CN103113230A - Photosensitive monomer, liquid crystal material, liquid crystal panel and manufacturing method thereof, photoelectric device and manufacturing method thereof - Google Patents
Photosensitive monomer, liquid crystal material, liquid crystal panel and manufacturing method thereof, photoelectric device and manufacturing method thereof Download PDFInfo
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- CN103113230A CN103113230A CN2013100360252A CN201310036025A CN103113230A CN 103113230 A CN103113230 A CN 103113230A CN 2013100360252 A CN2013100360252 A CN 2013100360252A CN 201310036025 A CN201310036025 A CN 201310036025A CN 103113230 A CN103113230 A CN 103113230A
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- 0 C1*C=**C1 Chemical compound C1*C=**C1 0.000 description 5
- ZQVIPJFUZJLUIL-UHFFFAOYSA-N Oc(cc(c(c(c(O)c1O)c2)cc(O)c2O)c1c1)c1O Chemical compound Oc(cc(c(c(c(O)c1O)c2)cc(O)c2O)c1c1)c1O ZQVIPJFUZJLUIL-UHFFFAOYSA-N 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N Oc1cc(O)cc(O)c1 Chemical compound Oc1cc(O)cc(O)c1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
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Abstract
A photosensitive monomer comprises a compound IV, and the chemical formula of the compound IV is as shown below: 'R' represents an 'A-Sp-P' group. 'A' is selected from oxygen atom, sulfur atom, methoxyl, carbonyl, carboxyl, carbamoyl, methylthio, ethylene carbonyl, carbonyl vinyl and single bond. 'Sp' is a partition group selected from linear alkyl, branched alkyl and single bond. 'P' is a polymerizable group. 'Z' is selected from oxygen atom, sulfur atom, methoxyl, carbonyl, carboxyl, carbamoyl, methylthio, ethylene carbonyl, carbonyl vinyl and single bond. 'L1', 'L2', 'L3', 'L4', 'L5' and 'L6' are independently selected from hydrogen atom, inert gas atom, halogen atom, cyan, alkyl, alkyl carbonyl, carbalkoxy, and alkyl oxo-carbonyl, wherein at least one hydrogen atom is substituted by fluorine atom or chlorine atom.
Description
The application is to be on February 6th, 2007 applying date, and application number is: 201010556618.8, and name is called: the dividing an 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: 201010556618.8 application for a patent for invention is that application number is: 200710006788.7 divide an application.
Technical field
The present invention relates to a kind of optoelectronic equipment and preparation method thereof, particularly relate to a kind of optoelectronic equipment of using the auxiliary alignment technique of polymerization macromolecule and preparation method thereof.
Background technology
In recent years, liquid crystal panel develops a kind of auxiliary orientation (Polymer-Stabilizing Alignment of polymerization macromolecule that is referred to as, PSA) alignment technique, this technology is that photo-sensitive monomer is sneaked in liquid crystal layer, treat that it arranges irradiating ultraviolet light afterwards, allow photo-sensitive monomer aggregate into the orientation polymkeric substance, the guiding Liquid Crystal Molecules Alignment.
In order to shorten polymerization time, can sneak into again light initiator (initiator) in above-mentioned liquid crystal layer, help the photo-sensitive monomer rapid polymerization.Yet though light initiator can accelerate the time of making, still produced liquid crystal panel can produce the problem of image residue (image sticking).That is to say, when liquid crystal panel is long-time when switching to another image display after showing same image, the image of front can be long-time residual and be overlapped on follow-up image.
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 that adds in its liquid crystal material can rapid polymerization, shortens preparation time.
The present invention proposes a kind of photo-sensitive monomer, and at least a in inclusion compound I, II, III and IV, chemical compounds I is as follows with chemical formulation:
Compound ii is as follows with chemical formulation:
The 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" reach " R
6" at least two substituting groups be the A-Sp-P base;
" A " is selected from Sauerstoffatom, sulphur atom, methoxyl group (methyoxy), carbonyl (carbonyl), carboxyl (caroboxyl), amine formyl (carbamoyl), methylthio group (methylthio), ethene carbonyl (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), ethene carbonyl (ethenylcarbonyl), carbonyl vinyl (carbonylethenyl) and singly-bound;
" L
1", " L
2", " L
3", " L
4", " L
5", " L
6", " L
7", " L
8" the alkane carbonyl oxygen base (alkylcarbonyloxy) that independently is selected from hydrogen atom, intert-gas atoms, halogen atom, cyano group (cyano group), alkyl (alkyl), alkyl carbonyl (alkylcarbonyl), carbalkoxy (alkoxycarbonyl) and has 1 ~ 7 carbon atom wherein at least one hydrogen atom replaced by fluorine atom or chlorine atom.
