CN109553624A - A kind of compound and its application in organic electroluminescence device - Google Patents

A kind of compound and its application in organic electroluminescence device Download PDF

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CN109553624A
CN109553624A CN201710871493.XA CN201710871493A CN109553624A CN 109553624 A CN109553624 A CN 109553624A CN 201710871493 A CN201710871493 A CN 201710871493A CN 109553624 A CN109553624 A CN 109553624A
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substituted
aromatic hydrocarbon
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高文正
何恩方
任雪艳
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Beijing Eternal Material Technology Co Ltd
Guan Eternal Material Technology Co Ltd
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Beijing Eternal Material Technology Co Ltd
Guan Eternal Material Technology Co Ltd
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Abstract

The present invention relates to a kind of novel general formula compounds to be indicated by formula (I):Wherein: Ar1Selected from C6‑C50Substituted or unsubstituted aromatic hydrocarbon group or condensed-nuclei aromatics group, Ar2、Ar3It is respectively and independently selected from C6‑C50Substituted or unsubstituted aromatic hydrocarbon group or condensed-nuclei aromatics group, C6‑C50Substituted or unsubstituted heteroaryl hydrocarbon or condensed hetero ring aromatic hydrocarbon group.It include at least one compound stated by above-mentioned general formula in organic luminous layer the invention further relates to a kind of organic electroluminescence device.

Description

A kind of compound and its application in organic electroluminescence device
Technical field
The present invention relates to a kind of application of novel general formula compound and the compound in organic electroluminescence device, together When be related to organic electroluminescence device using such compound.
Background technique
Organic electroluminescence device has low solid-state self-luminous, driving voltage, fast response time, angular field of view wide and can It is finely tuned by chemical structure and changes luminescent properties and make rich in color, high resolution easy to accomplish, light-weight, large-area flat-plate are shown The advantages that, it is known as " 21 century flat panel display ", becomes the subjects such as material, information, physics and flat display field research Hot spot.Report that it is luminous for preparing by vacuum deposition method with Alq3 for the first time from Kodak C.W.Tang in 1987 et al. Since the bi-layer devices structure [Appl.Phys.Lett.51,913,1987] of material, organic functional material has just obtained people Very big concern, for example, hole-injecting material, hole mobile material, hole barrier materials, electron injection material, electron-transport Material, electron-blocking materials and light emitting host material and light-emitting guest (dyestuff) etc..
Determine that the most important factor of luminous efficiency is luminescent material in organic electroluminescence device.By luminescence mechanism point Class, electroluminescent organic material can be divided into fluorescence (singlet S0Decaying) and phosphorescence (triplet state T0Decaying) electroluminescent material. Since spin statistics are theoretical, it is found that fluorescent material can utilize singlet excitons, the theoretical quantum efficiency limit is only 25%, and Phosphor material can utilize triplet (75%) and singlet excitons (25%), so that phosphorescent organic electroluminescent diode (OLED) internal quantum efficiency theoretically can reach 100%.So far, fluorescent material has been widely used as luminescent material. 1997, Forrest etc. had found electrophosphorescence phenomenon, and the internal quantum efficiency of electroluminescent organic material breaches 25% Limitation；How remaining 75% phosphorescence is further made full use of to realize that higher luminous efficiency has become in the current field Hot research direction.
But phosphor material makes the reduction of its phosphorescence quantum efficiency due to concentration quenching and T-T annihilation effect.For It avoids concentration quenching and the T-T annihilation effect to obtain high performance organic electro phosphorescent device, will usually contain There are heavy metal phosphorescent emitters to be doped in suitable material of main part, improves phosphorescent emissions efficiency.Luminescent layer material of main part needs Have following characteristics: there is high fluorescence or phosphorescence quantum efficiency；The emission peak of red, green, blue color is as narrow as possible, to obtain Excitation purity；Stability and good film-forming property are able to carry out vapor deposition etc.；Reversible electrochemical redox current potential；With adjacent sky The HOMO and LUMO that cave and electron transfer layer match can the rank (weights that the absorption spectrum of dyestuff and the emission spectrum of main body have had It is folded) i.e. main body is adapted to the energy of dyestuff, hole and electron transport ability match, it is conducive to good between fluorescent dye or phosphorescent coloring Good energy transfer；Suitable singlet or triplet state energy gap are used to control exciton in luminescent layer.
Therefore, for efficient Organic Light Emitting Diode, it is most important to develop suitable high performance material of main part.Make It is very crucial for panchromatic colour developing and solid-state lighting for one of three primary colours.However efficiently phosphorescent devices are seldom, main cause It is a lack of suitable material of main part.
Currently, the material of main part for being widely used in phosphorescent devices has 4,4'-N, N', mono- or two carbazole, one biphenyl (CBP), 2,2 '- Two (9- phenyl -9H- carbazole -2- base) -5,5 '-dialkyl group dithienos [3,2-b:3 ', 2 '-d] pentamethylene, phosphorescence iridium metals are matched Close object, 6, the structure [201310250961] of 6 disubstituted -6-H- benzo [cd] pyrene classes, but these material of main parts all there is Certain defect, such as the thermal stability of CBP are lower, and driving voltage is higher, glass transition temperature (Tg) is low (Tg=62 DEG C), It is easy to crystallize and CBP is a kind of p-type material, hole mobility is much higher than electron mobility, is unfavorable for carrier injection and transmission Perhaps itself and adjacent layer functional material energy level mismatch or the injection imbalance of carrier etc. balance, so that organic electroluminescence phosphorus Optical device the problems such as there are still service life or lower phosphorescence quantum efficiencies, it cannot still obtain the higher organic electrophosphorescenpolymer device of performance Part.
