemical equation (2), first by the phenanthrene-2 of 1 mmole, 3,6,7,9,10-hexaol (compound of chemical formula [2]) adds 250mL reaction unit (as: two-neck bottle or other), bleeds with deaeration in condenser de-watering apparatus.After input nitrogen three times, liquid-adding device (as: funnel or other) connects nitrogen, makes reactive system be in anaerobic anhydrous state.Then, at room temperature the tetrahydrofuran (THF) (Tetrahydrofuran, THF) of the triethylamine (triethylamine, TEA) of 6.5 mmoles and 50 milliliters after dewatering is added and be stirred to dissolving.Afterwards, inject the methacrylic chloride (methacryloylchloride) of 6.5 mmoles under ice bath, at room temperature reaction is to every other day.Then, air exhaust filtering also rinses with tetrahydrofuran (THF) (THF), collects filtrate reduced in volume, extracts, with magnesium sulfate (MgSO by ethyl acetate (EthylAcetate, EA) and water
4) dewater and air exhaust filtering, then concentrate and vacuumize, obtain yellow solid.Finally, with methylene chloride/methanol (CHC
l2/ MeOH) do recrystallize, can obtain outward appearance is white solid, compound [II-the 1] (C of productive rate about 54%
38h
34o
12).
Compound III is as follows with chemical formulation:
Wherein, m >=2, n=1 ~ 5;
" R " is " A-Sp-P " base, and it is identical with the feature of " R " group in above-claimed cpd I, does not repeat them here.
" L
1", " L
2", " L
3", " L
4", " L
5", " L
6", " L
7", " L
8" identical with the feature of " L " group in above-claimed cpd II, do not repeat them here.
" Z " is selected from Sauerstoffatom, sulphur atom, methoxyl group (methyoxy ,-OCH2-), carbonyl (carbonyl ,-C=O-), carboxyl (caroboxyl ,-COO-), amine formyl (carbamoyl ,-CO-N
0r-,-N
0r-CO-), methylthio group (methylthio ,-CH
2s-,-SCH
2-), ethenecarbonyl (ethenylcarbonyl ,-CH=CH-COO-), carbonyl vinyl (carbonylethenyl ,-COO-CH=CH-) and singly-bound.
For elaborating for the structure of compound III and synthetic method thereof; below enumerate compound [III-1] for example to elaborate; but compound III of the present invention is not limited thereto, as long as meet above-mentioned chemical general formula and group restriction compound all belong to the present invention institute for protect scope.Compound III is such as compound [III-1], wherein n=1, m=2, and " A " in " R " (A-Sp-P) is Sauerstoffatom, and " Sp " is selected from singly-bound, and " P " is methacrylate based (methacrylate), " L
1", " L
2", " L
3", " L
4", " L
5", " L
6", " L
7", " L
8" be all hydrogen atom, " Z " is singly-bound.For example, the synthesis mode of compound [III-1] is expressed as follows with chemical equation (3):
In order to synthesize the compound [III-1] as shown in chemical equation (3), first by 4 of 1 mmole, 4'-Dihydroxybiphenyl (compound of chemical formula [3]) adds in 250mL reaction unit (as: two-neck bottle or other), bleeds with deaeration in condenser de-watering apparatus.After input nitrogen three times, liquid-adding device (as: funnel or other) connects nitrogen, makes reactive system be in anaerobic anhydrous state.Then, at room temperature 3,5-bis (methacryloyloxy) benzoicacid of 2 mmoles and the methylene dichloride (dichloromethane, DCM) of 50 milliliters after dewatering are added and be stirred to dissolving.Afterwards, inject two hexamethylene carbodiimides (dicyclohexylcarbodiimide, DCC) of 2.2 mmoles under ice bath, at room temperature reaction is to every other day.Then, air exhaust filtering also rinses with methylene dichloride (DCM), collects filtrate reduced in volume, extracts, with magnesium sulfate (MgSO with methylene dichloride (DCM) and water
4) dewater and air exhaust filtering, then concentrate and vacuumize, obtain yellow solid.Finally, with methylene chloride/methanol (CHC
l2/ MeOH) do recrystallize, can obtain outward appearance is white solid, compound [III-the 1] (C of productive rate about 60%
42h
34o
12).
