CN109081830A - Diphenylpyrimidin compound and its organic electroluminescence device through benzimidazole substitution - Google Patents

Diphenylpyrimidin compound and its organic electroluminescence device through benzimidazole substitution Download PDF

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CN109081830A
CN109081830A CN201810770572.6A CN201810770572A CN109081830A CN 109081830 A CN109081830 A CN 109081830A CN 201810770572 A CN201810770572 A CN 201810770572A CN 109081830 A CN109081830 A CN 109081830A
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compound
unsubstituted
diphenylpyrimidin
layer
aryl
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黄贺隆
赵登志
郭晃铭
林祺臻
张敏忠
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Changzhou Qiangyu Radium Photoelectric Material Co Ltd
E Ray Optoelectronics Technology Co Ltd
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Changzhou Qiangyu Radium Photoelectric Material Co Ltd
E Ray Optoelectronics Technology Co Ltd
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Abstract

The present invention provides a kind of diphenylpyrimidin compounds through benzimidazole substitution, are indicated with following formula (I), wherein X1, Ar and n such as the definition in specification, and the organic electroluminescence device prepared using the compound.

Description

Diphenylpyrimidin compound and its organic electroluminescence device through benzimidazole substitution
Technical field
The present invention is about a kind of diphenylpyrimidin compound through benzimidazole substitution and uses the Organic Electricity of the compound Electroluminescence device.
Background technique
Organic light emission refer to by organic material convert electrical energy into luminous energy in the way of, since organic luminescent device is in display In the purposes of device, have many advantages, such as that self-luminous, service life are long, color saturation, colour gamut is wide, high-efficient, driving voltage is low and at low cost, Therefore it attracts attention, and in order to apply organic electroluminescent device in various occasion and field, all circles' especially inking has in novelty In the developmental research of machine material.
OLED device has at least one layer of organic layer between anode and cathode.Upon application of a voltage, hole and electronics difference It can be injected into one or more layers organic layer from anode, cathode, respectively migrated by injected holes and electronics to opposite electrification Charged electrode.When electronics and hole are limited on the same molecule, understands in conjunction with and form " exciton (exciton) ", the exciton For localization's electron-hole pair in excitation state, (theoretically, the 25% of the excitation state is singlet excited, and another 75% is Triplet excited state), and can be discharged energy in the form of light or heat when the exciton returns to ground state from excitation state.For lifter The charge transport ability and luminous efficiency of part, in addition to use electronics appropriate, hole transport/injection material or improve the transmission/ Outside injection material, it can also reach by the structure for improving organic electroluminescence device, such as by electron transfer layer and/or hole Transport layer or electronic barrier layer and/or hole blocking layer are laminated on luminescent layer, it is considered that such multilayered structure be earliest by Kodak's invention, the multilayered structure that Kodak is invented lie on substrate sequentially lamination anode, hole transmission layer, Shine simultaneous electron transfer layer and cathode.In addition, by guest materials is adulterated in material of main part, also can be improved luminous efficiency with And adjustment coloration.Be incorporated by herein with reference to the U.S. the 4769292nd, 5844363,5707745,6596415 and 6465115 Several OLED materials and device group structure are described in patent.Sunlight radium Optoelectronics Technology applied in 2016 and obtained card in 2017 The electron transport material of TaiWan, China patent No. I582081, this patent have certain novelty and effect.
Since the mobility (mobility) of hole and electronics in organic material is different, in order to avoid hole And in conjunction with region close to electrode quenching phenomenon occurs for electronics, therefore develops the OLED device of multi-layer film structure.It has been observed that Since the mobility in electronics and hole is different in organic material, if therefore using hole transport appropriate and electron-transport Layer then can make the electronics and the density balance in hole in the luminescent layer, increase effectively by hole and electron-transport to luminescent layer Electronics and hole in conjunction with rate, and then increase luminous efficiency.In addition, the device can be promoted by above-mentioned organic layer is appropriately combined Part efficiency and service life.However, being still difficult to find that the organic material for meeting the demand that all actual displays are applied so far, especially Thermal stability is good, the service life length organic material that can be applied to illumination.
Therefore, organic electro-luminescence device lifetime and the good organic material of heat resistance can be significantly improved by needing one kind, with Meet the demand of diversification application.
Summary of the invention
Purpose of the present invention is to provide a kind of service life is long and the good organic material of heat resistance.
The present invention provides a kind of diphenylpyrimidin compound through benzimidazole substitution, is indicated with following formula (I),
Wherein, X1Expression is substituted or is unsubstituted its (C6-C30) aryl, is substituted or is unsubstituted its (5- to 30- Member) heteroaryl；
Ar expression is substituted or is unsubstituted its (C6-C30) aryl, is substituted or is unsubstituted its (5- to 30- member) Heteroaryl；
X1And Ar is identical or different, and at least one is to be substituted or be unsubstituted its (5- to 30- member) heteroaryl；
N indicates 1 or 2 integer, and when n indicates 2, Ar is respectively identical or different.
Also, the present invention provides a kind of organic electroluminescence device, include:
Cathode；
Anode；And
Organic layer: between the cathode and anode, contain two through benzimidazole substitution of the invention indicated with formula (I) Phenylpyrimidine compound.
By the diphenylpyrimidin compound through benzimidazole substitution of the invention indicated with formula (I), it is possible to provide a kind of Service life is long, the good organic material of heat resistance, can satisfy the demand of vehicle display and lighting use related fields, especially suitable Cooperation is lighting source.
Detailed description of the invention
The accompanying drawings constituting a part of this application is used to provide further understanding of the present invention, and of the invention shows Examples and descriptions thereof are used to explain the present invention for meaning property, does not constitute improper limitations of the present invention.In the accompanying drawings:
The diagrammatic cross-section of one of the organic electroluminescence device of Fig. 1 system present invention embodiment.
The diagrammatic cross-section of another embodiment of the organic electroluminescence device of Fig. 2 system present invention.
The diagrammatic cross-section of the another embodiment of the organic electroluminescence device of Fig. 3 system present invention.
[symbol description]
100,200,300 organic electroluminescence device
110,210,310 substrate
120,220,320 anode
130,230,330 hole injection layer
140,240,340 hole transmission layer
150,250,350 luminescent layer
160,260,360 electron transfer layer
170,270,370 electron injecting layer
180,280,380 cathode
245,355 exciton barrier-layer
Specific embodiment
It should be noted that in the absence of conflict, the features in the embodiments and the embodiments of the present application can phase Mutually combination.The present invention will be described in detail below with reference to the accompanying drawings and embodiments.