The material of main part of bipolarity group, which can either transmit hole, can also transmit electronics, can be improved organic electroluminescent The performance of device and the extensive concern for causing people.But the thermal stability of current bipolarity phosphorescent light body material is lower and current-carrying Sub- transmission performance is still undesirable, therefore developing function admirable bipolarity phosphorescent light body material there is reality to anticipate the development of OLED Justice.
Summary of the invention
The Organic Electricity that the technical problem to be solved in the present invention is to provide a kind of operating voltages is low, luminous efficiency is high, the service life is long Electroluminescence device.Such novel electroluminescent device has selected a kind of novel phosphorescent light body material.
Another technical problems to be solved of the invention are to provide a kind of novel general formula compound of good performance.
The present invention provides a kind of novel general formula compounds with dibenzothiophenes diindyl structure, have such as formula (I) Shown in structural formula:
Wherein:
Ar1Selected from C6-C50Substituted or unsubstituted aromatic hydrocarbon group or condensed-nuclei aromatics group, Ar2、Ar3It is respectively and independently selected from C6-C50Substituted or unsubstituted aromatic hydrocarbon group or condensed-nuclei aromatics group, C6-C50Substituted or unsubstituted heteroaryl hydrocarbon or thick miscellaneous Aromatic hydrocarbon group.
As above-mentioned Ar1、Ar2And Ar3It is respectively and independently selected from substituted aromatic hydrocarbon group, condensed-nuclei aromatics group and Ar2And Ar3 When being respectively and independently selected from substituted heteroaryl hydrocarbon or condensed hetero ring aromatic hydrocarbon group, substituent group thereon is independently selected from halogen, cyano, nitre Base, or it is selected from C1~C10Alkyl or cycloalkyl, alkenyl, C1~C6Alkoxy or thio alkoxy group, or be selected from C6~C30 Mononuclear aromatics or condensed-nuclei aromatics group, contain be selected from N, O, S, Si hetero atom and C6~C30Mononuclear aromatics or condensed-nuclei aromatics Group, or it is selected from Si (R1)3, the R1Selected from C1~C6Alkyl.
Further, Ar2And Ar3It can be interconnected to form cyclic structure, such ring structure can be aliphatic monocyclic Or polycyclic, aromatic monocycle or condensed ring, such as two groups connect to form aliphatic five-membered ring, hexatomic ring, the ring of composition It can have substituent group in structure.
Further, Ar2And Ar3It is preferred that identical.
Specifically, as the above-mentioned Ar of definition1、Ar2And Ar3When being respectively and independently selected from aromatic hydrocarbon group, refer to selected from a fixed number Aromatics ring system of mesh ring skeleton carbon atom, including single ring architecture substituent group such as phenyl etc. also include being covalently attached structure Aromatic ring substituents group is such as xenyl, terphenyl.
Specifically, as the above-mentioned Ar of definition1、Ar2And Ar3Refer to when being respectively and independently selected from condensed-nuclei aromatics group with a fixed number The aromatics ring system, including condensed cyclic structure substituent group such as naphthalene, anthryl etc. of mesh ring skeleton carbon atom, also take including condensed cyclic structure For the building stone such as benzene binaphthyl, naphthalene xenyl, biphenyl dianthranide base etc. that group is connected with single ring architecture aryl, further include The thick aromatic ring substituents for being covalently attached structure are rolled into a ball such as binaphthyl.
Specifically, as the above-mentioned Ar of definition2And Ar3Refer to when being respectively and independently selected from heteroaryl hydrocarbon or condensed hetero ring aromatic hydrocarbon group and includes One or more is selected from B, N, O, S, P (=O), the hetero atom of Si and P and monocycle or fused ring aryl with ring carbon atom.
Further, in formula (I), Ar1It preferably is selected from C6-C15Substituted or unsubstituted aromatic hydrocarbon group or condensed-nuclei aromatics base Group, Ar2、Ar3Independently it preferably is selected from C6-C15Substituted or unsubstituted aromatic hydrocarbon group or condensed-nuclei aromatics group, C6-C15Take Generation or unsubstituted heteroaryl hydrocarbon or condensed hetero ring aromatic hydrocarbon group.And work as Ar1Selected from substituted aryl, condensed-nuclei aromatics group and Ar2 And Ar3When selected from substituted aryl, condensed-nuclei aromatics group, heteroaryl or condensed hetero ring aromatic hydrocarbon group, the substituent group thereon is only It is vertical preferably to be selected from F, cyano, or it is selected from C1~C6Alkyl or cycloalkyl, Si (CH3)3, alkenyl, alkoxy or thio alkoxy base Group, or it is independently selected from C6-C15Monocycle or condensed-nuclei aromatics group, contain be selected from N or O hetero atom and C6-C15Monocycle or Condensed-nuclei aromatics group.
Further, in formula (I), Ar1、Ar2And Ar3Independently preferred aromatic hydrocarbons or condensed-nuclei aromatics group include: benzene Base, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, indenyl, fluoranthene base, 9,9- dimethyl fluorenyl, fluorenyl, indeno fluorenyl, three Phenylene, pyrenyl, base,Base or aphthacene base；The phenyl replaced by furyl, thienyl, pyrrole radicals and/or pyridyl group.
Above-mentioned xenyl is preferably 2- xenyl, 3- xenyl and 4- xenyl, and above-mentioned terphenyl is preferably p- three Phenyl -4- base, p- terphenyl -3- base, p- terphenyl -2- base, m- terphenyl -4- base, m- terphenyl -3- base With m- terphenyl -2- base；Above-mentioned naphthalene is preferably 1- naphthalene and/or 2- naphthalene；Above-mentioned anthryl is preferably 1- anthryl, 2- anthracene Base or 9- anthryl；Above-mentioned pyrenyl is preferably 1- pyrenyl, 2- pyrenyl or 4- pyrenyl；Above-mentioned aphthacene base be preferably 1- aphthacene base, 2- aphthacene base or 9- aphthacene base.
