CN106188026A - One class unsymmetric structure electroluminescent organic material and application thereof - Google Patents

One class unsymmetric structure electroluminescent organic material and application thereof Download PDF

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CN106188026A
CN106188026A CN201610518886.8A CN201610518886A CN106188026A CN 106188026 A CN106188026 A CN 106188026A CN 201610518886 A CN201610518886 A CN 201610518886A CN 106188026 A CN106188026 A CN 106188026A
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organic material
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CN106188026B (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 class unsymmetric structure electroluminescent organic material and an application thereof, belong to organic photoelectrical material technical field.It compound including there is molecular structure as follows:Wherein, X1For any one in carbazole and deriveding group, two aromatic amine groups, X2For any one in phenoxazine and deriveding group, dibenzofurans and deriveding group thereof, triazine ring deriveding group, aromatic group.This kind of new construction of the present invention has suitable molecular conjugation length, the nonplanar structure feature of height, and suitable molecular mass so that it is have good thin film stability, applicable molecular entergy level.Such material of the present 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 in hgher efficiency, illustrates that this kind of material involved in the present invention has some commercial potential and the prospect of exploitation further.

Description

One class unsymmetric structure electroluminescent organic material and application thereof
Technical field
The present invention relates to class unsymmetric structure electroluminescent organic material and an application thereof, belong to organic photoelectrical material technology Field.
Background technology
Pope et al. is found that the Electroluminescence Properties of monocrystalline anthracene first in nineteen sixty-five, and this is the first electricity of organic compound Photoluminescence phenomenon, through development for many years, organic electroluminescence device both can be used to manufacture novel display product, it is possible to For making novel illumination product, it is expected to replace available liquid crystal and shows and fluorescent lighting.
At present, commodity based on OLED Display Technique, have been carried out industrialization.Compared with liquid crystal type Display Technique, OLED Display Technique have self-luminous, radiationless, light weight, thickness are thin, wide viewing angle, wide colour gamut, colour stable, fast response time, ring Border adapts to by force, can realize the plurality of advantages such as Flexible Displays, and therefore, OLED Display Technique is obtaining people and more and more paying close attention to With corresponding Technical investment.
As far back as nineteen thirty-seven, from two scholar W.V.Mayneord and E.M.F.Roe being engaged in cancer research in London, send out One, table is about the paper of the ultra-violet absorption spectrum feature of complicated aryl radical compound, and this paper carried out multiple aromatization The test of the ultra-violet absorption spectrum data of compound and contrast, wherein describe a kind of compound 9,9,10,10-tetramethyl- 9,10-dihydro-dibenzo anthracenes, it has a characteristic ultraviolet absorption similar to naphthalene nucleus, but the two molecular structure significant difference, article The most specifically data are as shown in Figure 2:
According to the data of Fig. 2, it may be speculated that 9,9,10,10-tetramethyl-9,10-dihydro-dibenzo anthracene center ring 9,10 Reach saturation simultaneously, weaken or intercepted the two-part molecular conjugation in left and right, cause it to show similar and single naphthalene The spectral absorption characteristics of loop section.But this structure is the most dramatically different with naphthalene nucleus, there is more preferable stereoeffect, as Fruit introduces different carbazoles, aromatic amine, phenoxazine class, dibenzofurans class, triazines, very at the avtive spot of its structure To aromatics structure, increase its both sides conjugate length, obtained series compound to some extent, there is the application of OLED field Prospect.
Summary of the invention
An object of the present invention, is to provide a class unsymmetric structure electroluminescent organic material.The Organic Electricity of the present invention Electroluminescent material, has higher vitrification point, suitable HOMO energy level and lumo energy, wider energy gap and suitable S1 Energy level.
The technical scheme is that a class unsymmetric structure electroluminescent organic material, Including having the compound of molecular structure shown in formula 1:
Wherein, X1For any one in carbazole and deriveding group, two aromatic amine groups, X2For phenoxazine and derivative Any one in group, dibenzofurans and deriveding group thereof, triazine ring deriveding group, aromatic group.
The compound of the present invention unsymmetric structure with tetramethyl dibenzanthracene as skeleton, i.e. compound shown in formula 1, has Higher vitrification point, suitable HOMO energy level and lumo energy, wider energy gap；Such material can be organic as little 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 life-span thereof.
On the basis of technique scheme, the present invention can also do following improvement.
Further, described X1For any one in following group:
Above-mentioned further scheme is used to provide the benefit that: to obtain more suitably molecular size, nonplanar space and stood Body structure and suitably molecular entergy level distribution.
Further, described X2For any one in following group:
Above-mentioned further scheme is used to provide the benefit that: to obtain more suitably molecular size, nonplanar space and stood Body structure and suitably molecular entergy level distribution.
Further, the concrete structure formula of described unsymmetric structure electroluminescent organic material is in following C01-C56 Plant or multiple:
Above-mentioned further scheme is used to provide the benefit that: to calculate HOMO and lumo energy, S1 energy level through molecular simulation, Can arrange in pairs or groups existing finished commercial prod material, and they are by late device evaluation test, it is thus identified that excellent photoelectric properties.
The two of the purpose of the present invention, are to provide the application of above-mentioned unsymmetric structure electroluminescent organic material.
The technical scheme is that a class unsymmetric structure electroluminescent organic material Application, in prepared organic electroluminescence device, at least a functional layer contains unsymmetric structure as above has Electroluminescent material.
Prepared organic electroluminescence device generally comprises ITO Conducting Glass (anode), the hole being sequentially overlapped Implanted layer, hole transmission layer (NPB), luminescent layer (material in the present invention or DPVBi), electron transfer layer (TPBI), electronics are noted Enter layer (LiF) and cathode layer (Al).The structural representation of prepared organic electroluminescence device is as shown in Figure 1.All functions Layer all use vacuum evaporation process make, cave implanted layer HAT-CN therein, hole transmission layer NPB, electron transfer layer TPBI, send out Light layer material MADN concrete structure is as follows:
The invention has the beneficial effects as follows:
1. the present invention is by certain methodology of organic synthesis, constructs non-right with tetramethyl dibenzanthracene as skeleton of a class Claiming structural compounds molecule, i.e. compound shown in formula 1, is the originality structure having no report.
2. this kind of new construction of the present invention has suitable molecular conjugation length, the nonplanar structure feature of height, and Suitable molecular mass (molecular weight is up to 400-1000) so that it is there is good thin film stability (being difficult to crystallization), be suitable for Molecular entergy level (existing each functional layer material of can arranging in pairs or groups).
3. such material of the present invention is highly suitable as the luminescent layer of small molecule OLED device, is applied to organic electroluminescence and sends out In optical arena, using such material as luminescent layer, the OLED of making, high-high brightness 4160-6160cd/m of device2, Big current efficiency 1.7-2.6cd/A, device efficiency is good.
4. such material of the present invention has the luminescent properties of preferable blue phosphor material of main part, and overall performance is the most excellent In commercial materials mCP, same device design, in the present invention most compounds to open bright voltage lower, maximum current efficiency Higher, illustrate that this kind of material involved in the present invention has some commercial potential and the prospect of exploitation further.
Accompanying drawing explanation
Fig. 1 is the structural representation of the organic electroluminescence device prepared by the present invention, by lower floor to upper strata, is followed successively by ITO Conducting Glass (1), hole injection layer (2), hole transmission layer (3), luminescent layer (4), electron transfer layer (5), electronics are noted Enter layer (6) and cathode layer (7), wherein luminescent layer (4) relate to of the present invention and electroluminescent organic material.
Fig. 2 is corresponding concrete datagram in W.V.Mayneord to E.M.F.Roe paper in background of invention.
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.
Compound prepares embodiment:
The preparation of embodiment 1 compound C01
The preparation of compound 1: in 1000mL there-necked flask, addition 2, bromo-9,9,10,10-tetramethyl-9 of 6-bis-, 10-bis- Diphenyl hydrogen anthracene (24.7g, 0.05mol), carbazole (8.36g, 0.05mol), sodium tert-butoxide (14.4g, 0.15mol), dimethylbenzene (700mL), palladium (0.122g), tri-tert phosphorus tetrafluoroborate (0.290g), N2Under protection, it is warming up to backflow, insulation Reaction 10h, is down to room temperature, adds 250mL deionized water, stir 15min, separatory, 300mL deionized water wash in reaction bulb Organic facies 3 times, collects organic facies, anhydrous Na2SO4Cross 30cm thickness silicagel column, 1L eluant (toluene: petroleum ether=3:1) after drying Drip washing pillar, merged post loss of thick fluid solvent, gained yellow solid use toluene: petroleum ether=1:5 backflow making beating purification, after cooling Sucking filtration is also dried, and obtains compound 1, faint yellow solid 20.90g, yield 72.0%, and MS (m/z): 579.2.
The preparation of compound C01: according to method described in embodiment 1 (preparation of compound 1), puts into 0.01mol compound 1, obtain compound C01, faint yellow solid 4.51g, yield 61.5%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C54H40N2O, theoretical value 732.3141, test value 732.3258.Elementary 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 embodiment 2 compound C02
The preparation of compound C02: according to method described in embodiment 1 (preparation of compound 1), puts into 0.01mol compound 1, obtain compound C02, faint yellow solid 5.38g, yield 67.3%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C59H46N2O, theoretical value 798.3610, test value 798.3422.Elementary 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 embodiment 3 compound C06
The preparation of compound 2: according to method described in embodiment 1 (preparation of compound 1), puts into 0.05mol 2,6-bis- Bromo-9,9,10,10-tetramethyl-9,10-dihydro-dibenzo anthracene, obtain compound 2, faint yellow solid 23.8g, yield 75.5%, MS (m/z): 629.2.
The preparation of compound C06: in 250mL there-necked flask, addition 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), ethanol (50g), Deionized water (65g), under nitrogen protection, adds Pd (OAc)2(0.025g), Sphos (0.082g), be warming up to backflow, insulation is anti- Answering 12h, be cooled to 40 DEG C, separatory, with the washing of 150g water once, separatory, organic facies is dried organic facies through 50g anhydrous magnesium sulfate After, the quick silicagel column crossing 25cm thickness, cross post loss of thick fluid solvent and obtain faint yellow solid crude product, crude product use toluene: petroleum ether=1:5 Backflow making beating purification, sucking filtration being dried after cooling, obtain compound C06, white solid 4.95g, yield 61.2%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C60H44N2O, theoretical value 808.3454, test value 808.3127.Elementary 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 embodiment 4 compound C08
