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CN106008264A - Organic electroluminescent material, application and device thereof - Google Patents

Organic electroluminescent material, application and device thereof Download PDF

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CN106008264A
CN106008264A CN201610343808.9A CN201610343808A CN106008264A CN 106008264 A CN106008264 A CN 106008264A CN 201610343808 A CN201610343808 A CN 201610343808A CN 106008264 A CN106008264 A CN 106008264A
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CN106008264B (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 invention relates to an organic electroluminescent material, application and a device thereof, wherein the organic electroluminescent material is shown as the formula (I), wherein Ar1 and Ar2 are both aromatic substituent groups. The organic electroluminescent material has the characteristics that crystallization cannot easily occur among molecules; aggregation cannot easily occur; the film forming performance is good. In addition, the rigid groups in the molecules can improve the thermal stability of the luminescent material. The formula (I) is shown in the description.

Description

A kind of electroluminescent organic material, application and device thereof
Technical field
The present invention relates to the technical field of luminous organic material, particularly relate to a kind of electroluminescent organic material, application and Device.
Background technology
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology both can be used to make Make novel display product, it is also possible to be used for making novel illumination product.Owing to it has huge diving at aspects such as Flexible Displays In application, being expected to substitute existing liquid crystal display and fluorescent lighting, application prospect is quite varied.
At present, the existing rapid progress of OLED performance based on little molecule, reach the business-like stage, but organic electroluminescence has been sent out The problems such as the luminous efficiency of optical device and service life, limit the development of OLED technology.Affect the luminous efficiency of luminescent device Being many with the reason in service life, wherein fluorescence efficiency and the stability of luminescent material directly influences organic electroluminescence and sends out The performance of optical device, tradition organic fluorescence materials is luminous only with 25% singlet exciton being electrically excited formation, device interior Quantum efficiency relatively low (being up to 25%), phosphor material is worn between owing to SO coupling that heavy atom center is strong enhances being More, can effectively utilize singlet exciton and the Triplet exciton being electrically excited formation, make the internal quantum efficiency of device reach 100%.But phosphor material is usually metallo-organic complex, synthesis complexity, and needs the rare metal such as iridium, platinum, there is price 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 little singletstate-triplet poor (△ EST), and triplet excitons is permissible It is transformed into singlet exciton luminescence by passing through between anti-system.This can make full use of the singlet exciton and three being electrically excited lower formation Line state exciton, the internal quantum efficiency of device can reach 100%.Meanwhile, material structure is controlled, stable in properties, low price without Need precious metal, having a extensive future of OLEDs field.
For the actual demand of current OLED display Lighting Industry, the development of current OLED material is also nowhere near, and falls After in the requirement of panel manufacturing enterprise, therefore, the exploitation of high performance organic functional material is particularly important.
Summary of the invention
The technical problem to be solved be to provide one have intermolecular be difficult to crystallization, be difficult to assemble, well become The feature of film, and the rigid radical in molecule can improve the electroluminescent organic material of heat stability of material.
The technical scheme is that a kind of electroluminescent organic material, it is by lower formula I Shown in:
Wherein, Ar1And Ar2It is aromatic substituent group.
The invention has the beneficial effects as follows: the invention provides a kind of containing cyano group substituted 9,10-dihydroanthracene compound, This compound has intermolecular being difficult to as electroluminescent organic material and crystallizes, is difficult to gathering, the feature of good filming, molecule In rigid radical can improve the heat stability of material.
On the basis of technique scheme, the present invention can also do following improvement.
Further, the described Ar in described formula I1With described Ar2Identical.
Further, the described Ar in described formula I1With described Ar2Different.
Further, the described Ar in described formula I1And described Ar2Be selected from following radicals any one:
Further, any one in the compound shown in described formula I, specially following formula C01～C61:
Present invention also offers the application of a kind of electroluminescent organic material, the organic electroluminescence as described in above-mentioned any one Luminescent material is as the application of 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, described anode has been sequentially stacked described hole injection layer, Hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode；Wherein, described luminescent layer contains any of the above-described institute The electroluminescent organic material stated.
