CN109053784A - A kind of electroluminescent organic material and the preparation method and application thereof - Google Patents

A kind of electroluminescent organic material and the preparation method and application thereof Download PDF

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CN109053784A
CN109053784A CN201811062363.2A CN201811062363A CN109053784A CN 109053784 A CN109053784 A CN 109053784A CN 201811062363 A CN201811062363 A CN 201811062363A CN 109053784 A CN109053784 A CN 109053784A
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alkyl
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CN109053784B (en
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王亚龙
薛震
李红燕
王金平
高昌轩
陈志伟
李林刚
王卫军
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Abstract

The invention belongs to field of light emitting materials, and in particular to a kind of electroluminescent organic material and the preparation method and application thereof.The general structure of electroluminescent organic material of the present invention is shown in formula I:Electroluminescent organic material of the present invention is the derivative using carbazole as core, can be used as electroluminescent layer material in organic electroluminescence device.Each compound provided by the present invention has high fluorescence quantum efficiency, electron hole transmission balance, and exciton high efficiency composition can shine in luminescent layer, and equivalent device luminous efficiency is high, roll-offs small, can be widely applied to electroluminescent field.

Description

A kind of electroluminescent organic material and the preparation method and application thereof
Technical field
The invention belongs to field of light emitting materials, and in particular to a kind of electroluminescent organic material and preparation method thereof with answer With.
Background technique
Electroluminescent organic material is big with light path range, be easy to get to blue light, brightness is big, high-efficient, driving voltage is low, consumption Can less, manufacture craft is simple and the lot of advantages such as at low cost, thin film transistor (TFT), solar battery, non-linear luminescent material, Polymer LED etc. has great application prospect.Thus, electroluminescent organic material receives scientific circles and production The favor of industry becomes very popular one of scientific research task.Although numerous country's investment huge funds are dedicated to organic flat in the world The research and development of plate display device, but its industrialization process, also well below the expectation of people, main cause is that device exists The problems such as service life is short, brightness is low and low efficiency.
Summary of the invention
The purpose of the present invention is to provide a kind of electroluminescent organic materials and preparation method thereof, are preparing Organic Electricity with it Application in the luminescent layer of electroluminescence device solves the problems such as existing luminescent material device lifetime is short, brightness is low, low efficiency.
Realization process of the invention is as follows:
A kind of electroluminescent organic material, general structure are shown in formula I:
In Formulas I, X is N or B；
Ar1、Ar2、Ar3、Ar4、Ar5It is identical or different,
Ar1、Ar2、Ar3、Ar4、Ar5It is selected from any one in aryl or substituted aryl, the aryl is phenyl, condensed ring virtue Perfume base, heterocyclic aryl, two aromatic aminos, the substituent group are alkyl, alkoxy, alkylthio group, cyano, halogen, amino, heterocycle virtue Base, polyaromatic, two aromatic aminos；
R1、R2It is identical or different,
R1、R2Be selected from hydrogen atom, alkyl, naphthenic base, substituted cycloalkyl, Heterocyclylalkyl, substituted heterocycle alkyl, alkoxy, Alkylthio group, cyano, amino, halogen, phenyl, C10-C30 polycyclic aromatic base, C5-C30 heterocyclic aryl, the substituent group are C1- C30 alkyl, C1-C30 alkoxy, C1-C30 alkylthio group, cyano, halogen, amino, two aromatic aminos.
