CN101337899A - Diphenylamines substitutedstyrylbiphenyl compounds for preparing blueing material and use thereof - Google Patents
Diphenylamines substitutedstyrylbiphenyl compounds for preparing blueing material and use thereof Download PDFInfo
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Abstract
The invention relates to a diphenylamine-styrene biphenyl compound containing a photocrosslinking group, and the application in preparing a blue-light organic electroluminescent material and in organic electroluminescence, and belongs to the technical field of organic semiconductor light-emitting material. A substance with UV curing activity is formed by connecting olefinic acid ester with benzene ring of diphenylamine-styrene biphenyl, which is the blue-light organic electroluminescent material, and the substance is mixed with a small amount of UV-curable initiator to form a film by spin coating and is crosslinked under the action of UV rays to form an organic electroluminescent layer insoluble in a solvent. The product can prevent interlayer mixing while multilayer spin coating, and the side group has less influence on the light emission performance. The method is a better method for preparing the organic electroluminescent layer.
Description
Technical field
The invention belongs to the technical field of organic flat-panel monitor, be specifically related to a kind of preparation and application of electroluminescent organic material of the Photocrosslinkable that contains enoate side group.
Background technology
Organic light emitting display, (Organic Light Emitting Display is called for short OLED), it belongs to the kind of new emergence on mobile phone screen, MP3, MP4 screen, be described as " dreamlike indicating meter ".The OLED technique of display is different with traditional LCD display mode, need not backlight, adopts extremely thin coating of organic material and glass substrate, and when electric current passed through, these organic materialss will be luminous.Therefore the OLED screen can be done lighter and thinnerly, and visible angle is bigger, and can significantly save electric energy.
The structure of OLED indicating meter has some organic material layers usually between metallic cathode and ito anode.The main method of preparation has spin-coating and vacuum plating, but often uses the method for spin-coating when big area is film forming.Process solvent at the middle and upper levels in different organic layer spin-coating film tends to the film forming organic molecule of lower floor be dissolved again and run off, because the thickness of organic layer is nano level, is formed hole after the dissolution with solvents easily, can cause the phenomenon of luminous impure or short circuit.For the organic layer that makes spin coating no longer is dissolved in solvent, the molecule of organic layer can be carried out photo-crosslinking, with chemical bond they are linked together, make it no longer be dissolved in organic solvent.
Group with photo-crosslinking ability is a lot, but research of this respect at present and report are few, domestic patent and the document that does not also have this respect.
The alkene esters of gallic acid is the ultraviolet light polymerization group of using always, its raw material propylene acid is easy to get, just can on the organic semiconductor agent structure, introduce alkene esters of gallic acid side group by simple reaction, give the activity of agent structure ultraviolet light polymerization, under UV-irradiation, be cross-linked to form insoluble organic electro luminescent layer by initiator again.
Summary of the invention
The shortcoming of prior art is that the process solvent at the middle and upper levels of organic layer spin-coating film tends to the film forming organic molecule of lower floor be dissolved again and run off, and luminescent layer forms hole easily, causes the phenomenon of luminous impure or short circuit.
At this shortcoming, the object of the present invention is to provide a kind of pentanoic styrylbiphenyl blue-ray organic electroluminescent material that contains enoate side group, and carry out ultraviolet light cross-linking, be applied in the flat-panel display device as insoluble blue-ray organic electroluminescent layer.
The present invention combines the good photo-crosslinking performance of olefin(e) acid ester and the blue light emitting effect of pentanoic styrylbiphenyl, prepared can photo-crosslinking pentanoic styrylbiphenyl electroluminescent organic material.It is the blue light electroluminescent material of high comprehensive performance.
The diphenylamines substitutedstyrylbipcompounds compounds that is used for blue light material is characterized in that it being the pentanoic styrylbiphenyl with enoate side group, general structure following (Fig. 1):
Wherein R is the straight or branched alkyl of 2～6 carbon, R
1Be hydrogen or methyl.
Compound as mentioned above, comprising: two (diacrylate oxygen third/fourth/penta/own ester group aniline phenyl vinyl) biphenyl, two (diacrylate oxygen isobutyl/penta/own ester group aniline phenyl vinyl) biphenyl, two (dimethacrylate oxygen third/fourth/penta/own ester group aniline phenyl vinyl) biphenyl, two (dimethacrylate isobutyl/penta/hexyl ester group aniline phenyl vinyl) biphenyl.
