CN107369775B - A kind of electroluminescent organic material and its organic luminescent device - Google Patents
A kind of electroluminescent organic material and its organic luminescent device Download PDFInfo
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K50/00—Organic light-emitting devices
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- H10K50/14—Carrier transporting layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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Abstract
The present invention provides a kind of electroluminescent organic material and its organic luminescent device, belongs to organic photoelectrical material technical field.Solve the technical problem for the luminescent properties differences such as organic photoelectrical material luminous efficiency is low in the prior art, driving voltage is higher, service life is short.Compared with prior art, of the invention based on a kind of electroluminescent organic material and organic luminescent device, the minimum 3.7V of driving voltage, it is a kind of excellent OLED material that luminous efficiency, which reaches as high as 19.1cd/A,.
Description
Technical field
The present invention relates to organic photoelectrical material technical fields, and in particular to a kind of electroluminescent organic material and its organic hair
Optical device.
Background technique
Having for first function admirable has been made from U.S. Kodak Company Tang C.W. and Vanslyke S.A. in 1987
Since organic electroluminescence devices, ORGANIC ELECTROLUMINESCENCE DISPLAYS causes the great interest of people since it has the advantage that.Fluorescence
Material is frequently used in luminescent layer as first generation luminescent material.In addition to this, phosphor material is as second generation light emitting host
Material is also by comparable attention.Such as Applied Physics letters, Vol 74, No.3, P442-444,1999；US
Patent 6097147,6306238 etc..The organic material used in OLED mainly have hole-injecting material, hole mobile material,
Luminescent material, electron transport material and electron injection material etc..
In the organic luminescent device prepared using phosphor material, in general, all holes or electron-transporting type master
The material doped guest materials of body forms luminescent layer, such as TAPC material is as the material of main part of luminescent layer.However, this kind of materials
As material of main part in use, exciton recombination region can selectively it is on the upper side certain on one side, so as to cause device efficiency and photochromic
Change, it is very serious that the energy between triplet may be caused to be quenched, cause luminous efficiency under high brightness to be roll-offed seriously.This
Outside, the driving voltage of device is higher, also not satisfactory.
Summary of the invention
In view of this, the purpose of the present invention is to provide a kind of electroluminescent organic materials.Using one kind of the present invention
The organic luminescent device of electroluminescent organic material preparation, has higher luminous efficiency and lower driving voltage.
Present invention firstly provides a kind of electroluminescent organic materials, have structural formula shown in formula I:
Wherein, R1, R2It is independent to be selected from hydrogen, substituted or unsubstituted C6-C50 aryl base, substituted or unsubstituted C7-C50
It is aralkyl, substituted or unsubstituted C6-C50 aryl amine, substituted or unsubstituted C6-C50 aryl phosphine, substituted or unsubstituted
Any one in C3-C50 heteroaryl.
Preferably, the R1, R2It is independent selected from hydrogen, it is substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted
C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl phosphine, replaces or does not take substituted or unsubstituted C6-C30 aryl amine
Any one in the C3-C30 heteroaryl in generation.
Preferably, a kind of electroluminescent organic material, any one in such as flowering structure:
The present invention also provides a kind of organic luminescent devices of electroluminescent organic material, including first electrode, second electrode
And the one or more organic compound layers being placed between two electrode, at least one organic compound layer include at least one
A kind of electroluminescent organic material.
Preferably, the organic compound layer includes hole injection layer, hole transmission layer, luminescent layer, hole blocking layer, electricity
At least one layer in sub- transport layer, electron injecting layer.
Beneficial effects of the present invention:
Compared with prior art, the organic luminescent device of a kind of electroluminescent organic material of the invention, luminous efficiency is most
High reachable 19.1cd/A, the minimum 3.7V of driving voltage are a kind of excellent OLED materials.
Specific embodiment
It is clearly and completely described below in conjunction with the technical solution of the embodiment of the present invention, it is clear that described implementation
Example is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, this field is common
Technical staff's every other embodiment obtained without making creative work belongs to the model that the present invention protects
It encloses.
