CN101819381A - Photosensitive monomer, liquid crystal panel and manufacturing method thereof - Google Patents

Photosensitive monomer, liquid crystal panel and manufacturing method thereof Download PDF

Info

Publication number
CN101819381A
CN101819381A CN201010002858A CN201010002858A CN101819381A CN 101819381 A CN101819381 A CN 101819381A CN 201010002858 A CN201010002858 A CN 201010002858A CN 201010002858 A CN201010002858 A CN 201010002858A CN 101819381 A CN101819381 A CN 101819381A
Authority
CN
China
Prior art keywords
atom
group
photo
liquid crystal
reach
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.)
Pending
Application number
CN201010002858A
Other languages
Chinese (zh)
Inventor
谢忠憬
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
AU Optronics Corp
Original Assignee
AU Optronics Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by AU Optronics Corp filed Critical AU Optronics Corp
Priority to CN201010002858A priority Critical patent/CN101819381A/en
Publication of CN101819381A publication Critical patent/CN101819381A/en
Pending legal-status Critical Current

Links

Images

Landscapes

  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The invention discloses a photosensitive monomer which is a compound III, wherein m is no less than 1, L is hydrogen atom, fluorine atom, chlorine atom, cyano, alkyl, alkylcarbonyl, carbalkoxy or alkylcarbonyloxy with 1-7 carbon atoms; R is hydrogen atom, fluorine atom, chlorine atom, cyano, thiocyano, sulfur pentafluoride group, nitrite radical, linear or branched alkyl with 1-12 carbon atoms or Z2-Sp2-P2 group; Z1 and Z2 are respectively oxygen atom, sulfur atom, methoxy, carbonyl, carboxyl, carbamoyl, methylthio, ethylene carbonyl, carbonyl vinyl or single bond; and Sp1 and Sp2 are linear or branched alkyl with 1-8 carbon atoms or single bond.

