CN107068911A - A kind of organic electroluminescence device containing anthracene ketone compounds and its application - Google Patents
A kind of organic electroluminescence device containing anthracene ketone compounds and its application Download PDFInfo
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- CN107068911A CN107068911A CN201610260617.6A CN201610260617A CN107068911A CN 107068911 A CN107068911 A CN 107068911A CN 201610260617 A CN201610260617 A CN 201610260617A CN 107068911 A CN107068911 A CN 107068911A
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- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H—ELECTRICITY
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
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- 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
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- 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 containing anthracene ketone compounds, the device includes hole transmission layer, luminescent layer, electron transfer layer, the device emitting layer material includes the compound containing anthrone group, shown in the structural formula such as formula (1) of the compound.Anthrone class material of the present invention is because with less triplet state and singlet energy difference, therefore it is easily achieved energy transmission between Subjective and Objective material, the energy scattered and disappeared in the form of heat originally is set to be easily obtained utilization, lift luminescent layer radiation transistion efficiency, so as to be easier to the high efficiency for obtaining device, further, when dopant material selection is fluorescent material, it is easier to obtain the luminous radiation of dopant material, so as to be easier to obtain the long-life of material.
Description
Technical field
It is the organic of anthracene ketone compounds more particularly, to a kind of emitting layer material the present invention relates to technical field of semiconductors
Electroluminescent device and its application.
Background technology
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology both can for system
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 quite varied.
OLED luminescent devices just as the structure of sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it
Between organic functional material, various difference in functionality 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 combined in luminescent layer, that is, produces 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 lighted 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 enhances intersystem crossing due to the strong SO coupling in heavy atom center, electricity can be effectively utilized
The singlet exciton to be formed and Triplet exciton are excited, makes the internal quantum efficiency of device up to 100%.But phosphor material is present
Expensive, stability of material is poor, and the problems such as device efficiency tumbles serious 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.Should
Class material typically has small poor (the △ E of singlet-tripletST), triplet excitons can be changed by anti-intersystem crossing
It is luminous into 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, and property is stable, cheap without precious metal, in OLED
Field has a extensive future.
Although TADF materials can realize 100% exciton utilization rate in theory, following problem there are in fact:
(1) T1 the and S1 states of design molecule have strong CT features, very small S1-T1 state energy gaps, although can pass through
TADF processes realize high T1→S1State exciton conversion ratio, but low S1 state radiation transistion speed is also resulted in, consequently it is difficult to have concurrently
(or realizing simultaneously) high exciton utilization rate and high fluorescent radiation efficiency；
(2) even if mitigating T exciton concentration quenching effects using doping device, the device of most of TADF materials is in height
Efficiency roll-off is serious under current density.
For the actual demand that current OLED shows Lighting Industry, the development of current OLED material is also far from enough, falls
After the requirement of panel manufacturing enterprise, it is particularly important as the organic functional material of material enterprise development higher performance.
The content of the invention
In view of the above-mentioned problems existing in the prior art, the invention provides a kind of organic electroluminescence containing anthracene ketone compounds
Luminescent device.Anthracene ketone compounds of the invention based on TADF mechanism are applied to Organic Light Emitting Diode as emitting layer material
On, with good photoelectric properties, it disclosure satisfy that OLED enterprise, particularly OLED display panel and OLED Illumination Enterprises
Demand.
Technical scheme is as follows：
A kind of organic electroluminescence device containing anthracene ketone compounds, the device includes hole transmission layer, luminescent layer, electricity
Sub- transport layer, the device emitting layer material includes the compound containing anthrone group, the structural formula such as formula (1) of the compound
It is shown：
In formula (1), D1、D2Selection C independently1-10Straight or branched alkyl, phenyl, xenyl, terphenyl,
Naphthyl or anthryl, D1、D2Can be with identical or different；N takes 1 or 2；
Described-(R)nExpression is connected on any carbon atom on the phenyl ring of formula (1) both sides；
In formula (1), R is represented using formula (2) or formula (3)：
Wherein, Ar represents C6-30Aromatic radical, furyl, thienyl, pyrrole radicals, quinolyl or isoquinolyl；X1It is former for oxygen
Son, sulphur atom, selenium atom, C1-10Alkylidene, alkylidene, the alkyl or aryl of aryl substitution of straight or branched alkyl substitution take
One kind in the amido in generation；
Wherein, R1、R2Structure shown in selection hydrogen or formula (4) independently：
A isX2、X3It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Straight or branched
One kind in alkyl-substituted alkylidene, the alkylidene of aryl substitution, the amido of alkyl or aryl substitution；A and CL1-CL2Key,
CL2-CL3Key, CL3-CL4Key, CL4-CL5Key, CL‘1-CL’2Key, CL‘2-CL’3Key, CL‘3-CL’4Key or CL‘4-CL’5Key is connected.
