CN107093676A - A kind of organic electroluminescence device containing acridine spiral shell anthracene ketone compounds and its application - Google Patents
A kind of organic electroluminescence device containing acridine spiral shell anthracene ketone compounds and its application Download PDFInfo
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- H10K50/00—Organic light-emitting devices
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- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
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Abstract
The invention discloses a kind of organic electroluminescence device containing acridine spiral shell anthracene ketone compounds, the device includes hole transmission layer, luminescent layer, electron transfer layer, the device emitting layer material includes the compound containing acridine spiral shell anthrone group, shown in the structural formula such as formula (1) of the compound.Acridine spiral shell anthrone group material of the present invention is because with less triplet state and singlet energy difference, therefore it is easily achieved energy transmission between Subjective and Objective material, the energy scattered and disappeared in the form of heat originally is set to be easily obtained utilization, lift luminescent layer radiation transistion efficiency, so as to be easier to the high efficiency for obtaining device, further, when dopant material selection is fluorescent material, it is easier to obtain the luminous radiation of dopant material, so as to be easier to obtain the long-life of material.
Description
Technical field
It is acridine spiral shell anthrone class more particularly, to a kind of emitting layer material the present invention relates to technical field of semiconductors
The organic electroluminescence device of compound and its application.
Background technology
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology both can be for
New display product is manufactured, can be used for making novel illumination product, be expected to substitute existing liquid crystal display
And fluorescent lighting, application prospect is quite varied.
OLED luminescent devices are just as the structure of sandwich, including electrode material film layer, and are clipped in Different electrodes
Organic functional material between film layer, various difference in functionality materials are overlapped mutually common group together according to purposes
Into OLED luminescent devices.As current device, when the two end electrodes to OLED luminescent devices apply voltage,
And by the positive and negative charge in electric field action organic layer functional material film layer, positive and negative charge is further in luminescent layer
In be combined, that is, produce OLED electroluminescent.
Organic Light Emitting Diode (OLED) large-area flat-plate show and illumination in terms of application cause industry
Boundary and the extensive concern of academia.However, traditional organic fluorescence materials can only utilize 25% that is electrically excited and be formed
Singlet exciton lights, and the internal quantum efficiency of device is relatively low (up to 25%).External quantum efficiency is generally less than
5%, also there is a big difference with the efficiency of phosphorescent devices.Although phosphor material due to the spin by force of heavy atom center-
Orbit coupling enhances intersystem crossing, and the singlet exciton and triplet state that effectively can be formed using being electrically excited swash
Son is luminous, makes the internal quantum efficiency of device up to 100%.But there is expensive, stability of material in phosphor material
Poor, the problems such as device efficiency tumbles serious limits its application in OLEDs.Hot activation delayed fluorescence
(TADF) material is the third generation organic light emission material developed after organic fluorescence materials and organic phosphorescent material
Material.Such material typically has small poor (the △ E of singlet-tripletST), triplet excitons can lead to
Cross anti-intersystem crossing be transformed into singlet exciton light.This can make full use of the singlet for being electrically excited lower formation
Exciton and triplet excitons, the internal quantum efficiency of device can reach 100%.Meanwhile, material structure is controllable,
Property is stable, cheap without precious metal, in having a extensive future for OLED fields.
Although TADF materials can realize 100% exciton utilization rate in theory, it there are in fact and ask as follows
Topic:
(1) T1 the and S1 states of design molecule have a strong CT features, very small S1-T1 state energy gaps,
Although high T can be realized by TADF processes1→S1State exciton conversion ratio, but also result in low S1 states
Radiation transistion speed, consequently it is difficult to have (or realizing) high exciton utilization rate and high fluorescent radiation efficiency concurrently simultaneously；
(2) even if mitigating T exciton concentration quenching effects, most of TADF materials using doping device
Device efficiency roll-off is serious at higher current densities.
For the actual demand that current OLED shows Lighting Industry, the development of current OLED material is also much
Not enough, the requirement of panel manufacturing enterprise is lagged behind, the organic functions material of material enterprise development higher performance is used as
Material is particularly important.
The content of the invention
In view of the above-mentioned problems existing in the prior art, acridine spiral shell anthracene ketone compounds are contained the invention provides one kind
Organic electroluminescence device.Acridine spiral shell anthracene ketone compounds of the invention based on TADF mechanism are as luminous
Layer material is applied on Organic Light Emitting Diode, with good photoelectric properties, disclosure satisfy that OLED
The demand of enterprise, particularly OLED display panel and OLED Illumination Enterprises.
Technical scheme is as follows：
A kind of organic electroluminescence device containing acridine spiral shell anthracene ketone compounds, the device includes hole transport
Layer, luminescent layer, electron transfer layer, the device emitting layer material include the chemical combination containing acridine spiral shell anthrone group
Thing, shown in the structural formula such as formula (1) of the compound：
In formula (1), Ar is representedOr-R；Wherein, Ar1Represent phenyl, xenyl, three
Xenyl, naphthyl, anthryl or phenanthryl；
R is represented using formula (2), formula (3), formula (4) or formula (5)：
Wherein, R1、R2Structure shown in selection hydrogen or formula (6) independently：
A isX2、X3Respectively oxygen atom, sulphur atom, selenium atom, C1-10Straight chain
Or branched alkyl substitution alkylidene, aryl substitution alkylidene, alkyl or aryl substitution amido in one
Kind；A and CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL4-CL5Key, CL‘1-CL’2Key, CL‘2-CL’ 3Key, CL‘3-CL’4Key or CL‘4-CL’5Key is connected；
Wherein, R3Represent phenyl, xenyl, terphenyl, naphthyl, anthryl or phenanthryl；X1For oxygen atom,
Sulphur atom, selenium atom, C1-10Alkylidene, alkylidene, the alkane of aryl substitution of straight or branched alkyl substitution
One kind in base or the amido of aryl substitution；X is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Straight chain
Or branched alkyl substitution alkylidene, aryl substitution alkylidene, alkyl or aryl substitution amido in one
Kind.
