CN107068911B - 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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- 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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- 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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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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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
- 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 devices 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 of the compound such as general formula (1).Anthrone class material of the present invention is because have lesser 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 dopant material is selected as fluorescent material, it is easier to obtain the luminous radiation of dopant material, to be easier to obtain the long-life of material.
Description
Technical field
The present invention relates to technical field of semiconductors, are the organic of anthracene ketone compounds more particularly, to a kind of emitting layer material
Electroluminescent device and its application.
Background technique
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology can both be used to make
New display product is made, production novel illumination product is can be used for, is expected to substitute existing liquid crystal display and fluorescent lighting,
Application prospect is very extensive.
Structure of the OLED luminescent device like 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 depending on the application collectively constitutes OLED luminescent device together.
As current device, when the two end electrodes application voltage to OLED luminescent device, 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, i.e. generation OLED electroluminescent.
Application of the Organic Light Emitting Diode (OLED) in terms of large-area flat-plate is shown and is illuminated causes industry 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 lower (up to 25%).External quantum efficiency is generally lower than 5%, and there are also very big with the efficiency of phosphorescent devices
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 it in the application of 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 poor (the △ E of small 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 achieve 100%.Meanwhile material structure is controllable, and property is stablized, and it is 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 material, following problem there are in fact:
(1) T1 the and S1 state for designing molecule has strong CT feature, very small S1-T1 state energy gap, although can pass through
TADF process realizes high T1→S1State exciton conversion ratio, but low S1 state radiation transistion rate is also resulted in, consequently it is difficult to have both
(or realizing simultaneously) Gao Jizi utilization rate and high fluorescent radiation efficiency；
(2) even if doping device has been used to mitigate T exciton concentration quenching effect, 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.
Summary of the invention
In view of the above-mentioned problems existing in the prior art, the present invention provides a kind of organic electroluminescences containing anthracene ketone compounds
Luminescent device.The present invention is based on the anthracene ketone compounds of TADF mechanism as emitting layer material applied to Organic Light Emitting Diode
On, there are good photoelectric properties, can satisfy OLED device enterprise, especially OLED display panel and OLED Illumination Enterprise
Demand.
Technical scheme is as follows:
A kind of organic electroluminescence device containing anthracene ketone compounds, the device include hole transmission layer, luminescent layer, electricity
Sub- transport layer, the device emitting layer material include the compound containing anthrone group, the structural formula of the compound such as general formula (1)
It is shown:
In general formula (1), D1、D2Selection C independently1-10Linear or branched alkyl group, phenyl, xenyl, terphenyl,
Naphthalene or anthryl, D1、D2It can be identical or different；N takes 1 or 2；
Described-(R)nExpression is connected on any carbon atom on the phenyl ring of general formula (1) two sides；
In general formula (1), R is indicated using general formula (2) or general formula (3):
Wherein, Ar indicates C6-30Aromatic radical, furyl, thienyl, pyrrole radicals, quinolyl or isoquinolyl；X1For oxygen original
Son, sulphur atom, selenium atom, C1-10Alkylidene, the alkyl or aryl of alkylidene, aryl substitution that linear or branched alkyl group replaces take
One of the amido in generation；
Wherein, R1、R2Structure shown in selection hydrogen or general formula (4) independently:
A isX2、X3It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Linear chain or branched chain
One of the amido that alkyl-substituted alkylidene, the alkylidene of aryl substitution, alkyl or aryl replace；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 connection.
When a is indicated in the compoundAnd and CL4-CL5Key or CL‘4-CL’5When key connection, 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 linear or branched alkyl group substitution
One of the amido that alkylidene, the alkyl or aryl of base substitution replace；A passes through CL4-CL5Key or CL‘4-CL’5Key connection is logical
On the intermediate phenyl ring of formula (2) or general formula (3).