Further, the Ar1、Ar2、Ar3、Ar4、Ar5It is selected from phenyl or substituted-phenyl, naphthalene or substituted naphthyl, quinoline Base or substd quinolines base；The substituent group be carbon atom number be 1-6 alkyl, carbon atom number be 1-6 alkoxy, carbon atom number For the alkylthio group of 1-6, cyano, halogen, amino, hexichol amido, carbon atom number be 1-6 alkyl-substituted diphenylamine base, dinaphthylamine Base, the alkyl that carbon atom number is 1-6 replace dinaphthyl amido, two quinoline amidos, quinolyl, and the alkyl that carbon atom number is 1-6 replaces Quinolyl, halogen substd quinolines base, the alkoxy substd quinolines base that carbon atom number is 1-6；
R1、R2It is selected from hydrogen atom, the alkoxy that the alkyl that carbon atom number is 1-6, halogen, carbon atom number are 1-6, carbon original Subnumber is the naphthenic base of 3-10, alkyl-substituted cycloalkyl, halogen substituted cycloalkyl, cyano substituted cycloalkyl, epoxy alkyl, halogen Substituted epoxy alkyl, amino substituted epoxy alkyl, alkyl substituted epoxy alkyl, alkoxy substituted epoxy alkyl, cyano replace ring Oxyalkyl, carbon atom number be the alkylthio group of 1-6, cyano, phenyl, alkyl-substituted phenyl, halogen substituted phenyl, alkoxy substituted Base, cyano substituted-phenyl, amino substituted-phenyl, hexichol amido substituted-phenyl, pyridyl group, alkyl substituted pyridines base, halogen replace Pyridyl group, cyano substituted pyridinyl, alkoxy substituted pyridinyl, hexichol amido substituted pyridinyl, naphthalene, alkyl-substituted naphthaline base, Alkoxy substituted naphthyl, cyano substituted naphthyl, hexichol amido substituted naphthyl, halogen substituted naphthyl, hexichol amido, quinolyl, alkane Base substd quinolines base, halogen substd quinolines base, alkoxy substd quinolines base, cyano substd quinolines base, hexichol amido substd quinolines Base, amino.
Further, the electroluminescent organic material is in following compound:
Further, the Ar3、Ar4、Ar5It is selected from phenyl or substituted-phenyl, naphthalene or substituted naphthyl, quinolyl or substitution Quinolyl；The substituent group be carbon atom number be 1-6 alkyl, carbon atom number be 1-6 alkoxy, carbon atom number be 1-6's The alkyl-substituted diphenylamine base, dinaphthyl amido, carbon that alkylthio group, cyano, halogen, amino, hexichol amido, carbon atom number are 1-6 are former Subnumber be 1-6 alkyl replace dinaphthyl amido, two quinoline amidos, quinolyl, carbon atom number be 1-6 alkyl substd quinolines base, Halogen substd quinolines base, the alkoxy substd quinolines base that carbon atom number is 1-6；
R1、R2It is selected from hydrogen atom, the alkoxy that the alkyl that carbon atom number is 1-6, halogen, carbon atom number are 1-6, carbon original Subnumber is the naphthenic base of 3-10, alkyl-substituted cycloalkyl, halogen substituted cycloalkyl, cyano substituted cycloalkyl, epoxy alkyl, halogen Substituted epoxy alkyl, amino substituted epoxy alkyl, alkyl substituted epoxy alkyl, alkoxy substituted epoxy alkyl, cyano replace ring Oxyalkyl, carbon atom number be the alkylthio group of 1-6, cyano, phenyl, alkyl-substituted phenyl, halogen substituted phenyl, alkoxy substituted Base, cyano substituted-phenyl, amino substituted-phenyl, hexichol amido substituted-phenyl, pyridyl group, alkyl substituted pyridines base, halogen replace Pyridyl group, cyano substituted pyridinyl, alkoxy substituted pyridinyl, hexichol amido substituted pyridinyl, naphthalene, alkyl-substituted naphthaline base, Alkoxy substituted naphthyl, cyano substituted naphthyl, hexichol amido substituted naphthyl, halogen substituted naphthyl, hexichol amido, quinolyl, alkane Base substd quinolines base, halogen substd quinolines base, alkoxy substd quinolines base, cyano substd quinolines base, hexichol amido substd quinolines Base, amino；
X is N or B；
Ar1With Ar2For phenyl, Ar1Ortho position and Ar2Ortho position by C-C key or C-L-C connection, structural formula such as Formula II Or shown in formula III:
- the L1Key is-O- ,-S- ,-Si- or-C (R3)2In any one, the R3It is 1-6's selected from carbon atom number Straight chained alkyl.