Present invention firstly provides a kind of electroluminescent organic materials, have structural formula shown in formula I:
Wherein, R1, R2It is independent fragrant selected from hydrogen, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C7-C50
Alkyl, substituted or unsubstituted C6-C50 aryl amine, substituted or unsubstituted C6-C50 aryl phosphine, substituted or unsubstituted C3-
Any one in C50 heteroaryl.
Preferably, the R1, R2It is independent selected from hydrogen, it is substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted
C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl phosphine, replaces or does not take substituted or unsubstituted C6-C30 aryl amine
Any one in the C3-C30 heteroaryl in generation.
According to the present invention, the substituted aryl, substituted aryl amine, substituted aryl phosphine, replaces substituted aralkyl
Heteroaryl in, the substituent group can be selected from C1~C4 alkyl, C6-C18 aryl, C6-C18 aryloxy group or C6-C18 arylthio,
The number of the substituent group is preferably 1~3.Hetero atom in the heteroaryl is preferably O, S, N or P.
As an example, it is not particularly limited, a kind of electroluminescent organic material of the present invention is preferably selected from such as flowering structure
In any one:
A kind of electroluminescent organic material preparation method of the present invention:
Wherein, R1, R2It is independent fragrant selected from hydrogen, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C7-C50
Alkyl, substituted or unsubstituted C6-C50 aryl amine, substituted or unsubstituted C6-C50 aryl phosphine, substituted or unsubstituted C3-
Any one in C50 heteroaryl.
The present invention does not have particular/special requirement to the reaction condition of above-mentioned all kinds of reactions, with well known to those skilled in the art such
The normal condition of reaction.The present invention is not particularly limited the source of raw material employed in above-mentioned all kinds of reactions, can
Think commercial product or is prepared using preparation method well-known to those skilled in the art.Wherein, the R1, R2Selection
Same as above, details are not described herein.
The present invention also provides a kind of organic luminescent device of electroluminescent organic material, the organic luminescent device is ability
Organic luminescent device known to field technique personnel.Organic luminescent device of the present invention includes first electrode, the second electricity
Pole and the one or more organic compound layers being placed between two electrodes, at least one organic compound layer include at least one sheet
A kind of invention electroluminescent organic material.
The organic compound layer preferably includes hole injection layer, hole transmission layer, luminescent layer, hole blocking layer, electronics
At least one layer in transport layer and electron injecting layer preferably contains a kind of organic electroluminescence of the present invention in the luminescent layer
Luminescent material.
Embodiment 1: the preparation of compound 1
100mmol aniline is dissolved in solvent acetonitrile by Step1, under protection of argon gas, the trifluoroacetic acid of 1 equivalent is added,
It is added with stirring the styrene of 5 equivalents and the formalin of 5 equivalents.Stirring, there is yellow solid generation, and it is yellow to be heated to reflux
Color solid re-dissolves, and reacts 30min, is cooled to room temperature, and filters, washs filter cake with acetonitrile, product is chromatographed via column, obtains end
Product 41mmol compound 1.
Embodiment 2: the synthesis of compound 2
100mmol aniline is dissolved in solvent acetonitrile by Step1, under protection of argon gas, the trifluoroacetic acid of 1 equivalent is added,
It is added with stirring the formalin to bromstyrol and 5 equivalents of 5 equivalents.Stirring, has yellow solid generation, is heated to back
Stream yellow solid re-dissolves, and reacts 30min, is cooled to room temperature, and filters, washs filter cake with acetonitrile, product is chromatographed via column, is obtained
To finished product 41mmol compound 2-1.
Step2 takes the compound 2-1 of 41mmol, and the phenyl boric acid of 41mmol, 120mmol sodium carbonate, 0.4mmol tetra- is added
Triphenyl phosphorus palladium, toluene, the mixed solution of ethyl alcohol, water.Argon gas is replaced three times, 10h is reacted under reflux temperature, crude product is via column
Chromatography, obtains product 33mmol compound 2-2.