When a is represented in the compoundAnd and CL4-CL5Key or CL‘4-CL’5When key is connected, X1And X2Position weight
It is folded, only take X1Or X2；X3It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Alkylidene, the virtue of straight or branched alkyl substitution
One kind in the amido that alkylidene, the alkyl or aryl of base substitution replace；A passes through CL4-CL5Key or CL‘4-CL’5Key is connected to logical
On the middle phenyl ring of formula (2) or formula (3).
The general structure of the compound is：
R is in the formula (1)：
Any of.The concrete structure formula of the compound is：
Material shown in the formula (1) as luminescent layer material of main part；Under the dopant material use of the luminescent layer
One kind in material shown in row formula (13), (14), (15) or (16)：
In formula (13), B1-B10 selections are hydrogen, C1-30Straight or branched alkyl substitution alkyl or alkoxy, substitution or
Unsubstituted C6-30Aryl, substituted or unsubstituted 3 yuan to 30 unit's heteroaryls；It is hydrogen when B1-B10 is different；
In formula (14), the one kind for being expressed as oxygen, carbon, nitrogen-atoms of Y1-Y6 independently； It is expressed as the group containing two atoms and is connected cyclic by any chemical bond；
Respective independent one kind for being expressed as oxygen, carbon, nitrogen-atoms of Y1-Y4 in formula (15), formula (16)；It is expressed as the group containing two atoms and is connected cyclic by any chemical bond.
The material of the hole transmission layer is the compound containing triarylamine group, the structure such as formula of the compound
(17) shown in：
D1-D3 each independently represents substituted or unsubstituted C in formula (17)6-30Aryl, substituted or unsubstituted 3 yuan extremely
30 unit's heteroaryls；D1-D3 can be with identical or difference.
The material of the electron transfer layer is one in material shown in general formula (18), (19), (20), (21) or (22)
Kind：
E1-E10 selections are hydrogen, C in formula (18), formula (19), formula (20), formula (21), formula (22)1-30Straight chain
Or the alkyl or alkoxy, substituted or unsubstituted C of branched alkyl substitution6-30Aryl, substituted or unsubstituted 3 yuan to 30 yuan it is miscellaneous
Aryl；It is hydrogen when E1-E10 is different.
Described organic electroluminescence device also includes hole injection layer；The hole injection layer material is logical for having structure
One kind in formula (23), (24), material shown in (25)：
In formula (23), F1-F3 each independently represents substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 3 yuan
To 30 unit's heteroaryls；F1-F3 can be with identical or difference；
In formula (24), formula (25), G1-G6 each independent expression hydrogen, itrile group, halogen, amide groups, alkoxy, ester
Base, nitro, C1-30Carbon atom, the substituted or unsubstituted C of straight or branched alkyl substitution6-30Aryl, 3 yuan to 30 unit's heteroaryls,
It is hydrogen when G1-G6 is different.
Described organic electroluminescence device, in addition to electron injecting layer；The electron injecting layer material is 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 is fluorination
Caesium, 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.
Compound shown in the formula (1) can also be used as the dopant material of luminescent layer.
A kind of application of the organic electroluminescence device, for preparing top-illuminating OLED luminescent device.
A kind of application of the organic electroluminescence device, applied to AM-OLED displays.
The present invention is beneficial to be had technical effect that：
Constituting the anthracene ketone compounds of OLED luminescent devices of the present invention has TADF design feature, easily realizes non-
Often small S1-T1 state energy gaps are poor, in the case of exciting, easily realize triplet state to the anti-intersystem crossing of singlet, make originally not
Can be luminous, dispersed heat, which is converted into, in the form of heat can produce the energy of luminous energy, and be expected to obtain high efficiency.
Based on principles above analysis, 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
Use.
The anthracene ketone compounds are as the material of main part collocation iridium of OLED luminescent devices, and platinum class phosphor material or anthracene class are glimmering
Luminescent material is in use, the current efficiency of device, power efficiency and external quantum efficiency are greatly improved；Simultaneously for device
Life-span upgrading is clearly.Further, in the collocation of OLED Rotating fields, introduce after hole and electron injecting layer, make
Bright anode, metallic cathode and organic material contact interface are more stable, hole, electron injection effect promoting；Hole transmission layer again may be used
Lamination is two layers or multilayer, and the hole transmission layer of adjacent luminescent layer side can be named as electronic barrier layer (EBL) again, and there is provided electricity
Sub- barrier effect, lifts exciton combined efficiency in luminescent layer, and the hole transmission layer of adjacent hole injection layer side then plays sky
Transmit and reduce the effect of exciton transfer barrier in cave；Electron transfer layer again can lamination be two layers or multilayer, adjacent luminescent layer side
Electron transfer layer can be named as hole blocking layer (HBL) again there is provided hole barrier effect, make in luminescent layer the compound effect of exciton
Rate is lifted, and the electron transfer layer of adjacent electron injecting layer side then plays a part of electric transmission and reduction exciton transfer barrier.
It should be mentioned, however, that each in these layers is not necessarily present.
The combined effect of OLED compound of the present invention：So that the driving voltage reduction of device, current efficiency, work(
Rate efficiency, external quantum efficiency are further enhanced, and device lifetime lifting effect is obvious.Have in OLED luminescent devices good
Application effect, with good industrialization prospect.
