CN106008264B - A kind of electroluminescent organic material, application and its device - Google Patents

A kind of electroluminescent organic material, application and its device Download PDF

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CN106008264B
CN106008264B CN201610343808.9A CN201610343808A CN106008264B CN 106008264 B CN106008264 B CN 106008264B CN 201610343808 A CN201610343808 A CN 201610343808A CN 106008264 B CN106008264 B CN 106008264B
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CN106008264A (en
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高自良
刘英瑞
石宇
王元勋
徐岩
许强
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Valiant Co Ltd
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Abstract

The present invention relates to a kind of electroluminescent organic material, application and its device, electroluminescent organic material therein by following formula (I) Suo Shi, wherein, Ar1And Ar2It is aromatic substituent group.It has it is intermolecular be not easy to crystallize, be not easy to assemble, good filming the characteristics of, and the rigid radical in molecule can improve the heat endurance of luminescent material.

Description

A kind of electroluminescent organic material, application and its device
Technical field
The present invention relates to the technical field of luminous organic material, more particularly to a kind of electroluminescent organic material, using and Device.
Background technology
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology both can be used for make New display product is made, can be used for making novel illumination product.Due to its have in Flexible Displays etc. it is huge latent Applying, be expected to substitute existing liquid crystal display and fluorescent lighting, application prospect is quite varied.
At present, the existing rapid progress of the OLED performances based on small molecule, the commercialized stage has been reached, but organic electroluminescence is sent out The problems such as luminous efficiency and service life of optical device, limit the development of OLED technology.Influence the luminous efficiency of luminescent device And the reason for service life is many, wherein the fluorescence efficiency of luminescent material and stability directly influence organic electroluminescence hair The performance of optical device, traditional organic fluorescence materials can only utilize and be electrically excited 25% singlet exciton to be formed and light, device it is interior Quantum efficiency is relatively low (up to 25%), and phosphor material is worn between being because the strong SO coupling in heavy atom center enhances More, the singlet exciton and Triplet exciton that effectively can be formed using being electrically excited, reach the internal quantum efficiency of device 100%.But phosphor material is usually metallo-organic complex, synthesis is complicated, and needs the rare metals such as iridium, platinum, price be present Costliness, stability of material is poor, and device efficiency tumbles the problems such as serious.
Hot activation delayed fluorescence (TADF) material is the 3 developed after organic fluorescence materials and organic phosphorescent material For luminous organic material.Such material typically has that small singlet-triplet is poor (△ EST), and triplet excitons can be with By it is counter be between pass through and be transformed into singlet exciton and light.This can make full use of the singlet exciton for being electrically excited lower formation and three Line state exciton, the internal quantum efficiency of device can reach 100%.Meanwhile material structure is controllable, property is stable, cheap nothing Precious metal is needed, in having a extensive future for OLEDs fields.
For the actual demand that current OLED shows Lighting Industry, the development of OLED material is also far from enough at present, falls After the requirement of panel manufacturing enterprise, therefore, the exploitation of high performance organic functional material is particularly important.
The content of the invention
The technical problems to be solved by the invention be to provide it is a kind of have it is intermolecular be not easy to crystallize, be not easy to assemble, well into The characteristics of film, and the rigid radical in molecule can improve the electroluminescent organic material of the heat endurance of material.
The technical scheme that the present invention solves above-mentioned technical problem is as follows：A kind of electroluminescent organic material, it is by following formula (I) It is shown：
Wherein, Ar1And Ar2It is aromatic substituent group.
The beneficial effects of the invention are as follows：The invention provides it is a kind of containing cyano group substitution 9,10- dihydroanthracene compounds, The compound as electroluminescent organic material have it is intermolecular be not easy to crystallize, be not easy to assemble, good filming the characteristics of, molecule In rigid radical can improve the heat endurance of material.
On the basis of above-mentioned technical proposal, the present invention can also do following improvement.
Further, the Ar in the formula (I)1With the Ar2It is identical.
Further, the Ar in the formula (I)1With the Ar2It is different.