Step3 takes the 2-2 of 33mmol, and solvent methanol, 10% Pd/C is added, and argon gas is replaced three times, and hydrogen is replaced again
Three times.It is vigorously stirred reaction 3h at room temperature, is removed by filtration Pd/C, organic phase concentration chromatographs to obtain product 23mmolization via column
Close object 2.
Embodiment 3: the synthesis of compound 3
100mmol aniline is dissolved in solvent acetonitrile by Step1, under protection of argon gas, the trifluoroacetic acid of 1 equivalent is added,
It is added with stirring the formalin of bromstyrol and 5 equivalents between 5 equivalents.Stirring, has yellow solid generation, is heated to back
Stream yellow solid re-dissolves, and reacts 30min, is cooled to room temperature, and filters, washs filter cake with acetonitrile, product is chromatographed via column, is obtained
To finished product 41mmol compound 3-1.
Step2 takes the compound 3-1 of 41mmol, and the phenyl boric acid of 82mmol, 120mmol sodium carbonate, 0.4mmol tetra- is added
Triphenyl phosphorus palladium, toluene, the mixed solution of ethyl alcohol, water.Argon gas is replaced three times, 10h is reacted under reflux temperature, crude product is via column
Chromatography, obtains product 33mmol compound 3.
Embodiment 4: the synthesis of compound 9
100mmol aniline is dissolved in solvent acetonitrile by Step1, under protection of argon gas, the trifluoroacetic acid of 1 equivalent is added,
It is added with stirring the formalin to bromstyrol and 5 equivalents of 5 equivalents.Stirring, has yellow solid generation, is heated to back
Stream yellow solid re-dissolves, and reacts 30min, is cooled to room temperature, and filters, washs filter cake with acetonitrile, product is chromatographed via column, is obtained
To finished product 41mmol compound 2-1.
Step2 takes the 2-1 of 41mmol, and the carbazole of 41mmol, 120mmol potassium tert-butoxide, 0.4mmol Pd is added2
(dba)3, toluene, three times, addition 0.8mmol tri-tert-butylphosphine, argon gas displacement is three times, anti-under reflux temperature again for argon gas displacement
10h is answered, crude product is chromatographed via column, obtains product 33mmol compound 9-2.
Step3 takes the 9-2 of 33mmol, and solvent methanol, 10% Pd/C is added, and argon gas is replaced three times, and hydrogen is replaced again
Three times.It is vigorously stirred reaction 3h at room temperature, is removed by filtration Pd/C, organic phase concentration chromatographs to obtain product 23mmolization via column
Close object 9.
Embodiment 5: the synthesis of compound 10
100mmol aniline is dissolved in solvent acetonitrile by Step1, under protection of argon gas, the trifluoroacetic acid of 1 equivalent is added,
It is added with stirring the formalin of bromstyrol and 5 equivalents between 5 equivalents.Stirring, has yellow solid generation, is heated to back
Stream yellow solid re-dissolves, and reacts 30min, is cooled to room temperature, and filters, washs filter cake with acetonitrile, product is chromatographed via column, is obtained
To finished product 41mmol compound 3-1.
Step2 takes the compound 3-1 of 41mmol, and the carbazole of 41mmol, 120mmol potassium tert-butoxide, 0.4mmol is added
Pd2(dba)3, toluene, three times, addition 0.8mmol tri-tert-butylphosphine, argon gas is replaced three times, under reflux temperature again for argon gas displacement
10h is reacted, crude product is chromatographed via column, obtains product 33mmol compound 10-2.
Step3 takes the 10-2 of 33mmol, and solvent methanol, 10% Pd/C is added, and argon gas is replaced three times, and hydrogen is set again
It changes three times.It is vigorously stirred reaction 3h at room temperature, is removed by filtration Pd/C, organic phase concentration chromatographs to obtain product 23mmol via column
Compound 10.