Prepare the method for compound as mentioned above, wherein synthesis step is as follows:
(1) two pairs of anisidino of 18～20 parts of quality is dissolved in 70～100 parts of quality solvents benzene, and is added dropwise to 8-10 part quality Phosphorus Oxychloride POCl
3600 parts of quality of solvent; At room temperature stir 1～2hr; Reaction solution is slowly added 2000 portions of quality frozen water, filtering-depositing, washing, drying are crossed silicagel column with ethyl acetate and 2: 8 developping agent of benzene volume ratio, get two pairs of anisidino of product (a) to phenyl aldehyde;
(2) with 25 parts of quality 4,4 '-dichloromethyl biphenyl, 25～30 parts of quality triphenylphosphines are dissolved in 160～200 parts of quality solvents, 150 ℃ of backflow 2.5-3.5hr obtain product (b), continue to add in reaction system 70～80 parts of quality products (a) behind the cool to room temperature, 25～30 parts of quality potassium tert.-butoxide/sodium tert-butoxides, stirred 9-11 hour, and added 50 parts of quality water again, stirred 5-10 minute; Evaporating solvent is crossed silicagel column with sherwood oil and 5: 5 developping agent of benzene volume ratio, gets product (c) two (two pairs of methyl oxyaniline phenyl vinyls) biphenyl;
(3) 8-10 part quality product (c) is added 100～120 parts of quality 47%HI, 70～80 parts of quality concentrated hydrochloric acids and 300～400 parts of quality water, 90-110 ℃ of temperature refluxed 15～20 hours, it is 7 with the NaOH aqueous solution with the reaction solution pH value that neutralizes that reaction finishes the back, use the organic solvent extraction organic phase, dry, boil off solvent, product is crossed silicagel column with ethyl acetate and 1: 9 developping agent of benzene volume ratio, gets product (d) two (two para hydroxybenzene amine phenyl vinyls) biphenyl;
(4) in 400～500 parts of quality of organic solvent of having dissolved 18-20 part quality product (d) and 16-32 part quality bromo alkyl alcohol, add 20-28 part quality K
2CO
3With 500 parts of quality ethyl acetate and 3000 parts of quality water extracted organic phase, drying is filtered, and boils off solvent, gets product two (two pairs of hydroxyl alkoxyl aniline phenyl vinyls) biphenyl behind 50 ℃ of following stirring 12hr;
(5) under the room temperature to having dissolved product 24-28 part quality two (two pairs of hydroxyl alkoxyl aniline phenyl vinyls) biphenyl, 7.5-8 add 21-23 part quality 1 in 200～250ml DMF solution of part quality methacrylic acid or vinylformic acid and 0.7-1.0 part quality 4-dimethylamino pyridine DMAP, 3-dicyclohexyl phosphinylidyne diimine DCC; At room temperature stir 9～11hr, add 2000～3000ml water then; Use the ethyl acetate extraction organic phase; Cross silicagel column with 8: 2 toluene-ethyl acetate behind the evaporating solvent, get product two (two (methyl) vinylformic acid oxyalkyl ester group aniline phenyl vinyl) biphenyl, or two (diacrylate oxyalkyl ester group aniline phenyl vinyl) biphenyl.
Method as claimed in claim 3 is characterized in that: the used bromo alkyl alcohol of step (4) comprises bromopropyl alcohol, bromo (different) butanols, bromine (different) amylalcohol, bromine (different) hexanol.
The organic solvent of step (3) usefulness comprises chloroform, ethyl acetate, ether, toluene; The organic solvent of step (4) usefulness comprises DMF or methyl alcohol, ethanol.
Prepare the method for compound cured film as mentioned above, wherein step is as follows:
(1) 1 mass parts two (two (methyl) vinylformic acid oxyalkyl ester group aniline phenyl vinyl) biphenyl and 4-6% mass parts st-yrax first/ether are dissolved in 40～60 parts of quality tetrahydrofuran (THF)s or other organic solvent, with the ito glass is substrate spin-coating film under the rotating speed of 3000r/min, after the 60-70 ℃ of drying treatment, obtain the rete that thickness is 50～200nm;
(2) with 256～300nm wavelength, the above ultraviolet lamp of 7W power shines 10～15min apart from rete 2～5cm place, obtains required cured film.