Further, the electroluminescent organic material is in following compound:
Further, the Ar1、Ar2、Ar5It is selected from phenyl or substituted-phenyl, naphthalene or substituted naphthyl, quinolyl or substitution Quinolyl；The substituent group be carbon atom number be 1-6 alkyl, carbon atom number be 1-6 alkoxy, carbon atom number be 1-6's The alkyl-substituted diphenylamine base, dinaphthyl amido, carbon that alkylthio group, cyano, halogen, amino, hexichol amido, carbon atom number are 1-6 are former Subnumber be 1-6 alkyl replace dinaphthyl amido, two quinoline amidos, quinolyl, carbon atom number be 1-6 alkyl substd quinolines base, Halogen substd quinolines base, the alkoxy substd quinolines base that carbon atom number is 1-6；
R1、R2It is selected from hydrogen atom, the alkoxy that the alkyl that carbon atom number is 1-6, halogen, carbon atom number are 1-6, carbon original Subnumber is the naphthenic base of 3-10, alkyl-substituted cycloalkyl, halogen substituted cycloalkyl, cyano substituted cycloalkyl, epoxy alkyl, halogen Substituted epoxy alkyl, amino substituted epoxy alkyl, alkyl substituted epoxy alkyl, alkoxy substituted epoxy alkyl, cyano replace ring Oxyalkyl, carbon atom number be the alkylthio group of 1-6, cyano, phenyl, alkyl-substituted phenyl, halogen substituted phenyl, alkoxy substituted Base, cyano substituted-phenyl, amino substituted-phenyl, hexichol amido substituted-phenyl, pyridyl group, alkyl substituted pyridines base, halogen replace Pyridyl group, cyano substituted pyridinyl, alkoxy substituted pyridinyl, hexichol amido substituted pyridinyl, naphthalene, alkyl-substituted naphthaline base, Alkoxy substituted naphthyl, cyano substituted naphthyl, hexichol amido substituted naphthyl, halogen substituted naphthyl, hexichol amido, quinolyl, alkane Base substd quinolines base, halogen substd quinolines base, alkoxy substd quinolines base, cyano substd quinolines base, hexichol amido substd quinolines Base, amino；
X is N or B；
Ar3With Ar4For phenyl, Ar3Ortho position and Ar4Ortho position by C-C key or C-L-C connection, structural formula such as Formula II Or shown in formula III:
- the L2Key is-O- ,-S- ,-Si- or-C (R4)2In any one, the R4It is 1-6's selected from carbon atom number Straight chained alkyl.
Further, the electroluminescent organic material is in following compound:
The preparation method of above-mentioned organic photoelectrical material, includes the following steps:
(1) raw material Ia, raw material Ib are dissolved in ortho-xylene, when system is warming up to 150-180 DEG C with oil bath, under stirring By catalystIt is added dropwise in above-mentioned system, 8-12h is stirred to react after dripping off, water is added after cooling, use is dilute HCl tune pH=6, separates organic layer, and water layer is extracted twice with dichloroethanes, merges organic layer, washes through saturated sodium bicarbonate solution It washs twice, is washed with water to neutrality, is dried, filtered through anhydrous magnesium sulfate, filtrate is concentrated to dryness, and obtains intermediate compound I；Reaction equation is such as Under:
(2) in N2Protection under, intermediate compound I is dissolved in tetrahydrofuran, when system is cooled to -78 DEG C, positive fourth is added dropwise Base lithium after insulation reaction 1-2h, is added dropwise the tetrahydrofuran solution of raw material Ic, reacts 1.5-4h, after reaction delay reaction solution Slowly it is poured into water stirring, solid is precipitated, filtered, dry to obtain compound I；Reaction equation is as follows:
Further, the mass fraction of step (1) described dilute hydrochloric acid is 10%；The raw material Ia, raw material Ib, catalyst rub You are than being 1.5:(3-5): (3-5)；The intermediate compound I, n-BuLi, raw material Ic molar ratio be 0.5:(0.8-1): (0.8- 1)。
Application of the above-mentioned electroluminescent organic material in the luminescent layer for preparing organic electroluminescence device.
The positive effect of the present invention: electroluminescent organic material of the present invention has high fluorescence quantum efficiency, electronics Hole transport balance, exciton high efficiency composition can shine in luminescent layer, and equivalent device luminous efficiency is high, roll-offs small, can answer extensively For electroluminescent field.
Detailed description of the invention
Fig. 1 is the hydrogen spectrogram of electroluminescent organic material described in embodiment 1；
Fig. 2 is the hydrogen spectrogram of electroluminescent organic material described in embodiment 2.
Specific embodiment
Below with reference to embodiment, the present invention will be further described.
In order to solve the problems such as existing luminescent material device lifetime is short, brightness is low, low efficiency, the present invention provides a kind of organic Electroluminescent material and preparation method thereof, with its application in the luminescent layer for preparing organic electroluminescence device.
Raw material and reagent used in the present invention are commercially available.
