CN107056763A - A kind of electroluminescent organic material and its application using xanthene as core - Google Patents

A kind of electroluminescent organic material and its application using xanthene as core Download PDF

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CN107056763A
CN107056763A CN201610260576.0A CN201610260576A CN107056763A CN 107056763 A CN107056763 A CN 107056763A CN 201610260576 A CN201610260576 A CN 201610260576A CN 107056763 A CN107056763 A CN 107056763A
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compound
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electroluminescent
formula
layer
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张鑫鑫
陈阳
王正
郭晓光
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Valiant Co Ltd
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Valiant Co Ltd
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Abstract

The invention discloses a kind of compound using xanthene as core, and its application of such compound in organic electroluminescence device, such compound has appropriate molecular entergy level, excellent heat endurance and thin film stability, the functional layer of organic electroluminescence device is suitable as, is applied in field of organic electroluminescence.

Description

A kind of electroluminescent organic material and its application using xanthene as core
Technical field
The present invention relates to organic photoelectrical material technical field, more particularly, to bone centered on a kind of xanthene structure The electroluminescent organic material of frame and its application in OLED fields.
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 positive and negative charge in electric field action organic layer functional material film layer, positive and negative charge is further in luminescent layer It is compound, that is, produce OLED electroluminescent.
Currently, OLED Display Techniques are in smart mobile phone, and the field such as tablet personal computer is applied, further It will also extend, still, be compared with actual products application requirement, OLED to the large scale such as TV application field The luminous efficiency of device, the performance such as service life also needs to further lifting.
Proposing high performance research for OLED luminescent devices includes：The driving voltage of device is reduced, device is improved Luminous efficiency, improve service life etc. of device.For the continuous lifting of the performance of realizing OLED, The innovation from OLED structure and manufacture craft is not only needed, with greater need for oled light sulfate ferroelectric functional material not Disconnected research and innovation, formulate out higher performance OLED functional material.
Oled light sulfate ferroelectric functional material applied to OLED can be divided into two major classes, i.e. electric charge from purposes Transmission material and luminescent material are injected, further, transmission material can be also injected charge into and be divided into electron injection biography Defeated material, electron-blocking materials, hole injection transmission material and hole barrier materials, can also be by luminous material Material is divided into main body luminescent material and dopant material.
In order to make high performance OLED luminescent devices, it is desirable to which various organic functional materials possess good photoelectricity Characteristic, for example, is used as charge transport materials, it is desirable to which, with good carrier mobility, high-vitrification turns Change temperature etc., require that material has good bipolarity as the material of main part of luminescent layer, appropriate HOMO/LUMO energy ranks etc..
Constituting the oled light sulfate ferroelectric functional material film layer of OLED at least includes in more than two layers structure, industry The OLED structure of application, then including hole injection layer, hole transmission layer, electronic barrier layer, luminous A variety of film layers such as layer, hole blocking layer, electron transfer layer, electron injecting layer, that is to say, that applied to OLED The photoelectric functional material of device comprises at least hole-injecting material, hole mobile material, luminescent material, electronics Injection material etc., material type and collocation form have rich and multifarious feature.In addition, for not For isostructural OLED collocation, used photoelectric functional material has stronger selectivity, phase Performance of the same material in different structure device, it is also possible to completely totally different.
Therefore, for the difference in functionality film of the industry application requirement of current OLED, and OLED Layer, the photoelectric characteristic demand of device, it is necessary to which selection is more suitable for, with high performance OLED functional materials or Combination of materials, could realize the overall characteristic of high efficiency, long-life and the low-voltage of device.With regard to current OLED For the actual demand for showing Lighting Industry, the development of current OLED material is also far from enough, lags behind face The requirement of plate manufacturing enterprise, the exploitation as the organic functional material of material enterprise development higher performance seems outstanding To be important.
The content of the invention
In view of the above-mentioned problems existing in the prior art, the applicant provides a kind of using xanthene as the organic of core Electroluminescent material and its application.Luminescent material of the present invention contains xanthene structure, with higher vitrifying Temperature and molecule heat endurance, suitable HOMO and lumo energy, higher Eg pass through device architecture Optimization, can effectively lift the photoelectric properties of OLED and the life-span of OLED.