Compounds Ⅳ is as follows with chemical formulation:
Wherein, m >=2, n=1 ~ 5;
" R " is " A-Sp-P " base, and it is identical with the feature of " R " group in above-claimed cpd I, does not repeat them here.
" Z " is with above-claimed cpd III " Z " feature of group is identical, do not repeat them here.
" L
1", " L
2", " L
3", " L
4", " L
5", " L
6" with above-claimed cpd II " L " feature of group is identical, do not repeat them here.
For elaborating for the structure of compounds Ⅳ and synthetic method thereof; below enumerating compound [IV-1] for example elaborates; but compounds Ⅳ of the present invention is not limited thereto, as long as meet above-mentioned chemical general formula and group restriction compound all belong to the present invention institute for protect scope.Compounds Ⅳ is such as compound [IV-1], wherein n=1, m=2, and " A " in " R " (A-Sp-P) is Sauerstoffatom, and " Sp " is selected from singly-bound, and " P " is methacrylate based (methacrylate), " L
1", " L
2", " L
3", " L
4", " L
5", " L
6" be all hydrogen atom, " Z " is carboxyl (caroboxyl).For example, the synthesis mode of compound [IV-1] is expressed as follows with chemical equation (4):
[Ⅳ-1](3)
In order to synthesize the compound [IV-1] as shown in chemical equation (4), first by 2 of 1 mmole, 6-Dihydroxynaphthalene (compound of chemical formula [4]) adds in 250mL reaction unit (as: two-neck bottle or other), bleeds with deaeration in condenser de-watering apparatus.After input nitrogen three times, liquid-adding device (as: funnel or other) connects nitrogen, makes reactive system be in anaerobic anhydrous state.Then, at room temperature 3,5-bis (methacryloyloxy) benzoicacid of 2 mmoles and the methylene dichloride (dichloromethane, DCM) of 50 milliliters after dewatering are added and be stirred to dissolving.Afterwards, inject two hexamethylene carbodiimides (dicyclohexylcarbodiimide, DCC) of 2.2 mmoles under ice bath, at room temperature reaction is to every other day.Then, air exhaust filtering also rinses with methylene dichloride (DCM), collects filtrate reduced in volume, with methylene dichloride (DCM) and carry out water extraction, with magnesium sulfate (MgSO
4) dewater and air exhaust filtering, then concentrate and vacuumize, obtain yellow solid.Finally, with methylene chloride/methanol (CHC
l2/ MeOH) do recrystallize, can obtain outward appearance is white solid, compound [IV-the 1] (C of productive rate about 52%
40h
32o
12).
The application method of photo-sensitive monomer
The photo-sensitive monomer that the present invention proposes can be applicable to polymer and assists in orientation (Polymer-StabilizingAlignment, PSA) technology, in order to manufacture liquid crystal panel and/or optoelectronic equipment.Figure 1A ~ 1D represents the Making programme figure of the liquid crystal panel according to present pre-ferred embodiments.Its making method is described as follows: first, provides a pair substrate 110 and 120, as shown in Figure 1A.Then, inject liquid crystal material between this is to substrate 110 and 120, and liquid crystal material comprises liquid crystal molecule 130 and above-mentioned at least one photo-sensitive monomer 140, as shown in Figure 1B.Wherein, the method injecting liquid crystal material comprises the formula Liquid crystal pour program (OneDropFill that drips; ODF) the wherein one and in liquid crystal suction program.And liquid crystal material comprises above-mentioned at least one photo-sensitive monomer 140, and each photo-sensitive monomer 140 comprises the monomer of a kind of structure or various structures mixing.Finally, apply energy source at this at least one substrate in substrate 110 and 120, polymerization photo-sensitive monomer 140 is made to be convenient to form polymeric film 145 at this at least one each substrate in substrate, to be used as alignment film, preferably, polymeric film 145 is described as shown in figure ip at this on substrate, but is not limited thereto.Energy source is such as visible light source, ultraviolet source or other can cause the light source of the photo-sensitive monomer polyreaction of the present embodiment.
