CN108440385A - A kind of organic photoelectrical material and its application - Google Patents

A kind of organic photoelectrical material and its application Download PDF

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Publication number
CN108440385A
CN108440385A CN201810186858.XA CN201810186858A CN108440385A CN 108440385 A CN108440385 A CN 108440385A CN 201810186858 A CN201810186858 A CN 201810186858A CN 108440385 A CN108440385 A CN 108440385A
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organic
organic electroluminescence
electroluminescence device
layer
photoelectrical material
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张善国
郑敬玉
林存生
王明佼
邢宗仁
石宇
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Valiant Co Ltd
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Valiant Co Ltd
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Abstract

The invention belongs to organic photoelectrical material field more particularly to a kind of organic photoelectrical material and its application, the organic photoelectrical material includes molecular structure shown in meeting formula (1)：Wherein, at least one of N, S, O C are contained in R12‑60One kind in aromatic heterocyclic base, organic photoelectrical material of the present invention is applied in the luminescent layer of organic electroluminescence device, to improve the maximum current efficiency of organic electroluminescence device, the bright voltage that opens of organic electroluminescence device is reduced, and so that the spectral coverage for the visible light that organic electroluminescence device is sent out is wider.

Description

A kind of organic photoelectrical material and its application
Technical field
The invention belongs to organic photoelectrical material field more particularly to a kind of organic photoelectrical material and its applications.
Background technology
Organic electroluminescent LED (Organic Light Emitting diode, OLED) due to self-luminous, The characteristics such as wide viewing angle, quick response and manufacture craft be simple, are known as 21 century most promising " illusion " display technology. The electroluminescent mechanism of OLED be electrons and holes respectively from anode and cathode injection after, by the two interelectrode organic work(of multilayer Ergosphere in light emitting molecule combine form exciton, exciton radiative decay and shine.According to the difference of luminous mechanism, can be divided into glimmering Two kinds of optical device and phosphorescent devices.
1998, the Forrest groups of Princeton university are put forward for the first time was applied to organic electroluminescence by phosphorescent coloring Luminescent device breaches the limitation that device internal quantum efficiency is less than 25%, theoretically internal quantum efficiency is made to have reached 100%, from And the frontier of Based on Organic Electrophosphorescence is started.In the same year, T.R.Hebner etc., which has been invented, prepares organic electroluminescence device Ink-jet printing, this provides the possibility of bigger for organic electroluminescence device from study direction market.2012, C.Adachi reports one kind on Nature and is based on thermal activation delayed fluorescence (TADF) mechanism, realizes the fluorescence device of High Efficiency Luminescence Part brings new direction for the preparation of high efficiency fluorescent device.It is needed in TADF materials with electron donor (abbreviation D) and electricity Sub- receptor (abbreviation A), the D-A type structure thus formed can realize the molecular structure requirement of delayed fluorescence.
The different function film layer and photoelectric characteristic demand of industry application requirement and OLED for current OLED, it is necessary to Selection is more suitable for, and photoelectric functional material with high performance either combination of materials could realize high efficiency, the long-life of OLED With the overall characteristic of low-voltage.For current OLED shows the actual demand of Lighting Industry, the light in OLED is applied at present The development of sulfate ferroelectric functional material is also far from enough, lags behind the requirement of panel manufacturing enterprise, as material enterprise development higher performance The exploitation of organic functional material be particularly important.
Invention content
In order to solve the above-mentioned technical problem the present invention provides a kind of organic photoelectrical material and its application, the organic photoelectric material Material can be applied in the luminescent layer of organic electroluminescence device, to improve the maximum current effect of organic electroluminescence device Rate, reduces the bright voltage that opens of organic electroluminescence device, and makes the visible light that organic electroluminescence device sent out Spectral coverage is wider.
The technical solution that the present invention solves above-mentioned technical problem is as follows：A kind of organic photoelectrical material, including meeting formula (1) institute The molecular structure shown：
Wherein, at least one of N, S, O C are contained in R12-60One kind in aromatic heterocyclic base.
Further, the one kind of the R in following structures：
Wherein * is the connection site with parent.
The present invention provides a kind of application of organic photoelectrical material in organic electroluminescence device.
