CN107068880B - A kind of organic electroluminescence device containing diaryl ketone compounds and its application - Google Patents
A kind of organic electroluminescence device containing diaryl ketone compounds and its application Download PDFInfo
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Abstract
The invention discloses a kind of organic electroluminescence device containing diaryl ketone compounds and its applications, the device includes hole transmission layer, luminescent layer, electron transfer layer, the device emitting layer material includes the compound containing diaryl ketone, shown in the structural formula of compound such as general formula (1).Diaryl ketone group 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 diaryl ketone compounds more particularly, to a kind of emitting layer material
Organic electroluminescence 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) high exciton 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, contain the organic of diaryl ketone compounds the present invention provides a kind of
Electroluminescent device and its application.The present invention is based on the diaryl ketone compounds of TADF mechanism to be applied to as emitting layer material
On Organic Light Emitting Diode, have good photoelectric properties, can satisfy OLED device enterprise, especially OLED display panel and
The demand of OLED Illumination Enterprise.
Technical scheme is as follows:
A kind of organic electroluminescence device containing diaryl ketone compounds, the device include hole transmission layer, shine
Layer, electron transfer layer, which includes the compound containing diaryl ketone, the structural formula of compound such as general formula
(1) shown in:
In general formula (1), Ar indicates C6-30Aromatic radical, furyl, thienyl, pyrrole radicals, quinolyl or carbazyl；
In general formula (1), R is indicated using general formula (2):
Wherein, X1For oxygen atom, sulphur atom, selenium atom, C1-10Alkylidene, the aryl of linear or branched alkyl group substitution replace
Alkylidene, one of the amido that replaces of alkyl or aryl；
R1、R2Structure shown in selection hydrogen or general formula (3) independently:
Wherein, a isX2、X3It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Straight chain
Or one of the amido that the alkylidene of branched alkyl substitution, 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.
R in the compound1、R2It is hydrogen, X1For selenium atom, C1-10Alkylidene, the aryl of linear or branched alkyl group substitution
One of the amido that substituted alkylidene, alkyl or aryl replace.
R in the compound1、R2At least one is not hydrogen, X1For oxygen atom, sulphur atom, selenium atom, C1-10Straight chain or
One of the amido that alkylidene, the alkyl or aryl of alkylidene, aryl substitution that branched alkyl replaces replace.
The compound is indicated by general formula (4) or general formula (5):
The concrete structure formula of the compound are as follows:
Any one of.
When the compound that the general formula (1) indicates is as luminescent layer material of main part, the dopant material of luminescent layer uses following
One of material shown in general formula (6), (7), (8) or (9):
In general formula (6), B1-B10 is separately hydrogen, C1-30The alkyl or alcoxyl that linear or branched alkyl group replaces
Base, substituted 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 (7), 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 (8), general formula (9)；
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, shown in structure such as general formula (10):
In general formula (10), D1-D3 respectively independently indicates substituted or unsubstituted C6-30It is aryl, 3 yuan substituted or unsubstituted
To 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 (11), (12), (13), (14) or (15)
Kind:
General formula (11), general formula (12), general formula (13), general formula (14), in general formula (15) E1-E10 be separately hydrogen,
C1-30The alkyl or alkoxy, substituted or unsubstituted C that linear or branched alkyl group replaces6-30It is aryl, 3 yuan substituted or unsubstituted
To 30 unit's heteroaryls；E1-E10 is not hydrogen simultaneously.
The organic electroluminescence device further includes hole injection layer；The material of the hole injection layer is having structure
One of material shown in general formula (16), (17) or (18):
In general formula (16), 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 (17), general formula (18), 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 be lithium, lithium salts or
One of cesium salt；The lithium salts is 8-hydroxyquinoline lithium, lithium fluoride, lithium carbonate or Lithium Azide；The cesium salt be cesium fluoride,
Cesium carbonate or 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.
The dopant material that compound shown in the general formula (1) is also used as luminescent layer uses.