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 that comprises 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 pair of substrate (a) is provided; (b) inject liquid crystal material, between this is to substrate, and liquid crystal material comprises liquid crystal molecule and above-mentioned photo-sensitive monomer; And (c) apply energy source at this to substrate, with the polymerization photo-sensitive monomer be convenient to form polymeric film this at least one substrate in substrate on, with as alignment film.
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 appended graphicly, be described in detail below:
Description of drawings
Figure 1A～1D represents to make schema according to a kind of liquid crystal panel of preferred embodiment of the present invention.
Fig. 2 represents the schematic diagram of the optoelectronic equipment of preferred embodiment of the present invention.
[major parts nomenclature]
100: liquid crystal panel
110,120: a pair of substrate
130: liquid crystal molecule
140: photo-sensitive monomer
145: polymeric film
150: electronic component
200: optoelectronic equipment
Embodiment
The present invention 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.Chemical general formula, preferred embodiment and the synthetic method of photo-sensitive monomer below are described, and the method that these photo-sensitive monomers are applied to make optoelectronic equipment and liquid crystal panel is described.
Photo-sensitive monomer
The present invention proposes a kind of photo-sensitive monomer, has at least two polymerizable groups in monomer whose, and therefore when polyreaction was carried out in photo-sensitive monomer reception light stimulus, its polymerization rate was very fast, reaches complete polymerization required time also shorter.At least a in 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-), the ethene carbonyl (ethenylcarbonyl ,-CH=CH-COO-), the 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.Preferably, when " SP " when being selected from the straight or branched alkyl, the carbon atom number that comprises between 1～8, in addition, one or two non-conterminous-CH
2-Ji is replaced by Sauerstoffatom or sulphur atom.
" P " is polymerizable groups.Preferably, " P " is selected from acrylate-based (acrylate), methacrylate based (methacrylate), vinyl (vinyl), vinyloxy group (vinyloxy), propylene ether (propenyl ether), epoxy group(ing) (expoxy), group V, VI, VII, VIII and IX.Wherein " P " select be methacrylate based the time, have the fastest speed of response.
The 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);
The 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);
The group VII is pyrroles-2, and 5-diketone (pyrrole-2,5-dione) is as follows with chemical formulation:
The 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);
The 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 structure and synthetic method thereof for chemical compounds I elaborate; below elaborate for example for enumerating compound [I-1]; yet chemical compounds I of the present invention is not limited thereto, so long as meet the scope that the compound of above-mentioned chemical general formula and group restriction all belongs to institute of the present invention wish protection.Chemical compounds I is for example compound [I-1], and n=3 wherein, " R " (A-Sp-P) " A " in base are selected from Sauerstoffatom and " Sp " is singly-bound, and " P " is methacrylate based (methacrylate).For instance, the synthesis mode of compound [I-1] is expressed as follows with chemical equation (1):
For synthetic compound [I-1] as shown in chemical equation (1), at first with 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 the deaeration in condenser de-watering apparatus.After input nitrogen three times, connect nitrogen on liquid-adding device (as: funnel or other), make reactive system be in the anaerobic anhydrous state.Then, at room temperature with the triethylamine (triethylamine, TEA) of 3.5 mmoles and the tetrahydrofuran (THF) (Tetrahydrofuran, THF) of 50 milliliters after dewatering add and be stirred to dissolving.Afterwards, inject the methacrylic chloride (methacryloyl chloride) 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, with its concentrating under reduced pressure, extracts with ethyl acetate (Ethyl Acetate, EA) and water, with sal epsom (MgSO
4) dewater and air exhaust filtering, then concentrated vacuumizing, get yellow solid.At last, (hexane) does recrystallize with normal hexane, and can obtain outward appearance is white solid, and productive rate is 60% compound [I-1] (C approximately
19H
20O
5).
Compound ii is as follows with chemical formulation:
" R
1", " R
2, " R
3", " R
4", " R
5" reach " R
6" at least two substituting groups be the A-Sp-P base, wherein " A ", " Sp " is 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 (cyano group), alkyl (alkyl), alkyl carbonyl (alkylcarbonyl), carbalkoxy (alkoxycarbonyl) and have the alkane carbonyl oxygen base (alkylcarbonyloxy) of 1 ~ 7 carbon atom.Halogen atom comprises fluorine (F), chlorine (Cl), bromine (Br), iodine (I).Preferably, the alkane carbonyl oxygen base that has 1 ~ 7 carbon atom wherein at least one hydrogen atom is replaced by fluorine atom or chlorine atom.