The embodiment for illustrating the present invention by particular specific embodiment below, the personage for being familiar with this skill can be by this theory The disclosed content of bright book understands the advantage and effect of the present invention easily.The present invention also can be by the embodiment of other differences It is implemented or is applied, details in this specification can also be based on different perspectives and applications, is taken off not departing from the present invention It is modified under the spirit shown and change.In addition, all ranges and numerical value are all to include and annexable herein.It falls in herein Any numerical value or point in the range, such as any integer all can serve as minimum value or maximum value to export the next range Deng.
The diphenylpyrimidin compound through benzimidazole substitution of the present invention is to be indicated with following formula (I),
Wherein, X1Expression is substituted or is unsubstituted its (C6-C30) aryl, is substituted or is unsubstituted its (5- to 30- Member) heteroaryl；
Ar expression is substituted or is unsubstituted its (C6-C30) aryl, is substituted or is unsubstituted its (5- to 30- member) miscellaneous Aryl；
X1And Ar is identical or different, and at least one is to be substituted or be unsubstituted its (5- to 30- member) heteroaryl；
N indicates 1 or 2 integer, and when n indicates 2, Ar is respectively identical or different.
In a specific embodiment, the above-mentioned diphenylpyrimidin compound through benzimidazole substitution indicated with formula (I) is With following formula (I-1), formula (I-2) or formula (I-3) representation:
Wherein, X1Expression is substituted or is unsubstituted its (C6-C30) aryl, is substituted or is unsubstituted its (5- to 30- Member) heteroaryl；
Ar expression is substituted or is unsubstituted its (C6-C30) aryl, is substituted or is unsubstituted its (5- to 30- member) miscellaneous Aryl；
X1And Ar is identical or different, and at least one is to be substituted or be unsubstituted its (5- to 30- member) heteroaryl；
N indicates 1 or 2 integer, and when n indicates 2, Ar is respectively identical or different.
The Ar for the diphenylpyrimidin compound through benzimidazole substitution that the present invention is indicated with formula (I) be substituted or without Replace its (C6-C30) aryl, be substituted or be unsubstituted its (5- to 30- member) heteroaryl, reason is: planar structure is got over It is more, more facilitate molecule storehouse, and increase the laser propagation effect of its carrier, only, group carbon number should not be excessive, to avoid being formed not Necessary crystallization.
The X for the diphenylpyrimidin compound through benzimidazole substitution that the present invention is indicated with formula (I)1For be substituted or without Replace its (C6-C30) aryl, be substituted or be unsubstituted its (5- to 30- member) heteroaryl, there is the work for inhibiting molecular crystalline With.In a specific embodiment, X1For pyridyl group, quinolyl or naphthalene.
In another specific embodiment, the diphenylpyrimidin chemical combination through benzimidazole substitution that the present invention is indicated with formula (I) X in object1System is selected from one of following formed group person:
Wherein, Xr indicates hydrogen, fluorine, cyano, C1-4 alkyl or the C6-18 aryl being unsubstituted.
In a specific embodiment, the diphenylpyrimidin compound through benzimidazole substitution that the present invention is indicated with formula (I) In Ar system be selected from one of following formed group person:
Wherein, L indicates O or S；
Ar1To Ar6Each independent C6-18 aryl for indicating hydrogen, being unsubstituted；
R1To R4Each independent C6-12 aryl, R for indicating hydrogen, being substituted or being unsubstituted1And R2With the carbon atom being connected C6-18 condensed aromatic loop system or R is collectively formed3And R4C6-18 condensed aromatic ring system is collectively formed with the carbon atom being connected System；And
Y1And Y2One of them be singly-bound and to be connected to formula (I) compound, another one is hydrogen.
In a specific embodiment, when n is 1, which is shown in formula (I-4) or formula (I-5).
In a specific embodiment, when n is 2, which is shown in formula (I-6).
In another specific embodiment, when formula (I) compound is shown in formula (I-6), Ar is identical structure.
In this manual, " being substituted it " in so-called " being substituted or be unsubstituted it ", means in some functional group In hydrogen atom replaced through another atom or group (i.e. substituent group).The grade substituent groups are each independently selected from by following group At at least one of group: deuterium, halogen, C1-30 alkyl, C1-30 alkoxy, C6-30 aryl, C5-30 heteroaryl, warp The C5-30 heteroaryl of C6-30 aryl substitution, benzimidazolyl, C3-30 naphthenic base, C5-7 Heterocyclylalkyl, three C1-30 alkyl silicons Alkyl, three C1-30 aryl-silane bases, two C1-30 alkyl C6-30 aryl-silane bases, two C6-30 aryl-silane base of C1-30 alkyl, C2-30 alkenyl, C2-30 alkynyl, cyano, two C1-30 alkyl amine groups, two C6-30 aryl boryls, two C1-30 alkyl boryls, C1- 30 alkyl, C6-30 aryl C1-30 alkyl, C1-30 alkyl C6-30 aryl, carboxyl, nitro and hydroxyl.
In this manual, " aryl " indicates that aryl or (stretching) aryl, the aryl mean the monocycle system derived from aromatic hydrocarbon Ring or fused rings, such as can enumerate: phenyl, xenyl, terphenyl base, naphthalene, binaphthyl, phenyl napthyl, naphthylphenyl, Fluorene Base, phenyl Fluorene base, benzo Fluorene base, dibenzo Fluorene base, phenanthryl, phenyl phenanthryl, benzo phenanthryl, anthryl, benzo anthryl, indenyl, connection Stretch triphenyl, pyrenyl,Base, thick four benzene base, base, Kuai Ji, naphtho- naphthalene, propylene close Fluorene base, allene closes Fluorene base, benzo Propylene closes Fluorene base etc..
In this manual, " heteroaryl " indicates that heteroaryl or (stretching) heteroaryl, the heteroaryl can be monocycle system ring, such as Can enumerate: furyl, thienyl, pyrrole radicals, imidazole radicals, pyrazolyl, thiazolyl, thiadiazolyl group, isothiazolyl, isoxazolyl, Oxazolyl, oxadiazoles base, threeBase, fourBase, triazolyl, tetrazole radical, furan Xanthones base, pyridyl group, pyrroleBase, pyrimidine radicals, clatterBase, piperidyl etc., or the fused rings to be condensed at least one phenyl ring, such as can enumerate: benzofuranyl, benzothiophene Base, isobenzofuran-base, dibenzofuran group, dibenzothiophene, benzimidazolyl, benzothiazolyl, benzisothia oxazolyl, Benzo isoxazolyl, benzo two dislike oh base, benzopyrene oxazolyl, such as can be quinolyl, isoquinolyl, cinnoline base, quinoline azoles Quinoline base, quinoxaline base, carbazyl, coffee oxazolyl, coffee piperidinyl, acridan base, imidazole pyridyl,Piperidinyl, daiBase, a word used for translation Piperidinyl, coffee quinoline base, indyl, coffeeBase etc..