A kind of organic electroluminescence device provided by the invention, at least one layer of functional layer, which contains, described in any one of the above embodiments to be had Machine photoelectric material.
Organic electroluminescence device of the present invention includes luminescent layer, and the luminescent layer contains above-mentioned organic photoelectrical material.
The present invention also provides a kind of illumination or display elements, including organic electroluminescence device described above.
The beneficial effects of the invention are as follows：Organic photoelectrical material provided by the present invention has indoles and naphthalenone structure, and right It carries out the modification of chemical group so that the organic photoelectrical material has excellent fluorescent emission ability, suitable molecular entergy level It with good thin film stability, applies in field of organic electroluminescence, which is applied to as dopant material Luminescent layer in organic electroluminescence device has reduced to improve the maximum current efficiency of organic electroluminescence device Organic electroluminescence devices open bright voltage, and make the spectral coverage for the visible light that organic electroluminescence device sent out It is relatively wide.
As the example of organic photoelectrical material, following compound 1-51 is now enumerated, wherein it should be noted that, following chemical combination Object is the representative structure for meeting spirit of that invention and principle, and the concrete structure for enumerating following compound is intended merely to preferably solve The present invention is released, is not limitation of the present invention.Concrete structure is as follows：
Organic electroluminescence device provided by the invention, including cathode, anode and luminescent layer, the luminescent layer are located at anode Between cathode, wherein the luminescent layer is by including that organic photoelectrical material provided by the present invention prepares.
In addition, in organic electroluminescence device, it may also include hole injection layer, hole transmission layer, electron transfer layer and electricity Sub- implanted layer, wherein hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer be respectively positioned on cathode and Between anode, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injection have been sequentially stacked on anode Layer.
In organic electroluminescence device, anode is preferably tin indium oxide (abbreviation ITO) electro-conductive glass, and hole injection layer is preferred Hat-CN is prepared, and the preferred NPB of hole transmission layer is prepared, and luminescent layer material preferably provided by the present invention and mCP are total With preparing, electron transfer layer is prepared by TPBI, and electron injecting layer is prepared by LiF, the preferred Al of cathode, wherein NPB, mCP and TPBI are as follows.
In organic electroluminescence device, each functional layer is not limited to using above-mentioned mentioned material, these materials It can be replaced with other materials, if hole transmission layer can be prepared by TAPC, electron transfer layer can be prepared by TpPYPB It obtains, wherein TAPC and TpPYPB are as follows：
In above-mentioned organic electroluminescence device, each film layer, that is to say, that hole transmission layer, luminescent layer, electron transfer layer Film can be made in the corresponding material of each film layer by the methods of vapour deposition method, spin-coating method or casting method with electron injecting layer It is formed.In addition, in order to each film layer material film and be easily obtained uniform film layer, at the same time, be not easy to generate needle Hole, preferably vacuum vapour deposition.When selecting vacuum vapour deposition, the wherein temperature of heating temperature, vacuum degree, evaporation rate and substrate Conventional selection can be carried out according to actual demand.It is easily obtained when selecting vacuum vapour deposition by corresponding material film uniformly Film layer, and be not easy to generate pin hole.
The preparation method of organic photoelectrical material provided by the invention containing indoles and naphthalene ketone derivant structure, wherein with chemical combination For the preparation method of object 41, reaction route is as follows:
Description of the drawings
Fig. 1 is the structural schematic diagram of the organic electroluminescence device prepared by the present invention.
In attached drawing, the component representated by each label is as follows：
1, transparent substrate layer, 2, transparent electrode layer, 3, hole injection layer, 4, hole transmission layer, 5, luminescent layer, 6, electronics passes Defeated layer, 7, electron injecting layer, 8, cathode.
Specific implementation mode
The principles and features of the present invention are described below, and the given examples are served only to explain the present invention, is not intended to limit Determine the scope of the present invention.