Aforesaid compound wherein contains other electroluminescent organic material layer in the application of preparation electroluminescent organic material layer on the cured film of such compound.
The application of aforesaid compound aspect preparation organic electroluminescent flat-panel monitor.
Adopted the material of above-claimed cpd and its preparation, major advantage of the present invention is:
1. institute's synthetic pentanoic styrylbiphenyl blue-ray organic electroluminescent material of containing enoate side group solvability before uncrosslinked is good, have good solution processing characteristics, and chemical property is stable, and enoate side group does not decompose under daylight illumination.
2. the pentanoic styrylbiphenyl blue-ray organic electroluminescent material that contains enoate side group is insoluble to organic solvent later at photo-crosslinking, is not subjected to the influence of upper solution spin coating.
3. the photo-crosslinking group is on the side group of pentanoic styrylbiphenyl molecule agent structure, and is very little to the luminescent properties influence of agent structure.
4. cost of material is cheap, reacts fairly simple, is fit to mass production.
Description of drawings
Fig. 1 is the general structure of diphenylamines substitutedstyrylbipcompounds compounds of the present invention;
Fig. 2 is the synthetic route chart of compound among the embodiment 1 (f);
Fig. 3 is the synthetic route chart of compound among the embodiment 2 (h);
Fig. 4 is the synthetic route chart of compound among the embodiment 3 (j).
Embodiment
Chemical reagent used among the embodiment is all available from Aldrich reagent company and Chinese Medicine main office, and reagent is analytical pure, uses preceding through conventional purifying, drying treatment.
Synthesizing of (1) two (diacrylate oxygen propyl ester base aniline phenyl vinyl) biphenyl
Two pairs of anisidino of 18 parts of quality are dissolved in the dry dimethyl formamide DMF of 70～100 parts of quality solvent to benzene, and are added dropwise to 8.43～9.97 parts of quality Phosphorus Oxychloride POCl
3600 parts of quality of dry dimethyl formamide solution.At room temperature stir 1～2hr.Reaction solution is slowly added 2000 portions of quality frozen water, filtering-depositing, washing, drying are crossed silicagel column with ethyl acetate and 2: 8 developping agent of benzene volume ratio, must product (a)---two pairs of anisidino are to 13～15 parts of quality of phenyl aldehyde.
With 25 parts of quality 4,4 '-dichloromethyl biphenyl, 25～30 parts of quality triphenylphosphines are dissolved in 160～200 parts of quality anhydrous dimethyl formamides, 153 ℃ of backflow 3hr obtain product (b), continue to add in reaction system 70～80 parts of quality products (b) behind the cool to room temperature, 25～30 parts of quality potassium tert.-butoxides, stirred 10 hours, and added 50 parts of quality water again, stirred 5 minutes.Evaporating solvent is crossed silicagel column with sherwood oil and 5: 5 developping agent of benzene volume ratio, gets product (c)---45～55 parts of quality of two (two pairs of methyl oxyaniline phenyl vinyls) biphenyl.
8.12 parts of quality products (c) are added 100～120 parts of quality 47%HI, 70～80 parts of quality concentrated hydrochloric acids and 300～400 parts of quality water, 100 ℃ of temperature refluxed 15～20 hours, it is 7 with 40%NaOH with the reaction solution pH value that neutralizes that reaction finishes the back, use the chloroform extraction organic phase, dry, boil off solvent, product is crossed silicagel column with ethyl acetate and 1: 9 developping agent of benzene volume ratio, gets product (d)---two (two para hydroxybenzene amine phenyl vinyls) 5～6 parts of quality of biphenyl.
In the DMF solution (400～500 parts of quality) that has dissolved product (d) (18.9 parts of quality) and 3-bromopropyl alcohol (16.7～20.9 parts of quality), add K
2CO
3(20.7～27.6 parts of quality).50 ℃ are stirred down behind the 12hr back with 500 parts of quality ethyl acetate and 3000 parts of quality water extracted organic phase, anhydrous magnesium sulfate drying, and filtration boils off solvent, gets product (e)---two (two pairs of propoxyl aniline phenyl vinyls) 13～16 parts of quality of biphenyl.