In specific embodiment, the diphenylpyrimidin compound through benzimidazole substitution that the present invention is indicated with formula (I) Preferred aspect, as described in Table 1, but not limited to this.
Table 1
The present invention indicates the diphenylpyrimidin compound replaced through benzimidazole with formula (I), due to its glass transition temperature (Tg) between 125 DEG C to 180 DEG C, and its thermal cracking temperature (Td) between 486 DEG C to 566 DEG C, therefore vapour can be born The high temperature of interior minister's phase, therefore the organic electroluminescence device especially suitable for vehicle display.
The present invention provides a kind of organic electroluminescence device again, includes:
Cathode；
Anode；And
Organic layer: between the cathode and anode, contain two through benzimidazole substitution of the invention indicated with formula (I) Phenylpyrimidine compound.
The organic layer of the organic electroluminescence device of the present invention can be electron transfer layer, electron injecting layer, luminescent layer, sky Cave barrier layer or electronic barrier layer, and other than the organic layer, which can also be organic containing this is different from Layer in the group being made of electron transfer layer, electron injecting layer, luminescent layer, hole blocking layer and electronic barrier layer at least One layer, wherein the luminescent layer contains fluorescence or phosphorescent guest dopant and respectively corresponds the fluorescence or phosphorescent guest dopant Material of main part.
In a specific embodiment, the diphenylpyrimidin chemical combination through benzimidazole substitution is indicated with formula (I) containing the present invention The organic layer of object is preferably electron transfer layer, and its thickness is preferably 20 nanometers to 30 nanometers；Wherein, which can incite somebody to action The diphenylpyrimidin compound through benzimidazole substitution of tool formula (I) structure as homogenous material, or will tool formula (I) structure it Diphenylpyrimidin compound through benzimidazole substitution is used in combination with electrical conductivity dopant.
In another specific embodiment, which contains N-type electrical conductivity dopant again, wherein the N-type is electrical The diphenylpyrimidin compound through benzimidazole substitution of conductivity dopant and tool formula (I) structure of the present invention can generate chelation (chelation), electronics can be made more easily to be injected into electron transfer layer from cathode, thus can solve prior art because metal with The problem of mutually separating and be quenched caused by the poor compatibility of electron transport material can effectively improve the biography of electron transfer layer Defeated efficiency.
N-type electrical conductivity dopant applied to electron transfer layer can be organic alkali metal/alkaline-earth metal nitrate, carbon Hydrochlorate, phosphate or quinolinic acid, such as can enumerate: lithium carbonate, quinoline lithium (lithium quinolate, Liq), Azide Lithium (lithium azide), silver nitrate, barium nitrate, magnesium nitrate, zinc nitrate, cesium nitrate, cesium carbonate, cesium fluoride, is folded rubidium carbonate Nitrogenize caesium etc., wherein the N-type electrical conductivity dopant is preferred especially with quinolinic acid lithium.
It in a specific embodiment, is calculated with the weight of the electron transfer layer, the content of the N-type electrical conductivity dopant is 5 weight % to 50 weight %.
Schema used below, come illustrate the present invention organic electroluminescence device structure.
The diagrammatic cross-section of one specific embodiment of organic electroluminescence device of Fig. 1 system present invention.Organic electroluminescence Part 100 includes substrate 110, anode 120, hole injection layer 130, hole transmission layer 140, luminescent layer 150, electron transfer layer 160, electron injecting layer 170 and cathode 180.Organic electroluminescence device 100 can be made by deposited in sequential above layers.
The diagrammatic cross-section of the organic electroluminescence device another specific embodiment of Fig. 2 system present invention.Organic electroluminescent Device 200 includes substrate 210, anode 220, hole injection layer 230, hole transmission layer 240, exciton barrier-layer 245, luminescent layer 250, electron transfer layer 260, electron injecting layer 270 and cathode 280 are hole transmission layer 240 and luminescent layer with the difference of Fig. 1 The exciton barrier-layer 245 is provided between 250.
The diagrammatic cross-section of the yet another embodiment of the organic electroluminescence device of Fig. 3 system present invention.Organic electroluminescence Luminescent device 300 includes substrate 310, anode 320, hole injection layer 330, hole transmission layer 340, luminescent layer 350, exciton blocking Layer 355, electron transfer layer 360, electron injecting layer 370 and cathode 380 are that luminescent layer 350 and electronics pass with the difference of Fig. 1 The exciton barrier-layer 355 is provided between defeated layer 360.
Organic electroluminescence can be manufactured according to the inverted structure (reverse structure) of device shown in Fig. 1 to Fig. 3 Part.Also, visual demand increases and decreases one or more layers for the inverted structure.
The hole injection layer, hole transmission layer, exciton barrier-layer, electronic barrier layer, electron injecting layer material can Material is commonly used in selection, for example, the electron transport material for forming electron transfer layer is different from the material of luminescent layer, and it has Hole transport ability, and hole can be made to migrate in electron transfer layer, and the dissociation energy because of luminescent layer and electron transfer layer can be prevented Carrier accumulation caused by difference.
The diphenylpyrimidin compound through benzimidazole substitution that the present invention is indicated with formula (I) is higher than 2.2eV due to having The triplet energy rank of (client is planned to invite to confirm), the HOMO energy rank for being deeper than 6.0eV and good carrier transport factor, therefore work as and be used in When the situation of electron transfer layer, it can aid in and promote exciton and emit light in relaxing in luminescent layer.
In addition, through look into U.S.'s 20170005275A1 patent disclose p-type doping hole transmission layer in HT3 doped with HT-D2, and the patent is also material doped in electron transport material as n-type doping by Lithium quinolate (Liq) (ET3) in, by the equal content quotations in the present invention.Also, for example by the 5703436th and No. 5707745 patent in the U.S. disclose about The full content of cathode is incorporated in the present invention, and the composition of the cathode is, for example, magnesium/silver (Mg:Ag), and deposits to be formed with sputter Bright conductive layer (ITO Layer).In addition, each disclosed in the present invention reference patent of the U.S. the 6097147th and 20030230980 The application on barrier layer and the full content of principle.In addition, the present invention also quote the patent of the U.S. the 20040174116th it is illustrated it The related content of implanted layer and protective layer.