Embodiment 6: the synthesis of compound 26
100mmol aniline is dissolved in solvent acetonitrile by Step1, under protection of argon gas, the trifluoroacetic acid of 1 equivalent is added,
It is added with stirring the formalin to bromstyrol and 5 equivalents of 5 equivalents.Stirring, has yellow solid generation, is heated to back
Stream yellow solid re-dissolves, and reacts 30min, is cooled to room temperature, and filters, washs filter cake with acetonitrile, product is chromatographed via column, is obtained
To finished product 41mmol compound 2-1.
Step2 takes the freshly prepd magnesium chips of 90mmol, is added in ether, and 41mmol compound 2- is added under nitrogen protection
1, it is heated to flow back, reacts 0.5h.Reaction solution is cooled to -10 DEG C.It is slowly added to phosphorus trichloride, after adding, is warming up to room temperature
The reaction was continued 0.5h.After the reaction was completed, water quenching reaction is added.Reaction solution is extracted with ether, dries, be concentrated, column excessively is produced
Product 18mmol compound 26.
Embodiment 7: the synthesis of compound 30
100mmol aniline is dissolved in solvent acetonitrile by Step1, under protection of argon gas, the trifluoroacetic acid of 1 equivalent is added,
It is added with stirring the formalin of bromstyrol and 5 equivalents between 5 equivalents.Stirring, has yellow solid generation, is heated to back
Stream yellow solid re-dissolves, and reacts 30min, is cooled to room temperature, and filters, washs filter cake with acetonitrile, product is chromatographed via column, is obtained
To finished product 41mmol compound 3-1.
Step2 takes the compound 3-1 of 41mmol, is added the phenol of 41mmol, 120mmol potassium tert-butoxide, 4mmol CuI,
DMF, argon gas are replaced three times, and 8mmol woods phenanthroline is added, and argon gas displacement three times, reacts 6h, crude product warp again under reflux temperature
It is chromatographed by column, obtains product 33mmol compound 30-2.
Step3 takes the compound 30-2 of 33mmol, and solvent methanol, 10% Pd/C is added, and argon gas is replaced three times, again
Hydrogen is replaced three times.It is vigorously stirred reaction 3h at room temperature, is removed by filtration Pd/C, organic phase concentration chromatographs to obtain product via column
23mmol compound 30.
Embodiment 8: the synthesis of compound 32
100mmol aniline is dissolved in solvent acetonitrile by Step1, under protection of argon gas, the trifluoroacetic acid of 1 equivalent is added,
It is added with stirring the formalin to bromstyrol and 5 equivalents of 5 equivalents.Stirring, has yellow solid generation, is heated to back
Stream yellow solid re-dissolves, and reacts 30min, is cooled to room temperature, and filters, washs filter cake with acetonitrile, product is chromatographed via column, is obtained
To finished product 41mmol compound 2-1.
Step2 takes the freshly prepd magnesium chips of 90mmol, is added in ether, and 41mmol compound 2- is added under nitrogen protection
1, it is heated to flow back, reacts 0.5h.Reaction solution is cooled to -80 DEG C.It is slowly added to carbonyl dimidazoles CDI, at this temperature instead
Answer 0.5h.It is warming up to room temperature the reaction was continued 1h.After the reaction was completed, water quenching reaction is added.Reaction solution is extracted with ethyl acetate, does
Dry, concentration, column excessively obtain product 25mmol compound 32.
Embodiment 9: the synthesis of compound 37
100mmol aniline is dissolved in solvent acetonitrile by Step1, under protection of argon gas, the trifluoroacetic acid of 1 equivalent is added,
It is added with stirring the formalin to bromstyrol and 5 equivalents of 5 equivalents.Stirring, has yellow solid generation, is heated to back
Stream yellow solid re-dissolves, and reacts 30min, is cooled to room temperature, and filters, washs filter cake with acetonitrile, product is chromatographed via column, is obtained
To finished product 41mmol compound 2-1.