Make us against expectation, it has been found that, the compound combination being more particularly described hereinafter realizes this mesh
, and cause the improvement in the improvement of organic electroluminescence device, particularly voltage, efficiency and life-span.This is particularly suitable for use in red
The electroluminescent device of color or green phosphorescent, especially in the device architecture and combination of materials using the present invention, situation is such.
Brief description of the drawings
Fig. 1 is the structural representation 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 negative electrode reflection electrode layer.
Fig. 2 is the structural formula of critical materials used in device embodiments of the present invention.
Embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
The compound 1 of embodiment 1
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol 3- (4- bromophenyls) -10,10- diformazans
Base -10H- anthrones, 0.03mol 9,9- dimethyl acridiniums, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10- 4Mol tri-butyl phosphines, 150ml toluene is heated to reflux 24 hours, sample point plate, and reaction is complete；Natural cooling, filtering, filtrate
Revolving, crosses silicagel column, obtains target product, purity 95.2%, yield 77.00%.
HPLC-MS：Material molecule amount is 505.24, surveys molecular weight 505.29.
The compound 2 of embodiment 2
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol 3- (3- bromophenyls) -10,10- diformazans
Base -10H- anthrones, 0.03mol phenoxazines, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4The tertiary fourths of mol tri-
Base phosphine, 150ml toluene is heated to reflux 24 hours, sample point plate, and reaction is complete；Natural cooling, filtering, filtrate revolving crosses silica gel
Post, obtains target product, purity 99.20%, yield 73.50%.
HPLC-MS：Material molecule amount is 479.19, surveys molecular weight 479.46.
The compound 4 of embodiment 3
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, addition 0.01mol 3, bromo- 10, the 10- diphenyl of 6- bis--
10H- anthrones, 0.03mol 5- phenyl azophenlyene, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4The uncles of mol tri-
Butyl phosphine, 150ml toluene is heated to reflux 24 hours, sample point plate, and reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicon
Glue post, obtains target product, purity 99.1%, yield 73.60%.
HPLC-MS：Material molecule amount is 858.34, surveys molecular weight 858.52.
The compound 5 of embodiment 4
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds bromo- 10, the 10- dimethyl -10H- anthracenes of 0.01mol 2-
Ketone, 0.03mol 9,9- diphenylacridines, 0.03mol sodium tert-butoxides, 01 × 10-4mol Pd2(dba)3, 1 × 10-4The uncles of mol tri-
Butyl phosphine, 150ml toluene is heated to reflux 24 hours, sample point plate, and reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicon
Glue post, obtains target product, purity 99.325%, yield 63.56%.
HPLC-MS：Material molecule amount is 553.24, surveys molecular weight 553.53.
The compound 7 of embodiment 5
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol 3- (4- bromophenyls) -10,10- diformazans
Base -10H- anthrones, 0.03mol acridine spiral shell anthrones, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-
Tert-butyl group phosphine, 150ml toluene is heated to reflux 24 hours, sample point plate, and reaction is complete；Natural cooling, filtering, filtrate revolving, mistake
Silicagel column, obtains target product, purity 98.50%, yield 63.25%.
HPLC-MS：Material molecule amount is 655.25, surveys molecular weight 655.66.
The compound 8 of embodiment 6
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol2- (4- bromophenyls) -10,10- diformazans
Base -10H- anthrones, 0.03mol 6,6- dimethyl -6,11- dihydro -13- oxa-s -11- azepines-indoles and anthracene, the tertiary fourths of 0.03mol
Sodium alkoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene is heated to reflux 24 hours, sample point
Plate, reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 99.33%, yield
72.50%.
HPLC-MS：Material molecule amount is 595.25, surveys molecular weight 595.32.
The compound 9 of embodiment 7
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, addition 0.01mol3, bromo- 10, the 10- dimethyl of 6- bis--
10H- anthrones, 0.03mol 6,6- dimethyl -6,11- dihydro -13- oxa-s -11- azepines-indoles and anthracene, the 0.03mol tert-butyl alcohols
Sodium, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene is heated to reflux 24 hours, sample point plate,
Reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 99..20%, yield
68.20%.
HPLC-MS：Material molecule amount is 816.34, surveys molecular weight 816.56.
The compound 15 of embodiment 8
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol1- (3- bromophenyls) -10,10- diformazans
Base -10H- anthrones, 0.03mol11,11- dimethyl -5- phenyl -11,13- dihydro -5H- indoles [1,2-b] azophenlyene, 0.03mol
Sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene is heated to reflux 24 hours, taken
Sampling point plate, reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 99.55%, yield
63.50%.
HPLC-MS：Material molecule amount is 670.30, surveys molecular weight 670.61.
The compound 17 of embodiment 9
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol2,7- bis- (4- bromophenyls) -10,10- bis-
Methyl isophthalic acid 0H- anthrones, 0.03mol 11,11- dimethyl -6,11- dihydro -13- oxa-s -6- azepines-indoles [1,2-b] anthracene,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24
Hour, sample point plate, reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity
98.62%, yield 72.3%.
