CN105936821A - Bisindenophenoxazine organic electroluminescence materials and application thereof - Google Patents

Bisindenophenoxazine organic electroluminescence materials and application thereof Download PDF

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CN105936821A
CN105936821A CN201610289170.5A CN201610289170A CN105936821A CN 105936821 A CN105936821 A CN 105936821A CN 201610289170 A CN201610289170 A CN 201610289170A CN 105936821 A CN105936821 A CN 105936821A
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高树坤
王正
盛磊
张鑫鑫
胡葆华
燕移寒
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Valiant Co Ltd
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Abstract

The invention discloses bisindenophenoxazine organic electroluminescence materials and an application thereof, and belongs to the technical field of organic photoelectric materials. The bisindenophenoxazine organic electroluminescence materials have a molecular structure represented by formula 1 shown in the description; and in the formula 1, R1, R2, R3 and R4 are same, R1, R2, R3 and R4 are an alkyl group or an aromatic substituent group, and R5 is one of an alkyl group, an aromatic substituent group, a nitrogen-containing heterocyclic group or an oxygen-containing heterocyclic group. The invention also discloses an application of the bisindenophenoxazine organic electroluminescence materials. The materials have the characteristics of electron richness, non-planar structure, proper molecular mass, good film stability and suitable energy level. The materials can be applied to the organic electroluminescence field as a micro-molecular OLED device luminescence layer.

Description

The double indeno phenoxazine electroluminescent organic material of one class and application thereof
Technical field
The present invention relates to the double indeno phenoxazine electroluminescent organic material of a class and application thereof, belong to organic photoelectrical material skill Art 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；And Tang of Kodak et al. was prepared for for the first time in 1987 a kind of being possessed point by what organic material was formed From the organic luminescent device of functional layer, even if the latter is still provided that 1000cd/cm under 10V or more low-voltage2Above is highlighted Degree.Through development for many years, organic electroluminescence device both can be used to manufacture novel display product, it is also possible to is used for making Make novel illumination product, be expected to replace available liquid crystal and show 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.
OLED is divided into small molecule devices and macromolecule device two kinds, and wherein, small molecule devices has sandwich style more Sandwich structure, various different types of functional layers, in a certain order, with the form of solid amorphous thin film, be produced Between two electrodes, this is the grown form of small molecule OLED device.
The electroluminescent organic material being applied to OLED can be divided into two big classes from purposes: electric charge injects transmission material Material, luminescent material.Further, it is also possible to inject charge into transmission material be divided into electronics inject transmission material, electron-blocking materials, Transmission material, hole barrier materials are injected in hole；Luminescent material can also be divided into main body luminescent material, dopant material.
Phenoxazine is the aromatic heterocycle structure of the class nitrogen-atoms that contains electron rich and oxygen atom.High electricity due to phenoxazine Sub-enrichment degree, containing phenoxazine primitive and phenoxazine and the material of ring derived structure be often especially advantageous for the injection in hole with Transmission, the most this kind of material is also considered as the extraordinary structural motif that can reduce luminescent material ionization potential of a class. And, phenoxazine molecule has nonplanar structure, is markedly different from the carbazole molecules of plane, the structure energy of this nonplanarity The enough formation stoping π key gathering and the intermolecular exciplex causing device quantum efficiencies to reduce.
For above-mentioned industry background and technology growth requirement, the applicant provides a kind of containing with double indeno phenoxazines being The compound-material of framing structure and the application in OLED field thereof.Involved in the present invention ties with double indeno phenoxazines for skeleton The compound of structure has higher vitrification point and molecule heat stability, suitable HOMO energy level and lumo energy, higher Eg (swashs the energy difference of state and excited state, i.e. energy gap), is optimized by device architecture, can be obviously improved organic electroluminescence device Photoelectric properties and life-span thereof.
Summary of the invention
An object of the present invention, is to provide the class organic electroluminescence material with double indeno phenoxazines as framing structure Material.The material of the present invention can be applied in field of organic electroluminescence as the functional layer of little molecule organic electroluminescent device In.
The technical scheme is that the double indeno phenoxazine organic electroluminescence material of a class Material, has a molecular structure shown in formula 1:
Wherein, R1、R2、R3、R4The most identical, for alkyl or aromatic substituents, R5For alkyl, aromatic substituents, nitrogenous One in heterocycle or oxygen heterocycle.
The material of the present invention has electron rich, nonplanar structure feature, and suitable molecular mass, has good Thin film stability, applicable molecular entergy level.Therefore, the material of the present invention can be as the luminescent layer of small molecule OLED device, should In field of organic electroluminescence.
On the basis of technique scheme, the present invention can also do following improvement.
Further, described R1、R2、R3、R4For methyl, ethyl, phenyl, 4-fluorophenyl or 4-cyanophenyl.
Use and above-mentioned further provide the benefit that: the conjugation effect that phenoxazine ring is overall can be strengthened, allow whole molecule Conjugation scope some larger.
Further, described R5One in following substituted radical:
Use and above-mentioned further provide the benefit that: it is big that above structure can make overall molecule have the molecule being more suitable for Little, space structure, and then form the distribution of suitable molecular entergy level, and be conducive to the vitrification point improving compound and molecule heat Stability.
Double indeno phenoxazine electroluminescent organic materials of the present invention, concrete structural formula is as follows:
Above-mentioned listed compound C01～C48, is to meet present invention spirit and the representative structure of principle, it will be appreciated that list The concrete structure of above compound, is intended merely to preferably explain the present invention, is not limitation of the present invention.
The two of the purpose of the present invention, are to provide the application of above-mentioned pair of indeno phenoxazine electroluminescent organic material.
The technical scheme is that a kind of double indeno phenoxazine electroluminescent organic material Application, in organic electroluminescence device, at least functional layer contains as above double indeno phenoxazines described in any one Electroluminescent organic material.
Using double indeno phenoxazine electroluminescent organic materials of the present invention as luminescent layer, the OLED of making, device High-high brightness 2860-4970cd/m2, maximum current efficiency 1.2-1.9cd/A, device efficiency is good, this explanation present invention's Double indeno phenoxazine electroluminescent organic materials have preferable luminescent properties.