Step2 takes the compound 2-1 of 41mmol, and the pyridine boronic acid of 41mmol, 120mmol sodium carbonate, 0.4mmol is added
Four triphenyl phosphorus palladiums, toluene, the mixed solution of ethyl alcohol, water.Argon gas is replaced three times, reacts 10h under reflux temperature, crude product via
Column chromatography, obtains product 33mmol compound 37-2.
Step3 takes 33mmol compound 37-2, and solvent methanol, 10% Pd/C is added, and argon gas is replaced three times, again hydrogen
Gas is replaced three times.It is vigorously stirred reaction 3h at room temperature, is removed by filtration Pd/C, organic phase concentration chromatographs to obtain product via column
23mmol compound 37.
Embodiment 10: the synthesis of compound 45
100mmol aniline is dissolved in solvent acetonitrile by Step1, under protection of argon gas, the trifluoroacetic acid of 1 equivalent is added,
It is added with stirring the formalin to bromstyrol and 5 equivalents of 5 equivalents.Stirring, has yellow solid generation, is heated to back
Stream yellow solid re-dissolves, and reacts 30min, is cooled to room temperature, and filters, washs filter cake with acetonitrile, product is chromatographed via column, is obtained
To finished product 41mmol compound 2-1.
Step2 takes the compound 2-1 of 41mmol, and 9, the 9- dimethyl -9H- fluorenes -2- boric acid of 41mmol, 120mmol is added
Sodium carbonate, tetra- triphenyl phosphorus palladium of 0.4mmol, toluene, the mixed solution of ethyl alcohol, water.Argon gas is replaced three times, is reacted under reflux temperature
10h, crude product are chromatographed via column, obtain product 33mmol compound 45-2.
Step3 takes 45mmol 45-2, and solvent methanol, 10% Pd/C is added, and argon gas is replaced three times, and hydrogen is replaced again
Three times.It is vigorously stirred reaction 3h at room temperature, is removed by filtration Pd/C, organic phase concentration chromatographs to obtain product 23mmolization via column
Close object 45.
A kind of FD-MS value for electroluminescent organic material that the embodiment of the present invention is prepared is shown in Table 1.
The compound FD-MS value of 1 embodiment of the present invention of table preparation
Compare Application Example 1:
Taking transparent glass is anode, dries after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, upper
Vacuum evaporation NPB is stated in anode grid substrate as hole transmission layer, evaporation rate 0.1nm/s, evaporation thickness 70nm.In hole
Vacuum evaporation TAPC/FIrpic is steamed as luminescent layer, doping concentration 10wt%, evaporation rate 0.005nm/s in transport layer
Plating is with a thickness of 30nm.Vacuum evaporation Alq on the light-emitting layer3As electron transfer layer, evaporation rate 0.01nm/s, evaporation thickness
For 50nm.Cathode is used as vacuum evaporation Al layers on the electron transport layer, with a thickness of 200nm.
Application Example 1:
Taking transparent glass is anode, dries after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, upper
Vacuum evaporation NPB is stated in anode grid substrate as hole transmission layer, evaporation rate 0.1nm/s, evaporation thickness 70nm.In hole
Vacuum evaporation compound 1/FIrpic is as luminescent layer, doping concentration 10wt%, evaporation rate 0.005nm/ in transport layer
S, evaporation thickness 30nm.Vacuum evaporation Alq on the light-emitting layer3As electron transfer layer, evaporation rate 0.01nm/s, vapor deposition
With a thickness of 50nm.Cathode is used as vacuum evaporation Al layers on the electron transport layer, with a thickness of 200nm.
Application Example 2:
Change the compound 1 in Application Example 1 into compound 2.The luminescent properties for measuring the device, the results are shown in Table 2.
Application Example 3:
Change the compound 1 in Application Example 1 into compound 3.The luminescent properties for measuring the device, the results are shown in Table 2.
Application Example 4:
Change the compound 1 in Application Example 1 into compound 9.The luminescent properties for measuring the device, the results are shown in Table 2.