HPLC-MS：Material molecule amount is 968.40, surveys molecular weight 968.94.
The compound 19 of embodiment 10
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol2- (5- bromine furans -2- bases) -10,10-
Dimethyl -10H- anthrones, 0.03mol 6H-11- oxa- -13- thias -6- azepines-indoles [1,2-b] anthracene, the 0.03mol tert-butyl alcohols
Sodium, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene is heated to reflux 24 hours, sample point plate,
Reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 99.20%, yield 62.3%.
HPLC-MS：Material molecule amount is 575.16, surveys molecular weight 575.33.
The compound 20 of embodiment 11
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol3- (the bromo- 1- methyl isophthalic acids H- pyrroles -2- of 5-
Base) -10,10- dimethyl -10H- anthrones, 0.03mol 13,13- dimethyl -6,13- dihydro -11- oxa-s -6- azepines-indoles
[1,2-b] anthracene, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene,
It is heated to reflux 24 hours, sample point plate, reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target production
Thing, purity 99.6%, yield 68.00%.
HPLC-MS：Material molecule amount is 598.26, surveys molecular weight 598.35.
The compound 21 of embodiment 12
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol3- (8- bromoquinoline -5- bases) -10,10-
Dimethyl -10H- anthrones, 0.03mol 11,11- dimethyl -13- phenyl -11,13- dihydro -5H- indoles [1,2-b] azophenlyene,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24
Hour, sample point plate, reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity
99.8%, yield 63.51%.
HPLC-MS：Material molecule amount is 721.31, surveys molecular weight 721.36.
The compound 23 of embodiment 13
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol3- (4- bromophenyls) -10,10- hexichol
Base -10H- anthrones, 0.03mol 13,13- dimethyl -5,13- dihydro -8- oxa-s -5- azepines-indoles [1,2-a] anthracene,
0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24
Hour, sample point plate, reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity
99.8%, yield 63.51%.
HPLC-MS：Material molecule amount is 719.28, surveys molecular weight 719.38.
The compound 31 of embodiment 14
The preparation method be the same as Example 1 of compound 31, difference is raw material 5,5- diphenyl -5,8a, 12a, 13- tetra-
Hydrogen -8- oxa-s -13- azepines-indoles [1,2-a] anthracene replaces acridine and anthrone.
The compound 35 of embodiment 15
The preparation method be the same as Example 1 of compound 35, difference is raw material 14,14- dimethyl -5,14- dihydro-naphthalene
And [2,3-b] acridine replaces 9,9- dimethyl acridiniums.
The compound 38 of embodiment 16
The preparation method be the same as Example 13 of compound 38, difference is raw material 14,14- dimethyl -7,14- dihydro -
5,12- dioxas -7- azepines-pentacene replaces 13,13- dimethyl -5,13- dihydro -8- oxa-s -5- azepines-indoles [1,2-a]
Anthracene.
The compound 40 of embodiment 17
The preparation method be the same as Example 7 of compound 40, difference is raw material 14,14- dimethyl -7,14- dihydro -5,
12- dioxas -7- azepines-pentacene replaces 6,6- dimethyl -6,11- dihydro -13- oxa-s -11- azepines-indoles and anthracene.
The compound 41 of embodiment 18
The preparation method be the same as Example 13 of compound 38, difference is that raw material A replaces 13,13- dimethyl -5,13-
Dihydro -8- oxa-s -5- azepines-indoles [1,2-a] anthracene.
The compound 45 of embodiment 19
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, addition 0.01mol3, bromo- 10, the 10- dimethyl of 6- bis--
10H- anthrones, 0.03mol 9H-5- oxa-s -9,13b- diaza-naphthalene [3,2,1-de] anthracene, 0.03mol sodium tert-butoxides, 1 × 10- 4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene is heated to reflux 24 hours, sample point plate, and reaction is complete；
Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 99.8%, yield 63.51%.
HPLC-MS：Material molecule amount is 762.26, surveys molecular weight 762.36.
The compound 49 of embodiment 20
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol2- (3- bromophenyls) -10,10- hexichol
Base -10H- anthrones, 0.03mol 9,9- dimethyl -5H, 9H-5,13b- diaza-naphthalene [3,2,1-de] anthracene, the tertiary fourths of 0.03mol
Sodium alkoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene is heated to reflux 24 hours, sample point
Plate, reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 99.8%, yield
63.51%.
HPLC-MS：Material molecule amount is 718.30, surveys molecular weight 718.37.
The compound 50 of embodiment 21
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol2- (3- bromophenyls) -10,10- diformazans
Base -10H- anthrones, 0.03mol 9,9- diphenyl -5H, 9H-5,13b- diaza-naphthalene [3,2,1-de] anthracene, the tertiary fourths of 0.03mol
Sodium alkoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene is heated to reflux 24 hours, sample point
Plate, reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 99.8%, yield
63.51%.
HPLC-MS：Material molecule amount is 718.30, surveys molecular weight 719.03.
