CN109970575A - Organic electroluminescent compounds and its preparation method and application - Google Patents

Organic electroluminescent compounds and its preparation method and application Download PDF

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CN109970575A
CN109970575A CN201910323028.1A CN201910323028A CN109970575A CN 109970575 A CN109970575 A CN 109970575A CN 201910323028 A CN201910323028 A CN 201910323028A CN 109970575 A CN109970575 A CN 109970575A
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organic
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CN109970575B (en
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马晓宇
王永光
汪康
姚明明
李文军
李贺
毕岩
王进政
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The invention belongs to technical field of organic luminescence materials, and in particular to a kind of organic electroluminescent compounds and its preparation method and application.Organic electroluminescent compounds structural formula of the invention is as described in chemical formula 1:

Description

Organic electroluminescent compounds and its preparation method and application
Technical field
The invention belongs to technical field of organic luminescence materials, and in particular to a kind of organic electroluminescent compounds and its preparation method And application.
Background technique
Organic electroluminescent device is the self-emission device that following principle is utilized: by applying electric field, using by anode Injected holes makes fluorescent substance shine with the recombination energy by cathode injected electrons.It has the following structure: anode, cathode And the organic material layer to fall between.In order to improve the efficiency and stability of organic electroluminescent device, organic material Layer includes having the multilayer of different materials, such as hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electronics are infused Enter layer etc..When applying voltage between the anode and cathode, the hole from anode and the organic material of the electron injection from cathode The bed of material, the exciton of generation generate the light with specific wavelength when migrating to ground state.
The most important factor for determining Organnic electroluminescent device luminous efficiency is luminescent material.Up to the present, phosphor Material has been widely used as luminescent material.However, in view of electroluminescent mechanism, due to phosphor material theoretically with fluorescent material phase Than making luminous efficiency enhance four times, therefore the exploitation of phosphorescent light-emitting materials is widely studied.Iridium (III) complex compound is widely Referred to as phosphorescence dopant material.Currently, 4 ,-two carbazoles of 4 '-N, N '-biphenyl (CBP), (2- naphthalene) anthracene of 9,10- bis- (ADN) etc. are made It is widely used for known phosphorescent light body material.Although these materials provide good luminous feature, with following Disadvantage: (1) due to its lower glass transition temperature and bad thermal stability, lead to the service life reduction of device.It (2) include phosphorescence The Organnic electroluminescent device of material of main part needs higher driving voltage.Meanwhile in order to improve Organnic electroluminescent device Efficiency and stability need it to have comprising hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injection The multilayered structure of layer.Hole can be changed to the hole transport efficiency, luminous efficiency, service life etc. of luminescent layer in its hole-transporting layer. Therefore, using copper phthalocyanine (CuPc), 4,4 '-bis- [N- (1- naphthalene)-N- phenyl amino] biphenyl (NPB), N, N '-diphenyl-N, Bis- (3- aminomethyl phenyl)-(1,1 '-biphenyl) -4,4 '-diamines (TPD) of N '-etc. are used as hole mobile material.However, using these The Organnic electroluminescent device of material is also less desirable in terms of quantum efficiency and service life.
Summary of the invention
The object of the present invention is to provide a kind of organic electroluminescence with splendid current efficiency and power efficiency and long-life Luminophor and its preparation method and application.
