CN107068887B - A kind of organic electroluminescence device and its application - Google Patents

A kind of organic electroluminescence device and its application Download PDF

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CN107068887B
CN107068887B CN201610259385.2A CN201610259385A CN107068887B CN 107068887 B CN107068887 B CN 107068887B CN 201610259385 A CN201610259385 A CN 201610259385A CN 107068887 B CN107068887 B CN 107068887B
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CN107068887A (en
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李崇
徐凯
张兆超
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Valiant Co Ltd
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

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Abstract

The invention discloses a kind of organic electroluminescence device and its applications, the device includes hole transmission layer, luminescent layer, electron transfer layer, the device emitting layer material includes the compound for containing 1,8 diaza, 9 Fluorenone group, shown in the structural formula of compound such as general formula (1).The present invention 1, 8 diaza, 9 Fluorenone class material is because have smaller triplet state and singlet energy difference, therefore it is easily achieved energy transmission between Subjective and Objective material, the energy to scatter and disappear in the form of heat originally is set to be easily obtained utilization, promote luminescent layer radiation transistion efficiency, to be easier to obtain the high efficiency of device, further, when 1, 8 diaza, 9 Fluorenone class compound-material is used directly as dopant material, or 1, 8 diaza, 9 fluorenes ketone compounds are as material of main part, when being selected as fluorescent material as dopant material, it is easier to obtain the luminous radiation of dopant material, to be easier to obtain the long-life of material.

Description

A kind of organic electroluminescence device and its application
Technical field
The present invention relates to technical field of semiconductors, are 1,8- diazas -9-Fluorenone more particularly, to a kind of emitting layer material The organic electroluminescence device of class compound and its application.
Background technology
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology both can be used for make New display product is made, can be used for making novel illumination product, be expected to substitute existing liquid crystal display and fluorescent lighting, Application prospect is very extensive.
OLED luminescent devices like the structure of sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it Between organic functional material, various different function materials are overlapped mutually according to purposes collectively constitutes OLED luminescent devices together. As current device, when the two end electrodes to OLED luminescent devices apply voltage, and pass through electric field action organic layer functional material Positive and negative charge in film layer, positive and negative charge is further compound in luminescent layer, that is, generates OLED electroluminescent.
Organic Light Emitting Diode (OLED) large-area flat-plate show and illumination in terms of application cause industrial quarters and The extensive concern of art circle.However, traditional organic fluorescence materials can only be shone using 25% singlet exciton to be formed is electrically excited, device The internal quantum efficiency of part is relatively low (up to 25%).External quantum efficiency is generally less than 5%, also has with the efficiency of phosphorescent devices very big Gap.Although phosphor material can efficiently use electricity since the strong SO coupling in heavy atom center enhances intersystem crossing The singlet exciton formed and Triplet exciton are excited, makes the internal quantum efficiency of device up to 100%.But phosphor material exists Expensive, stability of material is poor, and device efficiency tumbles the problems such as serious and limits its application in OLEDs.Hot activation is prolonged Slow fluorescence (TADF) material is the third generation luminous organic material developed after organic fluorescence materials and organic phosphorescent material.It should Class material generally has small poor (the △ E of singlet-tripletST), triplet excitons can be changed by anti-intersystem crossing It shines at singlet exciton.This can make full use of the singlet exciton and triplet excitons that are electrically excited lower formation, device it is interior Quantum efficiency can reach 100%.Meanwhile material structure is controllable, property is stablized, cheap to be not necessarily to precious metal, in OLED Field has a extensive future.
Although theoretically 100% exciton utilization rate may be implemented in TADF materials, following problem there are in fact:
(1) T1 the and S1 states of design molecule have strong CT features, very small S1-T1 states energy gap, although can pass through TADF processes realize high T1→S1State exciton conversion ratio, but low S1 state radiation transistion rates are also resulted in, consequently it is difficult to have both (or realizing simultaneously) high exciton utilization rate and high fluorescent radiation efficiency；
(2) even if doping device has been used to mitigate T exciton concentration quenching effects, the device of most of TADF materials is in height Efficiency roll-off is serious under current density.
For current OLED shows the actual demand of Lighting Industry, the development of OLED material is also far from enough at present, falls Afterwards in the requirement of panel manufacturing enterprise, the organic functional material as material enterprise development higher performance is particularly important.
Invention content
In view of the above-mentioned problems existing in the prior art, the present invention provides a kind of organic electroluminescence device and its applications. The present invention is based on the 1,8- of TADF mechanism diazas -9-Fluorenone class compounds as luminescent layer material of main part or dopant material application In on Organic Light Emitting Diode, there are good photoelectric properties, disclosure satisfy that OLED device enterprise, especially OLED display panel With the demand of OLED Illumination Enterprises.
Technical scheme is as follows：
A kind of organic electroluminescence device, the device include hole transmission layer, luminescent layer, electron transfer layer, device hair Photosphere material includes the compound for containing 1,8- diazas -9-Fluorenone group, shown in the structural formula of compound such as general formula (1)：
In general formula (1), Ar1、Ar2Respectively hydrogen,
In one kind；Ar1、Ar2It is asynchronously hydrogen；
Wherein, Ar indicates phenyl, xenyl, naphthalene or anthryl；R is hydrogen, C1-10Linear or branched alkyl group；X1For oxygen original Son, sulphur atom, selenium atom, C1-10The alkylidene of linear or branched alkyl group substitution, alkylidene, the alkyl or aryl of aryl substitution take One kind in the amido in generation；
Wherein, R1、R2Structure shown in selection hydrogen or general formula (2) independently；
A isX2、X3Respectively oxygen atom, sulphur atom, selenium atom, C1-10Linear or branched alkyl group One kind in the amido that alkylidene, the alkyl or aryl of substituted alkylidene, aryl substitution replace；A and CL1-CL2Key, CL2-CL3 Key, CL3-CL4Key, CL‘1-CL’2Key, CL‘2-CL’3Key or CL‘3-CL’4Key connection.