Description

Photo-sensitive monomer, liquid crystal panel and manufacture method thereof
The application is dividing an application of Chinese patent application 200710006219.2 (applying date: on February 7th, 2007, denomination of invention: photo-sensitive monomer, liquid crystal panel and manufacture method thereof).
Technical field
The present invention relates to a kind of photo-sensitive monomer, and particularly relate to a kind of photo-sensitive monomer that is applied to liquid crystal panel and manufacture method thereof.
Background technology
Liquid crystal panel development a kind of technology of orientation in recent years: the polymerization macromolecule auxiliary ligand is to (Polymer-Stabilizing Alignment, PSA) technology, be that photo-sensitive monomer is sneaked in the liquid crystal layer, treat its arrange after irradiating ultraviolet light, allow photo-sensitive monomer aggregate into the orientation polymkeric substance, the guiding Liquid Crystal Molecules Alignment.
In order to shorten polymerization time, can in liquid crystal layer, mix photo-sensitive monomer and light initiator (initiator) simultaneously, help the photo-sensitive monomer rapid polymerization.Yet though light initiator can quicken the time of making, still produced liquid crystal panel can produce the problem of image residue (image sticking).That is to say, switch to another image after showing same image when showing when liquid crystal panel is long-time, the image of front can be long-time residual and be overlapped on follow-up image.
Summary of the invention
The object of the present invention is to provide a kind of photo-sensitive monomer, liquid crystal panel and manufacture method thereof, wherein the intermediate that the polymer-based group of photo-sensitive monomer can stopping reaction can allow polyreaction more complete.
The present invention proposes a kind of photo-sensitive monomer, be selected from Compound I, II, III one of them:
Figure G2010100028583D00011
Figure G2010100028583D00021
Figure G2010100028583D00022
" L " is hydrogen atom, fluorine atom, chlorine atom, cyano group, alkyl, alkyl carbonyl, alkoxy carbonyl group or the alkane carbonyl oxygen base with 1 to 7 carbon atom." R " be hydrogen atom, fluorine atom, chlorine atom, cyano group, thiocyano, pentafluoride-sulfanyl, nitrite anions, have the straight or branched alkyl or the " Z of 1 to 12 carbon atom 2-Sp 2-P 2" group." Z 1" reach " Z 2" be respectively oxygen atom, sulphur atom, methoxyl, carbonyl, carboxyl, amine formyl, methyl mercapto, ethene carbonyl, carbonyl vinyl or singly-bound." Sp 1" reach " Sp 2" for having the straight or branched alkyl or the singly-bound of 1 to 8 carbon atom.
" P 1" reach " P 2" be selected from group IV, V, VI, VII and VIII one of them, as follows with chemical formulation:
Figure G2010100028583D00023
Group IV " U " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl.
Figure G2010100028583D00024
Group V " X " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl.
Figure G2010100028583D00031
Group VI is pyrroles-2, and the 5-diketone (pyrrole-2,5-dione).
Figure G2010100028583D00032
Group VII " Y " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl;
As follows with chemical formulation:
Figure G2010100028583D00033
Group VIII " Q " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl.
The present invention also proposes a kind of liquid crystal panel, and it comprises infrabasal plate, upper substrate and liquid crystal layer.Liquid crystal layer is filled between upper substrate and the infrabasal plate, and wherein liquid crystal layer comprises liquid crystal molecule and orientation condensate, and the orientation condensate is represented with Formula I X:
The manufacture method that the present invention also proposes a kind of liquid crystal panel comprises: upper substrate and infrabasal plate (a) are provided; (b) inject liquid crystal material between upper substrate and infrabasal plate, liquid crystal material comprises a plurality of liquid crystal molecules and a plurality of above-mentioned photo-sensitive monomer; And (c) apply voltage, and, be the orientation polymkeric substance in order to the polymerization photo-sensitive monomer with ultraviolet source irradiation at upper substrate and infrabasal plate.
For foregoing of the present invention can be become apparent, preferred embodiment cited below particularly, and conjunction with figs. are described in detail below:
Description of drawings
Figure 1A~1D represents the making process flow diagram according to a kind of liquid crystal panel of preferred embodiment of the present invention.