The compound 51 of embodiment 22
The preparation method be the same as Example 20 of compound 51, difference is raw material 3,6- bis- (4- bromophenyls) -10,10-
Dimethyl -10H- anthrones replace 2- (3- bromophenyls) -10,10- diphenyl -10H- anthrones.
The compounds of this invention can be used as emitting layer material, to the compounds of this invention 8, compound 23, current material
CBP carries out the test of hot property, luminescent spectrum, fluorescence quantum efficiency and cyclic voltammetric stability, testing result such as table 1 respectively
It is shown.
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 is 20mL/min；λPLIt is sample solution fluorescence emission wavelengths, Pu Kang is opened up using Japan
SR-3 spectroradiometers are determined；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 is measured)；Cyclic voltammetric stability
It is to observe the redox characteristic of material to be identified by cyclic voltammetry；Test condition：Test sample is dissolved in volume ratio
For 2:1 dichloromethane and acetonitrile mixed solvent, concentration 1mg/mL, electrolyte is 0.1M tetrabutyl ammonium tetrafluoroborate or hexafluoro
The organic solution of phosphoric acid tetrabutylammonium.Reference electrode is Ag/Ag+ electrodes, is titanium plate to electrode, working electrode is ITO electrode, is followed
Ring number of times is 20 times.
Hot annealing conditions：WithCompound is deposited onto quartz glass/s evaporation rate, and 100 DEG C are added to after encapsulation
Baking oven in dry 72 hours, take out, be cooled to room temperature, its crystal habit observed with AFM.
From upper table data, the compounds of this invention has preferable oxidation-reduction stability, and higher heat endurance is fitted
Cooperate the material of main part for luminescent layer；Meanwhile, the compounds of this invention has suitable luminescent spectrum, higher Φ f so that application
The compounds of this invention gets a promotion as the OLED efficiency of dopant material and life-span.
The compounds of this invention combination is described in detail below by way of device embodiments 1-16 and device comparative example 1 in the devices
Application effect.Device embodiments 2-16 of the present invention, the device compared with device embodiments 1 of device comparative example 1 making
Technique is identical, and employed identical baseplate material and electrode material, except that, device survey stepped construction,
Collocation material and thicknesses of layers are different.Device stack structure is as shown in table 2.The performance test results of each device are shown in Table 3.
Device embodiments 1
Device stack structure is as shown in device architecture schematic diagram 1：Include hole transmission layer 4, luminescent layer 6, electron transfer layer
8。
Ito anode 2 (thickness of layer：150nm)/(thickness of hole transmission layer 4：120nm, material：HT6)/(thickness of luminescent layer 6：
40nm, material：Compound 1 and GD1 are by weight 90：10 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：
To ito anode layer 2 (thickness is 150nm) washing, carried out successively after progress neutralizing treatment, pure water, drying ultraviolet
Line-ozone washing is to remove the organic residue on transparent ITO surfaces.
On ito anode layer 2 after the washing, using vacuum deposition apparatus, hole transmission layer 4, hole transport is deposited
Layer material uses HT6, and thickness is 120nm, and this layer is used 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
For material of main part, GD1 is 9 as dopant material, doping mass ratio：1, luminescent layer thickness is 40nm, and this layer is used as device junction
Luminescent layer 6 in structure；
On luminescent layer 6, by vacuum evaporation mode, be deposited electron transfer layer 8, electron transport layer materials using ET2 and
EI1 mixing and dopings, doping mass ratio is 1:1, thickness is 35nm, and this layer is used as the electron transfer layer 8 in device architecture；
On electron transfer layer 8, by vacuum evaporation mode, evaporation cathode aluminium lamination, thickness is 100nm, and this layer is negative electrode
Reflection electrode layer 10 is used.
Complete after the making of OLED luminescent devices, connected anode and negative electrode as described above with known drive 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：Include hole injection layer 3, hole transmission layer 4, luminescent layer 6
With electron transfer layer 8.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：10nm, material：HI1)/hole transmission layer 4 is (thick
Degree：110nm, material：HT2)/(thickness of luminescent layer 6：40nm, material：Compound 2 and GD2 are by weight 88：12 blending structures
Into) 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：Include hole injection layer 3, hole transmission layer 4, luminescent layer
6th, electron transfer layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：10nm, material：HI2)/hole transmission layer 4 is (thick
Degree：110nm, material：HT4)/(thickness of luminescent layer 6：40nm, material：Compound 4 and GD2 are by weight 88：12 blendings are constituted)/
(the thickness of electron transfer layer 8：35nm, material：ET3 and EI1, mass ratio 1:1)/(thickness of electron injecting layer 9：1nm, material：
LiN3)/Al (thickness：100nm).
