CN106749050A - A kind of hot activation delayed fluorescence OLED material and its application with cyclic diketones as core - Google Patents

A kind of hot activation delayed fluorescence OLED material and its application with cyclic diketones as core Download PDF

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CN106749050A
CN106749050A CN201611159423.3A CN201611159423A CN106749050A CN 106749050 A CN106749050 A CN 106749050A CN 201611159423 A CN201611159423 A CN 201611159423A CN 106749050 A CN106749050 A CN 106749050A
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compound
thickness
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delayed fluorescence
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CN106749050B (en
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高树坤
盛磊
张鑫鑫
胡葆华
陈晓晓
矫志
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Valiant Co Ltd
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Abstract

The invention discloses a kind of hot activation delayed fluorescence OLED material with cyclic diketones as core and its application, belong to organic photoelectrical material technical field.It has the structure shown in formula I：The invention also discloses the application of above-mentioned OLED material.OLED material of the invention is a class with cyclic diketones as notable feature, and the organic micromolecule compound that nitrogen heterocyclic ring is constituted is connected by aromatic group, with suitable molecular entergy level, glass transition temperature higher, and with obvious hot activation delayed fluorescence (TADF) characteristic, can be as TADF materials, the functional layer for preparing organic electroluminescence device, especially luminescent layer, applies in field of organic electroluminescence.

Description

A kind of hot activation delayed fluorescence OLED material and its application with cyclic diketones as core
Technical field
The present invention relates to a kind of hot activation delayed fluorescence OLED material with cyclic diketones as core and its application, belonging to has Machine optoelectronic materials technology.
Background technology
At present, the commodity based on OLED Display Techniques, have been carried out industrialization.Compared with liquid crystal type Display Technique, OLED Display Technique has self-luminous, radiationless, light weight, thickness of thin, wide viewing angle, colour gamut wide, colour stable, fast response time, ring Border adapt to it is strong, many advantages, such as be capable of achieving Flexible Displays, therefore, OLED Display Techniques are obtaining people and are more and more paying close attention to With corresponding Technical investment.
The infrastructure element that OLED shows is OLED, and OLED can be divided into glimmering according to the difference of luminous mechanism Two kinds of optical device and phosphorescent devices.Fluorescence 0LED based on singlet emitter its theoretic interior amount as first generation luminescent material Sub- efficiency only has 25%, it is impossible to further improve its efficiency；Phosphorescence 0LED is referred to as the second generation, and its internal quantum efficiency can reach 100%.Although phosphor material is passed through between being because the strong SO coupling in heavy atom center is enhanced, can effectively utilize The singlet exciton and Triplet exciton to be formed are electrically excited, make the internal quantum efficiency of device up to 100%.But phosphor material is deposited Expensive, stability of material is poor, and service life is short, and device efficiency is tumbled seriously, limits the problems such as blue emitting phosphor is weak Its application in OLED.
2009, the Adachi professors of Kyushu University designed and synthesized a class carbazole Benzonitrile derivatives, then Hot activation delayed fluorescence (TADF) new material based on triplet state-singlet transition is found that, its internal quantum efficiency is approached 100%, this kind of material is the third generation luminous organic material developed after organic fluorescence materials and organic phosphorescent material.Such Material is typically poor (△ EST) with small singlet-triplet, and triplet excitons can be transformed into by anti-intersystem crossing Singlet exciton lights.This can make full use of the singlet exciton and triplet excitons for being electrically excited lower formation, the interior amount of device Sub- efficiency can reach 100%.Meanwhile, material structure is controllable, stable in properties, cheap without precious metal, in OLED necks Domain has a extensive future.But material structure is not clear with the correlation of its photophysical property and device efficiency, limitation The exploitation of efficient delayed fluorescence material, causes the existing TADF material categorys single, device it is less efficient, it is impossible to meet efficient The requirement of Organic Light Emitting Diode.