Prepared organic electroluminescence device generally comprises ITO Conducting Glass (anode), the hole being sequentially overlapped Implanted layer (HAT-CN), hole transmission layer (NPB), luminescent layer (material in the present invention), electron transfer layer (TPBI), electronics are noted Enter layer (LiF) and cathode layer (Mg+Ag/Ag).The structural representation of prepared organic electroluminescence device is as shown in Figure 1.Institute Having functional layer all to use vacuum evaporation process to make, the molecular structural formula of some organic compound used in such device is such as Under:
In the present invention, the functional layer of device is not limited to use above-mentioned material, and these materials can replace with other material, Can replace with TAPC etc. to device performance to be further improved, such as hole transmission layer, electron transfer layer can use TpPYPB Deng replacement, the molecular structural formula of these materials is as follows:
The invention has the beneficial effects as follows:
1. the invention provides a class with double indenes rings phenoxazine the little molecule organic electroluminescent material as framing structure. The material of the present invention has electron rich, nonplanar structure feature, and suitable molecular mass (molecular weight 400-900), tool There are good thin film stability (being difficult to crystallization), applicable molecular entergy level (current material of can arranging in pairs or groups).Therefore, the material of the present invention Can be applied in field of organic electroluminescence as the luminescent layer of small molecule OLED device.
2. using double indeno phenoxazine electroluminescent organic materials of the present invention as luminescent layer, the OLED of making, device High-high brightness 2860-4970cd/m of part2, maximum current efficiency 1.2-1.9cd/A, device efficiency is good, and this illustrates the present invention Double indeno phenoxazine electroluminescent organic materials there is preferable luminescent properties.
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 Entering layer (6) and cathode layer (7), wherein, luminescent layer (4) relates to the electroluminescent organic material prepared by the present 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:
Embodiment 1: the preparation of compound C02
The preparation of compound 1: in 1L there-necked flask, addition iodomethane (21.29g, 0.15mol), phenoxazine (18.32g, 0.1mol), dimethylbenzene (450g), under nitrogen protection, addition sodium tert-butoxide (19.20g, 0.2mol), palladium (0.246g, 1% Mol), Xantphos (1.161g, 2%mol), heat up, 120 DEG C of insulation reaction 12h, it is cooled to 30 DEG C, reactant liquor is washed, point Liquid, anhydrous magnesium sulfate is dried, and desolventizing, and gained pale tan oil uses 50g petroleum ether dissolution, by the silica gel that 25cm is thick Post carries out column chromatography (petroleum ether drip washing), collects the post liquid excessively containing product, then desolventizing, and petroleum ether room temperature is pulled an oar, and sucking filtration is also It is dried to obtain compound 1, faint yellow solid 12.88g, yield 65.3%, MS (m/s): 197.1.
The preparation of compound 2: equipped with in the 1L there-necked flask of constant pressure funnel, under nitrogen protection, add compound 1 (19.72g, 0.10mol), the THF (300g) being dried, add NaH (0.24g, 0.01mol) under stirring, sodium tert-butoxide (2.88g, 0.03mol), at Nei Wen-80 DEG C, being slowly added dropwise n-butyllithium solution (100mL, 0.25mol), 1h dropping is complete, and rear low temperature is anti- Answer at 1h, Nei Wen-80 DEG C, be slowly added dropwise glycol dibromide solution (containing 65.8g, 0.35mol glycol dibromide；0.24g NaH；50g THF), 1h dropping is complete, rear low-temp reaction 3h, is naturally warmed to room temperature stirring 5h, drips 200g 10% dilute in bottle Hydrochloric acid, stands separatory, and organic layer washes desolventizing after 1 time, and gained pale tan oil uses 30g toluene to dissolve, and passes through 20cm Thick silicagel column carries out column chromatography (toluene drip washing), collects and crosses post liquid, then desolventizing containing product, residue use toluene/ Petroleum ether recrystallization, obtains compound 2, light yellow solid 16.05g, yield 45.2%, and MS (m/s): 354.9.
The preparation of compound 3: equipped with in the 1L there-necked flask of constant pressure funnel, under nitrogen protection, be sequentially added into double Connection boric acid pinacol ester (30.47g, 0.12mol), dioxane (300ml), palladium (0.449g, 2%mol), tri-tert Phosphine tetrafluoroborate (1.161g, 4%mol), 18-crown-6 (2.64g, 10%mol), potassium acetate (29.44g, 0.3mol), heats up To 115 DEG C of backflows, being now slowly added dropwise dioxane (500ml) solution of compound 2 (35.50g, 0.1mol), 2h drips Finishing, rear insulation reaction 10h, be cooled to 40 DEG C, reactant liquor is washed, and adds 800g toluene separatory, and anhydrous magnesium sulfate is dried, and precipitation Agent, gained pale tan oil uses 100 toluene heats of solution, and (hot toluene drenches to carry out column chromatography by the silicagel column that 30cm is thick Wash), collect the post liquid excessively containing product, then desolventizing, obtain compound 2, light yellow liquid 37.59g, yield 83.7%, MS (m/s): 449.3.
The preparation of compound 4: in 1L there-necked flask, adds compound 3 (44.92g, 0.1mol), adjacent bromo-iodobenzene (28.29g, 0.1mol), potassium carbonate (41.40g, 0.3mol), toluene (700g), deionized water (200g), under nitrogen protection, add Enter Pd (PPh3)4(2.311g, 2%mol), is warming up to backflow, insulation reaction 10h, is cooled to 30 DEG C, and separatory, organic facies is quickly led to Crossing the thick silicagel column of 35cm, cross post loss of thick fluid solvent, the thick product of gained uses toluene/petroleum ether recrystallization, obtains yellow-brown solid, takes out Filter and be dried, be repeated 1 times according to above-mentioned recrystallization operation, obtain compound 4, faint yellow solid 40.78g, yield 80.4%, MS (m/s): 507.0.
The preparation of compound 5: be dissolved in the oxolane that 100mL is dried by compound 4 (5.07g, 0.01mol), turns Enter equipped with in the 500mL there-necked flask of constant pressure funnel, under nitrogen protection, when temperature drop is to-75 DEG C in system, be slowly added dropwise The hexane solution (2.5mol/L) of 8.0mL n-BuLi, drips and finishes, and-75 DEG C are incubated anti-2h, and insulation is finished, and equality of temperature adds in batches Benzophenone (3.64g, 0.02mol), finishes rear equality of temperature insulation reaction 2h, and insulation is finished, and room temperature continues insulation reaction 4h, drips afterwards Enter the dilute hydrochloric acid of 70g mass concentration 10%, stir 1h, separatory, collect organic facies, slough solvent, obtain the thick product of compound 5 10.3g, the thick product of gained compound 5, no longer refine, be directly used in next step reaction.