To increase orientation effect, first can form another alignment film at this at least one substrate in substrate, be such as that substrate 110 comprises alignment film 112 and substrate 120 comprises alignment film 122, as shown in Figure 1A, again at the polymeric film 145 (as: the second alignment film) that the upper formation of this alignment film (as: the first alignment film) is above-mentioned, orientation effect can be promoted further.Wherein, the alignment method of another alignment film comprises in the mode of traditional brushing and with at least one in the mode of rayed orientation.
Liquid crystal material comprises liquid crystal molecule 130 and above-mentioned at least one photo-sensitive monomer 140, as shown in Figure 1B.Moreover, liquid crystal material, preferably, at least one more in inclusion compound Ⅹ and compound Ⅹ I, but be not limited to this, liquid crystal material also can not comprise at least one in above-claimed cpd Ⅹ and compound Ⅹ I or comprise other compound that can coordinate with the photo-sensitive monomer described in the above embodiment of the present invention.And with compound Ⅹ 2.6-naphthalene-dimethacrylate in this way joined together by embodiments of the invention, compound Ⅹ I in this way 4,4'-biphenylene-dimethacrylate, its chemical formula is expressed as follows respectively:
The content of at least one in compound Ⅹ and compound Ⅹ I, preferably, different from the content of at least one in chemical compounds I, II, III and IV, but, be not limited to this, also can the content of at least one in compound Ⅹ and compound Ⅹ I identical with the content of at least one in chemical compounds I, II, III and IV.
In order to help at least one disturbance in liquid crystal molecule 130 and photo-sensitive monomer 140, preferably, as shown in Figure 1 C, apply at least one in voltage and thermal source at this at least one substrate in substrate 110 and 120, to help at least one disturbance in liquid crystal molecule 130 and photo-sensitive monomer 140.At least one in above-mentioned thermal source and voltage can repeatedly apply or once apply.When repeatedly applying, at least one in above-mentioned thermal source and voltage is temperature or magnitude of voltage are identical or different in fact each time.In addition, the kenel of voltage comprises direct current, alternating-current or its combination.For example, when liquid crystal molecule 130 is subject to voltage driven and rotates, liquid crystal molecule can arrange as shown in Figure 1 C with photo-sensitive monomer rotates, but is not limited to this, also can not apply at least one in thermal source and voltage at upper substrate 110 and hypocoxa 120, and directly carry out next program.
Please refer to Fig. 2, it represents the schematic diagram of the optoelectronic equipment of preferred embodiment of the present invention.As shown in Figure 2, an optoelectronic equipment 200 can be combined into electronic component 150 by the display panels 100 described in above-described embodiment.Electronic component 150 comprise as: controlling elements, operating component, processing element, input element, storage element, driving element, luminous element, protection element, sensing element, detecing element or other functional element or its combination.And the type of optoelectronic equipment comprises the panel etc. in portable product (as mobile phone, Kamera, photographic camera, mobile computer, game machine, wrist-watch, music player, electronic mail transceiver, map navigator, digital photo or analogous products), video and audio product (as audio and video player or analogous products), screen, TV, billboard, projector.Moreover the type of the display panel of the above embodiment of the present invention, classifies with at least one in the kenel of the kenel of its pixel electrode and liquid crystal molecule, comprises penetrating type, semi penetration type, reflection-type, vertical orientation type (VA), horizontal cutting is remodeled (IPS), multi-domain perpendicular alignment-type (MVA), twisted nematic (TN), super-twist nematic (STN), pattern vertical orientation type (PVA), super pattern vertical orientation type (S-PVA), advanced person is type (ASV) with great visual angle, fringe field switch type (FFS), continuous fireworks shape arrange type (CPA), rotational symmetry arrangement micella type (ASM), optical compensation curved arrange type (OCB), super horizontal cutting remodels (S-IPS), advanced super horizontal cutting remodels (AS-IPS), extreme edge electric field switch type (UFFS), stabilizing polymer alignment-type, double vision angle-style (dual-view), three visual angle types (triple-view), or other profile plate, or its combination.
