CN106800525B - A kind of fluorenyl Anthraquinones electroluminescent organic material and its preparation method and application - Google Patents

A kind of fluorenyl Anthraquinones electroluminescent organic material and its preparation method and application Download PDF

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CN106800525B
CN106800525B CN201611154646.0A CN201611154646A CN106800525B CN 106800525 B CN106800525 B CN 106800525B CN 201611154646 A CN201611154646 A CN 201611154646A CN 106800525 B CN106800525 B CN 106800525B
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compound
organic material
fluorenyl
electroluminescent organic
anthraquinones
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CN106800525A (en
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张成新
石宇
高自良
胡葆华
孟凡民
唐英杰
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Valiant Co Ltd
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Abstract

The invention discloses a kind of fluorenyl anthraquinone analog compound class electroluminescent organic materials and its preparation method and application, and the structural formula of above-mentioned electroluminescent organic material isFluorenyl Anthraquinones electroluminescent organic material provided by the invention is applied in OLED luminescent device, so that the current efficiency of device, power efficiency and external quantum efficiency are greatly improved.Fluorenyl Anthraquinones electroluminescent organic material provided by the invention has good application effect, has good industrialization prospect.

Description

A kind of fluorenyl Anthraquinones electroluminescent organic material and its preparation method and application
Technical field
The present invention relates to electroluminescent organic material technical field more particularly to a kind of fluorenyl Anthraquinones organic electroluminescents Material and its preparation method and application.
Background technique
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology can both be used to make New display product is made, production novel illumination product is can be used for, is expected to substitute existing liquid crystal display and fluorescent lighting, Application prospect is very extensive.
Structure of the OLED luminescent device like sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it Between organic functional material, various different function materials are overlapped mutually depending on the application collectively constitutes OLED luminescent device together. As current device, when the two end electrodes application voltage to OLED luminescent device, and pass through electric field action organic layer functional material Positive and negative charge in film layer, positive and negative charge is further compound in luminescent layer, i.e. generation OLED electroluminescent.
Application of the Organic Light Emitting Diode (OLEDs) in terms of large-area flat-plate is shown and is illuminated causes industry and The extensive concern of art circle.However, traditional organic fluorescence materials can only be shone using 25% singlet exciton to be formed is electrically excited, device The internal quantum efficiency of part is lower (up to 25%).External quantum efficiency is generally lower than 5%, and there are also very big with the efficiency of phosphorescent devices Gap.Although phosphor material can efficiently use electricity since the strong SO coupling in heavy atom center enhances intersystem crossing The singlet exciton formed and Triplet exciton are excited, makes the internal quantum efficiency of device up to 100%.But phosphor material exists Expensive, stability of material is poor, and device efficiency tumbles the problems such as serious and limits it in the application of OLEDs.Hot activation is prolonged Slow fluorescence (TADF) material is the third generation luminous organic material developed after organic fluorescence materials and organic phosphorescent material.It should Class material generally has small singlet-triplet poor (Δ EST), and triplet excitons can be changed by anti-intersystem crossing It shines at singlet exciton.This can make full use of the singlet exciton and triplet excitons that are electrically excited lower formation, device it is interior Quantum efficiency can achieve 100%.Meanwhile material structure is controllable, and property is stablized, and it is cheap to be not necessarily to precious metal, in OLEDs Field has a extensive future.
Although theoretically 100% exciton utilization rate may be implemented in TADF material, following problem there are in fact: (1) T1 the and S1 state for designing molecule has strong CT feature, very small S1-T1 state energy gap, although can realize by TADF process High T1 → S1 state exciton conversion ratio, but low S1 state radiation transistion rate is also resulted in, consequently it is difficult to have both (or realizing simultaneously) High exciton utilization rate and high fluorescent radiation efficiency；(2) even if having used doping device to mitigate T exciton concentration quenching effect, greatly Efficiency roll-off is serious at higher current densities for the device of most TADF materials.
For current OLED shows the actual demand of Lighting Industry, the development of OLED material is also far from enough at present, falls Afterwards in the requirement of panel manufacturing enterprise, the organic functional material as material enterprise development higher performance is particularly important.
Summary of the invention
For the above problem existing for existing OLED material, a kind of fluorenyl Anthraquinones electroluminescent organic material is now provided And its preparation method and application, it is desirable to provide a kind of electroluminescent organic material with good photoelectric properties, to meet panel The requirement of manufacturing enterprise.