When a is represented in the compoundAnd and CL4-CL5Key or CL‘4-CL’5When key is connected, X1With
X2Location overlap, only take X1Or X2；X3It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Directly
In chain or the alkylidene of branched alkyl substitution, the alkylidene of aryl substitution, the amido of alkyl or aryl substitution
It is a kind of.
The general structure of the compound is：
Any of.
Ar is in the formula (1)：
In appoint
It is a kind of.
The concrete structure formula of the compound is：
Material shown in the formula (1) is used as luminescent layer material of main part；The dopant material of the luminescent layer makes
With one kind in material shown in general formula (12), (13), (14) or (15)：
In formula (12), B1-B10 selections are hydrogen, C1-30The alkyl or alcoxyl of straight or branched alkyl substitution
Base, substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 3 yuan to 30 unit's heteroaryls；B1-B10
It is asynchronously hydrogen；
In formula (13), the respective independent one kind for being expressed as oxygen, carbon, nitrogen-atoms of Y1-Y6； It is expressed as the group containing two atoms and is connected cyclic by any chemical bond；
Respective independent one kind for being expressed as oxygen, carbon, nitrogen-atoms of Y1-Y4 in formula (14) and formula (15)；It is expressed as the group containing two atoms and is connected cyclic by any chemical bond.
The material of the hole transmission layer is the compound containing triarylamine group, the structural formula of the compound
Shown in formula such as formula (16)：
D1-D3 each independently represents substituted or unsubstituted C in formula (16)6-30Aryl, substitution do not take
3 yuan of generation are to 30 unit's heteroaryls；D1-D3 can be with identical or difference.
The material of the electron transfer layer is shown in general formula (17), (18), (19), (20) or (21)
One kind in material：
E1-E10 is selected in formula (17), formula (18), formula (19), formula (20), formula (21)
It is selected as hydrogen, C1-30The alkyl or alkoxy, substituted or unsubstituted C of straight or branched alkyl substitution6-30Aryl,
Substituted or unsubstituted 3 yuan to 30 unit's heteroaryls；It is hydrogen when E1-E10 is different.
Described organic electroluminescence device, in addition to hole injection layer；The hole injection layer material is following
One kind in general structure (22), (23), material shown in (24)：
In formula (22), F1-F3 each independently represents substituted or unsubstituted C6-30Aryl, substitution do not take
3 yuan of generation are to 30 unit's heteroaryls；F1-F3 can be with identical or difference；
In formula (23), formula (24), G1-G6 each independent expression hydrogen, itrile group, halogen, acid amides
Base, alkoxy, ester group, nitro, C1-30The carbon atom of straight or branched alkyl substitution, substitution or unsubstituted
C6-30Aryl, 3 yuan to 30 unit's heteroaryls, be hydrogen when G1-G6 is different.
Described organic electroluminescence device also includes electron injecting layer；The electron injecting layer material is lithium, lithium
One kind in salt or cesium salt；The lithium salts is 8-hydroxyquinoline lithium, lithium fluoride, lithium carbonate, Lithium Azide；
The cesium salt is cesium fluoride, cesium carbonate, cesium azide.
The mass ratio of the dopant material of the luminescent layer and the material of main part of luminescent layer is 0.005~0.2:1.
The dopant material that compound shown in the formula (1) is also used as luminescent layer is used.
A kind of application of the organic electroluminescence device, for preparing top-illuminating OLED luminescent device.
A kind of application of the organic electroluminescence device, applied to AM-OLED displays.
The present invention is beneficial to be had technical effect that：
Constituting the acridine spiral shell anthracene ketone compounds of OLED luminescent devices of the present invention has TADF structure special
Point, easily realizes that very small S1-T1 state energy gaps are poor, in the case of exciting, easily realizes triplet state to list
The anti-intersystem crossing of line state, makes to light originally, dispersed heat, which is converted into, in the form of heat can produce light
The energy of energy, and be expected to obtain high efficiency.
Based on principles above analysis, OLED luminescent devices of the present invention can both select fluorescent material conduct
Dopant material, can also select phosphor material as dopant material, can also be by TADF materials of the present invention
Material is used directly as dopant material.
The acridine spiral shell anthracene ketone compounds are used as the material of main part collocation iridium of OLED luminescent devices, platinum class phosphorescence
Material or anthracene class fluorescent material are in use, the current efficiency of device, power efficiency and external quantum efficiency are obtained
It is very big to improve；Simultaneously for device lifetime lifting clearly.Further, tied in OLED layer
In structure collocation, introduce after hole and electron injecting layer, make transparent anode, metallic cathode and organic material contact
Interface is more stable, hole, electron injection effect promoting；Hole transmission layer again can lamination be two layers or multilayer,
The hole transmission layer of adjacent luminescent layer side can be named as electronic barrier layer (EBL) again, and there is provided electronic blocking
Effect, lifts exciton combined efficiency in luminescent layer, and the hole transmission layer of adjacent hole injection layer side then rises
To the effect of hole transport and reduction exciton transfer barrier；Electron transfer layer again can lamination be two layers or multilayer,
The electron transfer layer of adjacent luminescent layer side can be named as hole blocking layer (HBL) again, and there is provided hole barrier
Effect, lifts exciton combined efficiency in luminescent layer, and the electron transfer layer of adjacent electron injecting layer side then rises
To the effect of electric transmission and reduction exciton transfer barrier.Each of it should be mentioned, however, that in these layers
It is not necessarily present.
