CN106188026B - A kind of unsymmetric structure electroluminescent organic material and its application - Google Patents

A kind of unsymmetric structure electroluminescent organic material and its application Download PDF

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CN106188026B
CN106188026B CN201610518886.8A CN201610518886A CN106188026B CN 106188026 B CN106188026 B CN 106188026B CN 201610518886 A CN201610518886 A CN 201610518886A CN 106188026 B CN106188026 B CN 106188026B
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yellow solid
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CN106188026A (en
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高树坤
孙晟源
张江峰
盛磊
崔明
刘晓鹏
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Valiant Co Ltd
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Abstract

The invention discloses a kind of unsymmetric structure electroluminescent organic material and its applications, belong to organic photoelectrical material technical field.It includes the compound with molecular structure as follows:Wherein, X1For any one in carbazole and its deriveding group, two aromatic amine groups, X2For any one in phenoxazine and its deriveding group, dibenzofurans and its deriveding group, triazine ring deriveding group, aromatic group.This kind of new construction of the invention has the characteristics that suitable molecular conjugation length, the nonplanar structure of height and molecular mass appropriate, makes it have good thin film stability, suitable molecular entergy level.Such material of the invention has the luminescent properties of preferable blue phosphor material of main part, overall performance is substantially better than commercial materials mCP, same device design, in the present invention most compounds to open bright voltage lower, maximum current is more efficient, illustrates the prospect that this kind of material involved in the present invention has some commercial potential and further develops.

Description

A kind of unsymmetric structure electroluminescent organic material and its application
Technical field
The present invention relates to a kind of unsymmetric structure electroluminescent organic material and its applications, belong to organic photoelectrical material technology Field.
Background technique
Pope et al. has found the Electroluminescence Properties of monocrystalline anthracene in nineteen sixty-five for the first time, this is the first electricity of organic compound Photoluminescence phenomenon, by the continuous development of many years, organic electroluminescence device can both be used to manufacture new display product, can also For making novel illumination product, to be expected to replace available liquid crystal to show and fluorescent lighting.
Currently, the commodity based on OLED display technology, have been carried out industrialization.Compared with liquid crystal type display technology, OLED Display technology has thin self-luminous, radiationless, light weight, thickness, wide viewing angle, wide colour gamut, colour stable, fast response time, ring Border adapts to many advantages, such as strong, achievable Flexible Displays, and therefore, OLED display technology is obtaining people and more and more paying close attention to With corresponding Technical investment.
Early in nineteen thirty-seven, two from London are engaged in the scholar W.V.Mayneord and E.M.F.Roe of cancer research, hair The table paper of one ultra-violet absorption spectrum feature about complicated aryl radical compound, the paper have carried out a variety of aromatizations The test and comparison for closing the ultra-violet absorption spectrum data of object, wherein describing a kind of compound --- 9,9,10,10- tetramethyls- 9,10- dihydro-dibenzo anthracenes, it has characteristic ultraviolet absorption similar with naphthalene nucleus, but the two molecular structure significant difference, article Corresponding specific data are as shown in Figure 2:
Data according to fig. 2, it may be speculated that 9,9,10,10- tetramethyl -9,10- dihydro-dibenzo anthracene center rings 9,10 Reach saturation state simultaneously, weaken or obstructed the two-part molecular conjugation in left and right, causes the presence of similar with individual naphthalene The spectral absorption characteristics of loop section.But this structure is again dramatically different with naphthalene nucleus, has better stereoeffect, if Different carbazoles, aromatic amine, phenoxazine class, dibenzofurans class, triazines are introduced in the active site of its structure, even Fragrant class formation increases its two sides conjugate length, obtained series compound, with the application of the field OLED to some extent Prospect.
Summary of the invention
An object of the present invention is to provide a kind of unsymmetric structure electroluminescent organic material.Organic Electricity of the invention Electroluminescent material, glass transition temperature, suitable HOMO energy level and lumo energy with higher, wider energy gap and suitable S1 Energy level.