[critical piece symbol description]
100: liquid crystal panel
110: upper substrate
120: infrabasal plate
130: liquid crystal molecule
140: photo-sensitive monomer
145: the orientation polymkeric substance
Embodiment
The present invention mainly proposes a kind of photo-sensitive monomer, when it is applied to liquid crystal panel manufacturing method, can shorten polymerization time, and improves the problem of image residue.Below introduce chemical general formula, preferred embodiment and the synthetic method of photo-sensitive monomer earlier, introduce the method that these photo-sensitive monomers is applied to make electrooptical device and liquid crystal panel again.
Photo-sensitive monomer
The present invention mainly proposes a kind of photo-sensitive monomer, be selected from Compound I, II, III one of them.
Compound I is with chemical formulation:
Figure G2010100028583D00051
" L " is hydrogen atom, fluorine atom, chlorine atom, cyano group (cyano group), alkyl (alkyl), alkyl carbonyl (alkylcarbonyl), alkoxy carbonyl group (alkoxycarbonyl) or the alkane carbonyl oxygen base (alkylcarbonyloxy) with 1 to 7 carbon atom.One or more hydrogen atom can be replaced by fluorine atom or chlorine atom in the above-mentioned alkane carbonyl oxygen base.
" R " be hydrogen atom, fluorine atom, chlorine atom, cyano group (cyano group ,-CN), thiocyano (thiocyanato ,-SCN), pentafluoride-sulfanyl (pentafluoro-lambda~6~-sulfanyl ,-SF 5H), nitrite anions (nitrite ,-NO 2), have the straight or branched alkyl (alkyl group) or " Z of 1 to 12 carbon atom 2-Sp 2-P 2" group.Above-mentioned non-conterminous one or two-CH with straight or branched alkyl of 1 to 12 carbon atom 2-Ji can by oxygen atom, sulphur atom, ethenylidene (vinylene ,-CH=CH-), carbonyl (carbonyl, C=O), carboxyl (caroboxyl ,-COO-), the sulfuration carbonyl (carbothio, S-CO-,-CO-S-) or alkynyl (alkyne) replace.
" Z 1" reach " Z 2" be respectively oxygen atom, sulphur atom, methoxyl (methyoxy ,-OCH 2-), carbonyl (carbonyl, C=O), carboxyl (caroboxyl ,-COO-), amine formyl (carbamoyl ,-CO-N 0R-,-N 0R-CO-), methyl mercapto (methylthio ,-CH 2S-,-SCH 2-), the ethene carbonyl (ethenylcarbonyl ,-CH=CH-COO-), the carbonyl vinyl (carbonylethenyl ,-COO-CH=CH-) or singly-bound.
" Sp 1" reach " Sp 2" for having the straight or branched alkyl or the singly-bound of 1 to 8 carbon atom.Above-mentioned non-conterminous one or two-CH with straight or branched alkyl of 1 to 8 carbon atom 2-Ji can be replaced by oxygen atom or sulphur atom.
" P 1" reach " P 2" be selected from group IV, V, VI, VII and VIII one of them, group IV is as follows with chemical formulation:
Figure G2010100028583D00061
" U " is selected from hydrogen atom, methyl (methyl), fluorine atom, trifluoromethyl (trifluoromethyl ,-CF 3) and phenyl (Phenyl);
Group V is as follows with chemical formulation:
Figure G2010100028583D00062
" X " is selected from hydrogen atom, methyl (methyl), fluorine atom, trifluoromethyl (trifluoromethyl ,-CF 3) and phenyl (Phenyl);
Group VI is pyrroles-2, the 5-diketone (pyrrole-2,5-dione), as follows with chemical formulation:
Figure G2010100028583D00063
Group VII is as follows with chemical formulation:
Figure G2010100028583D00064
" Y " is selected from hydrogen atom, methyl (methyl), fluorine atom, trifluoromethyl (trifluoromethyl ,-CF 3) and phenyl (Phenyl);
Group VIII is as follows with chemical formulation:
Figure G2010100028583D00071
" Q " is selected from hydrogen atom, methyl (methyl), fluorine atom, trifluoromethyl (trifluoromethyl ,-CF 3) and phenyl (Phenyl).
Hereinafter, we enumerate several groups of embodiment illustrate photo-sensitive monomer be Compound I may implement the sample attitude, and as follows with chemical formulation:
Figure G2010100028583D00072
Wherein, " L " is hydrogen atom, and " R " is " Z 2-Sp 2-P 2" group, " Z 1" reach " Z 2" be all oxygen atom, " Sp 1" reach " Sp 2" be all ethyl group, " P 1" reach " P 2" be group VII and wherein " Y " for fluorine atom;
Figure G2010100028583D00073
Wherein, " L " is hydrogen atom, and " R " is " Z 2-Sp 2-P 2" group, " Z 1" reach " Z 2" be all oxygen atom, " Sp 1" reach " Sp 2" be all ethyl group, " P 1" reach " P 2" be group VII and wherein " Y " for trifluoromethyl;
Wherein, " L " is hydrogen atom, and " R " is " Z 2-Sp 2-P 2" group, " Z 1" reach " Z 2" be all oxygen atom, " Sp 1" reach " Sp 2" be all ethoxy alkyl, " P 1" reach " P 2" be group VIII and wherein " Q " for phenyl;
Figure G2010100028583D00081
Wherein, " L " is hydrogen atom, and " R " is " Z 2-Sp 2-P 2" group, " Z 1" reach " Z 2" be all oxygen atom, " Sp 1" reach " Sp 2" be all ethyl group, " P 1" reach " P 2" be group IV and wherein " U " for methyl;