Compound prepares embodiment
Embodiment 1
The synthesis of compound 1：
Take 9- ethyls -6,6,8- trimethyl -5H- benzos [b] carbazole -11 (6H) -one (3.03g, 10.0mmol), 4- bromo- N, N- diphenyl aniline (3.56g, 11.0mmol), sodium tert-butoxide (4.93g, 50.0mmol) are dissolved in 100mL toluene, and nitrogen is protected 0.5h is protected, tetrakis triphenylphosphine palladium (1.16g, 1.0mmol) is added, is warming up to 115 DEG C, insulation reaction 6.0h.After completion of the reaction It is cooled to room temperature, is poured into 100g saturated sodium-chloride water solutions, is layered, saturated sodium-chloride water solution washs organic phase, dry, Desolventizing obtains yellow-brown solid 6.6g.It is recrystallized using n-hexane, obtains off-white powder particle (4.6g, yield 85%). The compound, molecular formula C are identified using DEI-MS39H34N2O, detected value [M+1]+=547.19, calculated value 546.27.
Embodiment 2
The synthesis of compound 7：
Take 9- ethyls -6,6,8- trimethyl -5H- benzos [b] carbazole -11 (6H) -one (3.03g, 10.0mmol), 5,5'- ((4- bromophenyls) ammonia diyl) two m-dicyanobenzenes (4.67g, 11.0mmol), sodium tert-butoxide (4.93g, 50.0mmol) are dissolved in In 100mL toluene, tetrakis triphenylphosphine palladium (1.16g, 1.0mmol) is added in nitrogen protection 0.5h, is warming up to 115 DEG C, heat preservation is anti- Answer 6.0h.It is cooled to room temperature after completion of the reaction, pours into 100g saturated sodium-chloride water solutions, is layered, saturated sodium-chloride is water-soluble Liquid washs organic phase, dry, and desolventizing obtains yellow-brown solid 6.9g.It is recrystallized using n-hexane, obtains off-white powder Grain (4.8g, yield 75%).The compound, molecular formula C are identified using DEI-MS43H30N6O, detected value [M+1]+= 647.30 calculated value 646.25.
Embodiment 3
The synthesis of compound 11：
Take 9- ethyls -6,6,8- trimethyl -5H- benzos [b] carbazole -11 (6H) -one (3.03g, 10.0mmol), N- (4- Bromophenyl)-N- (dibenzo [b, d] furans -3- bases) dibenzo [b, d] furans -3- ammonia (5.53g, 11.0mmol), sodium tert-butoxide (4.93g, 50.0mmol) is dissolved in 100mL toluene, nitrogen protection 0.5h, addition tetrakis triphenylphosphine palladium (1.16g, 1.0mmol), 115 DEG C are warming up to, insulation reaction 6.0h.It is cooled to room temperature after completion of the reaction, pours into 100g saturated sodium-chloride water In solution, layering, saturated sodium-chloride water solution washs organic phase, dry, and desolventizing obtains sepia solid 7.6g.Using just oneself Alkane recrystallizes, and obtains sepia solid particle (5.9g, yield 81%).The compound, molecular formula are identified using DEI-MS C43H30N6O, detected value [M+1]+=727.51, calculated value 726.29.
Embodiment 4
The synthesis of compound 16：
Take 9- ethyls -6,6,8- trimethyl -5H- benzos [b] carbazole -11 (6H) -one (3.03g, 10.0mmol), N, N- connection (4- (9H- carbazole -9- bases) phenyl) -4- bromanilines (7.18g, 11.0mmol), sodium tert-butoxide (4.93g, 50.0mmol) are dissolved in In 100mL toluene, tetrakis triphenylphosphine palladium (1.16g, 1.0mmol) is added in nitrogen protection 0.5h, is warming up to 115 DEG C, heat preservation is anti- Answer 6.0h.It is cooled to room temperature after completion of the reaction, pours into 100g saturated sodium-chloride water solutions, is layered, saturated sodium-chloride is water-soluble Liquid washs organic phase, dry, and desolventizing obtains sepia solid 9.2g.It is recrystallized using n-hexane, obtains sepia solid Grain (6.6g, yield 76%).The compound, molecular formula C are identified using DEI-MS63H48N4O, detected value [M+1]+= 877.28 calculated value 876.38.