Beneficial effects of the present invention: present invention 9,10-based on TADF mechanism dihydroanthracene compound is as luminescent layer Dopant material is applied on organic luminescent device, the current efficiency of device, and power efficiency and external quantum efficiency all obtain changing the most greatly Kind；Meanwhile, this electroluminescent organic material makes electronics and hole more balance in the distribution of luminescent layer, is highly suitable as sending out Light material of main part；It addition, HOMO and lumo energy electron cloud efficiently separate realize less S1-T1 state energy gap, can be effective Improve exciton utilization rate and high fluorescent radiation efficiency, reduce the efficiency roll-off under high current density, reduce device voltage, improve device The current efficiency of part and life-span.
Accompanying drawing explanation
The structural representation of the organic electroluminescence device that Fig. 1 provides for the embodiment of the present invention three.
In accompanying drawing, the list of parts representated by each label is as follows:
101-anode, 102-hole transmission layer, 103-luminescent layer, 104-electron transfer layer, 105-electron injecting layer, 106- Negative electrode.
Detailed description of the invention
Being described principle and the feature of the present invention below in conjunction with accompanying drawing, example is served only for explaining the present invention, and Non-for limiting the scope of the present invention.It should be noted that in the case of not conflicting, in embodiments herein and embodiment Feature can be mutually combined.
Embodiment one
Present embodiments provide a kind of electroluminescent organic material, shown in its lower formula I:
Wherein, Ar1And Ar2It is aromatic substituent group.
Wherein, the described Ar in formula I1And Ar2Can be identical or different.
Described Ar in described (I)1、Ar2Be selected from following radicals any one:
Compound shown in described formula I, concretely any one in following formula C01～C61:
The electroluminescent organic material that the present embodiment provides, has intermolecular being difficult to and crystallizes, is difficult to gathering, good filming Feature, and the rigid radical in molecule can improve the heat stability of material.This electroluminescent organic material is sent out as OLED When the luminescent layer dopant material of optical device uses, the current efficiency of device, power efficiency and external quantum efficiency all obtain changing the most greatly Kind；Meanwhile, this electroluminescent organic material makes electronics and hole more balance in the distribution of luminescent layer, is highly suitable as sending out Light material of main part；It addition, HOMO and lumo energy electron cloud efficiently separate realize less S1-T1 state energy gap, can be effective Improve exciton utilization rate and high fluorescent radiation efficiency, reduce the efficiency roll-off under high current density, reduce device voltage, improve device The current efficiency of part and life-span.
Embodiment two
This gives the preparation method of part of compounds in C01～C61 that embodiment is a kind of.
Embodiment 1, the preparation of compound 1
The preparation of compound 1: in 1L there-necked flask, under nitrogen protection, adds intermediate 3 (34.0g, 0.08mol), and the third two Nitrile (6.6g, 0.10mol), the dichloromethane that 500mL is dried, ice bath is cooled to interior temperature 0～5 DEG C, slowly instills 22mL (0.20mol) titanium tetrachloride, dropping in about 0.5 hour is complete, is slowly dropped into 70mL pyridine, and dropping in about 1.0 hours is complete, drips Finishing and remove ice bath, the lower room temperature 20 of nitrogen protection～25 DEG C of stirrings are reacted 24 hours.Above reactant liquor is slowly poured into 300g mass Concentration is in the dilute hydrochloric acid of 10%, stirs 10min, separatory, collects organic facies, and decompression is sloughed solvent, obtained yellow solid, ice vinegar Yellow solid compound 1, HPLC purity 99.2%, yield 78.84% is obtained after acid recrystallization.
High resolution mass spectrum, ESI source, 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, being prepared as of intermediate 1:
The preparation of intermediate 1: addition anthraquinone (83.3g, 0.40mol) in 1L there-necked flask, ethylene glycol (27.9g, 0.45mol), 3.0g p-methyl benzenesulfonic acid, 450mL dimethylbenzene, it is heated to backflow, fraction water device water-dividing refluxes 10 hours.Reaction terminates After, washing, separatory, organic facies removed under reduced pressure solvent, column chromatography, toluene pet ether recrystallization, obtain white solid intermediate 1, HPLC purity 99.4%, yield 60.33%, MS (m/s): 252.3.