High efficiency electroluminous process usually requires that electronics is returned during ground state through excitation state radiation transistion, molecule frontier orbit Wave function have and at utmost overlap, overlapping degree is too small to accelerate intersystem crossing process, reduce luminous efficiency.Partly led organic In body material, charge transfer process corresponds to the redox reaction between neutral molecule and corresponding zwitterion, electron donor list Unit and electron acceptor unit have the property of transporting holes and electronics respectively.In recent years, bipolar materials are because of the sky with balance Cave and electronic carrier stream, attract attention in electroluminescent device field, and the life that progressively moving towards the industrialization Produce.
It has been reported that the organic compound with TADF performances, be in structure with obvious electron-donating group with inhale The bipolarity organic micromolecule compound of electron group direct or indirect connection.New TADF materials undoubtedly have wide hair Exhibition prospect.
The content of the invention
An object of the present invention, is to provide a kind of hot activation delayed fluorescence OLED material with cyclic diketones as core. Compound of the invention is applied to Organic Light Emitting Diode with cyclic diketones as core as luminescent layer material of main part, the present invention The device of making has good photoelectric properties, disclosure satisfy that the requirement of panel manufacturing enterprise.
The technical scheme that the present invention solves above-mentioned technical problem is as follows：A kind of hot activation with cyclic diketones as core postpones Fluorescence OLED material, with the structure shown in formula I：
Wherein, L is expressed as hexamethylene, pentamethylene or C1-C10Alkyl-substituted hexamethylene；Ar1Represent C5-C30Aryl； Ar2Selection formula II, formula III, formula IV or structure shown in formula V:
Wherein, X is expressed as oxygen atom, sulphur atom, selenium atom, C1-C10The alkylidene or C of straight chained alkyl substitution1-C10Side chain One kind in the tertiary amine groups of alkyl-substituted alkylidene, the alkylidene of aryl substitution, alkyl-substituted tertiary amine groups or aryl substitution.
On the basis of above-mentioned technical proposal, the present invention can also do following improvement.
Further, the Ar2For:
In appoint It is a kind of.Further, the concrete structure formula of the OLED material is：
In any one.
The second object of the present invention, is to provide a kind of organic electroluminescence device.With common commercialization material of main part CBP Compare, the organic electroluminescence device made using material of the present invention, with more preferable current efficiency and longer device Life-span.
The technical scheme that the present invention solves above-mentioned technical problem is as follows：A kind of organic electroluminescence device, at least one of which work( Ergosphere contains the above-mentioned hot activation delayed fluorescence OLED material with cyclic diketones as core.
On the basis of above-mentioned technical proposal, the present invention can also do following improvement.
Further, the functional layer is luminescent layer.
The beneficial effects of the invention are as follows：
1. the invention provides a class electroluminescent organic material, the material with cyclic diketones as notable feature, Ke Yizuo It is the material of main part with TADF properties, applies in field of organic electroluminescence.
2. the material for being provided using the present invention as functional layer, the organic electroluminescence device of making, with preferable performance, Its feature is：
(1) present invention has synthesized a kind of hot activation delayed fluorescence with cyclic diketones as core by the reaction such as coupling OLED material, and " D- π-A types " organic micromolecule compound that nitrogen heterocyclic ring is constituted, this quasi-molecule tool are connected by aromatic group Have suitable molecular weight (400~900), energy gap (being in 2.5-3.5eV) wider, with small singlet --- triplet state Energy level difference (i.e. △ EST, 0-0.2eV), glass transition temperature Tg (more than 120 DEG C) higher, are suitable as luminous layer main body Material.
(2) molecular structure involved in the present invention, electron donating group is connected with drawing electron group by suitable aryl, The configuration of this distortion, increases the stereoeffect of whole molecule, the biography of the electronics and hole that are more beneficial in luminescent layer Lead with combination, to improve current efficiency it is significant.
(3) light emitting host material is made with such material, adulterate respectively existing luminescent material GD-19, Ir (PPy)3、GD- Used as luminescent layer, prepared organic electroluminescence device has preferable performance to PACTZ, and maximum current efficiency is up to 33cd/ A, the LT95 life-span are 13.0Hr.
3. compared with common commercialization material of main part CBP, the organic electroluminescent made using material of the present invention Device, with more preferable current efficiency and longer device lifetime.
4. compound-material of the present invention has good application effect in OLED luminescent devices, with good product Industry prospect.