Wherein, " L " is hydrogen atom, and " R " is " Z 2-Sp 2-P 2" group, " Z 1" reach " Z 2" be all oxygen atom, " Sp 1" reach " Sp 2" be all ethyl group, " P 1" reach " P 2" be group VI (pyrroles-2,5-diketone (pyrrole-2,5-dione)).
Below enumerate compound [I-1] again and be example; so that its synthetic method to be described; yet those skilled in the art should understand the structure and the synthetic method of Compound I of the present invention to be 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 desire protection.Compound I for example is compound [I-1], wherein " Z 1" be oxygen atom, " Sp 1" be singly-bound, " P 1" be group VIII, " Q " is phenyl, " R " for having the straight chained alkyl (alkyl) of 4 carbon atoms, and straight chained alkyl first-CH 2-Ji is replaced by oxygen atom.Compound [I-1] is represented with Chemical formula 1, and its synthesis mode is expressed as follows with chemical equation (1):
For synthetic compound [I-1] as shown in chemical equation (1), at first bleed with the deaeration in condenser de-watering apparatus in 4-butoxyphenol (compound of chemical formula [1]) the adding 100mL two-neck bottle with 1 mM.Behind the input nitrogen three times, on addition funnel, connect nitrogen, make reactive system be in the anaerobic anhydrous state.Then, under room temperature with the triethylamine of 1.5 mMs (triethylamine, TEA) and 30 milliliters of tetrahydrofurans after dewatering (Tetrahydrofuran THF) adds and is stirred to dissolving.Afterwards, inject the methacrylic chloride (methacryloyl chloride) of 1.5 mMs under ice bath, at room temperature reaction is to every other day.Then, bleed and filter and, collect filtrate decompression and concentrate with tetrahydrofuran (THF) flushing, with ethyl acetate (Ethyl Acetate, EA) and water extract, with magnesium sulphate (MgSO 4) filtration that dewaters and bleed, concentrated then vacuumizing gets yellow solid.At last, (hexane) does crystallization again with normal hexane, and can obtain outward appearance is white solid, compound [the I-1] (C of productive rate about 65% 19H 20O 3).
The chemical formulation of Compound I I is:
Figure G2010100028583D00091
Wherein, " Z 1", " Sp 1", " P 1", " L m", " R " group is identical with the feature of corresponding group in the Compound I, does not repeat them here.
Hereinafter, we enumerate several groups of embodiment illustrate photo-sensitive monomer be Compound I I may implement the sample attitude, and as follows with chemical formulation:
Figure G2010100028583D00092
Wherein, m=3, " L " are hydrogen atom, and " R " is " Z 2-Sp 2-P 2" group, " Z 1" reach " Z 2" be all oxygen atom, " Sp 1" reach " Sp 2" be all ethyl group, " P 1" reach " P 2" be group VII and wherein " Y " for fluorine atom;
Figure G2010100028583D00093
Wherein, m=3, " L " are hydrogen atom, and " R " is " Z 2-Sp 2-P 2" group, " Z 1" reach " Z 2" be all oxygen atom, " Sp 1" reach " Sp 2" be all ethyl group, " P 1" reach " P 2" be group VII and wherein " Y " for trifluoromethyl;
Figure G2010100028583D00101
Wherein, m=3, " L " are hydrogen atom, and " R " is " Z 2-Sp 2-P 2" group, " Z 1" reach " Z 2" be all oxygen atom, " Sp 1" reach " Sp 2" be all ethoxy alkyl, " P 1" reach " P 2" be group VIII and wherein " Q " for phenyl;
Figure G2010100028583D00102
Wherein, m=3, " L " are hydrogen atom, and " R " is " Z 2-Sp 2-P 2" group, " Z 1" reach " Z 2" be all oxygen atom, " Sp 1" reach " Sp 2" be all ethyl group, " P 1" reach " P 2" be group IV and wherein " U " for methyl;
Figure G2010100028583D00103
Wherein, m=3, " L " are hydrogen atom, and " R " is " Z 2-Sp 2-P 2" group, " Z 1" reach " Z 2" be all oxygen atom, " Sp 1" reach " Sp 2" be all ethyl group, " P 1" reach " P 2" be group VI (pyrroles-2,5-diketone (pyrrole-2,5-dione)).
Below enumerate compound [II-1] again and be example; so that its synthetic method to be described; yet those skilled in the art should understand structure and the synthetic method of Compound I I of the present invention to be 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 desire protection.Compound I I for example is compound [II-1], wherein " Z 1" be oxygen atom, " Sp 1" be singly-bound, " P 1" be group VIII, " Q " is phenyl, " R " for having the straight chained alkyl (alkyl) of 4 carbon atoms, and straight chained alkyl first-CH 2-Ji is replaced by oxygen atom.Compound [II-1] is represented with Chemical formula 2, and its synthesis mode is expressed as follows with chemical equation (2):