A kind of application of the organic electroluminescence device, 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 diaryl ketone compounds for forming OLED luminescent device of the present invention have the design feature of TADF, are easy real
Existing very small S1-T1 state energy gap is poor, and in excitation, the anti-intersystem crossing of triplet state easy to accomplish to singlet makes original
Originally it cannot 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 diaryl ketone compound as OLED luminescent device, platinum class phosphor material or anthracene class
Fluorescent material in use, device current efficiency, power efficiency and external quantum efficiency are greatly improved；Meanwhile for device
Part life-span upgrading is clearly.Further, on OLED device layer structure matching, after introducing hole and electron injecting layer, make
Transparent anode, metallic cathode and organic material contact interface are more stable, hole, electron injection effect promoting；Hole transmission layer is again
Can lamination be two or more layers, the hole transmission layer of adjacent luminescent layer side can be named as electronic barrier layer (EBL) again, provide
Electronic blocking effect promotes exciton combined efficiency in luminescent layer, and the hole transmission layer of adjacent hole injection layer side then plays
Hole transport and the effect for reducing exciton transfer barrier；Electron transfer layer again can lamination be two or more layers, adjacent luminescent layer one
The electron transfer layer of side can be named as hole blocking layer (HBL) again, provide hole barrier effect, keep exciton in luminescent layer compound
The electron transfer layer of improved efficiency, adjacent electron injecting layer side then plays electron-transport and reduces the work of exciton transfer barrier
With.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 purpose,
And lead to the improvement of organic electroluminescence device, especially voltage, efficiency and the improvement in service life.This especially suitable for red or
The electroluminescent device of green phosphorescent, especially when using 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
The specific synthetic route of the compound is now provided:
The four-hole bottle of 250ml, under the atmosphere for being passed through nitrogen, addition 0.01mol 4,4'- dibromobenzo-phenone,
0.025mol 6,6- dimethyl -6,11- dihydro -13- oxa- -11- 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 are heated to reflux 24 hours, sample contact plate, reaction
Completely；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity 99.2%, yield 67.00%.
Elemental analysis structure (molecular formula C55H40N2O3): theoretical value C, 85.03；H,5.19；N,3.61；O,6.18；Test
Value: C, 84.99；H,5.21；N,3.70；O,6.10.
HPLC-MS: material molecule amount 776.30 surveys molecular weight 776.83.
2 compound 6 of embodiment
The specific synthetic route of the compound is now provided:
The four-hole bottle of 250ml, under the atmosphere for being passed through nitrogen, addition 0.01mol 4,4'- dibromobenzo-phenone,
0.025mol 11,11- dimethyl -4a, 6,11,13a- tetrahydro -13- thia -6- azepines-indoles [1,2-b] anthracene, uncle 0.03mol
Sodium butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene are heated to reflux 24 hours, sampling
Contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity 99.0%, yield
69.00%.
Elemental analysis structure (molecular formula C55H42N2OS2): theoretical value C, 81.45；H,5.22；N,3.45；O,1.97；Test
Value: C, 81.50；H,5.21；N,3.40；O,2.01.
HPLC-MS: material molecule amount 810.27 surveys molecular weight 810.65.
3 compound 11 of embodiment
The specific synthetic route of the compound is now provided:
The four-hole bottle of 250ml, under the atmosphere for being passed through nitrogen, addition 0.01mol 2,2'- dibromobenzo-phenone,
0.025mol 6,6- dimethyl -13- phenyl -11,13- dihydro -6H-11,13- diaza-indoles [1,2-b] 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, take
Sampling point plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity 99.5%, yield
72.00%.
Elemental analysis structure (molecular formula C66H49N4O): theoretical value C, 86.80；H,5.44；N,6.04；O,1.73；Test
Value: C, 86.63；H,5.29；N,6.30；O,1.78.
HPLC-MS: material molecule amount 926.40 surveys molecular weight 926.52.
4 compound 16 of embodiment
The specific synthetic route of the compound is now provided:
The four-hole bottle of 250ml, under the atmosphere for being passed through nitrogen, addition 0.01mol 2,2'- dibromobenzo-phenone,
11,11,13,13- tetramethyl -11,13- dihydro -6H-6- azepine of 0.025mol-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 99.2%, yield 66.00%.
Elemental analysis structure (molecular formula C61H54NO): theoretical value C, 88.16；H,6.55；N,3.37；O,1.93；Test
Value: C, 88.20；H,6.62；N,3.32；O,1.86.
HPLC-MS: material molecule amount 830.42 surveys molecular weight 830.62.
The synthesis of 5 compound 17 of embodiment
The specific synthetic route of the compound is now provided:
0.01mol bis- (the bromo- naphthalene -1- base of 4-)-ketone is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml,
0.025mol6,6- dimethyl -6,11- dihydro -13- oxa- -11- 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 are heated to reflux 24 hours, sample contact plate, reaction
Completely.Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product, purity 99.2%, yield 66.80%.