The general structure of the compound are as follows:
R in the general formula (1) are as follows:
In
It is any.The concrete structure formula of the compound are as follows:
Material of main part of the material as luminescent layer shown in the general formula (1)；Under the dopant material use of the luminescent layer
One of material shown in column general formula (13), (14), (15) or (16):
In general formula (13), B1-B10 is selected as hydrogen, C1-30Linear or branched alkyl group replace alkyl or alkoxy, replace or
Unsubstituted C6-30Aryl, it is substituted or unsubstituted 3 yuan to 30 unit's heteroaryls；B1-B10 is not hydrogen simultaneously；
In general formula (14), the one kind for being expressed as oxygen, carbon, nitrogen-atoms of Y1-Y6 independently； It is expressed as containing there are two the groups of atom to pass through the connected cyclization of any chemical bond；
Y1-Y4 one kind independent for being expressed as oxygen, carbon, nitrogen-atoms in general formula (15), general formula (16)；It is expressed as containing there are two the groups of atom to pass through the connected cyclization of any chemical bond.
The material of the hole transmission layer is the compound containing triarylamine group, the structure of the compound such as general formula
(17) shown in:
D1-D3 respectively independently indicates substituted or unsubstituted C in general formula (17)6-30Aryl, it is substituted or unsubstituted 3 yuan extremely
30 unit's heteroaryls；D1-D3 can be same or different.
The material of the electron transfer layer is one in material shown in general formula (18), (19), (20), (21) or (22)
Kind:
General formula (18), general formula (19), general formula (20), general formula (21), E1-E10 is selected as hydrogen, C in general formula (22)1-30Straight chain
Or alkyl or alkoxy, substituted or unsubstituted C that branched alkyl replaces6-30Aryl, substituted or unsubstituted 3 yuan to 30 yuan it is miscellaneous
Aryl；E1-E10 is not hydrogen simultaneously.
The organic electroluminescence device further includes hole injection layer；The hole injection layer material is logical for having structure
One of formula (23), (24), material shown in (25):
In general formula (23), 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 same or different；
In general formula (24), general formula (25), G1-G6 expression hydrogen independent, 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,
G1-G6 is not hydrogen simultaneously.
The organic electroluminescence device further includes electron injecting layer；The electron injecting layer material is lithium, lithium salts
Or one of 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 material of main part of the dopant material and luminescent layer of the luminescent layer is 0.005~0.2:1.
Compound shown in the general formula (1) can also be used as the dopant material of luminescent layer.
A kind of application of the organic electroluminescence device, is used to prepare top-illuminating OLED luminescent device.
A kind of application of the organic electroluminescence device is applied to AM-OLED display.
The present invention is beneficial to be had the technical effect that
The anthracene ketone compounds for forming OLED luminescent device of the present invention have the design feature of TADF, easy to accomplish non-
Often small S1-T1 state energy gap is poor, and in excitation, the anti-intersystem crossing of triplet state easy to accomplish to singlet makes originally not
It can shine, dispersed heat is converted into the energy that can produce luminous energy in the form of heat, and is expected to obtain high efficiency.
It is analyzed based on principles above, OLED luminescent device of the present invention, both can choose fluorescent material as doping material
Material, also can choose phosphor material as dopant material, can also be by TADF material of the present invention directly as dopant material
It uses.
Material of main part collocation iridium of the anthracene ketone compounds as OLED luminescent device, platinum class phosphor material or anthracene class are glimmering
Luminescent material in use, device current efficiency, power efficiency and external quantum efficiency are greatly improved；Meanwhile for device
Life-span upgrading is clearly.Further, on OLED device layer structure matching, after introducing 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 or more layers, and the hole transmission layer of adjacent luminescent layer side can be named as electronic barrier layer (EBL) again, provides electricity
Sub- barrier effect promotes exciton combined efficiency in luminescent layer, and the hole transmission layer of adjacent hole injection layer side then plays sky
Cave 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 the compound effect of exciton in luminescent layer
Rate is promoted, and the electron transfer layer of adjacent electron injecting layer side then plays the role of electron-transport and reduces exciton transfer barrier.
It should be mentioned, however, 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, function
Rate efficiency, external quantum efficiency are further enhanced, and it is obvious that device lifetime promotes effect.Have in OLED luminescent device 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 mesh
, and lead to the improvement of organic electroluminescence device, especially voltage, efficiency and the improvement in service life.This is especially suitable for red
The electroluminescent device of color or green phosphorescent, especially when using device architecture and combination of materials of the invention, situation is such.