The preparation of intermediate 2: in the 1L there-necked flask being furnished with constant pressure funnel, addition magnesium metal (5.1g, 0.21mol), bromo-iodobenzene (56.6g, 0.20mol) will be dissolved in 300g oxolane, be placed in constant pressure funnel, Use nitrogen is protected, and heating there-necked flask reaches 65 DEG C to temperature in bottle, adds the tetrahydrochysene to bromo-iodobenzene by constant pressure funnel Tetrahydrofuran solution, is firstly added 50mL, after question response causes, slowly instills remainder, and 1h dropping is complete, reacts under reflux temperature 2h, is transferred in constant pressure funnel stand-by after being down to room temperature.Intermediate 1 (50.4g, 0.20mol) is dissolved in 200g oxolane Among be added in 2L there-necked flask, be then slowly added dropwise above-mentioned stand-by solution, under reflux temperature react 3h, reaction terminate after, cooling To 25 DEG C, above reactant liquor is slowly poured in the dilute hydrochloric acid that 200g mass concentration is 10%, stirs 15min, separatory, collect Organic facies, decompression is sloughed solvent, is obtained thick liquid, do not refine, and is directly used in next step reaction.
In above-mentioned gained thick liquid, add 250g benzene, add 1.42g (0.01mol) boron trifluoride diethyl etherate under stirring molten Liquid, 60～65 DEG C of reaction 4h, cancellation 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: collect above intermediate 2 (46.9g, 0.1mol), adds 250mL toluene and 50mL 85% Formic acid, be warming up to backflow, insulation reaction 10 hours.Separatory, washing, organic facies removed under reduced pressure solvent, column chromatography, obtain white Solid intermediate 3, HPLC purity 99.8%, yield 82.36%, MS (m/s): 424.0.
Embodiment 2, the preparation of compound C01:
In 250mL there-necked flask, logical nitrogen protection is lower adds compound 1 (4.71g, 0.01mol), compound M01 (2.75g, 0.015mol), sodium tert-butoxide (1.44g, 0.015mol), 0.15gpd2(dba)3, 0.10g tri-tert phosphorus, 100ml Toluene, is warming up to backflow under nitrogen protection, reacts 16 hours, stops reaction, cooling, separatory, and 50mL deionization is washed, collected organic Phase, sloughs solvent, and gained crude product uses silica gel column chromatography purification, obtains object C01, HPLC purity 99.9%, yield 86.38%.
High resolution mass spectrum, ESI source, 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, the preparation of compound C03
The preparation method of compound C03 is with embodiment 2, and difference is to use raw material M02 to replace in embodiment 2 M01.
High resolution mass spectrum, ESI source, 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, the preparation of compound C05
The preparation method of compound C05 is with embodiment 2, and difference is to use raw material M03 to replace in embodiment 2 M01.
High resolution mass spectrum, ESI source, 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, the preparation of compound C09
The preparation method of compound C09 is with embodiment 2, and difference is to use raw material M04 to replace in embodiment 2 M01.
High resolution mass spectrum, ESI source, 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, the preparation of compound C10
The preparation method of compound C10 is with embodiment 2, and difference is to use raw material M05 to replace in embodiment 2 M01.
High resolution mass spectrum, ESI source, 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, the preparation of compound C13
The preparation method of compound C13 is with embodiment 2, and difference is to use raw material M06 to replace in embodiment 2 M01.
High resolution mass spectrum, ESI source, 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
The preparation method of compound 2 is with embodiment 1, and difference is to use raw material triphenylamine to replace embodiment 1 In benzene.
High resolution mass spectrum, ESI source, 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, the preparation of compound C16
The preparation method of compound C16 is with embodiment 2, and it is real that difference is to use starting compound 2 and M07 to replace Execute the compound 1 and M01 in mode 2.
High resolution mass spectrum, ESI source, 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, the preparation of compound C20
The preparation method of compound C20 is with embodiment 9, and difference is to use M05 to replace in embodiment 9 M07。
High resolution mass spectrum, ESI source, 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, the preparation of compound C22
The preparation method of compound C22 is with embodiment 9, and difference is to use M08 to replace in embodiment 9 M07。
High resolution mass spectrum, ESI source, 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
The preparation method of compound 3 is with embodiment 1, and difference is to use raw material N-phenyl carbazole to replace embodiment party Benzene in formula 1.
High resolution mass spectrum, ESI source, 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, the preparation of compound C24
The preparation method of compound C24 is with embodiment 2, and difference is to use starting compound 3 to replace embodiment party Compound 1 in formula 2.