The combined effect of OLED compound of the present invention：So that the driving voltage reduction of device, electric current
Efficiency, power efficiency, external quantum efficiency are further enhanced, and device lifetime lifting effect is obvious.In OLED
There is good application effect, with good industrialization prospect in luminescent device.
Make us against expectation, it has been found that, the compound combination being more particularly described hereinafter realizes this
Purpose, and cause the improvement in the improvement of organic electroluminescence device, particularly voltage, efficiency and life-span.
This is particularly suitable for use in the electroluminescent device of red or green phosphorescent, especially in the device junction using the present invention
When structure and combination of materials, situation is such.
Brief description of the drawings
Fig. 1 is the structural representation of stacked OLED device of the embodiment of the present invention；
In Fig. 1：1 be transparent substrates, 2 be ito anode layer, 3 be hole injection layer (HIL), 4 be hole
Transport layer (HTL), 5 be electronic barrier layer (EBL), 6 be luminescent layer (EML), 7 be hole blocking layer (HBL),
8 it is electron transfer layer (ETL), 9 be electron injecting layer (EIL), 10 is negative electrode reflection electrode layer.
Fig. 2 is the structural formula of critical materials used in device embodiments of the present invention.
Embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
The synthesis of the compound 1 of embodiment 1
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol 2- bromine dibenzofurans,
0.025mol acridine spiral shell anthrones, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-
Tert-butyl group phosphine, 150ml toluene is heated to reflux 24 hours, sample point plate, and reaction is complete, natural cooling,
Filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 99.2%, yield 67.00%.
Elementary analysis structure (molecular formula C38H23NO2)：Theoretical value C, 86.84；H,4.41；N,2.66；O,6.09；
Test value：C,86.91；H,4.44；N,2.70；O,5.95.
HPLC-MS：Material molecule amount is 525.17, surveys molecular weight 525.71.
The synthesis of the compound 2 of embodiment 2
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol 2- (4- bromophenyls)-dibenzo furan
Mutter, 0.025mol acridine spiral shell anthrones, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol
Tri-butyl phosphine, 150ml toluene is heated to reflux 24 hours, sample point plate, and reaction is complete, natural cooling,
Filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 99.0%, yield 69.00%.
Elementary analysis structure (molecular formula C44H27NO2)：Theoretical value C, 87.83；H,4.52；N,2.33；O,5.32；
Test value：C,87.88；H,4.46；N,2.30；O,5.36.
HPLC-MS：Material molecule amount is 601.20, surveys molecular weight 601.76.
The synthesis of the compound 4 of embodiment 3
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol 9- (4- bromophenyls) -9H- carbazoles,
0.025mol acridine spiral shell anthrones, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-
Tert-butyl group phosphine, 150ml toluene is heated to reflux 24 hours, sample point plate, and reaction is complete, natural cooling,
Filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 95.8%, yield 74.00%.
Elementary analysis structure (molecular formula C44H28N2O)：Theoretical value C, 87.97；H,4.70；N,4.66；O,2.66；
Test value：C,87.96；H,4.65；N,4.63；O,2.76.
HPLC-MS：Material molecule amount is 600.22, surveys molecular weight 600.79.
The synthesis of the compound 5 of embodiment 4
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds bromo- 9, the 9- dimethyl -9H- fluorenes of 0.01mol2-,
0.025mol acridine spiral shell anthrones, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-
Tert-butyl group phosphine, 150ml toluene is heated to reflux 24 hours, sample point plate, and reaction is complete, natural cooling,
Filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 95.8%, yield 74.00%.
Elementary analysis structure (molecular formula C41H29NO)：Theoretical value C, 89.26；H,5.30；N,2.54；O,2.90；
Test value：C,89.29；H,5.36；N,2.50；O,2.85.
HPLC-MS：Material molecule amount is 551.22, surveys molecular weight 551.69.
The synthesis of the compound 6 of embodiment 5
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds bromo- 9, the 9- diphenyl -9H- fluorenes of 0.01mol2-,
0.025mol acridine spiral shell anthrones, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-
Tert-butyl group phosphine, 150ml toluene is heated to reflux 24 hours, sample point plate, and reaction is complete, natural cooling,
Filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 95.3%, yield 61.00%.
Elementary analysis structure (molecular formula C51H33NO)：Theoretical value C, 90.64；H,4.92；N,2.07；O,2.37；
Test value：C,90.69；H,4.90；N,2.10；O,2.31.
HPLC-MS：Material molecule amount is 675.26, surveys molecular weight 675.69.
The synthesis of the compound 7 of embodiment 6
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds bromo- 9, the 9- dimethyl -10- benzene of 0.01mol 2-
Base -9,10- dihydro-acridine, 0.025mol acridine spiral shell anthrones, 0.03mol sodium tert-butoxides, 1 × 10-4mol
Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene is heated to reflux 24 hours, sample point plate,
Reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 99.2%,
Yield 62.00%.
Elementary analysis structure (molecular formula C47H34N2O)：Theoretical value C, 87.82；H,5.33；N,4.36；O,2.49；
Test value：C,87.85；H,5.36；N,4.30；O,2.49.
HPLC-MS：Material molecule amount is 642.27, surveys molecular weight 642.96.
The synthesis of the compound 8 of embodiment 7
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol 10- (4- bromophenyls) -9,9- diformazans
Base -9,10- dihydro-acridine, 0.025mol acridine spiral shell anthrones, 0.03mol sodium tert-butoxides, 1 × 10-4mol
Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene is heated to reflux 24 hours, sample point plate,
Reaction is complete, natural cooling, filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 99.1%,
Yield 69.00%.
Elementary analysis structure (molecular formula C47H34N2O)：Theoretical value C, 87.82；H,5.33；N,4.36；O,2.49；
Test value：C,87.96；H,5.43；N,4.34；O,2.27.