For synthetic compound [II-1] as chemical equation (2) as shown in, at first with the 4-butoxy of 1 mM, 4 '-bleed with the deaeration in condenser de-watering apparatus in hydroxybiphenyl (compound of chemical formula [2]) the adding 100mL two-neck bottle.Behind the input nitrogen three times, on addition funnel, connect nitrogen, make reactive system be in the anaerobic anhydrous state.Then, at room temperature with the triethylamine of 1.5 mMs (triethylamine, TEA) and 30 milliliters of tetrahydrofurans after dewatering (Tetrahydrofuran THF) adds and is stirred to dissolving.Afterwards, inject the methacrylic chloride (methacryloyl chloride) of 1.5 mMs under ice bath, at room temperature reaction is to every other day.Then, bleed and filter and, collect filtrate decompression and concentrate with tetrahydrofuran (THF) flushing, with ethyl acetate (Ethyl Acetate, EA) and water extract, with magnesium sulphate (MgSO 4) filtration that dewaters and bleed, concentrated then vacuumizing gets yellow solid.At last, (hexane) does crystallization again with normal hexane, and can obtain outward appearance is white solid, compound [the II-1] (C of productive rate about 60% 25H 24O 3).
Compound III is with chemical formulation:
Figure G2010100028583D00112
Wherein, " Z 1", " Sp 1", " P 1", " L m", " R " group is identical with the feature of corresponding group in the Compound I, does not repeat them here.
Hereinafter, we enumerate several groups of embodiment illustrate photo-sensitive monomer be compound III may implement the sample attitude, and as follows with chemical formulation:
M=3 wherein, " L " is hydrogen atom, " R " is " Z 2-Sp 2-P 2" group, " Z 1" reach " Z 2" be oxygen atom, " Sp 1" reach " Sp 2" be singly-bound, " P 1" reach " P 2" be group VIII, " Q " in the group VIII be phenyl (phenyl, Ph).
Figure G2010100028583D00122
Wherein, m=3, " L " are hydrogen atom, and " R " is " Z 2-Sp 2-P 2" group, " Z 1" reach " Z 2" be all oxygen atom, " Sp 1" reach " Sp 2" be all ethyl group, " P 1" reach " P 2" be group VII and wherein " Y " for fluorine atom;
Figure G2010100028583D00123
Wherein, m=3, " L " are hydrogen atom, and " R " is " Z 2-Sp 2-P 2" group, " Z 1" reach " Z 2" be all oxygen atom, " Sp 1" reach " Sp 2" be all ethyl group, " P 1" reach " P 2" be group VII and wherein " Y " for trifluoromethyl;
Figure G2010100028583D00124
Wherein, m=3, " L " are hydrogen atom, and " R " is " Z 2-Sp 2-P 2" group, " Z 1" reach " Z 2" be all oxygen atom, " Sp 1" reach " Sp 2" be all ethoxy alkyl, " P 1" reach " P 2" be group VIIVIII and wherein " Q " for phenyl;
Figure G2010100028583D00125
Wherein, m=3, " L " are hydrogen atom, and " R " is " Z 2-Sp 2-P 2" group, " Z 1" reach " Z 2" be all oxygen atom, " Sp 1" reach " Sp 2" be all ethyl group, " P 1" reach " P 2" be group IV and wherein " U " for methyl;
Figure G2010100028583D00131
Wherein, m=3, " L " are hydrogen atom, and " R " is " Z 2-Sp 2-P 2" group, " Z 1" reach " Z 2" be all oxygen atom, " Sp 1" reach " Sp 2" be all ethyl group, " P 1" reach " P 2" be group VI (pyrroles-2,5-diketone (pyrrole-2,5-dione)).
Below enumerate compound [III-1] in addition and be example; so that its synthetic method to be described; yet those skilled in the art should understand the structure and the synthetic method of compound III of the present invention to be not limited thereto, so long as meet the scope that the compound of above-mentioned chemical general formula and group restriction belongs to institute of the present invention desire protection.Compound III for example is compound [III-1], wherein " Z 1" be oxygen atom, " Sp 1" be singly-bound, " P 1" be group VIII, " Q " is phenyl, " R " for having the straight chained alkyl (alkyl) of 4 carbon atoms, and straight chained alkyl first-CH 2-Ji is replaced by oxygen atom.The synthesis mode of compound [III-1] is expressed as follows with chemical equation (3):
Figure G2010100028583D00132
For synthetic compound [III-1] as shown in chemical equation (3), at first bleed with the deaeration in condenser de-watering apparatus in 6-butoxynaphthalen-2-ol (compound of chemical formula [3]) the adding 100mL two-neck bottle with 1 mM.Behind the input nitrogen three times, on addition funnel, connect nitrogen, make reactive system be in the anaerobic anhydrous state.Then, at room temperature with the triethylamine of 1.5 mMs (triethylamine, TEA) and 30 milliliters of tetrahydrofurans after dewatering (Tetrahydrofuran THF) adds and is stirred to dissolving.Afterwards, inject the methacrylic chloride (methacryloyl chloride) of 1.5 mMs under ice bath, at room temperature reaction is to every other day.Then, bleed and filter and, collect filtrate decompression and concentrate with tetrahydrofuran (THF) flushing, with ethyl acetate (Ethyl Acetate, EA) and water extract, with magnesium sulphate (MgSO 4) filtration that dewaters and bleed, concentrated then vacuumizing gets yellow solid.At last, (hexane) does crystallization again with normal hexane, and can obtain outward appearance is white solid, compound [the III-1] (C of productive rate about 55% 23H 22O 3).