Brief description of the drawings
Fig. 1 is to use the device architecture schematic diagram of the compounds of this invention.
Wherein, 1, transparent substrate layer, 2, ito anode layer, 3, hole injection layer, 4, hole transmission layer, 5, luminescent layer, 6, electricity Sub- transport layer, 7, electron injecting layer, 8, negative electrode reflection electrode layer.
Specific embodiment
Principle of the invention and feature are described below in conjunction with specific accompanying drawing, example is served only for explaining this hair It is bright, it is not intended to limit the scope of the present invention.
Embodiment 1：The preparation of compound C1
In 500mL there-necked flasks, 2- (4- bromophenyls) hexamethylene -1,3- diketone (2.67g, 0.01mol), 5- benzene are added Base -5,10- dihydrophenazines (2.58g, 0.01mol), sodium tert-butoxide (2.88g, 0.03mol), dimethylbenzene (300mL), palladium (0.074g), under Xantphos (0.348g), N2 protection, is warming up to backflow, and insulation reaction 12h is down to room temperature, in reaction bulb 150mL deionized waters are added, 5min is stirred, point liquid, 200mL deionized waters washing organic phase 2 times collects organic phase, anhydrous Na2SO4 is dried, filtering, sloughs solvent, and crude product crosses silica gel column chromatography purifying, and eluant, eluent is toluene:Petroleum ether=1:2, changed Compound C1, faint yellow solid 2.85g, yield 64.2%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C30H24N2O2, theoretical value 444.1838, test value 444.1667.Elementary analysis (C30H24N2O2), theoretical value C：81.06, H：5.44, N：6.30, O：7.20, measured value C：81.04, H：5.44, N：6.31, O：7.21.
Embodiment 2：The preparation of compound C4
With embodiment 1, difference is using the 5- benzene in the alternative embodiment 1 of raw material A 1 to the preparation method of compound C4 Base -5,10- dihydrophenazines obtain compound C4, faint yellow solid 3.23g, yield 66.7%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C33H28N2O2, theoretical value 484.2151, test value 484.2331.Elementary analysis (C33H28N2O2), theoretical value C：81.79, H：5.83, N：5.78, O：6.60, measured value C：81.78, H：5.84, N：5.77, O：6.61.
Embodiment 3：The preparation of compound C7
With embodiment 1, difference is using the 5- benzene in the alternative embodiment 1 of raw material A 2 to the preparation method of compound C7 Base -5,10- dihydrophenazines obtain compound C7, faint yellow solid 3.06g, yield 57.3%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C37H27NO3, theoretical value 533.1991, test value 533.1860.Elementary analysis (C37H27NO3), theoretical value C：83.28, H：5.10, N：2.62, O：8.99, measured value C：83.30, H：5.12, N：2.61, O：8.97.
Embodiment 4：The preparation of compound C18
With embodiment 1, difference is using raw material 2- (the bromo- 2' of 4'-, 5'- diformazans to the preparation method of compound C18 Base biphenyl -4- bases) hexamethylene -1,2- (4- bromophenyls) hexamethylene -1 in 3- diketone alternative embodiment 1,3- diketone changed Compound C18, faint yellow solid 3.69g, yield 67.2%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C38H32N2O2, theoretical value 548.2464, test value 548.2410.Elementary analysis (C38H32N2O2), theoretical value C：83.18, H：5.88, N：5.11, O：5.83, measured value C：83.15, H：5.89, N：5.12, O：5.84.
Embodiment 5：The preparation of compound C27
With embodiment 1, difference is using raw material 2- (the bromo- 1- naphthyls of 4-) hexamethylene to the preparation method of compound C27 Alkane -1,2- (4- bromophenyls) hexamethylene -1 in 3- diketone alternative embodiment 1,3- diketone obtains compound C27, pale yellow colored solid Body 3.79g, yield 76.6%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C34H26N2O2, theoretical value 494.1994, test value 494.1871.Elementary analysis (C34H26N2O2), theoretical value C：82.57, H：5.30, N：5.66, O：6.47, measured value C：82.55, H：5.30, N：5.67, O：6.48.