HPLC-MS：Material molecule amount is 642.27, surveys molecular weight 642.36.
The synthesis of the compound 9 of embodiment 8
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol10- (4- bromophenyls) -10H- fens
Oxazines, 0.025mol acridine spiral shell anthrones, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol
Tri-butyl phosphine, 150ml toluene is heated to reflux 24 hours, sample point plate, and reaction is complete, natural cooling,
Filtering, filtrate revolving, crosses silicagel column, obtains target product, purity 97.9%, yield 75.00%.
Elementary analysis structure (molecular formula C44H28N2O2)：Theoretical value C, 85.69；H,4.58；N,4.54；O,
5.19；Test value：C,85.75；H,4.55；N,4.56；O,5.14.
HPLC-MS：Material molecule amount is 616.22, surveys molecular weight 616.76.
The synthesis of the compound 10 of embodiment 9
The preparation method be the same as Example 1 of compound 10, difference is raw material 10- (4- bromonaphthalenes base) -10H- fens
Oxazines replaces 2- bromine dibenzofurans.
The synthesis of the compound 12 of embodiment 10
The preparation method be the same as Example 1 of compound 12, difference is raw material 5- (3- bromophenyls) -10- naphthalenes -1-
Base -5,10- dihydros-azophenlyene replaces 2- bromine dibenzofurans.
The synthesis of the compound 13 of embodiment 11
The preparation method be the same as Example 1 of compound 13, difference is the bromo- 10H- of raw material 10- biphenyl -3- bases -3-
Phenoxazine replaces 2- bromine dibenzofurans.
The synthesis of the compound 15 of embodiment 12
The preparation method be the same as Example 1 of compound 15, difference is the bromo- 12- phenyl -12H-6- of raw material 3-
Oxa- -12- azepines-indoles [1,2-b] fluorenes replaces 2- bromine dibenzofurans.
The synthesis of the compound 16 of embodiment 13
The preparation method be the same as Example 1 of compound 16, difference is raw material 3- (4- bromophenyls) -12- phenyl
- 12H-6- oxa-s -12- azepines-indoles [1,2-b] fluorenes replaces 2- bromine dibenzofurans.
The synthesis of the compound 17 of embodiment 14
The preparation method be the same as Example 1 of compound 17, difference is raw material 3- (3- bromophenyls) -12- phenyl
- 12H-6- oxa-s -12- oxa-s-indoles [1,2-b] fluorenes replaces 2- bromine dibenzofurans.
The synthesis of the compound 21 of embodiment 15
The preparation method be the same as Example 1 of compound 21, difference is raw material 13- (3- bromophenyls) -13H-13-
Azepine-indoles [1,2-b] anthracene replaces 2- bromine dibenzofurans.
The synthesis of the compound 22 of embodiment 16
The preparation method be the same as Example 1 of compound 22, difference is raw material 3- bromo- 13- phenyl -13H-6,11-
Dioxa -13- azepines-indoles [1,2-b] anthracene replaces 2- bromine dibenzofurans.
The synthesis of the compound 28 of embodiment 17
The preparation method be the same as Example 1 of compound 28, difference is raw material 6- (4'- bromo biphenyls -4-
Base) -11,11- dimethyl -6,11- dihydro -13- oxa-s -6- azepines-indoles [1,2-b] anthracene replacement 2- bromine dibenzofurans.
The synthesis of the compound 30 of embodiment 18
The preparation method be the same as Example 1 of compound 30, difference is raw material 11- (4- bromophenyls) -13,13-
Dimethyl -11,13- dihydro -6- oxa-s -11- azepines-indoles [1,2-b] anthracene replaces 2- bromine dibenzofurans.
The synthesis of the compound 34 of embodiment 19
The preparation method be the same as Example 1 of compound 34, difference is raw material 5- (4- bromophenyls) -14,14- bis-
Methyl -7- phenyl -7,14- dihydro -5H-12- oxa-s -5,7- diazas-pentacene replaces 2- bromine dibenzofurans.
The synthesis of the compound 36 of embodiment 20
The preparation method be the same as Example 1 of compound 36, difference is raw material 5- (4- bromophenyls) -9,9- diformazans
Base -5H, 9H-5,13b- diaza-naphtho- [3,2,1-de] anthracene replaces 2- bromine dibenzofurans.
The synthesis of the compound 37 of embodiment 21
The preparation method be the same as Example 1 of compound 37, difference is raw material 9- (4- bromophenyls) -9H-5- oxygen
Miscellaneous -9,13b- diazas-naphtho- [3,2,1-de] anthracene replaces 2- bromine dibenzofurans.
The synthesis of the compound 38 of embodiment 22
The preparation method be the same as Example 1 of compound 38, difference is raw material 11- (4- bromophenyls) -6,6- diformazans
Base -6,11- dihydro -13,13 '-dioxa -11,11 '-diaza-indoles [1,2-b] anthracene replaces 2- bromine dibenzo furans
Mutter.
The compounds of this invention can be used as emitting layer material, to the compounds of this invention 12, compound 37,
Current material CBP carries out hot property, luminescent spectrum, fluorescence quantum efficiency and cyclic voltammetric stability respectively
Measure, testing result is as shown in table 1.
Table 1
| Compound | Td(℃) | λPL(nm) | Φf | Cyclic voltammetric stability |
| Compound 12 | 436 | 509 | 86.5 | It is excellent |
| Compound 37 | 479 | 518 | 76.0 | It is excellent |
| Material C BP | 353 | 369 | 26.1 | Difference |
Note：Thermal weight loss temperature Td is the temperature of the weightlessness 1% in nitrogen atmosphere, enterprising in the TGA-50H thermogravimetric analyzers of Japanese Shimadzu Corporation
Row is determined, and nitrogen flow is 20mL/min；λPLIt is sample solution fluorescence emission wavelengths, opening up general health SR-3 spectroradiometers using Japan determines；
Φ f are that solid powder fluorescence quantum efficiency (utilizes the Maya2000Pro fiber spectrometers of U.S.'s marine optics, the C-701 products of Lan Fei companies of the U.S.