For structure and synthetic method thereof for compound ii elaborate; below to enumerate compound [II-1] to elaborate for example; yet compound ii of the present invention is not limited thereto, so long as meet the scope that the compound of above-mentioned chemical general formula and group restriction all belongs to institute of the present invention wish protection.Compound ii is for example compound [II-1], wherein " R
1", " R
2, " R
3", " R
4", " R
5" reach " R
6" in " A " be Sauerstoffatom, " Sp " is selected from singly-bound, " P " is methacrylate based (methacrylate), " L
1", " L
2", " L
3", " L
4" be all hydrogen atom.For instance, the synthesis mode of compound [II-1] is expressed as follows with chemical equation (2):
For synthetic compound [II-1] as shown in chemical equation (2), at first with 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 the deaeration in condenser de-watering apparatus.After input nitrogen three times, connect nitrogen on liquid-adding device (as: funnel or other), make reactive system be in the anaerobic anhydrous state.Then, at room temperature with the triethylamine (triethylamine, TEA) of 6.5 mmoles and the tetrahydrofuran (THF) (Tetrahydrofuran, THF) of 50 milliliters after dewatering add and be stirred to dissolving.Afterwards, inject the methacrylic chloride (methacryloyl chloride) 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 decompression and concentrates, and extracts with ethyl acetate (Ethyl Acetate, EA) and water, with sal epsom (MgSO
4) dewater and air exhaust filtering, then concentrated vacuumizing, get yellow solid.At last, with methylene chloride/methanol (CHC
l2/ MeOH) do recrystallize, can obtain outward appearance is white solid, productive rate is 54% compound [II-1] (C approximately
38H
34O
12).
The 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 the 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 the above-claimed cpd II, do not repeat them here.
" Z " be 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-), the ethene carbonyl (ethenylcarbonyl ,-CH=CH-COO-), the carbonyl vinyl (carbonylethenyl ,-COO-CH=CH-) and singly-bound.
For structure and synthetic method thereof for the compound III elaborate; below to enumerate compound [III-1] to elaborate for example; yet compound III of the present invention is not limited thereto, so long as meet the scope that the compound of above-mentioned chemical general formula and group restriction all belongs to institute of the present invention wish protection.The compound III is for example compound [III-1], and n=1 wherein, m=2, " R " " A " in (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 instance, the synthesis mode of compound [III-1] is expressed as follows with chemical equation (3):
For synthetic compound [III-1] as shown in chemical equation (3), at first with 4 of 1 mmole, 4'-Dihydroxybiphenyl (compound of chemical formula [3]) adds in 250mL reaction unit (as: two-neck bottle or other), bleeds with the deaeration in condenser de-watering apparatus.After input nitrogen three times, connect nitrogen on liquid-adding device (as: funnel or other), make reactive system be in the anaerobic anhydrous state.Then, at room temperature with 3 of 2 mmoles, 5-bis (methacryloyloxy) benzoic acid and dewater after the methylene dichloride (dichloromethane, DCM) of 50 milliliters add 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 decompression and concentrates, and extracts with methylene dichloride (DCM) and water, with sal epsom (MgSO
4) dewater and air exhaust filtering, then concentrated vacuumizing, get yellow solid.At last, with methylene chloride/methanol (CHC
l2/ MeOH) do recrystallize, can obtain outward appearance is white solid, productive rate is 60% compound [III-1] (C approximately
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 the above-claimed cpd I, does not repeat them here.
In " Z " and 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 the above-claimed cpd II in " L " feature of group is identical, do not repeat them here.