Specific technical solution is as follows:
The first aspect of the invention is to provide a kind of fluorenyl Anthraquinones electroluminescent organic material, has such spy Sign, above-mentioned electroluminescent organic material using fluorenyl anthraquinone as parent nucleus, structural formula as shown in formula (i) or formula (ii):
Wherein, Ar is selected from aromatic substituent group；
Wherein, R1Selected from containing substituent group or without substituent groupContaining substituent group or without substituent groupContaining substituent group or without substituent groupContaining substituent group or be free of substituent group Wherein, X1、X2Separately it is selected from oxygen atom, sulphur atom, selenium atom, two (C1-10Straight chained alkyl) season alkyl (or the uncle that replaces Alkyl), two (C1-10Branched alkyl) replace season alkyl (or tertiary alkyl), aryl replace season alkyl (or tertiary alkyl), alkyl One of the tertiary amine groups that substituted tertiary amine groups or aryl replace；R2、R3Indicate phenyl, dibiphenylyl, naphthalene, anthryl or phenanthryl.
Above-mentioned electroluminescent organic material, also has the feature that, containing substituent groupContaining substituent group 'sContaining substituent groupWith containing substituent groupFor at least one phenyl ring On by C6-20Phenyl, Unitary replaces, wherein X3、X4、X5Separately Selected from oxygen atom, sulphur atom, selenium atom, two (C1-10Straight chained alkyl) replace season alkyl (or tertiary alkyl), two (C1-10Branched alkane Base) replace season alkyl (or tertiary alkyl), aryl replace season alkyl (or tertiary alkyl), alkyl-substituted tertiary amine groups or aryl take One of the tertiary amine groups in generation.
Above-mentioned electroluminescent organic material, also has the feature that, Ar be selected from phenyl, dibiphenylyl, terphenyl, One of naphthalene, anthryl or phenanthryl.
Above-mentioned electroluminescent organic material, also has the feature that, containing substituent groupContaining taking Dai Ji'sContaining substituent groupWith containing substituent groupFor at least one benzene Quilt on ring Ortho position unitary replaces, i.e., above-mentioned substituent group can pass through C1-C2、C2- C3、C3-C4、C4-C5、C1′-C2′、C2′-C3′、C3′-C4′Or C4′-C5′Key connection.
Above-mentioned electroluminescent organic material, also has the feature that, containing substituent groupReplace with containing BaseIn quilt at least one phenyl ringReplace, andPass through C4-C5Or C4'-C5'Key connects When connecing, X1And X2Overlapping, only take X1Or X2。
Preferably, R in the present invention1It is preferably as follows
Any one of.
Preferably, above-mentioned electroluminescent organic material is preferably any one in following C1-C90 compound in the present invention It is a:
The above are some specific structure types, but fluorenyl Anthraquinones electroluminescent organic material provided in the present invention is not These listed chemical structures are confined to, all based on formula (I) or formula (II), substituent group is base in all ranges of definition The compound of the simple transformation of group should be all included.
The second aspect of the invention is to provide the preparation method of above-mentioned electroluminescent organic material, has such spy Sign, synthetic route are as follows:
The preparation of electroluminescent organic material includes C-N coupling and C-C coupling in the present invention, wherein the method for C-N coupling Are as follows: it is 1:(1.0-2.0 that molar ratio is packed into reaction flask) bromo fluorenyl anthraquinone compounds, amine compound, it is dissolved with toluene, Add Pd2(dba)3, tri-tert phosphorus, sodium tert-butoxide, under an inert atmosphere, by the mixed solution of above-mentioned reactant in 95- 100 DEG C reaction 10-24 hours, stop reaction after through cooling, filtering, column chromatograph, obtain electroluminescent organic material, wherein Pd2 (dba)3, tri-tert phosphorus, sodium tert-butoxide and bromo fluorenyl anthraquinone compounds molar ratio be (0.006-0.02): (0.006- 0.02):(1.0-3.0):1；
The method of C-C coupling are as follows: fluorenyl anthraquinone borate, bromine of the molar ratio for 1:(1.0-2.0) are packed into reaction flask It for compound, is dissolved with toluene, adds Pd2(dba)3, tri-tert phosphorus, sodium tert-butoxide under an inert atmosphere will be above-mentioned anti- Answer the mixed solution of object in 95-100 DEG C reaction 10-24 hours, stop reaction after through cooling, filtering, column chromatograph, obtain Organic Electricity Electroluminescent material, wherein Pd2(dba)3, tri-tert phosphorus, sodium tert-butoxide and bromo fluorenyl anthraquinone compounds molar ratio be (0.006-0.02):(0.006-0.02):(1.0-3.0):1。
The third aspect of the invention is to provide above-mentioned electroluminescent organic material in preparing organic electroluminescence device Application.