The test solid fluorescence quantum efficiency test system of bulb separation and marine optics LLS-LED light sources composition, reference literature Adv.Mater.1997,9,
230-232 method is measured)；Cyclic voltammetric stability is to observe the redox characteristic of material to be identified by cyclic voltammetry；Test
Condition：It is 2 that test sample, which is dissolved in volume ratio,:1 dichloromethane and acetonitrile mixed solvent, concentration 1mg/mL, electrolyte is 0.1M tetrafluoro boric acid
The organic solution of tetrabutylammonium or hexafluorophosphate.Reference electrode is Ag/Ag+ electrodes, is titanium plate to electrode, and working electrode is ITO electricity
Pole, cycle-index is 20 times.
From upper table data, the compounds of this invention has preferable oxidation-reduction stability, and higher is thermally-stabilised
Property, 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 obtained using the compounds of this invention as the OLED efficiency of dopant material and life-span
Lifting.
The compounds of this invention combination is described in detail in device below by way of device embodiments 1-16 and device comparative example 1
Middle application effect.Device embodiments 2-16 of the present invention, device comparative example 1 are compared with device embodiments 1
The manufacture craft of the device is identical, and employed identical baseplate material and electrode material, institute
Unlike, it is different that device surveys stepped construction, collocation material and thicknesses of layers.Device stack structure is such as
Shown in table 2.The performance test results of each device are as shown in table 3.
Device embodiments 1
Device stack structure is as shown in device architecture schematic diagram 1：Include hole transmission layer 4, luminescent layer 6, electricity
Sub- transport layer 8.
Ito anode 2 (thickness of layer：150nm)/hole transmission layer (thickness：120nm, material：HT6)/
Luminescent layer (thickness：40nm, material：Compound 1 and GD1 are by weight 90：10 blendings are constituted)/electricity
Sub- transport layer (thickness：35nm, material：ET2 and EI1, mass ratio 1:1)/Al (thickness：100nm).
Specific preparation process is as follows：
To ito anode layer 2 (thickness is 150nm) washing, neutralizing treatment, pure water, drying are carried out successively
Ultraviolet-ozone washing is carried out afterwards to remove the organic residue on transparent ITO surfaces.
On ito anode layer 2 after the washing, using vacuum deposition apparatus, hole transmission layer 4 is deposited,
Hole transport layer material uses HT6, and thickness is 120nm, and this layer is used as the hole transmission layer 4 in device architecture；
On hole transmission layer 4, by vacuum evaporation mode, luminescent layer 6, emitting layer material useization is deposited
Compound 1 is 9 as dopant material, doping mass ratio as material of main part, GD1：1, luminescent layer thickness
For 40nm, this layer is used as the luminescent layer 6 in device architecture；
On luminescent layer 6, by vacuum evaporation mode, electron transfer layer 8 is deposited, electron transport layer materials make
With ET2 and EI1 mixing and dopings, doping mass ratio is 1:1, thickness is 35nm, and this layer is used as device architecture
In electron transfer layer 8；
On electron transfer layer 8, by vacuum evaporation mode, evaporation cathode aluminium lamination, thickness is 100nm, this
Layer uses for negative electrode reflection electrode layer 10.
Complete after the making of OLED luminescent devices, connected anode and negative electrode as described above with known drive circuit
Pick up the I-E characteristic of next, the luminous efficiency of measurement device, luminescent spectrum and device.
Device embodiments 2
Device stack structure is as shown in device architecture schematic diagram 1：Comprising hole injection layer 3, hole transmission layer 4,
Luminescent layer 6 and electron transfer layer 8.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：10nm, material：HI1)/
(the thickness of hole transmission layer 4：110nm, material：HT2)/(thickness of luminescent layer 6：40nm, material：Change
Compound 4 and GD2 are by weight 88：12 blendings are constituted) 8 (thickness of/electron transfer layer：35nm, material：
ET02 and EI1, mass ratio 1:1)/Al (thickness：100nm).
Device embodiments 3
Device stack structure is as shown in device architecture schematic diagram 1：Comprising hole injection layer 3, hole transmission layer 4,
Luminescent layer 6, electron transfer layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：10nm, material：HI2)/
(the thickness of hole transmission layer 4：110nm, material：HT4)/(thickness of luminescent layer 6：40nm, material：Change
Compound 6 and GD2 are by weight 88：12 blendings are constituted) 8 (thickness of/electron transfer layer：35nm, material：
ET3 and EI1, mass ratio 1:1)/(thickness of electron injecting layer 9：1nm, material：LiN3)/Al (thickness：
100nm)。
Device embodiments 4
Device stack structure is as shown in device architecture schematic diagram 1：Including hole injection layer 3, hole transmission layer 4,
Electronic barrier layer 5, luminescent layer 6 and electron transfer layer 8.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：10nm, material：HI1)/
(the thickness of hole transmission layer 4：90nm, material：HT3)/(thickness of electronic barrier layer 5：20nm, material：
EB2)/(thickness of luminescent layer 6：40nm, material：Compound 8 and GD3 are by weight 89：11 blendings
Constitute) 8 (thickness of/electron transfer layer：35nm, material：ET3 and EI1, mass ratio 1:1)/Al (thickness：
100nm)。
Device embodiments 5
Device stack structure is as shown in device architecture schematic diagram 1：Including hole injection layer 3, hole transmission layer 4,
Luminescent layer 6, electron transfer layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI3 and
HT3, in mass ratio 5:95 blendings are constituted) 4 (thickness of/hole transmission layer：70nm, material：HT3)/hair
(the thickness of photosphere 6：40nm, material：Compound 9 and GD3 are by weight 89：11 blendings are constituted)/electricity
Sub- (the thickness of transport layer 8：35nm, material：ET3)/(thickness of electron injecting layer 9：1nm, material：Li)
/ Al (thickness：100nm).