The optoelectronic equipment of the liquid crystal panel of the photo-sensitive monomer disclosed in the above embodiment of the present invention, liquid crystal material, application photo-sensitive monomer and manufacture method thereof, application photo-sensitive monomer and manufacture method thereof, have multiple advantages and comprise:
1. polyreaction is fast.The photo-sensitive monomer of the above embodiment of the present invention has multiple (at least two) polymerizable groups, therefore when photo-sensitive monomer receive light stimulus carry out polyreaction time, its polymerization rate is very fast, reaches that to be polymerized required time completely also shorter.In addition, compared to utilizing light initiator to accelerate the mode of polyreaction traditionally, the above embodiment of the present invention utilizes the mode increasing reactive group density to improve collision probability, can accelerate the problem that polyreaction but can not produce image residue.
2. polymerization efficiency is high.The intercalated nucleus structure of the photo-sensitive monomer of the above embodiment of the present invention has strong absorption peak at 300-400nm, the UV light source using 365nm in existing preparation technology can be met, therefore can effectively absorb UV light and by energy trasfer to reactive group, improve polymerization efficiency.
3. the power of putting in order of pair liquid crystal molecule is strong.Because the intercalated nucleus of the photo-sensitive monomer of the above embodiment of the present invention is all coplanar structure, photo-sensitive monomer can be increased power is put in order to liquid crystal molecule.
4. do not affect display photochromic.The intercalated nucleus structure of the photo-sensitive monomer of the above embodiment of the present invention has strong absorption peak at 300-400nm, due to fluorescence is more weak or wavelength of giving out light at below 400nm, therefore after connecting reactive group, fluorescence can be effectively suppressed.That is, the polymeric film in liquid crystal layer can't produce the doubt of color or luminescence.Thus, the present embodiment uses polymeric film as the liquid crystal panel of alignment film or optoelectronic equipment when show image, and its display color and efficiency can maintain previous level, and can not be affected.
Claims (12)
1. a photo-sensitive monomer, inclusion compound IV, compounds Ⅳ is as follows with chemical formulation:
Wherein, m >=2, n=1 ~ 5;
" R " is " A-Sp-P " base;
" A " is selected from Sauerstoffatom, sulphur atom ,-OCH
2-, carbonyl ,-COO-, amine formyl ,-SCH
2-,-CH
2s-and singly-bound;
" Sp " is spacer, and it is selected from straight-chain alkyl-sub-, branched alkylidene and singly-bound, and the carbon atom number comprised is between 1 ~ 8;
" P " is polymerizable groups, and it is selected from acrylate-based, methacrylate based, vinyl, vinyloxy group, propylene ether, epoxy group(ing), group V, VI, VII, VIII and Ⅸ;
Group V is as follows with chemical formulation:
" U " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl;
Group VI is as follows with chemical formulation:
" X " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl;
Group VII is as follows with chemical formulation:
Group VIII is as follows with chemical formulation:
" Y " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl;
Group Ⅸ is as follows with chemical formulation:
" Q " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl;
" Z " is selected from Sauerstoffatom, sulphur atom ,-OCH
2-, carbonyl ,-COO-, amine formyl ,-SCH
2-,-CH
2s-and singly-bound;
" L
1", " L
2", " L
3", " L
4", " L
5", " L
6" the alkane carbonyl oxygen base that is independently selected from hydrogen atom, halogen atom, cyano group, alkyl, alkyl carbonyl, carbalkoxy and there is 1 ~ 7 carbon atom wherein at least one hydrogen atom by fluorine atom or chlorine atom replace.
2. a liquid crystal material, comprises liquid crystal molecule and photo-sensitive monomer as claimed in claim 1.
3. liquid crystal material as claimed in claim 2, is characterized in that also comprising: at least one in compound Ⅹ and compound Ⅹ I, and the representative of its chemical formula is as follows:
4. liquid crystal material as claimed in claim 3, is characterized in that the content of at least one in compounds X and compound Ⅹ I is different from the content of at least one in compounds Ⅳ.
5. a liquid crystal panel, comprises liquid crystal material as claimed in claim 2, and its photo-sensitive monomer comprised is aggregated into polymeric film, to be used as alignment film.
6. an optoelectronic equipment, comprises liquid crystal panel as claimed in claim 5.