Detailed description of the invention
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 embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
1 compound 1 of embodiment
0.01mol 3- (4- bromophenyl) -10,10- diformazan is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
Base -10H- anthrone, 0.03mol 9,9- dimethyl acridinium, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10- 4Mol tri-tert-butylphosphine, 150ml toluene are heated to reflux 24 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate
Revolving crosses silicagel column, obtains target product, purity 95.2%, yield 77.00%.
HPLC-MS: material molecule amount 505.24 surveys molecular weight 505.29.
2 compound 2 of embodiment
0.01mol 3- (3- bromophenyl) -10,10- diformazan is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
Base -10H- anthrone, 0.03mol phenoxazine, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4The tertiary fourth of mol tri-
Base phosphine, 150ml toluene are heated to reflux 24 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silica gel
Column obtains target product, purity 99.20%, yield 73.50%.
HPLC-MS: material molecule amount 479.19 surveys molecular weight 479.46.
3 compound 4 of embodiment
0.01mol 3, bromo- 10, the 10- diphenyl-of 6- bis- is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
10H- anthrone, 0.03mol 5- phenyl azophenlyene, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Tri- uncle of mol
Butyl phosphine, 150ml toluene are heated to reflux 24 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicon
Rubber column gel column obtains target product, purity 99.1%, yield 73.60%.
HPLC-MS: material molecule amount 858.34 surveys molecular weight 858.52.
4 compound 5 of embodiment
Bromo- 10, the 10- dimethyl -10H- anthracene of 0.01mol 2- is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
Ketone, 0.03mol 9,9- diphenylacridine, 0.03mol sodium tert-butoxide, 01 × 10-4mol Pd2(dba)3, 1 × 10-4Tri- uncle of mol
Butyl phosphine, 150ml toluene are heated to reflux 24 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicon
Rubber column gel column obtains target product, purity 99.325%, yield 63.56%.
HPLC-MS: material molecule amount 553.24 surveys molecular weight 553.53.
5 compound 7 of embodiment
0.01mol 3- (4- bromophenyl) -10,10- diformazan is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
Base -10H- anthrone, 0.03mol acridine spiral shell anthrone, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-
Tert-butyl phosphine, 150ml toluene are heated to reflux 24 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, mistake
Silicagel column obtains target product, purity 98.50%, yield 63.25%.
HPLC-MS: material molecule amount 655.25 surveys molecular weight 655.66.
6 compound 8 of embodiment
0.01mol2- (4- bromophenyl) -10,10- diformazan is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
Base -10H- anthrone, 0.03mol 6,6- dimethyl -6,11- dihydro -13- oxa- -11- azepine-indoles and anthracene, the tertiary fourth of 0.03mol
Sodium alkoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene are heated to reflux 24 hours, sample point
Plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity 99.33%, yield
72.50%.
HPLC-MS: material molecule amount 595.25 surveys molecular weight 595.32.
7 compound 9 of embodiment
0.01mol3, bromo- 10, the 10- dimethyl-of 6- bis- is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
10H- anthrone, 0.03mol 6,6- dimethyl -6,11- dihydro -13- oxa- -11- azepine-indoles and anthracene, the 0.03mol tert-butyl alcohol
Sodium, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene are heated to reflux 24 hours, sample contact plate,
Fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity 99..20%, yield
68.20%.
HPLC-MS: material molecule amount 816.34 surveys molecular weight 816.56.
8 compound 15 of embodiment
0.01mol1- (3- bromophenyl) -10,10- diformazan is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
Base -10H- anthrone, 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-tert-butylphosphine, 150ml toluene are heated to reflux 24 hours, take
Sampling point plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity 99.55%, yield
63.50%.
HPLC-MS: material molecule amount 670.30 surveys molecular weight 670.61.
9 compound 17 of embodiment
0.01mol2,7- bis- (4- bromophenyl) -10,10- bis- is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
Methyl-1 0H- anthrone, 0.03mol 11,11- dimethyl -6,11- dihydro -13- oxa- -6- azepine-indoles [1,2-b] anthracene,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene, is heated to reflux 24
Hour, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity
98.62%, yield 72.3%.
HPLC-MS: material molecule amount 968.40 surveys molecular weight 968.94.
