CN108727394A - A kind of bipolarity main body electroluminescent organic material and its application - Google Patents

A kind of bipolarity main body electroluminescent organic material and its application Download PDF

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CN108727394A
CN108727394A CN201810310130.3A CN201810310130A CN108727394A CN 108727394 A CN108727394 A CN 108727394A CN 201810310130 A CN201810310130 A CN 201810310130A CN 108727394 A CN108727394 A CN 108727394A
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main body
layer
organic
bipolarity
electroluminescent
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李庆
任大永
林存生
孟凡民
周银波
胡葆华
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Valiant Co Ltd
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Abstract

The purpose of the present invention is to provide a kind of bipolarity main body electroluminescent organic materials, it is mainly used in field of organic electroluminescent materials, compared with prior art, the advantages that bipolarity main body electroluminescent organic material thermodynamic stability is good, good film-forming property, suitable triplet of the present invention, can be used as blue and green light material of main part.

Description

A kind of bipolarity main body electroluminescent organic material and its application
Technical field
The invention belongs to field of organic electroluminescent materials, more particularly to a kind of bipolarity main body organic electroluminescence material Material and its application.
Background technology
Phosphor material can take full advantage of account for 75% ratio three that electron-hole recombinations generate in electroluminescent device Line state exciton, intersystem crossing occurs for singlet exciton can make to the transfer of the triplet state of more low-lying level
The exciton utilization rate of phosphorescent devices even can reach 100%.Phosphor material is entrained in usually as guest materials In material of main part, effective material of main part should have ideal band gap to make energy be efficiently transferred to object, good current-carrying Sub- transport property in emission layer to realize the balance recombination of carrier, and the level-density parameter with adjacent layer is to realize effective electricity Lotus is injected, and enough heat and morphology stability to be to extend device lifetime, therefore the exploitation of material of main part is for efficient Electroluminescent phosphorescence shines of crucial importance.
Traditional material of main part usually only has single carrier transport property, this unbalanced carrier transport property Have shown that the cut-in voltage to OLED and the unfavorable property in service life.Develop new material of main part requirement must have it is bipolar Carrier (hole and electronics) injects and transport property, adds up between luminescent layer and charge transport layer to avoid carrier, draws Interface Exciplex emission is played, causes the major parameters such as the external quantum efficiency, power efficiency, current efficiency of device relatively low, Open phenomena such as bright voltage is higher, and spectrum is unstable.Therefore, in recent years can equilbrium carrier transmission bipolar material of main part cause Sizable concern.
Invention content
It is an object of the invention to be directed to the problems of prior art, a kind of bipolarity main body organic electroluminescence hair is provided Luminescent material, bipolarity main body electroluminescent organic material thermodynamic stability of the present invention is good, good film-forming property, triplet state energy The advantages that grade is suitable, can be used as blue and green light material of main part.
In order to achieve the above object, the present invention provides a kind of bipolarity main body organic electroluminescence material, the bipolaritys Main body electroluminescent organic material has structure shown in formula (1),
Wherein, Ar1And Ar2It is independently selected from acyclic straight or branch containing substituent group either unsubstituted C1-C10 Alkyl, C6-C30 containing substituent group either unsubstituted aryl, C3-C30 containing substituent group or it is unsubstituted contain miscellaneous original Sub- aryl；
R1-R6 is independent selected from hydrogen atom, D-atom, the acyclic straight of C1-C10 or branched alkyl, C1-C10 Acyclic straight either branched alkoxy or R1-R6Two neighboring group is mutually bonded and forms saturated or unsaturated ring knot Structure, such as form anthracene, phenanthrene, benzanthracene structure etc..