Further, in formula (I), Ar2And Ar3Independently preferred heteroaryl or thick heteroaryl groups include: furans Base, benzofurane base, thienyl, tolylthiophene base, pyrrole radicals, phenylpyrrole base, pyridyl group, phenylpyridyl, pyrazinyl, quinoline Quinoline, triazine radical, benzofuranyl, benzothienyl, phentriazine, benzopyrazines, isobenzofuran-base, indyl, benzo quinoline Diazole, the coffee that quinoline, dibenzofuran group, dibenzothiophene, dibenzopyrrole base, carbazyl and its derivative, phenyl replace At least one of quinoline base, coffee quinoline benzothiazolyl and benzodioxole group, wherein the carbazole radical derivative can be with At least one including but not limited in 9- phenyl carbazole, 9- naphthyl carbazole benzo carbazole, dibenzo-carbazole and indolocarbazole Kind.
The expression way of above-mentioned Ca~Cb represents the carbon atom number that the group has as a~b, unless specifically indicated, generally For the carbon atom number do not include substituent group carbon atom number.
In a preferred embodiment of the present invention, for filming performance and processing performance aspect the considerations of, described The molecular weight of compound is between 400~1200, between preferably 450~1100.
Further, following specific structure compounds can preferably be gone out in conjunction with general formula of the invention, these compounds are only It is representative:
The present invention also provides compounds described in above-mentioned general formula (I) to prepare the purposes in organic electroluminescence device.
Organic electroluminescence device generally comprises first electrode, second electrode and is located at the first electrode and second electrode Between one or more layers organic function layer usually have electron injection as the organic layer between first electrode and second electrode The organic layers such as layer, electron transfer layer, luminescent layer, hole transmission layer, hole injection layer.The compound of the present invention may be used as but not It is limited to light emitting host material.
The present invention also provides a kind of organic electroluminescence device, which includes first electrode, second electrode and is located at One or more layers organic layer between the first electrode and second electrode includes at least one in the organic layer by general formula (I) compound indicated:
Wherein:
Ar1Selected from C6-C50Substituted or unsubstituted aromatic hydrocarbon group or condensed-nuclei aromatics group, Ar2、Ar3It is respectively and independently selected from C6-C50Substituted or unsubstituted aromatic hydrocarbon group or condensed-nuclei aromatics group, C6-C50Substituted or unsubstituted heteroaryl hydrocarbon or thick miscellaneous Aromatic hydrocarbon group.
As above-mentioned Ar1、Ar2And Ar3When being respectively and independently selected from substituted aromatic hydrocarbon group, condensed-nuclei aromatics group and Ar2With Ar3When being respectively and independently selected from substituted heteroaryl hydrocarbon or condensed hetero ring aromatic hydrocarbon group, substituent group thereon is independently selected from halogen, cyanogen Base, nitro, or it is selected from C1~C10Alkyl or cycloalkyl, alkenyl, C1~C6Alkoxy or thio alkoxy group, or be selected from C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, contain be selected from N, O, S, Si hetero atom and C6~C30Mononuclear aromatics or thick Aromatic hydrocarbon group, or it is selected from Si (R1)3, the R1Selected from C1~C6Alkyl.
Further, Ar2And Ar3It can be interconnected to form cyclic structure, such ring structure can be aliphatic monocyclic Or polycyclic, aromatic monocycle or condensed ring, such as two groups connect to form aliphatic five-membered ring, hexatomic ring, the ring of composition It can have substituent group in structure.
The present invention, as mother nucleus structure, devises a kind of new compound by using dibenzothiophenes diindyl structure. Dibenzothiophenes diindyl structure glass transition temperature with higher of the invention and good thermodynamic stability, and have There are very strong electron-withdrawing ability and higher triplet, simultaneously synthesizing method is simple and easy to get.
The Molecular Design thinking that the present invention uses is to introduce electrophilic in parent nucleus dibenzothiophenes diindyl structure Group quinazoline, to improve the electronic transmission performance of material；Further, draw on quinazoline and dibenzothiophenes diindyl structure Enter electron-donating group Ar1, Ar2And Ar3, to improve the hole transport performance of material, the compound of the present invention is a kind of bipolar transmission Material, can be with simultaneous transmission hole and electronics, and then increases the recombination region for widening charge, improves luminous efficiency.
Such dibenzothiophenes diindyl structural derivative with bipolar transmission performance is applied to organic electroluminescent When in device, as the material of main part of bipolar transmission performance, there is efficiently balanced carrier transmission performance, and there is height Exciton transition rate and frequency make the triplet of such material higher, can be suitable for efficient organic electroluminescence send out Optical device.Wherein, higher triplet can effectively prevent energy in luminescence process from returning to material of main part, greatly improve The luminous efficiency of organic electroluminescence device, brightness, and its driving voltage is reduced, extend the service life of organic electroluminescence device.
Detailed description of the invention
From the detailed description with reference to the accompanying drawing to the embodiment of the present invention, these and/or other aspects of the invention and Advantage will become clearer and be easier to understand, in which:
Fig. 1: compound C-1's1H-NMR figure
Specific embodiment
In order to make those skilled in the art more fully understand the present invention, with reference to the accompanying drawings and detailed description to this hair It is bright to be described in further detail.