Device embodiments 4
Device stack structure is as shown in device architecture schematic diagram 1：Including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6 and electron transfer layer 8.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：10nm, material：HI1)/hole transmission layer 4 is (thick
Degree：90nm, material：HT3)/(thickness of electronic barrier layer 5：20nm, material：EB2)/(thickness of luminescent layer 6：40nm, material：Chemical combination
Thing 7 and GD3 are by weight 89：11 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：Including hole injection layer 3, hole transmission layer 4, luminescent layer
6th, electron transfer layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI3 and HT3, in mass ratio 5:
95 blendings are constituted) 4 (thickness of/hole transmission layer：70nm, material：HT3)/(thickness of luminescent layer 6：40nm, material：The He of compound 8
GD3 is by weight 89：11 blendings are constituted) 8 (thickness of/electron transfer layer：35nm, material：ET3)/(thickness of electron injecting layer 9：
1nm, material：Li)/Al (thickness：100nm).
Device embodiments 6
Device stack structure is as shown in device architecture schematic diagram 1：Including hole injection layer 3, hole transmission layer 4, luminescent layer
6th, electron transfer layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI4 and HT3, in mass ratio
5:95 blendings are constituted) 4 (thickness of/hole transmission layer：70nm, material：HT6)/(thickness of luminescent layer 6：40nm, material：Compound 17
With GD4 by weight 92：8 blendings are constituted) 8 (thickness of/electron transfer layer：35nm, material：ET4 and EI1, mass ratio 1:1)/electricity
Sub- (the thickness of implanted layer 9：1nm, material：LiF)/Al (thickness：100nm).
Device embodiments 7
Device stack structure is as shown in device architecture schematic diagram 1：Including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6, hole blocking layer 7 and electron transfer layer 8.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：10nm, material：HI1)/hole transmission layer 4 is (thick
Degree：90nm, material：HT6)/(thickness of electronic barrier layer 5：20nm, material：EB1)/(thickness of luminescent layer 6：40nm, material：Chemical combination
Thing 20 and GD4 are by weight 92：8 blendings are constituted) 7 (thickness of/hole blocking layer：20nm, material：HB1)/electron transfer layer 8 is (thick
Degree：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：Including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6, electron transfer layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI5 and HT3, in mass ratio 5:
95 blendings are constituted) 4 (thickness of/hole transmission layer：50nm, material：HT5)/(thickness of electronic barrier layer 5：20nm, material：EB3)/
(the thickness of luminescent layer 6：40nm, material：Compound 23 and GD5 are by weight 92：8 blendings are constituted) 8 (thickness of/electron transfer layer：
35nm, material：ET2 and EI1, mass ratio 1：1)/(thickness of electron injecting layer 9：1nm, material：Cs2CO3)/Al (thickness：
100nm)。
Device embodiments 9
Device stack structure is as shown in device architecture schematic diagram 1：Including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6, electron transfer layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI6 and HT4, in mass ratio 5:
95 blendings are constituted) 4 (thickness of/hole transmission layer：50nm, material：HT6)/(thickness of electronic barrier layer 5：20nm, material：EB2)/
(the thickness of luminescent layer 6：40nm, material：Compound 35 and GD6 are by weight 95：5 blendings are constituted) 8 (thickness of/electron transfer layer：
35nm, material：ET2 and EI1, mass ratio 1：1)/(thickness of electron injecting layer 9：1nm, material：EI1)/Al (thickness：100nm).
Device embodiments 10
Device stack structure is as shown in device architecture schematic diagram 1：Including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6, hole blocking layer 7, electron transfer layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：10nm, material：HI1)/hole transmission layer 4 is (thick
Degree：90nm, material：HT3)/(thickness of electronic barrier layer 5：20nm, material：EB1)/(thickness of luminescent layer 6：40nm, material：Chemical combination
Thing 38 and GD5 are by weight 92：8 blendings are constituted) 7 (thickness of/hole blocking layer：25nm, material：HB1)/electron transfer layer 8 is (thick
Degree：10nm, material：ET5)/(thickness of electron injecting layer 9：1nm, material：EI1)/Al (thickness：100nm).
Device embodiments 11
Device stack structure is as shown in device architecture schematic diagram 1：Including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6, hole blocking layer 7, electron transfer layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI5 and HT6, in mass ratio 5:
95 blendings are constituted) 4 (thickness of/hole transmission layer：50nm, material：HT6)/(thickness of electronic barrier layer 5：20nm, material：EB2)/
(the thickness of luminescent layer 6：40nm, material：Compound 41 and GD4 are by weight 92：8 blendings are constituted) 7 (thickness of/hole blocking layer：
15nm, material：HB1)/(thickness of electron transfer layer 8：20nm, 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：Including hole injection layer 3, hole transmission layer 4, luminescent layer
6th, hole blocking layer 7, electron transfer layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI5 and HT3, in mass ratio 5:
95 blendings are constituted) 4 (thickness of/hole transmission layer：70nm, material：HT6)/(thickness of luminescent layer 6：40nm, material：The He of compound 45
GD6 is by weight 95：5 blendings are constituted) 7 (thickness of/hole blocking layer：15nm, material：HB1)/(thickness of electron transfer layer 8：
20nm, material：ET6)/(thickness of electron injecting layer 9：1nm, material：CsF)/Al (thickness：100nm).