Further, the R1-R6It is identical or different, the R1-R6It is preferential independent selected from hydrogen atom, D-atom, first Base, ethyl, propyl, isopropyl, butyl, tertiary butyl, amyl, hexyl, methoxyl group, ethyoxyl, propoxyl group, butoxy, amoxy, Any one of hexyloxy or the two neighboring groups of R1-R6 are mutually bonded and form saturated or unsaturated ring structure, such as Form anthracene, phenanthrene, benzanthracene structure etc..
Further, the Ar1、Ar2It is preferential independent selected from any one of following group：
The beneficial effects of adopting the above-mentioned further technical scheme are as follows：R1And R2It is independent to be selected from above-mentioned group, be conducive to be promoted The thermal stability and carrier transport efficiency of material.
Further, any one of the structural formula of compound in the structural formula in C1-C50：
Compound C01-C50 is the representative structure or preferred structure for meeting spirit of that invention and principle, it should be understood that row Go out above compound structure, is intended merely to preferably explain the present invention, is not limitation of the present invention.
The beneficial effects of adopting the above-mentioned further technical scheme are as follows：Above-mentioned compound C01-C50, by experimental verification, Have many advantages, such as thermodynamic stability well and good moulding property.
The present invention also provides a kind of preparation methods of above-mentioned bipolarity main body electroluminescent organic material, including following step Suddenly：
In a nitrogen environment, it is 1 by molar ratio：0.8-1.2：2.0-4.0：0.5-1.0：The M classes intermediate of 0.5-1.0, Ar containing halides1- X, potassium carbonate, copper powder, 6 ether of 18- crown-s are added in the solution of o-dichlorohenzene；The insulation reaction that flows back 24 hours, Cooling filters, and crosses column and removes mechanical admixture, desolventizing purifies to obtain N class intermediates through column chromatography for separation；
Further, in a nitrogen environment, it is 1 by molar ratio：0.8-1.2：The N classes intermediate of 2.0-4.0 contains halides Ar2- X, potassium tert-butoxide are added to containing catalyst Pd (OAc)2, ligand tri-tert-butylphosphine tetrafluoroborate o-xylene solution In；The insulation reaction that flows back 24 hours cools down, and filters, and crosses column and removes mechanical admixture, desolventizing purifies to obtain mesh through column chromatography for separation Object is marked, reaction equation is as follows：
Wherein, X Cl, Br, I；
Ar1、Ar2It is independent selected from containing substituent group either the acyclic straight of unsubstituted C1-C10 or branched alkyl, C6-C30 containing substituent group either unsubstituted aryl, C3-C30 containing substituent group or it is unsubstituted containing hetero atom virtue Base；The Ar1、Ar2Preferentially it is independently selected from any one of following group：
The beneficial effects of adopting the above-mentioned further technical scheme are as follows：Inventor is found surprisingly that under study for action, R1And R2It is independent Be selected from above-mentioned group, be conducive to promoted material thermal stability and carrier transport efficiency.
R1-R6The independent fat selected from hydrogen atom, D-atom, the acyclic straight of C1-C10 or branched alkyl, C1-C10 Fat race straight chain either branched alkoxy or R1-R6Two neighboring group is mutually bonded and forms saturated or unsaturated ring knot Structure, such as form anthracene, phenanthrene, benzophenanthrene structure.
Take having the beneficial effect that for above-mentioned technical proposal：By strictly controlling the reaction condition of each step, ensure each Reaction be smoothed out and the purity of obtained product.