Technical scheme is as follows：
A kind of electroluminescent organic material using xanthene as core, the structural formula such as formula (1) of the luminescent material It is shown：
In formula (1), Ar1、Ar2It is each independent to be expressed as phenyl, xenyl or naphthyl；Ar1、Ar2 Can be with identical or different；R1、R2Respectively hydrogen or the structure represented using formula (2), and R1、R2No It is simultaneously hydrogen；
In formula (2), X1For oxygen atom, sulphur atom, selenium atom, C1-10Straight or branched alkyl substitution One kind in alkylidene, the alkylidene of aryl substitution, the amido of alkyl or aryl substitution；R3、R4It is only respectively On the spot choose structure shown in hydrogen or formula (3)；
In formula (3), a is selected fromX2、X3Independently for oxygen atom, sulphur Atom, selenium atom, C1-10Alkylidene, alkylidene, the alkyl of aryl substitution of straight or branched alkyl substitution Or one kind in the amido of aryl substitution；A and CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL4-CL5 Key, CL‘1-CL’2Key, CL‘2-CL’3Key, CL‘3-CL’4Key or CL‘4-CL’5Key is connected.
Further, it is described when a is representedAnd and CL4-CL5Key or CL‘4-CL’5When key is connected, X1 And X2Location overlap, only take X1Or X2；X3For 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.
Further, R in the formula (1)1、R2Respectively：
Any of；R1It is also denoted as hydrogen.
Further, the concrete structure formula of the luminescent material is：
Any of.
A kind of method for preparing the electroluminescent organic material, the synthetic route of this method is：
R1During for hydrogen, synthetic route is as follows：
R1When being not hydrogen, synthetic route is as follows：
Methods described is using Br-Ar2-Br as raw material, by grignard reaction, RMgBr is made, then with xanthenes Reactive ketone, generates the tertiary alcohol, the tertiary alcohol and H-Ar1-R1Or H-Ar1-I passes through friedel-crafts reaction, obtainedization Compound A or compound B, compound A or compound B with The luminescent material is made by C-N couplings.
A kind of organic electroluminescence device for including the electroluminescent organic material, the organic electroluminescent electricity Material is as emitting layer material, for organic electroluminescent LED.
A kind of organic electroluminescence device for including the electroluminescent organic material, the organic electroluminescent electricity Material is as hole injection layer, hole transmission layer and electronic blocking layer material, for the pole of organic electroluminescent two Pipe.
The present invention is beneficial to be had technical effect that：
Electroluminescent organic material of the present invention, which has, intermolecular to be difficult to crystallize, is difficult to assemble, with good filming The characteristics of, the rigid radical in molecule can improve the heat endurance of material, while HOMO and LUMO Energy level electron cloud is efficiently separated, and less S1-T1 states energy gap can be achieved, and the xanthene structure of aryl substitution is taken Exciton utilization rate and high fluorescent radiation efficiency can be effectively improved with the side chain in the scope of the invention, OLED is used as The emitting layer material of luminescent device is in use, the current efficiency of device, power efficiency and external quantum efficiency are obtained Improve to very big；Simultaneously for device lifetime lifting clearly.
The electronics and hole distribution of luminescent material of the present invention are more balanced, and are injected as the hole in OLED When layer, hole transmission layer and electronic barrier layer materials'use, the efficiency roll-off drop under the high current density of device Low, the reduction of device drive voltage, the current efficiency of device and life-span improve.
Luminescent material of the present invention has good application effect in OLED luminescent devices, with good industry Change prospect.
Brief description of the drawings
Fig. 1 is the structural representation of the OLED of the materials application cited by the present invention；
Wherein, 1 is transparent substrate layer, and 2 be ito anode layer, and 3 be hole injection layer, 4 be hole transport/ Electronic barrier layer, 5 be luminescent layer, and 6 be hole barrier/electron transfer layer, and 7 be electron injecting layer, and 8 be the moon Pole reflection electrode layer.
Embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
The synthesis of the compound 1 of embodiment 1：
Synthetic route：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 11.8g to Isosorbide-5-Nitrae-dibromobenzene (0.05mol) With 1.44gMg powder (0.06mol), 60ml tetrahydrofurans are heated to reflux 4 hours, and reaction is complete, generation Grignard reagent；
9.8g Oxoxanthones (0.05mol) are dissolved in 50ml tetrahydrofurans, and above-mentioned grignard reagent is added dropwise, and 60 DEG C anti- Answer 24 hours, generate a large amount of white precipitates, be eventually adding saturation NHCl4Form salt is converted into alcohol；Reaction After finishing, revolving, petroleum ether: the purifying of dichloromethane mixed solvent (3: 2) silicagel column are dried in ether extraction, Obtain the compound C of yellowish (yield is 90%)；The compound, molecule are recognized using DEI-MS Formula C19H13BrO, detected value [M+1]+=353.85, calculated value 353.21；
14.1g compounds C (0.04mol) ought be measured by 1: 2 and 6.2g benzene (0.08mol) is dissolved in 100ml In dichloromethane, 10ml boron trifluoride etherates are added dropwise at ambient temperature, react 30 minutes, Add 20ml ethanol and 20ml water quenchings to go out reaction, extracted with dichloromethane (20ml*3), dry and rotate, Petroleum ether silicagel column is purified, with ethanol: recrystallize with dichloromethane obtains compound D (yield is 85%)；Use DEI-MS recognizes the compound, molecular formula C25H17BrO, detected value [M+1]+=413.88, calculated value 413.31；
In 250ml there-necked flask, lead under nitrogen protection, add 8.3g (0.02mol) compounds D, 5.5g (0.03mol) 10H- phenoxazines, 2.88g (0.03mol) sodium tert-butoxide, 0.30g pd2(dba)3, 0.20g Tri-tert phosphorus, 200ml toluene is heated to reflux 24 hours, sample point plate, and reaction is complete；Natural cooling, Filtering, filtrate revolving, column chromatography obtains target product, HPLC purity 98.9%, yield 72.57%；
The compound, molecular formula C are recognized using DEI-MS37H25NO2, detected value [M+1]+=516.11, Calculated value 515.60.
The synthesis of the compound 3 of embodiment 2：
Synthetic route：
14.1g compounds C (0.04mol) ought be measured by 1: 2 and 16.3g iodobenzenes (0.08mol) are dissolved in 100ml In dichloromethane, 10ml boron trifluoride etherates are added dropwise at ambient temperature, react 30 minutes, Add 20ml ethanol and 20ml water quenchings to go out reaction, extracted with dichloromethane (20ml*3), dry and rotate, Petroleum ether silicagel column is purified, with ethanol: recrystallize with dichloromethane obtains compound E (yield is 82%)；Use DEI-MS recognizes the compound, molecular formula C25H16BrIO, detected value [M+1]+=538.82, calculated value 537.94；
In 250ml there-necked flask, lead under nitrogen protection, add 10.8g (0.02mol) compounds E, 6.3g (0.03mol) 9,9- dimethyl -9,10- acridans, 5.5g (0.04mol) potassium carbonate, 0.4g cuprous iodides, 200ml dioxane, is heated to reflux 24 hours, sample point plate, and reaction is complete；Natural cooling, filtering, Filtrate rotates, and column chromatography obtains compound F (yield 64%)；The compound is recognized using DEI-MS, point Minor C40H30BrNO, detected value [M+1]+=620.05, calculated value 619.15.
In 250ml there-necked flask, lead under nitrogen protection, add 6.2g (0.01mol) compounds F, 3.15g (0.015mol) 9,9- dimethyl -9,10- acridans, 1.44g (0.015mol) sodium tert-butoxide, 0.15g pd2(dba)3, 0.10g tri-tert phosphorus, 150ml toluene is heated to reflux 24 hours, sample point plate, reacts Completely；Natural cooling, filtering, filtrate revolving, column chromatography obtains target product, HPLC purity 99.1%, Yield 69.3%；
The compound, molecular formula C are recognized using DEI-MS55H44N2O, detected value [M+1]+=749.38, Calculated value 748.35.