Embodiment 1
The structure of electroluminescent organic material compound 1 described in the present embodiment is as follows:
The preparation method of above-mentioned electroluminescent organic material, includes the following steps:
(1) 0.15mol raw material 1a, 0.3mol raw material 1b is dissolved in 20ml ortho-xylene, system is warming up to oil bath At 160 DEG C, by 0.3mol under stirringIt is added dropwise in above-mentioned system, drips off T=160 DEG C of rear constant temperature stirring 10h is reacted, 15ml water is added after cooling, with 10% dilute HCl tune pH=6, separates organic layer, water layer is extracted with 20ml dichloroethanes Twice, merge organic layer, the sodium bicarbonate solution being saturated through 20ml washes twice, and organic layer is dry with 5g anhydrous magnesium sulfate, mistake Consider, (T=35 DEG C) is concentrated to doing in filtrate, obtains intermediate 1, yield 80%.Reaction equation is as follows:
(2) in N2Protection under, 0.05mol intermediate 1 is dissolved in 5ml tetrahydrofuran, when system is cooled to -78 DEG C, It is slowly added dropwise 0.08mol n-BuLi, after insulation reaction 1h, 0.08mol raw material 1c is added dropwise in 8ml tetrahydrofuran solution, reaction Reaction solution is poured slowly into 10ml water stirs after reaction by 4h, and solid is precipitated, filtered, dry to obtain compound 1；Yield 56%, reaction equation is as follows:
The calculated value C of 1 constituent content of compound42H31BN2: C, 87.80；H,5.44；N,4.88；B,1.88；Measured value: C, 87.78；H,5.42；N,4.83；B,1.85；Hydrogen spectrogram is shown in Fig. 1.Wherein, raw material 1a, raw material 1b, raw material 1c,It is purchase.
Embodiment 2
The structure of electroluminescent organic material compound 2 described in the present embodiment is as follows:
(1) 0.15mol raw material 2a, 0.5mol raw material 2b is dissolved in 20ml ortho-xylene, system is warming up to oil bath At 160 DEG C, by 0.5mol under stirringIt is added dropwise in above-mentioned system, drips off T=160 DEG C of rear constant temperature stirring 10h is reacted, 15ml water is added after cooling, with 10% dilute HCl tune pH=6, separates organic layer, water layer is extracted with 20ml dichloroethanes Twice, merge organic layer, the sodium bicarbonate solution being saturated through 20ml washes twice, and organic layer is dry with 5g anhydrous magnesium sulfate, mistake To consider, (T=35 DEG C) is concentrated to doing in filtrate, intermediate 2 is obtained, yield 80%, reaction equation is as follows:
(2) in N2Protection under, 0.05mol intermediate 2 is dissolved in 5ml tetrahydrofuran, when system is cooled to -78 DEG C, It is slowly added dropwise 0.1mol n-BuLi, after insulation reaction 1h, 0.1mol raw material 2c is added dropwise in 8ml tetrahydrofuran solution, reaction Reaction solution is poured slowly into 10ml water stirs after reaction by 1.5h, and solid is precipitated, filtered, dry to obtain compound 2；It receives Rate 53%；Reaction equation is as follows:
The calculated value C of 2 constituent content of compound46H39BN2: C, 87.61；H,6.23；B,1.71；N,4.44；Measured value: C, 89.63；H,6.21；N,4.42；B,1.68；Hydrogen spectrogram is shown in Fig. 2.Wherein, raw material 2a, raw material 2b, raw material 2c,It is purchase.
