CN106220649A - Diaryl ketone-based compound and application thereof in organic electroluminescent device - Google Patents

Diaryl ketone-based compound and application thereof in organic electroluminescent device Download PDF

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CN106220649A
CN106220649A CN201610262088.3A CN201610262088A CN106220649A CN 106220649 A CN106220649 A CN 106220649A CN 201610262088 A CN201610262088 A CN 201610262088A CN 106220649 A CN106220649 A CN 106220649A
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aryl
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diaryl ketone
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CN106220649B (en
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李崇
徐凯
张兆超
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Jiangsu Sunera Technology Co Ltd
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Valiant Co Ltd
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Abstract

The invention discloses a diaryl ketone-based compound and application thereof in an organic electroluminescent device, the compound has the characteristics of difficult intermolecular crystallization and aggregation and good film forming property, and rigid groups in molecules can improve the thermal stability of materials. The compound is used as a luminescent layer material to be applied to an organic electroluminescent device, and the luminescent device using the compound has good photoelectric performance and can better adapt to and meet the application requirements of panel manufacturing enterprises.

Description

A kind of compound based on diaryl ketone and the application on organic electroluminescence device thereof
Technical field
The present invention relates to technical field of semiconductors, especially relate to a kind of compound containing diaryl ketone, and It is as emitting layer material application on Organic Light Emitting Diode.
Background technology
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology can be used to make Make novel display product and illuminating product, be expected to substitute existing liquid crystal display and fluorescent lighting, before application Scape is quite varied.
But, tradition organic fluorescence materials is luminous only with 25% singlet exciton being electrically excited formation, device Internal quantum efficiency relatively low (being up to 25%).External quantum efficiency is generally less than 5%, with the effect of phosphorescent devices Also there is a big difference for rate.Although between phosphor material owing to SO coupling that heavy atom center is strong enhances is Alter more, can effectively utilize singlet exciton and the Triplet exciton being electrically excited formation, make the interior of device Quantum efficiency reaches 100%.But phosphor material exists expensive, stability of material is poor, and device efficiency tumbles The problem such as serious limits its application at OLEDs.Hot activation delayed fluorescence (TADF) material is to have continued The third generation luminous organic material of development after machine fluorescent material and organic phosphorescent material.Such material typically has There is poor (the △ E of little singletstate-tripletST), triplet excitons can be transformed into by anti-intersystem crossing Singlet exciton is luminous.This can make full use of singlet exciton and the triplet excitons being electrically excited lower formation, The internal quantum efficiency of device can reach 100%.Meanwhile, material structure is controlled, stable in properties, low price Without precious metal, having a extensive future of OLEDs field.
Although TADF material can realize the exciton utilization rate of 100% in theory, but there are in fact and ask as follows Topic: T1 and the S1 state of (1) design molecule has a strong CT feature, the least S1-T1 state energy gap, Although high T can be realized by TADF process1→S1State exciton conversion ratio, but also result in low S1 state Radiation transistion speed, consequently it is difficult to have (or realizing) high exciton utilization rate and high fluorescent radiation effect concurrently simultaneously Rate；(2) even if having used doping device to alleviate T exciton concentration quenching effect, most of TADF materials Device efficiency roll-off at higher current densities serious.
For the actual demand of current OLED display Lighting Industry, the development of current OLED material is the most far away Not, lag behind the requirement of panel manufacturing enterprise, as the organic functions material of material enterprise development higher performance Material is particularly important.
Summary of the invention
The problems referred to above existed for prior art, the applicant provides a kind of compound based on diaryl ketone And the application on organic electroluminescence device.The compounds of this invention is based on TADF mechanism, as luminescence Layer material is applied to OLED, and the OLED produced has good photoelectric properties, it is possible to meet face The requirement of plate manufacturing enterprise.