The application process of photo-sensitive monomer
The photo-sensitive monomer that the present invention proposes can be applicable to the polymerization macromolecule auxiliary ligand to (Polymer-Stabilizing Alignment is PSA) in the technology, in order to make liquid crystal panel.Figure 1A~1D represents the making process flow diagram according to a kind of liquid crystal panel of preferred embodiment of the present invention.Details are as follows for its method for making of the liquid crystal panel of present embodiment.
At first, provide upper substrate 110 and infrabasal plate 120, shown in Figure 1A.Then, inject liquid crystal material between upper substrate 110 and infrabasal plate 120, liquid crystal material comprises a plurality of liquid crystal molecules 130 and a plurality of photo-sensitive monomer 140, shown in Figure 1B.These photo-sensitive monomers 140 are selected from wherein at least a of above-claimed cpd I, II, III.At last, apply voltage at upper substrate 110 and infrabasal plate 120, and with ultraviolet source (ultraviolet light, UV light) irradiation, shown in Fig. 1 C.These photo-sensitive monomers 140 of polymerization are orientation polymkeric substance 145, shown in Fig. 1 D.
For instance, when using compound [III-2] as photo-sensitive monomer, then its polyreaction is expressed as follows with chemical equation:
Figure G2010100028583D00141
Polymer-based group " the P of compound [III-2] 1" mainly be on methacrylate based (methacrylate), to do modification, the intermediate that the functional group after modifying can stopping reaction can allow polyreaction more complete.In addition, the functional group after the modification carries out the cyclization reaction (position shown in red arrow) of 2+2, so reacted polymer architecture (chemical formula [IX], just the orientation condensate 145) can become comparatively firm.
Please refer to Fig. 1 D, the liquid crystal panel 100 that forms according to said method comprises upper substrate 110, infrabasal plate 120 and fills liquid crystal layer therebetween.Liquid crystal layer comprises liquid crystal molecule 130 and orientation condensate 145.Orientation condensate 145 is represented with Formula I X:
Figure G2010100028583D00151
As mentioned above, it is firmer that reacted orientation condensate 145 structures (chemical formula [IX]) have the Fourth Ring texture ratio, and preferable orientation ability not only can be provided, and can also solve the problem of image residue in the lump.
The disclosed photo-sensitive monomer of the above embodiment of the present invention, liquid crystal panel and manufacture method thereof have multiple advantages and comprise:
1. polyreaction is complete.The photo-sensitive monomer that the present invention proposes, its polymer-based group IV, V, VI, VII and VIII can stopping reaction intermediate, can allow polyreaction more complete.
2. the orientation polymer structure is firm.Polymer-based group IV, V, VI, VII and VIII can carry out the cyclization reaction of 2+2, so that reacted polymer architecture can become is comparatively firm, not only can provide preferable orientation ability, can also solve the problem of image residue in the lump.
3. polymerization efficiency height.The intercalated nucleus structure of the photo-sensitive monomer of present embodiment has strong absorption peak at 300-400nm, can meet the UV light source that uses 365nm among the existing preparation technology, therefore can effectively absorb UV light and be transferred to reactive group, improve polymerization efficiency by energy.
4. it is photochromic not influence demonstration.The intercalated nucleus structure of the photo-sensitive monomer of present embodiment has strong absorption peak at 300-400nm, because it is more weak or give out light wavelength below 400nm to have a fluorescent, therefore fluorescent can effectively be suppressed after connecting reactive group.That is to say that the polymer film in the liquid crystal layer can't produce color or luminous doubt.Thus, when the show image, its display color and efficient can be kept original level to the use polymer film of present embodiment, and can not be affected as the liquid crystal panel of alignment film or electrooptical device.