7. a manufacture method for liquid crystal panel, comprises step as follows:
A pair substrate is provided;
Inject liquid crystal material, between this is to substrate, and this liquid crystal material comprises liquid crystal molecule and photo-sensitive monomer, and this photo-sensitive monomer comprises one or more compounds Ⅳs,
Compounds Ⅳ is as follows with chemical formulation:
Wherein, m >=2, n=1 ~ 5;
" R " is " A-Sp-P " base;
" A " is selected from Sauerstoffatom, sulphur atom ,-OCH
2-, carbonyl ,-COO-, amine formyl ,-SCH
2-,-CH
2s-and singly-bound;
" Sp " is spacer, and it is selected from straight-chain alkyl-sub-, branched alkylidene and singly-bound, and the carbon atom number comprised is between 1 ~ 8;
" P " is polymerizable groups, and it is selected from acrylate-based, methacrylate based, vinyl, vinyloxy group, propylene ether, epoxy group(ing), group V, VI, VII, VIII and Ⅸ;
Group V is as follows with chemical formulation:
" U " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl;
Group VI is as follows with chemical formulation:
" X " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl;
Group VII is as follows with chemical formulation:
Group VIII is as follows with chemical formulation:
" Y " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl;
Group Ⅸ is as follows with chemical formulation:
" Q " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl;
" Z " is selected from Sauerstoffatom, sulphur atom ,-OCH
2-, carbonyl ,-COO-, amine formyl ,-SCH
2-,-CH
2s-and singly-bound;
" L
1", " L
2", " L
3", " L
4", " L
5", " L
6" the alkane carbonyl oxygen base that is independently selected from hydrogen atom, halogen atom, cyano group, alkyl, alkyl carbonyl, carbalkoxy and there is 1 ~ 7 carbon atom wherein at least one hydrogen atom by fluorine atom or chlorine atom replace; And
Apply energy source at this on substrate, be convenient to form polymeric film at this at least one substrate in substrate, to be used as alignment film to be polymerized this photo-sensitive monomer.
8. method as claimed in claim 7, is characterized in that also comprising and applies at least one in voltage and thermal source at this on substrate.
9. method as claimed in claim 7, is characterized in that this liquid crystal material, at least one in inclusion compound Ⅹ and compound Ⅹ I:
10. method as claimed in claim 9, is characterized in that the content of at least one in compounds X and compound Ⅹ I is different from the content of compounds Ⅳ.
11. methods as claimed in claim 7, is characterized in that also comprising and form another alignment film in this at least one substrate in substrate, with to increase by this photo-sensitive monomer form the orientation effect of this alignment film.
The manufacture method of 12. 1 kinds of optoelectronic equipments, comprises the manufacture method of liquid crystal panel as claimed in claim 7.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310036025.2A CN103113230B (en) | 2007-02-06 | 2007-02-06 | Photo-sensitive monomer, liquid crystal material, liquid crystal panel and preparation method thereof, optoelectronic equipment and preparation method thereof |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310036025.2A CN103113230B (en) | 2007-02-06 | 2007-02-06 | Photo-sensitive monomer, liquid crystal material, liquid crystal panel and preparation method thereof, optoelectronic equipment and preparation method thereof |
| CN2007100067887A CN101008784B (en) | 2007-02-06 | 2007-02-06 | Photosensitive monomer, liquid crystal material, liquid crystal panel and manufacture method, and photoelectric equipment and manufacture method thereof |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2007100067887A Division CN101008784B (en) | 2007-02-06 | 2007-02-06 | Photosensitive monomer, liquid crystal material, liquid crystal panel and manufacture method, and photoelectric equipment and manufacture method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103113230A CN103113230A (en) | 2013-05-22 |
| CN103113230B true CN103113230B (en) | 2015-11-11 |
Family
ID=38697272
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310036025.2A Expired - Fee Related CN103113230B (en) | 2007-02-06 | 2007-02-06 | Photo-sensitive monomer, liquid crystal material, liquid crystal panel and preparation method thereof, optoelectronic equipment and preparation method thereof |