For structure and synthetic method thereof for compounds Ⅳ elaborate; below enumerating compound [IV-1] elaborates for example; yet compounds Ⅳ of the present invention is not limited thereto, so long as meet the scope that the compound of above-mentioned chemical general formula and group restriction all belongs to institute of the present invention wish protection.Compounds Ⅳ is for example compound [IV-1], and n=1 wherein, m=2, " R " " A " in (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 instance, the synthesis mode of compound [IV-1] is expressed as follows with chemical equation (4):
[Ⅳ-1] (3)
For synthetic compound [IV-1] as shown in chemical equation (4), at first with 2 of 1 mmole, 6-Dihydroxynaphthalene (compound of chemical formula [4]) adds in 250mL reaction unit (as: two-neck bottle or other), bleeds with the deaeration in condenser de-watering apparatus.After input nitrogen three times, connect nitrogen on liquid-adding device (as: funnel or other), make reactive system be in the anaerobic anhydrous state.Then, at room temperature with 3 of 2 mmoles, 5-bis (methacryloyloxy) benzoic acid and dewater after the methylene dichloride (dichloromethane, DCM) of 50 milliliters add 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 decompression concentrated, with methylene dichloride (DCM) and carry out the water extraction, with sal epsom (MgSO
4) dewater and air exhaust filtering, then concentrated vacuumizing, get yellow solid.At last, with methylene chloride/methanol (CHC
l2/ MeOH) do recrystallize, can obtain outward appearance is white solid, productive rate is 52% compound [IV-1] (C approximately
40H
32O
12).
The application method of photo-sensitive monomer
The photo-sensitive monomer that the present invention proposes can be applicable in auxiliary orientation (Polymer-Stabilizing Alignment, the PSA) technology of polymer, in order to make liquid crystal panel and/or optoelectronic equipment.Figure 1A～1D represents the making schema according to the liquid crystal panel of preferred embodiment of the present invention.Its making method is described as follows: at first, provide a pair of 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 a photo-sensitive monomer 140, as shown in Figure 1B.Wherein, the method for injection liquid crystal material comprises formula Liquid crystal pour program (the One Drop Fill that drips; ODF) wherein a kind of and in liquid crystal suction program.And liquid crystal material comprises above-mentioned at least a photo-sensitive monomer 140, and each photo-sensitive monomer 140 comprises the monomer of a kind of structure or various structures mixing.At last, apply energy source this at least one substrate in substrate 110 and 120 on, make polymerization photo-sensitive monomer 140 be convenient to form polymeric film 145 this at least one each substrate in substrate on, to be used as alignment film, preferably, illustrate as shown in Fig. 1 D polymeric film 145 this to substrate on, but be not limited to this.Energy source is for example that visible light source, ultraviolet source or other can cause the light source of the photo-sensitive monomer polyreaction of the present embodiment.
If increase the orientation effect, can first form another alignment film this at least one substrate in substrate on, for example that substrate 110 comprises alignment film 112 and substrate 120 comprises alignment film 122, as shown in Figure 1A, at the above-mentioned polymeric film 145 (as: the second alignment film) of the upper formation of this alignment film (as: the first alignment film), can promote further the orientation effect again.Wherein, the alignment method of another alignment film comprises with the mode of traditional brushing and at least a with in the mode of rayed orientation.
Liquid crystal material comprises liquid crystal molecule 130 and above-mentioned at least a photo-sensitive monomer 140, as shown in Figure 1B.Moreover, liquid crystal material, preferably, at least a in inclusion compound X and compound X I more, but be not limited to this, liquid crystal material also can not comprise at least a in above-claimed cpd X and compound X I or comprise the compound that other can coordinate with the described photo-sensitive monomer of the above embodiment of the present invention.And the compound X that coordinates with embodiments of the invention 2.6-naphthalene-dimethacrylate in this way, compound X I in this way 4,4'-biphenylene-dimethacrylate, its chemical formula is expressed as follows respectively:
At least a content in compound X and compound X I, preferably, different from least a content in chemical compounds I, II, III and IV, yet, be not limited to this, but also at least a content in compound X and compound X I is identical with at least a content in chemical compounds I, II, III and IV.
In order to help at least a disturbance in liquid crystal molecule 130 and photo-sensitive monomer 140, preferably, as shown in Fig. 1 C, apply in voltage and thermal source at least a this at least one substrate in substrate 110 and 120 on, to help at least a disturbance in liquid crystal molecule 130 and photo-sensitive monomer 140.At least a in above-mentioned thermal source and voltage can repeatedly apply or once apply.When repeatedly applying, at least a temperature or magnitude of voltage are identical or different in fact each time in above-mentioned thermal source and voltage.In addition, the kenel of voltage comprises direct current, alternating-current or its combination.For example, when liquid crystal molecule 130 is subject to that voltage drives and during rotation, liquid crystal molecule can be arranged as shown in Fig. 1 C with the photo-sensitive monomer rotation, but is not limited to this, also can not apply at least a at upper substrate 110 and hypocoxa 120 in thermal source and voltage, and directly carry out next program.