The present invention can also apply other structure and material, and polymerization is contained as disclosed in the patent of the U.S. the 5247190th The organic electroluminescence device of object material (PLEDs).Furthermore only with the organic electroluminescence device or such as of single organic layer The plural layer organic electroluminescence device of No. 5707745 patent announcement in the U.S., the present invention are also applicable in it.
Unless otherwise stated, any proper method can be used to be formed for any layer in each embodiment.For organic layer, compared with Good forming method vapour deposition method and spray printing method as disclosed in the patent of the U.S. the 6013982nd and 6087196, the U.S. the 6337102nd The disclosed organic vapor phase deposition method (organic vapor phase deposition, OVPD) of number patent, the U.S. the 10/th Disclosed organic vapors spray printing sedimentation (the deposition by organic vapor jet of No. 233470 patents Printing, OVJP), the present invention quotes the related content of these patent application cases.Other proper methods further include rotary coating Method and the processing procedure based on solution.Processing procedure based on solution is preferably in the environment for being not susceptible to oxidation, such as nitrogen Or it is carried out in inert gas environment.For other layers, preferred approach can for example lift vapour deposition method.Preferable patterning method packet The processing procedure of the shielding of the utilization as disclosed in the patent of the U.S. the 6294398th and 6468819 is included, and integrates spray printing or organic vapors Spray printing deposition and patterned processing procedure, the present invention quote the related content.Certainly other methods also can be used.
The diphenylpyrimidin compound through benzimidazole substitution that the present invention is indicated with formula (I), can be with vacuum deposition, wet type The amorphism film applied to organic electroluminescence device is made in rubbing method (including spin-coating method, ink-jet method) or print process.
The organic electroluminescence device of the present invention can be applied to active or passive type structure.Compared to conventional device, originally The organic electroluminescence device of invention can be obviously improved thermal stability and service life.In addition, can by doping phosphorescent guest dopant, The organic electroluminescence device of the present invention is set to emit white light, cooperation optical filter realizes full-color or colorful display panel.
Below by synthesis example and embodiment many properties and effect that the present invention will be described in detail.Only, these synthesis examples and Embodiment is only the embodiments such as the present invention is not limited thereto to illustrate and understand the present invention.
[synthesis example 1]
By 4- (1- phenyl -1H- benzo [d] imidazoles -2- base) phenylboric acid (150g, 753.61mmol) and 1- (4- bromo - Phenyl)-ethyl ketone (1- (4-Bromo-phenyl)-ethanone) (260.42g, 828.97mmol) and potassium carbonate (260.37g, 1884mmol) is placed in reaction flask, adds toluene 2250ml, EtOH 366ml, DI H2N on O 732ml and frame2 It is moved in oil cauldron with condenser pipe and by reacting, heating makes temperature rise to 80 DEG C, takes Pd (PPh3)4(43.52g, 37.68mmol) It is incorporated in reaction and temperature is risen into 80 DEG C of back flow reactions 16 hours, cooling after having reacted is concentrated into glutinous after removing water layer After thick, toluene heating is added and passes through tubing string (100g Al2O3/200g SiO2), concentrate the filtrate to it is sticky after pour into beaker standing After filtering is precipitated, gray solid is obtained, 260g compound as white solid A, yield: 88.5% are obtained after drying.
By compound A (163.15g, 419.99mmol), 3- bromo-benzaldehyde (74g, 399.99mmol), ETOH:3263 Stirring in reaction flask is added in ml, sodium tert-butoxide (Sodium-t-butoxide) (58.2g, 600mmol) is eventually adding, in room temperature Stirring, wait react completely after be added deionized water 2000ml agitation and filtration, cross filter solid with deionized water with methanol cleaning, Gu Body is stirred 30 minutes with 1000ml deionized water and 2000ml methanol filter again, be repeated 2 times dry the solid to obtain 220g it is yellowish Color solid chemical compound B, yield 94.5%.
By compound B (124g, 223.23mmol), 3- picolyl ether hydrochloride (52.77g, 334.83mmol) and phosphoric acid Potassium (165.84 g, 781.31mmol), dimethylbenzene 1240ml are put to heating stirring in reaction flask and maintain 140 DEG C of reflux.It has reacted It is cooled to 90 DEG C after complete, deionized water 500ml is added and stirs 5min, after removing water layer, has solid after organic layer is concentrated to dryness It is precipitated, then white solid to rinse solid and is obtained by filtration with ethyl acetate, 64g compound as white solid C is obtained after drying, is produced Rate: 43.66%.
By 4- dibenzofurans boric acid (5.8g, 27.35mmol), compound C (15g, 22.84mmol) and potassium carbonate (7.9g, 57.1mmol) is placed in reaction flask, N on addition toluene 225ml, ethyl alcohol 38ml, deionized water 76ml and frame2With it is cold It is solidifying to manage and move to reaction in oil cauldron, 80 DEG C of heating stirring.Tetrakis triphenylphosphine palladium (1.32g, 1.14mmol) is added and is reacted Bottle, after complete reaction and there are many solids to be precipitated, and filters in advance after removing oil bath cooling, filter cake is poured into beaker, and add It filters, filter cake is dug into beaker, and tetrahydrofuran 3000ml heating stirring is added after entering deionized water 100ml stirring 10mins To complete molten, pass through tubing string (20g SiO2), concentrate the filtrate to it is dry have white solid precipitation after, filtered with ethyl acetate rinse, Drying obtains 13g compound as white solid 1-2, yield 76.3%.
It shows below1The measurement result of H NMR.
1H NMR(CDCl3,400MHz)δ9.96(s,1H),8.99(d,1H),8.84(s,1H),8.76(d,1H),8.38 (d,2H), 8.34(d,1H),8.19(s,1H),8.13(d,1H),8.03(d,2H),7.92(d,1H),7.81-7.71(m, 6H),7.65-7.64(m,3H), 7.57-7.47(m,6H),7.41-7.35(m,4H),7.31-7.27(m,2H).
[synthesis example 2]
Compound A (30g, 77.22mmol), 4- bromo-benzaldehyde (13.6g, 73.55mmol), ethyl alcohol 600ml are added Stirring, is eventually adding sodium tert-butoxide (13.6g, 220.65mmol) and is stirred at room temperature in reaction flask, is added goes after complete reaction Ionized water 500ml agitation and filtration is crossed filter solid and is cleaned with deionized water with methanol, and solid is again with 500ml deionized water, 500ml Methanol filters after stirring 30 minutes, is repeated 2 times and dries solid to obtain 40g faint yellow solid compound D, yield 92.9%.