Elemental analysis structure (molecular formula C63H44N2O3): theoretical value C, 86.28；H,5.06；N,3.19；O,5.47；Test
Value: C, 86.20；H,5.12；N,3.12；O,5.56.
HPLC-MS: material molecule amount 876.34 surveys molecular weight 876.62.
The synthesis of 6 compound 140 of embodiment
The specific synthetic route of the compound is now provided:
0.01mol bis- (4- bromine anthracene -1- base)-ketone is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml,
0.025mol5- phenyl -5,10- dihydro-azophenlyene, 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 99.8%, yield 82.00%.
Elemental analysis structure (molecular formula C65H42N4O): theoretical value C, 87.22；H,4.73；N,6.26；O,1.79；Test
Value: C, 87.20；H,4.72；N,6.32；O,1.76.
HPLC-MS: material molecule amount 894.34 surveys molecular weight 894.38.
The synthesis of 7 compound 143 of embodiment
The specific synthetic route of the compound is now provided:
0.01mol bis--(the bromo- thiophene -2- base of 5-)-ketone is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml,
0.025mol5- phenyl -5,10- dihydro-azophenlyene, 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 99.9%, yield 86.00%.
Elemental analysis structure (molecular formula C45H30N4OS2): theoretical value C, 76.46；H,4.28；N,7.93；O,2.26；S,
9.07；Test value: C, 76.40；H,4.32；N,7.92；O,2.32；S,9.04.
HPLC-MS: material molecule amount 706.19 surveys molecular weight 706.38.
The synthesis of 8 compound 144 of embodiment
The specific synthetic route of the compound is now provided:
(the bromo- 1- phenyl -1H- pyrroles -2- of 5- of 0.01mol bis- is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml
Base)-ketone, 0.025mol5- phenyl -5,10- dihydro-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, sample contact plate, fully reacting.Natural cooling, filtering,
Filtrate revolving, crosses silicagel column, obtains target product, purity 99.9%, yield 86.00%.
Elemental analysis structure (molecular formula C57H40N6O): theoretical value C, 82.99；H,4.89；N,10.19；O,1.94；Test
Value: C, 82.90；H,4.92；N,10.32；O,1.86.
HPLC-MS: material molecule amount 824.33 surveys molecular weight 824.57.
The synthesis of 9 compound 145 of embodiment
The specific synthetic route of the compound is now provided:
0.01mol bis- (the bromo- quinoline -5- base of 8-)-ketone is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml,
0.025mol5- phenyl -5,10- dihydro-azophenlyene, 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 99.9%, yield 84.00%.
Elemental analysis structure (molecular formula C55H36N6O): theoretical value C, 82.89；H,4.55；N,10.55；O,2.01；Test
Value: C, 82.93；H,4.50；N,10.59；O,1.98.
HPLC-MS: material molecule amount 796.30 surveys molecular weight 796.68.
The synthesis of 10 compound 147 of embodiment
The specific synthetic route of the compound is now provided:
The preparation method is the same as that of Example 1 for compound 147, the difference is that raw material 14,14- dimethyl -5,14- dihydro -
7,12- dioxa -5- azepine-pentacene replaces 6,6- dimethyl -6,11- dihydro -13- oxa- -11- azepine-indoles [1,2-b]
Anthracene.
The synthesis of 11 compound 151 of embodiment
The specific synthetic route of the compound is now provided:
The preparation method is the same as that of Example 1 for compound 151, the difference is that raw material 14H-5- oxa- -14- azepine-and five
Benzene replaces 6,6- dimethyl -6,11- dihydro -13- oxa- -11- azepine-indoles [1,2-b] anthracene.
The synthesis of 12 compound 159 of embodiment
The specific synthetic route of the compound is now provided:
The preparation method is the same as that of Example 1 for compound 159, the difference is that raw material 14, phenyl -7 14- dimethyl -5-,
Bis- hydrogen-based -5H-12- oxa- -5,7- diaza of 14--pentacene replaces 6,6- dimethyl -6,11- dihydro -13- oxa- -11- nitrogen
Miscellaneous-indoles [1,2-b] anthracene.
The synthesis of 13 compound 160 of embodiment
The preparation method is the same as that of Example 1 for compound 160, the difference is that raw material A replaces 6,6- dimethyl -6,11- bis-
Hydrogen -13- oxa- -11- azepine-indoles [1,2-b] anthracene.
The synthesis of 14 compound 161 of embodiment
The preparation method is the same as that of Example 1 for compound 161, the difference is that raw material B replaces 6,6- dimethyl -6,11- bis-
Hydrogen -13- oxa- -11- azepine-indoles [1,2-b] anthracene.