Embodiment 3
The structure of electroluminescent organic material compound 3 described in the present embodiment is as follows:
(1) 0.15mol raw material 3a, 0.4mol raw material 3b is dissolved in 20ml ortho-xylene, system is warming up to oil bath At 160 DEG C, by 0.3mol under stirringIt is added dropwise in above-mentioned system, drips off T=160 DEG C of rear constant temperature stirring 10h is reacted, 15ml water is added after cooling, with 10% dilute HCl tune pH=6, separates organic layer, water layer is extracted with 20ml dichloroethanes Twice, merge organic layer, the sodium bicarbonate solution being saturated through 20ml washes twice, and organic layer is dry with 5g anhydrous magnesium sulfate, mistake To consider, (T=35 DEG C) is concentrated to doing in filtrate, intermediate 3 is obtained, yield 89%, reaction equation is as follows:
(2) in N2Protection under, 0.05mol intermediate 3 is dissolved in 5ml tetrahydrofuran, when system is cooled to -78 DEG C, It is slowly added dropwise 0.09mol n-BuLi, after insulation reaction 1h, 0.08mol raw material 3c is added dropwise in 8ml tetrahydrofuran solution, reaction Reaction solution is poured slowly into 10ml water stirs after reaction by 2h, and solid is precipitated, filtered, dry to obtain compound 3；Yield 55%；Reaction equation is as follows:
Embodiment 4-90
The preparation method of embodiment 4-90 is similar to Example 1, the difference is that the substituent group of 3 kinds of raw materials is different, because This, synthesizes compound 4-90 according to the above method, and each compound structure is as follows:
Application of 91 electroluminescent organic material of embodiment in the luminescent layer of organic electroluminescence device
The manufacturing method of organic luminescent device, includes the following steps:
(1) successively first there is tin indium oxide (ITO) electrode (first electrode, anode) with distilled water, methanol ultrasonic cleaning Glass film plates, it is dry；
(2) it is cleaned 5 minutes with oxygen plasma again, the anode bottom plate cleaned up is then loaded into vacuum deposition device In；
(3) HIL of about 50nm thickness will be formed in hole injection layer compound 2-TNATA vacuum deposition to ITO electrode, then The HTL of about 20nm thickness will be formed in hole transmission layer compound N PB vacuum deposition to hole injection layer, it then will be of the invention real The obtained compound of a 1-90 is applied as main body luminescent material and B Alq3Dopant is co-deposited to sky with the mass ratio of 96:4 The luminescent layer EML of about 30nm thickness is formed on the transmission region of cave；
(4) the hole blocking layer DPVBi of about 20nm thickness, the electron transfer layer Alq of about 30nm thickness are finally sequentially depositing3 And the aluminium of cathode LiF and about the 50nm thickness of about 5nm thickness, thus complete the manufacture of organic luminescent device.
Comparative example: BPO, BPO are existing common main body luminescent material, and structural formula is as follows:
BPO, compound 1 to compound 90 are manufactured into corresponding organic luminescent device respectively according to above-mentioned manufacturing method, The electron luminescence characteristic list of manufactured organic luminescent device is shown in Table 1.
The electron luminescence characteristic list of 1 organic luminescent device of table
Thus table, which can be seen that the compound of the present invention 1, can be applied successfully to compound 90 as main body luminescent material In the luminescent layer of organic electroluminescence device.Driving voltage is significantly lower than common main body luminescent material BPO, and in low driving Efficiency all with higher and brightness under voltage.
Electroluminescent organic material of the present invention is the derivative using carbazole as core, can be used as organic electroluminescent Electroluminescent layer material in device.Each compound provided by the present invention has high fluorescence quantum efficiency, electron hole transmission Balance, exciton high efficiency composition can shine in luminescent layer, and equivalent device luminous efficiency is high, roll-offs small, can be widely applied to electroluminescent Illumination field.

Claims (10)

1. a kind of electroluminescent organic material, general structure are shown in formula I:
In Formulas I, X is N or B；
Ar1、Ar2、Ar3、Ar4、Ar5It is identical or different,
Ar1、Ar2、Ar3、Ar4、Ar5It is selected from any one in aryl or substituted aryl, the aryl is phenyl, polycyclic aromatic Base, heterocyclic aryl, two aromatic aminos, the substituent group are alkyl, alkoxy, alkylthio group, cyano, halogen, amino, heterocycle virtue Base, polyaromatic, two aromatic aminos；
R1、R2It is identical or different,
R1、R2It is selected from hydrogen atom, alkyl, naphthenic base, substituted cycloalkyl, Heterocyclylalkyl, substituted heterocycle alkyl, alkoxy, alkane sulphur Base, cyano, amino, halogen, phenyl, C10-C30 polycyclic aromatic base, C5-C30 heterocyclic aryl, the substituent group are C1-C30 alkane Base, C1-C30 alkoxy, C1-C30 alkylthio group, cyano, halogen, amino, two aromatic aminos.