The synthesis of the compound 8 of embodiment 3：
Prepared by the synthetic method of compound 1 in embodiment 1, difference is to replace 10H- with compound G Phenoxazine；
The compound, molecular formula C are recognized using DEI-MS49H32N2O2, detected value [M+1]+=681.23, Calculated value 680.25.
The synthesis of the compound 10 of embodiment 4：
Prepared by the synthetic method of compound 1 in embodiment 1, difference is to replace 10H- with compound H Phenoxazine；
The compound, molecular formula C are recognized using DEI-MS52H38N2O, detected value [M+1]+=707.35, Calculated value 706.30.
The synthesis of the compound 13 of embodiment 5：
Prepared by the synthetic method of compound 1 in embodiment 1, difference is to replace 10H- with compound I Phenoxazine；
The compound, molecular formula C are recognized using DEI-MS46H33NO2, detected value [M+1]+=632.25, Calculated value 631.25.
The synthesis of the compound 25 of embodiment 6：
Prepared by the synthetic method of compound 1 in embodiment 1, difference is to replace 10H- with compound J Phenoxazine；
The compound, molecular formula C are recognized using DEI-MS46H34N2O, detected value [M+1]+=631.27, Calculated value 630.27.
The synthesis of the compound 27 of embodiment 7：
Prepared by the synthetic method of compound 1 in embodiment 1, difference is to replace 10H- with compound K Phenoxazine；
The compound, molecular formula C are recognized using DEI-MS43H28N2O2, detected value [M+1]+=605.13, Calculated value 604.22.
The synthesis of the compound 34 of embodiment 8：
Prepared by the synthetic method of compound 1 in embodiment 1, difference is to replace 10H- with compound K Phenoxazine；
The compound, molecular formula C are recognized using DEI-MS46H33NO3, detected value [M+1]+=648.15, Calculated value 647.25.
The synthesis of the compound 36 of embodiment 9：
Prepared by the synthetic method of compound 1 in embodiment 1, difference is to replace 10H- with compound M Phenoxazine；
The compound, molecular formula C are recognized using DEI-MS64H45N3O, detected value [M+1]+=872.11, Calculated value 871.36.
The synthesis of the compound 46 of embodiment 10：
Prepared by the synthetic method of compound 1 in embodiment 1, difference is to replace 10H- with compound N Phenoxazine；
The compound, molecular formula C are recognized using DEI-MS52H35NO3, detected value [M+1]+=722.31, Calculated value 721.26.
The synthesis of the compound 46 of embodiment 11：
Prepared by the synthetic method of compound 3 in embodiment 2, difference is to use in the 4th step chemically reacts 10H- phenoxazines replace 9,9- dimethyl -9,10- acridans；
The compound, molecular formula C are recognized using DEI-MS52H38N2O2, detected value [M+1]+=723.24, Calculated value 722.29.
The compounds of this invention can be used as emitting layer material, to the compounds of this invention 1, compound 37, be changed Compound 47, current material CBP, NPB carry out hot property, luminescent spectrum and HOMO, LUMO respectively Energy level is tested, and test result is as shown in table 1.
Table 1
Note：Glass transition temperature Tg is determined by differential scanning calorimetry (DSC, German Nai Chi companies DSC204F1 differential scanning calorimeters), is risen Warm 10 DEG C/min of speed；Thermal weight loss temperature Td is the temperature of the weightlessness 1% in nitrogen atmosphere, in the TGA-50H thermogravimetrics point of Japanese Shimadzu Corporation It is measured in analyzer, nitrogen flow is 20mL/min；λPLIt is sample solution fluorescence emission wavelengths, general health SR-3 spectroradios is opened up using Japan Degree meter is determined；Highest occupied molecular orbital HOMO energy levels and minimum occupied molecular orbital lumo energy are by photoelectron emissions spectrometer (AC-2 Type PESA) and ultraviolet specrophotometer (UV) measuring and calculation gained, test as atmospheric environment.