Technical scheme is as follows:
A kind of compound based on diaryl ketone, shown in the structure of this compound such as formula (1):
In formula (1), Ar represents C6-30Aromatic radical, furyl, thienyl, pyrrole radicals, quinolyl or Carbazyl；
In formula (1), R uses formula (2) to represent:
Wherein, X1For oxygen atom, sulphur atom, selenium atom, C1-10The substituted alkylidene of straight or branched alkyl, One in the substituted alkylidene of aryl, the substituted amido of alkyl or aryl；
R1、R2Independently choose structure shown in hydrogen or formula (3):
Wherein, a isX2、X3Be expressed as oxygen atom, sulphur atom, selenium atom, C1-10The substituted alkylidene of straight or branched alkyl, the substituted alkylidene of aryl, the substituted amine of alkyl or aryl One in base；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’5Bonded.
Described compound represents as aAnd and CL4-CL5Key or CL‘4-CL’5Time bonded, X1With X2Location overlap, only take X1Or X2；X3It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Directly In chain or the substituted alkylidene of branched alkyl, the substituted alkylidene of aryl, the substituted amido of alkyl or aryl A kind of.
R in described compound1、R2It is hydrogen, X1For selenium atom, C1-10The substituted Asia of straight or branched alkyl One in the substituted alkylidene of alkyl, aryl, the substituted amido of alkyl or aryl.
R in described compound1、R2At least one is not hydrogen, X1For oxygen atom, sulphur atom, selenium atom, C1-10The substituted alkylidene of straight or branched alkyl, the substituted alkylidene of aryl, the substituted amine of alkyl or aryl One in base.
Described compound is represented by formula (4) or formula (5):
The concrete structure formula of this compound is:
In any one.
A kind of luminescent device containing described compound based on diaryl ketone, described compound is as luminescent layer master Body material, is applied to Organic Light Emitting Diode.
A kind of luminescent device containing described compound based on diaryl ketone, described compound is mixed as luminescent layer Miscellaneous material, is applied to Organic Light Emitting Diode.
A kind of method preparing described compound based on diaryl ketone, reaction equation is:
Weigh two bromo aryl ketones and RH, dissolve with toluene；Add Pd2(dba)3, tri-butyl phosphine, tertiary fourth Sodium alkoxide；Under an inert atmosphere, by the mixed solution of above-mentioned reactant in reaction temperature 95～110 DEG C, react 10～24 Hour, cooling filtering reacting solution, filtrate rotation is steamed, and crosses silicagel column, obtains target product；Described dibromo Mol ratio for aryl ketones Yu RH is 1:2.0～3.0, Pd2(dba)3It is 0.006 with the mol ratio of two bromo aryl ketones ～0.02:1, the mol ratio of tri-butyl phosphine and two bromo aryl ketones is 0.006～0.02:1, sodium tert-butoxide and dibromo Mol ratio for aryl ketones is 1.0～3.0:1.
Useful the having the technical effect that of the present invention
The compounds of this invention is with diaryl ketone as parent nucleus, and both sides connect two aromatic heterocycle groups, it is to avoid molecule Between aggregation, molecule mostly is rigid radical, the film property having had and fluorescence quantum efficiency, permissible Use as luminescent layer dopant material；Described compound structure intramolecular comprises electron donor (donor, D) and electricity The combination of sub-receptor (acceptor, A) can increase Orbital Overlap, improve luminous efficiency, and both sides connect two simultaneously Individual aromatic heterocycle group is to obtain the charge transfer state material that HOMO, LUMO are spatially separating, it is achieved little S1 state and the energy level difference of T1 state, thus under the conditions of thermostimulation, realize reverse intersystem crossing, it is suitable as sending out Photosphere material of main part uses.
Compound of the present invention can be applied to OLED luminescent device as emitting layer material and make, and respectively As luminescent layer material of main part or dopant material, all can obtain good device performance, the electric current effect of device Rate, power efficiency and external quantum efficiency are all greatly improved；Promote the brightest simultaneously for device lifetime Aobvious.
Compound of the present invention has good application effect in OLED luminescent device, has good product Industry prospect.