To achieve the goals above, technical solution of the present invention is specific as follows:
A kind of organic electroluminescent compounds, structural formula are shown in chemical formula 1:
Wherein:
Ar1And Ar2It each independently represents the C1-C30 alkyl for being substituted or being unsubstituted, be substituted or be unsubstituted C6-C30 aryl or 3 to 30 unit's heteroaryls for being substituted or being unsubstituted；Or it is connect with adjacent substituents and to form monocycle or polycyclic C3-C30 aliphatic ring or aromatic ring, the replaceable hetero atom that nitrogen, oxygen or sulphur are selected from least one of carbon atom；
R0For hydrogen or deuterium；T indicates 0 to 4 integer；
R1And R2It each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, amido, be substituted or without taking The C1-C30 alkyl in generation, the C2-C30 alkenyl for being substituted or being unsubstituted, the C2-C30 alkynyl for being substituted or being unsubstituted, through taking Generation or the C1-C30 alkoxy being unsubstituted, are substituted or are unsubstituted the C3-C30 naphthenic base for being substituted or being unsubstituted C3-C30 cycloalkenyl, 3 to 7 membered heterocycloalkyls for being substituted or being unsubstituted, the C6-C30 aryl for being substituted or being unsubstituted or 3 to 30 unit's heteroaryls for being substituted or being unsubstituted；Or the monocycle to be formed and be substituted or be unsubstituted is connect with adjacent substituents Or polycyclic C3-C30 aliphatic ring or aromatic ring, the replaceable hetero atom that nitrogen, oxygen or sulphur are selected from least one of carbon atom；
X is-O- ,-S- ,-C (R5)(R6)-、-N(R7)-or-Si (R8)(R9)-, Y is-[C (R3)c(R4)d]m-；
R3To R9Each independently represent the C1-C30 alkyl for being substituted or being unsubstituted, the C2- for being substituted or being unsubstituted C30 alkenyl, the C2-C30 alkynyl for being substituted or being unsubstituted, the C1-C30 alkoxy for being substituted or being unsubstituted, be substituted or The C3-C30 naphthenic base that is unsubstituted, be substituted or be unsubstituted C3-C30 cycloalkenyl, be substituted or be unsubstituted 3 to 7 Membered heterocycloalkyl, the C6-C30 aryl for being substituted or being unsubstituted or 3 to 30 unit's heteroaryls for being substituted or being unsubstituted；Or with Adjacent substituents connect to form the monocycle for being substituted or being unsubstituted or polycyclic C3-C30 aliphatic ring or aromatic ring, and carbon is former The replaceable hetero atom that nitrogen, oxygen or sulphur are selected from least one of son；
Q ring indicates the C6-C30 aryl for being substituted or being unsubstituted or 3 to 30 unit's heteroaryls for being substituted or being unsubstituted；
G ring indicate be substituted or be unsubstituted C3-C30 naphthenic base, be substituted or be unsubstituted C3-C30 cycloalkenyl, 3 to 7 membered heterocycloalkyls that are substituted or are unsubstituted, the C6-C30 aryl for being substituted or being unsubstituted are substituted or without taking 3 to 30 unit's heteroaryls in generation；
A, b each independently represents 0 to 4 integer, and c, d each independently represent 0 to 2 integer, and m and n are respectively independent When ground indicates that 0 or 1 and n is 1, m is 0 or 1；When n is 0, R1It can be substituted or not with the G ring being connected formation has been shown in general formula The polycyclic C3-C30 aliphatic ring or aromatic ring being substituted, carbon atom are replaceable in the hetero atoms such as nitrogen, oxygen, sulphur and silicon One or more.
In the above-mentioned technical solutions, preferably Ar1And Ar2Each independently represent any one in following structures:
It is preferred thatPart be following structures in any one:
In above structure, R be hydrogen, halogen, cyano, the alkyl of C1-C30, the aryl of C6-C50, C7-C50 aralkyl, Alkoxy aryl, the aryl alkane sulfydryl of C7-C50 or the heteroaryl of C5-C50 of C7-C50；
Wherein, the alkyl be straight chained alkyl, branched alkyl, naphthenic base, at least one substituent group replace straight chained alkyl, The naphthenic base that the branched alkyl or at least one substituent group that at least one substituent group replaces replace；Wherein, the substituent group is independent Selected from one or more of halogen, cyano, hydroxyl and sulfydryl.
The aryl is preferably the aryl that unsubstituted aryl or at least one substituent group replace；Wherein, the substituent group is only Vertical selection halogen, amino, cyano, nitro, hydroxyl or sulfydryl；
The aryl alkyl is preferably the aryl alkyl that unsubstituted aryl alkyl or at least one substituent group replace；Wherein, The independent selection halogen of the substituent group, amino, cyano, nitro, hydroxyl or sulfydryl；
The alkoxy aryl is preferably the arylalkoxy that unsubstituted alkoxy aryl or at least one substituent group replace Base；Wherein, the independent selection halogen of the substituent group, amino, cyano, nitro, hydroxyl or sulfydryl；
The aryl alkane sulfydryl is preferably the aryl alkane mercapto that unsubstituted aryl alkane sulfydryl or at least one substituent group replace Base；Wherein, the independent selection halogen of the substituent group, amino, cyano, nitro, hydroxyl or sulfydryl；
The heteroaryl is preferably the heteroaryl that unsubstituted heteroaryl or at least one substituent group replace；Wherein, heteroaryl In hetero atom be nitrogen, sulphur or oxygen；The independent selection halogen of the substituent group, amino, cyano, nitro, hydroxyl or sulfydryl；
And described-R indicates any position of ring where it；
Wherein * is link position, indicates any position of ring where it.