Further, the Ar in the formula (I)1And the Ar2It is selected from any one in following radicals：
Further, the compound shown in the formula (I), any one in specially following formula C01~C61：
Present invention also offers a kind of application of electroluminescent organic material, the organic electroluminescence described in any one as described above Application of the luminescent material as at least one functional layer in organic electroluminescence device.
Present invention also offers a kind of organic electroluminescence device, it include anode, hole injection layer, hole transmission layer, Luminescent layer, electron transfer layer, electron injecting layer and negative electrode；Wherein, be sequentially stacked on the anode hole injection layer, Hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode；Wherein, the luminescent layer contains any of the above-described institute The electroluminescent organic material stated.
Beneficial effects of the present invention：9,10- dihydroanthracene compounds of the invention based on TADF mechanism are as luminescent layer Dopant material is applied on organic luminescent device, and the current efficiency of device, power efficiency and external quantum efficiency obtain changing greatly very much It is kind；Meanwhile the electroluminescent organic material causes electronics and hole more to be balanced in the distribution of luminescent layer, is highly suitable as sending out Light material of main part；In addition, the achievable less S1-T1 states energy gap that HOMO and lumo energy electron cloud efficiently separate, can be effective Exciton utilization rate and high fluorescent radiation efficiency are improved, reduces the efficiency roll-off under high current density, reduces device voltage, improves device The current efficiency of part and life-span.
Brief description of the drawings
Fig. 1 is the structural representation for the organic electroluminescence device that the embodiment of the present invention three provides.
In accompanying drawing, the list of parts representated by each label is as follows：
101- anodes, 102- hole transmission layers, 103- luminescent layers, 104- electron transfer layers, 105- electron injecting layers, 106- Negative electrode.
Embodiment
The principle and feature of the present invention are described below in conjunction with accompanying drawing, the given examples are served only to explain the present invention, and It is non-to be used to limit the scope of the present invention.It should be noted that in the case where not conflicting, in embodiments herein and embodiment Feature can be mutually combined.
Embodiment one
A kind of electroluminescent organic material is present embodiments provided, shown in its following formula (I)：
Wherein, Ar1And Ar2It is aromatic substituent group.
Wherein, the Ar in formula (I)1And Ar2Can be with identical or different.
The Ar in (I)1、Ar2It may be selected from any one in following radicals：
Compound shown in the formula (I), concretely any one in following formula C01~C61：
The electroluminescent organic material that the present embodiment provides, have it is intermolecular be not easy to crystallize, be not easy to assemble, good filming The characteristics of, and the rigid radical in molecule can improve the heat endurance of material.The electroluminescent organic material is sent out as OLED The luminescent layer dopant material of optical device is in use, the current efficiency of device, power efficiency and external quantum efficiency obtain changing greatly very much It is kind；Meanwhile the electroluminescent organic material causes electronics and hole more to be balanced in the distribution of luminescent layer, is highly suitable as sending out Light material of main part；In addition, the achievable less S1-T1 states energy gap that HOMO and lumo energy electron cloud efficiently separate, can be effective Exciton utilization rate and high fluorescent radiation efficiency are improved, reduces the efficiency roll-off under high current density, reduces device voltage, improves device The current efficiency of part and life-span.
Embodiment two
This gives the preparation method of the part of compounds in a kind of C01~C61 of embodiment.
Embodiment 1, the preparation of compound 1
The preparation of compound 1：In 1L there-necked flasks, under nitrogen protection, intermediate 3 (34.0g, 0.08mol) is added, the third two Nitrile (6.6g, 0.10mol), the dichloromethane that 500mL is dried, ice bath are cooled to interior 0~5 DEG C of temperature, slowly instill 22mL (0.20mol) titanium tetrachloride, it is added dropwise within about 0.5 hour, is slowly dropped into 70mL pyridines, is added dropwise within about 1.0 hours, drips Finish and remove ice bath, lower 20~25 DEG C of the room temperature stirring reaction 24 hours of nitrogen protection.Above reaction solution is slowly poured into 300g mass Concentration is in 10% watery hydrochloric acid, stirs 10min, and organic phase is collected in liquid separation, and decompression sloughs solvent, obtains yellow solid, ice vinegar Yellow solid compound 1, HPLC purity 99.2%, yield 78.84% are obtained after acid recrystallization.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C29H17BrN2, theoretical value 472.0575, test value, 472.0577.Elementary analysis (C29H17BrN2), theoretical value C：73.58 H：3.62 N：5.92, measured value C：73.60 H：3.64 N：5.93.