| CN2007100067887A Expired - Fee Related CN101008784B (en) | 2007-02-06 | 2007-02-06 | Photosensitive monomer, liquid crystal material, liquid crystal panel and manufacture method, and photoelectric equipment and manufacture method thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2007100067887A Expired - Fee Related CN101008784B (en) | 2007-02-06 | 2007-02-06 | Photosensitive monomer, liquid crystal material, liquid crystal panel and manufacture method, and photoelectric equipment and manufacture method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (2) | CN103113230B (en) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009118086A1 (en) | 2008-03-25 | 2009-10-01 | Merck Patent Gmbh | Liquid crystal display |
| US8663497B2 (en) * | 2009-11-18 | 2014-03-04 | Adeka Corporation | Liquid crystal composition comprising polymerizable compound, and liquid crystal display element using said liquid crystal composition |
| CN102219876B (en) * | 2010-04-14 | 2014-09-24 | 统炀企业有限公司 | Macromolecular liquid crystal alignment polymer and method for manufacturing liquid crystal display device by utilizing same |
| US9217109B2 (en) * | 2010-07-22 | 2015-12-22 | Merck Patent Gmbh | Polymer-stabilised liquid-crystal media and displays |
| WO2012017882A1 (en) | 2010-08-03 | 2012-02-09 | シャープ株式会社 | Liquid-crystal display device and process for producing liquid-crystal display device |
| WO2012017884A1 (en) | 2010-08-03 | 2012-02-09 | シャープ株式会社 | Liquid crystal display device and process for producing liquid crystal display device |
| US9164326B2 (en) | 2010-08-03 | 2015-10-20 | Sharp Kabushiki Kaisha | Liquid crystal display device and process for producing liquid crystal display device |
| US20130135570A1 (en) * | 2010-08-03 | 2013-05-30 | Toyo Gosei Co., Ltd. | Composition for forming liquid crystal layer, liquid crystal display device, and method for producing liquid crystal display device |
| JP5750111B2 (en) | 2010-09-07 | 2015-07-15 | シャープ株式会社 | Liquid crystal layer and polymer layer forming composition, and liquid crystal display device |
| WO2012077668A1 (en) | 2010-12-06 | 2012-06-14 | シャープ株式会社 | Liquid crystal display device and method for producing liquid crystal display device |
| WO2012077644A1 (en) * | 2010-12-07 | 2012-06-14 | シャープ株式会社 | Liquid crystal display device and method for manufacturing liquid crystal display device |
| US9239493B2 (en) | 2010-12-22 | 2016-01-19 | Sharp Kabushiki Kaisha | Liquid crystal alignment agent, liquid crystal display, and method for manufacturing liquid crystal display |
| US9036119B2 (en) * | 2011-03-09 | 2015-05-19 | Sharp Kabushiki Kaisha | Liquid crystal composition, liquid crystal display device, and method for producing liquid crystal display device |
| EP2508588B1 (en) * | 2011-04-07 | 2015-02-11 | Merck Patent GmbH | Liquid-crystalline medium and liquid-crystal display |
| CN102660299B (en) * | 2012-04-28 | 2015-02-04 | 深圳市华星光电技术有限公司 | Liquid crystal medium mixture and liquid crystal display using same |
| CN102660300B (en) * | 2012-04-28 | 2014-02-12 | 深圳市华星光电技术有限公司 | Liquid crystal medium composite as well as liquid crystal display using same and manufacturing method of liquid crystal medium composite |
| CN102786936B (en) * | 2012-05-09 | 2015-03-25 | 深圳市华星光电技术有限公司 | Liquid crystal medium composition |
| JP6343902B2 (en) * | 2013-10-16 | 2018-06-20 | Jnc株式会社 | Polymerizable compound, polymerizable composition, and liquid crystal display device |
| JP6965538B2 (en) * | 2017-03-17 | 2021-11-10 | 三菱ケミカル株式会社 | Liquid crystal composition and liquid crystal element |
| CN107290891B (en) * | 2017-05-25 | 2023-08-04 | 菏泽学院 | Viewing angle continuously controllable display |
| JP6507404B2 (en) * | 2018-02-14 | 2019-05-08 | Jnc株式会社 | Polymerizable compound, polymerizable composition and liquid crystal display device |
| TWI704393B (en) * | 2019-04-29 | 2020-09-11 | 友達光電股份有限公司 | Display apparatus |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1693970A (en) * | 2005-03-24 | 2005-11-09 | 友达光电股份有限公司 | Liquid crystal turning additive, liquid crystal display device containing it and manufacturing method |