The fourth aspect of the invention is to provide a kind of organic electroluminescence device, contains in the organic electroluminescence device Multiple functional layers, also have the feature that, at least one functional layer contains above-mentioned electroluminescent organic material.
Prepared organic electroluminescence device generally comprises the ITO Conducting Glass being sequentially overlapped, sky in the present invention Cave transport layer, luminescent layer (being related to fluorenyl Anthraquinones electroluminescent organic material provided in the present invention), electron transfer layer, electronics Implanted layer (LiF) and cathode layer (Al), all functional layers are all made of vacuum evaporation process and are made.
It should be appreciated that making the purpose of OLED device in the present invention, it is intended merely to be better described, it is provided in the present invention Electroluminescent ability possessed by fluorenyl Anthraquinones electroluminescent organic material, and be not to Organic Electricity provided by the present invention The limitation of the application range of electroluminescent material.
The beneficial effect of above scheme is:
Fluorenyl Anthraquinones electroluminescent organic material provided by the invention is applied in OLED luminescent device, so that device Current efficiency, power efficiency and external quantum efficiency are greatly improved.Fluorenyl Anthraquinones organic electroluminescence hair provided by the invention Luminescent material has good application effect, has good industrialization prospect.
Detailed description of the invention
Fig. 1 is the structural schematic diagram of organic electroluminescence device provided in the embodiment of the present invention, by lower layer to upper layer, It is followed successively by transparent substrate layer (1), transparent electrode layer (2), hole injection layer (3), hole transmission layer (4), luminescent layer (5), electronics Transport layer (6), electron injecting layer (7), cathode reflection electrode layer (8), wherein luminescent layer (5) is related to provided in the present invention Fluorenyl Anthraquinones electroluminescent organic material.
Specific embodiment
Following will be combined with the drawings in the embodiments of the present invention, and technical solution in the embodiment of the present invention carries out clear, complete Site preparation description, it is clear that described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.It is based on Embodiment in the present invention, those of ordinary skill in the art without creative labor it is obtained it is all its His embodiment, shall fall within the protection scope of the present invention.
It should be noted that in the absence of conflict, the feature in embodiment and embodiment in the present invention can phase Mutually combination.
The present invention will be further explained below with reference to the attached drawings and specific examples, but not as the limitation of the invention.
The preparation of 1 compound C01 of embodiment
In the there-necked flask of 250ml, lead under nitrogen protection, 0.01mol compound A1,0.01mol compound B01 be added, 0.015mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 100ml toluene is heated to reflux 10 hours, natural cooling filtered, and filtrate revolving, column chromatographs to obtain target product, HPLC purity 99.8%, yield 76.2%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C47H31NO2, theoretical value 641.2355, test value 641.2356。
Elemental analysis (C47H31NO2): theoretical value C, 87.96；H,4.87；N,2.18；O, 4.99, test value: C, 88.04； H,4.84；N,2.16；O,4.96.
The preparation of 2 compound C07 of embodiment
In the there-necked flask of 250ml, lead under nitrogen protection, 0.01mol compound A1,0.01mol compound B02 be added, 0.015mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 100ml toluene is heated to reflux 10 hours, natural cooling filtered, and filtrate revolving, column chromatographs to obtain target product, HPLC purity 99.9%, yield 62.5%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C51H32N2O2, theoretical value 704.2464, test value 704.2462。
Elemental analysis (C51H32N2O2), theoretical value C:86.91, H:4.58, N:3.97, O:4.54, test value: C:86.90, H:4.58, N:3.98, O:4.54.
The preparation of 3 compound C10 of embodiment
In the there-necked flask of 250ml, lead under nitrogen protection, 0.01mol compound A1,0.01mol compound B03 be added, 0.015mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 100ml toluene is heated to reflux 10 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 99.6%, yield 70.6%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C44H31NO2, theoretical value 605.2355, test value 605.2358。
Elemental analysis (C44H31NO2), theoretical value C:87.25, H:5.16, N:2.31, O:5.28, test value: C:87.24, H:5.16, N:2.30, O:5.30.