Wherein, intermediate 1 is prepared as：
The preparation of intermediate 1：The addition anthraquinone (83.3g, 0.40mol) in 1L three-necked flasks, ethylene glycol (27.9g, 0.45mol), 3.0g p-methyl benzenesulfonic acid, 450mL dimethylbenzene, it is heated to flowing back, fraction water device water-dividing flows back 10 hours.Reaction terminates Afterwards, washing, liquid separation, organic phase removed under reduced pressure solvent, column chromatography, toluene pet ether recrystallization, white solid intermediate 1 is obtained, HPLC purity 99.4%, yield 60.33%, MS (m/s)：252.3.
The preparation of intermediate 2：In the 1L there-necked flasks equipped with constant pressure funnel, addition magnesium metal (5.1g, 0.21mol), bromo-iodobenzene (56.6g, 0.20mol) will be dissolved in 300g tetrahydrofurans, be placed in constant pressure funnel, Protected using nitrogen, heat temperature in there-necked flask to bottle and reach 65 DEG C, the tetrahydrochysene to bromo-iodobenzene is added by constant pressure funnel Tetrahydrofuran solution, 50mL is firstly added, after question response triggers, slowly instills remainder, 1h is added dropwise, and is reacted under reflux temperature 2h, be down to after room temperature be transferred to it is stand-by in constant pressure funnel.Intermediate 1 (50.4g, 0.20mol) is dissolved in 200g tetrahydrofurans Among be added in 2L there-necked flasks, above-mentioned stand-by solution is then slowly added dropwise, reacts 3h under reflux temperature, after reaction terminates, cooling To 25 DEG C, above reaction solution is slowly poured into the watery hydrochloric acid that 200g mass concentrations are 10%, stirs 15min, liquid separation, collect Organic phase, decompression slough solvent, obtain thick liquid, without refining, are directly used in reacting in next step.
250g benzene is added into above-mentioned gained thick liquid, it is molten to stir lower addition 1.42g (0.01mol) BFEE Liquid, 60~65 DEG C of reaction 4h, is quenched reaction, removed under reduced pressure solvent, column chromatography obtains intermediate 2, HPLC purity 99.7%, yield 42.68%, MS (m/s)：468.1.
The preparation of intermediate 3：Above intermediate 2 (46.9g, 0.1mol) is collected, adds 250mL toluene and 50mL 85% Formic acid, be warming up to backflow, insulation reaction 10 hours.Liquid separation, washing, organic phase removed under reduced pressure solvent, column chromatography, obtains white Solid intermediate 3, HPLC purity 99.8%, yield 82.36%, MS (m/s)：424.0.
Embodiment 2, compound C01 preparation：
In 250mL there-necked flasks, lead to the lower addition compound 1 (4.71g, 0.01mol) of nitrogen protection, compound M01 (2.75g, 0.015mol), sodium tert-butoxide (1.44g, 0.015mol), 0.15gpd2(dba)3, 0.10g tri-tert phosphorus, 100ml Toluene, backflow is warming up under nitrogen protection, reacts 16 hours, stops reacting, is cooled, liquid separation, the washing of 50mL deionizations, collected organic Phase, solvent is sloughed, gained crude product is purified using silica gel column chromatography, obtains object C01, HPLC purity 99.9%, yield 86.38%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C41H25N3O, theoretical value 575.1998, test value 575.1995.Elementary analysis (C41H25N3O), theoretical value C：85.54 H：4.38 N：7.30 O：2.78, measured value C：85.56, H：4.37 N：7.33 O：2.74.