Accompanying drawing explanation
Fig. 1 is the structural representation that the compounds of this invention is applied to OLED；
Wherein, 1 is transparent substrate layer, and 2 is ito anode layer, and 3 is hole injection layer, and 4 is hole transmission layer, 5 is luminescent layer, and 6 is electron transfer layer, and 7 is electron injecting layer, and 8 is negative electrode reflection electrode layer.
Detailed description of the invention
Below in conjunction with the accompanying drawings and embodiment, the present invention is specifically described.
Embodiment 1 compound 1
The concrete synthetic route of this compound is now provided:
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, addition 0.01mol 4,4'-dibromobenzo-phenone, 0.025mol 6,6-dimethyl-6,11-dihydro-13-oxa--11-azepine-indole [1,2-b] anthracene, the 0.03mol tert-butyl alcohol Sodium, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine, 150ml toluene, it is heated to reflux 24 Hour, sample point plate, reaction is completely；Natural cooling, filters, and filtrate rotation is steamed, and crosses silicagel column, obtains mesh Mark product, purity 99.2%, yield 67.00%.
Elementary 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 is 776.30, surveys molecular weight 776.83.
Embodiment 2 compound 6
The concrete synthetic route of this compound is now provided:
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, addition 0.01mol 4,4'-dibromobenzo-phenone, 0.025mol 11,11-dimethyl-4a, 6,11,13a-tetrahydrochysene-13-thia-6-azepines-indole [1,2-b] anthracene, 0.03mol Sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine, 150ml toluene, heats back Flowing 24 hours, sample point plate, reaction is completely；Natural cooling, filters, and filtrate rotation is steamed, and crosses silicagel column, To target product, purity 99.0%, yield 69.00%.
Elementary 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 is 810.27, surveys molecular weight 810.65.
Embodiment 3 compound 11
The concrete synthetic route of this compound is now provided:
The four-hole bottle of 250ml, under the atmosphere 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-indole [1,2-b] anthracene, 0.03 Mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine, 150ml toluene, add Hot reflux 24 hours, sample point plate, reaction is completely；Natural cooling, filters, and filtrate rotation is steamed, and crosses silicagel column, Obtain target product, purity 99.5%, yield 72.00%.
Elementary analysis structure (molecular formula C66H49N4: theoretical value C, O) 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 is 926.40, surveys molecular weight 926.52.
Embodiment 4 compound 16
The concrete synthetic route of this compound is now provided:
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, addition 0.01mol 2,2'-dibromobenzo-phenone, 0.025mol 11,11,13,13-tetramethyl-11,13-dihydro-6H-6-azepine-indole [1,2-b] anthracene, the tertiary fourth of 0.03mol Sodium alkoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine, 150ml toluene, it is heated to reflux 24 Hour, sample point plate, reaction is completely.Natural cooling, filters, and filtrate rotation is steamed, and crosses silicagel column, obtains mesh Mark product, purity 99.2%, yield 66.00%.
Elementary analysis structure (molecular formula C61H54: theoretical value C, NO) 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 is 830.42, surveys molecular weight 830.62.
The synthesis of embodiment 5 compound 17
The concrete synthetic route of this compound is now provided:
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, adds 0.01mol bis-(4-bromo-naphthalene-1-base)-ketone, 0.025mol6,6-dimethyl-6,11-dihydro-13-oxa--11-azepine-indole [1,2-b] anthracene, the 0.03mol tert-butyl alcohol Sodium, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine, 150ml toluene, it is heated to reflux 24 Hour, sample point plate, reaction is completely.Natural cooling, filters, and filtrate rotation is steamed, and crosses silicagel column, obtains mesh Mark product, purity 99.2%, yield 66.80%.
Elementary 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 is 876.34, surveys molecular weight 876.62.