Embodiment 6：The preparation of compound C31
The preparation method of compound C31 with embodiment 1, difference be using raw material 2- (4- bromophenyls) pentamethylene- 2- (4- bromophenyls) hexamethylene -1 in 1,3- diketone alternative embodiment 1,3- diketone obtains compound C31, faint yellow solid 3.09g, yield 71.7%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C29H22N2O2, theoretical value 430.1681, test value 430.1770.Elementary analysis (C29H22N2O2), theoretical value C：80.91, H：5.15, N：6.51, O：7.43, measured value C：80.93, H：5.14, N：6.51, O：7.42.
Embodiment 7：The preparation of compound C37
The preparation method of compound C37 with embodiment 3, difference be using raw material 2- (4- bromophenyls) pentamethylene- 2- (4- bromophenyls) hexamethylene -1 in 1,3- diketone alternative embodiment 1,3- diketone obtains compound C37, faint yellow solid 3.31g, yield 63.8%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C36H25NO3, theoretical value 519.1834, test value 519.1760.Elementary analysis (C36H25NO3), theoretical value C：83.22, H：4.84, N：2.70, O：9.24, measured value C：83.20, H：4.85, N：2.70, O：9.25.
Embodiment 8：The preparation of compound C40
With embodiment 6, difference is using the 5- in the alternative embodiment 1 of raw material A 3 to the preparation method of compound C40 Phenyl -5,10- dihydrophenazines obtain compound C40, faint yellow solid 3.73g, yield 79.2%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C32H25NO3, theoretical value 471.1834, test value 471.1622.Elementary analysis (C32H25NO3), theoretical value C：81.51, H：5.34, N：2.97, O：10.18, measured value C：81.52, H：5.33, N：2.98, O：10.17.
Embodiment 9：The preparation of compound C57
With embodiment 1, difference is using raw material 2- (the bromo- 1- naphthyls of 4-) ring penta to the preparation method of compound C57 Alkane -1,2- (4- bromophenyls) hexamethylene -1 in 3- diketone alternative embodiment 1,3- diketone obtains compound C57, pale yellow colored solid Body 3.29g, yield 68.5%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C33H24N2O2, theoretical value 480.1838, test value 480.1668.Elementary analysis (C33H24N2O2), theoretical value C：82.48, H：5.03, N：5.83, O：6.66, measured value C：82.46, H：5.04, N：5.82, O：6.68.
Embodiment 10：The preparation of compound C67
With embodiment 1, difference is using raw material 2- (4- bromophenyls) -5,5- bis- to the preparation method of compound C67 Hexahydrotoluene -1,2- (4- bromophenyls) hexamethylene -1 in 3- diketone alternative embodiment 1,3- diketone obtains compound C67, Faint yellow solid 3.33g, yield 70.4%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C32H28N2O2, theoretical value 472.2151, test value 472.2251.Elementary analysis (C32H28N2O2), theoretical value C：81.33, H：5.97, N：5.93, O：6.77, measured value C：81.32, H：5.98, N：5.92, O：6.78.
Embodiment 11：The preparation of compound C68
With embodiment 10, difference is using in the alternative embodiment 10 of raw material A 4 to the preparation method of compound C68 5- phenyl -5,10- dihydrophenazines obtain compound C68, faint yellow solid 3.59g, yield 73.7%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C32H26N2O3, theoretical value 486.1943, test value 486.1825.Elementary analysis (C32H26N2O3), theoretical value C：78.99, H：5.39, N：5.76, O：9.86, measured value C：78.98, H：5.37, N：5.78, O：9.87.
Embodiment 12：The preparation of compound C70
With embodiment 10, difference is using in the alternative embodiment 10 of raw material A 1 to the preparation method of compound C70 5- phenyl -5,10- dihydrophenazines obtain compound C70, faint yellow solid 3.74g, yield 72.9%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C35H32N2O2, theoretical value 512.2464, test value 512.2335.Elementary analysis (C35H32N2O2), theoretical value C：82.00, H：6.30, N：5.46, O：6.24, measured value C：82.02, H：6.31, N：5.45, O：6.22.