The compound for the synthetic method that do not mention in the present invention is all the raw produce being obtained through commercial channels.Implement Various chemicals such as petroleum ether, ethyl acetate, n-hexane, toluene, tetrahydrofuran, methylene chloride, four chlorinations used in example Bis- (bromomethyl) benzene of carbon, acetone, 1,2-, CuI, o-phthaloyl chloride, phenylhydrazine hydrochloride, trifluoroacetic acid, acetic acid, trans--diamino Hexamethylene, iodobenzene, cesium carbonate, potassium phosphate, ethylenediamine, benzophenone, cyclopentanone, 9-Fluorenone, sodium tert-butoxide, Loprazolam, 1- Bromo- 2- methyl naphthalene, o-dibromobenzene, butyl lithium, Bromofume, o-dibromobenzene, benzoyl peroxide, 1- (2- bromophenyl) -2- first Base naphthalene, N- bromo-succinimide, methoxyl methyl San Jia Ji phosphonium chloride, tris(dibenzylideneacetone) dipalladium, four (triphenylphosphines) Palladium, 1,3- pairs of 2-phenyl-phosphine oxide nickel chloride, carbazole, 3,6- di-t-butyl carbazole, N- phenyl carbazole -3- bromine, 2- bromine Fluorenone, The basic chemical industries raw materials such as 2- (4- bromobenzene) -4,6- diphenyl triazine chemical products can be commercially available at home.
The analysis detection of intermediate and compound in the present invention uses ABSCIEX mass spectrograph (4000QTRAP) He Bulu Gram Nuclear Magnetic Resonance (400M).
The synthetic example of compound:
Novel general formula compound C-1 to C-72 proposed by the present invention can be prepared by following reaction scheme:
Reaction scheme
Representative structure compound C-1, C-53 and C-67 in following embodiment detailed description of the present invention general formula compound Specific preparation method:
Synthetic example 1: the preparation of compound C-1
The preparation of compound 1-1
By 4-bromine of compound dibenzo [b, d] thiophene (32.4g, 200mmol), carbazole (40g, 240mmol), cuprous iodide (38g, 200mmol), ethylenediamine (12g, 200mmol), cesium carbonate (130g, 0.4mol) are suspended in after 400mL o-dichlorohenzene It reacts for 24 hours, is spin-dried under nitrogen atmosphere, column chromatographs petroleum ether: methylene chloride=10:1 obtains product 1-1 (22g, 63mmol).
The preparation of compound 1-2
- 40 DEG C of dry ice acetone bath or so, N2S-butyl lithium is added drop-wise in 1h under atmosphere reaction substrate 1-1 (22g, In THF solution 0.063mol), drop finishes, and keeps -25 DEG C of constant reaction 2h, trimethylborate is added dropwise after being cooled to -60 DEG C, drips Finish, is raised to room temperature reaction 2h naturally；
White solid is precipitated after 25mLHCl solution is added dropwise, continues to be stirred to react 1h, filters, filtrate adds ethyl acetate to extract, Liquid separation, the extraction of water phase ethyl acetate merge organic phase, and saturated common salt water washing, anhydrous sodium sulfate is dry, filters, and decompression is spin-dried for Grease crude product is obtained, is chromatographed with PE:DCM=9:1 column, decompression is spin-dried for obtaining 1-2 (29.7g, 0.053mol) off-white powder.
The preparation of compound 1-3
By product 1-2 (10g, 25.4mmol), bromo nitryl benzene (4.96g, 24.7mmol) and Pd (PPh3)4(0.32g, It 0.254mmol) is dissolved in the mixture of dioxane (180mL) and water (60mL), it is anti-under the conditions of nitrogen protection, 100 DEG C Answer 12h.Reaction mixture is cooled to room temperature and is spin-dried for, is filtered by column, obtain compound 1-3 (10.5g, 0.225mol, 52.94%)
The preparation of compound 1-4
Compound 1-3 (17.5g, 37.2mmol), triphenyl phosphorus (24.4g, 93.1mmol) and 300mL o-dichlorohenzene is mixed After conjunction, in cooling for reflux 36h.Reaction mixture is cooled to room temperature, decompression is carried out and is spin-dried for, filtered by column, obtain chemical combination Object 1-4 (10.6g).
The preparation of compound 1-5
By raw materials of compound (2.34g, 11.9mmol), compound phenyl boric acid (1.45g, 11.9mmol), Pd (PPh3)4 (0.7g, 0.59mmol) and Na2CO3(3.8g, 35.7mmol) is dissolved in the mixing of dioxane (55mL), distilled water (14mL) After in object, it is condensed back reaction 12h.Then column is crossed with PE/EA, obtains compound 1-5 (2.0g, 8.8mmol, 73.9%)
The preparation of compound C-1
By compound 1-4 (7g, 16mmol), K2CO3(6.62g, 48mmol) and product 1-5 (4.61g, 19.2mmol) are molten Solution is in DMF, cooling for reflux 12h.Reaction mixture is cooled to room temperature, decompression is carried out and is spin-dried for, filtered by column, obtain chemical combination Object 1-4 (12.5g, 78%).
1H NMR(500MHz,δ,CDCl3): 8.66 (d, J=15.0Hz, 1H), 8.55 (dd, J=14.2,3.7Hz, 2H), 8.41 (dd, J=15.0,2.9Hz, 1H), 8.26-8.08 (m, 2H), 8.04-7.93 (m, 2H), 7.88-7.73 (m, 4H), 7.70-7.59 (m, 2H), 7.59-7.34 (m, 6H), 7.25-7.04 (m, 6H) (m/z): 642. elemental analyses: theoretical value: C, 82.22；H,4.08,N,8.72；S, 4.99, measured value: C, 82.23；H,4.10,N,8.70；S,4.98
Synthetic example 2: the preparation of compound C-53
The preparation of compound 2-1
By 4-bromine of compound dibenzo [b, d] thiophene (32.4g, 200mmol), 2- (9,9- dimethyl-2- aminofluorene) naphthalene (80.4g, 240mmol), cuprous iodide (38g, 200mmol), ethylenediamine (12g, 200mmol), cesium carbonate (130g, It 400mmol) is suspended in 400mL o-dichlorohenzene to react under nitrogen atmosphere for 24 hours later, be spin-dried for, column chromatographs petroleum ether: methylene chloride =10:1 obtains product 1-1 (33g, 62.9mmol, 31.5%).