Further, the M classes intermediate or N class intermediates, as R therein1-R6When group at position is H, in M classes Mesosome can be used to prepare bipolarity main body electroluminescent organic material directly as intermediate M；
The preparation method of intermediate M includes the following steps：
1. preparing intermediate M-1
In a nitrogen environment, it is 1 by molar ratio：2.0-2.4：The bis- bromo- 4,5- dinitrobenzenes of 1,2- of 4.0-6.0, adjacent chlorine Aniline, potassium tert-butoxide are added to containing catalyst acetic acid palladium, in the o-xylene solution of tri-tert-butylphosphine tetrafluoroborate, nitrogen Back flow reaction 12-16 hours under gas shielded, cooling down filters, and washing organic phase to neutrality is dry, desolventizing, through column chromatography Separating-purifying obtains intermediate M-1；
2. preparing intermediate M-2
In a nitrogen environment, it is 1.0 by molar ratio:4.0-6.0:Intermediate M-1, potassium carbonate, the Pd of 0.2-0.4 (OAc)2, it is added in DMF solution；The insulation reaction that flows back 20-24 hours, cooling, reaction solution is poured into water, and a large amount of palm fibres are precipitated Yellow solid filters, purifies to obtain intermediate M-2 through column chromatography for separation；
3. preparing intermediate M-3
In autoclave, intermediate M-2 is added in 100~1000mL autoclaves, with 0.1~0.2g/1g intermediates M-2 Ratio Pd/C (5%) is added, tetrahydrofuran is added with the ratio of 50~100mL/1g intermediates M-2；Nitrogen replace three times, into One step hydrogen is replaced three times, and system hydrogen environment is kept.Keep 60-70 DEG C of temperature, pressure 1.0-1.5MPa, reaction 10-15 small When, cool down, filter, remove Pd/C, crosses column and remove mechanical admixture, further desolventizing purifies to obtain intermediate through column chromatography for separation M-3；
4. preparing intermediate M
In a nitrogen environment, it is 1 by molar ratio：0.8-1.0：Intermediate M-3, acenaphthenequinone, the p-methyl benzenesulfonic acid of 0.01-0.1, It is added in toluene solution, assembles water knockout drum.Reflux water-dividing reacts 24 hours under nitrogen protection, cooling down, filters, 100- 200mL toluene solutions elute filter cake, and washing filtrate organic phase to neutrality is dry, and desolventizing is purified through column chromatography for separation in obtaining Mesosome M.
The present invention also provides application of the above-mentioned bipolarity main body electroluminescent organic material in field of organic electroluminescence. The bipolarity main body electroluminescent organic material can be used as material of main part, especially as Blue-light emitting host material or green light main body Material.
Such as：It is used for field of organic electroluminescence using above-mentioned material as green light material of main part, in particular for Organic Electricity The luminescent layer of electroluminescence device.During specific application, the implementation process with as a result, being intended merely to preferably explain The present invention is not limitation of the present invention.
The present invention provides a kind of organic electroluminescence device, including：
Anode, cathode and the organic luminescence function layer between the anode and the cathode, wherein described organic Light emitting functional layer includes above-mentioned bipolarity main body electroluminescent organic material.
If organic light emitting functional layer is equipped with multiple, at least one organic luminescence function layer contains above-mentioned bipolarity master Body electroluminescent organic material.
Using having the beneficial effect that for above-mentioned technical proposal：Due to bipolarity main body electroluminescent organic material of the present invention With the injection of higher carrier and transmittability, therefore the dipole characteristic with good transporting holes and electronics uses this The organic electroluminescence device of kind of material preparation has many advantages, such as to open that bright voltage is low, luminous efficiency is high；Bipolarity of the present invention Main body electroluminescent organic material has larger molecular weight, has higher glass transition temperature and heat decomposition temperature, chemical combination The stability of object is high, is conducive to the service life for significantly improving device；Bipolarity main body electroluminescent organic material tool of the present invention There are higher singlet and triplet, it is preferable that can be used as the use of green light material of main part.Using bipolarity of the present invention Main body electroluminescent organic material can effectively promote external quantum efficiency, power efficiency as material of main part, the device of preparation And current efficiency.
Further, the organic luminescence function layer includes luminescent layer, and the luminescent layer includes that material of main part and object shine Material, the material of main part include the bipolarity main body electroluminescent organic material.
Further, the organic luminescence function layer includes hole injection layer, hole transmission layer, electron transfer layer, electronics note Enter any one in layer, hole blocking layer, electronic barrier layer or arbitrary several combination.