From upper table data, the compounds of this invention has suitable HOMO, lumo energy and suitable Luminescent spectrum, the hole class material and the luminescent material of inclined cavity type being suitable as in OLED； Oxa anthracene compound of the present invention has higher heat endurance so that made containing the compounds of this invention OLED life-span upgrading.
Hereinafter, the OLED material that the present invention is synthesized is described in detail by device embodiments 1~11 and comparative example 1 In the devices as the application effect of emitting layer material.Device embodiments 2~11 of the present invention, comparative example 1 The manufacture craft of the device is identical compared with device embodiments 1, and employed identical substrate Material and electrode material, the thickness of electrode material are also consistent, except that to the luminescent layer 5 in device Material of main part convert.
Device embodiments 1
A kind of electroluminescent device, its preparation process includes：
A) the ito anode layer 2 on cleaning transparent substrate layer 1, respectively with deionized water, acetone, EtOH Sonicate Clean each 15 minutes, then handled 2 minutes in plasma cleaner；
B) on ito anode layer 2, hole transport layer material HAT-CN is deposited by vacuum evaporation mode, Thickness is 10nm, and this layer is used as hole injection layer 3；
C) on hole injection layer 3, hole mobile material NPB is deposited by vacuum evaporation mode, thickness is 80nm, the layer is hole transmission layer/electronic barrier layer 4；
D) luminescent layer 5 is deposited on hole transport/electronic barrier layer 4, using CBP as being used as main body material Material, the compounds of this invention 37 is as dopant material, and material doped mass ratio is 10%, and thickness is 30nm；
E) on luminescent layer 5, electron transport material TPBI is deposited by vacuum evaporation mode, thickness is 40nm, This layer of organic material is used as hole barrier/electron transfer layer 6；
F) on hole barrier/electron transfer layer 6, vacuum evaporation electron injecting layer LiF, thickness is 1nm, The layer is electron injecting layer 7；
G) true to make aluminium (Al) layer that thickness is 80nm on electron injecting layer 7, the layer is that negative electrode is anti- Penetrate electrode layer 8；
The composition structure of obtained device is as shown in table 2.
Device embodiments 2
The difference of the present embodiment and device embodiments 1 is：The main body material of luminescent layer 5 of electroluminescent device Material is changed into the compounds of this invention 3 and compound GHN, and dopant material is Ir (ppy)3, the blending matter of three kinds of materials Amount is than being 60: 30: 10, and the composition structure of obtained device is as shown in table 2.
Device embodiments 3
The difference of the present embodiment and device embodiments 1 is：The main body material of luminescent layer 5 of electroluminescent device Material is changed into the compounds of this invention 8 and compound GHN, and dopant material is Ir (ppy)3, the blending matter of three kinds of materials Amount is than being 60: 30: 10, and the composition structure of obtained device is as shown in table 2.
Device embodiments 4
The difference of the present embodiment and device embodiments 1 is：The main body material of luminescent layer 5 of electroluminescent device Material is changed into the compounds of this invention 10 and compound GHN, and dopant material is Ir (ppy)3, the blending of three kinds of materials Mass ratio is 60: 30: 10, and the composition structure of obtained device is as shown in table 2.
Device embodiments 5
The difference of the present embodiment and device embodiments 1 is：The main body material of luminescent layer 5 of electroluminescent device Material is changed into the compounds of this invention 13 and compound GHN, and dopant material is Ir (ppy)3, the blending of three kinds of materials Mass ratio is 60: 30: 10, and the composition structure of obtained device is as shown in table 2.
Device embodiments 6
The difference of the present embodiment and device embodiments 1 is：The main body material of luminescent layer 5 of electroluminescent device Material is changed into the compounds of this invention 25 and compound GHN, and dopant material is Ir (ppy)3, the blending of three kinds of materials Mass ratio is 60: 30: 10, and the composition structure of obtained device is as shown in table 2.