The preparation of compound 2-2
- 40 DEG C of dry ice acetone bath or so, N2S-butyl lithium is added drop-wise in 1h under atmosphere reaction substrate 2-1 (33g, In 62.9mol), drop finishes, and keeps -25 DEG C of (± 5 DEG C) constant reaction 2h, and trimethylborate is added dropwise after being cooled to -60 DEG C, and drop finishes, Naturally it is raised to room temperature reaction 2h；
25mLHCl solution being added dropwise, white solid is precipitated, continue to be stirred to react 1h, filters, filtrate adds ethyl acetate to extract, point Liquid, the extraction of water phase ethyl acetate merge organic phase, and saturated common salt water washing, anhydrous sodium sulfate is dry, filters, and decompression is spin-dried for It to grease crude product, is chromatographed with PE:DCM=9:1 column, decompression is spin-dried for obtaining 2-2 (27.3g, 48.6mmol, 77.3%) off-white color Solid.
The preparation of compound 2-3
Take product 2-2 (14.2g, 25.4mmol), bromo nitryl benzene (4.96g, 24.7mmol) and Pd (PPh3)4(0.32g, It 0.254mmol) is dissolved in the mixture of dioxane (180mL) and water (60mL), it is anti-under the conditions of nitrogen protection, 100 DEG C Answer 12h.Reaction mixture is cooled to room temperature and is spin-dried for, is filtered by column, obtain compound 2-3 (7.29g, 12.15mmol, 49.2%)
The preparation of compound 2-4
Compound 2-3 (7.29g, 12.15mmol), triphenyl phosphorus (8.0g, 30.4mmol) and 100mL o-dichlorohenzene is mixed After conjunction, in cooling for reflux 36h.Reaction mixture is cooled to room temperature, decompression is carried out and is spin-dried for, filtered by column, obtain chemical combination Object 2-4 (6.9g, 11.37mmol).
The preparation of compound 2-5
By raw materials of compound (2.34g, 11.9mmol), compound pyrene boric acid (2.05g, 11.9mmol), Pd (PPh3)4 (0.7g, 0.59mmol) and Na2CO3(3.8g, 35.7mmol) is dissolved in the mixing of dioxane (55mL), distilled water (14mL) After in object, it is condensed back reaction 12h.Then column is crossed with PE/EA, obtains compound 2-5 (2.49g, 8.57mmol, 72.0%)
The preparation of compound C-53
By compound 2-4 (0.97g, 1.6mmol), K2CO3(0.662g, 4.8mmol) and product 2-5 (0.56g, It 1.92mmol) is dissolved in DMF, cooling for reflux 12h.Reaction mixture is cooled to room temperature, decompression is carried out and is spin-dried for, pass through column mistake Filter, obtains compound C-53 (1.1g, 1.28mmol, 80%).
1H NMR(500MHz,δ,CDCl3): 8.55 (dd, J=14.1,3.8Hz, 1H), 8.46 (t, J=3.0Hz, 1H), 8.40 (d, J=15.0Hz, 1H), 8.12 (ddd, J=14.8,10.2,3.0Hz, 2H), 8.08-7.95 (m, 5H), 7.93- 7.84(m,2H),7.83–7.67(m,4H),7.67–7.49(m,8H),7.49–7.18(m,7H),7.18(s,1H),7.18– 7.06 (m, 3H), 7.01 (dd, J=15.0,2.9Hz, 1H), 1.69 (s, 6H) (m/z): 861.30. elemental analysis: theoretical value: C,85.09；H,4.68,N,6.51；S, 3.72 measured values: C, 83.07；H,4.67,N,6.52；S,3.74
Synthetic example 3: the preparation of compound C-67
The preparation of compound C-67
The preparation of compound 3-1
By 4-bromine of compound dibenzo [b, d] thiophene (32.4g, 200mmol), dibenzofurans-2- aniline (62g, 240mmol), cuprous iodide (38g, 200mmol), ethylenediamine (12g, 200mmol), cesium carbonate (130g, 400mmol) are suspended in It reacts for 24 hours, is spin-dried under nitrogen atmosphere after 400mL o-dichlorohenzene, column chromatographs petroleum ether: methylene chloride=10:1 obtains product 1-1 (27.7g, 62.9mmol, 31.5%).
The preparation of compound 3-2
- 40 DEG C of dry ice acetone bath or so, N2S-butyl lithium is added drop-wise in 1h under atmosphere reaction substrate 3-1 (27.7g, In 62.9mol), drop finishes, and keeps -25 DEG C of (± 5 DEG C) constant reaction 2h, and trimethylborate is added dropwise after being cooled to -60 DEG C, and drop finishes, Naturally it is raised to room temperature reaction 2h；
25mLHCl solution being added dropwise, white solid is precipitated, continue to be stirred to react 1h, filters, filtrate adds ethyl acetate to extract, point Liquid, the extraction of water phase ethyl acetate merge organic phase, and saturated common salt water washing, anhydrous sodium sulfate is dry, filters, and decompression is spin-dried for It to grease crude product, is chromatographed with PE:DCM=9:1 column, decompression is spin-dried for obtaining 3-2 (23.6g, 48.6mmol, 77.3%) off-white color Solid.