The synthesis of embodiment 6 compound 140
The concrete synthetic route of this compound is now provided:
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, adds 0.01mol bis-(4-bromine anthracene-1-base)-ketone, 0.025mol5-phenyl-5,10-dihydro-azophenlyene, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine, 150ml toluene, it is heated to reflux 24 hours, sample point plate, reaction is completely.From So cooling, filters, and filtrate rotation is steamed, and crosses silicagel column, obtains target product, purity 99.8%, yield 82.00%.
Elementary analysis structure (molecular formula C65H42N4: theoretical value C, O) 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 is 894.34, surveys molecular weight 894.38.
The synthesis of embodiment 7 compound 143
The concrete synthetic route of this compound is now provided:
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, addition 0.01mol bis--(5-bromo-thiophene-2-base)- Ketone, 0.025mol5-phenyl-5,10-dihydro-azophenlyene, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1×10-4Mol tri-butyl phosphine, 150ml toluene, it is heated to reflux 24 hours, sample point plate, reaction is completely. Natural cooling, filters, and filtrate rotation is steamed, and crosses silicagel column, obtains target product, purity 99.9%, yield 86.00%.
Elementary 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 is 706.19, surveys molecular weight 706.38.
The synthesis of embodiment 8 compound 144
The concrete synthetic route of this compound is now provided:
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, adds 0.01mol bis-(5-bromo-1-phenyl-1H-pyrrole Cough up-2-base)-ketone, 0.025mol5-phenyl-5,10-dihydro-azophenlyene, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine, 150ml toluene, it is heated to reflux 24 hours, sample point plate, Reaction is completely.Natural cooling, filters, and filtrate rotation is steamed, and crosses silicagel column, obtains target product, purity 99.9%, Yield 86.00%.
Elementary analysis structure (molecular formula C57H40N6: theoretical value C, O) 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 is 824.33, surveys molecular weight 824.57.
The synthesis of embodiment 9 compound 145
The concrete synthetic route of this compound is now provided:
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, addition 0.01mol bis-(8-bromo-quinoline-5-base)- Ketone, 0.025mol5-phenyl-5,10-dihydro-azophenlyene, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1×10-4Mol tri-butyl phosphine, 150ml toluene, it is heated to reflux 24 hours, sample point plate, reaction is completely. Natural cooling, filters, and filtrate rotation is steamed, and crosses silicagel column, obtains target product, purity 99.9%, yield 84.00%.
Elementary analysis structure (molecular formula C55H36N6: theoretical value C, O) 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 is 796.30, surveys molecular weight 796.68.
The synthesis of embodiment 10 compound 147
The concrete synthetic route of this compound is now provided:
The preparation method of compound 147 is with embodiment 1, and difference is raw material 14,14-dimethyl-5,14-bis- Hydrogen-7,12-dioxa-5-azepine-Benzo[b replaces 6,6-dimethyl-6,11-dihydro-13-oxa--11-azepine-indole [1,2-b] anthracene.
The synthesis of embodiment 11 compound 151
The concrete synthetic route of this compound is now provided:
The preparation method of compound 151 with embodiment 1, difference be raw material 14H-5-oxa--14-azepine- Benzo[b replaces 6,6-dimethyl-6,11-dihydro-13-oxa--11-azepine-indole [1,2-b] anthracene.
The synthesis of embodiment 12 compound 159
The concrete synthetic route of this compound is now provided:
The preparation method of compound 159 is with embodiment 1, and difference is raw material 14,14-dimethyl-5-phenyl -7,14-two hydrogen-based-5H-12-oxa--5,7-diaza-Benzo[b replaces 6,6-dimethyl-6,11-dihydro-13-oxa- -11-azepine-indole [1,2-b] anthracene.
The synthesis of embodiment 13 compound 160
The preparation method of compound 160 is with embodiment 1, and difference is that raw material A replaces 6,6-dimethyl -6,11-dihydro-13-oxa--11-azepine-indole [1,2-b] anthracene.
The synthesis of embodiment 14 compound 161
The preparation method of compound 161 is with embodiment 1, and difference is raw material B replacement 6,6-dimethyl-6,11- Dihydro-13-oxa--11-azepine-indole [1,2-b] anthracene.