The technical scheme to solve the above technical problems is that a kind of unsymmetric structure electroluminescent organic material, Including the compound with molecular structure shown in formula 1:
Wherein, X1For any one in carbazole and its deriveding group, two aromatic amine groups, X2For phenoxazine and its derivative Group, dibenzofurans and its deriveding group, triazine ring deriveding group, any one in aromatic group.
The present invention is using tetramethyl dibenzanthracene as the compound of the unsymmetric structure of skeleton, i.e. compound shown in formula 1 has Higher glass transition temperature, suitable HOMO energy level and lumo energy, wider energy gap；It is organic that such material can be used as small molecule The functional layer of electroluminescent device, is applied in field of organic electroluminescence, is optimized by device architecture, can be obviously improved organic The photoelectric properties of electroluminescent device and its service life.
Based on the above technical solution, the present invention can also be improved as follows.
Further, the X1For any one in following group:
Beneficial effect using above-mentioned further scheme is: having obtained more suitable molecular size, nonplanar space is stood Body structure and the distribution of suitable molecular entergy level.
Further, the X2For any one in following group:
Beneficial effect using above-mentioned further scheme is: having obtained more suitable molecular size, nonplanar space is stood Body structure and the distribution of suitable molecular entergy level.
Further, the concrete structure formula of the unsymmetric structure electroluminescent organic material is one in following C01-C56 Kind is a variety of:
Beneficial effect using above-mentioned further scheme is: HOMO and lumo energy, S1 energy level are calculated by molecular simulation, Can arrange in pairs or groups existing finished commercial prod's material, and they pass through late device evaluation test, it is thus identified that excellent photoelectric properties.
The second object of the present invention is to provide the application of above-mentioned unsymmetric structure electroluminescent organic material.
The technical scheme to solve the above technical problems is that a kind of unsymmetric structure electroluminescent organic material Using in prepared organic electroluminescence device, at least one functional layer, which contains unsymmetric structure as described above, to be had Electroluminescent material.
Prepared organic electroluminescence device generally comprises the ITO Conducting Glass (anode) being sequentially overlapped, hole Implanted layer, hole transmission layer (NPB), luminescent layer (material or DPVBi in the present invention), electron transfer layer (TPBI), electronics note Enter layer (LiF) and cathode layer (Al).The structural schematic diagram of prepared organic electroluminescence device is as shown in Figure 1.Institute is functional Layer is all made of vacuum evaporation process and is made, implanted layer HAT-CN in cave therein, hole transmission layer NPB, electron transfer layer TPBI, hair Photosphere material MADN specific structure is as follows:
The beneficial effects of the present invention are:
1. the present invention constructs one kind using tetramethyl dibenzanthracene as the non-right of skeleton by certain methodology of organic synthesis Claim structural compounds molecule, i.e. compound shown in formula 1, is the originality structure having not been reported.
2. this kind of new construction of the invention has the characteristics that the nonplanar structure of suitable molecular conjugation length, height, and Molecular mass (molecular weight is up to 400-1000) appropriate, make it have good thin film stability (being not easy to crystallize), be suitble to Molecular entergy level (can allow existing each functional layer material).
3. such material of the invention is highly suitable as the luminescent layer of small molecule OLED device, it is applied to organic electroluminescence and sends out In optical arena, using such material as luminescent layer, the OLED device of production, the maximum brightness 4160-6160cd/m of device2, most High current efficiency 1.7-2.6cd/A, device efficiency are good.
4. such material of the invention has the luminescent properties of preferable blue phosphor material of main part, overall performance is obviously excellent In commercial materials mCP, same device design, lower, the maximum current efficiency that opens bright voltage of most compounds in the present invention It is higher, illustrate the prospect that this kind of material involved in the present invention has some commercial potential and further develops.