The preparation of compound 3-3
Take product 3-2 (12.32g, 25.4mmol), bromo nitryl benzene (4.96g, 24.7mmol) and Pd (PPh3)4 (0.32g, 0.254mmol) is dissolved in the mixture of dioxane (180mL) and water (60mL), in nitrogen protection, 100 DEG C of items 12h is reacted under part.Reaction mixture is cooled to room temperature and is spin-dried for, is filtered by column, obtain compound 3-3 (6.83g, 12.15mmol 49.2%)
The preparation of compound 3-4
Compound 3-3 (6.83g, 12.15mmol), triphenyl phosphorus (8.0g, 30.4mmol) and 100mL o-dichlorohenzene is mixed After conjunction, in cooling for reflux 36h.Reaction mixture is cooled to room temperature, decompression is carried out and is spin-dried for, filtered by column, obtain chemical combination Object 3-4 (6.03g, 11.37mmol).
The preparation of compound 3-5
By raw materials of compound (2.34g, 11.9mmol), compound to (4- pyrene) phenyl boric acid (2.95g, 11.9mmol), Pd (PPh3)4(0.7g, 0.59mmol) and Na2CO3(3.8g, 35.7mmol) is dissolved in dioxane (55mL), distilled water (14mL) Mixture in after, be condensed back reaction 12h.Then cross column with PE/EA, obtain compound 3-5 (3.14g, 8.57mmol, 72.0%)
The preparation of compound C-67
By compound 3-4 (0.85g, 1.6mmol), K2CO3(0.662g, 4.8mmol) and product 3-5 (0.70g, It 1.92mmol) is dissolved in DMF, cooling for reflux 12h.Reaction mixture is cooled to room temperature, decompression is carried out and is spin-dried for, pass through column mistake Filter, obtains compound C-67 (1.1g, 1.28mmol, 80%).1H NMR(500MHz,δ,CDCl3): 8.95 (dd, J=14.3, 3.7Hz, 1H), 8.84 (d, J=15.0Hz, 1H), 8.55-8.45 (m, 1H), 8.35-8.26 (m, 2H), 8.23-8.04 (m, 4H), 7.98 (dd, J=14.6,3.4Hz, 1H), 7.92-7.86 (m, 1H), 7.84-7.72 (m, 4H), 7.64 (dd, J= 14.8,3.1Hz, 1H), 7.58-7.49 (m, 2H), 7.46-7.12 (m, 14H), 7.11-6.94 (m, 4H) (m/z): 861.26. Elemental analysis: theoretical value: C, 83.70；H,4.21,N6.51；O,1.86；S, 3.72 measured values: C, 83.68；H,4.23, N6.49；O,1.85；S,3.75
In addition to providing compound C-1 in synthetic example of the present invention, the analysis detecting data of C-53 and C-67 are given The analysis detecting data of compound C-19, C-37, C-45, C-49 and-C50 arrange in table 1 below:
Table 1
Compound Molecular formula Molecular weight Elemental analysis
C-19 C50H32N4S 720.23 C,83.31；H,96；H,4.47；N,7.77；S,4.45
C-37 C48H30N4S 694.22 C,82.97；H,4.35；N,8.06；S,4.61
C-45 C52H30N4S 742.22 C,84.07；H,4.07；N,7.54；S,4.32
C-49 C54H32N4OS 784.23 C,82.63；H,4.11；N,7.14；O,2.04；S,4.09
C-50 C54H32N4S2 800.21 C,80.97；H,4.03；N,6.99；S,8.01
Device embodiments prepared by the compounds of this invention:
The typical structure of the OLED organic electroluminescence device prepared in device embodiments are as follows:
Substrate/anode/hole injection layer (HIL)/hole transmission layer (HTL)/organic luminous layer (EL)/electron transfer layer (ETL)/electron injecting layer (EIL)/cathode
Above-mentioned "/" indicates to be laminated in order between different function layer.
The compounds of this invention can be, but not limited to for luminescent layer material of main part.
Device embodiments 1:
Different materials specific structure used in the present invention is seen below:
Above-mentioned electroluminescent organic material, is all material commonly used in the art in addition to TM5, and those skilled in the art are based on known Method can be prepared voluntarily or be bought from Chemical market.Wherein the compound of TM5 is in Chinese patent application 201310250961 The compound of report can be synthesized into according to the synthetic method disclosed in the patent.
The compound of the present invention is as the material of main part in phosphorescent OLED organic electroluminescence device, organic electroluminescence Part structure are as follows:
ITO (150nm)/NPB (20nm)/material of main part (30nm): Ir (piq)3[5%]/TPBI (10nm)/Alq3 (15nm)/LiF(0.5nm)/Al(150nm)。
The organic electroluminescence device of design two as a comparison case, material of main part select CBP or TM-5, and other 7 have Organic electroluminescence devices (device embodiments 1-7) select the compound of the present invention, specially compound C-1, C-19, C-37, C-45, C-49, C-50 and C-53.
The preparation process of organic electroluminescence device is as follows:
The glass plate for being coated with ITO (thickness 150nm) transparency conducting layer is ultrasonically treated in commercial detergent, go from It is rinsed in sub- water, in acetone: ultrasonic oil removing in alcohol mixed solvent is baked under clean environment and completely removes moisture, with purple Outer light and ozone clean, and with low energy cation beam bombarded surface；The above-mentioned glass substrate with anode is placed in vacuum chamber, It is evacuated to 1 × 10-5~9 × 10-3Pa, vacuum evaporation hole transmission layer NPB, evaporation rate are on above-mentioned anode tunic 0.1nm/s, vapor deposition film thickness are 20nm；Vacuum evaporation light emitting host material and dopant Ir (piq) on hole transmission layer3, As the luminescent layer of organic electroluminescence device, evaporation rate 0.1nm/s, vapor deposition total film thickness is 30nm；On luminescent layer Successively vacuum evaporation electron transfer layer TPBI and Alq3, evaporation rate is 0.1nm/s, vapor deposition film thickness be respectively 10nm and 15nm；The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as cathode.