Claims (10)

1. photo-sensitive monomer, it is a compound III
This compound III is with chemical formulation:
Figure F2010100028583C00011
" L " is hydrogen atom, fluorine atom, chlorine atom, cyano group, alkyl, alkyl carbonyl, alkoxy carbonyl group or the alkane carbonyl oxygen base with 1 to 7 carbon atom, wherein m 〉=1;
" R " be hydrogen atom, fluorine atom, chlorine atom, cyano group, thiocyano, pentafluoride-sulfanyl, nitrite anions, have the straight or branched alkyl or the " Z of 1 to 12 carbon atom 2-Sp 2-P 2" group;
" Z 1" reach " Z 2" be respectively oxygen atom, sulphur atom, methoxyl, carbonyl, carboxyl, amine formyl, methyl mercapto, ethene carbonyl, carbonyl vinyl or singly-bound; And
" Sp 1" reach " Sp2 " for having the straight or branched alkyl or the singly-bound of 1 to 8 carbon atom;
" P 1" reach " P 2" be selected from group IV, V, VI, VII and VIII one of them, group IV is as follows with chemical formulation:
Figure F2010100028583C00012
" U " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl;
Group V is as follows with chemical formulation:
Figure F2010100028583C00013
" X " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl;
Group VI is pyrroles-2, and the 5-diketone is as follows with chemical formulation:
Figure F2010100028583C00021
Group VII is as follows with chemical formulation:
Figure F2010100028583C00022
" Y " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl;
Group VIII is as follows with chemical formulation:
Figure F2010100028583C00023
" Q " is selected from hydrogen atom, methyl, fluorine atom, trifluoromethyl and phenyl.
2. photo-sensitive monomer as claimed in claim 1 is characterized in that the one or more hydrogen atom of alkane carbonyl oxygen base is replaced by fluorine atom or chlorine atom.
3. photo-sensitive monomer as claimed in claim 1 is characterized in that having the non-conterminous one or two-CH of the straight or branched alkyl of 1 to 12 carbon atom 2-Ji is replaced by oxygen atom, sulphur atom, ethenylidene, carbonyl, carboxyl, sulfuration carbonyl or alkynyl.
4. photo-sensitive monomer as claimed in claim 1 is characterized in that having the non-conterminous one or two-CH of the straight or branched alkyl of 1 to 8 carbon atom 2-Ji is replaced by oxygen atom or sulphur atom.
5. photo-sensitive monomer as claimed in claim 1 is characterized in that " R " is " Z 2-Sp 2-P 2" group.
6. photo-sensitive monomer as claimed in claim 5 is characterized in that " Z 1" reach " Z 2" be oxygen atom, " Sp 1" reach " Sp 2" be singly-bound, " P 1" reach " P 2" be that group VIII and " Q " are phenyl.
7. photo-sensitive monomer as claimed in claim 1 is characterized in that " Z 1" be oxygen atom, " Sp 1" be singly-bound, " P 1" be that group VIII and " Q " are phenyl.
8. photo-sensitive monomer as claimed in claim 7 is characterized in that " R " is the straight chained alkyl with 4 carbon atoms, and one-CH of straight chained alkyl 2-Ji is replaced by oxygen atom.
9. liquid crystal panel comprises:
Infrabasal plate and upper substrate; And
Liquid crystal layer is filled between this upper substrate and this infrabasal plate, and wherein this liquid crystal layer comprises liquid crystal molecule and orientation condensate, and this orientation condensate is represented with Formula I X:
Figure F2010100028583C00031
10. the manufacture method of a liquid crystal panel comprises that step is as follows:
Upper substrate and infrabasal plate are provided;
Inject liquid crystal material between this upper substrate and this infrabasal plate, this liquid crystal material comprises a plurality of liquid crystal molecules and a plurality of as each described photo-sensitive monomer of claim 1~7; And
Apply voltage at this upper substrate and this infrabasal plate, and, be the orientation polymkeric substance in order to those photo-sensitive monomers of polymerization with ultraviolet source irradiation.
CN201010002858A 2007-02-07 2007-02-07 Photosensitive monomer, liquid crystal panel and manufacturing method thereof Pending CN101819381A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201010002858A CN101819381A (en) 2007-02-07 2007-02-07 Photosensitive monomer, liquid crystal panel and manufacturing method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201010002858A CN101819381A (en) 2007-02-07 2007-02-07 Photosensitive monomer, liquid crystal panel and manufacturing method thereof