The preparation of compound C01: in 500mL there-necked flask, the thick product of the compound 5 obtained by addition previous step (10.3g), adding glacial acetic acid 60g, mass concentration is the concentrated hydrochloric acid 0.4g of 36.5%, is warming up to backflow, insulation reaction 10h, fall Temperature, to 25 DEG C, adds 100g toluene and 200g water, separatory, organic facies precipitation, and crude oil is crossed silicagel column, petroleum ether drip washing, received Collection crosses post liquid containing single product component, petroleum ether making beating after precipitation, and sucking filtration is collected filter cake, obtained compound C01, and white is solid Body 3.84g, yield 56.6%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C51H35NO, theoretical value 677.27, test value 677.13. Elementary analysis (C51H35NO), theoretical value C:90.37, H:5.20, N:2.07, O:2.36, measured value C:90.34, H:5.21, N: 2.06, O:2.39.
Embodiment 2: the preparation of compound C03
The preparation of compound 6: using 4,4'-dinitrile benzophenone replacement benzophenone is as raw material, according to embodiment 1 Described method (preparation of compound 5), puts into 4.64g (0.02mol) 4,4'-dinitrile benzophenone, obtains compound 6 thick Product, no longer refine, and are directly used in next step reaction.
The preparation of compound C03: use compound 6 to replace compound 5 as raw material, (change according to method described in embodiment 1 The preparation of compound C01), put into 0.01mol (theoretical value) compound 6, obtain compound C03, faint yellow solid 4.70g, yield 60.4%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C55H31N5O, theoretical value 777.25, test value 777.39. Elementary analysis (C55H31N5O), theoretical value C:84.92, H:4.02, N:9.00, O:2.06, measured value C:84.89, H:4.01, N: 9.02, O:2.08.
Embodiment 3: the preparation of compound C05
The preparation of compound 7: use bromoethane replacement iodomethane is as raw material, according to method (compound described in embodiment 1 The preparation of 1), put into 16.35g (0.15mol) bromoethane, obtain compound 7 fine work, faint yellow solid 9.53g, yield 45.1%, MS (m/s): 211.1.
The preparation of compound 8: use compound 7 replace compound 1 as raw material, according to method (chemical combination described in embodiment 1 The preparation of thing 2), put into 21.13g (0.1mol) compound 7, obtain compound 8 fine work, faint yellow solid 16.64g, yield 45.1%, MS (m/s): 368.9.
The preparation of compound 9: use compound 8 replace compound 2 as raw material, according to method (chemical combination described in embodiment 1 The preparation of thing 3), put into 36.91g (0.1mol) compound 8, obtain compound 9 fine work, weak yellow liquid 37.24g, yield 80.4%, MS (m/s): 463.3.
The preparation of compound 10: use compound 9 to replace compound 3 as raw material, (change according to method described in embodiment 1 The preparation of compound 4), put into 46.32g (0.1mol) compound 9, obtain compound 10 fine work, faint yellow solid 42.85g, yield 82.2%, MS (m/s): 521.0.
The preparation of compound 11: according to method described in embodiment 1 (preparation of compound 5), puts into 3.64g (0.02mol) Benzophenone, obtains compound 11 crude product, no longer refines, and is directly used in next step reaction.
The preparation of compound C05: use compound 11 replace compound 5 as raw material, according to method described in embodiment 1 (preparation of compound C02), puts into 0.01mol (theoretical value) compound 11, obtains compound C05, faint yellow solid 4.25g, Yield 61.4%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C52H37NO, theoretical value 691.29, test value 691.04. Elementary analysis (C52H37NO), theoretical value C:90.27, H:5.40, N:2.02, O:2.31, measured value C:90.26, H:5.39, N: 2.03, O:2.32.
Embodiment 4: the preparation of compound C06
The preparation of compound 12: using 4,4'-difluoro benzophenone replacement benzophenone is as raw material, according to embodiment 3 Described method (preparation of compound 11), puts into 4.36g (0.02mol) 4,4'-difluoro benzophenone, obtains compound 12 thick Product, no longer refine, and are directly used in next step reaction.
The preparation of compound C06: use compound 12 replace compound 11 as raw material, according to method described in embodiment 3 (preparation of compound C05), puts into 0.01mol (theoretical value) compound 12, obtains compound C06, faint yellow solid 4.48g, Yield 58.7%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C52H33F4NO, theoretical value 763.25, test value 763.20. Elementary analysis (C52H33F4NO), theoretical value C:81.77, H:4.36, F:9.95, N:1.83, O:2.09, measured value C:81.76, H: 4.35, F:9.96, N:1.85, O:2.08.
Embodiment 5: the preparation of compound C05
The preparation of compound 13: according to method described in embodiment 1 (preparation of compound 1), puts into 13.89g (0.15mol) Tertiary butyl chloride, obtains compound 13 fine work, faint yellow solid 11.46g, yield 47.9%, and MS (m/s): 239.1.
The preparation of compound 14: according to method described in embodiment 1 (preparation of compound 2), puts into 23.93g (0.1mol) Compound 13, obtains compound 14 fine work, faint yellow solid 16.96g, yield 42.7%, and MS (m/s): 397.0.
The preparation of compound 15: according to method described in embodiment 1 (preparation of compound 3), puts into 39.71g (0.1mol) Compound 14, obtains compound 15 fine work, weak yellow liquid 37.87g, yield 77.1%, and MS (m/s): 491.3.
The preparation of compound 16: according to method described in embodiment 1 (preparation of compound 4), puts into 49.12g (0.1mol) Compound 15, obtains compound 16 fine work, faint yellow solid 44.77g, yield 81.5%, and MS (m/s): 549.0.
The preparation of compound 17: according to method described in embodiment 1 (preparation of compound 5), puts into 1.16g (0.02mol) Acetone, obtains compound 17 crude product, no longer refines, and is directly used in next step reaction.
The preparation of compound C08: according to method described in embodiment 1 (preparation of compound C02), puts into 0.01mol (theoretical Value) compound 17, obtain compound C08, faint yellow solid 3.13g, yield 66.3%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C34H33NO, theoretical value 471.26, test value 471.12. Elementary analysis (C34H33NO), theoretical value C:86.59, H:7.05, N:2.97, O:3.39, measured value C:86.57, H:7.06, N: 2.97, O:3.40.