Organic electroluminescence device performance is shown in Table 2.
Table 2:
It can be seen that by upper table 2
(1) opposite as the organic electroluminescence device of material of main part using the compounds of this invention in phosphorescence luminescent layer In obtaining preferable effect as the organic electroluminescence device of material of main part using CBP, higher current efficiency is obtained With lower driving voltage；
(2) organic electroluminescence device of comparison material of main part TM5 manufacture, is requiring 10000cd/cm2Brightness under, Corresponding driving voltage is 6.1V, and corresponding current efficiency is 8.0d/A, and it is organic to use material of main part of the invention to manufacture Electroluminescent device, in the case where similarly requiring brightness, corresponding voltage most low energy reaches 5.0V, and efficiency reaches as high as 19.2cd/A.
Thus it proves, this kind of dibenzothiophenes diindyl structure of the present invention is as the allusion quotation in the general formula compound of mother nucleus structure Type representation compound is compared with the compound in the prior art that comparative example uses, the stability and work of the compounds of this invention Based on material when carrier transmission performance all have and be extremely obviously improved effect, so the compounds of this invention has very Ideal practical value.There is obvious drop as the organic electroluminescence device that material of main part manufactures using the compound of the present invention Low driving voltage and the advantage for improving luminous efficiency.
The preferred embodiment of the present invention has been described above in detail, still, during present invention is not limited to the embodiments described above Detail within the scope of the technical concept of the present invention can be with various simple variants of the technical solution of the present invention are made, this A little simple variants all belong to the scope of protection of the present invention.
It is further to note that specific technical features described in the above specific embodiments, in not lance In the case where shield, can be combined in any appropriate way, in order to avoid unnecessary repetition, the present invention to it is various can No further explanation will be given for the combination of energy.
In addition, various embodiments of the present invention can be combined randomly, as long as it is without prejudice to originally The thought of invention, it should also be regarded as the disclosure of the present invention.

Claims (10)

1. a kind of general formula compound has the structural formula as shown in formula (I):
Wherein:
Ar1Selected from C6-C50Substituted or unsubstituted aromatic hydrocarbon group or condensed-nuclei aromatics group, Ar2、Ar3It is respectively and independently selected from C6- C50Substituted or unsubstituted aromatic hydrocarbon group or condensed-nuclei aromatics group, C6-C50Substituted or unsubstituted heteroaryl hydrocarbon or condensed hetero ring Aromatic hydrocarbon group；
As above-mentioned Ar1、Ar2And Ar3When being respectively and independently selected from substituted aromatic hydrocarbon group, condensed-nuclei aromatics group and Ar2And Ar3Point When not being independently selected from substituted heteroaryl hydrocarbon or condensed hetero ring aromatic hydrocarbon group, substituent group thereon is independently selected from halogen, cyano, nitre Base, or it is selected from C1~C10Alkyl or cycloalkyl, alkenyl, C1~C6Alkoxy or thio alkoxy group, or be selected from C6~C30 Mononuclear aromatics or condensed-nuclei aromatics group, contain be selected from N, O, S, Si hetero atom and C6~C30Mononuclear aromatics or condensed-nuclei aromatics Group, or it is selected from Si (R1)3, the R1Selected from C1~C6Alkyl.
2. general formula compound according to claim 1, in which:
Ar1Selected from C6-C15Substituted or unsubstituted aromatic hydrocarbon group or condensed-nuclei aromatics group, Ar2、Ar3It is respectively and independently selected from C6- C15Substituted or unsubstituted aromatic hydrocarbon group or condensed-nuclei aromatics group, C6-C15Substituted or unsubstituted heteroaryl hydrocarbon or condensed hetero ring Aromatic hydrocarbon group；
Work as Ar1Selected from substituted aryl, condensed-nuclei aromatics group and Ar2And Ar3Selected from substituted aryl, condensed-nuclei aromatics group, When heteroaryl or condensed hetero ring aromatic hydrocarbon group, the substituent group thereon is independently selected from F, cyano, or is selected from C1~C6Alkyl or ring Alkyl, Si (CH3)3, alkenyl, alkoxy or thio alkoxy group, or be independently selected from C6-C15Monocycle or condensed-nuclei aromatics base The hetero atom and C for being selected from N or O are contained in group6-C15Monocycle or condensed-nuclei aromatics group.
3. general formula compound according to claim 1, in which:
Ar1、Ar2And Ar3Be respectively and independently selected from phenyl, 2- xenyl, 3- xenyl and 4- xenyl, p- terphenyl -4- base, P- terphenyl -3- base, p- terphenyl -2- base, m- terphenyl -4- base, m- terphenyl -3- base and m- three Phenyl -2- base, naphthalene, anthryl, phenanthryl, indenyl, fluoranthene base, 9,9- dimethyl fluorenyl, fluorenyl, indeno fluorenyl, triphenylene, pyrene Base, base,Base, 1- aphthacene base, 2- aphthacene base or 9- aphthacene base aphthacene base；
Or Ar2And Ar3It is respectively and independently selected from the phenyl replaced by furyl, thienyl, pyrrole radicals and/or pyridyl group；Or it is only respectively It is vertical to be selected from furyl, benzofurane base, thienyl, tolylthiophene base, pyrrole radicals, phenylpyrrole base, pyridyl group, pyrimidine radicals, three Piperazine base, phenylpyridyl, pyrazinyl, quinoline, benzofuranyl, benzothienyl, phentriazine, benzopyrazines, different benzo furan It mutters base, indyl, benzoquinoline, dibenzofuran group, dibenzothiophene, dibenzopyrrole base, 9- phenyl carbazole, 9- naphthalene Between diazole, coffee quinoline base, coffee quinoline benzothiazolyl or benzo that carbazole benzo carbazole, dibenzo-carbazole, indolocarbazole, phenyl replace Dioxa cyclopentenyl.