10 compound 19 of embodiment
0.01mol2- (5- bromine furans -2- base) -10,10- is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
Dimethyl -10H- anthrone, 0.03mol 6H-11- oxa- -13- thia -6- azepine-indoles [1,2-b] anthracene, the 0.03mol tert-butyl alcohol
Sodium, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene are heated to reflux 24 hours, sample contact plate,
Fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity 99.20%, yield 62.3%.
HPLC-MS: material molecule amount 575.16 surveys molecular weight 575.33.
11 compound 20 of embodiment
0.01mol3- (the bromo- 1- methyl-1 H- pyrroles -2- of 5- is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
Base) -10,10- dimethyl -10H- anthrone, 0.03mol 13,13- dimethyl -6,13- dihydro -11- oxa- -6- azepine-indoles
[1,2-b] anthracene, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene,
It is heated to reflux 24 hours, samples contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target production
Object, purity 99.6%, yield 68.00%.
HPLC-MS: material molecule amount 598.26 surveys molecular weight 598.35.
12 compound 21 of embodiment
0.01mol3- (8- bromoquinoline -5- base) -10,10- is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
Dimethyl -10H- anthrone, 0.03mol 11,11- dimethyl -13- 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-tert-butylphosphine, 150ml toluene, is heated to reflux 24
Hour, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity
99.8%, yield 63.51%.
HPLC-MS: material molecule amount 721.31 surveys molecular weight 721.36.
13 compound 23 of embodiment
0.01mol3- (4- bromophenyl) -10,10- hexichol is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
Base -10H- anthrone, 0.03mol 13,13- dimethyl -5,13- dihydro -8- oxa- -5- azepine-indoles [1,2-a] anthracene,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene, is heated to reflux 24
Hour, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity
99.8%, yield 63.51%.
HPLC-MS: material molecule amount 719.28 surveys molecular weight 719.38.
14 compound 31 of embodiment
The preparation method is the same as that of Example 1 for compound 31, the difference is that raw material 5,5- diphenyl -5,8a, 12a, 13- tetra-
Hydrogen -8- oxa- -13- azepine-indoles [1,2-a] anthracene replacement acridine and anthrone.
15 compound 35 of embodiment
The preparation method is the same as that of Example 1 for compound 35, the difference is that raw material 14,14- dimethyl -5,14- dihydro-naphthalene
And [2,3-b] acridine replaces 9,9-dimethylacridan.
16 compound 38 of embodiment
The preparation method is the same as that of Example 13 for compound 38, the difference is that raw material 14,14- dimethyl -7,14- dihydro -
5,12- dioxa -7- azepine-pentacene replaces 13,13- dimethyl -5,13- dihydro -8- oxa- -5- azepine-indoles [1,2-a]
Anthracene.
17 compound 40 of embodiment
The preparation method of compound 40 is with embodiment 7, the difference is that raw material 14,14- dimethyl -7,14- dihydro -5,
12- dioxa -7- azepine-pentacene replacement 6,6- dimethyl -6,11- dihydro -13- oxa- -11- azepine-indoles and anthracene.
18 compound 41 of embodiment
The preparation method is the same as that of Example 13 for compound 38, the difference is that raw material A replaces 13,13- dimethyl -5,13-
Dihydro -8- oxa- -5- azepine-indoles [1,2-a] anthracene.
19 compound 45 of embodiment
0.01mol3, bromo- 10, the 10- dimethyl-of 6- bis- is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
10H- anthrone, 0.03mol 9H-5- oxa- -9,13b- diaza-naphthalene [3,2,1-de] anthracene, 0.03mol sodium tert-butoxide, 1 × 10- 4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene are heated to reflux 24 hours, sample contact plate, fully reacting；
Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity 99.8%, yield 63.51%.
HPLC-MS: material molecule amount 762.26 surveys molecular weight 762.36.
20 compound 49 of embodiment
0.01mol2- (3- bromophenyl) -10,10- hexichol is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
Base -10H- anthrone, 0.03mol 9,9- dimethyl -5H, 9H-5,13b- diaza-naphthalene [3,2,1-de] anthracene, the tertiary fourth of 0.03mol
Sodium alkoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene are heated to reflux 24 hours, sample point
Plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity 99.8%, yield
63.51%.