Detailed description of the invention
Fig. 1 is that the structural schematic diagram of organic electroluminescence device prepared by the present invention is followed successively by by lower layer to upper layer ITO Conducting Glass (1), hole injection layer (2), hole transmission layer (3), luminescent layer (4), electron transfer layer (5), electronics note Enter layer (6) and cathode layer (7), wherein luminescent layer (4) be related to it is of the present invention and electroluminescent organic material.
Fig. 2 is W.V.Mayneord in background of invention and specific datagram corresponding in E.M.F.Roe paper.
Specific embodiment
The principle and features of the present invention will be described below with reference to the accompanying drawings, and the given examples are served only to explain the present invention, and It is non-to be used to limit the scope of the invention.
Compound prepares embodiment:
The preparation of 1 compound C01 of embodiment
The preparation of compound 1: in 1000mL there-necked flask, 2,6- bis- bromo- 9,9,10,10- tetramethyls -9,10- bis- are added Diphenyl hydrogen and anthracene (24.7g, 0.05mol), carbazole (8.36g, 0.05mol), sodium tert-butoxide (14.4g, 0.15mol), dimethylbenzene (700mL), palladium acetate (0.122g), tri-tert phosphorus tetrafluoroborate (0.290g), N2Under protection, it is warming up to reflux, is kept the temperature 10h is reacted, room temperature is down to, 250mL deionized water is added into reaction flask, stirs 15min, liquid separation, the washing of 300mL deionized water Organic phase 3 times, collect organic phase, anhydrous Na2SO430cm thickness silicagel column, 1L eluant, eluent (toluene: petroleum ether=3:1) are crossed after drying Pillar is eluted, merged column liquid desolventizing, gained yellow solid uses toluene: petroleum ether=1:5 reflux mashing purifying, after cooling It filters and dries, obtain compound 1, faint yellow solid 20.90g, yield 72.0%, MS (m/z): 579.2.
The preparation of compound C01: according to 1 the method for embodiment (preparation of compound 1), 0.01mol compound is put into 1, obtain compound C01, faint yellow solid 4.51g, yield 61.5%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C54H40N2O, theoretical value 732.3141, test value 732.3258.Elemental analysis (C54H40N2O), theoretical value C:88.49, H:5.51, N:3.82, O:2.18, measured value C:88.47, H:5.53, N:3.83, O:2.17.
The preparation of 2 compound C02 of embodiment
The preparation of compound C02: according to 1 the method for embodiment (preparation of compound 1), 0.01mol compound is put into 1, obtain compound C02, faint yellow solid 5.38g, yield 67.3%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C59H46N2O, theoretical value 798.3610, test value 798.3422.Elemental analysis (C59H46N2O), theoretical value C:88.69, H:5.80, N:3.51, O:2.00, measured value C:88.68, H:5.78, N:3.52, O:2.02.
The preparation of 3 compound C06 of embodiment
The preparation of compound 2: according to 1 the method for embodiment (preparation of compound 1), 0.05mol 2,6- bis- are put into Bromo- 9,9,10,10- tetramethyl -9,10- dihydro-dibenzo anthracenes, obtain compound 2, faint yellow solid 23.8g, yield 75.5%, MS (m/z): 629.2.
The preparation of compound C06: it in 250mL there-necked flask, is added compound 2 (6.31g, 0.01mol), 10- phenyl- 10- hydrogen phenoxazine -2- boric acid (3.33g, 0.011mol), potassium carbonate (3g, 0.022mol), toluene (150g), ethyl alcohol (50g), Deionized water (65g) under nitrogen protection, is added Pd (OAc)2(0.025g), Sphos (0.082g), is warming up to reflux, and heat preservation is anti- 12h is answered, is cooled to 40 DEG C, liquid separation, organic phase washes primary, liquid separation with 150g water, and organic phase is dry by 50g anhydrous magnesium sulfate Afterwards, the quick silicagel column for crossing 25cm thickness crosses column liquid desolventizing and obtains faint yellow solid crude product, and crude product uses toluene: petroleum ether=1:5 Reflux mashing purifying, filters and dry after cooling, obtains compound C06, white solid 4.95g, yield 61.2%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C60H44N2O, theoretical value 808.3454, test value 808.3127.Elemental analysis (C60H44N2O), theoretical value C:89.08, H:5.48, N:3.46, O:1.98, measured value C:89.05, H:5.50, N:3.48, O:1.97.