Device embodiments 7
The difference of the present embodiment and device embodiments 1 is：The main body material of luminescent layer 5 of electroluminescent device Material is changed into the compounds of this invention 27 and compound GHN, and dopant material is Ir (ppy)3, the blending of three kinds of materials Mass ratio is 60: 30: 10, and the composition structure of obtained device is as shown in table 2.
Device embodiments 8
The difference of the present embodiment and device embodiments 1 is：The main body material of luminescent layer 5 of electroluminescent device Material is changed into the compounds of this invention 34 and compound GHN, dopant material Ir (ppy)3, the blending matter of three kinds of materials Amount is than being 60: 30: 10, and the composition structure of obtained device is as shown in table 2.
Device embodiments 9
The difference of the present embodiment and device embodiments 1 is：The main body material of luminescent layer 5 of electroluminescent device Material is changed into the compounds of this invention 36 and compound GHN, and dopant material is Ir (ppy)3, the blending of three kinds of materials Mass ratio is 60: 30: 10, and the composition structure of obtained device is as shown in table 2.
Device embodiments 10
The difference of the present embodiment and device embodiments 1 is：The main body material of luminescent layer 5 of electroluminescent device Material is changed into the compounds of this invention 46 and compound GHN, and dopant material is Ir (ppy)3, the blending of three kinds of materials Mass ratio is 60: 30: 10, and the composition structure of obtained device is as shown in table 2.
Device embodiments 11
The difference of the present embodiment and device embodiments 1 is：The main body material of luminescent layer 5 of electroluminescent device Material is changed into the compounds of this invention 51 and compound GHN, and dopant material is Ir (ppy)3, the blending of three kinds of materials Mass ratio is 60: 30: 10, and the composition structure of obtained device is as shown in table 2.
Device comparative example 1
The difference of the present embodiment and device embodiments 1 is：The main body material of luminescent layer 5 of electroluminescent device Material is changed into known compound CBP, and dopant material is Ir (ppy)3, doping mass ratio is 10%, obtained device Constitute structure as shown in table 2.
Complete after OLED luminescent devices, connected anode and negative electrode as described above with known drive circuit Come, the current efficiency of measurement device and the life-span of device.The test result of obtained device is shown in Table 3.
The composition structure of each device is as shown in table 2.The test result of device is shown in Table 3.
Table 2
Table 3
Numbering Current efficiency Color The LT95 life-spans
Device embodiments 1 1.8 Green glow 6.7
Device embodiments 2 1.7 Green glow 8.5
Device embodiments 3 2.1 Green glow 9.3
Device embodiments 4 2.3 Green glow 7.6
Device embodiments 5 2.2 Green glow 8.5
Device embodiments 6 2.1 Green glow 7.7
Device embodiments 7 2.3 Green glow 9.9
Device embodiments 8 2.2 Green glow 8.8
Device embodiments 9 2.4 Green glow 9.8
Device embodiments 10 2.3 Green glow 7.6
Device embodiments 11 2.4 Green glow 8.2
Device comparative example 1 1.0 Green glow 1.0
Note：Device detection performance is using device comparative example 1 as reference, and the device property indices of comparative example 1 are set to 1.0.The electric current effect of comparative example 1 Rate is 28cd/A (@10mA/cm2)；CIE chromaticity coordinates is (0.33,0.63)；LT95 life time decays are 2.5Hr under 5000 brightness.
Illustrate the compound of the invention synthesized in the devices as hole material below by way of device embodiments 12-16 Application effect.The manufacture craft of device embodiments 12-16 devices compared with device embodiments 1 of the present invention Identical, and employed identical baseplate material and electrode material, the thickness of electrode material is also kept Unanimously, except that luminescent layer dopant material uses Ir (ppy) in device architecture3, hole injection layer 3, sky The materials'use the compounds of this invention of cave transport layer/electronic barrier layer 4.Obtained device structure composition is as shown in table 4； The test result of obtained device is shown in Table 5.