HPLC-MS: material molecule amount 718.30 surveys molecular weight 718.37.
21 compound 50 of embodiment
0.01mol2- (3- bromophenyl) -10,10- diformazan is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
Base -10H- anthrone, 0.03mol 9,9- diphenyl -5H, 9H-5,13b- diaza-naphthalene [3,2,1-de] anthracene, the tertiary fourth of 0.03mol
Sodium alkoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene are heated to reflux 24 hours, sample point
Plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity 99.8%, yield
63.51%.
HPLC-MS: material molecule amount 718.30 surveys molecular weight 719.03.
22 compound 51 of embodiment
The preparation method of compound 51 is with embodiment 20, the difference is that raw material 3,6- bis- (4- bromophenyl) -10,10-
Dimethyl -10H- anthrone replaces 2- (3- bromophenyl) -10,10- diphenyl -10H- anthrone.
The compounds of this invention can be used as emitting layer material use, 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 20mL/min；λPLIt is sample solution fluorescence emission wavelengths, opens up Pu Kang using Japan
The measurement of SR-3 spectroradiometer；Φ f is 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 sphere and marine optics LLS-LED the light source composition of Lan Fei company, the U.S.
Sub- efficiency test system, reference literature Adv.Mater.1997,9,230-232 method are measured)；Cyclic voltammetric stability
It is that the redox characteristic of material is observed by cyclic voltammetry to be identified；Test condition: test sample is dissolved in volume ratio
For the methylene chloride and acetonitrile mixed solvent of 2:1, concentration 1mg/mL, electrolyte is the tetrabutyl ammonium tetrafluoroborate or hexafluoro of 0.1M
The organic solution of phosphoric acid tetrabutylammonium.Reference electrode is Ag/Ag+ electrode, is titanium plate to electrode, working electrode is ITO electrode, is followed
Ring number is 20 times.
Hot annealing conditions: withCompound is deposited onto quartz glass the evaporation rate of/s, and 100 DEG C are added to after encapsulation
Baking oven in dry 72 hours, take out, be cooled to room temperature, observe its crystal habit with AFM.
By upper table data it is found that the compounds of this invention has preferable oxidation-reduction stability, higher thermal stability is fitted
Cooperation is the material of main part of luminescent layer；Meanwhile the compounds of this invention have suitable luminescent spectrum, higher Φ f so that using
The compounds of this invention gets a promotion as the OLED device efficiency of dopant material and service life.
In the devices below by way of device embodiments 1-16 and device comparative example 1 the present invention will be described in detail compound combination
Application effect.The production of device embodiments 2-16, the device compared with device embodiments 1 of device comparative example 1 of the present invention
Technique is identical, and uses identical baseplate material and electrode material, the difference is 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: including hole transmission layer 4, luminescent layer 6, electron transfer layer
8。
Ito anode layer 2 (thickness: 150nm)/hole transmission layer 4 (thickness: 120nm, material: HT6)/luminescent layer 6 (thickness:
40nm, material: compound 1 and GD1 are constituted by weight 90:10 blending)/electron transfer layer 8 (thickness: 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 successively carried out after progress neutralizing treatment, pure water, drying ultraviolet
Line-ozone washing is to remove the organic residue on the transparent surface ITO.
On the ito anode layer 2 after the washing, using vacuum deposition apparatus, hole transmission layer 4, hole transport is deposited
Layer material uses HT6, and film thickness 120nm, 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 GD1 as dopant material, doping mass ratio is 9:1, and 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 8, electron transport layer materials using ET2 and
EI1 mixing and doping, doping mass ratio are 1:1, and 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 layer, film thickness 100nm, this layer is cathode
Reflection electrode layer 10 uses.