By compound D (33g, 59.41mmol), 3- picolyl ether (14g, 89.11mmol) and phosphoric acid (44.14g, 207.93 mmol), dimethylbenzene 3300ml put in reaction flask heating stirring maintain 140 DEG C reflux, be cooled to after complete reaction 90 DEG C, after deionized water 500ml stirring 5min is added, after removing water layer, there is solid precipitation second after organic layer is concentrated to dryness Acetoacetic ester obtains 16g compound as white solid E, yield 41.1% to rinse solid with white solid, drying is obtained by filtration.
By 4- dibenzofurans boric acid (5.8g, 27.35mmol), compound E (15g, 22.84mmol) and potassium carbonate (7.9g, 57.1mmol) is placed in reaction flask, adds N on toluene 225ml, ethyl alcohol 38ml, deionized water 76ml and frame2With it is cold It is solidifying to manage and move to reaction in oil cauldron, 80 DEG C of heating stirring, tetrakis triphenylphosphine palladium (1.32g, 1.14mmol) is added and is reacted Bottle, after complete reaction and there are many solids to be precipitated, and filters in advance after removing oil bath cooling, filter cake is poured into beaker, and add It is filtered after entering deionized water 100ml stirring 10mins.Filter cake is dug into beaker and tetrahydrofuran 3000ml heating stirring is added To complete molten, pass through tubing string (20g SiO2), concentrate the filtrate to it is dry have white solid precipitation after, with ethyl acetate come flushed Filter, drying obtain 14g compound as white solid 1-3, yield 82.4%.
It shows below1The measurement result of H NMR.
1H NMR(CDCl3,400MHz)δ9.95(s,1H),8.99(d,1H),8.78(d,1H),8.48(d,2H),8.38 (d,2H), 8.18(t,3H),8.02-8.00(m,2H),7.91(d,1H),7.81(d,2H),7.70-7.67(m,3H), 7.66-7.62(m,3H), 7.58-7.48(m,6H),7.41-7.36(m,4H),7.33-7.28(m,2H).
[synthesis example 3]
Respectively by 1- (4- bromo phenyl) ethyl ketone (19.9g, 100mmole), potassium hydroxide (1.68g, 30mmole) and 4- Bromobenzaldehyde (18.5g, 100mmole) is placed in 1000mL double-necked round bottom bottle, and 300mL ethyl alcohol is added, and it is small to stir 4 at room temperature When.It is filtered, obtains 35.5g Off-white solid compound F, yield 97.0%.
Respectively by compound F (9.15g, 25mmole), 3- picolyl ether hydrochloride (3.94g, 25mmole) and hydroxide Potassium (1.68 g, 30mmole) is placed in 500mL double-necked round bottom bottle, and 150mL ethyl alcohol is added, is heated to flowing back.After reaction 3 hours, It stands back and warms to room temperature, be filtered, solid is cleaned with ethyl alcohol, obtains 8.45g compound as white solid G, yield 72.4%.
Respectively by Pd (PPh3)4(1.65g, 1.45mmole), K2CO3(10.0g, 72.8mmole), compound G (8.5g, 18.2 mmole) and 4- (1- phenyl -1H- benzo [d] imidazoles -2- base) phenylboric acid (12.6g, 40.1mmole) merging 500mL In double-necked round bottom bottle, 80mL toluene, 55mL ethyl alcohol and 25mL deionized water is added, is heated to flowing back.After reacting overnight, it is added 50mL ethyl acetate is extracted, and filtrate after extraction is added and carries out purification by chromatography with filling gel, is concentrated into thick, addition Methanol 30mL reinforces being precipitated, and organic layer merged filter solid, and obtained 8.5g Off-white solid compound 1-5, yield 55.1%.
It shows below1The measurement result of H NMR.
1H NMR(CDCl3,400MHz)δ9.93(s,1H),8.96(dt,1H),8.76(dd,1H),8.37(d,4H), 8.12(s,1H), 7.92(d,2H),7.81(d,2H),7.57-7.71(m,4H),7.65-7.63(m,4H),7.57-7.52 (m, 6H), 7.40~7.35 (m, 6H), 7.31-7.27 (m, 5H)
[synthesis example 4]
Respectively by 1- (4- bromo phenyl) ethyl ketone (19.9g, 100mmole), potassium hydroxide (1.68g, 30mmole) and 3- Bromobenzaldehyde (18.5g, 100mmole) is placed in 1000mL double-necked round bottom bottle, and 300mL ethyl alcohol is added, and it is small to stir 4 at room temperature When.Filtering, obtains 34.4g Off-white solid compound H, yield 93.7%.
Respectively by compound H (9.15g, 25mmole), 3- picolyl ether hydrochloride (3.94g, 25mmole) and hydroxide Potassium (1.68 g, 30mmole) is placed in 500mL double-necked round bottom bottle, and 150mL ethyl alcohol is added, is heated to flowing back.After reaction 3 hours, It stands back and warms to room temperature, filter, solid is cleaned with ethyl alcohol, obtains 9.34 grams of compound as white solid I, yield 80%.
Respectively by Pd (PPh3)4(1.65g, 1.45mmole), K2CO3(10.0g, 72.8mmole), compound I (8.5g, 18.2 mmole) and 4- (1- phenyl -1H- benzo [d] imidazoles -2- base) phenylboric acid (12.6g, 40.1mmole) merging 500mL In double-necked round bottom bottle, 80mL toluene, 55mL ethyl alcohol and 25mL deionized water is added, is heated to flowing back.After reacting overnight, it is added 50mL ethyl acetate is extracted, and filtrate after extraction is added and carries out purification by chromatography with filling gel, is concentrated into thick, addition Methanol 30mL reinforces being precipitated, and organic layer merged filter solid, and obtained 8.1g Off-white solid compound 1-6, yield 52.3%.
It shows below1The measurement result of H NMR.
1H NMR(CDCl3,400MHz)δ9.92(s,1H),8.95(d,1H),8.76(d,1H),8.47(s,1H),8.37 (d,2H), 8.25(d,1H),8.11(s,1H),7.92(d,2H),7.80-7.77(m,3H),7.74-7.70(m,4H), 7.68-7.58(m,5H), 7.57-7.51(m,5H),7.49-7.46(m,1H),7.41-7.35(m,6H),7.31-7.27(m, 4H).