Device embodiments 6
Device stack structure is as shown in device architecture schematic diagram 1：Including hole injection layer 3, hole transmission layer 4,
Luminescent layer 6, electron transfer layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI4 and
HT3, in mass ratio 5:95 blendings are constituted) 4 (thickness of/hole transmission layer：70nm, material：HT6)/hair
(the thickness of photosphere 6：40nm, material：Compound 12 and GD4 are by weight 92：8 blendings are constituted)/electricity
Sub- (the thickness of transport layer 8：35nm, material：ET4 and EI1, mass ratio 1:1)/electron injecting layer 9 is (thick
Degree：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,
Electronic barrier layer 5, luminescent layer 6, hole blocking layer 7 and electron transfer layer 8.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：10nm, material：HI1)/
(the thickness of hole transmission layer 4：90nm, material：HT6)/(thickness of electronic barrier layer 5：20nm, material：
EB1)/(thickness of luminescent layer 6：40nm, material：Compound 16 and GD4 are by weight 92：8 blendings
Constitute) 7 (thickness of/hole blocking layer：20nm, material：HB1)/(thickness of electron transfer layer 8：15nm,
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,
Electronic barrier layer 5, luminescent layer 6, electron transfer layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI5 and
HT3, in mass ratio 5:95 blendings are constituted) 4 (thickness of/hole transmission layer：50nm, material：HT5)/electricity
Sub- (the thickness of barrier layer 5：20nm, material：EB3)/(thickness of luminescent layer 6：40nm, material：Chemical combination
Thing 21 and GD5 are by weight 92：8 blendings are constituted) 8 (thickness of/electron transfer layer：35nm, material：
ET2 and EI1, mass ratio 1：1)/(thickness of electron injecting layer 9：1nm, material：Cs2CO3)/Al is (thick
Degree：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,
Electronic barrier layer 5, luminescent layer 6, electron transfer layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI6 and
HT4, in mass ratio 5:95 blendings are constituted) 4 (thickness of/hole transmission layer：50nm, material：HT6)/electricity
Sub- (the thickness of barrier layer 5：20nm, material：EB2)/(thickness of luminescent layer 6：40nm, material：Chemical combination
Thing 22 and GD6 are by weight 95：5 blendings are constituted) 8 (thickness of/electron transfer layer：35nm, material：
ET2 and EI1, mass ratio 1：1)/(thickness of electron injecting layer 9：1nm, material：EI1)/Al (thickness：
100nm)。
Device embodiments 10
Device stack structure is as shown in device architecture schematic diagram 1：Including hole injection layer 3, hole transmission layer 4,
Electronic barrier layer 5, luminescent layer 6, hole blocking layer 7, electron transfer layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：10nm, material：HI1)/
(the thickness of hole transmission layer 4：90nm, material：HT3)/(thickness of electronic barrier layer 5：20nm, material：
EB1)/(thickness of luminescent layer 6：40nm, material：Compound 28 and GD5 are by weight 92：8 blendings
Constitute) 8 (thickness of/hole blocking layer：25nm, material：HB1)/electron transfer layer (thickness：10nm,
Material：ET5)/(thickness of electron injecting layer 9：1nm, material：EI1)/Al (thickness：100nm).
Device embodiments 11
Device stack structure is as shown in device architecture schematic diagram 1：Including hole injection layer 3, hole transmission layer 4,
Electronic barrier layer 5, luminescent layer 6, hole blocking layer 7, electron transfer layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI5 and
HT6, in mass ratio 5:95 blendings are constituted) 4 (thickness of/hole transmission layer：50nm, material：HT6)/electricity
Sub- (the thickness of barrier layer 5：20nm, material：EB2)/(thickness of luminescent layer 6：40nm, material：Chemical combination
Thing 34 and GD4 are by weight 92：8 blendings are constituted) 7 (thickness of/hole blocking layer：15nm, material：
HB1)/(thickness of electron transfer layer 8：20nm, material：ET2 and EI1, mass ratio 1：1)/electronics note
Enter (the thickness of layer 9：1nm, 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 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI5 and
HT3, in mass ratio 5:95 blendings are constituted) 4 (thickness of/hole transmission layer：70nm, material：HT6)/hair
(the thickness of photosphere 6：40nm, material：Compound 36 and GD6 are by weight 95：5 blendings are constituted)/empty
(the thickness of cave barrier layer 7：15nm, material：HB1)/(thickness of electron transfer layer 8：20nm, material：
ET6)/(thickness of electron injecting layer 9：1nm, material：CsF)/Al (thickness：100nm).
Device embodiments 13
Device stack structure is as shown in device architecture schematic diagram 1：Including hole injection layer 3, hole transmission layer 4,
Electronic barrier layer 5, luminescent layer 6, electron transfer layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI5 and
HT3, in mass ratio 5:95 blendings are constituted) 4 (thickness of/hole transmission layer：50nm, material：HT6)/electricity
Sub- (the thickness of barrier layer 5：20nm, material：EB2)/(thickness of luminescent layer 6：40nm, material：Chemical combination
Thing 37 and GD2 are by weight 88：12 blendings are constituted) 8 (thickness of/electron transfer layer：35nm, material：
ET2 and EI1, mass ratio 1：1)/(thickness of electron injecting layer 9：1nm, material：CsN3)/Al is (thick
Degree：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,
Electronic barrier layer 5, luminescent layer 6, hole blocking layer 7 and electron transfer layer 8.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI5 and
HT3, in mass ratio 5:95 blendings are constituted) 4 (thickness of/hole transmission layer：50nm, material：HT6)/electricity
Sub- (the thickness of barrier layer 5：20nm, material：EB2)/(thickness of luminescent layer 6：40nm, material：Chemical combination
Thing 38, GH2 and GD2 are by weight 60：30：10 blendings are constituted)/hole blocking layer 7 (thickness 15nm,
Material：EB2)/(thickness of electron transfer layer 8：20nm, material：ET2 and EI1, mass ratio 1：1)/Al
(thickness：100nm).