The synthesis of 15 compound 163 of embodiment
The preparation method of compound 163 is with embodiment 3, the difference is that raw material C replaces 6,6- dimethyl -13- phenyl -
11,13- dihydro -6H-11,13- diaza-indoles [1,2-b] anthracene.
The synthesis of 16 compound 164 of embodiment
The preparation method is the same as that of Example 1 for compound 164, the difference is that raw material D replaces 6,6- dimethyl -6,11- bis-
Hydrogen -13- oxa- -11- azepine-indoles [1,2-b] anthracene.
The synthesis of 17 compound 166 of embodiment
The preparation method is the same as that of Example 1 for compound 166, the difference is that raw material E replaces 6,6- dimethyl -6,11- bis-
Hydrogen -13- oxa- -11- azepine-indoles [1,2-b] anthracene.
The compounds of this invention can be used as emitting layer material, to the compounds of this invention 1, compound 164 and current material CBP
The measurement of hot property, luminescent spectrum and HOMO, lumo energy is carried out, test result is as shown in table 1.
Table 1
Note: thermal weight loss temperature Td is the temperature of the weightlessness 1% in nitrogen atmosphere, in the TGA-50H heat of Japanese Shimadzu Corporation
It is measured on weight analysis instrument, nitrogen flow 20mL/min；λPLIt is sample solution fluorescence emission wavelengths, 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 of the U.S.
Sub- efficiency test system, reference literature Adv.Mater.1997,9,230-232 method are measured)；Highest occupied molecular rail
Road HOMO energy level and minimum occupied molecular orbital lumo energy are by photoelectron emissions spectrometer (AC-2 type PESA), UV, visible light point
Light photometric determination is tested as atmospheric environment.
By upper table data it is found that the compounds of this invention has suitable HOMO, lumo energy and higher thermal stability,
It is suitable as the material of main part of luminescent layer；Meanwhile the compounds of this invention has suitable luminescent spectrum, higher Φ f, so that answering
The compounds of this invention is used to get a promotion as the OLED device efficiency of dopant material and service life.
Below by way of device embodiments 1-16 and device comparative example 1, the present invention will be described in detail that compound combination is answered in the devices
Use effect.The production work of device embodiments 2-16 of the present invention, the device compared with device embodiments 1 of device comparative example 1
Skill is identical, and uses identical baseplate material and electrode material, the difference is that device surveys stepped construction, collocation
Material and thicknesses of layers are different.Device stack structure is as shown in table 2.Device test data is as 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, hole transmission layer is deposited
Materials'use HT6, film thickness 120nm, this layer is as the hole transmission layer 4 in device architecture；
On hole transmission layer 4, by vacuum evaporation mode, be deposited luminescent layer, emitting layer material use compound 1 as
Material of main part, for GD1 as dopant material, doping mass ratio is 9:1, and luminescent layer film thickness is 40nm, this layer is as device architecture
In luminescent layer 6；
On luminescent layer 6, by vacuum evaporation mode, be deposited electron transfer layer, 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 11 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) (thickness: 40nm, material: compound 16 and GD2 are by weight 88:12 blending structure for/luminescent layer 6
At)/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 (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 17 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) (thickness: 40nm, material: compound 143 of/luminescent layer 6
Constituted with GD3 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 blendings are constituted)/hole transmission layer 4 (thickness: 70nm, material: HT6) (thickness: 40nm, material: compound 144 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 145 and GD4 are constituted by weight 92:8 blending)/hole blocking layer 7 (thickness: 20nm, material: HB1)/electron transfer layer 8
(thickness: 15nm, material: ET2 and EI1, mass ratio 1:1)/Al (thickness: 100nm).