In the above-mentioned technical solutions, further preferably the organic electroluminescent compounds are any one in following structures It is a:
Organic electroluminescent compounds of the invention can be prepared by synthetic method known to those skilled in the art. For example, preferably it can be prepared according to following reaction process.
A kind of preparation method of organic electroluminescent compounds, comprising the following steps:
The synthesis of step 1, intermediate C:
Compound B is dissolved in THF, is cooled to -78 DEG C, under nitrogen atmosphere protection, instills n-butyllithium solution, instead It answers, compound A is then added, is warming up to room temperature, the reaction was continued；After reaction, saturated aqueous ammonium chloride is added dropwise, stirs, Ethyl acetate layering, extraction is added, gained organic phase is dry with anhydrous magnesium sulfate, and silica gel column chromatography separating purification obtains centre Body C；
The synthesis of compound shown in step 2, chemical formula 1:
Intermediate C and compound D are dissolved in THF, methanesulfonic acid and polyphosphoric acids, stirring at normal temperature reaction is added；Reaction knot Shu Hou adds water, and ethyl acetate layering, extraction is added in agitator treating, and gained organic phase is washed with saturated sodium bicarbonate aqueous solution, And it is dry with anhydrous magnesium sulfate, silica gel column chromatography separating purification obtains compound shown in chemical formula 1；
Its synthetic route is as follows:
Wherein, R0、R1、R2、Ar1、Ar2, X, Y, ring G, ring Q and a, b, n and t as defined in above-mentioned chemical formula 1, and Z Indicate halogen.
In the above-mentioned technical solutions, the reaction time is 3h after n-butyllithium solution is instilled in preferred steps 1, and compound is added The reaction time is 16h after A.
In the above-mentioned technical solutions, the time reacted in preferred steps 2 is 18h.
A kind of compound of 1 structure of chemical formula of the present invention is used to prepare the application of organic electroluminescence device.
The organic electroluminescence device includes:
First electrode, second electrode and the organic matter layer being placed between two electrode, wherein wrapped in the organic matter layer Compound containing structure shown in chemical formula 1；The compound of structure shown in chemical formula 1 can be single form or and other materials (conventional material of electroluminescent organic material) is mixed in organic matter layer.One in first and second electrode is Anode, and the other is cathode.The organic matter layer includes luminescent layer, and further includes at least one and inject selected from hole The layer of the group of layer, hole transmission layer, electron transfer layer, electron injecting layer, hole blocking layer and electronic barrier layer composition.
Wherein, the organic matter layer includes at least hole injection layer, hole transmission layer, had both had hole injection but also with sky It transmits technical ability layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer and both has electronics biography in cave It is defeated but also with one or more of electron injection technical ability layer.
" organic matter layer " refers to disposing between organic electroluminescence device first electrode and second electrode in the present invention The term of whole layers.
When the compound of 1 structure of chemical formula is present in hole transmission layer or hole injection layer in the organic matter layer When, the compound of 1 structure of formula chemical formula can be used as hole transmission layer, hole injection layer and not only have hole injection but also Has hole transport functional layer.
Of the present invention includes that the device of the compound preparation of 1 structure of chemical formula can be used for organic luminescent device (OLED), organic photovoltaic cell (OSC), Electronic Paper (e-Paper), Organophotoreceptor (OPC) or Organic Thin Film Transistors (OTFT)。
Device of the present invention can be by the methods of film vapor deposition, electron beam evaporation, physical vapour deposition (PVD) in substrate Upper evaporation metal and conductive oxide and their alloy form anode, can also use spin-coating (spin- Coating) or strip takes the lead to be deposited；It can also be using molding (tape-casting), scraping blade method (doctor-blading), silk The methods of wire mark brush (Screen-Printing), ink jet printing or thermal imaging (Thermal-Imaging) reduce number of plies manufacture.