By taking green light OLED device as an example, the ITO Conducting Glass (anode) being sequentially overlapped, hole injection layer are generally comprised (HATCN), hole transmission layer (NPB), luminescent layer (electroluminescent organic material of the present invention), electron transfer layer (TPBI), electron injecting layer (LiF) and cathode layer (Al), as shown in Figure 1.All functional layers are all made of vacuum evaporation process system At.The molecular structural formula of some used organic compounds is as follows in such device.
In the present invention, the functional layer of device is not limited to use above-mentioned material, these materials that can be replaced with other materials, Can be replaced with TAPC to device performance to be further improved, such as hole transmission layer, electron transfer layer can use TpPyPB, The molecular structural formula of the replacements such as TmPyPB, these materials is as follows：
Compared with prior art, bipolarity main body electroluminescent organic material of the present invention has the following advantages：
1. bipolarity main body electroluminescent organic material of the present invention has the injection of higher carrier and transmittability, Dipole characteristic with good transporting holes and electronics.
2. bipolarity main body electroluminescent organic material of the present invention has larger molecular weight, have compared with high-vitrification The advantages that transition temperature and heat decomposition temperature, the stability of compound is high.
3. bipolarity main body electroluminescent organic material of the present invention has higher singlet and triplet, into One step can be used as the use of green light material of main part.Using the organic compound of the present invention as material of main part, the device of preparation can It is effective to promote external quantum efficiency, power efficiency and current efficiency.
Description of the drawings
Fig. 1 is that the structural schematic diagram of organic electroluminescence device prepared by the present invention is followed successively by by lower layer to upper layer：
101, ITO Conducting Glass, 102, hole injection layer, 103, hole transmission layer, 104, luminescent layer, 105, electronics Transport layer, 106, electron injecting layer, 107, cathode layer, wherein luminescent layer 104, which is related to bipolarity main body of the present invention, to be had Electroluminescent material.
Specific implementation mode
The principle and features of the present invention will be described below with reference to the accompanying drawings, and the given examples are served only to explain the present invention, and It is non-to be used to limit the scope of the present invention.
Embodiment 1：The preparation of compound C10
(1) successively into 100ml there-necked flasks be added intermediate M (2.16g, 0.005mol), iodobenzene (1.02g, 0.005mol), potassium carbonate (2.76g, 0.02mol), copper powder (256mg, 0.004mol), 6 ether of 18- crown-s (1.6g, 0.004mol), 20mL o-dichlorobenzene solutions.25 DEG C are stirred 10min, are flowed back under nitrogen protection and are stirred to react 24.0hrs, TLC prisons Survey raw material is cooled to 25 DEG C after the reaction was complete.It filters and removes most of mechanical admixture and salinity, it is anhydrous that 100mL is added into filtrate Ethyl alcohol, sub-cooled cooling crystallization, filters again.Filter cake uses 200-500mL tetrahydrofuran thermosols, direct too short silicagel column to remove Whole mechanical admixtures are removed, column liquid desolventizing is crossed and obtains brown yellow powder solid.Column chromatography purification & isolation obtains 1.07g yellow powders Shape solid intermediate N, yield 42.0%.Tetrahydrofuran/absolute ethyl alcohol recrystallization further can be used.