The preparation of 4 compound C08 of embodiment
The preparation of compound C08: according to 3 the method for embodiment (preparation of compound C06), 0.01mol chemical combination is put into Object 2 obtains compound C08, faint yellow solid 4.87g, yield 56.7%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C63H46N4, theoretical value 859.0661, test value 859.2178.Elemental analysis (C63H46N4), theoretical value C:88.08, H:5.40, N:6.52, measured value C:88.05, H:5.42, N: 6.53。
The preparation of 5 compound C09 of embodiment
The preparation of compound C09: according to 3 the method for embodiment (preparation of compound C06), 0.01mol chemical combination is put into Object 2 obtains compound C09, faint yellow solid 5.34g, yield 73.4%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C56H41N, theoretical value 727.3239, test value 727.3968.Elemental analysis (C56H41N), theoretical value C:92.40, H:5.68, N:1.92, measured value C:92.38, H:5.69, N: 1.93。
The preparation of 6 compound C15 of embodiment
The preparation of compound 3: according to 1 the method for embodiment (preparation of compound 1), 0.05mol 2,6- bis- are put into Bromo- 9,9,10,10- tetramethyl -9,10- dihydro-dibenzo anthracenes, obtain compound 3, faint yellow solid 24.4g, yield 72.9%, MS (m/z): 669.2.
The preparation of compound C15: according to 1 the method for embodiment (preparation of compound 1), 0.01mol compound is put into 3, obtain compound C15, faint yellow solid 4.27g, yield 55.3%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C56H40N2O2, theoretical value 772.3090, test value 772.2598.Elemental analysis (C56H40N2O2), theoretical value C:87.02, H:5.22, N:3.62, O:4.14, measured value C:87.03, H:5.24, N:3.61, O:4.12.
The preparation of 7 compound C19 of embodiment
The preparation of compound 4: according to 3 the method for embodiment (preparation of compound C06), 0.05mol 2,6- bis- are put into Bromo- 9,9,10,10- tetramethyl -9,10- dihydro-dibenzo anthracenes, obtain compound 4, faint yellow solid 22.8g, yield 69.4%, MS (m/z): 655.2.
The preparation of compound C19: according to 1 the method for embodiment (preparation of compound 1), 0.01mol compound is put into 4, obtain compound C19, faint yellow solid 4.99g, yield 61.7%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C60H44N2O, theoretical value 808.3454, test value 808.2278.Elemental analysis (C60H44N2O), theoretical value C:89.08, H:5.48, N:3.46, O:1.98, measured value C:89.05, H:5.47, N:3.48, O:2.00.
The preparation of 8 compound C21 of embodiment
The preparation of compound C21: according to 1 the method for embodiment (preparation of compound 1), 0.01mol compound is put into 4, obtain compound C21, faint yellow solid 5.52g, yield 63.1%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C65H50N2O, theoretical value 874.3923, test value 874.4425.Elemental analysis (C65H50N2O), theoretical value C:89.21, H:5.76, N:3.20, O:1.83, measured value C:89.20, H:5.74, N:3.22, O:1.84.
The preparation of 9 compound C24 of embodiment
The preparation of compound C24: according to 3 the method for embodiment (preparation of compound C06), 0.01mol chemical combination is put into Object 4 obtains compound C24, faint yellow solid 5.29g, yield 72.5%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C56H43N2, theoretical value 729.3396, test value 729.1987.Elemental analysis (C56H43N2), theoretical value C:92.14, H:5.94, N:1.92, measured value C:92.12, H:5.95, N: 1.93。
The preparation of 10 compound C27 of embodiment
The preparation of compound 5: according to 3 the method for embodiment (preparation of compound C06), 0.05mol 2,6- bis- are put into Bromo- 9,9,10,10- tetramethyl -9,10- dihydro-dibenzo anthracenes, obtain compound 5, faint yellow solid 25.1g, yield 70.9%, MS (m/z): 705.2.