The beneficial effects of the present invention are:
The present invention is provided to the hole mobile materials for solving the problems, such as traditional technology in Organnic electroluminescent device.It passes The hole mobile material of system is substantially based on triaryl derivative.Although it is with cavity transmission ability and low driving voltage, It is to have to introduce a large amount of substituent group in its structure in order to obtain suitable glass transition temperature to promote its molecular weight. But triplet energies or LUMO energy are but reduced in this way, so as to cause the deterioration of organic electroluminescence device.Ideal hole Transmission material need high glass transition temperature, Hole injection capacity and cavity transmission ability and suitable triplet energies and LUMO energy.Therefore, ideal material is obtained in order to solve the problems, such as conventional hole transmission material, the present invention proposes By the solution for introducing arylamine and the loop coil with rigid structure.Hole injection energy is obtained by introducing arylamine Power/transmittability, high power efficiency, long-life；Appropriate glass transition temperature is obtained by introducing loop coil, to obtain excellent The electroluminescent organic material of matter.
The preparation method of organic electroluminescent compounds provided by the invention is simple, yield is high.
The organic electroluminescence device of compound preparation provided by the present invention has splendid current efficiency and power efficiency And the long-life.
Specific embodiment
Embodiment 1: prepare compound 1
The synthesis of intermediate C-1: it by bromobenzene (B-1) (15.7g, 100mmol) as being stirred in 250mL dry THF, drops Temperature under nitrogen atmosphere protection, instills 44mL n-butyllithium solution to -78 DEG C, the reaction was continued 3h.Compound A-1 is then added (34.4g, 100mmol) is to slowly warm up to room temperature, reacts 16h.After reaction, saturated aqueous ammonium chloride is slowly added dropwise 200mL stirs 0.5h, the layering of 300mL ethyl acetate, extraction is added, gained organic phase is dry with anhydrous magnesium sulfate, silica gel column layer Analysis isolates and purifies, and obtains 31.6g intermediate C-1, yield 75%.
The synthesis of compound 1: intermediate C-1 (31.6g, 75mmol) and intermediate D-1 (31.8,80mmol) are placed in In 300mL dry THF, methanesulfonic acid (36g, 375mmol) and polyphosphoric acids (36g) is added, stirring at normal temperature reacts 18h.Reaction After, add water 500mL, agitator treating 0.5h, the layering of 500mL ethyl acetate, extraction, gained organic phase unsaturated carbonate is added Hydrogen sodium water solution washs 3 times, and dry with anhydrous magnesium sulfate, and silica gel column chromatography separating purification obtains 43.3g compound 1.It (receives Rate 72%, MW:801.04).
Embodiment 2: prepare compound 12
Prepare compound 12 (yield are as follows: 70%, MW:957.97) according to the method for embodiment 1.With the difference of embodiment 1 Place is to replace intermediate B -1 using intermediate B -12, using intermediate D-12 instead of intermediate D-1.
Embodiment 3: prepare compound 19
Prepare compound 19 (yield are as follows: 79%, MW:940.33) according to the method for embodiment 1.With the difference of embodiment 1 Place is to replace intermediate B -1 using intermediate B -19, using intermediate D-19 instead of intermediate D-1.
Embodiment 4: prepare compound 26
Prepare compound 26 (yield are as follows: 80%, MW:917.51) according to the method for embodiment 1.With the difference of embodiment 1 Place is to replace intermediate B -1 using intermediate B -26.
Embodiment 5: prepare compound 36
Prepare compound 36 (yield are as follows: 82%, MW:965.7) according to the method for embodiment 1.It is different from embodiment 1 it It is in replacing intermediate B -1 using intermediate B -36, replaces intermediate D-1 using intermediate D-36.
Embodiment 6: prepare compound 50
Prepare compound 50 (yield are as follows: 73%, MW:941.25) according to the method for embodiment 1.With the difference of embodiment 1 Place is to replace intermediate B -1 using intermediate B -50.
Embodiment 7: prepare compound 55
Prepare compound 55 (yield are as follows: 79%, MW:977.43) according to the method for embodiment 1.With the difference of embodiment 1 Place is to replace intermediate B -1 using intermediate B -55, using intermediate D-55 instead of intermediate D-1.
Embodiment 8: prepare compound 61
Prepare compound 61 (yield are as follows: 82%, MW:973.34) according to the method for embodiment 1.With the difference of embodiment 1 Place is to replace intermediate B -1 using intermediate B -61, using intermediate D-61 instead of intermediate D-1.