Embodiment 3, compound C03 preparation
Compound C03 preparation method is with embodiment 2, and difference is in embodiment 2 is replaced using raw material M02 M01.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C44H31N3, theoretical value 601.2518, test value 601.2516.Elementary analysis (C44H31N3), theoretical value C：87.82 H：5.19 N：6.98, measured value C：87.80 H：5.20 N： 7.00。
Embodiment 4, compound C05 preparation
Compound C05 preparation method is with embodiment 2, and difference is in embodiment 2 is replaced using raw material M03 M01.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C45H27N3, theoretical value 609.2205, test value 609.2202.Elementary analysis (C45H27N3), theoretical value C：88.64 H：4.46 N：6.89, measured value C：88.66 H：4.44 N： 6.89。
Embodiment 5, compound C09 preparation
Compound C09 preparation method is with embodiment 2, and difference is in embodiment 2 is replaced using raw material M04 M01.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C43H27N3, theoretical value 585.2205, test value 585.2203.Elementary analysis (C43H27N3), theoretical value C：88.18 H：4.65 N：7.17, measured value C：88.15 H：4.66 N： 7.19。
Embodiment 6, compound C10 preparation
Compound C10 preparation method is with embodiment 2, and difference is in embodiment 2 is replaced using raw material M05 M01.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C47H30N4, theoretical value 650.2470, test value 650.2473.Elementary analysis (C47H30N4), theoretical value C：86.74 H：4.65 N：8.61, measured value C：86.77 H：4.63 N： 8.60。
Embodiment 7, compound C13 preparation
Compound C13 preparation method is with embodiment 2, and difference is in embodiment 2 is replaced using raw material M06 M01.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C54H35N3, theoretical value 725.2831, test value 725.2833.Elementary analysis (C54H35N3), theoretical value C：89.35 H：4.86 N：5.79, measured value C：89.33 H：4.87 N： 5.80。
Embodiment 8, the preparation of compound 2
With embodiment 1, difference is to replace embodiment 1 using raw material triphenylamine the preparation method of compound 2 In benzene.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C41H26BrN3, theoretical value 639.1310, test value 639.1312.Elementary analysis (C41H26BrN3), theoretical value C：76.88 H：4.09 N：6.56, measured value C：76.86 H： 4.11 N：6.58.
Embodiment 9, compound C16 preparation
With embodiment 2, difference is to replace in fact using starting compound 2 and M07 compound C16 preparation method Apply compound 1 and the M01 in mode 2.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C53H34N4, theoretical value 726.2783, test value 726.2780.Elementary analysis (C53H34N4), theoretical value C：87.58 H：4.71 N：7.71, measured value C：87.60 H：4.70 N： 7.70。
Embodiment 10, compound C20 preparation
Compound C20 preparation method is with embodiment 9, and difference is in embodiment 9 is replaced using M05 M07。
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C59H39N5, theoretical value 817.3205, test value 817.3202.Elementary analysis (C59H39N5), theoretical value C：86.63 H：4.81 N：8.56, measured value C：86.61 H：4.81 N： 8.58。
Embodiment 11, compound C22 preparation
Compound C22 preparation method is with embodiment 9, and difference is in embodiment 9 is replaced using M08 M07。
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C62H43N5, theoretical value 857.3518, test value 857.3514.Elementary analysis (C62H43N5), theoretical value C：86.79 H：5.05 N：8.16, measured value C：86.77 H：5.08 N： 8.15。
Embodiment 12, the preparation of compound 3
With embodiment 1, difference is to replace embodiment party using raw material N- phenyl carbazoles the preparation method of compound 3 Benzene in formula 1.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C41H24BrN3, theoretical value 637.1154, test value 637.1158.Elementary analysis (C41H24BrN3), theoretical value C：77.12 H：3.79 N：6.58, measured value C：77.11 H：3.82 N：6.57.