Please refer to Fig. 2, the schematic diagram of the optoelectronic equipment of its expression preferred embodiment of the present invention.As shown in Figure 2, can be combined into an optoelectronic equipment 200 with electronic component 150 by the described display panels 100 of above-described embodiment.Electronic component 150 comprises as controlling elements, operating component, processing element, input element, storage element, driving element, luminous element, protecting component, sensing element, detecing element or other functional element or its combination.And the type of optoelectronic equipment comprises the panel 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 etc.moreover, the type of the display panel of the above embodiment of the present invention, with at least a classification the in the kenel of the kenel of its pixel electrode and liquid crystal molecule, comprise penetrating type, semi penetration type, reflection-type, vertical orientation type (VA), horizontal cutting remodel (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), the advanced person is type (ASV) with great visual angle, fringe field switch type (FFS), continuous fireworks shape arrange type (CPA), rotational symmetry is arranged micella type (ASM), optical compensation curved arrange type (OCB), super horizontal cutting remodel (S-IPS), advanced super horizontal cutting remodel (AS-IPS), extreme edge electric field switch type (UFFS), the stabilizing polymer alignment-type, Double-visual angle type (dual-view), three visual angle types (triple-view), or other profile plate, or its combination.
Optoelectronic equipment and the manufacture method thereof of the liquid crystal panel of the disclosed photo-sensitive monomer of the above embodiment of the present invention, liquid crystal material, application photo-sensitive monomer and manufacture method thereof, application photo-sensitive monomer have multiple advantages and comprise:
1. polyreaction is fast.The photo-sensitive monomer of the above embodiment of the present invention has a plurality of (at least two) polymerizable groups, and therefore when polyreaction was carried out in photo-sensitive monomer reception light stimulus, its polymerization rate was very fast, reaches complete polymerization required time also shorter.In addition, compared to utilizing traditionally light initiator to accelerate the mode of polyreaction, the mode that the above embodiment of the present invention utilization increases reactive group density improves the collision probability, can accelerate polyreaction and but can not produce the problem of 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, can meet the UV light source that uses 365nm in existing preparation technology, therefore can effectively absorb UV light and be transferred to reactive group by energy, improving polymerization efficiency.
3. the power of putting in order to 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, can increase photo-sensitive monomer to the power of putting in order of liquid crystal molecule.
4. do not affect demonstration 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, and weak or give out light wavelength below 400nm due to fluorescence, therefore fluorescence can be effectively suppressed after connecting reactive group.That is to say, the polymeric film in liquid crystal layer can't produce color or luminous doubt.Thus, the present embodiment use polymeric film as the liquid crystal panel of alignment film or optoelectronic equipment when the show image, its display color and efficient can be kept previous level, and can not be affected.
Claims (15)
1. photo-sensitive monomer, the 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, methoxyl group, carbonyl, carboxyl, amine formyl, methylthio group, ethene carbonyl, 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, ethene carbonyl, carbonyl vinyl and singly-bound;
" L
1", " L
2", " L
3", " L
4", " L
5", " L
6" the alkane carbonyl oxygen base that independently is selected from hydrogen atom, intert-gas atoms, halogen atom, cyano group, alkyl, alkyl carbonyl, carbalkoxy and has 1 ~ 7 carbon atom wherein at least one hydrogen atom replaced by fluorine atom or chlorine atom.
2. photo-sensitive monomer as claimed in claim 1, when it is characterized in that " SP " is selected from the straight or branched alkyl, the carbon atom number that comprises between 1～8, in addition, one or two non-conterminous-CH
2-Ji is replaced by Sauerstoffatom or sulphur atom.
3. photo-sensitive monomer as claimed in claim 1 is characterized in that " P " is selected from acrylate-based, methacrylate based, vinyl, vinyloxy group, propylene ether, epoxy group(ing), group V, VI, VII, VIII and IX;
The group V is as follows with chemical formulation:
" U " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl;
The group VI is as follows with chemical formulation:
" X " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl;
The group VII is as follows with chemical formulation:
The group VIII is as follows with chemical formulation:
" Y " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl;
The group IX is as follows with chemical formulation:
" Q " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl.
4. a liquid crystal material, comprise liquid crystal molecule and photo-sensitive monomer as claimed in claim 1.
5. liquid crystal material as claimed in claim 4 is characterized in that also comprising: at least a in compound X and compound X I, and its chemical formula represents as follows:
6. liquid crystal material as claimed in claim 5, is characterized in that at least a content in compounds X and compound X I is different from least a content in compounds Ⅳ.