Embodiment 13：The preparation of compound C72
With embodiment 10, difference is using in the alternative embodiment 10 of raw material A 5 to the preparation method of compound C72 5- phenyl -5,10- dihydrophenazines obtain compound C72, faint yellow solid 3.55g, yield 63.2%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C38H31N3O2, theoretical value 561.2416, test value 561.2337.Elementary analysis (C38H31N3O2), theoretical value C：81.26, H：5.56, N：7.48, O：5.70, measured value C：81.24, H：5.55, N：7.49, O：5.72.
Embodiment 14：The preparation of compound C73
With embodiment 10, difference is using in the alternative embodiment 10 of raw material A 2 to the preparation method of compound C73 5- phenyl -5,10- dihydrophenazines obtain compound C73, faint yellow solid 3.76g, yield 66.9%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C39H31NO3, theoretical value 561.2304, test value 561.2213.Elementary analysis (C39H31NO3), theoretical value C：83.40, H：5.56, N：2.49, O：8.55, measured value C：83.42, H：5.56, N：2.49, O：8.53.
Embodiment 15：The preparation of compound C74
With embodiment 10, difference is using in the alternative embodiment 10 of raw material A 6 to the preparation method of compound C74 5- phenyl -5,10- dihydrophenazines obtain compound C74, faint yellow solid 3.65g, yield 62.1%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C42H37NO2, theoretical value 587.2824, test value 587.2775.Elementary analysis (C42H37NO2), theoretical value C：85.83, H：6.35, N：2.38, O：5.44, measured value C：85.85, H：6.33, N：2.39, O：5.43.
Embodiment 16：The preparation of compound C92
With embodiment 12, difference is to use raw material 2- (the bromo- 1- naphthyls of 4-) -5 to the preparation method of compound C92, 2- (4- bromophenyls) -5,5- dimethyl cyclohexanes -1,3- two in 5- dimethyl cyclohexane -1,3- diketone alternative embodiment 10 Ketone, obtains compound C92, faint yellow solid 4.24g, yield 75.3%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C39H34N2O2, theoretical value 562.2620, test value 562.2517.Elementary analysis (C39H34N2O2), theoretical value C：83.24, H：6.09, N：4.98, O：5.69, measured value C：83.26, H：6.07, N：4.99, O：5.68.
Embodiment 17：The preparation of compound C97
With embodiment 8, difference is to use the A3 in the alternative embodiment 8 of raw material A 7 to the preparation method of compound C97, Obtain compound C97, faint yellow solid 3.54g, yield 71.2%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C35H31NO2, theoretical value 497.2355, test value 497.2357.Elementary analysis (C35H31NO2), theoretical value C, 84.48；H,6.28；N,2.81；O, 6.43, measured value C：84.46, H：6.17, N：2.89, O：6.48.
Embodiment 18：The preparation of compound C98
With embodiment 8, difference is to use the A3 in the alternative embodiment 8 of raw material A 8 to the preparation method of compound C98, Obtain compound C98, faint yellow solid 3.85g, yield 70.5%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C38H30N2O2, theoretical value 546.2307, test value 546.2309.Elementary analysis (C38H30N2O2), theoretical value C, 83.49；H, 5.53；N, 5.12；O, 5.85, measured value C：83.46, H：5.57, N：5.13, O：5.84.
Embodiment 19：The preparation of compound C100
With embodiment 17, difference is using the raw material 2- (bromo- biphenyl -3- of 4'- to the preparation method of compound C100 Base)-pentamethylene -1,2- (4'- bromobenzenes)-pentamethylene -1 in 3- diketone alternative embodiment 17,3- diketone obtains compound C100, faint yellow solid 2.63g, yield 45.9%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C41H35NO2, theoretical value 573.2668, test value 573.2672.Elementary analysis (C41H35NO2), theoretical value C, 85.83；H,6.15；N,2.44；O, 5.58, measured value C：85.76, H：6.15, N：2.38, O：5.71.