(2) intermediate N (2.54g, 0.005mol), 2- (4- bromophenyls) -4,6- bis- is added into 250ml there-necked flasks successively Phenyl -1,3,5-triazines (1.94g, 0.005mol), ortho-xylene (100mL), catalyst Pd (OAc)2(112mg, 0.0005mol), tri-tert-butylphosphine tetrafluoroborate (290mg, 0.001mol), potassium tert-butoxide (1.92g, 0.02mol).25℃ 10min is stirred, bath temperature is set as 145-150 DEG C, flows back under nitrogen protection and be stirred to react 24.0hrs, and TLC monitoring raw materials have reacted It is cooled to 25 DEG C after complete.It filters and removes most of mechanical admixture and salinity, filtrate is washed to neutrality, and anhydrous sodium sulfate drying is organic Phase, organic phase desolventizing obtain brown color and consolidate object.Room temperature will be down to after filter cake thermosol using tetrahydrofuran, direct column chromatography removes Whole mechanical admixtures cross column liquid desolventizing and obtain brown yellow powder solid.Column chromatography purification & isolation obtains 1.14g yellow powders Solid, yield 27.9%.Tetrahydrofuran/absolute ethyl alcohol recrystallization further can be used.
Embodiment 2：The preparation of compound C40
Intermediate N (2.54g, 0.005mol), 2- (4- bromophenyls) -1- phenyl-is added into 250ml there-necked flasks successively 1H- benzos [d] imidazoles (1.75g, 0.005mol), ortho-xylene (100mL), catalyst Pd (OAc)2(112mg, 0.0005mol), tri-tert-butylphosphine tetrafluoroborate (290mg, 0.001mol), potassium tert-butoxide (1.92g, 0.02mol).25℃ 10min is stirred, bath temperature is set as 145-150 DEG C, flows back under nitrogen protection and be stirred to react 24.0hrs, and TLC monitoring raw materials have reacted It is cooled to 25 DEG C after complete.It filters and removes most of mechanical admixture and salinity, filtrate is washed to neutrality, and anhydrous sodium sulfate drying is organic Phase, organic phase desolventizing obtain brown color and consolidate object.Room temperature will be down to after filter cake thermosol using tetrahydrofuran, direct column chromatography removes Whole mechanical admixtures cross column liquid desolventizing and obtain brown yellow powder solid.Column chromatography purification & isolation obtains 1.32g yellow powders Solid, yield 34.0%.Tetrahydrofuran/absolute ethyl alcohol recrystallization further can be used.
The present invention chooses compound C10, C40 making organic electroluminescence device and should be appreciated that device implementation process and knot Fruit is intended merely to preferably explain the present invention, not limitation of the present invention.
Embodiment 3：Applications of the compound C10 in organic electroluminescence device
The present embodiment prepares organic electroluminescence device one by the following method：
A) ITO (tin indium oxide) glass is cleaned：Respectively each 30 points of ito glass is cleaned with deionized water, acetone, EtOH Sonicate Then clock is handled 5 minutes in plasma cleaner；
B) the vacuum evaporation hole injection layer HATCN on anode ito glass, thickness 10nm；
C) the vacuum evaporation hole transmission layer NPB on hole transmission layer, thickness 30nm；
D) on hole transmission layer NPB, the compound C10 of the preparation of vacuum evaporation luminescent layer embodiment 1:7%wt Ir (ppy)3, thickness 30nm；
E) on luminescent layer, TPBI, thickness 30nm of the vacuum mixing vapor deposition as electron transfer layer；
F) on electron transfer layer, vacuum evaporation electron injecting layer LiF, thickness 1nm；
G) on electron injecting layer, vacuum evaporation cathode Al, thickness 100nm.
The structure of device is ITO/HATCN (10nm)/NPB (30nm)/compound C10:7%wt Ir (ppy)3(30nm)/ TPBI (30nm)/LiF (1nm)/Al (100nm), during vacuum evaporation, pressure<4.0×10-4Pa, using compound C10 as The test result of the material of main part of device one, obtained device is shown in Table 1.
Embodiment 4：Applications of the compound C40 in organic electroluminescence device
Organic electroluminescence device two is made successively according to method same as Example 3, and difference lies in use C40 conducts The main body of luminescent layer replaces synthesis compound C10 in the embodiment 1 as the layer main body that shines.The test result of obtained device is shown in Table Shown in 1.