Embodiment 12, compound C24 preparation
With embodiment 2, difference is to replace embodiment party using starting compound 3 compound C24 preparation method Compound 1 in formula 2.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C53H32N4O, theoretical value 740.2576, test value 740.2573.Elementary analysis (C53H32N4O), theoretical value C：85.92 H：4.35 N：7.56 O：2.16, measured value C：85.94, H：4.37 N：7.54,O：2.15.
Embodiment 13, compound C27 preparation
With embodiment 2, difference is to replace in fact using starting compound 3 and M07 compound C27 preparation method Apply compound 1 and the M01 in mode 2.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C53H32N4, theoretical value 724.2627, test value 724.2629.Elementary analysis (C53H32N4), theoretical value C：87.82 H：4.45 N：7.73, measured value C：87.80 H：4.45 N： 7.75。
Embodiment 14, compound C30 preparation
With embodiment 2, difference is to replace in fact using starting compound 3 and M05 compound C30 preparation method Apply compound 1 and the M01 in mode 2.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C59H37N5, theoretical value 724.2627, test value 724.2629.Elementary analysis (C59H37N5), theoretical value C：87.82 H：4.45 N：7.73, measured value C：87.80 H：4.45 N： 7.75。
Embodiment 15, compound C33 preparation
With embodiment 2, difference is to replace in fact using starting compound 3 and M06 compound C33 preparation method Apply compound 1 and the M01 in mode 2.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C66H42N4, theoretical value 890.3409, test value 890.3404.Elementary analysis (C66H42N4), theoretical value C：88.96 H：4.75 N：6.29, measured value C：88.93 H：4.75 N： 6.32。
Embodiment 16, the preparation of compound 4
The preparation method of compound 4 is with embodiment 1, and difference is in embodiment 1 is replaced using raw material bromobenzene Benzene.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C29H16Br2N2, theoretical value 549.9680, test value 549.9683.Elementary analysis (C29H16Br2N2), theoretical value C：63.07 H：2.92 N：5.07, measured value C：63.10 H： 2.94 N：5.11.
Embodiment 17, compound C36 preparation
With embodiment 2, difference is to replace in fact using starting compound 4 and M02 compound C36 preparation method Apply compound 1 and the M01 in mode 2.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C59H44N4, theoretical value 808.3566, test value 808.3561.Elementary analysis (C59H44N4), theoretical value C：87.59 H：5.48 N：6.93, measured value C：87.54 H：5.51 N： 6.95。
Embodiment 18, compound C39 preparation
With embodiment 2, difference is to replace in fact using starting compound 4 and M04 compound C39 preparation method Apply compound 1 and the M01 in mode 2.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C57H36N4, theoretical value 776.2940, test value 776.2943.Elementary analysis (C57H36N4), theoretical value C：88.12 H：4.67 N：7.21, measured value C：88.14 H：4.70 N： 7.16。
Embodiment 19, the preparation of compound 5
The preparation method of compound 5 is with embodiment 1, and difference is to use raw material 3, and the bromo-iodobenzenes of 5- bis-, which are replaced, to be implemented In mode 1 to bromo-iodobenzene.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C29H16Br2N2, theoretical value 549.9680, test value 549.9684.Elementary analysis (C29H16Br2N2), theoretical value C：63.07 H：2.92 N：5.07, measured value C：63.09 H： 2.95 N：5.11.
Embodiment 20, compound C46 preparation
With embodiment 2, difference is to replace embodiment party using starting compound 5 compound C46 preparation method Compound 1 in formula 2.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C53H32N4O2, theoretical value 756.2525, test value 756.2528.Elementary analysis (C53H32N4O2), theoretical value C：84.11 H：4.26 N：7.40 O：4.23, measured value C：84.12, H：4.28 N：7.36 O：4.24.