[synthesis example 5]
By compound C (10g, 15.23mmole) and (3- (pyridin-3-yl) phenyl) boric acid (3.18g, 15.99mmole) It is placed in reactive tank, toluene 120ml is added.By K2CO3Reaction is added after being dissolved in 70ml deionized water in (7.38g, 53.3mmole) Slot, is added tetrakis triphenylphosphine palladium (1.23g, 0.76mmole) and EtOH 30ml opens heating and stirring.It is heated to 80 DEG C instead It should the whole night.300ml DI water is added after having reacted, stirs 30 minutes, standing makes its layering, is extracted, will be filtered after extraction Liquid, which is added, carries out purification by chromatography with filling gel, is concentrated into the thick rear hexane 300mL that is added and reinforces being precipitated, organic layer merged Filter solid obtains 5.5g Off-white solid compound 1-7, yield 49.4%.
It shows below1The measurement result of H NMR.
1H NMR(CDCl3,400MHz)δ9.93(s,1H),8.97-8.95(m,2H),8.77(d,1H),8.63(d, 1H),8.53(s, 1H),8.37(d,2H),8.29(d,1H),8.14(s,1H),7.98(t,1H),7.92(d,1H),7.88 (s,1H),7.84(d,1H),7.80(d, 2H),7.77-7.75(m,1H),7.72-7.67(m,3H),7.65-7.64(m, 4H),7.58-7.50(m,3H),7.49-7.47(m,1H), 7.43-7.35(m,4H),7.31-7.26(m,2H).
[synthesis example 6]
By 3- (carbazole -9- base) phenylboric acid (7.21g, 25.13mmol), compound C (15g, 22.84mmol) and carbonic acid Potassium (7.9 g, 57.1mmol) is placed in reaction flask, adds toluene 225ml, ethyl alcohol 38ml, deionized water 76ml, and N on frame2With Condenser pipe simultaneously moves to reaction in oil cauldron, and 80 DEG C of heating stirring.Tetrakis triphenylphosphine palladium (1.32g, 1.14mmol) is added anti- Bottle is answered, after complete reaction and there are many solids to be precipitated, and it is filtered in advance after removing oil bath cooling, filter cake is poured into beaker, and It is filtered after deionized water 100ml stirring 10mins is added, filter cake is dug into beaker, and tetrahydrofuran 3000ml heating is added and stirs It mixes to complete molten, passes through tubing string (20g SiO2), concentrate the filtrate to it is dry have white solid precipitation after, with ethyl acetate come flushed Filter, drying obtain 11.5g compound as white solid 1-9, yield 61.6%.
It shows below1The measurement result of H NMR.
1H NMR(CDCl3,400MHz)δ9.92(s,1H),8.95(d,1H),8.74(d,1H),8.54(s,1H),8.33 (d,2H), 8.30(d,1H),8.17(t,3H),7.91(d,2H),7.83-7.71(m,6H),7.69-7.68(m,3H), 7.66-7.63(m,3H), 7.55-7.51(m,5H),7.49-7.42(m,3H),7.41-7.28(m,6H).
[synthesis example 7]
By (9- phenyl -9H- carbazole -2- base) boric acid (7.21g, 25.13mmol), compound C (15g, 22.84mmol) with Potassium carbonate (7.9g, 57.1mmol) is placed in reaction flask, adds N on toluene 225ml, ethyl alcohol 38ml, deionized water 76ml and frame2 It is moved in oil cauldron with condenser pipe and by reacting, 80 DEG C of heating stirring, tetrakis triphenylphosphine palladium (1.32g, 1.14mmol) is added Reaction flask, after complete reaction and there are many solids to be precipitated, and filters in advance after removing oil bath cooling, filter cake is poured into beaker, And deionized water 100ml stirring is added and filters after ten minutes, filter cake is dug into beaker, and tetrahydrofuran 3000ml heating is added Stirring passes through tubing string (20g SiO to complete molten2), concentrate the filtrate to it is dry have white solid precipitation after, rinsed with ethyl acetate Filtering, obtains 14g compound as white solid 1-10, yield 75% after drying.
It shows below1The measurement result of H NMR.
1H NMR(CDCl3,400MHz)δ9.92(s,1H),8.95(d,2H),8.76(s,1H),8.53(s,1H),8.37 (d,2H), 8.20-8.18(m,3H),8.13(s,1H),8.92-8.90(d,1H),7.78-7.72(m,3H),7.65-7.63 (m,9H),7.58-7.47(m, 5H),7.45-7.42(m,2H),7.37-7.32(m,5H).
[synthesis example 8]
By quinoline -8- boric acid (4.35g, 25.13mmol), compound C (15g, 22.84mmol) and potassium carbonate (7.9g, 57.1 mmol) it is placed in reaction flask, add N on toluene 225ml, ethyl alcohol 38ml, deionized water 76ml and frame2Simultaneously with condenser pipe Reaction is moved in oil cauldron, 80 DEG C of heating stirring.Reaction flask is added in tetrakis triphenylphosphine palladium (1.32g, 1.14mmol), to anti- After answering completely and there are many solids to be precipitated, and removes after oil bath cools down and filters in advance, filter cake is poured into beaker, and deionization is added It is filtered after water 100ml stirring 10mins, filter cake is dug into beaker and tetrahydrofuran 3000ml heating stirring is added to complete molten, Pass through tubing string (20g SiO2), concentrate the filtrate to it is dry have white solid precipitation after, with ethyl acetate come washing and filtering, after drying Obtain 12g compound as white solid 1-11, yield 74.5%.
It shows below1The measurement result of H NMR.
1H NMR(CDCl3,400MHz)δ9.90(s,1H),8.98-8.97(m,2H),8.73-8.72(d,1H),8.59 (s,1H), 8.36(d,3H),8.25(d,1H),8.15(s,1H),7.90(d,3H),7.89-7.86(m,1H),7.77(d, 2H),7.72-7.65(m,4H), 7.64-7.61(m,2H),7.53-7.50(m,3H),7.48-7.44(m,2H),7.37- 7.33(m,3H),7.28-7.24(m,2H).