Device embodiments 8
Device stack structure is as shown in device architecture schematic diagram 1: including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6, electron transfer layer 8 and electron transfer 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 147 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 (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 159 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 160 and GD5 are constituted by weight 92:8 blending)/hole blocking layer 7 (thickness: 25nm, material: HB1)/electron transfer layer 8
(thickness: 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 (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 161 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) (thickness: 40nm, material: compound 163 of/luminescent layer 6
Constituted with GD6 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 164 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 166, GH2 and GD2 are constituted by weight 60:30:10 blending)/hole blocking layer
7 (thickness 15nm, material: EB2)/electron transfer layers 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 161, GH4 and GD2 are constituted by weight 60:30:10 blending)/hole blocking layer
7 (thickness 15nm, material: HB1)/electron transfer layers 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 164 is constituted 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 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 60%, and 1 times of life-span upgrading；Device embodiments 2-16 presses this hair
The material adapted and device stack of bright design combine, so that device data is further promoted；As shown in device embodiments 14,15,
When diaryl ketone material of the invention is as hybrid agent material, extraordinary performance data is further obtained；Such as device
Shown in part embodiment 16, diaryl ketone material of the present invention as luminescent layer dopant material in use, equally obtain it is very good
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 diaryl ketone compounds, the device include hole transmission layer, luminescent layer,
Electron transfer layer, it is characterised in that the device emitting layer material includes the compound containing diaryl ketone, the compound structure
Shown in formula such as general formula (1):
In general formula (1), Ar indicates C6-30Aromatic radical, furyl, thienyl, pyrrole radicals, quinolyl or carbazyl；
In general formula (1), R is indicated using general formula (2):
Wherein,
X1For oxygen atom, sulphur atom, selenium atom, C1-10The alkylidene of alkylidene, aryl substitution that linear or branched alkyl group replaces,
One of the amido that alkyl or aryl replaces；
R1、R2Structure shown in selection hydrogen or general formula (3) independently:
Wherein, a isX2、X3It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Straight chain or branch
One of the amido that alkylidene, the alkyl or aryl of alkylidene, aryl substitution that alkyl group replaces 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；And R1、R2
At least one is not hydrogen.
2. organic electroluminescence device according to claim 1, it is characterised in that when a is indicatedAnd and CL4-CL5Key
Or CL‘4-CL’5When key connection, X1And X2Position overlapping, only take X1Or X2；X3Be expressed as oxygen atom, sulphur atom, selenium atom,
C1-10One of the amido that alkylidene, the alkyl or aryl of alkylidene, aryl substitution that linear or branched alkyl group replaces replace；
A passes through CL4-CL5Key or CL‘4-CL’5Key connection is on the intermediate phenyl ring of general formula (2).
3. organic electroluminescence device according to claim 1, it is characterised in that R in the compound1、R2At least one
A is not hydrogen, X1For oxygen atom, sulphur atom, selenium atom, C1-10The Asia of alkylidene, aryl substitution that linear or branched alkyl group replaces
One of the amido that alkyl, alkyl or aryl replace.
4. organic electroluminescence device according to claim 1, it is characterised in that the compound passes through general formula (4) or logical
Formula (5) indicates:
5. organic electroluminescence device according to claim 1, it is characterised in that the concrete structure formula of the compound are as follows:
Any one of.
6. organic electroluminescence device according to claim 1, it is characterised in that the compound that the general formula (1) indicates is made
Dopant material for luminescent layer material of main part, luminescent layer uses one in material shown in general formula (6), (7), (8) or (9)
Kind:
In general formula (6), B1-B10 independently be expressed as hydrogen, C1-30The alkyl or alkoxy of linear or branched alkyl group substitution take
Generation or unsubstituted C6-30Aryl, it is substituted or unsubstituted 3 yuan one of to 30 unit's heteroaryls；B1-B10 is not hydrogen simultaneously；
In general formula (7), 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 (8), general formula (9)；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 structure such as general formula (10):
In general formula (10), D1-D3 respectively independently indicates substituted or unsubstituted C6-30It is aryl, 3 yuan to 30 yuan substituted or unsubstituted
One of 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 (11), (12), (13), (14) or (15):
General formula (11), general formula (12), general formula (13), general formula (14), E1-E10 is separately hydrogen, C in general formula (15)1-30Directly
The alkyl or alkoxy, substituted or unsubstituted C that chain or branched alkyl replace6-30It is aryl, 3 yuan to 30 yuan substituted or unsubstituted
One of heteroaryl；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 material of the hole injection layer is one of material shown in having structure general formula (16), (17) or (18):
In general formula (16), F1-F3 respectively independently indicates substituted or unsubstituted C6-30It is aryl, 3 yuan to 30 yuan substituted or unsubstituted
One of heteroaryl；F1-F3 can be same or different；
In general formula (17), general formula (18), 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 into 30 unit's heteroaryls one
Kind；G1-G6 is not hydrogen simultaneously.
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 or Lithium Azide；The cesium salt is cesium fluoride, cesium carbonate or cesium azide.
11. organic electroluminescence device according to claim 1, it is characterised in that the dopant material and hair of the luminescent layer
The mass ratio of the material of main part of photosphere 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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