Comparative example 1：Organic electroluminescence device is made according to method same as Example 3, difference lies in use 4,4'- What two (9H- carbazoles) -1,1'- biphenyl (CBP) replaced synthesizing in the embodiment 1 as luminous layer main body as the main body of luminescent layer C10.The test result of obtained device is shown in Table 1.
1 device photoelectric tables of data of table
In order to compare, present invention manufacture uses the parametric device of conventional body material C BP.As shown in table 1, based on CBP's Device, the height with 4.8V open bright voltage, maximum power efficiency 12.8lm/W, maximum current efficiency 17.1cd/A；Based on this hair Organic electroluminescence device prepared by bright material of main part, illustrates preferable performance, and compound C10 devices open bright voltage 4.2V, Maximum current efficiency 23.2cd/A, maximum power efficiency 15.0lm/W；Compound C40 devices open bright voltage 4.2V, maximum current Efficiency 24.2cd/A, maximum power efficiency 16.8lm/W.Compared with conventional body material C BP, device of the invention is in efficiency, drive Outstanding characteristic is shown in terms of dynamic voltage and stability.Particularly, the higher characteristics of luminescence, and this are shown in terms of efficiency Invention material of main part has significant dipole characteristic.
Example the above is only the implementation of the present invention is not limitation of the present invention.The present invention provides a kind of bipolar Property main body electroluminescent organic material, with the electroluminescent device that material provided by the present invention makes, device performance has into one The space promoted is walked, other materials is such as used to replace NPB as hole transmission layer, replaces TPBI as electronics using other materials Transport layer makes luminescent layer etc. using the mode of other doping, similar to improve all it should be understood that belonging to the protection of the present invention Scope.
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 (7)

1. a kind of bipolarity main body electroluminescent organic material, it is characterised in that：With structure shown in formula (1),
Wherein, Ar1、Ar2Be independently selected from containing substituent group either the acyclic straight of unsubstituted C1-C10 or branched alkyl, C6-C30 containing substituent group either unsubstituted aryl, C3-C30 containing substituent group or it is unsubstituted containing hetero atom virtue Base；
R1-R6The independent aliphatic selected from hydrogen atom, D-atom, the acyclic straight of C1-C10 or branched alkyl, C1-C10 Either branched alkoxy or the two neighboring groups of R1-R6 are mutually bonded and form saturated or unsaturated ring structure straight chain.
2. bipolarity main body electroluminescent organic material according to claim 1, it is characterised in that：The Ar1、Ar2It is independent Selected from any one of following group：
3. bipolarity main body electroluminescent organic material according to claim 1 or 2, it is characterised in that：The compound Any one of structural formula in the structural formula in C1-C50：
4. the bipolarity main body electroluminescent organic material described in a kind of any one of claim 1-3 is led in organic electroluminescent Application in domain.
5. a kind of organic electroluminescence device, which is characterized in that including:
Anode, cathode and the organic luminescence function layer between the anode and the cathode, wherein the organic light emission Functional layer includes the bipolarity main body electroluminescent organic material described in any one of claims 1 to 3.
6. organic electroluminescence device according to claim 5, it is characterised in that：The organic luminescence function layer includes hair Photosphere, the luminescent layer include material of main part and guest emitting material, and the material of main part, which includes the bipolarity main body, to be had Electroluminescent material.
7. organic electroluminescence device according to claim 6, it is characterised in that：The organic luminescence function layer further includes Any one in hole injection layer, hole transmission layer, electron transfer layer, electron injecting layer, hole blocking layer, electronic barrier layer Or a variety of combination.
CN201810310130.3A 2018-04-08 2018-04-08 A kind of bipolarity main body electroluminescent organic material and its application Withdrawn CN108727394A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022069453A1 (en) * 2020-10-02 2022-04-07 Cynora Gmbh Organic molecules for optoelectronic devices

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022069453A1 (en) * 2020-10-02 2022-04-07 Cynora Gmbh Organic molecules for optoelectronic devices

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