After completing the production of OLED luminescent device 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: including hole injection layer 3, hole transmission layer 4, luminescent layer 6
With electron transfer layer 8.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HI1)/hole transmission layer 4 is (thick
Degree: 110nm, material: HT2) (thickness: 40nm, material: compound 2 and GD2 are by weight 88:12 blending structure for/luminescent layer 6
At)/electron transfer layer 8 (thickness: 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: including hole injection layer 3, hole transmission layer 4, luminescent layer
6, electron transfer layer 8 and electron injecting layer 9.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HI2)/hole transmission layer 4 is (thick
Degree: 110nm, material: HT4)/luminescent layer 6 (thickness: 40nm, material: compound 4 and GD2 are constituted by weight 88:12 blending)/
Electron transfer layer 8 (thickness: 35nm, material: ET3 and EI1, mass ratio 1:1)/electron injecting layer 9 (thickness: 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 layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HI1)/hole transmission layer 4 is (thick
Degree: 90nm, material: HT3)/electronic barrier layer 5 (thickness: 20nm, material: EB2) (thickness: 40nm, material: chemical combination of/luminescent layer 6
Object 7 and GD3 are constituted by weight 89:11 blending)/electron transfer layer 8 (thickness: 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
6, electron transfer layer 8 and electron injecting layer 9.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 50nm, material: HI3 and HT3, in mass ratio 5:
95 blendings are constituted)/hole transmission layer 4 (thickness: 70nm, material: HT3)/luminescent layer 6 (thickness: 40nm, material: 8 He of compound
GD3 is constituted by weight 89:11 blending)/electron transfer layer 8 (thickness: 35nm, material: ET3)/electron injecting layer 9 (thickness:
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
6, electron transfer layer 8 and electron injecting layer 9.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 50nm, material: HI4 and HT3, in mass ratio
5:95 blending is constituted)/hole transmission layer 4 (thickness: 70nm, material: HT6) (thickness: 40nm, material: compound 17 of/luminescent layer 6
Constituted with GD4 by weight 92:8 blending)/electron transfer layer 8 (thickness: 35nm, material: ET4 and EI1, mass ratio 1:1)/electricity
Sub- implanted layer 9 (thickness: 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 layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HI1)/hole transmission layer 4 is (thick
Degree: 90nm, material: HT6)/electronic barrier layer 5 (thickness: 20nm, material: EB1) (thickness: 40nm, material: chemical combination of/luminescent layer 6
Object 20 and GD4 are constituted by weight 92:8 blending)/hole blocking layer 7 (thickness: 20nm, material: HB1)/electron transfer layer 8 (thickness
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 layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 50nm, material: HI5 and HT3, in mass ratio 5:
95 blendings are constituted)/hole transmission layer 4 (thickness: 50nm, material: HT5)/electronic barrier layer 5 (thickness: 20nm, material: EB3)/
Luminescent layer 6 (thickness: 40nm, material: compound 23 and GD5 are constituted by weight 92:8 blending)/electron transfer layer 8 (thickness:
35nm, material: ET2 and EI1, mass ratio 1:1)/electron injecting layer 9 (thickness: 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 layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 50nm, material: HI6 and HT4, in mass ratio 5:
95 blendings are constituted)/hole transmission layer 4 (thickness: 50nm, material: HT6)/electronic barrier layer 5 (thickness: 20nm, material: EB2)/
Luminescent layer 6 (thickness: 40nm, material: compound 35 and GD6 are constituted by weight 95:5 blending)/electron transfer layer 8 (thickness:
35nm, material: ET2 and EI1, mass ratio 1:1)/electron injecting layer 9 (thickness: 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 layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HI1)/hole transmission layer 4 is (thick
Degree: 90nm, material: HT3)/electronic barrier layer 5 (thickness: 20nm, material: EB1) (thickness: 40nm, material: chemical combination of/luminescent layer 6
Object 38 and GD5 are constituted by weight 92:8 blending)/hole blocking layer 7 (thickness: 25nm, material: HB1)/electron transfer layer 8 (thickness
Degree: 10nm, material: ET5)/electron injecting layer 9 (thickness: 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 layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 50nm, material: HI5 and HT6, in mass ratio 5:
95 blendings are constituted)/hole transmission layer 4 (thickness: 50nm, material: HT6)/electronic barrier layer 5 (thickness: 20nm, material: EB2)/
Luminescent layer 6 (thickness: 40nm, material: compound 41 and GD4 are constituted by weight 92:8 blending)/hole blocking layer 7 (thickness:
15nm, material: HB1)/electron transfer layer 8 (thickness: 20nm, material: ET2 and EI1, mass ratio 1:1)/electron injecting layer 9 (thickness
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
6, hole blocking layer 7, electron transfer layer 8 and electron injecting layer 9.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 50nm, material: HI5 and HT3, in mass ratio 5:
95 blendings are constituted)/hole transmission layer 4 (thickness: 70nm, material: HT6)/luminescent layer 6 (thickness: 40nm, material: 45 He of compound
GD6 is constituted by weight 95:5 blending)/hole blocking layer 7 (thickness: 15nm, material: HB1)/electron transfer layer 8 (thickness:
20nm, material: ET6)/electron injecting layer 9 (thickness: 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 layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 50nm, material: HI5 and HT3, in mass ratio 5:
95 blendings are constituted)/hole transmission layer 4 (thickness: 50nm, material: HT6)/electronic barrier layer 5 (thickness: 20nm, material: EB2)/
Luminescent layer 6 (thickness: 40nm, material: compound 49 and GD2 are constituted by weight 88:12 blending)/electron transfer layer 8 (thickness:
35nm, material: ET2 and EI1, mass ratio 1:1)/electron injecting layer 9 (thickness: 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 layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 50nm, material: HI5 and HT3, in mass ratio 5:
95 blendings are constituted)/hole transmission layer 4 (thickness: 50nm, material: HT6)/electronic barrier layer 5 (thickness: 20nm, material: EB2)/
Luminescent layer 6 (thickness: 40nm, material: compound 51, GH2 and GD2 are constituted by weight 60:30:10 blending)/hole blocking layer 7
(thickness 15nm, material: EB2)/electron transfer layer 8 (thickness: 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 layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 50nm, material: HI5 and HT3, in mass ratio 5:
95 blendings are constituted)/hole transmission layer 4 (thickness: 50nm, material: HT6)/electronic barrier layer 5 (thickness: 20nm, material: EB2)/
Luminescent layer 6 (thickness: 40nm, material: compound 9, GH4 and GD2 are constituted by weight 60:30:10 blending)/hole blocking layer 7
(thickness 15nm, material: HB1)/electron transfer layer 8 (thickness: 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
6, electron transfer layer 8 and electron injecting layer 9.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 50nm, material: HI4 and HT3, in mass ratio 5:
95 blendings are constituted)/hole transmission layer 4 (thickness: 70nm, material: HT6) (thickness: 40nm, material: GH3 and chemical combination of/luminescent layer 6
Object 45 is constituted by weight 92:8 blending)/electron transfer layer 8 (thickness: 35nm, material: ET4 and EI1, mass ratio 1:1)/electronics
Implanted layer 9 (thickness: 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 layer 2 (thickness: 150nm)/hole transmission layer 4 (thickness: 120nm, material: HTI)/luminescent layer 6 (thickness:
40nm, material: GH1 and GD1 is constituted by weight 90:10 blending)/electron transfer layer 8 (thickness: 35nm, material: ET1)/electronics
Implanted layer 9 (thickness: 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 the measurement 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 performance indexes of comparative example is set as 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 decay is 3.5Hr under 5000 brightness.
Table 3 summarizes the OLED device in 1000cd/m2Voltage needed for brightness, the current efficiency reached, Yi Ji
5000cd/m2LT95 Decay under brightness.
1 comparative device comparative example 1 of device embodiments replaces emitting layer material of the invention, and presses material group of the invention
After synthesizing laminated device, device voltage is reduced, current efficiency promotion 50%, and 1.5 times of life-span upgrading；Device embodiments 2-16 is by this
Material adapted and the device stack combination for inventing design, so that device data is further promoted；Such as 14,15 institute of device embodiments
Show, when anthrone class material of the invention is as hybrid agent material, further obtains 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, the foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention
Within mind and principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (14)
1. a kind of organic electroluminescence device containing anthracene ketone compounds, which 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 general formula (1):
In general formula (1), D1、D2Selection C independently1-10Linear or branched alkyl group, phenyl, xenyl, terphenyl, naphthalene
Or anthryl, D1、D2It can be identical or different；N takes 1 or 2；
Described-(R)nExpression is connected on any carbon atom on the phenyl ring of general formula (1) two sides；
In general formula (1), R is indicated using general formula (2) or general formula (3):
Wherein, Ar indicates C6-30Aromatic radical, furyl, thienyl, pyrrole radicals, quinolyl or isoquinolyl；X1For oxygen atom,
One of the amido that sulphur atom, selenium atom, methyl substituted alkylidene, the alkylidene of phenyl substitution, phenyl replace；
Wherein, R1、R2Structure shown in selection hydrogen or general formula (4) independently:
A isX2、X3Be expressed as oxygen atom, sulphur atom, selenium atom, methyl substituted alkylidene,
One of the amido that alkylidene, the phenyl of phenyl substitution replace；A and CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL4-CL5
Key, CL‘1-CL’2Key, CL‘2-CL’3Key, CL‘3-CL’4Key or CL‘4-CL’5Key connection.