The general structure of the compound is：
Ar in the general formula (1)1、Ar2Respectively：
Any one of.
The concrete structure formula of the compound is：
The dopant material of material of main part of the material as luminescent layer shown in the general formula (1), luminescent layer is led to using following One kind in formula (9), (10) or (11) material：
In general formula (9), the separate one kind for being expressed as oxygen, carbon, nitrogen-atoms of Y1-Y6；
It is expressed as being connected to by arbitrary chemical bond containing the group there are two atom Ring；
Separate one kind for being expressed as oxygen, carbon, nitrogen-atoms of Y1-Y4 in general formula (10), general formula (11)；
It is expressed as passing through arbitrary chemical bond phase containing the group there are two atom It is linked to be ring.
The material of the hole transmission layer is the compound containing triarylamine group, the structural formula general formula of the compound As shown in general formula (12)：
D1-D3 respectively independently indicates substituted or unsubstituted C6-C30 aryl, 3 yuan substituted or unsubstituted in general formula (12) To 30 unit's heteroaryls；D1-D3 can be identical or different.
The material of the electron transfer layer is in material shown in general formula (13), (14), (15), (16) or (17) It is a kind of：
Wherein, E1-E10 is separately in general formula (13), general formula (14), general formula (15), general formula (16), general formula (17) Hydrogen, C1-30The alkyl or alkoxy, substituted or unsubstituted C of linear or branched alkyl group substitution6-30Aryl, substituted or unsubstituted 3 Member is to 30 unit's heteroaryls；It is hydrogen when E1-E10 differences.
The organic electroluminescence device further includes hole injection layer；The material of the hole injection layer is having structure One kind in general formula (18), (19), material shown in (20)：
In general formula (18), F1-F3 respectively independently indicates substituted or unsubstituted C6-30It is aryl, 3 yuan substituted or unsubstituted To 30 unit's heteroaryls；F1-F3 can be identical or different；
In general formula (19), general formula (20), the separate expression hydrogen of G1-G6, itrile group, halogen, amide groups, alkoxy, ester Base, nitro, C1-30Carbon atom, the substituted or unsubstituted C of linear or branched alkyl group substitution6-30Aryl, 3 yuan to 30 unit's heteroaryls； It is hydrogen when G1-G6 differences.
The organic electroluminescence device further includes electron injecting layer；The electron injecting layer material be lithium, lithium salts or One kind in cesium salt；The lithium salts is 8-hydroxyquinoline lithium, lithium fluoride, lithium carbonate, Lithium Azide；The cesium salt be cesium fluoride, Cesium carbonate, cesium azide.
The mass ratio of the dopant material of the luminescent layer and the material of main part of luminescent layer is 0.005~0.2:1.
The dopant material that compound shown in the general formula (1) is also used as luminescent layer uses.
A kind of application of the organic electroluminescence device, the organic electroluminescence device are used to prepare top-illuminating OLED Luminescent device.
A kind of application of the organic electroluminescence device, the organic electroluminescence device are shown applied to AM-OLED Device.
The present invention is beneficial to be had technical effect that：
Structure of the 1,8- diazas -9-Fluorenone class compound with TADF for forming OLED luminescent devices of the present invention is special Point, very small S1-T1 states energy gap easy to implement is poor, between excitation, the anti-system of triplet state easy to implement to singlet It alters more, makes to shine originally, dispersed heat is converted into the energy that can generate luminous energy in the form of heat, and is expected to obtain high Efficiency.
It is analyzed based on principles above, OLED luminescent devices of the present invention, can both select fluorescent material as doping material Material, can also select phosphor material as dopant material, can also be by TADF materials of the present invention directly as dopant material It uses.
Material of main part collocation iridium of 1, the 8- diazas -9-Fluorenone compound as OLED luminescent devices, platinum class phosphorescence When materials'use, the current efficiency of device, power efficiency and external quantum efficiency are greatly improved；Meanwhile for the device longevity Life is promoted clearly.Further, on OLED device layer structure matching, after introducing hole and electron injecting layer, make transparent Anode, metallic cathode and organic material contact interface are more stable, hole, electron injection effect promoting；Hole transmission layer can be folded again Layer is two or more layers, and the hole transmission layer of adjacent luminescent layer side can be named as electronic barrier layer (EBL), provide electronics again Barrier effect makes exciton combined efficiency in luminescent layer be promoted, and the hole transmission layer of adjacent hole injection layer side then plays hole Transmission and the effect for reducing exciton transfer barrier；Electron transfer layer again can lamination be two or more layers, adjacent luminescent layer side Electron transfer layer can be named as hole blocking layer (HBL) again, provide hole barrier effect, make exciton combined efficiency in luminescent layer It is promoted, the electron transfer layer of adjacent electron injecting layer side then plays the role of electron-transport and reduces exciton transfer barrier.So And, it is noted that each of these layers are not necessarily present.