Embodiment 20：The preparation of compound C103
With embodiment 18, difference is using the raw material 2- (bromo- biphenyl -3- of 4'- to the preparation method of compound C103 Base)-pentamethylene -1,2- (4'- bromobenzenes)-pentamethylene -1 in 3- diketone alternative embodiment 17,3- diketone obtains compound C103, faint yellow solid 4.10g, yield 66.0%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C44H34N2O2, theoretical value 622.2620, test value 622.2623.Elementary analysis (C44H34N2O2), theoretical value C, 84.86；H,5.50；N,4.50；O, 5.14, measured value C, 84.79； H,5.52；N,4.54；O,5.15.
21-28 and comparative example 1-3 describes the compound conduct in the devices of present invention synthesis in detail by the following examples The application effect of luminescent layer material of main part.Embodiment 22-28 of the present invention, comparative example the 1-3 device compared with embodiment 21 The manufacture craft of part is identical, and employed identical baseplate material and electrode material, and the thickness of electrode material is also protected Hold consistent, except that being converted to the luminescent layer material of main part in device.The structure composition of device is as shown in table 2；Institute The test result for obtaining device is shown in Table 3.
Embodiment 21
Transparent substrate layer 1/ITO anode layers 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm)/hole transmission layer 4 (compound C7 and GD-19 are according to 100 for (TAPC, thickness 80nm)/luminescent layer 5：5 weight is than blending, thickness 30nm)/electronics biography Defeated layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).The molecule of each compound Structural formula is as follows：
Specific preparation process is as follows：
Transparent substrate layer 1 uses transparent material, such as glass；To ito anode layer 2 (thickness is 150nm) wash, i.e., according to It is secondary to carry out carrying out organic residue of the ultraviolet-ozone washing to remove transparent ITO surfaces after neutralizing treatment, pure water, drying again Thing.
On ito anode layer 2 after above-mentioned washing has been carried out, using vacuum deposition apparatus, evaporation thickness is 10nm's Molybdenum trioxide MoO3 is used as hole injection layer 3.And then the TAPC of evaporation 80nm thickness is used as hole transmission layer 4.
After above-mentioned hole mobile material evaporation terminates, the luminescent layer 5 of OLED luminescent devices is made, its structure is sent out including OLED Photosphere 5 uses material compound C7 as material of main part, and used as dopant material, dopant material doping ratio is 5% weight to GD-19 Amount ratio, luminescent layer thickness is 30nm.
After above-mentioned luminescent layer 5, it is TPBI, the vacuum evaporation coating of the material to continue vacuum evaporation electron transport layer materials Thickness is 40nm, and this layer is electron transfer layer 6.
On electron transfer layer 6, by vacuum deposition apparatus, it is lithium fluoride (LiF) layer of 1nm to make thickness, and this layer is Electron injecting layer 7.
On electron injecting layer 7, by vacuum deposition apparatus, it is aluminium (Al) layer of 80nm to make thickness, and this layer is negative electrode Reflection electrode layer 8 is used.
After completing OLED luminescent devices as described above, anode and negative electrode are coupled together with known drive circuit, surveyed The I-E characteristic of the luminous efficiency of metering device, luminescent spectrum and device.