The synthesis of embodiment 15 compound 163
The preparation method of compound 163 is with embodiment 3, and difference is that raw material C replaces 6,6-dimethyl-13- Phenyl-11,13-dihydro-6H-11,13-diaza-indole [1,2-b] anthracene.
The synthesis of embodiment 16 compound 164
The preparation method of compound 164 is with embodiment 1, and difference is that raw material D replaces 6,6-dimethyl -6,11-dihydro-13-oxa--11-azepine-indole [1,2-b] anthracene.
The synthesis of embodiment 17 compound 166
The preparation method of compound 166 is with embodiment 1, and difference is raw material E replacement 6,6-dimethyl-6,11- Dihydro-13-oxa--11-azepine-indole [1,2-b] anthracene.
The compounds of this invention can be as emitting layer material, to the compounds of this invention 1, compound 164 and existing Material C BP carries out the mensuration of hot property, luminescent spectrum and HOMO, lumo energy, test result such as table Shown in 1.
Table 1
Note: thermal weight loss temperature Td is the temperature of weightless 1% in nitrogen atmosphere, enterprising at the TGA-50H thermogravimetric analyzer of Shimadzu Corporation of Japan Row measures, and nitrogen flow is 20mL/min；λPLIt is sample solution fluorescence emission wavelengths, utilizes Japan to open up general health SR-3 spectroradiometer and measure； Φ f is that (utilizing the Maya2000Pro fiber spectrometer of U.S.'s marine optics, the C-701 of Lan Fei company of the U.S. amasss solid powder fluorescence quantum efficiency Bulb separation and the test solid fluorescence quantum efficiency test system of marine optics LLS-LED light source composition, reference literature Adv.Mater.1997,9, The method of 230-232 is measured)；Highest occupied molecular orbital HOMO energy level and minimum occupied molecular orbital lumo energy are to be sent out by photoelectron Penetrate spectrometer (AC-2 type PESA), ultraviolet-uisible spectrophotometer measures, and tests as atmospheric environment.
From upper table data, the compounds of this invention has suitable HOMO, lumo energy and higher Heat stability, be suitable as the material of main part of luminescent layer；Meanwhile, the compounds of this invention has suitable sending out Light spectrum, higher Φ f so that application the compounds of this invention as dopant material OLED efficiency and Life-span gets a promotion.
18-34 and comparative example 1 describe the OLED material of present invention synthesis in detail at device by the following examples The middle application effect as luminescent layer material of main part.19-34 of the present invention, comparative example 1 and embodiment 18 The processing technology comparing described device is identical, and be have employed identical baseplate material and electrode material, The thickness of electrode material also keeps consistent, except that do the material of main part of the luminescent layer 5 in device Conversion.The structure composition of each embodiment obtained device is as shown in table 2.The test result of obtained device is shown in Table 3 Shown in.
Embodiment 18
Ito anode layer 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness 80nm)/luminescent layer 5 (compound 1 and GD19 according to the weight ratio blending of 100:5, Thickness 30nm)/electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm) /Al
Concrete preparation process is as follows:
Ito anode layer 2 (thickness is 150nm) is washed, carry out the most successively neutralizing treatment, pure water, It is dried, then carries out ultraviolet-ozone washing to remove the organic residue on transparent ITO surface.
On the ITO ito anode layer 2 having carried out after above-mentioned washing, utilize vacuum deposition apparatus, be deposited with film Thickness is the molybdenum trioxide MoO of 10nm3Use as hole injection layer 3.And then 80nm thickness it is deposited with TAPC is as hole transmission layer 4.
After above-mentioned hole mobile material evaporation terminates, make the luminescent layer 5 of OLED luminescent device, its structure bag Including the used material compound of OLED luminescent layer 51 as material of main part, GD19, as dopant material, mixes Miscellaneous material doped ratio is 5% weight ratio, and luminescent layer thickness is 30nm.