The combined effect of OLED device compound of the present invention：So that the driving voltage of device reduces, current efficiency, work( Rate efficiency, external quantum efficiency are further enhanced, and device lifetime is promoted with obvious effects.Have in OLED luminescent devices good Application effect, have good industrialization prospect.
Make us against expectation, it has been found that, the compound combination being more particularly described hereinafter realizes this purpose, And lead to the improvement of organic electroluminescence device, especially voltage, efficiency and the improvement in service life.This especially suitable for red or The electroluminescent device of green phosphorescent, especially when using the device architecture and combination of materials of the present invention, situation is such.
Description of the drawings
Fig. 1 is the structural schematic diagram of stacked OLED device of the embodiment of the present invention；
In Fig. 1：1 be transparent substrates, 2 be ito anode layer, 3 be hole injection layer (HIL), 4 be hole transmission layer (HTL), 5 be electronic barrier layer (EBL), 6 be luminescent layer (EML), 7 be hole blocking layer (HBL), 8 be electron transfer layer (ETL), 9 be electricity Sub- implanted layer (EIL), 10 are cathode reflection electrode layer.
Fig. 2 is the structural formula of critical materials used in device embodiments of the present invention.
Specific implementation mode
With reference to the accompanying drawings and examples, the present invention is specifically described.
1 compound 1 of embodiment
The specific synthetic route of the compound is now provided：
0.01mol 3,6- dibromos 1,8- diaza -9- fluorenes is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml Ketone, 0.025mol 10H- phenoxazines, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-terts Phosphine, 150ml toluene are heated to reflux 24 hours, sample contact plate, the reaction was complete；Natural cooling, filtering, filtrate revolving cross silica gel Column obtains target product, purity 99.2%, yield 75.00%.
Elemental analysis structure (molecular formula C35H20N4O3)：Theoretical value C, 77.20；H,3.70；N,10.29；O,8.81；Test Value：C,77.29；H,3.80；N,10.20；O,8.71.
HPLC-MS：Material molecule amount is 544.15, surveys molecular weight 544.62.
2 compound 4 of embodiment
The preparation method is the same as that of Example 1 for compound 4, the difference is that using raw material 9,10- dihydro -9,9- dimethyl a word used for translations 10H- phenoxazines are replaced in pyridine.
3 compound 7 of embodiment
The specific synthetic route of the compound is now provided：
0.01mol 3,6- bis--(4- bromophenyls) -1,8- bis- is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml Azepine -9-Fluorenone, 0.025mol 5- phenyl -10- hydrogen azophenlyene, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphines, 150ml toluene are heated to reflux 24 hours, sample contact plate, the reaction was complete；Natural cooling filters, filter Liquid rotates, and crosses silicagel column, obtains target product, purity 99.5%, yield 72.00%.
Elemental analysis structure (molecular formula C59H38N6O)：Theoretical value C, 83.67；H,4.52；N,9.92；O,1.89；Test Value：C,83.73；H,4.39；N,9.90；O,1.98.
HPLC-MS：Material molecule amount is 846.31, surveys molecular weight 846.40.
4 compound 8 of embodiment
0.01mol 3,6- bis--(3- bromophenyls) -1,8- bis- is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml Azepine -9-Fluorenone, 0.025mol 9,10- dihydro -9,9- dimethyl acridiniums, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2 (dba)3, 1 × 10-4Mol tri-tert-butylphosphines, 150ml toluene are heated to reflux 24 hours, sample contact plate, the reaction was complete；Naturally cold But, it filters, filtrate revolving crosses silicagel column, obtains target product, purity 96.0%, yield 52.00%.
Elemental analysis structure (molecular formula C53H40N4O)：Theoretical value C, 85.00；H,5.38；N,7.48；O,2.14；Test Value：C,85.15；H,5.31；N,7.50；O,2.04.
HPLC-MS：Material molecule amount is 748.32, surveys molecular weight 748.50.
5 compound 12 of embodiment
0.01mol 3, bis- bromo- 1,8- diazas -9- fluorenes of 6- is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml Ketone, 0.025mol raw material As, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphines, 150ml toluene is heated to reflux 24 hours, samples contact plate, the reaction was complete；Natural cooling, filtering, filtrate revolving are crossed silicagel column, are obtained To target product, purity 98.23%, yield 60.00%.
Elemental analysis structure (molecular formula C59H48N4O)：Theoretical value C, 85.48；H,5.84；N,6.76；O,1.93；Test Value：C,85.35；H,5.81；N,6.80；O,2.04.
HPLC-MS：Material molecule amount is 828.38, surveys molecular weight 828.79.
6 compound 15 of embodiment
Bromo- 1, the 8- diazas -9-Fluorenones of 0.01mol 2- are added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml, 0.025mol 5,5- dimethyl -5,8a, 12a, 13- tetrahydrochysene -8- oxa-s -13- azepines-indoles [1,2-a] anthracene, the tertiary fourths of 0.03mol Sodium alkoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphines, 150ml toluene are heated to reflux 24 hours, sample point Plate, the reaction was complete；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity 99.8%, yield 51.00%.
Elemental analysis structure (molecular formula C32H23N3O2)：Theoretical value C, 79.81；H,4.81；N,8.73；O,6.65；Test Value：C,79.88；H,4.86；N,8.80；O,6.46.