The preparation of 4 compound C17 of embodiment
In the there-necked flask of 250ml, lead under nitrogen protection, 0.01mol compound A1,0.01mol compound B04 be added, 0.015mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 100ml toluene is heated to reflux 10 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 99.7%, yield 61.7%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C41H25NO3, theoretical value 579.1834, test value 579.1835。
Elemental analysis (C41H25NO3), theoretical value C:84.96, H:4.35, N:2.42, O:8.28, test value: C:84.96, H:4.35, N:2.42, O:8.28.
The preparation of 5 compound C19 of embodiment
In the there-necked flask of 250ml, lead under nitrogen protection, 0.01mol compound A1,0.01mol compound B05 be added, 0.015mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 100ml toluene is heated to reflux 10 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 99.6%, yield 67.8%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C39H25NO2, theoretical value 539.1885, test value 539.1883。
Elemental analysis (C39H25NO2), theoretical value C:86.80, H:4.67, N:2.60, O:5.39, test value: C:86.82, H:4.67, N:2.59, O:2.38.
The preparation of 6 compound C23 of embodiment
In the there-necked flask of 250ml, lead under nitrogen protection, 0.01mol compound A2,0.01mol compound B06 be added, 0.015mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 100ml toluene is heated to reflux 10 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 99.8%, yield 68.2%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C45H29NO2, theoretical value 615.2198, test value 615.2197。
Elemental analysis (C48H41NO), theoretical value C:90.40, H:4.90, N:2.20, O:2.51, test value: C:90.36, H:4.88, N:2.23, O:2.53.
The preparation of 7 compound C26 of embodiment
In the there-necked flask of 250ml, lead under nitrogen protection, 0.01mol compound A2,0.01mol compound B07 be added, 0.015mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 100ml toluene is heated to reflux 10 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 99.6%, yield 60.1%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C53H34N2O2, theoretical value 730.2620, test value 730.2622。
Elemental analysis (C53H34N2O2), theoretical value C:81.10, H:4.69, N:3.83, O:4.38, test value: C:81.11, H:4.69, N:3.82, O:4.38.
The preparation of 8 compound C29 of embodiment
In the there-necked flask of 250ml, lead under nitrogen protection, 0.01mol compound A2,0.01mol compound B08 be added, 0.015mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 100ml toluene is heated to reflux 10 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 99.9%, yield 64.8%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C50H35NO2, theoretical value 681.2668, test value 681.2667。
Elemental analysis (C50H35NO2), theoretical value C:88.08, H:5.17, N:2.05, O:4.69, test value: C:88.09, H:5.17, N:2.04, O:4.69.
The preparation of 9 compound C35 of embodiment
In the there-necked flask of 250ml, lead under nitrogen protection, 0.01mol compound A2,0.01mol compound B09 be added, 0.015mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 100ml toluene is heated to reflux 10 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 99.6%, yield 61.7%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C50H35NO2, theoretical value 655.2147, test value 655.2146。
Elemental analysis (C50H35NO2), theoretical value C:86.09, H:4.46, N:2.14, O:7.32, test value: C:86.10, H:4.45, N:2.14, O:7.32.
The preparation of 10 compound C42 of embodiment
In the there-necked flask of 250ml, lead under nitrogen protection, 0.01mol compound A2,0.01mol compound B-11 0 be added, 0.015mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 100ml toluene is heated to reflux 10 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 99.9%, yield 67.8%.High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C41H27NO3, theoretical value 581.1991, survey Examination value 581.1992.
Elemental analysis (C41H27NO3), theoretical value C:84.66, H:4.68, N:2.41, O:8.25, test value: C:84.67, H:4.68, N:2.40, O:8.25.
The preparation of 11 compound C57 of embodiment
In the there-necked flask of 250ml, lead under nitrogen protection, 0.01mol compound A1,0.01mol compound B-11 1 be added, 0.015mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 100ml toluene is heated to reflux 10 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 99.7%, yield 65.7%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C44H31NO3, theoretical value 621.2304, test value 621.2302。
Elemental analysis (C44H31NO3), theoretical value C:85.00, H:5.03, N:2.25, O:7.72, test value: C:85.01, H:5.02, N:2.25, O:7.72.
The preparation of 12 compound C66 of embodiment
In the there-necked flask of 250ml, lead under nitrogen protection, 0.01mol compound A1,0.01mol compound B-11 2 be added, 0.015mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 100ml toluene is heated to reflux 10 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 99.8%, yield 66.8%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C44H31NO3, theoretical value 621.2304, test value 621.2305。
Elemental analysis (C44H31NO3), theoretical value C:85.00, H:5.03, N:2.25, O:7.72, test value: C:85.02, H:5.01, N:5.03, O:7.72.