Device embodiments 15
Device stack structure is as shown in device architecture schematic diagram 1：Including hole injection layer 3, hole transmission layer 4,
Electronic barrier layer 5, luminescent layer 6, hole blocking layer 7 and electron transfer layer 8.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI5 and
HT3, in mass ratio 5:95 blendings are constituted) 4 (thickness of/hole transmission layer：50nm, material：HT6)/electricity
Sub- (the thickness of barrier layer 5：20nm, material：EB2)/(thickness of luminescent layer 6：40nm, material：Chemical combination
Thing 13, GH4 and GD2 are by weight 60：30：10 blendings are constituted)/hole blocking layer 7 (thickness 15nm,
Material：HB1)/(thickness of electron transfer layer 8：20nm, material：ET2 and EI1, mass ratio 1：1)/Al
(thickness：100nm).
Device embodiments 16
Device stack structure is as shown in device architecture schematic diagram 1：Including hole injection layer 3, hole transmission layer 4,
Luminescent layer 6, electron transfer layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole injection layer 3：50nm, material：HI4 and
HT3, in mass ratio 5:95 blendings are constituted) 4 (thickness of/hole transmission layer：70nm, material：HT6)/hair
(the thickness of photosphere 6：40nm, material：GH3 and compound 36 are by weight 92：8 blendings are constituted)/electricity
Sub- (the thickness of transport layer 8：35nm, material：ET4 and EI1, mass ratio 1:1)/electron injecting layer 9 is (thick
Degree：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, electricity
Sub- transport layer 8 and electron injecting layer 9.
Ito anode 2 (thickness of layer：150nm)/(thickness of hole transmission layer 4：120nm, material：HTI)/
(the thickness of luminescent layer 6：40nm, material：GH1 and GD1 is by weight 90：10 blendings are constituted)/electronics
(the thickness of transport layer 8：35nm, material：ET1)/(thickness of electron injecting layer 9：1nm, material：LiF)
/ Al (thickness：100nm).
The OLED is characterized by standard method, from current/voltage/luminous density that the primary emission characteristics of youth is presented
Characteristic line computation, and measurement life-span.It is determined that in 1000cd/m2Electroluminescent spectrum under brightness, calculates CIEx
With y color coordinates, device test data is as shown in table 3.
Table 2
Table 3
Note：Device detection performance is using comparative example 1 as reference, and the device property indices of comparative example 1 are set to 1.0.The current efficiency of comparative example 1
For 32.6cd/A (@1000cd/m2)；Driving voltage is 5.6v (@1000cd/m2)；CIE chromaticity coordinates is (0.34,0.63)；LT95 under 5000 brightness
Life time decay is 3.5Hr.
Table 3 summarizes the OLED in 1000cd/m2Voltage needed for brightness, the current efficiency reached,
And in 5000cd/m2LT95 Decays under brightness.
The comparative device comparative example 1 of device embodiments 1, changes the emitting layer material of the present invention, and by the present invention's
Combination of materials is into after laminated device, device voltage reduction, current efficiency lifting 50%, 3 times of life-span upgrading；
The material adapted and device stack that device embodiments 2-16 is designed by the present invention are combined so that device data enters one
Step lifting；As shown in device embodiments 14,15, acridine spiral shell anthrone class material of the invention is used as hybrid agent
During material, extraordinary performance data is further obtained；As shown in device embodiments 16, a word used for translation of the present invention
Pyridine spiral shell anthrone class material is as luminescent layer dopant material in use, equally obtaining extraordinary performance data.
To sum up, presently preferred embodiments of the present invention is the foregoing is only, is not intended to limit the invention, it is all in this hair
Within bright spirit and principle, any modification, equivalent substitution and improvements made etc. should be included in this hair
Within bright protection domain.
Claims (14)
1. a kind of organic electroluminescence device containing acridine spiral shell anthracene ketone compounds, the device is passed including hole
Defeated layer, luminescent layer, electron transfer layer, it is characterised in that the device emitting layer material includes containing acridine spiral shell anthracene
The compound of ketone groups, shown in the structural formula such as formula (1) of the compound：
In formula (1), Ar represents-Ar1- R or-R；Wherein, Ar1Represent phenyl, xenyl, three
Xenyl, naphthyl, anthryl or phenanthryl；
R is represented using formula (2), formula (3), formula (4) or formula (5)：
Wherein, R1、R2Structure shown in selection hydrogen or formula (6) independently：
A isX2、X3Respectively oxygen atom, sulphur atom, selenium atom, C1-10Straight chain
Or branched alkyl substitution alkylidene, aryl substitution alkylidene, alkyl or aryl substitution amido in one
Kind；A and CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL4-CL5Key, CL‘1-CL’2Key, CL‘2-CL’ 3Key, CL‘3-CL’4Key or CL‘4-CL’5Key is connected；
Wherein, R3Represent phenyl, xenyl, terphenyl, naphthyl, anthryl or phenanthryl；X1For oxygen atom,
Sulphur atom, selenium atom, C1-10Alkylidene, alkylidene, the alkane of aryl substitution of straight or branched alkyl substitution
One kind in base or the amido of aryl substitution；X is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Straight chain
Or branched alkyl substitution alkylidene, aryl substitution alkylidene, alkyl or aryl substitution amido in one
Kind.