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CN2007100062192A Division CN101008783B (en) 2007-02-07 2007-02-07 Photosensitive monomer and liquid crystal panel, and manufacture method therefor

Publications (1)

Publication Number Publication Date
CN101819381A true CN101819381A (en) 2010-09-01

Family

ID=42654525

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201010002858A Pending CN101819381A (en) 2007-02-07 2007-02-07 Photosensitive monomer, liquid crystal panel and manufacturing method thereof

Country Status (1)

Country Link
CN (1) CN101819381A (en)

Similar Documents

Publication Publication Date Title
CN101008784B (en) Photosensitive monomer, liquid crystal material, liquid crystal panel and manufacture method, and photoelectric equipment and manufacture method thereof
CN101013262B (en) Photo-sensitive monomer, liquid crystal material, liquid crystal panel and method of fabrication, photoelectric device and fabricating 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
JP5240798B2 (en) Refractive index improver, and resin composition, polymerization or curable composition and optical material containing the same
CN103459443A (en) Copolymer, resin composition and photosensitive resin composition each containing said copolymer, and color filter
KR20140007023A (en) Dye dispersion, photosensitive resin composition for color filter, color filter, liquid crystal display device, and organoluminescent display device
CN105278247A (en) Curable resin composition and application thereof
CN105792921B (en) Non- water system dispersant, colored filter colorant dispersion liquid, colored filter, liquid crystal display device and organic light-emitting display device
JP6094912B2 (en) Bicarbazole compound, photocurable composition, cured product thereof, curable composition for plastic lens, and plastic lens
TW200613864A (en) Photosensitive resin composition for spacer
JP2011162716A (en) Curable resin composition, colored curable resin composition for use in color filter, and color filter
JP6078999B2 (en) Red pigment dispersion for color filter and production method thereof, red photosensitive resin composition for color filter and production method thereof, color filter, liquid crystal display device and organic light emitting display device
CN103228737A (en) Novel compound, dye and colored photosensitive composition
JP2020091489A (en) Color material dispersion liquid, photosensitive color resin composition for color filter, color filter, liquid crystal display device, and organic light-emitting display device
CN101008783B (en) Photosensitive monomer and liquid crystal panel, and manufacture method therefor
JP2004002373A (en) Maleimide derivative and its polymer
CN109294460A (en) A kind of UV solidification Liquid optical clear adhesive of color inhibition and preparation method thereof
CN104903405B (en) Cured film is formed with composition, orientation material and phase difference material
TW201316123A (en) Coloring composition for color filter, color filter and display element
CN101817777A (en) Photosensitive monomer, liquid crystal panel and manufacturing method thereof
CN101819381A (en) Photosensitive monomer, liquid crystal panel and manufacturing method thereof
CN100573275C (en) Display panels and liquid crystal compound
JP2013053224A (en) Pigment dispersion, negative resist composition for color filter and method for producing the same, color filter, liquid crystal display and organic light emitting display
CN102692661B (en) The manufacture method of colored filter, colored filter and liquid crystal display cells
JP2023104975A (en) Coloring composition, color filter, solid-state image sensor, and liquid crystal display device

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C12 Rejection of a patent application after its publication
RJ01 Rejection of invention patent application after publication

Open date: 20100901