2. organic electroluminescence device according to claim 1, it is characterised in that when a is indicated in the compoundAnd and CL4-CL5Key or CL‘4-CL’5When key connection, X1And X2Position overlapping, only take X1Or X2；X3It is expressed as oxygen original
One of the amido that son, sulphur atom, selenium atom, methyl substituted alkylidene, the alkylidene of phenyl substitution, phenyl replace.
3. organic electroluminescence device according to claim 1, it is characterised in that the general structure of the compound are as follows:
4. organic electroluminescence device according to claim 1, it is characterised in that R in the general formula (1) are as follows:
In appoint
It is a kind of.
5. organic electroluminescence device according to claim 1, it is characterised in that the concrete structure formula of the compound are as follows:
6. organic electroluminescence device according to claim 1, it is characterised in that material conduct shown in the general 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)
One of:
In general formula (13), B1-B10 is selected as hydrogen, C1-30The alkyl or alkoxy of linear or branched alkyl group substitution replace or do not take
The C in generation6-30Aryl, it is substituted or unsubstituted 3 yuan to 30 unit's heteroaryls；B1-B10 is not hydrogen simultaneously；
In general formula (14), the one kind for being expressed as oxygen, carbon, nitrogen-atoms of Y1-Y6 independently； Point
It is not expressed as containing there are two the groups of atom to pass through the connected cyclization of any chemical bond；
Y1-Y4 one kind independent for being expressed as oxygen, carbon, nitrogen-atoms in general formula (15), general formula (16)；It is expressed as containing there are two the groups of atom to pass through the connected cyclization of 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 of the compound such as general formula (17):
D1-D3 respectively independently indicates substituted or unsubstituted C in general formula (17)6-30It is aryl, 3 yuan to 30 yuan substituted or unsubstituted
Heteroaryl；D1-D3 can be same or different.
8. organic electroluminescence device according to claim 1, it is characterised in that under the material of the electron transfer layer is
One of material shown in column general formula (18), (19), (20), (21) or (22):
General formula (18), general formula (19), general formula (20), general formula (21), E1-E10 is selected as hydrogen, C in general formula (22)1-30Straight chain or branch
The alkyl or alkoxy, substituted or unsubstituted C that alkyl group replaces6-30Aryl, substituted or unsubstituted 3 yuan to 30 yuan heteroaryls
Base；E1-E10 is not hydrogen simultaneously.
9. organic electroluminescence device according to claim 1, it is characterised in that the luminescent device further includes hole note
Enter layer；The hole injection layer material is having structure general formula (23), (24), one of material shown in (25):
In general formula (23), F1-F3 respectively independently indicates substituted or unsubstituted C6-30It is aryl, 3 yuan to 30 yuan substituted or unsubstituted
Heteroaryl；F1-F3 can be same or different；
In general formula (24), general formula (25), G1-G6 expression hydrogen independent, 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, 3 yuan to 30 unit's heteroaryls, G1-G6
It is not simultaneously hydrogen.
10. organic electroluminescence device according to claim 1, it is characterised in that the luminescent device further includes electronics note
Enter layer；The electron injecting layer material is one of 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 organic electroluminescence device described in claim 1, it is characterised in that the dopant material of the luminescent layer and shine
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 general formula (1) is also
The dopant material that can be used as luminescent layer uses.
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 display.
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| GB2464188A (en) * | 2008-10-11 | 2010-04-14 | Fujifilm Imaging Colorants Ltd | Dyes and inks suitable for use in ink jet printing |
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