Embodiment 21, compound C48 preparation
With embodiment 2, difference is to replace in fact using starting compound 5 and M02 compound C48 preparation method Apply compound 1 and the M01 in mode 2.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C59H44N4, theoretical value 808.3566, test value 808.3569.Elementary analysis (C59H44N4), theoretical value C：87.59 H：5.48 N：6.93, measured value C：87.55 H：5.50 N： 6.95。
Embodiment 22, the preparation of compound 6
With embodiment 1, difference is to replace using bromo-iodobenzene between raw material and triphenylamine the preparation method of compound 6 In embodiment 1 to bromo-iodobenzene and benzene.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C41H26BrN3, theoretical value 639.1310, test value 639.1312.Elementary analysis (C41H26BrN3), theoretical value C：76.88 H：4.09 N：6.56, measured value C：76.81 H：4.07 N：6.53.
Embodiment 23, compound C54 preparation
With embodiment 2, difference is using starting compound 6 and replaces implementation compound C54 preparation method Compound 1 in mode 2.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C53H34N4O, theoretical value 742.2733, test value 742.2738.Elementary analysis (C53H34N4O), theoretical value C：85.69 H：4.61 N：7.54 O：2.15, measured value C：85.66, H：4.63 N：7.56 O：2.15.
Embodiment 24, compound C56 preparation
With embodiment 2, difference is to replace in fact using starting compound 6 and M02 compound C56 preparation method Apply compound 1 and the M01 in mode 2.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C56H40N4, theoretical value 768.3253, test value 768.3255.Elementary analysis (C56H40N4), theoretical value C：87.47 H：5.24 N：7.29, measured value C：87.43 H：5.26 N： 7.31。
Embodiment 25, the preparation of compound 7
With embodiment 22, difference is to replace using raw material N- phenyl carbazoles to be implemented the preparation method of compound 7 Triphenylamine in mode 22.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C41H24BrN3, theoretical value 637.1154, test value 637.1160.Elementary analysis (C41H24BrN3), theoretical value C：77.12 H：3.79 N：6.58, measured value C：77.13 H：3.81 N：6.56.
Embodiment 26, compound C58 preparation
With embodiment 2, difference is to replace in fact using starting compound 7 and M09 compound C58 preparation method Apply compound 1 and the M01 in mode 2.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C53H32N4S, theoretical value 756.2348, test value 756.2344.Elementary analysis (C53H32N4S), theoretical value C：84.10 H：4.26 N：7.40, measured value C：84.12 H：4.29 N：7.42.
Embodiment 27, compound C60 preparation
With embodiment 2, difference is to replace in fact using starting compound 7 and M04 compound C60 preparation method Apply compound 1 and the M01 in mode 2.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C55H34N4, theoretical value 750.2783, test value 750.2788.Elementary analysis (C55H34N4), theoretical value C：87.98 H：4.56 N：7.46, measured value C：87.95 H：4.57 N： 7.48。
The preparation method of the part of compounds for the electroluminescent organic material that embodiment one provides is present embodiments provided, is led to Cross the compound that the preparation method of the present embodiment offer obtains have it is intermolecular be not easy to crystallize, be not easy to assemble, good filming Feature, and the rigid radical in molecule can improve the heat endurance of material；The compound can be used for OLED luminescent devices Luminescent layer dopant material so that electronics and hole more balance in the distribution of luminescent layer, can effectively improve exciton utilization rate and height Fluorescent radiation efficiency, the efficiency roll-off under high current density is reduced, reduce device voltage, improve current efficiency and the longevity of device Life.
Embodiment three
Present embodiments provide a kind of application of electroluminescent organic material, the organic electroluminescent as described in embodiment one Application of the material as at least one functional layer in organic electroluminescence device.
The present embodiment additionally provides a kind of organic electroluminescence device, and it includes anode 101, hole transmission layer 102, lighted Layer 103, electron transfer layer 104, electron injecting layer 105 and negative electrode 106；Wherein, it has been sequentially stacked on the anode 101 described Hole transmission layer 102, luminescent layer 103, electron transfer layer 104, electron injecting layer 105 and negative electrode 106；Wherein, the luminescent layer 103 contain electroluminescent organic material described above.