After above-mentioned luminescent layer 5, continuing vacuum evaporation electron transport layer materials is TPBI.The vacuum of this material Evaporation thickness is 40nm, and this layer is electron transfer layer 6.
On electron transfer layer 6, by vacuum deposition apparatus, make the lithium fluoride (LiF) that thickness is 1nm Layer, this layer is electron injecting layer 7.
On electron injecting layer 7, by vacuum deposition apparatus, make aluminum (Al) layer that thickness is 80nm, This layer is that negative electrode reflection electrode layer 8 uses.
After OLED luminescent device accomplished as described above, with known drive circuit, anode and negative electrode are connected Come, measure the current efficiency of device, luminescent spectrum and the life-span of device.The test result of obtained device is shown in Shown in table 3.
Table 2
Table 3
Device code name Current efficiency Color The LT95 life-span
Embodiment 18 1.6 Green glow 3.6
Embodiment 19 1.9 Green glow 4.3
Embodiment 20 1.7 Green glow 3.7
Embodiment 21 2.2 Green glow 4.2
Embodiment 22 1.7 Green glow 4.1
Embodiment 23 2.2 Green glow 3.7
Embodiment 24 2.1 Green glow 3.9
Embodiment 25 1.6 Green glow 4.2
Embodiment 26 1.9 Green glow 4.0
Embodiment 27 1.6 Green glow 4.1
Embodiment 28 2.0 Green glow 4.8
Embodiment 29 1.8 Green glow 3.2
Embodiment 30 1.4 Green glow 1.9
Embodiment 31 1.8 Green glow 3.5
Embodiment 32 1.9 Green glow 2.7
Embodiment 33 2.0 Green glow 2.4
Embodiment 34 1.7 Green glow 3.3
Comparative example 1 1.0 Green glow 1.0
Illustrate: device detection performance is set to 1.0 using comparative example 1 as reference, comparative example 1 device property indices.The electric current effect of comparative example 1 Rate is 6.5cd/A (@10mA/cm2)；CIE chromaticity coordinates is (0.32,0.61)；Under 5000 brightness, LT95 life time decay is 3.8Hr.
Life-span test system is the OLED life-span tester of owner of the present invention and Shanghai University's joint research.
35-41 and comparative example 2 illustrate that the compound conduct in the devices that the present invention synthesizes is sent out by the following examples The application effect of photosphere dopant material.35-41 of the present invention, comparative example 2 are described compared with embodiment 18 The processing technology of device is identical, and be have employed identical baseplate material and electrode material, electrode material The thickness of material also keeps consistent, except that the dopant material in the luminescent layer 5 in device is different, and doping Concentration becomes 7%.The structure composition of each device is as shown in table 4.The test result of obtained device is shown in Table 5.
Table 4
Table 5
Device code name Current efficiency Color The LT95 life-span
Embodiment 35 1.5 Green glow 4.6
Embodiment 36 1.6 Green glow 3.5
Embodiment 37 1.8 Green glow 2.6
Embodiment 38 1.9 Green glow 5.7
Embodiment 39 1.5 Green glow 3.1
Embodiment 40 1.6 Green glow 5.6
Embodiment 41 2.1 Green glow 4.4
Comparative example 2 1.0 Green glow 1.0
Note: device detection performance is set to 1.0 using comparative example 2 as reference, comparative example 2 device property indices.The current efficiency of comparative example 2 For 9.5cd/A (@10mA/cm2)；CIE chromaticity coordinates is (0.27,0.65)；Under 5000 brightness, LT95 life time decay is 8.2Hr.Life test system System is owner and the OLED life-span tester of Shanghai University's joint development of the present invention.
The result of table 3 can be seen that compound of the present invention can be applied and OLED as luminescent layer material of main part Luminescent device makes, and compared with comparative example 1, either efficiency or life-span are all than known OLED material The life-span that drives of material acquisition bigger change, particularly device obtains bigger lifting.