Embodiment 6: the preparation of compound C14
The preparation of compound 18: according to method described in embodiment 1 (preparation of compound 1), puts into 20.55g (0.15mol) N-butyl bromide, obtains compound 18 fine work, faint yellow solid 12.28g, yield 51.3%, and MS (m/s): 239.1.
The preparation of compound 19: according to method described in embodiment 1 (preparation of compound 2), puts into 23.93g (0.1mol) Compound 18, obtains compound 19 fine work, faint yellow solid 16.24g, yield 40.9%, and MS (m/s): 397.0.
The preparation of compound 20: according to method described in embodiment 1 (preparation of compound 3), puts into 39.71g (0.1mol) Compound 19, obtains compound 20 fine work, weak yellow liquid 37.04g, yield 75.4%, and MS (m/s): 491.3.
The preparation of compound 21: according to method described in embodiment 1 (preparation of compound 4), puts into 49.12g (0.1mol) Compound 20, obtains compound 21 fine work, faint yellow solid 44.00g, yield 80.1%, and MS (m/s): 549.0.
The preparation of compound 22: according to method described in embodiment 1 (preparation of compound 5), puts into 4.36g (0.02mol) 4,4'-difluoro benzophenones, obtain compound 22 crude product, no longer refine, and are directly used in next step reaction.
The preparation of compound C14: according to method described in embodiment 1 (preparation of compound C02), puts into 0.01mol (theoretical Value) compound 22, obtain compound C14, faint yellow solid 5.47g, yield 69.1%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C54H37F4NO, theoretical value 791.28, test value 791.45. Elementary analysis (C54H37F4NO), theoretical value C:81.90, H:4.71, F:9.60, N:1.77, O:2.02, measured value C:81.88, H: 4.72, F:9.62, N:1.77, O:2.01.
Embodiment 7: the preparation of compound C15
The preparation of compound 23: according to method described in embodiment 1 (preparation of compound 1), puts into 18.84g (0.12mol) Bromobenzene, obtains compound 23 fine work, faint yellow solid 19.24g, yield 74.2%, and MS (m/s): 259.1.
The preparation of compound 24: according to method described in embodiment 1 (preparation of compound 2), puts into 25.93g (0.1mol) Compound 23, obtains compound 24 fine work, faint yellow solid 21.06g, yield 50.5%, and MS (m/s): 416.9.
The preparation of compound 25: according to method described in embodiment 1 (preparation of compound 3), puts into 41.71g (0.1mol) Compound 24, obtains compound 25 fine work, weak yellow liquid 40.49g, yield 79.2%, and MS (m/s): 511.3.
The preparation of compound 26: according to method described in embodiment 1 (preparation of compound 4), puts into 51.12g (0.1mol) Compound 25, obtains compound 26 fine work, faint yellow solid 45.37g, yield 79.7%, and MS (m/s): 569.0.
The preparation of compound 27: according to method described in embodiment 1 (preparation of compound 5), puts into 3.64g (0.02mol) Benzophenone, obtains compound 27 crude product, no longer refines, and is directly used in next step reaction.
The preparation of compound C15: according to method described in embodiment 1 (preparation of compound C02), puts into 0.01mol (theoretical Value) compound 27, obtain compound C15, faint yellow solid 4.72g, yield 63.8%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C56H37NO, theoretical value 739.29, test value 739.36. Elementary analysis (C56H37NO), theoretical value C:90.90, H:5.05, N:1.89, O:2.16, measured value C:90.88, H:5.04, N: 1.90, O:2.18.
Embodiment 8: the preparation of compound C19
The preparation of compound 28: according to method described in embodiment 1 (preparation of compound 1), puts into 27.97g (0.12mol) 4-bromo biphenyl, obtains compound 28 fine work, faint yellow solid 25.99g, yield 77.5%, and MS (m/s): 335.1.
The preparation of compound 29: according to method described in embodiment 1 (preparation of compound 2), puts into 33.54g (0.1mol) Compound 28, obtains compound 29 fine work, faint yellow solid 23.77g, yield 48.2%, and MS (m/s): 493.0.
The preparation of compound 30: according to method described in embodiment 1 (preparation of compound 3), puts into 49.32g (0.1mol) Compound 29, obtains compound 30 fine work, faint yellow solid 47.57g, yield 81.0%, and MS (m/s): 587.3.
The preparation of compound 31: according to method described in embodiment 1 (preparation of compound 4), puts into 58.73g (0.1mol) Compound 30, obtains compound 31 fine work, faint yellow solid 51.95g, yield 80.5%, and MS (m/s): 645.0.
The preparation of compound 32: according to method described in embodiment 1 (preparation of compound 5), puts into 3.64g (0.02mol) Benzophenone, obtains compound 32 crude product, no longer refines, and is directly used in next step reaction.
The preparation of compound C19: according to method described in embodiment 1 (preparation of compound C02), puts into 0.01mol (theoretical Value) compound 32, obtain compound C19, faint yellow solid 4.99g, yield 61.2%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C62H41NO, theoretical value 815.32, test value 815.12. Elementary analysis (C62H41NO), theoretical value C:91.26, H:5.06, N:1.72, O:1.96, measured value C:91.23, H:5.08, N: 1.71, O:1.98.
Embodiment 9: the preparation of compound C21
The preparation of compound 33: according to method described in embodiment 1 (preparation of compound 1), puts into 37.10g (0.12mol) 5'-bromo-1,1':3', 1 "-terphenyl, obtain compound 33 fine work, faint yellow solid 32.59g, yield 79.2%, MS (m/s): 411.2。
The preparation of compound 34: according to method described in embodiment 1 (preparation of compound 2), puts into 41.15g (0.1mol) Compound 33, obtains compound 34 fine work, faint yellow solid 28.24g, yield 49.6%, and MS (m/s): 569.0.
The preparation of compound 35: according to method described in embodiment 1 (preparation of compound 3), puts into 56.93g (0.1mol) Compound 34, obtains compound 35 fine work, faint yellow solid 53.27g, yield 80.3%, and MS (m/s): 663.3.
The preparation of compound 36: according to method described in embodiment 1 (preparation of compound 4), puts into 66.34g (0.1mol) Compound 35, obtains compound 36 fine work, faint yellow solid 58.80g, yield 81.5%, and MS (m/s): 721.0.
The preparation of compound 37: according to method described in embodiment 1 (preparation of compound 5), puts into 1.72g (0.02mol) Propione, obtains compound 37 crude product, no longer refines, and is directly used in next step reaction.