[synthesis example 9]
Compound C (10g, 15.23mmole) and (10- phenylanthracene -9- base) boric acid (4.99g, 16.75mmole) are placed in Toluene 120ml is added in reactive tank.By K2CO3Reactive tank is added after being dissolved in 70ml deionized water in (7.36g, 53.3mmole), is added Tetrakis triphenylphosphine palladium (0.88g, 0.76mmole) and ethyl alcohol 30ml open heating and stirring.It is heated to 80 DEG C of reactions the whole night.Instead 300ml DI water is added after having answered, stirs 30min, standing makes its layering, extracted, and filtrate after extraction is added to fill out It fills silica gel and carries out purification by chromatography, be concentrated into the thick rear hexane 300mL that is added and reinforce being precipitated, organic layer merged filter solid, and obtained To 7g faint yellow solid compound 1-13, yield 55.4%.
It shows below1The measurement result of H NMR.
1H NMR(CDCl3,400MHz)δ9.90(s,1H),8.95-8.93(m,1H),8.74-8.73(m,1H),8.58 (d,1H), 8.38(s,1H),8.33(d,2H),8.14(s,1H),7.91(d,1H),7.86(t,1H),7.74-7.50(m, 17H),7.49-7.43(m,1H), 7.38-7.34(m,7H),7.30-7.25(m,4H).
[synthesis example 10]
By 1- pyrene boric acid (2.6g, 10.6mmol), compound C (5.8g, 8.8mmol) and potassium carbonate (2.4g, It 17.6mmol) is placed in reaction flask, adds N on toluene 160ml, ethyl alcohol 110ml, deionized water 50ml and frame2Simultaneously with condenser pipe Reaction is moved in oil cauldron, 80 DEG C of heating stirring.Reaction flask is added in tetrakis triphenylphosphine palladium (0.5g, 0.44mmol).Reaction After overnight, after removing oil bath cooling, ethyl acetate 100ml extraction is added, collected organic layer, concentration are added methanol 20ml and are precipitated Solid obtains 3.94g gray solid compound 1-20, yield 57.4% after filtering drying.
It shows below1The measurement result of H NMR.
1H NMR(CDCl3,400MHz)δ9.91(s,1H),8.92(d,1H),8.73(d,1H),8.51(s,1H),8.42 (d,1H), 8.34(d,2H),8.28(d,1H),8.23-8.17(m,3H),8.15-8.13(m,3H),8.09-8.01(m, 3H),7.91(d,1H), 7.84-7.82(m,1H),7.79-7.74(m,3H),7.69-7.68(m,2H),7.56-7.50(m, 3H),7.44-7.41(m,1H), 7.37-7.34(m,3H),7.29-7.25(m,2H).
The physics value of above-mentioned material is shown in table 2.The measuring method of each physics value is as follows.
(1) thermal cracking temperature (Td)
It is measured using thermogravimetric analyzer (Perkin Elmer, TGA8000), under normal pressure and tool nitrogen atmosphere, with 20 DEG C/min of programmed rate measures the thermal cracking property of compound obtained, and weight has been decreased to 95% temperature of starting weight amount is thermal cracking temperature (Td)。
(2) glass transition temperature (Tg)
Use differential scanning calorimetry instrument (DSC；Perkin Elmer, DSC8000) with 20 DEG C/min of temperature programming speed Rate measures compound obtained.
(3) the energy rank value of highest occupied molecular orbital (HOMO)
In addition, filminess is made in compound, under atmosphere using Photoelectron Spectrophotometer (Riken Keiki, Surface Analyzer) its ionization potential numerical value is measured, it is that HOMO can rank value after its numerical value is further converted.
(4) the energy rank value of lowest unoccupied molecular orbital (LUMO)
The film of above compound is measured into its absorption with UV/VIS spectrophotometer (Perkin Elmer, Lambda20) The boundary value (onset) of wavelength, by the value it is converted edge energy, so that the numerical value of edge energy and HOMO rank is subtracted each other to get LUMO can rank.
(5) triplet energies value (ET)
Luminescent spectrum is measured under temperature 77K using Fluorescence Spectrometer (Perkin Elmer, LS55), then via calculating, E can be obtainedT。
Table 2
Embodiment 1: the manufacture of organic electroluminescence device
Before substrate is loaded into deposition system, degreasing is first carried out with solvent and ultraviolet and ozone cleaning base plate.Later, by base Plate is sent to vacuum deposition chamber, deposits all layers in the top of substrate.Under the vacuum degree of about 10-6 support, the vapor deposition of heating is used Following each layers shown in boat (boat) deposited in sequential Fig. 2:
A) anode thickness 135nm
B) hole injection layer: 20 nanometers of thickness, include the HTM doped with 9%p type electrical conductivity dopant, wherein the p Type electrical conductivity dopant system is purchased from Shanghai Han Feng Chemical Co., Ltd., and the HTM system is purchased from Merck&Co., Inc.；
C) hole transmission layer: 170 nanometers of thickness, HTM；
D) exciton barrier-layer: 10 nanometers of thickness, HT (preparation of sunlight radium photoelectricity)；
E) luminescent layer: 25 nanometers of thickness, include the EBH doped with 4% volume ratio BD, wherein BD and EBH is sunlight radium photoelectricity Preparation；
F) electron transfer layer: 25 nanometers of thickness, the quinoline lithium containing compound 1-2 (client is planned to invite to confirm) and doping (Liq, the preparation of sunlight radium photoelectricity), volume ratio 1:1；
G) electron injecting layer: 0.5 nanometer of thickness, lithium fluoride (LiF)；And
H) cathode, about 180 nanometers of thickness, include A1.
Device architecture can indicate such as: ITO/HTM:p type electrical conductivity dopant (20 nanometers)/HTM (170 nanometers)/HT (10 nanometers)/EBH:BD (25 nanometers)/compound 1-2:Liq (25 nanometers)/LiF (0.5 nanometer)/Al (180 nanometers).
After deposition forms above layers, which is sent in drying box, immediately with the curable ring of UV Oxygen resin and glass cover-plate containing hygroscopic agent are packaged.The organic electroluminescence device has 9 square millimeters of luminous zone Domain.
Embodiment 2~5: the manufacture of organic electroluminescence device
Except the compound 1-2 of electron transfer layer in embodiment 1 is distinctly replaced into compound 1-3,1-7,1-12,1-13 Outside, remaining all manufactures organic electroluminescence device in the same manner as in example 1.Also, the layer structure of embodiment 2~5 and implementation Example 1 is identical.
Comparative example 1: the manufacture of organic electroluminescence device
The structure of organic electroluminescence device is made it is similar with the layer structure of embodiment 1, in addition to by electronics in embodiment 1 The compound 1-2 of transport layer is replaced into compound EET09, which may be expressed as: ITO/HTM:p Dopant (20 nanometers)/HTM (170 nanometers)/HT (10 nanometers)/EBH:BD (25 nanometers)/(25 receive compound EET09:Liq Rice)/LiF (0.5 nanometer)/Al (180 nanometers).