HPLC-MS：Material molecule amount is 481.18, surveys molecular weight 481.88.
7 compound 17 of embodiment
0.01mol 3, the 6- bis--(bromo- biphenyl -4- of 4'- is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml Base) -1,8- diazas -9-Fluorenone, 0.025mol 10H- phenoxazines, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2 (dba)3, 1 × 10-4Mol tri-tert-butylphosphines, 150ml toluene are heated to reflux 24 hours, sample contact plate, the reaction was complete；Naturally cold But, it filters, filtrate revolving crosses silicagel column, obtains target product, purity 97.5%, yield 75.90%.
Elemental analysis structure (molecular formula C59H36N4O3)：Theoretical value C, 83.47；H,4.27；N,6.60；O,5.65；Test Value：C,83.29；H,4.40；N,6.65；O,5.66.
HPLC-MS：Material molecule amount is 848.28, surveys molecular weight 849.11.
8 compound 19 of embodiment
0.01mol 3,6- dibromos 1,8- diaza -9- fluorenes is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml Ketone, 0.025mol 6,6- dimethyl -6,11- dihydro -13- oxa-s -11- azepines-indoles [1,2-b] anthracene, the 0.03mol tert-butyl alcohols Sodium, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine 150ml toluene, is heated to reflux 24 hours, samples contact plate, The reaction was complete；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity 95.0%, yield 62.00%.
Elemental analysis structure (molecular formula C53H36N4O3)：Theoretical value C, 81.94；H,4.67；N,7.21；O,6.18；Test Value：C,81.90；H,4.68；N,7.30；O,6.12.
HPLC-MS：Material molecule amount is 776.28, surveys molecular weight 777.06.
9 compound 24 of embodiment
0.01mol 3,6- bis- (3- bromophenyls) 1,8- phenodiazines is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml Miscellaneous -9-Fluorenone, 6,6,13,13- tetramethyl -11,13- dihydro 6H-11- azepines of 0.025mol-indoles [1,2-b] anthracene, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphines, 150ml toluene, are heated to reflux 24 Hour, contact plate is sampled, the reaction was complete；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity 96.0%, yield 71.00%.
Elemental analysis structure (molecular formula C71H56N4O)：Theoretical value C, 86.91；H,5.75；N,5.71；O,1.63；Test Value：C,86.90；H,5.78；N,5.60；O,1.72.
HPLC-MS：Material molecule amount is 980.45, surveys molecular weight 980.66.
10 compound 37 of embodiment
The preparation method of compound 37 is with embodiment 3, the difference is that using raw material 11,11- dimethyl -4a, and 6,11, 13a- tetrahydrochysene -13- oxa-s -6- azepines-indoles [1,2-b] anthracene replaces 5- phenyl -10- hydrogen azophenlyene.
11 compound 58 of embodiment
The preparation method of compound 58 is with embodiment 8, the difference is that using raw material 14,14- dimethyl -7,14- bis- Hydrogen -5,12- dioxas -7- azepines-pentacene replacement 6,6- dimethyl -6,11- dihydro -13- oxa-s -11- azepines-indoles [1, 2-b] anthracene.
12 compound 59 of embodiment
The preparation method of compound 59 is with embodiment 8, the difference is that raw material 14H-5,7,12- trioxa -14- nitrogen Miscellaneous-pentacene replaces 6,6- dimethyl -6,11- dihydro -13- oxa-s -11- azepines-indoles [1,2-b] anthracene.
13 compound 61 of embodiment
The preparation method of compound 61 is with embodiment 8, the difference is that using 7,7,12,12- tetramethyl -7 of raw material, 14- dihydro -12H-5- oxa-s -14- azepines-pentacene replaces 6,6- dimethyl -6,11- dihydro -13- oxa- -11- azepines-Yin Diindyl [1,2-b] anthracene.
14 compound 62 of embodiment
The preparation method of compound 62 is with embodiment 8, the difference is that using raw material 5- phenyl -12- phenyl -5H-5, [2,3-b] phenoxazines replace 6,6- dimethyl -6,11- dihydro -13- oxa-s -11- to tri- azepines of 7,12--benzo [b, f] azepines Azepine-indoles [1,2-b] anthracene.
15 compound 65 of embodiment
The preparation method of compound 65 is with embodiment 8, the difference is that using raw material 6,14- dihydros 12, and 14- dioxies Miscellaneous -7- azepines-benzo [a, d] cycloheptene [1,2-b] anthracene replaces 6,6- dimethyl -6,11- dihydro -13- oxa- -11- azepines-Yin Diindyl [1,2-b] anthracene.
16 compound 74 of embodiment
0.01mol 3,6- bis--(4- bromophenyls) -1,8- bis- is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 500ml Azepine -9-Fluorenone, 0.02mol 2- boric acid 5,11- dimethyl-indols [3,2,1-jk] carbazole dissolve (180ml with mixed solvent Toluene, 90ml ethyl alcohol), 0.03mol Na are then added2CO30.0001mol Pd (PPh are then added in aqueous solution (2M)3)4, add Heat reflux 10 hours, samples contact plate, the reaction was complete；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, Purity 99.52%, yield 63.7%.
Elemental analysis structure (molecular formula C63H40N4O)：Theoretical value C, 87.07；H,4.64；N,6.45；O,1.84；Test Value：C,87.10；H,4.66；N,6.40；O,1.84.
HPLC-MS：Material molecule amount is 868.32, surveys molecular weight 868.69.