Device embodiments 13
Device stack structure is as shown in device architecture schematic diagram 1：Including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6, electron transfer layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI5 and HT3, in mass ratio 5:
95 blendings are constituted) 4 (thickness of/hole transmission layer：50nm, material：HT6)/(thickness of electronic barrier layer 5：20nm, material：EB2)/
(the thickness of luminescent layer 6：40nm, material：Compound 49 and GD2 are by weight 88：12 blendings are constituted) 8 (thickness of/electron transfer layer：
35nm, material：ET2 and EI1, mass ratio 1：1)/(thickness of electron injecting layer 9：1nm, material：CsN3)/Al (thickness：100nm).
Device embodiments 14
Device stack structure is as shown in device architecture schematic diagram 1：Including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6, hole blocking layer 7 and electron transfer layer 8.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI5 and HT3, in mass ratio 5:
95 blendings are constituted) 4 (thickness of/hole transmission layer：50nm, material：HT6)/(thickness of electronic barrier layer 5：20nm, material：EB2)/
(the thickness of luminescent layer 6：40nm, material：Compound 51, GH2 and GD2 are by weight 60：30：10 blendings are constituted)/hole blocking layer 7
(thickness 15nm, material：EB2)/(thickness of electron transfer layer 8：20nm, 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：Including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6, hole blocking layer 7 and electron transfer layer 8.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI5 and HT3, in mass ratio 5:
95 blendings are constituted) 4 (thickness of/hole transmission layer：50nm, material：HT6)/(thickness of electronic barrier layer 5：20nm, material：EB2)/
(the thickness of luminescent layer 6：40nm, material：Compound 9, GH4 and GD2 are by weight 60：30：10 blendings are constituted)/hole blocking layer 7
(thickness 15nm, material：HB1)/(thickness of electron transfer layer 8：20nm, material：ET2 and EI1, mass ratio 1：1)/Al (thickness：
100nm)。
Device embodiments 16
Device stack structure is as shown in device architecture schematic diagram 1：Including hole injection layer 3, hole transmission layer 4, luminescent layer
6th, electron transfer layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI4 and HT3, in mass ratio 5:
95 blendings are constituted) 4 (thickness of/hole transmission layer：70nm, material：HT6)/(thickness of luminescent layer 6：40nm, material：GH3 and chemical combination
Thing 45 is by weight 92：8 blendings are constituted) 8 (thickness of/electron transfer layer：35nm, material：ET4 and EI1, mass ratio 1:1)/electronics
(the thickness of implanted layer 9：1nm, material：LiF)/Al (thickness：100nm).
Device comparative example 1
Device stack structure is as shown in device architecture schematic diagram 1：Including hole transmission layer 4, luminescent layer 6, electron transfer layer 8
With electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole transmission layer 4：120nm, material：HTI)/(thickness of luminescent layer 6：
40nm, material：GH1 and GD1 is by weight 90：10 blendings are constituted) 8 (thickness of/electron transfer layer：35nm, material：ET1)/electronics
(the thickness of implanted layer 9：1nm, 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
Calculate, and the measurement life-span.It is determined that 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：Device detection performance is using comparative example 1 as reference, and the device property indices of comparative example 1 are set to 1.0.Compare
The current efficiency of example 1 is 32.6cd/A (@1000cd/m2)；Driving voltage is 5.6v (@1000cd/m2)；CIE chromaticity coordinates is
(0.34,0.63)；LT95 life time decays are 3.5Hr under 5000 brightness.
Table 3 summarizes the OLED in 1000cd/m2Voltage needed for brightness, the current efficiency reached, Yi Ji
5000cd/m2LT95 Decays under brightness.
The comparative device comparative example 1 of device embodiments 1, changes the emitting layer material of the present invention, and by the material group of the present invention
Synthesize after laminated device, device voltage reduction, current efficiency lifting 50%, 1.5 times of life-span upgrading；Device embodiments 2-16 is by this
Invent material adapted and the device stack combination of design so that device data is further lifted；Such as the institute of device embodiments 14,15
Show, when anthrone class material of the invention is as hybrid agent material, further obtain extraordinary performance data；Such as device
Shown in embodiment 16, anthrone class material of the present invention is as luminescent layer dopant material in use, equally obtaining extraordinary performance
Data.
To sum up, presently preferred embodiments of the present invention is the foregoing is only, is not intended to limit the invention, all essences in the present invention
God is with principle, and any modification, equivalent substitution and improvements made etc. should be included in the scope of the protection.