Wherein, compound EET09 is as described in Japanese Patent No. 2011003793A.
The polarimetry nature that is electrically excited of the above-mentioned organic electroluminescence device being made uses constant current source (KEITHLEY 2400 Source Meter, made by Keithley Instruments, Inc., Cleveland, Ohio) and photometer (PHOTO RESEARCH SpectraScan PR 650, made by PhotoResearch, Inc., Chatsworth, Calif. its luminosity) is measured at room temperature, and (standard value is on the basis of the organic electroluminescence device of comparing embodiment 1) value for, driving it voltage, luminous efficiency and LT95 is shown in table 3.Wherein, the luminance level that is defined as of LT95 value is reduced to Time consumed by level relative to the 95% of original intensity is the service life as assessment organic electroluminescence device Or the measurement standard of stability.
Table 3
As shown in table 2, the diphenylpyrimidin through benzimidazole substitution indicated relative to comparative example, the present invention with formula (I) Compound thermal cracking temperature (T with higherd) and glass transition temperature (Tg), and as shown in table 3, using the present invention with formula (I) organic electroluminescence device made of the diphenylpyrimidin compound through benzimidazole substitution of expression has compared with comparative example The good service life.
Therefore, the present invention with high thermal cracking temperature, high glass transition temperature and long-life with formula (I) indicate through benzene And the diphenylpyrimidin compound of imidazoles substitution can improve the problem of prior art, have high technological value, and use with Organic electroluminescence device made of the diphenylpyrimidin compound through benzimidazole substitution of formula (I) expression, especially suitable for Vehicle display or OLED illumination source.
Above-described embodiment is only to be illustrated, and is not intended to limit the present invention, the rights protection scope of the present invention by The claim of the present invention is defined.Also, any the person skilled in the art is in the spirit and model without prejudice to the present invention Under farmland, the present invention is modified, replaced, omitted or is converted and winner is all included in the claim of the present invention.

Claims (15)

1. a kind of diphenylpyrimidin compound through benzimidazole substitution is to be indicated with following formula (I),
Wherein, X1Expression is substituted or is unsubstituted its (C6-C30) aryl, is substituted or is unsubstituted its (5- to 30- member) miscellaneous Aryl；
Ar expression is substituted or is unsubstituted its (C6-C30) aryl, is substituted or is unsubstituted its (5- to 30- member) heteroaryl；
X1And Ar is identical or different, and at least one is to be substituted or be unsubstituted its (5- to 30- member) heteroaryl；
N indicates 1 or 2 integer, and when n indicates 2, Ar is respectively identical or different.
2. the diphenylpyrimidin compound through benzimidazole substitution as described in claims 1, be with formula (I-1), formula (I-2) or Formula (I-3) representation:
Wherein, X1Expression is substituted or is unsubstituted its (C6-C30) aryl, is substituted or is unsubstituted its (5- to 30- member) miscellaneous Aryl；
Ar expression is substituted or is unsubstituted its (C6-C30) aryl, is substituted or is unsubstituted its (5- to 30- member) heteroaryl；
X1And Ar is identical or different, and at least one is to be substituted or be unsubstituted its (5- to 30- member) heteroaryl；
N indicates 1 or 2 integer, and when n indicates 2, Ar is respectively identical or different.
3. the diphenylpyrimidin compound through benzimidazole substitution as described in claims 1, wherein X1For pyridyl group, quinolyl or Naphthalene.
4. the diphenylpyrimidin compound through benzimidazole substitution as described in claims 1 or 2, wherein X1System is selected from following group At one of group person:
Wherein, Xr indicates hydrogen, fluorine, cyano, C1-4 alkyl or the C6-18 aryl being unsubstituted.
5. the diphenylpyrimidin compound through benzimidazole substitution as described in claims 1 or 2, wherein Ar system is selected from following institute Form one of group person:
Wherein, L indicates O or S；
Ar1To Ar6Each independent C6-18 aryl for indicating hydrogen, being unsubstituted；
R1To R4Each independent C6-12 aryl, R for indicating hydrogen, being substituted or being unsubstituted1And R2With the common shape of the carbon atom being connected At C6-18 condensed aromatic loop system or R3And R4C6-18 condensed aromatic loop system is collectively formed with the carbon atom being connected；And
Y1And Y2One of them be singly-bound and to be connected to formula (I) compound, another one is hydrogen.
6. the diphenylpyrimidin compound through benzimidazole substitution as described in claims 5, wherein the C6-18 being unsubstituted Aryl system phenyl, and the C6-12 aryl system phenyl being unsubstituted.
7. the diphenylpyrimidin compound through benzimidazole substitution as described in claims 1, wherein when n is 1, which changes Conjunction object is shown in formula (I-4) or formula (I-5):
8. the diphenylpyrimidin compound through benzimidazole substitution as described in claims 1, wherein when n is 2, which changes Conjunction object is formula (I-6) shown,
9. the diphenylpyrimidin compound through benzimidazole substitution as described in claims 8, wherein the Ar is identical structure.
10. the diphenylpyrimidin compound through benzimidazole substitution as described in claims 1,7 or 8 is following compound (1- 1) one of~compound (1-36):
11. the diphenylpyrimidin compound through benzimidazole substitution as described in claims 1 or 2, heteroaryl contain at least one It is a selected from by the hetero atom in the formed group of N, O and S.
12. a kind of organic electroluminescence device, includes:
Cathode；
Anode；And
Organic layer: between the cathode and anode, contain replacing as described in any one of claims 1 to 11 through benzimidazole Diphenylpyrimidin compound.
13. the organic electroluminescence device as described in claims 12, wherein the organic layer is selected from by electron transfer layer, electronics At least one of implanted layer, luminescent layer, hole blocking layer or electronic barrier layer.
14. the organic electroluminescence device as described in claims 12 or 13, wherein the organic layer is electron transfer layer, and it is thick Degree is 20 nanometers to 30 nanometers.
15. the organic electroluminescence device as described in claims 13 or 14, wherein the electron transfer layer contains N-type electrical conductivity Dopant, the content of the N-type electrical conductivity dopant are 0 weight % to 50 weight %.
CN201810770572.6A 2018-07-13 2018-07-13 Diphenylpyrimidin compound and its organic electroluminescence device through benzimidazole substitution Pending CN109081830A (en)

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