2. organic electroluminescence device according to claim 1, it is characterised in that when a is represented
And and CL4-CL5Key or CL‘4-CL’5When key is connected, X1And X2Location overlap, only take X1Or X2；
X3It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Alkylidene, the aryl of straight or branched alkyl substitution
One kind in substituted alkylidene, the amido of alkyl or aryl substitution.
3. organic electroluminescence device according to claim 1, it is characterised in that the knot of the compound
Structure formula is：
4. organic electroluminescence device according to claim 1, it is characterised in that the formula (1)
Middle Ar is：
Any of.
5. organic electroluminescence device according to claim 1, it is characterised in that the tool of the compound
Body structural formula is：
6. organic electroluminescence device according to claim 1, it is characterised in that formula (1) institute
The material shown is used as luminescent layer material of main part；The dopant material of the luminescent layer using general formula (12),
(13), one kind in material shown in (14) or (15)：
In formula (12), B1-B10 selections are hydrogen, C1-30The alkyl or alcoxyl of straight or branched alkyl substitution
Base, substituted or unsubstituted C6-30Aryl, substituted or unsubstituted 3 yuan to 30 unit's heteroaryls；B1-B10
It is asynchronously hydrogen；
In formula (13), the respective independent one kind for being expressed as oxygen, carbon, nitrogen-atoms of Y1-Y6； It is expressed as the group containing two atoms and is connected cyclic by any chemical bond；
Respective independent one kind for being expressed as oxygen, carbon, nitrogen-atoms of Y1-Y4 in formula (14) and formula (15)；It is expressed as the group containing two atoms and is connected cyclic by any chemical bond.
7. organic electroluminescence device according to claim 1, it is characterised in that the hole transmission layer
Material be the compound containing triarylamine group, the structural formula formula such as formula (16) of the compound
It is shown：
D1-D3 each independently represents substituted or unsubstituted C in formula (16)6-30Aryl, substitution do not take
3 yuan of generation are to 30 unit's heteroaryls；D1-D3 can be with identical or difference.
8. organic electroluminescence device according to claim 1, it is characterised in that the electron transfer layer
Material be material shown in general formula (17), (18), (19), (20) or (21) in one kind：
E1-E10 is selected in formula (17), formula (18), formula (19), formula (20), formula (21)
It is selected as hydrogen, C1-30The alkyl or alkoxy, substituted or unsubstituted C of straight or branched alkyl substitution6-30Aryl,
Substituted or unsubstituted 3 yuan to 30 unit's heteroaryls；It is hydrogen when E1-E10 is different.
9. organic electroluminescence device according to claim 1, it is characterised in that the device also includes sky
Cave implanted layer；The hole injection layer material is having structure formula (22), (23), material shown in (24)
In one kind：
In formula (22), F1-F3 each independently represents substituted or unsubstituted C6-30Aryl, substitution do not take
3 yuan of generation are to 30 unit's heteroaryls；F1-F3 can be with identical or difference；
In formula (23), formula (24), G1-G6 each independent expression hydrogen, itrile group, halogen, acid amides
Base, alkoxy, ester group, nitro, C1-30The carbon atom of straight or branched alkyl substitution, substitution or unsubstituted
C6-30Aryl, 3 yuan to 30 unit's heteroaryls, be hydrogen when G1-G6 is different.
10. organic electroluminescence device according to claim 1, it is characterised in that the device also includes electricity
Sub- implanted layer；The electron injecting layer material is one kind in lithium, lithium salts or cesium salt；The lithium salts is 8- hydroxyls
Base quinoline lithium, lithium fluoride, lithium carbonate, Lithium Azide；The cesium salt is cesium fluoride, cesium carbonate, Azide
Caesium.
11. according to the organic electroluminescence device described in claim 1, it is characterised in that the doping of the luminescent layer
The mass ratio of the material of main part of material and luminescent layer is 0.005~0.2:1.
12. organic electroluminescence device according to claim 1, it is characterised in that the formula (1)
The dopant material that shown compound is also used as luminescent layer is used.
13. a kind of application of any one of claim 1~12 organic electroluminescence device, it is characterised in that
The organic 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 electroluminescence device is applied to AM-OLED displays.
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| CN101659638A (en) * | 2008-08-26 | 2010-03-03 | 财团法人工业技术研究院 | Organic compound and organic electroluminescent device containing same |
| CN103650195A (en) * | 2011-07-15 | 2014-03-19 | 国立大学法人九州大学 | Organic electroluminescence element and compound used therein |
| WO2014203840A1 (en) * | 2013-06-21 | 2014-12-24 | 国立大学法人九州大学 | Red light-emitting material, organic light-emitting element, and compound |
| CN105340101A (en) * | 2013-07-03 | 2016-02-17 | 国立大学法人九州大学 | Light-emitting material, long-persistent phosphor, organic light-emitting element and compound |
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| CN101659638A (en) * | 2008-08-26 | 2010-03-03 | 财团法人工业技术研究院 | Organic compound and organic electroluminescent device containing same |
| CN103650195A (en) * | 2011-07-15 | 2014-03-19 | 国立大学法人九州大学 | Organic electroluminescence element and compound used therein |
| WO2014203840A1 (en) * | 2013-06-21 | 2014-12-24 | 国立大学法人九州大学 | Red light-emitting material, organic light-emitting element, and compound |
| CN105340101A (en) * | 2013-07-03 | 2016-02-17 | 国立大学法人九州大学 | Light-emitting material, long-persistent phosphor, organic light-emitting element and compound |
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| CN107056758A (en) * | 2016-04-25 | 2017-08-18 | 中节能万润股份有限公司 | A kind of compound as core using acridine spiral shell anthrone and its application on organic electroluminescence device |
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