Under the room temperature to having dissolved product (e) (24.7 parts of quality), add 1 in 200～250 parts of quality dimethyl formamide solutions of vinylformic acid (7.57～7.93 parts of quality) and 4-dimethylamino pyridine DMAP (0.72～0.90 part of quality), 3-dicyclohexyl phosphinylidyne diimine DCC (21.5～22.6 parts of quality).At room temperature stir 9～11hr, add 2000～3000 parts of quality water then.Use the ethyl acetate extraction organic phase.Cross silicagel column with toluene-ethyl acetate (8: 2) behind the evaporating solvent, get product (f)---two (diacrylate oxygen propyl ester base aniline phenyl vinyl) 17～20 parts of quality of biphenyl.
Mass spectrum: m/e:1204.51 (100.0%), 1205.51 (84.1%), 1206.52 (34.6%), 1207.52 (11.0%)
Ultimate analysis: C, 75.33; H, 5.91; N, 2.55
(2) photo-crosslinking
2 parts of quality products (f) two (two pairs of vinylformic acid oxygen propyl ester base aniline phenyl vinyls) biphenyl and 4%～6% part of quality benzoin methyl ether (or Benzoin ethyl ether) initiator are dissolved in 40～60 parts of quality tetrahydrofuran (THF)s, with ITO is substrate spin-coating film under the rotating speed of 3000r/min, after 60 ℃ of drying treatment, obtaining thicknesses of layers is 50～200nm.
With hand-held ultraviolet lamp (256～300nm, 7W) 2～5cm apart from the irradiation 10～15min.With the continuous flushing membranes of 500 parts of quality tetrahydrofuran (THF)s surface 30 minutes, with the 365nm UV-irradiation, send bright blue light, the peak value of emission wavelength is at 483nm.Illustrating that the film after crosslinked is insoluble to solvent, be fixed on the substrate, is luminescent layer preferably.
Correspondingly, 2 parts of quality products (f) two (two pairs of vinylformic acid oxygen propyl ester base aniline phenyl vinyls) biphenyl and 4%～6% part of quality benzoin methyl ether (or Benzoin ethyl ether) initiator are dissolved in 40～60 parts of quality tetrahydrofuran (THF)s, with ITO is substrate spin-coating film under the rotating speed of 3000r/min, after 60 ℃ of drying treatment, obtaining thicknesses of layers is 50～200nm.Without ultraviolet light polymerization, with the continuous flushing membranes of 500 parts of quality tetrahydrofuran (THF)s surface after 30 minutes with the 365nm UV-irradiation, the ito glass surface does not have blue light to send, and illustrates that film is dissolved in solvent, is not fixed on the substrate.
As shown in Figure 3:
Synthesizing of (1) two (diacrylate oxygen isobutyl ester group aniline phenyl vinyl) biphenyl
In the DMF solution (400～500 parts of quality) that has dissolved product (d) (18.9 parts of quality) and bromo isopropylcarbinol (17.5～21.3 parts of quality), add K
2CO
3(20.7～27.6 parts of quality).50 ℃ are stirred down behind the 12hr back with 500 parts of quality ethyl acetate and 3000 parts of quality water extracted organic phase, anhydrous magnesium sulfate drying, and filtration boils off solvent, gets product (g)---two (two pairs of hydroxyl isobutoxy aniline phenyl vinyls) 13～16 parts of quality of biphenyl.
To having dissolved product (g) (26.1 parts of quality), add DCC (21.5～22.6 parts of quality) in 200～250 parts of quality dimethyl formamide solutions of vinylformic acid (7.57～7.93 parts of quality) and DMAP (0.72～0.90 part of quality) under the room temperature.At room temperature stir 9～11hr, add 2000～3000 parts of quality water then.Use the ethyl acetate extraction organic phase.Cross silicagel column with toluene-ethyl acetate (8: 2) behind the evaporating solvent, get product (h)---two (diacrylate oxygen isobutyl ester group aniline phenyl vinyl) 17.5～20 parts of quality of biphenyl.
Mass spectrum: m/e:1260.57 (100.0%), 1261.57 (87.3%), 1262.58 (40.6%), 1263.58 (13.1%)
Ultimate analysis: C, 76.06; H, 6.28; N, 2.51
(2) photo-crosslinking
2 parts of quality products (h) two (two pairs of vinylformic acid oxygen isobutyl ester group aniline phenyl vinyls) biphenyl and 4%～6% part of quality benzoin methyl ether (or Benzoin ethyl ether) initiator are dissolved in 40～60 parts of quality tetrahydrofuran (THF)s, with ITO is substrate spin-coating film under the rotating speed of 3000r/min, after 60 ℃ of drying treatment, obtaining thicknesses of layers is 50～200nm.
With hand-held ultraviolet lamp (256～300nm, 7W) 2～5cm apart from the irradiation 10～15min.With the continuous flushing membranes of 500 parts of quality tetrahydrofuran (THF)s surface 30 minutes, with the 365nm UV-irradiation, send bright blue light, the peak value of emission wavelength is at 480nm.Illustrating that the film after crosslinked is insoluble to solvent, be fixed on the substrate, is luminescent layer preferably.
Correspondingly, 2 parts of quality products (h) two (two pairs of vinylformic acid oxygen isobutyl ester group aniline phenyl vinyls) biphenyl and 4%～6% part of quality benzoin methyl ether (or Benzoin ethyl ether) initiator are dissolved in 40～60 parts of quality tetrahydrofuran (THF)s, with ITO is substrate spin-coating film under the rotating speed of 3000r/min, after 60 ℃ of drying treatment, obtaining thicknesses of layers is 50～200nm.Without ultraviolet light polymerization, with the continuous flushing membranes of 500 parts of quality tetrahydrofuran (THF)s surface after 30 minutes with the 365nm UV-irradiation, the ito glass surface does not have blue light to send, and illustrates that film is dissolved in solvent, is not fixed on the substrate.
Embodiment 3. 2 (dimethacrylate oxygen pentyl ester base aniline phenyl vinyl) biphenyl and photo-crosslinking cured product thereof
As shown in Figure 4:
Synthesizing of (1) two (dimethacrylate oxygen pentyl ester base aniline phenyl vinyl) biphenyl
In the DMF solution (400～500 parts of quality) that has dissolved product (d) (18.9 parts of quality) and 5-bromine amylalcohol (18.15～22.3 parts of quality), add K
2CO
3(20.7～27.6 parts of quality).50 ℃ are stirred down behind the 12hr back with 500 parts of quality ethyl acetate and 3000 parts of quality water extracted organic phase, anhydrous magnesium sulfate drying, and filtration boils off solvent, gets product (i)---two (two pairs of hydroxyl pentyloxy aniline phenyl vinyls) 14～17 parts of quality of biphenyl.
To having dissolved product (i) (27.5 parts of quality), add DCC (21.5～22.6 parts of quality) in 200～250 parts of quality dimethyl formamide solutions of methacrylic acid (9.0～9.47 parts of quality) and DMAP (0.72～0.90 part of quality) under the room temperature.At room temperature stir 9～11hr, add 2000～3000 parts of quality water then.Use the ethyl acetate extraction organic phase.Cross silicagel column with toluene-ethyl acetate (8: 2) behind the evaporating solvent, get product (j)---two (dimethacrylate oxygen pentyl ester base aniline phenyl vinyl) 17.5～20 parts of quality of biphenyl.
Mass spectrum: m/e:1372.7 (100.0%), 1373.7 (96.7%), 1374.7 (48.4%)
Ultimate analysis: C, 76.83; H, 7.21; N, 2.08
(2) photo-crosslinking
2 parts of quality products (j) two (two pairs of vinylformic acid oxygen pentyl ester base aniline phenyl vinyls) biphenyl and 4%～6% part of quality benzoin methyl ether (or Benzoin ethyl ether) initiator are dissolved in 40～60 parts of quality tetrahydrofuran (THF)s, with ITO is substrate spin-coating film under the rotating speed of 3000r/min, after 60 ℃ of drying treatment, obtaining thicknesses of layers is 50～200nm.
With hand-held ultraviolet lamp (256～300nm, 7W) 2～5cm apart from the irradiation 10～15min.With the continuous flushing membranes of 500 parts of quality tetrahydrofuran (THF)s surface 30 minutes, with the 365nm UV-irradiation, send bright blue light, the peak value of emission wavelength is at 481nm.Illustrating that the film after crosslinked is insoluble to solvent, be fixed on the substrate, is luminescent layer preferably.
Correspondingly, 2 parts of quality products (j) two (two pairs of vinylformic acid oxygen pentyl ester base aniline phenyl vinyls) biphenyl and 4%～6% part of quality benzoin methyl ether (or Benzoin ethyl ether) initiator are dissolved in 40～60 parts of quality tetrahydrofuran (THF)s, with ITO is substrate spin-coating film under the rotating speed of 3000r/min, after 60 ℃ of drying treatment, obtaining thicknesses of layers is 50～200nm.Without ultraviolet light polymerization, with the continuous flushing membranes of 500 parts of quality tetrahydrofuran (THF)s surface after 30 minutes with the 365nm UV-irradiation, the ito glass surface does not have blue light to send, and illustrates that film is dissolved in solvent, is not fixed on the substrate.
The above-mentioned description to embodiment is can understand and apply the invention for ease of those skilled in the art.The person skilled in the art obviously can easily make various modifications to these embodiment, and needn't pass through performing creative labour being applied in the General Principle of this explanation among other embodiment.Therefore, the invention is not restricted to the embodiment here, those skilled in the art should be within protection scope of the present invention for improvement and modification that the present invention makes according to announcement of the present invention.
Claims (8)
1. the diphenylamines substitutedstyrylbipcompounds compounds that is used for blue light material is characterized in that it being the diphenylamines substitutedstyrylbipcompounds compounds with enoate side group, and general structure is as follows:
Wherein R is the straight or branched alkyl of 2～6 carbon, R
1Be hydrogen or methyl.
2. compound as claimed in claim 1 is characterized in that this compounds comprises: two (diacrylate oxygen third/fourth/penta/own ester group aniline phenyl vinyl) biphenyl, two (diacrylate oxygen isobutyl/penta/own ester group aniline phenyl vinyl) biphenyl, two (dimethacrylate oxygen third/fourth/penta/own ester group aniline phenyl vinyl) biphenyl, two (dimethacrylate isobutyl/penta/hexyl ester group aniline phenyl vinyl) biphenyl.
3. the method for preparing compound as claimed in claim 1 is characterized in that synthesis step is as follows:
(1) two pairs of anisidino of 18～20 parts of quality is dissolved in 70～100 parts of quality solvents benzene, and is added dropwise to 8-10 part quality Phosphorus Oxychloride POCl
3600 parts of quality of solvent; At room temperature stir 1～2hr; Reaction solution is slowly added 2000 portions of quality frozen water, filtering-depositing, washing, drying are crossed silicagel column with ethyl acetate and 2: 8 developping agent of benzene volume ratio, get two pairs of anisidino of product (a) to phenyl aldehyde;
(2) with 25 parts of quality 4,4 '-dichloromethyl biphenyl, 25～30 parts of quality triphenylphosphines are dissolved in 160～200 parts of quality solvents, 150 ℃ of backflow 2.5-3.5hr obtain product (b), continue to add in reaction system 70～80 parts of quality products (a) behind the cool to room temperature, 25～30 parts of quality potassium tert.-butoxide/sodium tert-butoxides, stirred 9-11 hour, and added 50 parts of quality water again, stirred 5-10 minute; Evaporating solvent is crossed silicagel column with sherwood oil and 5: 5 developping agent of benzene volume ratio, gets product (c) two (two pairs of methyl oxyaniline phenyl vinyls) biphenyl;
(3) 8-10 part quality product (c) is added 100～120 parts of quality 47%HI, 70～80 parts of quality concentrated hydrochloric acids and 300～400 parts of quality water, 90-110 ℃ of temperature refluxed 15～20 hours, it is 7 with the NaOH aqueous solution with the reaction solution pH value that neutralizes that reaction finishes the back, use the organic solvent extraction organic phase, dry, boil off solvent, product is crossed silicagel column with ethyl acetate and 1: 9 developping agent of benzene volume ratio, gets product (d) two (two para hydroxybenzene amine phenyl vinyls) biphenyl;
(4) in 400～500 parts of quality of organic solvent of having dissolved 18-20 part quality product (d) and 16-32 part quality bromo alkyl alcohol, add 20-28 part quality K
2CO
3With 500 parts of quality ethyl acetate and 3000 parts of quality water extracted organic phase, drying is filtered, and boils off solvent, gets product two (two pairs of hydroxyl alkoxyl aniline phenyl vinyls) biphenyl behind 50 ℃ of following stirring 12hr;
(5) under the room temperature to having dissolved product 24-28 part two (two pairs of hydroxyl alkoxyl aniline phenyl vinyls) biphenyl, 7.5-8 add 21-23 part quality 1 in 200～250ml DMF solution of part quality methacrylic acid or vinylformic acid and 0.7-1.0 part quality 4-dimethylamino pyridine DMAP, 3-dicyclohexyl phosphinylidyne diimine DCC; At room temperature stir 9～11hr, add 2000～3000ml water then; Use the ethyl acetate extraction organic phase; Cross silicagel column with 8: 2 toluene-ethyl acetate behind the evaporating solvent, get product two (dimethacrylate oxyalkyl ester group aniline phenyl vinyl) biphenyl or two (diacrylate oxyalkyl ester group aniline phenyl vinyl) biphenyl.
4. method as claimed in claim 3 is characterized in that: the used bromo alkyl alcohol of step (4) comprises bromopropyl alcohol, bromo (different) butanols, bromine (different) amylalcohol, bromine (different) hexanol.
5. method as claimed in claim 3 is characterized in that:
Organic solvent in step (1) and (2) comprises dry DMF, orthodichlorobenzene;
The organic solvent of step (3) usefulness comprises chloroform, ethyl acetate, ether, toluene;
The organic solvent of step (4) usefulness comprises DMF, methyl alcohol, ethanol.
6. the method for preparing the described compound cured film of claim 1 is characterized in that step is as follows:
(1) 1 mass parts two (two (methyl) vinylformic acid oxyalkyl ester group aniline phenyl vinyl) biphenyl and 4-6% mass parts st-yrax first/ether are dissolved in 40～60 parts of quality tetrahydrofuran (THF)s, with the ito glass is substrate spin-coating film under the rotating speed of 3000r/min, after the 60-70 ℃ of drying treatment, obtain the rete that thickness is 50～200nm;
(2) with 256～300nm wavelength, the above ultraviolet lamp of 7W power shines 10～15min apart from rete 2～5cm place, obtains required cured film.
7. compound as claimed in claim 1 is characterized in that in the application of preparation electroluminescent organic material layer:
On the cured film of such compound, contain other electroluminescent organic material layer.
8. the application of compound as claimed in claim 1 aspect preparation organic electroluminescent flat-panel monitor.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100435427A CN101337899A (en) | 2007-07-06 | 2007-07-06 | Diphenylamines substitutedstyrylbiphenyl compounds for preparing blueing material and use thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CNA2007100435427A CN101337899A (en) | 2007-07-06 | 2007-07-06 | Diphenylamines substitutedstyrylbiphenyl compounds for preparing blueing material and use thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103012173A (en) * | 2012-12-11 | 2013-04-03 | 京东方科技集团股份有限公司 | Crosslinkable compound, preparation method thereof and luminescent device made from crosslinkable compound |
| EP3020768A1 (en) * | 2010-05-18 | 2016-05-18 | Milliken & Company | Optical brighteners and compositions comprising the same |
| CN109728204A (en) * | 2018-12-29 | 2019-05-07 | 上海天马微电子有限公司 | A method of preparing OLED organic function layer |
-
2007
- 2007-07-06 CN CNA2007100435427A patent/CN101337899A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3020768A1 (en) * | 2010-05-18 | 2016-05-18 | Milliken & Company | Optical brighteners and compositions comprising the same |
| CN103012173A (en) * | 2012-12-11 | 2013-04-03 | 京东方科技集团股份有限公司 | Crosslinkable compound, preparation method thereof and luminescent device made from crosslinkable compound |
| CN109728204A (en) * | 2018-12-29 | 2019-05-07 | 上海天马微电子有限公司 | A method of preparing OLED organic function layer |
| CN109728204B (en) * | 2018-12-29 | 2021-07-30 | 上海天马微电子有限公司 | Method for preparing organic functional layer of OLED |
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