2. electroluminescent organic material according to claim 1, it is characterised in that:
The Ar1、Ar2、Ar3、Ar4、Ar5It is selected from phenyl or substituted-phenyl, naphthalene or substituted naphthyl, quinolyl or substd quinolines Base；The substituent group be carbon atom number be 1-6 alkyl, carbon atom number be 1-6 alkoxy, carbon atom number be 1-6 alkane sulphur Base, cyano, halogen, amino, hexichol amido, alkyl-substituted diphenylamine base, the dinaphthyl amido, carbon atom number that carbon atom number is 1-6 Replace dinaphthyl amido, two quinoline amidos, quinolyl for the alkyl of 1-6, carbon atom number is alkyl substd quinolines base, the halogen of 1-6 Substd quinolines base, the alkoxy substd quinolines base that carbon atom number is 1-6；
R1、R2It is selected from hydrogen atom, the alkoxy that the alkyl that carbon atom number is 1-6, halogen, carbon atom number are 1-6, carbon atom number Replace for the naphthenic base of 3-10, alkyl-substituted cycloalkyl, halogen substituted cycloalkyl, cyano substituted cycloalkyl, epoxy alkyl, halogen Epoxy alkyl, amino substituted epoxy alkyl, alkyl substituted epoxy alkyl, alkoxy substituted epoxy alkyl, cyano substituted epoxy alkane Base, carbon atom number be the alkylthio group of 1-6, cyano, phenyl, alkyl-substituted phenyl, halogen substituted phenyl, alkoxy substituted phenyl, Cyano substituted-phenyl, amino substituted-phenyl, hexichol amido substituted-phenyl, pyridyl group, alkyl substituted pyridines base, halogen substituted pyridines Base, cyano substituted pyridinyl, alkoxy substituted pyridinyl, hexichol amido substituted pyridinyl, naphthalene, alkyl-substituted naphthaline base, alcoxyl Base substituted naphthyl, cyano substituted naphthyl, hexichol amido substituted naphthyl, halogen substituted naphthyl, hexichol amido, quinolyl, alkyl take For quinolyl, halogen substd quinolines base, alkoxy substd quinolines base, cyano substd quinolines base, hexichol amido substd quinolines base, ammonia Base.
3. electroluminescent organic material according to claim 2, which is characterized in that the electroluminescent organic material be selected from In lower compound:
4. electroluminescent organic material according to claim 2, which is characterized in that
The Ar3、Ar4、Ar5It is selected from phenyl or substituted-phenyl, naphthalene or substituted naphthyl, quinolyl or substd quinolines base；It is described Substituent group be carbon atom number be 1-6 alkyl, carbon atom number be 1-6 alkoxy, carbon atom number be 1-6 alkylthio group, cyano, The alkane that alkyl-substituted diphenylamine base that halogen, amino, hexichol amido, carbon atom number are 1-6, dinaphthyl amido, carbon atom number are 1-6 Base replaces dinaphthyl amido, two quinoline amidos, quinolyl, and carbon atom number is alkyl substd quinolines base, the halogen substd quinolines of 1-6 Base, the alkoxy substd quinolines base that carbon atom number is 1-6；
R1、R2It is selected from hydrogen atom, the alkoxy that the alkyl that carbon atom number is 1-6, halogen, carbon atom number are 1-6, carbon atom number Replace for the naphthenic base of 3-10, alkyl-substituted cycloalkyl, halogen substituted cycloalkyl, cyano substituted cycloalkyl, epoxy alkyl, halogen Epoxy alkyl, amino substituted epoxy alkyl, alkyl substituted epoxy alkyl, alkoxy substituted epoxy alkyl, cyano substituted epoxy alkane Base, carbon atom number be the alkylthio group of 1-6, cyano, phenyl, alkyl-substituted phenyl, halogen substituted phenyl, alkoxy substituted phenyl, Cyano substituted-phenyl, amino substituted-phenyl, hexichol amido substituted-phenyl, pyridyl group, alkyl substituted pyridines base, halogen substituted pyridines Base, cyano substituted pyridinyl, alkoxy substituted pyridinyl, hexichol amido substituted pyridinyl, naphthalene, alkyl-substituted naphthaline base, alcoxyl Base substituted naphthyl, cyano substituted naphthyl, hexichol amido substituted naphthyl, halogen substituted naphthyl, hexichol amido, quinolyl, alkyl take For quinolyl, halogen substd quinolines base, alkoxy substd quinolines base, cyano substd quinolines base, hexichol amido substd quinolines base, ammonia Base；
X is N or B；
Ar1With Ar2For phenyl, Ar1Ortho position and Ar2Ortho position by C-C key or C-L-C connection, structural formula such as Formula II or formula Shown in III:
- the L1Key is-O- ,-S- ,-Si- or-C (R3)2In any one, the R3The straight chain alkane for being 1-6 selected from carbon atom number Base.