Embodiment 9: prepare compound 71
Prepare compound 71 (yield are as follows: 80%, MW:816.25) according to the method for embodiment 1.With the difference of embodiment 1 Place is to replace intermediate B -1 using intermediate B -71, using intermediate D-71 instead of intermediate D-1.
Embodiment 10: prepare compound 83
Prepare compound 83 (yield are as follows: 71%, MW:842.10) according to the method for embodiment 1.With the difference of embodiment 1 Place is to replace intermediate B -1 using intermediate B -83, using intermediate D-61 instead of intermediate D-1.
Embodiment 11: prepare compound 86
Prepare compound 86 (yield are as follows: 83%, MW:921.47) according to the method for embodiment 1.With the difference of embodiment 1 Place is to replace intermediate B -1 using intermediate B -12, using intermediate D-86 instead of intermediate D-1.
Embodiment 12: organic electroluminescence device of the manufacture containing compound 1
It is by coating layer thicknessIto glass substrate be placed in distilled water and clean 2 times, ultrasonic washing 30 minutes, It is cleaned repeatedly with distilled water 2 times, ultrasonic washing 10 minutes, after distilled water cleans, isopropanol, acetone, methanol equal solvent It is dry after ultrasonic washing in order, it is transferred in plasma washing machine, aforesaid substrate is washed 5 minutes, vapor deposition is sent to In machine.The 4,4' for being 50nm by evaporation thickness on the ito transparent electrode having had been prepared for, 4 "-three [2- naphthylphenyl amino] three Phenyl amine (2-TNATA) is used as hole injection layer.Then by compound 1 on the hole injection layer of formation vacuum evaporation thickness For the hole transmission layer of 30nm.Then the blue material of main part 9 that evaporation thickness is 30nm on above-mentioned hole transmission layer, 10- bis- (2- naphthalene) anthracene (ADN) and bis- (4,6- difluorophenyl pyridinato-N, the C2) pyridinecarboxylics of dopant material close iridium (FIrpic).Main body material The weight ratio of material and dopant material is 95:5.Then on above-mentioned luminescent layer vacuum evaporation with a thickness of 40nm TPBi as hole Barrier layer and electron transfer layer.Vacuum evaporation is on above-mentioned electron transfer layer with a thickness of 0.5nm lithium fluoride (LiF), as electronics Implanted layer.The aluminium that last evaporation thickness is 150nm completes the preparation of organic electroluminescence device with this as cathode.To The performance characteristics of luminescence of the device arrived is tested, and measurement uses KEITHLEY2400 type source measuring unit, and CS-2000 spectroradio is bright Degree meter, to evaluate driving voltage, light emission luminance, luminous efficiency.
Embodiment 13: organic electroluminescence device of the manufacture containing compound 12
Compound 1 in embodiment 12 is replaced into compound 12, other methods are identical, make having containing compound 12 Organic electroluminescence devices.
Embodiment 14: organic electroluminescence device of the manufacture containing compound 19
Compound 1 in embodiment 12 is replaced into compound 19, other methods are identical, make having containing compound 19 Organic electroluminescence devices.
Embodiment 15: organic electroluminescence device of the manufacture containing compound 26
Compound 1 in embodiment 12 is replaced into compound 26, other methods are identical, make having containing compound 26 Organic electroluminescence devices.
Embodiment 16: organic electroluminescence device of the manufacture containing compound 36
Compound 1 in embodiment 12 is replaced into compound 36, other methods are identical, make having containing compound 36 Organic electroluminescence devices.
Embodiment 17: organic electroluminescence device of the manufacture containing compound 50
Compound 1 in embodiment 12 is replaced into compound 50, other methods are identical, make having containing compound 50 Organic electroluminescence devices.
Embodiment 18: organic electroluminescence device of the manufacture containing compound 55
Compound 1 in embodiment 12 is replaced into compound 55, other methods are identical, make having containing compound 55 Organic electroluminescence devices.
Embodiment 19: organic electroluminescence device of the manufacture containing compound 61
Compound 1 in embodiment 12 is replaced into compound 61, other methods are identical, make having containing compound 61 Organic electroluminescence devices.
Embodiment 20: organic electroluminescence device of the manufacture containing compound 71
Compound 1 in embodiment 12 is replaced into compound 71, other methods are identical, make having containing compound 71 Organic electroluminescence devices.