17 compound 78 of embodiment
The preparation method is the same as that of Example 16 for compound 78, the difference is that using raw material 3,6- dibromos 1,8- diazas- 9-Fluorenone replaces 3,6- bis--(4- bromophenyls) -1,8- diazas -9-Fluorenone, using raw material 2- boric acid indoles [3,2,1-jk] click Azoles 5- phenyl -10- hydrogen azophenlyene replaces 2- boric acid 5,11- dimethyl-indols [3,2,1-jk] carbazole.
The compounds of this invention can be used as emitting layer material, to the compounds of this invention 37, compound 74, current material CBP carries out the test of hot property, luminescent spectrum, HOMO, lumo energy respectively, and test result is as shown in table 1.
Table 1
Note：Thermal weight loss temperature Td is the temperature of the weightlessness 1% in nitrogen atmosphere, in the TGA-50H heat of Japanese Shimadzu Corporation It is measured on weight analysis instrument, nitrogen flow 20mL/min；λPLIt is sample solution fluorescence emission wavelengths, Pu Kang is opened up using Japan SR-3 spectroradiometers measure；Φ f are that solid powder fluorescence quantum efficiency (utilizes the Maya2000Pro of U.S.'s marine optics Fiber spectrometer, the test solid fluorescence amount of C-701 integrating spheres and marine optics LLS-LED the light sources composition of Lan Fei companies of the U.S. Sub- efficiency test system, reference literature Adv.Mater.1997,9,230-232 method are measured)；Highest occupied molecular rail Road HOMO energy levels and minimum occupied molecular orbital lumo energy are by photoelectron emissions spectrometer (AC-2 type PESA), UV, visible light point Light photometric determination is tested as atmospheric environment.
By upper table data it is found that the compounds of this invention has suitable HOMO, lumo energy and higher thermal stability, It is suitable as the material of main part of luminescent layer；Meanwhile the compounds of this invention has suitable luminescent spectrum, higher Φ f so that answer The compounds of this invention is used to get a promotion as the OLED device efficiency of dopant material and service life.
Below by way of device embodiments 1-16 and device comparative example 1, the present invention will be described in detail that compound combination is answered in the devices Use effect.The making work of device embodiments 2-16 of the present invention, the device compared with device embodiments 1 of device comparative example 1 Skill is identical, and uses identical baseplate material and electrode material, the difference is that device is surveyed stepped construction, taken It is different with material and thicknesses of layers.Each device embodiments laminated construction is as shown in table 2.The performance test results of obtained device As shown in table 3.
Device embodiments 1
Device stack structure is as shown in device architecture schematic diagram 1：
2 (thickness of ito anode layer：150nm)/4 (thickness of hole transmission layer：190nm, material：HT6)/6 (thickness of luminescent layer： 40nm, material：Compound 1 and RD1 are by weight 95：5 blendings are constituted) 8 (thickness of/electron transfer layer：35nm, material：ET2 and EI1, mass ratio 1:1)/Al (thickness：100nm).
Specific preparation process is as follows：
Ito anode layer 2 (film thickness 150nm) is washed, is carried out after progress neutralizing treatment, pure water, drying successively ultraviolet Line-ozone washing is to remove the organic residue on the transparent surfaces ITO.
On ito anode layer 2 after the washing, using vacuum deposition apparatus, hole transmission layer, hole transmission layer is deposited Materials'use HT6, film thickness 190nm, this layer is as the hole transmission layer 4 in device architecture.
On hole transmission layer 4, by vacuum evaporation mode, luminescent layer 6 is deposited, emitting layer material is made using compound 1 Based on material, for RD1 as dopant material, doping mass ratio is 95：5, luminescent layer film thickness is 40nm, this layer is as device junction Luminescent layer 6 in structure
On luminescent layer 6, by vacuum evaporation mode, be deposited electron transfer layer, electron transport layer materials using ET2 and EI1 mixing and dopings, doping mass ratio are 1:1, film thickness 35nm, this layer is as the electron transfer layer 8 in device architecture
On electron transfer layer 8, by vacuum evaporation mode, evaporation cathode aluminium (Al) layer, film thickness 100nm, this layer is Cathode reflection electrode layer 10 uses.
After completing the making of OLED luminescent devices as described above, anode and cathode is connected with well known driving circuit Come, the luminous efficiency of measurement device, the I-E characteristic of luminescent spectrum and device.
Device embodiments 2
Device stack structure is as shown in device architecture schematic diagram 1：
2 (thickness of ito anode layer：150nm)/3 (thickness of hole injection layer：10nm, material：HI1)/hole transmission layer 4 is (thick Degree：180nm, material：HT2)/6 (thickness of luminescent layer：40nm, material：Compound 4 and RD2 are by weight 96：4 blendings are constituted)/ 8 (thickness of electron transfer layer：35nm, material：ET02 and EI1, mass ratio 1:1)/Al (thickness：100nm).
Device embodiments 3
Device stack structure is as shown in device architecture schematic diagram 1：
2 (thickness of ito anode layer：150nm)/3 (thickness of hole injection layer：10nm, material：HI2)/hole transmission layer 4 is (thick Degree：180nm, material：HT4)/6 (thickness of luminescent layer：40nm, material：Compound 7 and RD2 are by weight 96：4 blendings are constituted)/ 8 (thickness of electron transfer layer：35nm, material：ET3 and EI1, mass ratio 1:1)/9 (thickness of electron injecting layer：1nm, material： LiN3)/Al (thickness：100nm).