The preparation of compound C08: according to method described in embodiment 3 (preparation of compound C06), puts into 0.01mol chemical combination Thing 2, obtains compound C08, faint yellow solid 4.87g, yield 56.7%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C63H46N4, theoretical value 859.0661, test value 859.2178.Elementary 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 embodiment 5 compound C09
The preparation of compound C09: according to method described in embodiment 3 (preparation of compound C06), puts into 0.01mol chemical combination Thing 2, obtains compound C09, faint yellow solid 5.34g, yield 73.4%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C56H41N, theoretical value 727.3239, test value 727.3968.Elementary 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 embodiment 6 compound C15
The preparation of compound 3: according to method described in embodiment 1 (preparation of compound 1), puts into 0.05mol 2,6-bis- Bromo-9,9,10,10-tetramethyl-9,10-dihydro-dibenzo anthracene, obtain compound 3, faint yellow solid 24.4g, yield 72.9%, MS (m/z): 669.2.
The preparation of compound C15: according to method described in embodiment 1 (preparation of compound 1), puts into 0.01mol compound 3, obtain compound C15, faint yellow solid 4.27g, yield 55.3%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C56H40N2O2, theoretical value 772.3090, test value 772.2598.Elementary 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 embodiment 7 compound C19
The preparation of compound 4: according to method described in embodiment 3 (preparation of compound C06), puts into 0.05mol 2,6-bis- Bromo-9,9,10,10-tetramethyl-9,10-dihydro-dibenzo anthracene, obtain compound 4, faint yellow solid 22.8g, yield 69.4%, MS (m/z): 655.2.
The preparation of compound C19: according to method described in embodiment 1 (preparation of compound 1), puts into 0.01mol compound 4, obtain compound C19, faint yellow solid 4.99g, yield 61.7%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C60H44N2O, theoretical value 808.3454, test value 808.2278.Elementary 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 embodiment 8 compound C21
The preparation of compound C21: according to method described in embodiment 1 (preparation of compound 1), puts into 0.01mol compound 4, obtain compound C21, faint yellow solid 5.52g, yield 63.1%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C65H50N2O, theoretical value 874.3923, test value 874.4425.Elementary 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 embodiment 9 compound C24
The preparation of compound C24: according to method described in embodiment 3 (preparation of compound C06), puts into 0.01mol chemical combination Thing 4, obtains compound C24, faint yellow solid 5.29g, yield 72.5%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C56H43N2, theoretical value 729.3396, test value 729.1987.Elementary 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 embodiment 10 compound C27
The preparation of compound 5: according to method described in embodiment 3 (preparation of compound C06), puts into 0.05mol 2,6-bis- Bromo-9,9,10,10-tetramethyl-9,10-dihydro-dibenzo anthracene, obtain compound 5, faint yellow solid 25.1g, yield 70.9%, MS (m/z): 705.2.
The preparation of compound C27: according to method described in embodiment 3 (preparation of compound C06), puts into 0.01mol chemical combination Thing 5, obtains compound C27, faint yellow solid 5.35g, yield 67.4%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C60H43NO, theoretical value 793.3345, test value 793.3914.Elementary 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 embodiment 11 compound C29
The preparation of compound 6: according to method described in embodiment 1 (preparation of compound 1), puts into 0.05mol 2,6-bis- Bromo-9,9,10,10-tetramethyl-9,10-dihydro-dibenzo anthracene, obtain compound 6, faint yellow solid 19.5g, yield 66.8%, MS (m/z): 581.2.
The preparation of compound C29: according to method described in embodiment 1 (preparation of compound 1), puts into 0.01mol compound 6, obtain compound C29, faint yellow solid 4.83g, yield 65.7%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C54H42N2O, theoretical value 734.3297, test value 734.1563.Elementary 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 embodiment 12 compound C30
The preparation of compound C30: according to method described in embodiment 1 (preparation of compound 1), puts into 0.01mol compound 6, obtain compound C30, faint yellow solid 4.97g, yield 62.0%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C59H48N2O, theoretical value 800.3767, test value 800.2265.Elementary 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 embodiment 13 compound C32
The preparation of compound C32: according to method described in embodiment 3 (preparation of compound C06), puts into 0.01mol chemical combination Thing 6, obtains compound C32, faint yellow solid 5.85g, yield 72.1%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C59H46N4, theoretical value 810.3722, test value 810.2945.Elementary 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 embodiment 14 compound C37
The preparation of compound 7: according to method described in embodiment 1 (preparation of compound 1), puts into 0.05mol 2,6-bis- Bromo-9,9,10,10-tetramethyl-9,10-dihydro-dibenzo anthracene, obtain compound 7, faint yellow solid 21.3g, yield 67.3%, MS (m/z): 631.2.
The preparation of compound C37: according to method described in embodiment 3 (preparation of compound C06), puts into 0.01mol chemical combination Thing 7, obtains compound C37, faint yellow solid 5.12g, yield 63.9%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C60H46N2O, theoretical value 810.3610, test value 810.3450.Elementary 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 embodiment 15 compound C40
The preparation of compound 8: according to method described in embodiment 1 (preparation of compound 1), puts into 0.05mol 2,6-bis- Bromo-9,9,10,10-tetramethyl-9,10-dihydro-dibenzo anthracene, obtain compound 8, faint yellow solid 24.3g, yield 66.1%, MS (m/z): 733.2.