The preparation of compound C27: according to 3 the method for embodiment (preparation of compound C06), 0.01mol chemical combination is put into Object 5 obtains compound C27, faint yellow solid 5.35g, yield 67.4%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C60H43NO, theoretical value 793.3345, test value 793.3914.Elemental analysis (C60H43NO), theoretical value C:90.76, H:5.46, N:1.76, O:2.02, measured value C:90.73, H:5.47, N:1.77, O:2.03.
The preparation of 11 compound C29 of embodiment
The preparation of compound 6: according to 1 the method for embodiment (preparation of compound 1), 0.05mol 2,6- bis- are put into Bromo- 9,9,10,10- tetramethyl -9,10- dihydro-dibenzo anthracenes, obtain compound 6, faint yellow solid 19.5g, yield 66.8%, MS (m/z): 581.2.
The preparation of compound C29: according to 1 the method for embodiment (preparation of compound 1), 0.01mol compound is put into 6, obtain compound C29, faint yellow solid 4.83g, yield 65.7%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C54H42N2O, theoretical value 734.3297, test value 734.1563.Elemental analysis (C54H42N2O), theoretical value C:88.25, H:5.76, N:3.81, O:2.18, measured value C:88.22, H:5.77, N:3.82, O:2.19.
The preparation of 12 compound C30 of embodiment
The preparation of compound C30: according to 1 the method for embodiment (preparation of compound 1), 0.01mol compound is put into 6, obtain compound C30, faint yellow solid 4.97g, yield 62.0%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C59H48N2O, theoretical value 800.3767, test value 800.2265.Elemental analysis (C59H48N2O), theoretical value C:88.47, H:6.03, N:3.50, O:2.00, measured value C:88.45, H:6.02, N:3.52, O:2.01.
The preparation of 13 compound C32 of embodiment
The preparation of compound C32: according to 3 the method for embodiment (preparation of compound C06), 0.01mol chemical combination is put into Object 6 obtains compound C32, faint yellow solid 5.85g, yield 72.1%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C59H46N4, theoretical value 810.3722, test value 810.2945.Elemental analysis (C59H46N4), theoretical value C:87.37, H:5.72, N:6.91, measured value C:87.34, H:5.73, N: 6.93。
The preparation of 14 compound C37 of embodiment
The preparation of compound 7: according to 1 the method for embodiment (preparation of compound 1), 0.05mol 2,6- bis- are put into Bromo- 9,9,10,10- tetramethyl -9,10- dihydro-dibenzo anthracenes, obtain compound 7, faint yellow solid 21.3g, yield 67.3%, MS (m/z): 631.2.
The preparation of compound C37: according to 3 the method for embodiment (preparation of compound C06), 0.01mol chemical combination is put into Object 7 obtains compound C37, faint yellow solid 5.12g, yield 63.9%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C60H46N2O, theoretical value 810.3610, test value 810.3450.Elemental analysis (C60H46N2O), theoretical value C:88.86, H:5.72, N:3.45, O:1.97, measured value C:88.85, H:5.73, N:3.44, O:1.98.
The preparation of 15 compound C40 of embodiment
The preparation of compound 8: according to 1 the method for embodiment (preparation of compound 1), 0.05mol 2,6- bis- are put into Bromo- 9,9,10,10- tetramethyl -9,10- dihydro-dibenzo anthracenes, obtain compound 8, faint yellow solid 24.3g, yield 66.1%, MS (m/z): 733.2.
The preparation of compound C40: according to 3 the method for embodiment (preparation of compound C06), 0.01mol chemical combination is put into Object 8 obtains compound C40, faint yellow solid 6.23g, yield 69.4%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C68H51NO, theoretical value 897.3971, test value 897.4531.Elemental analysis (C68H51NO), theoretical value C:90.94, H:5.72, N:1.56, N:1.78, measured value C:90.92, H:5.74, N:1.57, N:1.77.