Embodiment 21: organic electroluminescence device of the manufacture containing compound 83
Compound 1 in embodiment 12 is replaced into compound 83, other methods are identical, make having containing compound 83 Organic electroluminescence devices.
Embodiment 22: organic electroluminescence device of the manufacture containing compound 86
Compound 1 in embodiment 12 is replaced into compound 86, other methods are identical, make having containing compound 86 Organic electroluminescence devices.
Embodiment 23: according to the method for embodiment 12, the material of hole transmission layer is replaced into bis- (1- of N'- by compound 1 Naphthalene)-N, N'- diphenyl-(1,1'- biphenyl) -4,4'- diamines (NPD).
With the thermal decomposition temperature for the compound that thermogravimetry measurement embodiment 1~11 synthesizes.Using differential scanning calorimetry The glass transition temperature Tg of method measurement above compound.The results are shown in Table 1:
Table 1
Embodiment Compound Thermal decomposition temperature Tg(℃)
Embodiment 1 1 455 129
Embodiment 2 12 450 124
Embodiment 3 19 445 130
Embodiment 4 26 490 135
Embodiment 5 36 475 130
Embodiment 6 50 486 131
Embodiment 7 55 487 128
Embodiment 8 61 450 125
Embodiment 9 71 443 130
Embodiment 10 83 484 135
Embodiment 11 86 470 130
Table 2 is the characteristics of luminescence test result of the compound of preparation of the embodiment of the present invention and the luminescent device of NPD preparation.
Table 2
Compound provided by the invention can be regarded as from upper table suitable glass transition temperature, by the compound of the present invention The luminous efficiency of device as hole transmission layer preparation and service life have relative to the device prepared by NPD as hole transmission layer It is significant to improve.
The above description of the embodiment is only used to help understand the method for the present invention and its core ideas.It should be pointed out that pair For those skilled in the art, without departing from the principle of the present invention, the present invention can also be carried out Some improvements and modifications, these improvements and modifications also fall within the scope of protection of the claims of the present invention.

Claims (10)

1. a kind of organic electroluminescent compounds, which is characterized in that its structural formula as described in chemical formula 1:
Wherein:
Ar1And Ar2Each independently represent the C1-C30 alkyl for being substituted or being unsubstituted, the C6- for being substituted or being unsubstituted C30 aryl or 3 to 30 unit's heteroaryls for being substituted or being unsubstituted；Or it is connect with adjacent substituents and to form monocycle or polycyclic C3- C30 aliphatic ring or aromatic ring, the replaceable hetero atom that nitrogen, oxygen or sulphur are selected from least one of carbon atom；
R0For hydrogen or deuterium；T indicates 0 to 4 integer；
R1And R2Hydrogen is each independently represented, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, amido, is substituted or is unsubstituted C1-C30 alkyl, the C2-C30 alkenyl for being substituted or being unsubstituted, the C2-C30 alkynyl for being substituted or being unsubstituted, be substituted or The C1-C30 alkoxy that is unsubstituted, the C3-C30 naphthenic base for being substituted or being unsubstituted, the C3- for being substituted or being unsubstituted C30 cycloalkenyl, 3 to 7 membered heterocycloalkyls for being substituted or being unsubstituted, the C6-C30 aryl for being substituted or being unsubstituted or through taking Generation or 3 to 30 unit's heteroaryls being unsubstituted；Or it is connect with adjacent substituents and to form the monocycle for being substituted or being unsubstituted or more Ring C3-C30 aliphatic ring or aromatic ring, the replaceable hetero atom that nitrogen, oxygen or sulphur are selected from least one of carbon atom；
X is-O- ,-S- ,-C (R5)(R6)-、-N(R7)-or-Si (R8)(R9)-, Y is-[C (R3)c(R4)d]m-；
R3To R9Each independently represent the C1-C30 alkyl for being substituted or being unsubstituted, the C2-C30 for being substituted or being unsubstituted Alkenyl, the C2-C30 alkynyl for being substituted or being unsubstituted, the C1-C30 alkoxy for being substituted or being unsubstituted, be substituted or without Substituted C3-C30 naphthenic base, the C3-C30 cycloalkenyl for being substituted or being unsubstituted, be substituted or be unsubstituted 3 to 7 yuan it is miscellaneous Naphthenic base, the C6-C30 aryl for being substituted or being unsubstituted or 3 to 30 unit's heteroaryls for being substituted or being unsubstituted；Or with it is adjacent Substituent group, which connects, to form the monocycle for being substituted or being unsubstituted or polycyclic C3-C30 aliphatic ring or aromatic ring, carbon atom can It is replaced as at least one hetero atom for being selected from nitrogen, oxygen or sulphur；
Q ring indicates the C6-C30 aryl for being substituted or being unsubstituted or 3 to 30 unit's heteroaryls for being substituted or being unsubstituted；
G ring indicates the C3-C30 naphthenic base for being substituted or being unsubstituted, the C3-C30 cycloalkenyl for being substituted or being unsubstituted, through taking Generation or 3 to 7 membered heterocycloalkyls that are unsubstituted, the C6-C30 aryl for being substituted or being unsubstituted are substituted or are unsubstituted 3 to 30 unit's heteroaryls；
A, b each independently represents 0 to 4 integer, and c, d each independently represent 0 to 2 integer, m and n table each independently When showing that 0 or 1 and n is 1, m is 0 or 1；When n is 0, R1It can be substituted or with the G ring being connected formation has been shown in general formula without taking The polycyclic C3-C30 aliphatic ring or aromatic ring in generation, carbon atom it is replaceable one in nitrogen, oxygen, sulphur and silicon or More than.