High resolution mass spectrum, ESI source, 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, the preparation of compound C27
The preparation method of compound C27 is with embodiment 2, and it is real that difference is to use starting compound 3 and M07 to replace Execute the compound 1 and M01 in mode 2.
High resolution mass spectrum, ESI source, 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, the preparation of compound C30
The preparation method of compound C30 is with embodiment 2, and it is real that difference is to use starting compound 3 and M05 to replace Execute the compound 1 and M01 in mode 2.
High resolution mass spectrum, ESI source, 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, the preparation of compound C33
The preparation method of compound C33 is with embodiment 2, and it is real that difference is to use starting compound 3 and M06 to replace Execute the compound 1 and M01 in mode 2.
High resolution mass spectrum, ESI source, 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 to use raw material bromobenzene to replace in embodiment 1 Benzene.
High resolution mass spectrum, ESI source, 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, the preparation of compound C36
The preparation method of compound C36 is with embodiment 2, and it is real that difference is to use starting compound 4 and M02 to replace Execute the compound 1 and M01 in mode 2.
High resolution mass spectrum, ESI source, 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, the preparation of compound C39
The preparation method of compound C39 is with embodiment 2, and it is real that difference is to use starting compound 4 and M04 to replace Execute the compound 1 and M01 in mode 2.
High resolution mass spectrum, ESI source, 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 5-bis-bromo-iodobenzene is replaced and implemented In mode 1 to bromo-iodobenzene.
High resolution mass spectrum, ESI source, 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, the preparation of compound C46
The preparation method of compound C46 is with embodiment 2, and difference is to use starting compound 5 to replace embodiment party Compound 1 in formula 2.
High resolution mass spectrum, ESI source, 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, the preparation of compound C48
The preparation method of compound C48 is with embodiment 2, and it is real that difference is to use starting compound 5 and M02 to replace Execute the compound 1 and M01 in mode 2.
High resolution mass spectrum, ESI source, 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
The preparation method of compound 6 is with embodiment 1, and difference is to use bromo-iodobenzene and triphenylamine between raw material to replace In embodiment 1 to bromo-iodobenzene and benzene.
High resolution mass spectrum, ESI source, 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, the preparation of compound C54
The preparation method of compound C54 is with embodiment 2, and difference is use starting compound 6 and replace enforcement Compound 1 in mode 2.
High resolution mass spectrum, ESI source, 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, the preparation of compound C56
The preparation method of compound C56 is with embodiment 2, and it is real that difference is to use starting compound 6 and M02 to replace Execute the compound 1 and M01 in mode 2.
High resolution mass spectrum, ESI source, 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
The preparation method of compound 7 is with embodiment 22, and difference is that using raw material N-phenyl carbazole to replace implements Triphenylamine in mode 22.
High resolution mass spectrum, ESI source, 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, the preparation of compound C58
The preparation method of compound C58 is with embodiment 2, and it is real that difference is to use starting compound 7 and M09 to replace Execute the compound 1 and M01 in mode 2.
High resolution mass spectrum, ESI source, 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, the preparation of compound C60
The preparation method of compound C60 is with embodiment 2, and it is real that difference is to use starting compound 7 and M04 to replace Execute the compound 1 and M01 in mode 2.
High resolution mass spectrum, ESI source, 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。
Present embodiments provide the preparation method of the part of compounds of the electroluminescent organic material that embodiment one provides, logical The compound that the preparation method that crossing the present embodiment provides obtains have intermolecular be difficult to crystallization, be difficult to assemble, good filming Rigid radical in feature, and molecule can improve the heat stability of material；This compound can be used for OLED luminescent device Luminescent layer dopant material so that electronics and hole more balance in the distribution of luminescent layer, can be effectively improved exciton utilization rate and height Fluorescent radiation efficiency, reduces the efficiency roll-off under high current density, reduces device voltage, improves current efficiency and the longevity of device Life.
Embodiment three
Present embodiments provide the application of a kind of electroluminescent organic material, the organic electroluminescent as described in embodiment one Material is as the application of 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, luminescence Layer 103, electron transfer layer 104, electron injecting layer 105 and negative electrode 106；Wherein, described in described anode 101 has been sequentially stacked Hole transmission layer 102, luminescent layer 103, electron transfer layer 104, electron injecting layer 105 and negative electrode 106；Wherein, described luminescent layer 103 containing electroluminescent organic material described above.