The preparation of compound C21: according to method described in embodiment 1 (preparation of compound C02), puts into 0.01mol (theoretical Value) compound 37, obtain compound C21, faint yellow solid 4.11g, yield 58.7%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C52H45NO, theoretical value 699.35, test value 699.09. Elementary analysis (C52H45NO), theoretical value C:89.23, H:6.48, N:2.00, O:2.29, measured value C:89.22, H:6.50, N: 2.01, O:2.27.
Embodiment 10: the preparation of compound C26
The preparation of compound 38: according to method described in embodiment 1 (preparation of compound 1), puts into 24.85g (0.12mol) 1-bromonaphthalene, obtains compound 38 fine work, faint yellow solid 23.33g, yield 75.4%, and MS (m/s): 309.1.
The preparation of compound 39: according to method described in embodiment 1 (preparation of compound 2), puts into 30.94g (0.1mol) Compound 38, obtains compound 39 fine work, faint yellow solid 22.38g, yield 47.9%, and MS (m/s): 366.9.
The preparation of compound 40: according to method described in embodiment 1 (preparation of compound 3), puts into 46.72g (0.1mol) Compound 39, obtains compound 40 fine work, weak yellow liquid 40.86g, yield 72.8%, and MS (m/s): 561.3.
The preparation of compound 41: according to method described in embodiment 1 (preparation of compound 4), puts into 56.13g (0.1mol) Compound 40, obtains compound 41 fine work, faint yellow solid 48.99g, yield 79.1%, and MS (m/s): 619.0.
The preparation of compound 42: according to method described in embodiment 1 (preparation of compound 5), puts into 3.64g (0.02mol) Benzophenone, obtains compound 42 crude product, no longer refines, and is directly used in next step reaction.
The preparation of compound C26: according to method described in embodiment 1 (preparation of compound C02), puts into 0.01mol (theoretical Value) compound 42, obtain compound C26, faint yellow solid 5.02g, yield 63.5%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C60H39NO, theoretical value 789.30, test value 789.13. Elementary analysis (C60H39NO), theoretical value C:91.23, H:4.97, N:1.77, O:2.03, measured value C:91.20, H:4.98, N: 1.78, O:2.04.
Embodiment 11: the preparation of compound C28
The preparation of compound 43: according to method described in embodiment 1 (preparation of compound 1), puts into 33.98g (0.12mol) 1-(4-bromophenyl) naphthalene, obtains compound 43 fine work, faint yellow solid 29.99g, yield 77.8%, and MS (m/s): 385.2.
The preparation of compound 44: according to method described in embodiment 1 (preparation of compound 2), puts into 38.55g (0.1mol) Compound 43, obtains compound 44 fine work, faint yellow solid 27.33g, yield 50.3%, and MS (m/s): 543.0.
The preparation of compound 45: according to method described in embodiment 1 (preparation of compound 3), puts into 54.33g (0.1mol) Compound 44, obtains compound 45 fine work, faint yellow solid 49.78g, yield 78.1%, and MS (m/s): 637.3.
The preparation of compound 46: according to method described in embodiment 1 (preparation of compound 4), puts into 63.74g (0.1mol) Compound 45, obtains compound 46 fine work, faint yellow solid 52.92g, yield 76.1%, and MS (m/s): 695.0.
The preparation of compound 47: according to method described in embodiment 1 (preparation of compound 5), puts into 1.72g (0.02mol) Propione, obtains compound 47 crude product, no longer refines, and is directly used in next step reaction.
The preparation of compound C28: according to method described in embodiment 1 (preparation of compound C02), puts into 0.01mol (theoretical Value) compound 47, obtain compound C28, faint yellow solid 3.52g, yield 52.2%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C50H43NO, theoretical value 673.33, test value 673.02. Elementary analysis (C50H43NO), theoretical value C:89.12, H:6.43, N:2.08, O:2.37, measured value C:89.10, H:6.40, N: 2.11, O:2.39.
Embodiment 12: the preparation of compound C30
The preparation of compound 48: according to method described in embodiment 1 (preparation of compound 1), puts into 33.98g (0.12mol) 1-bromo-4-phenylnaphthalene, obtains compound 48 fine work, faint yellow solid 30.14g, yield 78.2%, and MS (m/s): 385.2.
The preparation of compound 49: according to method described in embodiment 1 (preparation of compound 2), puts into 38.55g (0.1mol) Compound 48, obtains compound 49 fine work, faint yellow solid 27.76g, yield 51.1%, and MS (m/s): 543.0.
The preparation of compound 50: according to method described in embodiment 1 (preparation of compound 3), puts into 54.33g (0.1mol) Compound 49, obtains compound 50 fine work, faint yellow solid 50.54g, yield 79.3%, and MS (m/s): 637.3.
The preparation of compound 51: according to method described in embodiment 1 (preparation of compound 4), puts into 63.74g (0.1mol) Compound 50, obtains compound 51 fine work, faint yellow solid 53.97g, yield 77.6%, and MS (m/s): 695.0.
The preparation of compound 52: according to method described in embodiment 1 (preparation of compound 5), puts into 1.72g (0.02mol) Propione, obtains compound 52 crude product, no longer refines, and is directly used in next step reaction.
The preparation of compound C30: according to method described in embodiment 1 (preparation of compound C02), puts into 0.01mol (theoretical Value) compound 52, obtain compound C30, faint yellow solid 3.58g, yield 53.1%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C50H43NO, theoretical value 673.33, test value 673.05. Elementary analysis (C50H43NO), theoretical value C:89.12, H:6.43, N:2.08, O:2.37, measured value C:89.10, H:6.41, N: 2.11, O:2.38.
Embodiment 13: the preparation of compound C33
The preparation of compound 53: according to method described in embodiment 1 (preparation of compound 1), puts into 30.86g (0.12mol) 9-bromine is luxuriant and rich with fragrance, obtains compound 53 fine work, faint yellow solid 28.43g, yield 79.1%, and MS (m/s): 359.1.
The preparation of compound 54: according to method described in embodiment 1 (preparation of compound 2), puts into 35.94g (0.1mol) Compound 53, obtains compound 54 fine work, faint yellow solid 34.29g, yield 66.3%, and MS (m/s): 517.0.
The preparation of compound 55: according to method described in embodiment 1 (preparation of compound 3), puts into 51.72g (0.1mol) Compound 54, obtains compound 55 fine work, faint yellow solid 49.64g, yield 81.2%, and MS (m/s): 611.3.