The organic electroluminescence device device that the present embodiment provides is prepared using evaporation coating method, ito surface plate resistance used For 10 Ω/, substrate is glass, and long a width of 30mmx4mm strip has been photo-etched into before cleaning.ITO processing steps are such as in experiment Under：Carefully cleaned 3-4 times with ethanol and ITO special cleanings respectively, then with a large amount of deionized water rinsings, then use high pure nitrogen ITO surfaces are dried up, be placed on after drying temperature it is constant be 110 DEG C air dry oven in dry, be transferred to oxygen after about 5min Ion processing room.Process chamber is evacuated to vacuum to below 4Pa with mechanical pump, then continues to be passed through high purity oxygen gas to process chamber, is adjusted Intracavitary pressure is maintained at 10Pa, and radio-frequency voltage regulation is arrived into 300V afterwards, and being transferred to vacuum evaporation room after processing 2min is carried out down One step is tested.It is then placed in vacuum coating equipment and hole transmission layer NPB, Subjective and Objective luminescent layer and electron transfer layer is once deposited TPBI, electron injecting layer LiF and cathodic metal aluminium lamination.In the preparation process of the organic electroluminescence device, the steaming of organic layer It is plated in the progress of organic vacuum room, vacuum 10-4Pa, the evaporation thickness and evaporation rate of organic material are by Protek Universal counter U2000A types frequency counter controls, and is corrected with polarisation ellipticity measuring instrument and step instrument.Have The control of machine material evaporation rate existsLeft and right, metal Al evaporation rate control exist, the electric piezo-electric of luminescent device Stream-light characteristic by Keithley 2400 Sourcemeter, Keithley 2000 Currentment and correction silicon light Diode records, and electroluminescent spectrum uses JY SPEX CCD3000 types XRFs and PR650Spectrascan Photometer completes to measure.All devices are un-encapsulated, directly test in an atmosphere.
With reference to the preparation process of above-mentioned device, comparative device is prepared, comparative device is made with ITO (tin indium oxide) electro-conductive glass For anode 101, using NPB as hole transmission layer 102, luminescent layer 103 is using mCP as material of main part, thermal activation delayed fluorescence (HOMO energy level 5.44ev, lumo energy 2.92ev, singlet level 2.61, triplet energy level 2.58, are lighting material PX2PB The percentage adulterated in layer 103 is 6wt%) dopant material is used as, TPBi is as electron transfer layer 104, and LiF is as electron injection For 105, Al of layer as cathode layer 106, concrete structure is as follows：
ITO/NPB (40nm)/6%wtPX2PB：mCP(20nm)/TPBi(40nm)/LiF(0.8nm)/Al.
The preparation of device 1- devices 10, successively from obtained in embodiment two compound-material C01, C05, C10, C20, C24, C30, C39, C46, C54, C60 carry out device preparation according to comparative device identity unit structure, except that device Luminescent layer dopant material selects material prepared by embodiment two, and specific comparison structure is as shown in table 1 below, the test knot of obtained device Fruit is as shown in table 2：
Table 1
Table 2
Contrasted by device, the device prepared using material of the present invention has lower driving voltage and more preferable color Purity, it can be applied in the device preparation of electroluminescent organic material.
The foregoing is only presently preferred embodiments of the present invention, be not intended to limit the invention, it is all the present invention spirit and Within principle, any modification, equivalent substitution and improvements made etc., it should be included in the scope of the protection.

Claims (3)

1. a kind of electroluminescent organic material, it is characterised in that by following formula (I) Suo Shi：
Compound shown in the formula (I), any one in specially following formula C01~C61：
2. the electroluminescent organic material described in a kind of claim 1 is as at least one function in organic electroluminescence device The application of layer.
A kind of 3. organic electroluminescence device, it is characterised in that including anode, hole transmission layer, luminescent layer, electron transfer layer, Electron injecting layer and negative electrode；Wherein, be sequentially stacked on the anode hole transmission layer, luminescent layer, electron transfer layer, Electron injecting layer and negative electrode；Wherein, the luminescent layer contains the electroluminescent organic material described in the claims 1.
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