Device embodiments 4
Device stack structure is as shown in device architecture schematic diagram 1：
2 (thickness of ito anode layer：150nm)/3 (thickness of hole injection layer：10nm, material：HI1)/hole transmission layer 4 is (thick Degree：160nm, material：HT3)/5 (thickness of electronic barrier layer：20nm, material：EB2)/6 (thickness of luminescent layer：40nm, material：Change Object 8 and RD3 are closed by weight 96：4 blendings are constituted) 8 (thickness of/electron transfer layer：35nm, material：ET3 and EI1, mass ratio 1: 1)/Al (thickness：100nm).
Device embodiments 5
Device stack structure is as shown in device architecture schematic diagram 1：
2 (thickness of ito anode layer：150nm)/3 (thickness of hole injection layer：50nm, material：HI3 and HT3, in mass ratio 5: 95 blendings are constituted) 4 (thickness of/hole transmission layer：140nm, material：HT3)/6 (thickness of luminescent layer：40nm, material：Compound 15 With RD3 by weight 96：4 blendings are constituted) 8 (thickness of/electron transfer layer：35nm, material：ET3)/9 (thickness of electron injecting layer： 1nm, material：Li)/Al (thickness：100nm).
Device embodiments 6
Device stack structure is as shown in device architecture schematic diagram 1：
2 (thickness of ito anode layer：150nm)/3 (thickness of hole injection layer：50nm, material：HI4 and HT3, in mass ratio 5: 95 blendings are constituted) 4 (thickness of/hole transmission layer：140nm, material：HT6)/6 (thickness of luminescent layer：40nm, material：Compound 17 With RD4 by weight 96：4 blendings are constituted) 8 (thickness of/electron transfer layer：35nm, material：ET4 and EI1, mass ratio 1:1)/electricity 9 (thickness of sub- implanted layer：1nm, material：LiF)/Al (thickness：100nm).
Device embodiments 7
Device stack structure is as shown in device architecture schematic diagram 1：
2 (thickness of ito anode layer：150nm)/3 (thickness of hole injection layer：10nm, material：HI1)/hole transmission layer 4 is (thick Degree：160nm, material：HT6)/5 (thickness of electronic barrier layer：20nm, material：EB1)/6 (thickness of luminescent layer：40nm, material：Change Object 19 and RD4 are closed by weight 96：4 blendings are constituted) 7 (thickness of/hole blocking layer：20nm, material：HB1)/electron transfer layer 8 (thickness：15nm, material：ET2 and EI1, mass ratio 1:1)/Al (thickness：100nm).
Device embodiments 8
Device stack structure is as shown in device architecture schematic diagram 1：
2 (thickness of ito anode layer：150nm)/3 (thickness of hole injection layer：50nm, material：HI5 and HT3, in mass ratio 5: 95 blendings are constituted) 4 (thickness of/hole transmission layer：120nm, material：HT5)/5 (thickness of electronic barrier layer：20nm, material：EB3)/ 6 (thickness of luminescent layer：40nm, material：Compound 37 and RD5 are by weight 96：4 blendings are constituted) 8 (thickness of/electron transfer layer： 35nm, material：ET2 and EI1, mass ratio 1：1)/9 (thickness of electron injecting layer：1nm, material：Cs2CO3)/Al (thickness： 100nm)。
Device embodiments 9
Device stack structure is as shown in device architecture schematic diagram 1：
2 (thickness of ito anode layer：150nm)/3 (thickness of hole injection layer：50nm, material：HI6 and HT4, in mass ratio 5: 95 blendings are constituted) 4 (thickness of/hole transmission layer：120nm, material：HT6)/5 (thickness of electronic barrier layer：20nm, material：EB2)/ 6 (thickness of luminescent layer：40nm, material：Compound 58 and RD6 are by weight 96：4 blendings are constituted) 8 (thickness of/electron transfer layer： 35nm, material：ET2 and EI1, mass ratio 1：1)/9 (thickness of electron injecting layer：1nm, material：EI1)/Al (thickness：100nm).
Device embodiments 10
Device stack structure is as shown in device architecture schematic diagram 1：
2 (thickness of ito anode layer：150nm)/3 (thickness of hole injection layer：10nm, material：HI1)/hole transmission layer 4 is (thick Degree：50nm, material：HT3)/5 (thickness of electronic barrier layer：140nm, material：EB1)/6 (thickness of luminescent layer：40nm, material：Change Object 59 and RD5 are closed by weight 96：4 blendings are constituted) 7 (thickness of/hole blocking layer：25nm, material：HB1)/electron transfer layer 8 (thickness：10nm, material：ET5)/9 (thickness of electron injecting layer：1nm, material：EI1)/Al (thickness：100nm).
Device embodiments 11
Device stack structure is as shown in device architecture schematic diagram 1：
2 (thickness of ito anode layer：150nm)/3 (thickness of hole injection layer：50nm, material：HI5 and HT6, in mass ratio 5: 95 blendings are constituted) 4 (thickness of/hole transmission layer：120nm, material：HT6)/5 (thickness of electronic barrier layer：20nm, material：EB2)/ 6 (thickness of luminescent layer：40nm, material：Compound 61 and RD4 are by weight 96：4 blendings are constituted) 7 (thickness of/hole blocking layer： 15nm, material：HB1)/8 (thickness of electron transfer layer：20nm, material：ET2 and EI1, mass ratio 1：1)/electron injecting layer 9 is (thick Degree：1nm, material：Li2CO3)/Al (thickness：100nm).