The preparation of 16 compound C43 of embodiment
The preparation of compound 9: according to 3 the method for embodiment (preparation of compound C06), 0.05mol 2,6- bis- are put into Bromo- 9,9,10,10- tetramethyl -9,10- dihydro-dibenzo anthracenes, obtain compound 9, faint yellow solid 24.1g, yield 73.2%, MS (m/z): 657.2.
The preparation of compound C43: according to 1 the method for embodiment (preparation of compound 1), 0.01mol compound is put into 9, obtain compound C43, faint yellow solid 6.26g, yield 71.4%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C65H52N2O, theoretical value 876.4080, test value 876.4772.Elemental analysis (C65H52N2O), theoretical value C:89.01, H:5.98, N:3.19, N:1.82, measured value C:89.02, H:5.97, N:3.18, N:1.83.
The preparation of 17 compound C46 of embodiment
The preparation of compound 10: according to 1 the method for embodiment (preparation of compound 1), 0.05mol 2,6- bis- are put into Bromo- 9,9,10,10- tetramethyl -9,10- dihydro-dibenzo anthracenes, obtain compound 10, faint yellow solid 25.2g, yield 68.5%, MS (m/z): 733.2.
The preparation of compound C46: according to 1 the method for embodiment (preparation of compound 1), 0.01mol compound is put into 10, obtain compound C46, faint yellow solid 6.99g, yield 73.3%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C71H56N2O, theoretical value 952.4393, test value 952.2781.Elemental analysis (C71H56N2O), theoretical value C:89.46, H:5.92, N:2.94, N:1.68, measured value C:89.44, H:5.91, N:2.96, N:1.69.
The preparation of 18 compound C50 of embodiment
The preparation of compound 11: according to 1 the method for embodiment (preparation of compound 1), 0.05mol 2,6- bis- are put into Bromo- 9,9,10,10- tetramethyl -9,10- dihydro-dibenzo anthracenes, obtain compound 11, faint yellow solid 15.5g, yield 42.1%, MS (m/z): 735.2.
The preparation of compound C50: according to 3 the method for embodiment (preparation of compound C06), 0.01mol chemical combination is put into Object 11 obtains compound C50, faint yellow solid 4.09g, yield 44.7%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C66H50N4O, theoretical value 914.3985, test value 914.1178.Elemental analysis (C66H50N4O), theoretical value C:86.62, H:5.51, N:6.12, N:1.75, measured value C:86.64, H:5.49, N:6.11, N:1.76.
The preparation of 19 compound C54 of embodiment
The preparation of compound 12: according to 1 the method for embodiment (preparation of compound 1), 0.05mol 2,6- bis- are put into Bromo- 9,9,10,10- tetramethyl -9,10- dihydro-dibenzo anthracenes, obtain compound 12, faint yellow solid 25.6g, yield 71.5%, MS (m/z): 713.2.
The preparation of compound C54: according to 1 the method for embodiment (preparation of compound 1), 0.01mol compound is put into 12, obtain compound C54, faint yellow solid 6.09g, yield 65.3%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C68H56N2O2, theoretical value 932.4342, test value 932.2765.Elemental analysis (C68H56N2O2), theoretical value C:87.52, H:6.05, N:3.00, N:3.43, measured value C:87.50, H:6.07, N:3.01, N:3.42.
The preparation of 20 compound C56 of embodiment
The preparation of compound C56: according to 3 the method for embodiment (preparation of compound C06), 0.01mol chemical combination is put into Object 12 obtains compound C56, faint yellow solid 4.74g, yield 57.2%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C62H53NO, theoretical value 827.4127, test value 827.4332.Elemental analysis (C62H53NO), theoretical value C:89.93, H:6.45, N:1.69, N:1.93, measured value C:89.95, H:6.43, N:1.68, N:1.94.