The preparation of compound C40: according to method described in embodiment 3 (preparation of compound C06), puts into 0.01mol chemical combination Thing 8, obtains compound C40, faint yellow solid 6.23g, yield 69.4%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C68H51NO, theoretical value 897.3971, test value 897.4531.Elementary 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 embodiment 16 compound C43
The preparation of compound 9: according to method described in embodiment 3 (preparation of compound C06), puts into 0.05mol 2,6-bis- Bromo-9,9,10,10-tetramethyl-9,10-dihydro-dibenzo anthracene, obtain compound 9, faint yellow solid 24.1g, yield 73.2%, MS (m/z): 657.2.
The preparation of compound C43: according to method described in embodiment 1 (preparation of compound 1), puts into 0.01mol compound 9, obtain compound C43, faint yellow solid 6.26g, yield 71.4%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C65H52N2O, theoretical value 876.4080, test value 876.4772.Elementary 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 embodiment 17 compound C46
The preparation of compound 10: according to method described in embodiment 1 (preparation of compound 1), puts into 0.05mol 2,6-bis- Bromo-9,9,10,10-tetramethyl-9,10-dihydro-dibenzo anthracene, obtain compound 10, faint yellow solid 25.2g, yield 68.5%, MS (m/z): 733.2.
The preparation of compound C46: according to method described in embodiment 1 (preparation of compound 1), puts into 0.01mol compound 10, obtain compound C46, faint yellow solid 6.99g, yield 73.3%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C71H56N2O, theoretical value 952.4393, test value 952.2781.Elementary 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 embodiment 18 compound C50
The preparation of compound 11: according to method described in embodiment 1 (preparation of compound 1), puts into 0.05mol 2,6-bis- Bromo-9,9,10,10-tetramethyl-9,10-dihydro-dibenzo anthracene, obtain compound 11, faint yellow solid 15.5g, yield 42.1%, MS (m/z): 735.2.
The preparation of compound C50: according to method described in embodiment 3 (preparation of compound C06), puts into 0.01mol chemical combination Thing 11, obtains compound C50, faint yellow solid 4.09g, yield 44.7%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C66H50N4O, theoretical value 914.3985, test value 914.1178.Elementary 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 embodiment 19 compound C54
The preparation of compound 12: according to method described in embodiment 1 (preparation of compound 1), puts into 0.05mol 2,6-bis- Bromo-9,9,10,10-tetramethyl-9,10-dihydro-dibenzo anthracene, obtain compound 12, faint yellow solid 25.6g, yield 71.5%, MS (m/z): 713.2.
The preparation of compound C54: according to method described in embodiment 1 (preparation of compound 1), puts into 0.01mol compound 12, obtain compound C54, faint yellow solid 6.09g, yield 65.3%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C68H56N2O2, theoretical value 932.4342, test value 932.2765.Elementary 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 embodiment 20 compound C56
The preparation of compound C56: according to method described in embodiment 3 (preparation of compound C06), puts into 0.01mol chemical combination Thing 12, obtains compound C56, faint yellow solid 4.74g, yield 57.2%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C62H53NO, theoretical value 827.4127, test value 827.4332.Elementary 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, as emitting layer material, make organic electroluminescence Part, it will be appreciated that device implementation process and result, is intended merely to preferably explain the present invention, not limitation of the present invention.
Embodiment 21 compound C02 application in organic electroluminescence device
The present embodiment prepares organic electroluminescence device one by the following method:
A) ITO (tin indium oxide) glass is cleaned: clean each 25 points of ito glass with deionized water, acetone, EtOH Sonicate respectively Clock, then processes 15 minutes in plasma cleaner；
B) vacuum evaporation hole injection layer HAT-CN on anode ito glass, thickness is 10nm；
C) vacuum evaporation hole transmission layer NPB on hole injection layer, thickness is 40nm；
D) on hole transmission layer NPB, vacuum mixing evaporation luminescent layer compound C02:MADN=9:1 (W/W) is thick Degree is 30nm；
E) on luminescent layer, vacuum evaporation electron transfer layer TPBI, thickness is 30nm；
F) on electron transfer layer, vacuum evaporation electron injecting layer LiF, thickness is 1nm；
G) on electron injecting layer, vacuum evaporation negative electrode Al, thickness is 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 Open the photooptical datas such as bright voltage, maximum current efficiency, excitation to be listed in hereinafter in table 1.
Embodiment 22-embodiment 30 compound C08-compound C54 application in organic electroluminescence device
Respectively with compound C08, compound C09, compound C15, compound C19, compound C21, compound C30, change Compound C32, compound C40, compound C54 replace compound C02, according to method described in embodiment 21, make organic electroluminescence and send out Optical device two to device ten, the structure of device two to device ten, respectively ITO/HAT-CN (10nm)/NPB (40nm)/(chemical combination Thing 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 as shown in table 1 below.
Embodiment 31 contrast material mCP application in organic electroluminescence device
Replace compound C02 with commercialization material of main part mCP, according to method described in embodiment 21, make organic electroluminescence and send out Optical device 11, its structure is 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 such as Shown in table 1 below.
Cave implanted layer HAT-CN therein, hole transmission layer NPB, electron transfer layer TPBI, emitting layer material MADN and mCP Concrete structure is as follows:
The photooptical data table of table 1 device one to device 11
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 life-span thereof, there is some commercial potential and the prospect of exploitation further.
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 (5)