Application Example 5:
Change the compound 1 in Application Example 1 into compound 10.The luminescent properties for measuring the device, the results are shown in Table 2.
Application Example 6:
Change the compound 1 in Application Example 1 into compound 26.The luminescent properties for measuring the device, the results are shown in Table 2.
Application Example 7:
Change the compound 1 in Application Example 1 into compound 30.The luminescent properties for measuring the device, the results are shown in Table 2.
Application Example 8:
Change the compound 1 in Application Example 1 into compound 32.The luminescent properties for measuring the device, the results are shown in Table 2.
Application Example 9:
Change the compound 1 in Application Example 1 into compound 37.The luminescent properties for measuring the device, the results are shown in Table 2.
Application Example 10:
Change the compound 1 in Application Example 1 into compound 45.The luminescent properties for measuring the device, the results are shown in Table 2.
Measure embodiment 1: the luminescent properties of contrast sample and sample
Contrast sample and sample are to evaluate luminous efficiency and driving voltage, knot using Keithley SMU235, PR650
Fruit is listed in Table 2 below:
The characteristics of luminescence of the luminescent device of 2 embodiment of the present invention of table preparation
Above as can be seen that a kind of electroluminescent organic material of the invention is applied in an organic light emitting device, hair
Light efficiency reaches as high as 19.1cd/A, and the minimum 3.7V of driving voltage, the biggish luminous efficiency for improving device is that performance is good
Good luminous organic material.
Although the present invention has carried out special description with exemplary embodiment, but it is understood that without departing from claim
Defined by the case where spirit and scope of the invention, those of ordinary skill in the art can carry out various forms and details to it
On change.
Claims (5)
1. a kind of electroluminescent organic material, general structure are shown in formula I:
Wherein, R1, R2It is independent to be selected from hydrogen, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C7-C50 aralkyl
Base, substituted or unsubstituted C6-C50 aryl amine, substituted or unsubstituted C6-C50 aryl phosphine, substituted or unsubstituted C3-C50
Any one in heteroaryl.
2. a kind of electroluminescent organic material according to claim 1, which is characterized in that R1, R2It is independent to be selected from hydrogen, take
Generation or unsubstituted C6-C30 aryl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl amine,
Any one in substituted or unsubstituted C6-C30 aryl phosphine, substituted or unsubstituted C3-C30 heteroaryl.
3. a kind of electroluminescent organic material according to claim 1, which is characterized in that any in such as flowering structure
It is a kind of:
4. a kind of organic luminescent device of electroluminescent organic material, including first electrode, second electrode and it is placed in two electricity
One or more organic compound layers between pole, which is characterized in that at least one organic compound layer include it is at least one such as
A kind of electroluminescent organic material described in claims 1 to 3 any one.
5. a kind of organic luminescent device of electroluminescent organic material according to claim 4, which is characterized in that described to have
Machine compound layer include hole injection layer, hole transmission layer, luminescent layer, hole blocking layer, electron transfer layer, in electron injecting layer
At least one layer.
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| US20040131648A1 (en) * | 2002-10-24 | 2004-07-08 | The Procter & Gamble Company | Nuclear hormone receptor compounds, products and methods employing same |
| WO2006070817A1 (en) * | 2004-12-28 | 2006-07-06 | Nagoya Industrial Science Research Institute | ORGANOBORON π-ELECTRON-SYSTEM COMPOUNDS AND INTERMEDIATE THEREFOR |
| US20090281322A1 (en) * | 2008-05-08 | 2009-11-12 | Allergan, Inc. | THERAPEUTICALLY USEFUL SUBSTITUTED 1,7-DIPHENYL-1,2,3,5,6,7-HEXAHYDROPYRIDO[3,2,1-Ij]QUINOLINE COMPOUNDS |
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| CN105566320A (en) * | 2014-11-10 | 2016-05-11 | 吉林奥来德光电材料股份有限公司 | Pyridine-quinoline derivative, preparation method and organic light-emitting device |
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