7. a liquid crystal panel, comprise liquid crystal material as claimed in claim 4, and its photo-sensitive monomer that comprises is aggregated into polymeric film, to be used as alignment film.
8. an optoelectronic equipment, comprise liquid crystal panel as claimed in claim 7.
9. the manufacture method of a liquid crystal panel comprises that step is as follows:
A pair of 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, methoxyl group, carbonyl, carboxyl, amine formyl, methylthio group, ethene carbonyl, 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, ethene carbonyl, carbonyl vinyl and singly-bound;
" L
1", " L
2", " L
3", " L
4", " L
5", " L
6" the alkane carbonyl oxygen base that independently is selected from hydrogen atom, intert-gas atoms, halogen atom, cyano group, alkyl, alkyl carbonyl, carbalkoxy and has 1 ~ 7 carbon atom wherein at least one hydrogen atom replaced by fluorine atom or chlorine atom; And
Apply energy source this to substrate on, with this photo-sensitive monomer of polymerization be convenient to form polymeric film this at least one substrate in substrate on, to be used as alignment film.
10. method as claimed in claim 9, it is characterized in that also comprising apply in voltage and thermal source at least a this to substrate on.
11. method as claimed in claim 9 is characterized in that " P " is selected from acrylate-based, methacrylate based, vinyl, vinyloxy group, propylene ether, epoxy group(ing), group V, VI, VII, VIII and IX;
The group V is as follows with chemical formulation:
" U " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl;
The group VI is as follows with chemical formulation:
" X " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl;
The group VII is as follows with chemical formulation:
The group VIII is as follows with chemical formulation:
" Y " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl;
The group IX is as follows with chemical formulation:
" Q " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl.
12. method as claimed in claim 9 is characterized in that this liquid crystal material, at least a in inclusion compound X and compound X I.
13. method as claimed in claim 12 is characterized in that at least a content in compounds X and compound X I is different from the content of compounds Ⅳ.
14. method as claimed in claim 9, it is characterized in that also comprising form another alignment film in this at least one substrate in substrate on, to increase the orientation effect by this alignment film that this photo-sensitive monomer is formed.
15. the manufacture method of an optoelectronic equipment comprises the manufacture method of liquid crystal panel as claimed in claim 9.
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 |
|---|---|---|---|
| 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 |
| 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 |
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| 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 |
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| Publication Number | Publication Date |
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| CN103113230A true CN103113230A (en) | 2013-05-22 |
| CN103113230B CN103113230B (en) | 2015-11-11 |
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| 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107290891A (en) * | 2017-05-25 | 2017-10-24 | 菏泽学院 | The continuous controllable display in visual angle |
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| DE102009011652B4 (en) * | 2008-03-25 | 2018-02-22 | Merck Patent Gmbh | Liquid crystal medium and its use |
| 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 |
| WO2012022388A1 (en) | 2010-07-22 | 2012-02-23 | Merck Patent Gmbh | Polymer-stabilized 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 |
| WO2012017883A1 (en) | 2010-08-03 | 2012-02-09 | シャープ株式会社 | Liquid crystal display device and liquid crystal display device manufacturing method |
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| CN103080824B (en) | 2010-09-07 | 2016-03-09 | 夏普株式会社 | Liquid crystal layer forms the manufacture method with composition, liquid crystal indicator and liquid crystal indicator |
| 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 |
| WO2012086715A1 (en) | 2010-12-22 | 2012-06-28 | シャープ株式会社 | Liquid crystal orienting agent, lcd device, and method for producing lcd device |
| CN103459433B (en) * | 2011-03-09 | 2015-05-27 | 夏普株式会社 | 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 |
| 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 |
| 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 |
| 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 |
| 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| CN100392501C (en) * | 2005-03-24 | 2008-06-04 | 友达光电股份有限公司 | Liquid crystal turning additive, liquid crystal display device containing it and manufacturing method |
| 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 |
| 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 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107290891A (en) * | 2017-05-25 | 2017-10-24 | 菏泽学院 | The continuous controllable display in visual angle |
| CN107290891B (en) * | 2017-05-25 | 2023-08-04 | 菏泽学院 | Viewing angle continuously controllable display |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101008784B (en) | 2011-01-12 |
| CN103113230B (en) | 2015-11-11 |
| CN101008784A (en) | 2007-08-01 |
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