The preparation of compound 56: according to method described in embodiment 1 (preparation of compound 4), puts into 61.13g (0.1mol) Compound 55, obtains compound 56 fine work, faint yellow solid 52.34g, yield 78.2%, and MS (m/s): 669.0.
The preparation of compound 57: according to method described in embodiment 1 (preparation of compound 5), puts into 3.64g (0.02mol) Benzophenone, obtains compound 57 crude product, no longer refines, and is directly used in next step reaction.
The preparation of compound C33: according to method described in embodiment 1 (preparation of compound C02), puts into 0.01mol (theoretical Value) compound 57, obtain compound C33, faint yellow solid 4.26g, yield 50.7%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C64H41NO, theoretical value 839.32, test value 839.04. Elementary analysis (C64H41NO), theoretical value C:91.51, H:4.92, N:1.67, O:1.90, measured value C:91.49, H:4.88, N: 1.70, O:1.93.
Embodiment 14: the preparation of compound C36
The preparation of compound 58: according to method described in embodiment 1 (preparation of compound 1), puts into 18.96g (0.12mol) 4-bromopyridine, obtains compound 58 fine work, faint yellow solid 11.74g, yield 45.1%, and MS (m/s): 260.1.
The preparation of compound 59: according to method described in embodiment 1 (preparation of compound 2), puts into 26.03g (0.1mol) Compound 58, obtains compound 59 fine work, faint yellow solid 13.84g, yield 33.1%, and MS (m/s): 417.9.
The preparation of compound 60: according to method described in embodiment 1 (preparation of compound 3), puts into 41.81g (0.1mol) Compound 59, obtains compound 60 fine work, weak yellow liquid 30.84g, yield 60.2%, and MS (m/s): 512.3.
The preparation of compound 61: according to method described in embodiment 1 (preparation of compound 4), puts into 51.22g (0.1mol) Compound 60, obtains compound 61 fine work, faint yellow solid 31.02g, yield 54.4%, and MS (m/s): 570.0.
The preparation of compound 62: according to method described in embodiment 1 (preparation of compound 5), puts into 3.64g (0.02mol) Benzophenone, obtains compound 62 crude product, no longer refines, and is directly used in next step reaction.
The preparation of compound C36: according to method described in embodiment 1 (preparation of compound C02), puts into 0.01mol (theoretical Value) compound 62, obtain compound C36, faint yellow solid 2.94g, yield 39.7%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C55H36N2O, theoretical value 740.28, test value 740.41. Elementary analysis (C55H36N2O), theoretical value C:89.16, H:4.90, N:3.78, O:2.16, measured value C:89.14, H:4.92, N: 3.77, O:2.17.
Embodiment 15: the preparation of compound C38
The preparation of compound 63: according to method described in embodiment 14 (preparation of compound 62), puts into 4.64g (0.02mol) 4,4'-dinitrile benzophenone, obtains compound 63 crude product, no longer refines, and is directly used in next step reaction In.
The preparation of compound C38: according to method described in embodiment 14 (preparation of compound C36), puts into 0.01mol (reason Opinion value) compound 63, obtain compound C38, faint yellow solid 3.13g, yield 37.2%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C59H32N6O, theoretical value 840.26, test value 840.44. Elementary analysis (C59H32N6O), theoretical value C:84.27, H:3.84, N:9.99, O:1.90, measured value C:84.26, H:3.86, N: 9.97, O:1.91.
Embodiment 16: the preparation of compound C41
The preparation of compound 64: according to method described in embodiment 1 (preparation of compound 1), puts into 28.09g (0.12mol) 4-(4-bromophenyl) pyridine, obtains compound 64 fine work, faint yellow solid 15.71g, yield 46.7%, and MS (m/s): 336.4.
The preparation of compound 65: according to method described in embodiment 1 (preparation of compound 2), puts into 33.64g (0.1mol) Compound 64, obtains compound 65 fine work, faint yellow solid 18.63g, yield 37.7%, and MS (m/s): 494.0.
The preparation of compound 66: according to method described in embodiment 1 (preparation of compound 3), puts into 49.42g (0.1mol) Compound 65, obtains compound 66 fine work, weak yellow liquid 35.95g, yield 61.1%, and MS (m/s): 588.3.
The preparation of compound 67: according to method described in embodiment 1 (preparation of compound 4), puts into 58.83g (0.1mol) Compound 66, obtains compound 67 fine work, faint yellow solid 36.33g, yield 56.2%, and MS (m/s): 646.0.
The preparation of compound 68: according to method described in embodiment 1 (preparation of compound 5), puts into 3.64g (0.02mol) Benzophenone, obtains compound 68 crude product, no longer refines, and is directly used in next step reaction.
The preparation of compound C41: according to method described in embodiment 1 (preparation of compound C02), puts into 0.01mol (theoretical Value) compound 68, obtain compound C41, faint yellow solid 3.65g, yield 44.7%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C61H40N2O, theoretical value 816.31, test value 816.22. Elementary analysis (C61H40N2O), theoretical value C:89.68, H:4.93, N:3.43, O:1.96, measured value C:89.64, H:4.96, N: 3.45, O:1.95.
Embodiment 17: the preparation of compound C42
The preparation of compound 69: according to method described in embodiment 1 (preparation of compound 1), puts into 34.10g (0.12mol) 4-(4-bromonaphthalene) pyridine, obtains compound 69 fine work, faint yellow solid 17.35g, yield 44.9%, and MS (m/s): 386.1.
The preparation of compound 70: according to method described in embodiment 1 (preparation of compound 2), puts into 38.64g (0.1mol) Compound 69, obtains compound 70 fine work, faint yellow solid 26.83g, yield 49.3%, and MS (m/s): 544.0.
The preparation of compound 71: according to method described in embodiment 1 (preparation of compound 3), puts into 54.42g (0.1mol) Compound 70, obtains compound 71 fine work, faint yellow solid 40.03g, yield 62.7%, and MS (m/s): 638.3.
The preparation of compound 72: according to method described in embodiment 1 (preparation of compound 4), puts into 63.84g (0.1mol) Compound 71, obtains compound 72 fine work, faint yellow solid 29.67g, yield 42.6%, and MS (m/s): 695.0.
The preparation of compound 73: according to method described in embodiment 1 (preparation of compound 5), puts into 1.72g (0.02mol) Propione, obtains compound 73 crude product, no longer refines, and is directly used in next step reaction.