The preparation of 13 compound C68 of embodiment
In the there-necked flask of 250ml, lead under nitrogen protection, 0.01mol compound A1,0.01mol compound B-11 3 be added, 0.015mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 100ml toluene is heated to reflux 10 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 99.8%, yield 65.8%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C53H35N3O2, theoretical value 745.2729, test value 745.2728。
Elemental analysis (C53H35N3O2), theoretical value C:85.35, H:4.73, N:5.63, O:4.29, test value: C:85.36, H:4.72, N:5.63, O:4.29.
The preparation of 14 compound C74 of embodiment
In the there-necked flask of 250ml, lead under nitrogen protection, 0.01mol compound A1,0.01mol compound B-11 4 be added, 0.015mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 100ml toluene is heated to reflux 10 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 99.9%, yield 64.1%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C47H30N2O3, theoretical value 670.2256, test value 670.2257。
Elemental analysis (C47H30N2O3), theoretical value C:84.16, H:4.51, N:4.18, O:7.16, test value: C:84.16, H:4.52, N:4.17, O:7.16.
The preparation of 15 compound C78 of embodiment
In the there-necked flask of 250ml, lead under nitrogen protection, 0.01mol compound A1,0.01mol compound B-11 5 be added, 0.015mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 100ml toluene is heated to reflux 10 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 99.6%, yield 59.8%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C50H36N2O2, theoretical value 696.2777, test value 696.2772。
Elemental analysis (C50H36N2O2), theoretical value C:86.18, H:5.21, N:4.02, O:4.59, test value: C:86.18, H:5.21, N:4.03, O:5.60.
The preparation of 16 compound C81 of embodiment
In the there-necked flask of 250ml, lead under nitrogen protection, 0.01mol compound A1,0.01mol compound B-11 6 be added, 0.015mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 100ml toluene is heated to reflux 10 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 99.9%, yield 68.6%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C41H26N2O3, theoretical value 594.1943, test value 594.1942。
Elemental analysis (C41H26N2O3), theoretical value C:82.81, H:4.41, N:4.71, O:8.07, test value: C:82.81, H:4.41, N:4.71, O:8.07.
The preparation of 17 compound C82 of embodiment
In the there-necked flask of 250ml, lead under nitrogen protection, 0.01mol compound A1,0.01mol compound B-11 7 be added, 0.015mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 100ml toluene is heated to reflux 10 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 99.7%, yield 67.5%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C48H33NO2, theoretical value 655.2511, test value 655.2512。
Elemental analysis (C48H33NO2), theoretical value C:87.91, H:5.07, N:2.14, O:4.88, test value: C:87.91, H:5.07, N:2.14, O:4.88.
The preparation of 18 compound C90 of embodiment
In the there-necked flask of 250ml, lead under nitrogen protection, addition 0.01mol compound 1,0.01mol compound B-11 8, 0.015mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert phosphorus, 100ml toluene is heated to reflux 10 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, column chromatograph to obtain target product, HPLC purity 99.3%, yield 63.8%.
High resolution mass spectrum, the source ESI, positive ion mode, molecular formula C49H31NO2, theoretical value 665.2355, test value 665.2354。
Elemental analysis (C49H31NO2), theoretical value C:88.40, H:4.69, N:2.10, O:4.81, test value: C:88.41, H:4.68, N:2.10, O:4.81.
The above-mentioned compound 10 prepared, compound 57 and current material CBP carry out hot property, luminescent spectrum, glimmering The test of photo-quantum efficiency and cyclic voltammetric stability, as a result as shown in the table:
Compound Tg(℃) Td(℃) λPL(nm) Φ f (%) Cyclic voltammetric stability
Compound 10 130 365 562 61.2 It is excellent
Compound 57 136 372 542 60.8 It is excellent
Material C BP 113 353 369 26.1 Difference
By upper table data it is found that fluorenyl Anthraquinones electroluminescent organic material provided by the invention has suitable HOMO energy Grade and higher thermal stability, are suitable as the material of main part of luminescent layer.
Organic electroluminescence device embodiment
Device 1-6 is prepared with the above-mentioned electroluminescent organic material in part in the embodiment of the present invention 19-24, should be managed Solution, device implementation process with as a result, being intended merely to preferably explain the present invention, not limitation of the present invention, above-mentioned Organic Electricity Electroluminescence device the preparation method is as follows:
A) neutralizing treatment, pure water, drying are successively carried out to ito anode layer (film thickness 150nm), then carries out ultraviolet light- Ozone washing is to remove the organic residue on 2 surface of transparent ITO-anode layer.