The organic electroluminescence device device that the present embodiment provides uses evaporation coating method to prepare, ito surface plate resistance used Being 10 Ω/, substrate is glass, has been photo-etched into the strip of long a width of 30mmx4mm before cleaning.In experiment, ITO processes step such as Under: carefully clean 3-4 time with ethanol and ITO special cleaning respectively, then use a large amount of deionized water rinsing, then use high pure nitrogen ITO surface is dried up, is placed on after drying up in the air dry oven that temperature constant is 110 DEG C and is dried, after about 5min, be transferred to oxygen 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, regulation Intracavity pressure is maintained at 10Pa, and radio-frequency voltage is adjusted to 300V afterwards, is transferred under vacuum evaporation room carries out after processing 2min One step experiment.Hole transmission layer NPB, Subjective and Objective luminescent layer and electron transfer layer once it is deposited with in being then placed in vacuum coating equipment TPBI, electron injecting layer LiF and cathodic metal aluminium lamination.In the preparation process of this organic electroluminescence device, the steaming of organic layer Being plated in organic vacuum room to carry out, vacuum is 10-4Pa, the evaporation thickness of organic material and evaporation rate are by Protek Universal counter U2000A type frequency counter controls, and corrects with polarisation ellipticity measuring instrument and step instrument.Have Machine material evaporation rate controlsLeft and right, the evaporation rate of metal Al controls, the electric piezo-electric of luminescent device Stream-light characteristic is by Keithley 2400 Sourcemeter, Keithley 2000 Currentment and the silicon light of correction Diode record, electroluminescent spectrum uses JY SPEX CCD3000 type fluorescence spectrophotometer and PR650Spectrascan Photometer completes to measure.The equal un-encapsulated of all devices, tests the most in an atmosphere.
In conjunction with the preparation process of above-mentioned device, preparing comparative device, 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 uses 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, in luminescence for material PX2PB In layer 103, the percentage ratio of doping is 6wt%) as dopant material, TPBi injects as electronics as electron transfer layer 104, LiF Layer 105, Al is as cathode layer 106, and concrete structure is as follows:
ITO/NPB (40nm)/6%wtPX2PB:mCP (20nm)/TPBi (40nm)/LiF (0.8nm)/Al.
The preparation of device 1-device 10, select successively embodiment two obtains compound-material C01, C05, C10, C20, C24, C30, C39, C46, C54, C60 are prepared according to carrying out device with comparative device identity unit structure, except that device The material of embodiment two preparation selected by luminescent layer dopant material, and concrete 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
Contrasting through device, the device using material of the present invention to prepare has lower driving voltage and more preferable color Purity, can be applied in the device preparation of electroluminescent organic material.
The foregoing is only presently preferred embodiments of the present invention, not in order to limit the present invention, all spirit in the present invention and Within principle, any modification, equivalent substitution and improvement etc. made, should be included within the scope of the present invention.

Claims (7)

1. an electroluminescent organic material, it is characterised in that shown in lower formula I:
Wherein, Ar1And Ar2It is aromatic substituent group.
Electroluminescent organic material the most according to claim 1, it is characterised in that the described Ar in described formula I1With institute State Ar2Identical.
Electroluminescent organic material the most according to claim 1, it is characterised in that the described Ar in described formula I1With institute State Ar2Different.
Electroluminescent organic material the most according to claim 1, it is characterised in that the described Ar in described formula I1And institute State Ar2Be selected from following radicals any one:
Electroluminescent organic material the most according to claim 1, it is characterised in that the compound shown in described formula I, tool Body is any one in following formula C01～C61:
6. the electroluminescent organic material described in an any one of claim 1 to 5 as in organic electroluminescence device extremely The application of a few functional layer.
7. an organic electroluminescence device, it is characterised in that include anode, hole transmission layer, luminescent layer, electron transfer layer, Electron injecting layer and negative electrode；Wherein, described anode has been sequentially stacked described hole transmission layer, luminescent layer, electron transfer layer, Electron injecting layer and negative electrode；Wherein, the organic electroluminescence that described luminescent layer contains according to any one of the claims 1 to 5 is sent out Luminescent material.
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