Device embodiments 12
Device stack structure is as shown in device architecture schematic diagram 1：
2 (thickness of ito anode layer：150nm)/3 (thickness of hole injection layer：50nm, material：HI5 and HT3, in mass ratio 5: 95 blendings are constituted) 4 (thickness of/hole transmission layer：140nm, material：HT6)/6 (thickness of luminescent layer：40nm, material：Compound 65 With RD6 by weight 96：4 blendings are constituted) 7 (thickness of/hole blocking layer：15nm, material：HB1)/8 (thickness of electron transfer layer： 20nm, material：ET6)/9 (thickness of electron injecting layer：1nm, material：CsF)/Al (thickness：100nm).
Device embodiments 13
Device stack structure is as shown in device architecture schematic diagram 1：
2 (thickness of ito anode layer：150nm)/3 (thickness of hole injection layer：50nm, material：HI5 and HT3, in mass ratio 5: 95 blendings are constituted) 4 (thickness of/hole transmission layer：120nm, material：HT6)/5 (thickness of electronic barrier layer：20nm, material：EB2)/ 6 (thickness of luminescent layer：40nm, material：Compound 74 and RD2 are by weight 96：4 blendings are constituted) 8 (thickness of/electron transfer layer： 35nm, material：ET2 and EI1, mass ratio 1：1)/9 (thickness of electron injecting layer：1nm, material：CsN3)/Al (thickness：100nm).
Device embodiments 14
Device stack structure is as shown in device architecture schematic diagram 1：
2 (thickness of ito anode layer：150nm)/3 (thickness of hole injection layer：50nm, material：HI5 and HT3, in mass ratio 5: 95 blendings are constituted) 4 (thickness of/hole transmission layer：120nm, material：HT6)/5 (thickness of electronic barrier layer：20nm, material：EB2)/ 6 (thickness of luminescent layer：40nm, material：Compound 78, RH2 and RD2 are by weight 78：18：4 blendings are constituted)/hole blocking layer 7 (thickness 15nm, material：EB2)/8 (thickness of electron transfer layer：20nm, material：ET2 and EI1, mass ratio 1：1)/Al (thickness： 100nm)。
Device embodiments 15
Device stack structure is as shown in device architecture schematic diagram 1：
2 (thickness of ito anode layer：150nm)/3 (thickness of hole injection layer：50nm, material：HI4 and HT3, in mass ratio 5: 95 blendings are constituted) 4 (thickness of/hole transmission layer：140nm, material：HT6)/6 (thickness of luminescent layer：40nm, material：RH1 and chemical combination Object 19 is by weight 96：4 blendings are constituted) 8 (thickness of/electron transfer layer：35nm, material：ET4 and EI1, mass ratio 1:1)/electronics 9 (thickness of implanted layer：1nm, material：LiF)/Al (thickness：100nm).
Device embodiments 16
Device stack structure is as shown in device architecture schematic diagram 1：
2 (thickness of ito anode layer：150nm)/3 (thickness of hole injection layer：50nm, material：HI5 and HT3, in mass ratio 5: 95 blendings are constituted) 4 (thickness of/hole transmission layer：140nm, material：HT6)/6 (thickness of luminescent layer：40nm, material：RH2 and chemical combination Object 78 is by weight 96：4 blendings are constituted) 7 (thickness of/hole blocking layer：15nm, material：HB1)/8 (thickness of electron transfer layer： 20nm, material：ET6)/9 (thickness of electron injecting layer：1nm, material：CsF)/Al (thickness：100nm).
Device comparative example 1
Device stack structure is as shown in device architecture schematic diagram 1：
2 (thickness of ito anode layer：150nm)/4 (thickness of hole transmission layer：190nm, material：HTI)/6 (thickness of luminescent layer： 40nm, material：RH1 and RD1 is by weight 90：10 blendings are constituted) 8 (thickness of/electron transfer layer：35nm, material：ET1)/electronics 9 (thickness of implanted layer：1nm, material：LiF)/Al (thickness：100nm).
The OLED is characterized by standard method, from current/voltage/luminous density characteristic line that Lambert emission characteristic is presented It calculates, and measures the service life.It determines in 1000cd/m2Electroluminescent spectrum under brightness calculates CIEx and y color coordinates, device Test data is as shown in table 3.
Table 2
Table 3
Note：For device detection performance using comparative example 1 as reference, 1 device property indices of comparative example are set as 1.0.Compare The current efficiency of example 1 is 11.2cd/A (@1000cd/m2)；Driving voltage is 5.4v (@1000cd/m2)；LT95 under 3000 brightness Life time decay is 8Hr.
Table 3 summarizes the OLED device in 1000cd/m2Voltage needed for brightness, the current efficiency reached, Yi Ji 3000cd/m2LT95 Decays under brightness.
1 comparative device comparative example 1 of device embodiments replaces the luminescent layer material of main part of the present invention, and by the material of the present invention After material is combined into laminated device, device voltage reduces, and current efficiency promotes 50%, 2 times of life-span upgrading；Device embodiments 2-16 is pressed Material adapted and the device stack combination that the present invention designs so that device data is further promoted；As shown in device embodiments 14, When 1,8- diazas -9-Fluorenone class material of the present invention is as hybrid agent material, extraordinary performance is further obtained Data；As shown in device embodiments 15,16,1,8- of present invention diazas -9-Fluorenone class material makes as luminescent layer dopant material Used time equally obtains extraordinary performance data.