| CN1903826A (en) * | 2006-08-11 | 2007-01-31 | 友达光电股份有限公司 | Monomer and method of manufacturing liquid crystal display panel using same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100334493C (en) * | 2004-05-28 | 2007-08-29 | 友达光电股份有限公司 | Monomer for stabilizing orientation of polymer and liquid crystal display panel with polymer therefrom |
| CN1903827A (en) * | 2006-08-11 | 2007-01-31 | 友达光电股份有限公司 | Monomer and method of manufacturing liquid crystal display panel using same |
-
2007
- 2007-02-06 CN CN201310036025.2A patent/CN103113230B/en not_active Expired - Fee Related
- 2007-02-06 CN CN2007100067887A patent/CN101008784B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1693970A (en) * | 2005-03-24 | 2005-11-09 | 友达光电股份有限公司 | Liquid crystal turning additive, liquid crystal display device containing it and manufacturing method |
| CN1903826A (en) * | 2006-08-11 | 2007-01-31 | 友达光电股份有限公司 | Monomer and method of manufacturing liquid crystal display panel using same |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103113230A (en) | 2013-05-22 |
| CN101008784B (en) | 2011-01-12 |
| CN101008784A (en) | 2007-08-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103113230B (en) | Photo-sensitive monomer, liquid crystal material, liquid crystal panel and preparation method thereof, optoelectronic equipment and preparation method thereof | |
| US7820070B2 (en) | Photosensitive monomer, liquid crystal material having the same, liquid crystal panel and method for manufacturing thereof by incorporating the same, and electro-optical device and method for manufacturing thereof by incorporating the same | |
| CN101013262B (en) | Photo-sensitive monomer, liquid crystal material, liquid crystal panel and method of fabrication, photoelectric device and fabricating method thereof | |
| EP1945737B1 (en) | Copolymer for liquid crystal alignment, liquid crystal aligning layer including copolymer for liquid crystal alignment, and liquid crystal display including liquid crystal aligning layer | |
| WO2017181466A1 (en) | Liquid crystal material, liquid crystal display panel manufacturing method, and liquid crystal display panel | |
| EP0763552B1 (en) | Curable, photoactive polymeric materials | |
| CN104685415B (en) | Image display device | |
| KR20190074987A (en) | Liquid crystal composition and liquid crystal display element | |
| KR20190130675A (en) | Manufacturing method for substrate having liquid crystal alignment film for in-plane switching-type liquid crystal display element | |
| EP2433923B1 (en) | Chlorobenzene derivative, optically isotropic liquid crystal medium, and optical element | |
| TW201837556A (en) | Liquid crystal display device and method for manufacturing the same | |
| JP2017133038A (en) | Polymer/liquid crystal composite | |
| CN103254356B (en) | Polymerizable mixture and liquid-crystal composition thereof | |
| CN106085464A (en) | Alignment film material, the manufacture method of display panels and display panels | |
| CN103906824A (en) | Optically isotropic liquid crystal medium and optical device | |
| CN110343082A (en) | A kind of dibenzofurans class can poly- property compound and its application | |
| CN103087725A (en) | Liquid crystal composition, polymer/liquid crystal composite, liquid crystal element, and liquid crystal display device | |
| CN101144944A (en) | Liquid crystal mixture for macromolecule orientation working procedure and liquid crystal display device | |
| CN106047371A (en) | Liquid crystal aligning agent, liquid crystal aligning film, and liqud crystal element | |
| WO2012017885A1 (en) | Composition for forming liquid crystal layer, liquid crystal display device, and method for producing liquid crystal display device | |
| CN102701983B (en) | Monomer and apply it and manufacture the method for display panels | |
| KR20070021258A (en) | Polymerizable liquid crystal composition and optically anisotropic body | |
| CN106433492A (en) | Lateral light-shading glue and frameless display device | |
| CN103013533B (en) | Liquid crystal composition, liquid crystal oriented mixture and liquid crystal panel | |
| CN102126948A (en) | Light sensitive monomer, liquid crystal material, liquid crystal display panel and manufacturing method thereof, and photoelectronic device and manufacturing method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20151111 Termination date: 20210206 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |