CN1546477A - Method for preparing electron transport / hole barrier material and its electro-glow parts - Google Patents
Method for preparing electron transport / hole barrier material and its electro-glow parts Download PDFInfo
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Abstract
A process for making electron transmission / cavity barrier material and electro-redlight device by using compounds containing oxdiazole group as raw material, wherein a series of nonbranched conjugated oligomers are synthesized through organic metal catalytic reaction, the doping type red electroluminescent device containing the electron transmission / cavity barrier material and DCJTB luminescent material is also prepared, wherein the device comprises electrodes, a cavity transmission layer, an object luminescent material / subject material layer, an electron transmission / cavity barrier layer, and an electron transmission layer.
Description
Technical field
The present invention relates to an electron-like transmission/hole barrier materials and red electroluminescent preparation of devices method thereof, relate in particular to a class 2-(4-xenyl)-5-(4-tert-butyl-phenyl)-1,3, synthetic and the application and the relevant ruddiness device preparing process of 4-oxadiazole (PBD) derivative belong to electroluminescent novel material and technical field.
Technical background
In more than ten years, organic electroluminescent LED (OLEDs) is owing to its potential application in indicating meter of new generation and lighting engineering causes extensive attention in the past.Yet, now still there are some important challenges, comprise the raising of external quantum efficiency (EQE), the design of the novel material that purity of color is higher is with synthetic etc.In general, causing a low major cause of device EQE, is because the electric charge of luminescent material injects and transmits uneven causing.Because a lot of organic materialss are transporting holes effectively, so, under many circumstances, often additionally add one deck electric transmission/hole blocking layer in negative electrode one side in order to improve the luminous efficiency of device, with the blocking hole transmission, the compound luminescent layer zone that is limited in of current carrier.
BCP is 2, and 9-dimethyl-4,7-phenylbenzene-1,10-phenanthrolene are a kind of electric transmission/hole barrier materials that is widely used in the electroluminescent device, but its stability in device remains further to be improved.
1,3,4-oxadiazole (OXD) electron deficiency has low-down hole affinity, is unfavorable for hole transport, so OXD and derivative thereof are class ideal electric transmission/hole barrier materials that is widely studied at first.Wherein most typical is 2-(4-xenyl)-5-(4-tert-butyl-phenyl)-1,3,4-oxadiazole (PBD).Because PBD fusing point low (138 ℃), evaporated film has destroyed the homogeneity of film, thereby has caused the decay of organic luminescent device performance through the easy recrystallize in back after a while.PBD is entrained in the inert polymer matrix can suppresses its recrystallize to a certain extent, but doping techniques can not guarantee the stability of form fully, so in order to overcome the recrystallize problem, further improve its charge transport properties, generally will adopt the higher accumulation forceful electric power transmission/hole barrier materials of high-melting-point or second-order transition temperature.
Summary of the invention
The preparation method who the objective of the invention is to synthetic a kind of fusing point height, electric transmission/hole barrier materials that electron transport ability is strong, and the ruddiness preparation of devices method that adopts this material.
The present invention adopts the organo-metallic catalyzed reaction to synthesize an electron-like transmission/hole barrier materials, and the molecular structure of compound is as follows:
Wherein, X=O, Y=Z=N; Ar is a phenyl;
R ', R " be selected from following groups: R '=R respectively
1Ar
1, R "=R
2Ar
2
Ar
1And Ar
2Be respectively aryl.
R
1And R
2Be respectively the group that contains haloalkyl, aryl, halogenated aryl, halogen, fluorenyl or alkylaromatic hydrocarbon.
The above-claimed cpd synthetic method is as follows:
With 2,5-two-(4-bromophenyl)-1,3, the 4-oxadiazole is a module, Na
2CO
3Be alkali, the Pd (PPh of catalytic amount
3)
4, by the Suzuki reaction, with aryl boric acid coupling (boric acid: bromo-derivative mol ratio=2.0～3.0: 1),, obtain high-purity target product through column chromatography for separation or recrystallization.
Above-claimed cpd comprises following any derivative:
2,5-is two-4 '-(4 "-the trifluoromethyl-biphenyl base)-1,3, the 4-oxadiazole
2,5-is two-4 '-(4 "-the fluorine xenyl)-1,3, the 4-oxadiazole
2,5-is two-4 '-[4 "-(2,4 difluorobenzene base)-phenyl]-1,3, the 4-oxadiazole
2,5-is two-4 '-[4 "-(pentafluorophenyl group)-phenyl]-1,3, the 4-oxadiazole
2,5-is two-4 '-[4 "-(tetrahydropyrans-2-oxygen)-xenyl]-1,3, the 4-oxadiazole
2,5-is two-4 '-[4 "-(9, the 9-diaryl fluorene)-phenyl]-1,3, the 4-oxadiazole
2,5-is two-4 '-[4 "-volution fluorenes-phenyl]-1,3, the 4-oxadiazole
The synthetic method of said derivative is as follows:
With 2,5-two-(4-bromophenyl)-1,3, the 4-oxadiazole is a module, Na
2CO
3Be alkali, the Pd (PPh of catalytic amount
3)
4, by the Suzuki reaction, with aryl boric acid coupling (boric acid: bromo-derivative mol ratio=2.0～3.0: 1),, obtain corresponding product through column chromatography for separation or recrystallization.Aryl boric acid is respectively: 4-trifluoromethyl phenylo boric acid; The 4-fluorobenzoic boric acid; 2,4 difluorobenzene boric acid; Phenyl-pentafluoride boric acid; 4-(tetrahydropyrans-2-oxygen)-phenylo boric acid; 9,9-diaryl fluorene-2-boric acid, volution fluorenes-2-boric acid.
Suzuki of the present invention reaction be a kind of with palladium metal as catalyzer, under alkaline condition, the C-C linked reaction that takes place between aryl bromide and the aryl boric acid.
A kind of ruddiness preparation of devices method of using The compounds of this invention also is provided among the present invention, it at first is the first layer conductive layer, vacuum evaporation hole mobile material on conductive layer then, the adulterated luminescent layer of evaporation again, the compound among the present invention is made electric transmission/hole blocking layer on the evaporation then, follow evaporation one deck electron transfer layer, last evaporation second layer conductive layer.
The first layer conductive layer is produced on the substrate, and substrate is generally glass or plastics.
The first layer conductive layer is an anode, and second layer conductive layer is a negative electrode.Negative electrode preferably is made of the metal or the semi-transparent conductor that can produce reflection, is generally calcium, magnesium, aluminium, silver or alloy.Anode preferably (as polyaniline, PANI) is made of tin indium oxide (ITO) or transparent conductive polymer.
One deck hole transmission layer is arranged between the first layer conductive layer and luminescent layer; Between electric transmission/hole blocking layer and the second layer conductive layer one deck electron transfer layer is arranged; Luminescent layer is the adulterate body of red dye and AlQ (8-hydroxyquinoline aluminum) between hole transmission layer and electric transmission/hole blocking layer.
Device anode among the present invention is made on transparent substrate such as glass or plastics by evaporation by ITO or polyaniline (PANI).Negative electrode can be made of calcium, magnesium, aluminium, silver or alloy, and thickness is 10～200nm.
The anodic hole is injected and the electronics of transmission and negative electrode injects and transmission in order to improve, and makes charge energy compound well at luminescent layer, and the present invention adopts the multilayer device structure that comprises hole transmission layer, electric transmission and electric transmission/hole blocking layer.
The thickness of hole transport layer film is 30～200nm, can pass through vacuum thermal evaporation technology film forming on anode, by thermal evaporation luminescent layer is deposited on the hole transmission layer then.
Electric transmission/hole blocking layer is synthetic compound among the present invention, and the thickness of film is 10～200nm, deposits on the luminescent layer by thermal evaporation techniques.
The film thickness of luminescent layer is 10～100nm.
The film thickness of electron transfer layer is 10～200nm, and preferably 20～150nm can deposit to it on electric transmission/hole blocking layer by thermal evaporation.
The present invention adopts the organo-metallic catalyzed reaction to synthesize a class PBD derivative, and makes electric transmission/hole barrier materials with this compound and made adulterated ruddiness device.With respect to PBD, the material conjugate length that contains among the present invention increases, and fusing point greatly improves; The most important thing is that electron transport ability significantly strengthens, thereby improved the over-all properties of electroluminescent device.When being used for the red electroluminescent device, obtained gratifying result aspect the efficient of the device of making under brightness, current density and high current density, wherein a kind of over-all properties obviously is better than the BCP of present widespread use, thereby has obtained a kind of electric transmission/hole barrier materials and ruddiness device of excellent property.
Description of drawings
Fig. 1 is a current-voltage relation comparison diagram of making the ruddiness device that electric transmission/hole barrier materials makes with several compounds of synthetic among the present invention and BCP.
Fig. 2 is brightness-voltage relationship comparison diagram of making the ruddiness device that electric transmission/hole barrier materials makes with several compounds of synthetic among the present invention and BCP.
Fig. 3 makes the current efficiency-current relationship comparison diagram of ruddiness device behind trigger voltage that electric transmission/hole barrier materials is made with several compounds of synthetic among the present invention and BCP.
Fig. 4 is DCJTB (red dye) structural formula figure.
Fig. 5 is the structural formula figure of BCP (electric transmission/hole barrier materials).
Embodiment
Embodiment
In order to understand the content of patent of the present invention better, further specify technical scheme of the present invention below by concrete example and legend.
Example carries out according to the following steps:
Example 1,2,5-is two-4 '-(4 "-the trifluoromethyl-biphenyl base)-1,3, the preparation of 4-oxadiazole
4-bromo-benzoic acid ethyl ester (20mL) and hydrazine hydrate (27.5mL) back flow reaction in methyl alcohol (124mL) was cooled to crystallizing at room temperature after 16 hours, obtained needle-like white crystal 4-bromobenzene formyl hydrazine 25.3g, (productive rate is 87%).
1H?NMR(500MHz，DMSO，ppm)：δ7.7(d，2H)，δ7.6(d，2H)，δ9.8(s，1H)，δ4.54(s，2H)。
4-bromo-benzoyl chloride (11g) and 4-bromobenzene formyl hydrazine (10.5g) be the about 10h of back flow reaction (logical nitrogen in the reaction process) in the good pyridine (200mL) of distillation in advance; make solution be cooled to room temperature; crystallization goes out flaky white crystal; obtain product 4-bromo-benzoic acid-N-(4-benzoyl bromide) hydrazine 14.5g behind the suction filtration, (productive rate is 97%).
1H?NMR(500MHz，CDCl
3，ppm)：δ10.64(s，2H)，δ7.85(d，4H)，δ7.76(d，4H)。
4-bromo-benzoic acid-N-(4-benzoyl bromide) hydrazine (6.6g) and POCl
3(11mL) back flow reaction is about 10 hours, after reaction finishes with reaction solution to going in the frozen water, suction filtration obtains white crystal 2,5-two-(4-bromophenyl)-1,3,4-oxadiazole (6.2g), (productive rate is 98%).
1H?NMR(500MHz，CDCl
3，ppm)：δ8.00(d，4H)，δ7.68(d，4H)。
2,5-two-(4-bromophenyl)-1,3,4-oxadiazole (0.5g) and 4-(trifluoromethyl)-phenyl-boron dihydroxide (0.62g) stirring heating in 30ml toluene, and feed N
2, behind about 30min, add catalyst P d (PPh
3)
4(catalytic amount) and K
2CO
3Solution 4mL (2mol/L), backflow is spent the night.
Reaction mixture adds an amount of washing, the anhydrous MgSO of oil reservoir
4Revolve steaming after the drying, get brown solid, column chromatography for separation gets white solid product 0.54 gram, productive rate 80%.F.W.510，m.p.258.2℃，
1H?NMR(400MHz，CDCl
3，ppm)：δ7.74(d，4H)，δ7.77(d，4H)，δ7.96(m，4H)，δ8.26(m，4H)。
Example 2,2,5-is two-4 '-(4 "-the fluorine xenyl)-1,3, the preparation of 4-oxadiazole
2,5-two-(4-bromophenyl)-1,3,4-oxadiazole (0.5 gram) and 4-fluorophenyl boric acid (0.45 gram) stirring heating in 35mL toluene, and feed N
2Protection adds catalyst P d (PPh
3)
4(catalytic amount) and K
2CO
3Solution 3mL (2mol/L), backflow is spent the night.
Reaction mixture adds an amount of washing, the anhydrous MgSO of oil reservoir
4Revolve steaming after the drying,, get white solid product 0.46 gram, productive rate 85% through recrystallization.F.W.410，m.p.259.3℃，
1H?NMR(400MHz，CDCl
3，ppm)：δ7.18(d，4H)，δ7.62(m，4H)，δ7.72(d，4H)，δ8.22(d，4H)。
Example 3,2,5-is two-4 '-[4 "-(tetrahydropyrans-2-oxygen)-xenyl]-1,3, the preparation of 4-oxadiazole
P bromophenol (4g) and tosic acid (0.3g) add in the methylene dichloride (20mL) (nitrogen protection), with the ice-water bath cooling, add 3 with syringe, 4-dihydropyrane (3.7g) behind the stirring 15min.React after 8 hours, wash with water, revolve to steam and remove methylene dichloride, carry out column chromatography for separation then, obtain white powder solid p bromophenol tetrahydropyranyl ethers 5.6g, productive rate is 82%.
P bromophenol tetrahydropyranyl ethers (4.6g), inject anhydrous and oxygen-free tetrahydrofuran (THF) (40mL) with syringe, under-78 ℃, inject n-BuLi (about 14.5mL) with syringe, question response carries out injecting after 30 minutes methyl-borate (about 8mL), reacted about 2 hours down at-80 ℃, at room temperature make reaction proceed about 10 hours then.After reaction finished, about 8 hours of hydrolysis added methylene dichloride then up to the tangible two-phase of appearance, the water layer washed with dichloromethane, and the organic layer anhydrous magnesium sulfate drying, evaporate to dryness behind the suction filtration obtains white solid phenol boric acid tetrahydropyranyl ethers 1.3g, and productive rate is 49%.
1H?NMR(500MHz，CD
3COCD
3，ppm)：δ1.58-1.69(m，3H)，δ1.81-1.86(m，2H)，δ1.99-2.03(m，1H)，δ2.79-2.85(d，2H)，δ3.57-3.60(m，1H)，δ3.83-3.88(m，1H)，δ5.49(t，1H)，δ6.90-7.20(m，4H)，δ6.90-7.20(m，4H)，δ7.40-7.90(d，2H)。
Phenol boric acid tetrahydropyranyl ethers (1.34g) and 2,5-two-(4-bromophenyl)-1,3,4-oxadiazole (0.84g) is stirring and dissolving in toluene (40mL), logical nitrogen is after 15 minutes, adding four-[(triphenyl) phosphine] palladium (catalytic amount) and 4mL wet chemical (2mol/L), reaction refluxed 24 hours.The reaction solution separatory carries out column chromatography for separation after toluene layer revolved steaming, obtains white powder solid product 0.83g, and productive rate is 67%.F.W.550，
1H?NMR(500MHz，CDCl
3，ppm)：δ1.50-1.75(m，6H)，δ1.81-1.90(m，6H)，δ3.62-3.66(d，2H)，δ3.90-3.95(t，2H)，δ5.50(s，2H)，δ7.15-7.19(d，4H)，δ7.57-7.62(d，4H)，δ7.71-7.75(d，4H)，δ8.17-8.21(d，4H)。
Example 4,2,5-is two-4 '-[4 "-(2,4 difluorobenzene base)-phenyl]-1,3, the preparation of 4-oxadiazole
2,5-two-(4-bromophenyl)-1,3,4-oxadiazole (0.5 gram) and 2,4 difluorobenzene ylboronic acid (0.59g) stirring heating in 40mL toluene, and feed N
2, behind about 30min, add catalyst P d (PPh
3)
4(0.09g) and K
2CO
3Solution 4mL (2mol/L), backflow is spent the night.
Reaction mixture adds an amount of washing, the anhydrous MgSO of oil reservoir
4Revolve steaming after the drying, get brown solid, column chromatography for separation gets white solid product 0.24 gram, productive rate 40%.m.p.215.7℃，
1H?NMR(400MHz，CDCl
3，ppm)：δ6.94～7.25(m，4H)，δ7.47(m，2H)，δ7.61(d，4H)，δ8.23(d，4H)。
Example 5,2,5-is two-4 '-[4 "-volution fluorenes-phenyl]-1,3, the preparation of 4-oxadiazole
2-bromine fluorenes (10.0g) and Triton B (5mL, 40% methanol solution) are dissolved in the pyridine (50mL), and blowing air stirs under the room temperature and spends the night.After reaction mixture was used the acetate acidifying, acetic acid and pyridine were removed in underpressure distillation, add water in the residue, get glassy yellow product 2-bromine Fluorenone with ethyl alcohol recrystallization then.
The mixed solution of 2-bromo biphenyl (6.26g) and anhydrous THF (40mL) splashes in the flask that is placed with magnesium (0.63g), keeps little 30min that boils.2-bromine Fluorenone (6.5g) is added in the Grignard reagent for preparing with THF dissolving back, and stirring and refluxing is spent the night then.After reaction solution is cooled to room temperature, hydrolysis, separatory, the water layer extracted with diethyl ether, organic layer merges the anhydrous MgSO in back
4Drying, revolve steaming after, column chromatography for separation obtains pure hydrolysate (6.3g).This product is dissolved in the Glacial acetic acid of heat, addend drips concentrated hydrochloric acid, refluxes three hours, filters then, uses the washing with alcohol crystalline substance, gets white crystal 2-bromine volution fluorenes (6.0g).
1H?NMR(400MHz，CDCl
3，ppm)：δ7.80～7.86(m，3H)，δ7.70(d，1H)，δ7.48(m，1H)，δ7.36～7.40(m，3H)，δ7.13(m，3H)，δ6.84(d，1H)，δ6.72(m，3H)。
2-bromine volution fluorenes (1.2g) is dissolved among the anhydrous and oxygen-free THF, and-78 ℃ add n-BuLi (3mL, 1.6M in hexane) down, behind the stirring reaction 30min, add B (OMe)
3(1.5mL), reaction is spent the night; (2M 25mL) continues reaction 8h under the room temperature to add hydrochloric acid then.After reaction finished, water layer merged with the extracted with diethyl ether organic layer, uses anhydrous MgSO
4Drying is revolved steaming, and column chromatography for separation gets product synthesizing spiro fluorenes-2-boric acid 0.65g, productive rate 57%.
Volution fluorenes-2-boric acid (0.6g) and 2,5-pair-(4-bromophenyl)-1,3,4-oxadiazole (0.25g) is dissolved in the 30mL toluene, and feeds N
2Protection behind about 30min, adds Pd (PPh
3)
4(0.046g) and K
2CO
3(3mL, 2mol/L).Backflow is spent the night.Reaction mixture adds the suitable quantity of water separatory, water layer extracted with diethyl ether, the anhydrous MgSO of organic layer
4Revolve steaming after the drying, column chromatography for separation gets white solid product 0.26 gram, productive rate 47% then.m.p?376.3℃，
1H?NMR(400MHz，CDCl
3，ppm)：δ8.04(d，2H)，δ7.95(d，1H)，δ7.88～7.93(m，3H)，δ7.86(d，1H)，δ7.68(d，2H)，δ7.56(m，3H)，δ7.15(m，3H)，δ7.00(s，1H)，δ6.79(d，2H)，δ6.74(d，1H)。
The preparation of example 6, electroluminescent device
The film thickness of electric transmission/hole blocking layer is 40nm.Luminescent layer is the Alq3:DCJTB dopant material, and thickness is 20nm.It is the hole transmission layer (NPB) of 80nm that one layer thickness is arranged between luminescent layer and anode (ITO).Electron transfer layer is between electric transmission/hole blocking layer and negative electrode, and material therefor is AlQ, and film thickness is 50nm.All material all adopts the vacuum thermal evaporation technology to film.The structure of device is: ITO/NPB/AlQ:DCJTB/ electric transmission/hole blocking layer/Alq
3/ LiF/Al.
Claims (12)
1. compound that molecular formula is as follows:
Wherein, X=O, Y=Z=N; Ar is a phenyl;
R ', R " be selected from following groups: R '=R respectively
1Ar
1, R "=R
2Ar
2
Ar
1And Ar
2Be respectively aryl;
R
1And R
2Be respectively the group that contains haloalkyl, aryl, halogenated aryl, halogen, fluorenyl or alkylaromatic hydrocarbon.
2. the synthetic method as the said compound of claim 1 is as follows:
With 2,5-two-(4-bromophenyl)-1,3, the 4-oxadiazole is a module, Na
2CO
3Be that yellow soda ash is alkali, the Pd (PPh of catalytic amount
3)
4, promptly four-(triphenyl phosphorus) palladiums react by Suzuki, with the aryl boric acid coupling, and its mesoboric acid: bromo-derivative mol ratio=2.0～3.0: 1, through column chromatography for separation or recrystallization, obtain high-purity target product.
3. as claim 1,2 described compounds, it is characterized in that they are to contain any compound of following groups:
2,5-is two-4 '-(4 "-the trifluoromethyl-biphenyl base)-1,3, the 4-oxadiazole
2,5-is two-4 '-(4 "-the fluorine xenyl)-1,3, the 4-oxadiazole
2,5-is two-4 '-[4 "-(2,4 difluorobenzene base)-phenyl]-1,3, the 4-oxadiazole
2,5-is two-4 '-[4 "-(pentafluorophenyl group)-phenyl]-1,3, the 4-oxadiazole
2,5-is two-4 '-[4 "-(tetrahydropyrans-2-oxygen)-xenyl]-1,3, the 4-oxadiazole
2,5-is two-4 '-[4 "-(9, the 9-diaryl fluorene)-phenyl]-1,3, the 4-oxadiazole
R
3=H, F, CF
3Ar
3=phenyl
2,5-is two-4 '-[4 "-volution fluorenes-phenyl]-1,3, the 4-oxadiazole
4. as the preparation method of compound as described in the claim 3, it is characterized in that with 2,5-two-(4-bromophenyl)-1,3, the 4-oxadiazole is a module, Na
2CO
3Be alkali, the Pd (PPh of catalytic amount
3)
4, by the Suzuki reaction, with the aryl boric acid coupling, its mesoboric acid: bromo-derivative mol ratio=2.0～3.0: 1, through column chromatography for separation or recrystallization, obtain corresponding product; Aryl boric acid be respectively following any: 4-trifluoromethyl phenylo boric acid; The 4-fluorobenzoic boric acid; 2,4 difluorobenzene boric acid; Phenyl-pentafluoride boric acid; 4-(tetrahydropyrans-2-oxygen)-phenylo boric acid; 9,9-diaryl fluorene-2-boric acid, volution fluorenes-2-boric acid.
5. as the red electroluminescent preparation of devices method of compound-material as described in the claim 1,2,3, it is characterized in that evaporation conductive layer on base material, vacuum evaporation hole mobile material on conductive layer then, the adulterated luminescent layer of evaporation again, the any compound of evaporation claim 1～3 is as electric transmission/hole blocking layer then, follow the evaporation electron transfer layer, last evaporation second layer conductive layer.
6. ruddiness device as claimed in claim 5 is characterized in that the first layer conductive layer is plated on the residuite, and used matrix is glass or plastics.
7. ruddiness device as claimed in claim 5 is characterized in that the first layer conductive layer is an anode, and second layer conductive layer is a negative electrode.
8. ruddiness device as claimed in claim 7 is characterized in that anode is that tin indium oxide or PANI are that polyaniline constitutes by ITO.
9. as claim item 5 described ruddiness devices, it is characterized in that negative electrode is made of the metal or the semi-transparent conductor that can produce reflection, negative electrode is calcium, magnesium, aluminium, silver or alloy material
10. ruddiness device as claimed in claim 5, it is characterized in that luminescent layer is red light material DCJTB, i.e. 4-(dicyano the methyne)-2-tertiary butyl-6-(1,1,7,7-tetramethyl-julolidine-9-vinyl)-4H-pyrans and AlQ are the adulterate body of 8-hydroxyquinoline aluminum.
11. as claim item 5 described ruddiness devices, it is characterized in that hole transmission layer is NPB, i.e. N, N '-two (1-naphthyl)-N, N '-two phenyl-1,1 '-phenylbenzene-4,4 '-diamines.
12., it is characterized in that electron transfer layer is AlQ as claim item 5 described ruddiness devices.
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