Organic electroluminescence device embodiment:
The present invention chooses compound C02, compound C08, compound C09, compound C15, compound C19, compound C21, compound C30, compound C32, compound C40, compound C54 make organic electroluminescence as emitting layer material Part, it should be understood that device implementation process with as a result, being intended merely to preferably explain the present invention, not limitation of the present invention.
Application of the 21 compound C02 of embodiment in organic electroluminescence device
The present embodiment prepares organic electroluminescence device one by the following method:
A) it cleans ITO (tin indium oxide) glass: cleaning each 25 points of ito glass with deionized water, acetone, EtOH Sonicate respectively Then clock is handled 15 minutes in plasma cleaner；
B) the vacuum evaporation hole injection layer HAT-CN on anode ito glass, with a thickness of 10nm；
C) the vacuum evaporation hole transmission layer NPB on hole injection layer, with a thickness of 40nm；
D) on hole transmission layer NPB, vacuum mixing vapor deposition luminescent layer compound C02:MADN=9:1 (W/W), thickness For 30nm；
E) on luminescent layer, vacuum evaporation electron transfer layer TPBI, with a thickness of 30nm；
F) on electron transfer layer, vacuum evaporation electron injecting layer LiF, with a thickness of 1nm；
G) on electron injecting layer, vacuum evaporation cathode Al, with a thickness of 100nm.
The structure of device one is ITO/HAT-CN (10nm)/NPB (40nm)/compound C02:MADN=9:1 (W/W) (30nm)/TPBI (30nm)/LiF (1nm)/Al (100nm), during vacuum evaporation, pressure < 1.0 × 10-3Pa, device one The photooptical datas such as bright voltage, maximum current efficiency, excitation purity are opened to be listed in table 1 hereinafter.
Application of the 30 compound C08- compound C54 of embodiment 22- embodiment in organic electroluminescence device
Respectively with compound C08, compound C09, compound C15, compound C19, compound C21, compound C30, change It closes object C32, compound C40, compound C54 and replaces compound C02, according to 21 the method for embodiment, make organic electroluminescence hair Optical device two is to device ten, device two to the structure of device ten, respectively ITO/HAT-CN (10nm)/NPB (40nm)/(chemical combination Object C08- compound C54): MADN=9:1 (W/W) (30nm)/TPBI (30nm)/LiF (1nm)/Al (100nm), device two to Device ten to open the photooptical datas such as bright voltage, maximum current efficiency, excitation purity as shown in table 1 below.
Application of the 31 contrast material mCP of embodiment in organic electroluminescence device
Organic electroluminescence hair is made according to 21 the method for embodiment so that material of main part mCP is commercialized instead of compound C02 Optical device 11, structure are ITO/HAT-CN (10nm)/NPB (40nm)/mCP:MADN=9:1 (W/W) (30nm)/TPBI (30nm)/LiF (1nm)/Al (100nm), device 11 open the photooptical datas such as bright voltage, maximum current efficiency, excitation purity such as Shown in the following table 1.
Implanted layer HAT-CN in cave therein, hole transmission layer NPB, electron transfer layer TPBI, emitting layer material MADN and mCP Specific structure is as follows:
1 device one of table to device 11 photooptical data table
Such material involved in the present invention has preferable luminescent properties, is optimized by device architecture, can be obviously improved The photoelectric properties of organic electroluminescence devices and its service life, with some commercial potential and the prospect further developed.
The foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, it is all in spirit of the invention and Within principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.

Claims (3)

1. a kind of unsymmetric structure electroluminescent organic material, which is characterized in that including the chemical combination with molecular structure shown in formula 1 Object:
Wherein, X1For any one in following group:
X2For any one in following group:
2. one kind unsymmetric structure electroluminescent organic material according to claim 1, which is characterized in that described asymmetric The concrete structure formula of structure electroluminescent organic material is one of following C01-C56 or a variety of:
3. the application of a kind of unsymmetric structure electroluminescent organic material, in organic electroluminescence device, at least one function Ergosphere contains such as the described in any item unsymmetric structure electroluminescent organic materials of claim 1-2.
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