B) hole injection layer (MoO3) is deposited on ito anode layer, film thickness 10nm；
C) hole transmission layer (TAPC) is deposited on hole injection layer, film thickness 140nm；
D) on the hole transport layer be deposited luminescent layer (compound provided by the invention: Ir (pq) 2acac=100:5 (wt: Wt), film thickness 30nm；
E) electron transfer layer (TPBI) is deposited on the light-emitting layer, film thickness 50nm；
F) electron injecting layer device (LiF) is deposited on the electron transport layer, film thickness 1nm；
G) evaporation cathode reflection electrode layer (Al) on electron injecting layer, film thickness 80nm.
In the preparation method of above-mentioned organic electroluminescence device, the structural formula of TAPC, Ir (pq) 2acac, TPBI, CBP is such as Shown in lower:
As above after completing device 1-6 and comparative device, anode and cathode is connected with well known driving circuit, is measured The principal structural layer and test knot of the service life of the current efficiency of device, luminescent spectrum and device, device 1-6 and comparative device 1 Fruit is as shown in the table:
In above-mentioned test, using comparative example as reference, comparative example device performance indexes is set as device detection performance 1.0.The current efficiency of comparative example is 14.8cd/A (@10mA/cm2)；CIE chromaticity coordinates is (0.66,0.33)；Under 3000 brightness LT95 life time decay is 11Hr.Life-span test system is the OLED device of owner of the invention and Shanghai University's joint development Life-span tester.
By upper table analysis it is found that fluorenyl Anthraquinones electroluminescent organic material provided by the present invention is as the layer main body that shines The efficiency of OLED luminescent device obtained by material and starting voltage obtain larger change, especially device than known OLED material Efficiency roll-off under part high current density is improved.Fluorenyl Anthraquinones electroluminescent organic material provided by the present invention exists There is good application effect in OLED luminescent device, there is good industrialization prospect.
The above is only preferred embodiments of the present invention, are not intended to limit the implementation manners and the protection scope of the present invention, right For those skilled in the art, it should can appreciate that and all replace with being equal made by description of the invention and diagramatic content It changes and obviously changes obtained scheme, should all be included within the scope of the present invention.

Claims (4)

1. a kind of fluorenyl Anthraquinones electroluminescent organic material, which is characterized in that the electroluminescent organic material is with fluorenyl anthracene Quinone is parent nucleus, shown in structural formula such as formula (I):
Wherein R1 is selected from one of following building stone:
Wherein * represents connection site.
2. a kind of preparation method of electroluminescent organic material according to claim 1, which is characterized in that its synthetic route Are as follows:
3. a kind of fluorenyl Anthraquinones electroluminescent organic material according to claim 1 is preparing organic electroluminescence device In application.
4. a kind of organic electroluminescence device, including multiple functional layers, which is characterized in that at least one described functional layer contains Fluorenyl Anthraquinones electroluminescent organic material described in claim 1.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102329210A (en) * 2011-10-12 2012-01-25 中国科学院上海光学精密机械研究所 2, 6-di(aryl)-anthraquinone and preparation method thereof
TW201504392A (en) * 2013-06-21 2015-02-01 Univ Kyushu Nat Univ Corp Red light-emitting material, organic electroluminescence device and compound
CN105482813A (en) * 2015-12-21 2016-04-13 南京邮电大学 Novel fluorene bipolar fluorescent material based on anthraquinone group and application of novel fluorene bipolar fluorescent material in organic light emitting diodes
CN106083694A (en) * 2016-05-30 2016-11-09 山西大学 A kind of 3,6 2 (anthraquinone 2 vinyl) N ethyl carbazole and preparation method thereof

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CN102329210A (en) * 2011-10-12 2012-01-25 中国科学院上海光学精密机械研究所 2, 6-di(aryl)-anthraquinone and preparation method thereof
TW201504392A (en) * 2013-06-21 2015-02-01 Univ Kyushu Nat Univ Corp Red light-emitting material, organic electroluminescence device and compound
CN105482813A (en) * 2015-12-21 2016-04-13 南京邮电大学 Novel fluorene bipolar fluorescent material based on anthraquinone group and application of novel fluorene bipolar fluorescent material in organic light emitting diodes
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