Table 4
Table 5
Numbering Current efficiency Color Drive the life-span
Device embodiments 12 1.3 Green glow 3.5
Device embodiments 13 1.5 Green glow 4.2
Device embodiments 14 1.4 Green glow 4.5
Device embodiments 15 1.6 Green glow 3.8
Device embodiments 16 1.4 Green glow 4.2
Device comparative example 1 1.0 Green glow 1.0
Note：Device detection performance is using device comparative example 1 as reference, and the device property indices of comparative example 1 are set to 1.0.The electric current effect of comparative example 1 Rate is 28cd/A (@10mA/cm2)；CIE chromaticity coordinates is (0.33,0.63)；LT95 life time decays are 2.5Hr under 5000 brightness.
It can be seen that the organic compound of the present invention containing xanthene structure can be answered by the result of table 3 and table 5 Made for OLED luminescent devices, and compared with comparative example, either efficiency or life-span are than known The driving life-span that OLED material obtains larger change, particularly device obtains larger lifting.
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 (7)

1. a kind of electroluminescent organic material using xanthene as core, it is characterised in that the luminescent material Shown in structural formula such as formula (1)：
In formula (1), Ar1、Ar2It is each independent to be expressed as phenyl, xenyl or naphthyl；Ar1、Ar2 Can be with identical or different；R1、R2Respectively hydrogen or the structure represented using formula (2), and R1、R2No It is simultaneously hydrogen；
In formula (2), X1For oxygen atom, sulphur atom, selenium atom, C1-10Straight or branched alkyl substitution One kind in alkylidene, the alkylidene of aryl substitution, the amido of alkyl or aryl substitution；R3、R4It is only respectively On the spot choose structure shown in hydrogen or formula (3)；
In formula (3), a is selected fromX2、X3Independently for oxygen atom, sulphur Atom, selenium atom, C1-10Alkylidene, alkylidene, the alkyl of aryl substitution of straight or branched alkyl substitution Or one kind in the amido of aryl substitution；A and CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL4-CL5 Key, CL‘1-CL’2Key, CL‘2-CL’3Key, CL‘3-CL’4Key or CL‘4-CL’5Key is connected.
2. electroluminescent organic material 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； X3For oxygen atom, sulphur atom, selenium atom, C1-10The alkylidene of straight or branched alkyl substitution, aryl substitution Alkylidene, alkyl or aryl substitution amido in one kind.
3. electroluminescent organic material according to claim 1, it is characterised in that in the formula (1) R1、R2Respectively：
Any of；R1It is also denoted as hydrogen.
4. electroluminescent organic material according to claim 1, it is characterised in that the luminescent material Concrete structure formula is：
Any of.
5. a kind of method for preparing any one of Claims 1 to 4 electroluminescent organic material, its feature exists It is in the synthetic route of this method：
R1During for hydrogen, synthetic route is as follows：
R1When being not hydrogen, synthetic route is as follows：
Methods described is using Br-Ar2-Br as raw material, by grignard reaction, RMgBr is made, then with xanthenes Reactive ketone, generates the tertiary alcohol, the tertiary alcohol and H-Ar1-R1Or H-Ar1-I passes through friedel-crafts reaction, obtainedization Compound A or compound B, compound A or compound B with The luminescent material is made by C-N couplings.
6. a kind of organic electroluminescence for including any one of the Claims 1 to 5 electroluminescent organic material Part, it is characterised in that the organic electroluminescent electric material is as emitting layer material, for organic electroluminescent Diode.
7. a kind of organic electroluminescence for including any one of the Claims 1 to 5 electroluminescent organic material Part, it is characterised in that the organic electroluminescent electric material is used as hole injection layer, hole transmission layer and electronics Barrier material, for organic electroluminescent LED.
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CN107502343A (en) * 2017-09-05 2017-12-22 中节能万润股份有限公司 A kind of electroluminescent organic material and application
CN107522705A (en) * 2017-09-29 2017-12-29 江苏三月光电科技有限公司 A kind of oxa anthracenes organic compound and its application on OLED
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Application publication date: 20170818