Embodiment 22
Transparent substrate layer 1/ITO anode layers 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm)/hole transmission layer 4 (compound C40 and GD-19 are according to 100 for (TAPC, thickness 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electronics Transport layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
Embodiment 23
Transparent substrate layer 1/ITO anode layers 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm)/hole transmission layer 4 (compound C73 and Ir (PPy) 3 are according to 100 for (TAPC, thickness 80nm)/luminescent layer 5:10 weight is than blending, thickness 30nm)/ Electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
Embodiment 24
Transparent substrate layer 1/ITO anode layers 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm)/hole transmission layer 4 (compound C97 and Ir (PPy) 3 are according to 100 for (TAPC, thickness 80nm)/luminescent layer 5:10 weight is than blending, thickness 30nm)/ Electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
Embodiment 25
Transparent substrate layer 1/ITO anode layers 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm)/hole transmission layer 4 (compound C98 and GD-PACTZ are according to 100 for (TAPC, thickness 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electricity Sub- transport layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
Embodiment 26
Transparent substrate layer 1/ITO anode layers 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm)/hole transmission layer 4 (compound C100 and GD-PACTZ are according to 100 for (TAPC, thickness 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/ Electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
Embodiment 27
Transparent substrate layer 1/ITO anode layers 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm)/hole transmission layer 4 (compound C103, GH-204 and Ir (PPy) 3 are according to 70 for (TAPC, thickness 80nm)/luminescent layer 5:30:10 weight than blending, Thickness 30nm)/electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al)。
Embodiment 28
Transparent substrate layer 1/ITO anode layers 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm)/hole transmission layer 4 (compound C40, GH-204 and GD-PACTZ are according to 70 for (TAPC, thickness 80nm)/luminescent layer 5:30:5 weight is thick than blending Degree 30nm)/electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
Comparative example 1
Transparent substrate layer 1/ITO anode layers 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm)/hole transmission layer 4 (CBP and GD-19 are according to 100 for (TAPC, thickness 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
Comparative example 2
Transparent substrate layer 1/ITO anode layers 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm)/hole transmission layer 4 (CBP and Ir (PPy) 3 are according to 100 for (TAPC, thickness 80nm)/luminescent layer 5:10 weight is than blending, thickness 30nm)/electronics biography Defeated layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
Comparative example 3
Transparent substrate layer 1/ITO anode layers 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm)/hole transmission layer 4 (CBP and GD-PACTZ are according to 100 for (TAPC, thickness 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electric transmission Layer (LiF, thickness the 1nm)/negative electrode layer 8 (Al) of 6 (TPBI, thickness 40nm)/electron injecting layer 7.
The device architecture of made OLED luminescent devices is shown in Table 1, and the test result of made OLED luminescent devices is shown in Table 2.
The device architecture of OLED luminescent devices made by table 1
The test result of OLED luminescent devices made by table 2
Explanation:The current efficiency of comparative example 1 is 6.5cd/A (@10mA/cm2)；Startup voltage is 4.3V (@1cd/m2), LT95 life time decays are 3.8Hr under 5000nit brightness.The current efficiency of comparative example 2 is 24.6cd/A (@10mA/cm2)； LT95 life time decays are 4.3Hr under 5000nit brightness.The current efficiency of comparative example 3 is 25.1cd/A (@10mA/cm2)；Start Voltage is 3.5V (@1cd/m2), and LT95 life time decays are 7.8Hr under 5000nit brightness.
Compound of the present invention can apply luminous with OLED as luminescent layer material of main part from the results shown in Table 2 Element manufacturing, and compared with comparative example 1-3, either efficiency or life-span obtain larger change than known OLED material, The life-span that drives of particularly device obtains larger lifting.
The foregoing is only presently preferred embodiments of the present invention, be not intended to limit the invention, it is all it is of the invention spirit and Within principle, any modification, equivalent substitution and improvements made etc. should be included within the scope of the present invention.

Claims (5)

1. a kind of hot activation delayed fluorescence OLED material with cyclic diketones as core, it is characterised in that with the knot shown in formula I Structure：
Wherein, L is expressed as hexamethylene, pentamethylene or C1-C10Alkyl-substituted hexamethylene；Ar1Represent C5-C30Aryl；Ar2Choosing Modus ponens II, formula III, formula IV or structure shown in formula V:
Wherein, X is expressed as oxygen atom, sulphur atom, selenium atom, C1-C10The alkylidene or C of straight chained alkyl substitution1-C10Branched alkyl One kind in the tertiary amine groups of substituted alkylidene, the alkylidene of aryl substitution, alkyl-substituted tertiary amine groups or aryl substitution.
2. a kind of hot activation delayed fluorescence OLED material with cyclic diketones as core according to claim 1, its feature It is, the Ar2For:
In any one.
3. a kind of hot activation delayed fluorescence OLED material with cyclic diketones as core according to claim 1, its feature It is that the concrete structure formula of the OLED material is：
In any one.
4. a kind of organic electroluminescence device, it is characterised in that at least one functional layer contains any one of claim 1-3 institute The hot activation delayed fluorescence OLED material with cyclic diketones as core stated.
5. a kind of organic electroluminescence device according to claim 4, it is characterised in that the functional layer is luminescent layer.
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