The result of table 5 can be seen that compound of the present invention can be applied and OLED as luminescent layer dopant material Luminescent device makes, and compared with comparative example 2, either efficiency or life-span are all than known OLED material The life-span that drives of material acquisition bigger change, particularly device obtains bigger lifting.
Should be used for from data above, the compounds of this invention has in OLED luminescent device as emitting layer material There is good application effect, there is good industrialization prospect.
Although disclosing the present invention by embodiment and preferred implementation, it should be appreciated that the invention is not restricted to Disclosed embodiment.On the contrary, it will be understood by those skilled in the art that it is intended to various modification and class As arrange.Therefore, scope of the following claims should consistent with the widest explanation with contain all so Modification and similar arrangement.

Claims (9)

1. a compound based on diaryl ketone, it is characterised in that the structure of this compound such as formula (1) institute Show:
In formula (1), Ar represents C6-30Aromatic radical, furyl, thienyl, pyrrole radicals, quinolyl or Carbazyl；
In formula (1), R uses formula (2) to represent:
Wherein,
X1For oxygen atom, sulphur atom, selenium atom, C1-10The substituted alkylidene of straight or branched alkyl, aryl take One in the substituted amido of the alkylidene in generation, alkyl or aryl；
R1、R2Independently choose structure shown in hydrogen or formula (3):
Wherein, a isX2、X3Be expressed as oxygen atom, sulphur atom, selenium atom, C1-10The substituted alkylidene of straight or branched alkyl, the substituted alkylidene of aryl, the substituted amine of alkyl or aryl One in base；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’5Bonded.
Compound based on diaryl ketone the most according to claim 1, it is characterised in that when a representsAnd and CL4-CL5Key or CL‘4-CL’5Time bonded, X1And X2Location overlap, only take X1 Or X2；X3It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10The substituted alkylene of straight or branched alkyl One in the substituted alkylidene of base, aryl, the substituted amido of alkyl or aryl.
Compound based on diaryl ketone the most according to claim 1, it is characterised in that described compound Middle R1、R2It is hydrogen, X1For selenium atom, C1-10The substituted alkylidene of straight or branched alkyl, aryl replace Alkylidene, one in the substituted amido of alkyl or aryl.
Compound based on diaryl ketone the most according to claim 1, it is characterised in that described compound Middle R1、R2At least one is not hydrogen, X1For oxygen atom, sulphur atom, selenium atom, C1-10Straight or branched One in the substituted alkylidene of alkyl, the substituted alkylidene of aryl, the substituted amido of alkyl or aryl.
Compound based on diaryl ketone the most according to claim 1, it is characterised in that described compound Represented by formula (4) or formula (5):
Compound based on diaryl ketone the most according to claim 1, it is characterised in that this compound Concrete structure formula is:
In any one.
7. the luminescent device containing compound based on diaryl ketone described in any one of claim 1～6, It is characterized in that described compound, as luminescent layer material of main part, is applied to Organic Light Emitting Diode.
8. the luminescent device containing compound based on diaryl ketone described in any one of claim 1～6, It is characterized in that described compound, as luminescent layer dopant material, is applied to Organic Light Emitting Diode.
9. preparing a method for compound based on diaryl ketone described in any one of claim 1-6, it is special Levy and be that reaction equation is:
Weigh two bromo aryl ketones and RH, dissolve with toluene；Add Pd2(dba)3, tri-butyl phosphine, tertiary fourth Sodium alkoxide；Under an inert atmosphere, by the mixed solution of above-mentioned reactant in reaction temperature 95～110 DEG C, react 10～24 Hour, cooling filtering reacting solution, filtrate rotation is steamed, and crosses silicagel column, obtains target product；Described dibromo Mol ratio for aryl ketones Yu RH is 1:2.0～3.0, Pd2(dba)3It is 0.006 with the mol ratio of two bromo aryl ketones ～0.02:1, the mol ratio of tri-butyl phosphine and two bromo aryl ketones is 0.006～0.02:1, sodium tert-butoxide and dibromo Mol ratio for aryl ketones is 1.0～3.0:1.
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