Embodiment 5
The synthesis of compound 41：
Take 9- ethyls -6,6,8- trimethyl -5H- benzos [b] carbazole -11 (6H) -one (3.03g, 10.0mmol), 2- (4- Bromophenyl) -4,6- diphenyl -1,3,5-triazines (4.26g, 11.0mmol), sodium tert-butoxide (4.93g, 50.0mmol) be dissolved in In 100mL toluene, tetrakis triphenylphosphine palladium (1.16g, 1.0mmol) is added in nitrogen protection 0.5h, is warming up to 115 DEG C, heat preservation is anti- Answer 6h.It is cooled to room temperature after completion of the reaction, pours into 100g saturated sodium-chloride water solutions, is layered, saturated sodium-chloride water solution Organic phase is washed, dry, desolventizing obtains greenish yellow solid 6.6g.It is recrystallized using n-hexane, obtains off-white powder particle (5.55g, yield 91%).The compound, molecular formula C are identified using DEI-MS42H34N4O, detected value [M+1]+=611.52, Calculated value 610.27.
Embodiment 6
The synthesis of compound 48：
Take 9- ethyls -6,6,8- trimethyl -5H- benzos [b] carbazole -11 (6H) -one (3.03g, 10.0mmol), 2- (4- Bromophenyl) -4,6- bis- (naphthalene -2- bases) -1,3,5-triazines (5.36g, 11.0mmol), sodium tert-butoxide (4.93g, 50.0mmol) be molten In 100mL toluene, tetrakis triphenylphosphine palladium (1.16g, 1.0mmol) is added in nitrogen protection 0.5h, is warming up to 115 DEG C, heat preservation React 6h.It is cooled to room temperature after completion of the reaction, pours into 100g saturated sodium-chloride water solutions, is layered, saturated sodium-chloride is water-soluble Liquid washs organic phase, dry, and desolventizing obtains greenish yellow solid 8.21g.It is recrystallized using n-hexane, obtains off-white powder Grain (6.11g, yield 86%).The compound, molecular formula C are identified using DEI-MS50H38N4O, detected value [M+1]+= 711.52 calculated value 710.30.
According to the method prepare compound 1-51 described in embodiment 5, carry out detection compound using DEI-MS, then detection is each The detected value [M+1] that a compound obtains+And calculated value is as shown in Table 1 below.
Table 1
From the data of above-mentioned table 1 it is known that organic photoelectrical material shown in formula (1) has had successfully been obtained in the present invention.
The compounds of this invention is in luminescent device, as emitting layer material.To the compounds of this invention 1, compound 7, chemical combination Object 11, compound 16, compound 41, compound 48 carry out the test of hot property, and test result is as shown in table 2.
2 heat stability testing of table
Note：Glass transition temperature Tg is by differential scanning calorimetry (DSC, German Nai Chi companies DSC204F1 differential scanning calorimetries Instrument) it measures, 10 DEG C/min of heating rate；Thermal weight loss temperature Td is the temperature of the weightlessness 5% in nitrogen atmosphere, in Japanese Shimadzu public affairs It is measured on the TGA-50H thermogravimetric analyzers of department, nitrogen flow 20mL/min；Test is atmospheric environment.
By upper table data it is found that compound provided by the invention has higher thermal stability so that made contains The OLED device life-span upgrading of the compounds of this invention.
Organic electroluminescence device prepares embodiment (organic electroluminescence device hereinafter referred to as device)
In the embodiment for preparing organic electroluminescence device, used reagent material is as follows：
Anode：Tin indium oxide (abbreviation ITO) electro-conductive glass, hole-injecting material：Hat-CN, hole mobile material：NPB, Luminescent material：MCP, electron transport material：TPBI, electron injection material：LiF, wherein the structural formula of NPB, mCP and TPBI It mentions in the foregoing, details are not described herein.
Organic electroluminescence device is prepared in embodiment, and Japan is selected to open up general Kanggong department SR3 type spectroradiometers to upper It states the organic electroluminescence device that embodiment is prepared and carries out above-mentioned test, obtain opening in all organic electroluminescence devices Bright voltage, maximum current efficiency and spectral color, wherein above-mentioned all measure is carried out in atmosphere at room temperature.