5. electroluminescent organic material according to claim 4, which is characterized in that the electroluminescent organic material be selected from In lower compound:
6. electroluminescent organic material according to claim 2, which is characterized in that
The Ar1、Ar2、Ar5It is selected from phenyl or substituted-phenyl, naphthalene or substituted naphthyl, quinolyl or substd quinolines base；It is described Substituent group be carbon atom number be 1-6 alkyl, carbon atom number be 1-6 alkoxy, carbon atom number be 1-6 alkylthio group, cyano, The alkane that alkyl-substituted diphenylamine base that halogen, amino, hexichol amido, carbon atom number are 1-6, dinaphthyl amido, carbon atom number are 1-6 Base replaces dinaphthyl amido, two quinoline amidos, quinolyl, and carbon atom number is alkyl substd quinolines base, the halogen substd quinolines of 1-6 Base, the alkoxy substd quinolines base that carbon atom number is 1-6；
R1、R2It is selected from hydrogen atom, the alkoxy that the alkyl that carbon atom number is 1-6, halogen, carbon atom number are 1-6, carbon atom number Replace for the naphthenic base of 3-10, alkyl-substituted cycloalkyl, halogen substituted cycloalkyl, cyano substituted cycloalkyl, epoxy alkyl, halogen Epoxy alkyl, amino substituted epoxy alkyl, alkyl substituted epoxy alkyl, alkoxy substituted epoxy alkyl, cyano substituted epoxy alkane Base, carbon atom number be the alkylthio group of 1-6, cyano, phenyl, alkyl-substituted phenyl, halogen substituted phenyl, alkoxy substituted phenyl, Cyano substituted-phenyl, amino substituted-phenyl, hexichol amido substituted-phenyl, pyridyl group, alkyl substituted pyridines base, halogen substituted pyridines Base, cyano substituted pyridinyl, alkoxy substituted pyridinyl, hexichol amido substituted pyridinyl, naphthalene, alkyl-substituted naphthaline base, alcoxyl Base substituted naphthyl, cyano substituted naphthyl, hexichol amido substituted naphthyl, halogen substituted naphthyl, hexichol amido, quinolyl, alkyl take For quinolyl, halogen substd quinolines base, alkoxy substd quinolines base, cyano substd quinolines base, hexichol amido substd quinolines base, ammonia Base；
X is N or B；
Ar3With Ar4For phenyl, Ar3Ortho position and Ar4Ortho position by C-C key or C-L-C connection, structural formula such as Formula II or formula Shown in III:
- the L2Key is-O- ,-S- ,-Si- or-C (R4)2In any one, the R4The straight chain alkane for being 1-6 selected from carbon atom number Base.
7. electroluminescent organic material according to claim 6, which is characterized in that the electroluminescent organic material be selected from In lower compound:
The preparation method of electroluminescent organic material described in 8. claim 1 to 7 is one of any, which is characterized in that including as follows Step:
(1) raw material Ia, raw material Ib are dissolved in ortho-xylene, when system is warming up to 150-180 DEG C with oil bath, will be urged under stirring AgentIt is added dropwise in above-mentioned system, 8-12h is stirred to react after dripping off, water is added after cooling, with dilute HCl PH=6 is adjusted, organic layer is separated, water layer is extracted twice with dichloroethanes, merges organic layer, through saturated sodium bicarbonate solution washing two It is secondary, it is washed with water to neutrality, is dried, filtered through anhydrous magnesium sulfate, filtrate is concentrated to dryness, and obtains intermediate compound I；Reaction equation is as follows:
(2) in N2Protection under, intermediate compound I is dissolved in tetrahydrofuran, when system is cooled to -78 DEG C, be added dropwise n-BuLi, After insulation reaction 1-2h, the tetrahydrofuran solution of raw material Ic is added dropwise, reacts 1.5-4h, is after reaction poured slowly into reaction solution It is stirred in water, solid is precipitated, filtered, dry to obtain compound I；Reaction equation is as follows:
9. the preparation method of electroluminescent organic material according to claim 8, it is characterised in that: step (1) dilute salt The mass fraction of acid is 10%；The raw material Ia, raw material Ib, catalyst molar ratio be 1.5:(3-5): (3-5)；The centre Body I, n-BuLi, raw material Ic molar ratio be 0.5:(0.8-1): (0.8-1).
10. electroluminescent organic material described in claim 1 to 7 is one of any is in the luminescent layer for preparing organic electroluminescence device In application.
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