Claims (14)
1. a kind of organic electroluminescence device containing anthracene ketone compounds, the device includes hole transmission layer, luminescent layer, electronics
Transport layer, it is characterised in that the device emitting layer material includes the compound containing anthrone group, the structural formula of the compound
As shown in formula (1)：
In formula (1), D1、D2Selection C independently1-10Straight or branched alkyl, phenyl, xenyl, terphenyl, naphthyl
Or anthryl, D1、D2Can be with identical or different；N takes 1 or 2；
Described-(R)nExpression is connected on any carbon atom on the phenyl ring of formula (1) both sides；
In formula (1), R is represented using formula (2) or formula (3)：
Wherein, Ar represents C6-30Aromatic radical, furyl, thienyl, pyrrole radicals, quinolyl or isoquinolyl；X1For oxygen atom,
Sulphur atom, selenium atom, C1-10The alkylidene of straight or branched alkyl substitution, the alkylidene of aryl substitution, alkyl or aryl substitution
Amido in one kind；
Wherein, R1、R2Structure shown in selection hydrogen or formula (4) independently：
A isX2、X3It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Straight or branched alkyl
One kind in substituted alkylidene, the alkylidene of aryl substitution, the amido of alkyl or aryl substitution；A and CL1-CL2Key, CL2-CL3
Key, CL3-CL4Key, CL4-CL5Key, CL‘1-CL’2Key, CL‘2-CL’3Key, CL‘3-CL’4Key or CL‘4-CL’5Key is connected.
2. organic electroluminescence device according to claim 1, it is characterised in that when a is represented in the compoundAnd and CL4-CL5Key or CL‘4-CL’5When key is connected, X1And X2Location overlap, only take X1Or X2；X3It is expressed as oxygen former
Son, sulphur atom, selenium atom, C1-10Alkylidene, alkylidene, the alkyl or aryl of aryl substitution of straight or branched alkyl substitution take
One kind in the amido in generation.
3. organic electroluminescence device according to claim 1, it is characterised in that the general structure of the compound is：
4. organic electroluminescence device according to claim 1, it is characterised in that R is in the formula (1)：
Any of.
5. organic electroluminescence device according to claim 1, it is characterised in that the concrete structure formula of the compound is：
6. organic electroluminescence device according to claim 1, it is characterised in that the material conduct shown in the formula (1)
The material of main part of luminescent layer；The dopant material of the luminescent layer uses material shown in general formula (13), (14), (15) or (16)
In one kind：
In formula (13), B1-B10 selections are hydrogen, C1-30Straight or branched alkyl substitution alkyl or alkoxy, substitution or do not take
The C in generation6-30Aryl, substituted or unsubstituted 3 yuan to 30 unit's heteroaryls；It is hydrogen when B1-B10 is different；
In formula (14), the one kind for being expressed as oxygen, carbon, nitrogen-atoms of Y1-Y6 independently； Point
The group containing two atoms is not expressed as is connected cyclic by any chemical bond；
Respective independent one kind for being expressed as oxygen, carbon, nitrogen-atoms of Y1-Y4 in formula (15), formula (16)；It is expressed as the group containing two atoms and is connected cyclic by any chemical bond.
7. 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 structure such as formula (17) of the compound：
D1-D3 each independently represents substituted or unsubstituted C in formula (17)6-30Aryl, substituted or unsubstituted 3 yuan to 30 yuan
Heteroaryl；D1-D3 can be with identical or difference.
8. 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 formula (18), (19), (20), (21) or (22)：
E1-E10 selections are hydrogen, C in formula (18), formula (19), formula (20), formula (21), formula (22)1-30Straight chain or branch
The alkyl or alkoxy, substituted or unsubstituted C of alkyl group substitution6-30Aryl, substituted or unsubstituted 3 yuan to 30 yuan heteroaryls
Base；It is hydrogen when E1-E10 is different.
9. organic electroluminescence device according to claim 1, it is characterised in that the luminescent device also includes hole and noted
Enter layer；The hole injection layer material is one kind in having structure formula (23), (24), material shown in (25)：
In formula (23), F1-F3 each independently represents substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 3 yuan to 30 yuan
Heteroaryl；F1-F3 can be with identical or difference；
In formula (24), formula (25), G1-G6 each independent expression hydrogen, itrile group, halogen, amide groups, alkoxy, ester group, nitre
Base, C1-30Carbon atom, the substituted or unsubstituted C of straight or branched alkyl substitution6-30Aryl, 3 yuan to 30 unit's heteroaryls, G1-G6
It is asynchronously hydrogen.
10. organic electroluminescence device according to claim 1, it is characterised in that the luminescent device also includes electronics and noted
Enter layer；The electron injecting layer material is one kind in lithium, lithium salts or cesium salt；The lithium salts be 8-hydroxyquinoline lithium, lithium fluoride,
Lithium carbonate, Lithium Azide；The cesium salt is cesium fluoride, cesium carbonate, cesium azide.
11. according to the organic electroluminescence device described in claim 1, it is characterised in that the dopant material of the luminescent layer is with lighting
The mass ratio of the material of main part of layer is 0.005~0.2:1.
12. organic electroluminescence device according to claim 1, it is characterised in that compound shown in the formula (1) is also
It can be used as the dopant material of luminescent layer.
13. a kind of application of any one of claim 1~12 organic electroluminescence device, it is characterised in that the Organic Electricity
Electroluminescence device is used to prepare top-illuminating OLED luminescent device.
14. a kind of application of any one of claim 1~12 organic electroluminescence device, it is characterised in that the Organic Electricity
Electroluminescence device is applied to AM-OLED displays.
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