The preparation of compound C42: according to method described in embodiment 1 (preparation of compound C02), puts into 0.01mol (theoretical Value) compound 73, obtain compound C42, faint yellow solid 3.52g, yield 52.2%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C49H42N2O, theoretical value 674.33, test value 674.07. Elementary analysis (C49H42N2O), theoretical value C:87.21, H:6.27, N:4.15, O:2.37, measured value C:87.19, H:6.26, N: 4.16, O:2.39.
Embodiment 18: the preparation of compound C44
The preparation of compound 74: according to method described in embodiment 1 (preparation of compound 1), puts into 38.91g (0.12mol) The bromo-N of 4-, N-diphenyl aniline, obtains compound 74 fine work, faint yellow solid 23.29g, yield 54.6%, MS (m/s): 426.2。
The preparation of compound 75: according to method described in embodiment 1 (preparation of compound 2), puts into 42.65g (0.1mol) Compound 74, obtains compound 75 fine work, faint yellow solid 22.79g, yield 39.0%, and MS (m/s): 584.0.
The preparation of compound 76: according to method described in embodiment 1 (preparation of compound 3), puts into 58.43g (0.1mol) Compound 75, obtains compound 76 fine work, faint yellow solid 35.89g, yield 54.1%, and MS (m/s): 663.3.
The preparation of compound 77: according to method described in embodiment 1 (preparation of compound 4), puts into 66.34g (0.1mol) Compound 76, obtains compound 77 fine work, faint yellow solid 30.56g, yield 41.5%, and MS (m/s): 736.1.
The preparation of compound 78: according to method described in embodiment 1 (preparation of compound 5), puts into 1.16g (0.02mol) Acetone, obtains compound 78 crude product, no longer refines, and is directly used in next step reaction.
The preparation of compound C44: according to method described in embodiment 1 (preparation of compound C02), puts into 0.01mol (theoretical Value) compound 78, obtain compound C44, faint yellow solid 2.70g, yield 41.0%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C48H38N2O, theoretical value 658.30, test value 658.11. Elementary analysis (C48H38N2O), theoretical value C:87.51, H:5.81, N:4.25, O:2.43, measured value C:87.50, H:5.83, N: 4.22, O:2.45.
Embodiment 19: the preparation of compound C45
The preparation of compound 79: according to method described in embodiment 1 (preparation of compound 1), puts into 37.34g (0.12mol) 2-bromo-4,6-diphenylpyrimidin, obtain compound 79 fine work, faint yellow solid 13.52g, yield 32.7%, MS (m/s): 413.2。
The preparation of compound 80: according to method described in embodiment 1 (preparation of compound 2), puts into 41.35g (0.1mol) Compound 79, obtains compound 80 fine work, pistac solid 24.34g, yield 42.6%, and MS (m/s): 571.0.
The preparation of compound 81: according to method described in embodiment 1 (preparation of compound 3), puts into 57.13g (0.1mol) Compound 80, obtains compound 81 fine work, pistac solid 47.31g, yield 71.1%, and MS (m/s): 665.3.
The preparation of compound 82: according to method described in embodiment 1 (preparation of compound 4), puts into 66.54g (0.1mol) Compound 81, obtains compound 82 fine work, pistac solid 47.17g, yield 65.2%, and MS (m/s): 723.0.
The preparation of compound 83: according to method described in embodiment 1 (preparation of compound 5), puts into 1.72g (0.02mol) Propione, obtains compound 83 crude product, no longer refines, and is directly used in next step reaction.
The preparation of compound C45: according to method described in embodiment 1 (preparation of compound C02), puts into 0.01mol (theoretical Value) compound 83, obtain compound C45, pistac solid 3.29g, yield 46.9%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C50H43N3O, theoretical value 701.34, test value 701.12. Elementary analysis (C50H43N3O), theoretical value C:85.56, H:6.17, N:5.99, O:2.28, measured value C:85.53, H:6.18, N: 5.98, O:2.31.
Embodiment 20: the preparation of compound C46
The preparation of compound 84: according to method described in embodiment 1 (preparation of compound 1), puts into 32.78g (0.12mol) 2-bromo-1-phenyl-1H-benzimidazole, obtains compound 84 fine work, faint yellow solid 13.21g, yield 35.2%, MS (m/s): 375.1。
The preparation of compound 85: according to method described in embodiment 1 (preparation of compound 2), puts into 37.54g (0.1mol) Compound 84, obtains compound 85 fine work, pistac solid 23.62g, yield 44.3%, and MS (m/s): 533.0.
The preparation of compound 86: according to method described in embodiment 1 (preparation of compound 3), puts into 53.32g (0.1mol) Compound 85, obtains compound 86 fine work, pistac solid 35.39g, yield 57.8%, and MS (m/s): 612.3.
The preparation of compound 87: according to method described in embodiment 1 (preparation of compound 4), puts into 61.23g (0.1mol) Compound 86, obtains compound 87 fine work, pistac solid 40.71g, yield 59.4%, and MS (m/s): 685.0.
The preparation of compound 88: according to method described in embodiment 1 (preparation of compound 5), puts into 1.72g (0.02mol) Propione, obtains compound 88 crude product, no longer refines, and is directly used in next step reaction.
The preparation of compound C46: according to method described in embodiment 1 (preparation of compound C02), puts into 0.01mol (theoretical Value) compound 88, obtain compound C46, pistac solid 3.31g, yield 48.3%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C47H41N3O, theoretical value 663.32, test value 663.17. Elementary analysis (C47H41N3O), theoretical value C:85.03, H:6.23, N:6.33, O:2.41, measured value C:85.05, H:6.21, N: 6.35, O:2.39.
Embodiment 21: the preparation of compound C47
The preparation of compound 89: according to method described in embodiment 1 (preparation of compound 1), puts into 34.22g (0.12mol) 2-bromo-4-phenylquinazoline, obtains compound 89 fine work, pistac solid 12.98g, yield 33.5%, MS (m/s): 387.1。
The preparation of compound 90: according to method described in embodiment 1 (preparation of compound 2), puts into 38.74g (0.1mol) Compound 89, obtains compound 90 fine work, pistac solid 16.52g, yield 30.3%, and MS (m/s): 545.0.
The preparation of compound 91: according to method described in embodiment 1 (preparation of compound 3), puts into 54.52g (0.1mol) Compound 90, obtains compound 91 fine work, pistac solid 34.65g, yield 54.2%, and MS (m/s): 639.3.