To sum up, the foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention With within principle, any modification, equivalent replacement, improvement and so on should all be included in the protection scope of the present invention god.

Claims (13)

1. a kind of organic electroluminescence device, which includes hole transmission layer, luminescent layer, electron transfer layer, it is characterised in that The device emitting layer material includes the compound for containing 1,8- diazas -9-Fluorenone group, the structural formula of compound such as general formula (1) shown in：
In general formula (1), Ar1、Ar2Respectively hydrogen,
In one kind；Ar1、Ar2It is asynchronously hydrogen；
Wherein, Ar indicates phenyl, xenyl, naphthalene or anthryl；R is hydrogen, C1-10Linear or branched alkyl group in one kind；X1For Oxygen atom, sulphur atom, selenium atom, C1-10The alkylidene of linear or branched alkyl group substitution, alkylidene, alkyl or the virtue of aryl substitution One kind in the amido of base substitution；
Wherein, R1、R2Structure shown in selection hydrogen or general formula (2) independently：
A isIn one kind, X2、X3Respectively oxygen atom, sulphur atom, selenium atom, C1-10Linear chain or branched chain One kind in the amido that alkyl-substituted alkylidene, the alkylidene of aryl substitution, alkyl or aryl replace；A and CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL‘1-CL’2Key, CL‘2-CL’3Key or CL‘3-CL’4Key connection.
2. organic electroluminescence device according to claim 1, it is characterised in that the general structure of the compound is：
3. organic electroluminescence device according to claim 1, it is characterised in that Ar in the general formula (1)1、Ar2Respectively For:
Any one of.
4. organic electroluminescence device according to claim 1, it is characterised in that the concrete structure of the compound is：
Any one of.
5. organic electroluminescence device according to claim 1, it is characterised in that material conduct shown in the general formula (1) The dopant material of the material of main part of luminescent layer, luminescent layer uses one kind in material shown in general formula (9), (10) or (11)：
In general formula (9), the separate one kind for being expressed as oxygen, carbon, nitrogen-atoms of Y1-Y6； Point It is not expressed as containing there are two the groups of atom to pass through the connected cyclization of arbitrary chemical bond；
Separate one kind for being expressed as oxygen, carbon, nitrogen-atoms of Y1-Y4 in general formula (10), general formula (11)；
The group for being expressed as the atom containing there are two is connected by arbitrary chemical bond Cyclization.
6. organic electroluminescence device according to claim 1, it is characterised in that the material of the hole transmission layer be containing There is the compound of triarylamine group, shown in the structural formula general formula such as general formula (12) of the compound：
D1-D3 respectively independently indicates substituted or unsubstituted C6-C30 aryl, 3 yuan to 30 substituted or unsubstituted in general formula (12) One kind in unit's heteroaryl；D1-D3 can be identical or different.
7. organic electroluminescence device according to claim 1, it is characterised in that under the material of the electron transfer layer is One kind in material shown in row general formula (13), (14), (15), (16) or (17)：
Wherein, in general formula (13), general formula (14), general formula (15), general formula (16), general formula (17) E1-E10 separately be hydrogen, C1-30The alkyl or alkoxy, substituted or unsubstituted C of linear or branched alkyl group substitution6-30It is aryl, 3 yuan substituted or unsubstituted One kind into 30 unit's heteroaryls；It is hydrogen when E1-E10 differences.
8. organic electroluminescence device according to claim 1, it is characterised in that the device further includes hole injection layer； The material of the hole injection layer is one kind in having structure general formula (18), (19), material shown in (20)：
In general formula (18), F1-F3 respectively independently indicates substituted or unsubstituted C6-30It is aryl, 3 yuan to 30 yuan substituted or unsubstituted One kind in heteroaryl；F1-F3 can be identical or different；
In general formula (19), general formula (20), the separate expression hydrogen of G1-G6, itrile group, halogen, amide groups, alkoxy, ester group, nitre Base, C1-30Carbon atom, the substituted or unsubstituted C of linear or branched alkyl group substitution6-30Aryl, one in 3 yuan to 30 unit's heteroaryls Kind；It is hydrogen when G1-G6 differences.
9. organic electroluminescence device according to claim 1, it is characterised in that the device further includes electron injecting layer；Institute It is one kind in lithium, lithium salts or cesium salt to state electron injecting layer material；The lithium salts be 8-hydroxyquinoline lithium, lithium fluoride, lithium carbonate, Lithium Azide；The cesium salt is one kind in cesium fluoride, cesium carbonate, cesium azide.
10. according to organic electroluminescence device described in claim 1, it is characterised in that the dopant material of the luminescent layer with shine The mass ratio of the material of main part of layer is 0.005~0.2:1.
11. organic electroluminescence device according to claim 1, it is characterised in that compound shown in the general formula (1) is also It can be used as the dopant material of luminescent layer.
12. a kind of application of any one of claim 1~11 organic electroluminescence device, it is characterised in that the Organic Electricity Electroluminescence device is used to prepare top-illuminating OLED luminescent device.
13. a kind of application of any one of claim 1~11 organic electroluminescence device, it is characterised in that the Organic Electricity Electroluminescence device is applied to AM-OLED displays.
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