1. a class unsymmetric structure electroluminescent organic material, it is characterised in that include having the chemical combination of molecular structure shown in formula 1 Thing:
Wherein, X1For any one in carbazole and deriveding group, two aromatic amine groups, X2For phenoxazine and deriveding group thereof, Any one in dibenzofurans and deriveding group, triazine ring deriveding group, aromatic group.
A class unsymmetric structure electroluminescent organic material the most according to claim 1, it is characterised in that described X1For with Any one in lower group:
A class unsymmetric structure electroluminescent organic material the most according to claim 1, it is characterised in that described X2For with Any one in lower group:
4. according to the class unsymmetric structure electroluminescent organic material described in any one of claim 1-3, it is characterised in that institute The concrete structure formula stating unsymmetric structure electroluminescent organic material is one or more in following C01-C56:
5. the application of a class unsymmetric structure electroluminescent organic material, in organic electroluminescence device, an at least merit Ergosphere contains the unsymmetric structure electroluminescent organic material as described in any one of claim 1-3.
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Denomination of invention: A class of asymmetric organic electroluminescent materials and their applications

Effective date of registration: 20211202

Granted publication date: 20190326

Pledgee: Yantai Branch of China Merchants Bank Co.,Ltd.

Pledgor: VALIANT Co.,Ltd.

Registration number: Y2021980013807

PC01 Cancellation of the registration of the contract for pledge of patent right
PC01 Cancellation of the registration of the contract for pledge of patent right

Date of cancellation: 20220823

Granted publication date: 20190326

Pledgee: Yantai Branch of China Merchants Bank Co.,Ltd.

Pledgor: VALIANT Co.,Ltd.

Registration number: Y2021980013807