The preparation of compound 92: according to method described in embodiment 1 (preparation of compound 4), puts into 63.94g (0.1mol) Compound 91, obtains compound 92 fine work, pistac solid 38.43g, yield 55.1%, and MS (m/s): 697.0.
The preparation of compound 93: according to method described in embodiment 1 (preparation of compound 5), puts into 1.72g (0.02mol) Propione, obtains compound 93 crude product, no longer refines, and is directly used in next step reaction.
The preparation of compound C47: according to method described in embodiment 1 (preparation of compound C02), puts into 0.01mol (theoretical Value) compound 93, obtain compound C47, pistac solid 2.14g, yield 31.7%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C48H41N3O, theoretical value 675.32, test value 675.09. Elementary analysis (C48H41N3O), theoretical value C:85.30, H:6.11, N:6.22, O:2.37, measured value C:85.32, H:6.10, N: 6.22, O:2.36.
Embodiment 22: the preparation of compound C48
The preparation of compound 94: according to method described in embodiment 1 (preparation of compound 1), puts into 38.78g (0.12mol) 4-(3-bromophenyl) dibenzofurans, obtains compound 94 fine work, pistac solid 28.59g, yield 67.2%, MS (m/ S): 425.1.
The preparation of compound 95: according to method described in embodiment 1 (preparation of compound 2), puts into 42.55g (0.1mol) Compound 94, obtains compound 95 fine work, pistac solid 32.25g, yield 55.3%, and MS (m/s): 583.0.
The preparation of compound 96: according to method described in embodiment 1 (preparation of compound 3), puts into 58.33g (0.1mol) Compound 95, obtains compound 96 fine work, pistac solid 35.63g, yield 52.6%, and MS (m/s): 677.3.
The preparation of compound 97: according to method described in embodiment 1 (preparation of compound 4), puts into 67.74g (0.1mol) Compound 96, obtains compound 97 fine work, pistac solid 52.59g, yield 71.5%, and MS (m/s): 735.0.
The preparation of compound 98: according to method described in embodiment 1 (preparation of compound 5), puts into 1.16g (0.02mol) Acetone, obtains compound 98 crude product, no longer refines, and is directly used in next step reaction.
The preparation of compound C48: according to method described in embodiment 1 (preparation of compound C02), puts into 0.01mol (theoretical Value) compound 98, obtain compound C48, pistac solid 3.24g, yield 49.2%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C48H35NO2, theoretical value 657.27, test value 657.46. Elementary analysis (C48H35NO2), theoretical value C:87.64, H:5.37, N:2.13, O:4.86, measured value C:87.67, H:5.36, N: 2.12, O:4.85.
Organic electroluminescence device embodiment:
The present invention chooses compound C06, compound C10, compound C12, compound C15, compound C21, compound C29, compound C33, compound C36, compound C39, compound C41, compound C42, compound C45, compound C46, change Compound C48, as emitting layer material, makes organic electroluminescence device, and device architecture is as shown in Figure 1.By lower floor to upper strata, depend on Secondary for ITO Conducting Glass 1, hole injection layer 2, hole transmission layer 3, luminescent layer 4, electron transfer layer 5, electron injecting layer 6 With cathode layer 7, wherein, luminescent layer 4 is made up of the electroluminescent organic material of the present invention.
Device embodiments 1
The present embodiment prepares organic electroluminescence device 1 by the following method:
(1) ITO (tin indium oxide) glass is cleaned: clean ito glass each 15 with deionized water, acetone, EtOH Sonicate respectively Minute, then process 3 minutes in plasma cleaner；
(2) on anode ito glass, vacuum evaporation hole injection layer HAT-CN, thickness is 10nm；
(3) on hole injection layer, vacuum evaporation hole transmission layer NPB, thickness is 40nm；
(4) on hole transmission layer, vacuum evaporation luminescent layer compound C06, thickness is 30nm；
(5) on luminescent layer, vacuum evaporation is as the TPBI of electron transfer layer, and thickness is 30nm；
(6) on electron transfer layer, vacuum evaporation electron injecting layer LiF, thickness is 1nm；
(7) on electron injecting layer, vacuum evaporation cathode layer Mg:Ag/Ag, Mg:Ag doping ratio 9:1, thickness is 15nm, Ag thickness is 30nm.
The structure of device 1 is ITO/HAT-CN (10nm)/NPB (40nm)/compound 06 (30nm)/TPBI (30nm)/LiF (1nm)/Mg:Ag (15nm)+Ag (30nm), during vacuum evaporation, pressure < 1.0 × 10-3Pa, device 1 open bright voltage, The big photooptical data such as current efficiency, excitation, as shown in table 1.
Device embodiments 2-device embodiments 14
Respectively with compound C10, compound C12, compound C15, compound C21, compound C29, compound C33, change Compound C36, compound C39, compound C41, compound C42, compound C45, compound C46, compound C48 replace compound C06, according to method described in device embodiments 1, makes organic electroluminescence device 2-14.The structure of device 2-14, is respectively ITO/HAT-CN (10nm)/NPB (40nm)/compound 10-compound 48 (30nm)/TPBI (30nm)/LiF (1nm)/Mg:Ag (15nm)+Ag (30nm), device 1-14 to open the photooptical datas such as bright voltage, maximum current efficiency, excitation as shown in table 1 below.
Table 1 device 1-14 photooptical data table
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 (4)

1. the double indeno phenoxazine electroluminescent organic material of a class, it is characterised in that there is molecular structure shown in formula 1:
Wherein, R1、R2、R3、R4The most identical, R1、R2、R3、R4For alkyl or aromatic substituents, R5Replace for alkyl, aromatic series One in base, nitrogen heterocyclic ring or oxygen heterocycle.
The double indeno phenoxazine electroluminescent organic material of a class the most according to claim 1, it is characterised in that described R1、 R2、R3、R4For methyl, ethyl, phenyl, 4-fluorophenyl or 4-cyanophenyl.
The double indeno phenoxazine electroluminescent organic material of a class the most according to claim 1, it is characterised in that described R5For One in following substituted radical:
-CH3、-CH2CH3、-CH2CH2CH2CH3、
4. the application of the double indeno phenoxazine electroluminescent organic material of a class, it is characterised in that in organic electroluminescence device, At least a functional layer contains the double indeno phenoxazine electroluminescent organic materials described in any one of claim 1-3.
CN201610289170.5A 2016-05-04 2016-05-04 Bisindenophenoxazine organic electroluminescence materials and application thereof Pending CN105936821A (en)

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