The preparation of 1 device 1 of embodiment
Organic electroluminescence device is prepared by the following method：
Clean anode：ITO electro-conductive glass is cleaned with deionized water, acetone, EtOH Sonicate respectively, it is each super in above-mentioned solvent Sound cleans 30 minutes, is then handled 5 minutes in plasma cleaner；
The vacuum evaporation Hat-CN on anode obtains hole injection layer compound, and the thickness of hole injection layer is 50nm；
C) hole mobile material NPB is deposited by vacuum evaporation mode on hole injection layer, obtains hole transmission layer, it is thick Degree is 10nm；
D) on the hole transmission layer obtained in step c), vacuum evaporation includes being prepared in aforesaid compound preparation embodiment The luminescent material of obtained compound 1 and mCP obtains luminescent layer, and the thickness of luminescent layer is 30nm, wherein compound 1：MCP= 1:20(W/W)；
E) on the luminescent layer obtained in step d), vacuum evaporation electron transport material TPBI obtains electron transfer layer, electricity The thickness of sub- transport layer is 30nm；
F) on the electron transfer layer obtained in step e), vacuum evaporation electron injection material LiF obtains electron injection The thickness of layer, electron injecting layer is 1nm；
G) on the electron injecting layer obtained in step f), the thickness of vacuum evaporation cathode Al, cathode are 100nm, are obtained Organic electroluminescence device.
After electroluminescent device accomplished as described above, the driving voltage and current efficiency of measurement device, result is in table 3.
The preparation of 2 device 2 of embodiment
The present embodiment and device 1 the difference is that：The luminescent layer dopant material of the organic electroluminescence device of preparation Use compound 7 provided by the present invention.
The preparation of 3 device 3 of embodiment
The present embodiment and device 1 the difference is that：The luminescent layer dopant material of the organic electroluminescence device of preparation Use compound 11 provided by the present invention.
The preparation of 4 device 4 of embodiment
The present embodiment and device 1 the difference is that：The luminescent layer dopant material of the organic electroluminescence device of preparation Use compound 16 provided by the present invention.
The preparation of 5 device 5 of embodiment
The present embodiment and device 1 the difference is that：The luminescent layer dopant material of the organic electroluminescence device of preparation Use compound 41 provided by the present invention.
The preparation of 6 device 6 of embodiment
The present embodiment and device 1 the difference is that：The luminescent layer dopant material of the organic electroluminescence device of preparation Use compound 48 provided by the present invention.
The preparation of 1 device 1# of comparative example
Unlike device comparative example 1 and device 1：The luminescent layer of organic electroluminescence device is only using mCP as luminescent layer material Material is deposited.
Device 1-6 and device 1# are detected to obtain correlated results as shown in Table 3 below：
Table 3
By above-mentioned table 3 as a result, it is known that organic photoelectrical material provided by the present invention can be applied to organic electroluminescence hair In optical device so that organic electroluminescence device can obtain good performance.In addition, by by being prepared in embodiment The testing result of device can also learn that it is excellent that organic photoelectrical material provided by the invention so that organic electroluminescence device obtains Different performance, organic photoelectrical material provided by the present invention are used as the luminescent material of organic electroluminescence device so that device Part has larger maximum current efficiency, and device is made to open bright voltage with lower.
The foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, it is all the present invention spirit and Within principle, any modification, equivalent replacement, improvement and so on should all be included in the protection scope of the present invention.

Claims (6)

1. a kind of organic photoelectrical material, which is characterized in that including molecular structure shown in meeting formula (1)：
Wherein, at least one of N, S, O C are contained in R12-60One kind in aromatic heterocyclic base.
2. a kind of organic photoelectrical material according to claim 1, which is characterized in that the one kind of the R in following structures：
Wherein, * is the site being connect with parent.
3. a kind of application of organic photoelectrical material a kind of as described in any one of claims 1 or 2 in organic electroluminescence device.
4. a kind of organic electroluminescence device, which is characterized in that at least one layer of functional layer contains any one of claims 1 or 2 institute The organic photoelectrical material stated.
5. organic electroluminescence device according to claim 4, which is characterized in that including luminescent layer, the luminescent layer contains It has the right requirement 1 or 2 any one of them organic photoelectrical materials.
6. a kind of illumination or display element, which is characterized in that sent out including such as claim 4 or 5 any one of them organic electroluminescences Optical device.
CN201810186858.XA 2018-03-07 2018-03-07 A kind of organic photoelectrical material and its application Withdrawn CN108440385A (en)

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Application publication date: 20180824