2. organic electroluminescent compounds according to claim 1, which is characterized in that Ar1And Ar2It each independently represents Any one in following structures:
Wherein, R is the virtue of hydrogen, halogen, cyano, the alkyl of C1-C30, the aryl of C6-C50, the aralkyl of C7-C50, C7-C50 Base alkoxy, the aryl alkane sulfydryl of C7-C50 or the heteroaryl of C5-C50.
3. organic electroluminescent compounds according to claim 1, which is characterized in that
Part be following structures in any one:
Wherein, R is the virtue of hydrogen, halogen, cyano, the alkyl of C1-C30, the aryl of C6-C50, the aralkyl of C7-C50, C7-C50 Base alkoxy, the aryl alkane sulfydryl of C7-C50 or the heteroaryl of C5-C50.
4. organic electroluminescent compounds according to claim 1, which is characterized in that it is any one in following structures It is a:
5. a kind of preparation method of organic electroluminescent compounds described in claim 1-4 any one, which is characterized in that including with Lower step:
The synthesis of step 1, intermediate C:
Compound B is dissolved in THF, under nitrogen atmosphere protection, instills n-butyllithium solution, compound is then added in reaction A is warming up to room temperature, and the reaction was continued；After reaction, saturated aqueous ammonium chloride is added dropwise, stirs, the layering of addition ethyl acetate, Extraction, gained organic phase is dry with anhydrous magnesium sulfate, and silica gel column chromatography separating purification obtains intermediate C；
The synthesis of compound shown in step 2, chemical formula 1:
Intermediate C and compound D are dissolved in THF, methanesulfonic acid and polyphosphoric acids, stirring at normal temperature reaction is added；After reaction, Add water, ethyl acetate layering, extraction is added in agitator treating, and gained organic phase is washed with saturated sodium bicarbonate aqueous solution, and uses nothing Water magnesium sulfate is dry, and silica gel column chromatography separating purification obtains compound shown in chemical formula 1；
Its synthetic route is as follows:
Wherein, Z indicates halogen.
6. the preparation method of organic electroluminescent compounds according to claim 5, which is characterized in that instill positive fourth in step 1 The reaction time is 3h after base lithium solution, and the reaction time is 16h after compound A is added.
7. the preparation method of organic electroluminescent compounds according to claim 5, which is characterized in that reacted in step 2 when Between be 18h.
8. organic electroluminescent compounds described in a kind of claim 1-4 any one are used to prepare organic electroluminescence device Application.
9. application according to claim 8, which is characterized in that organic electroluminescence device includes:
First electrode, second electrode and the organic matter layer being placed between two electrode, wherein include in the organic matter layer Organic electroluminescent compounds described in claim 1-4 any one；Organic electroluminescence described in claim 1-4 any one Luminophor can be single form or be mixed in organic matter layer with other materials.
10. application according to claim 9, which is characterized in that the organic matter layer includes at least hole injection layer, hole Transport layer had both had hole injection but also with hole transport technical ability layer, electronic barrier layer, luminescent layer, hole blocking layer, electronics biography Defeated layer, electron injecting layer and both has electron-transport but also with one or more of electron injection technical ability layer.
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