4. general formula compound according to claim 1, wherein Ar2And Ar3Cyclic structure can be interconnected to form.
5. general formula compound according to claim 1, wherein Ar2And Ar3It is identical.
6. general formula compound according to claim 1 or 4 is selected from following concrete structure formulas:
7. application of the general formula compound according to claim 1 or 4 in organic electroluminescence device.
8. application of the structural compounds according to claim 6 in organic electroluminescence device.
9. a kind of organic electroluminescence device, which includes first electrode, second electrode and is located at the first electrode and the One or more layers organic layer between two electrodes, which is characterized in that include at least one in the organic layer by general formula (I) expression Compound:
Wherein: Ar1Selected from C6-C50Substituted or unsubstituted aromatic hydrocarbon group or condensed-nuclei aromatics group, Ar2、Ar3Independently select From C6-C50Substituted or unsubstituted aromatic hydrocarbon group or condensed-nuclei aromatics group, C6-C50Substituted or unsubstituted heteroaryl hydrocarbon or thick Heterocyclic arene group；
As above-mentioned Ar1、Ar2And Ar3It is respectively and independently selected from substituted aromatic hydrocarbon group, condensed-nuclei aromatics group, heteroaryl hydrocarbon or condensed hetero ring virtue When hydrocarbyl group, substituent group thereon is independently selected from halogen, cyano, nitro, or is selected from C1~C10Alkyl or cycloalkyl, alkene Base, C1~C6Alkoxy or thio alkoxy group, or be selected from C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, containing choosing From the hetero atom and C of N, O, S, Si6~C30Mononuclear aromatics or condensed-nuclei aromatics group, or be selected from Si (R1)3, the R1Selected from C1 ~C6Alkyl.
10. a kind of organic electroluminescence device, which includes first electrode, second electrode and is located at the first electrode and the One or more layers organic layer between two electrodes, which is characterized in that include at least one in the organic layer selected from following specific The compound of structural formula:
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110483533A (en) * 2019-07-08 2019-11-22 宁波卢米蓝新材料有限公司 A kind of compound and its preparation method and application

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013081315A1 (en) * 2011-11-28 2013-06-06 덕산하이메탈(주) Compound for organic electronic device, organic electronic device comprising same and electronic device comprising the organic electronic device
CN103249722A (en) * 2010-10-13 2013-08-14 罗门哈斯电子材料韩国有限公司 Novel compounds for organic electronic material and organic electroluminescent device using the same
WO2014038867A1 (en) * 2012-09-07 2014-03-13 Rohm And Haas Electronic Materials Korea Ltd. A novel combination of a host compound and a dopant compound and an organic electroluminescence device comprising the same
KR20150007476A (en) * 2013-07-11 2015-01-21 덕산하이메탈(주) Organic electronic element using a compound for organic electronic element, and an electronic device thereof
WO2015126081A1 (en) * 2014-02-21 2015-08-27 삼성에스디아이 주식회사 Organic optoelectric device and display apparatus
KR101559430B1 (en) * 2012-02-22 2015-10-13 주식회사 엠비케이 Organic light compound and organic light device using the same
US20160028020A1 (en) * 2014-07-24 2016-01-28 Duk San Neolux Co., Ltd. Organic electronic element and an electronic device comprising it
KR101614739B1 (en) * 2015-12-01 2016-04-22 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
WO2016064111A1 (en) * 2014-10-24 2016-04-28 덕산네오룩스 주식회사 Organic electronic device and display apparatus using composition for organic electronic device
WO2017023021A1 (en) * 2015-08-06 2017-02-09 에스에프씨 주식회사 Organic light emitting element having high efficiency
KR20170047653A (en) * 2015-10-23 2017-05-08 삼성디스플레이 주식회사 Organic light emitting device

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103249722A (en) * 2010-10-13 2013-08-14 罗门哈斯电子材料韩国有限公司 Novel compounds for organic electronic material and organic electroluminescent device using the same
WO2013081315A1 (en) * 2011-11-28 2013-06-06 덕산하이메탈(주) Compound for organic electronic device, organic electronic device comprising same and electronic device comprising the organic electronic device
KR101559430B1 (en) * 2012-02-22 2015-10-13 주식회사 엠비케이 Organic light compound and organic light device using the same
WO2014038867A1 (en) * 2012-09-07 2014-03-13 Rohm And Haas Electronic Materials Korea Ltd. A novel combination of a host compound and a dopant compound and an organic electroluminescence device comprising the same
KR20150007476A (en) * 2013-07-11 2015-01-21 덕산하이메탈(주) Organic electronic element using a compound for organic electronic element, and an electronic device thereof
WO2015126081A1 (en) * 2014-02-21 2015-08-27 삼성에스디아이 주식회사 Organic optoelectric device and display apparatus
US20160028020A1 (en) * 2014-07-24 2016-01-28 Duk San Neolux Co., Ltd. Organic electronic element and an electronic device comprising it
WO2016064111A1 (en) * 2014-10-24 2016-04-28 덕산네오룩스 주식회사 Organic electronic device and display apparatus using composition for organic electronic device
WO2017023021A1 (en) * 2015-08-06 2017-02-09 에스에프씨 주식회사 Organic light emitting element having high efficiency
KR20170047653A (en) * 2015-10-23 2017-05-08 삼성디스플레이 주식회사 Organic light emitting device
KR101614739B1 (en) * 2015-12-01 2016-04-22 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110483533A (en) * 2019-07-08 2019-11-22 宁波卢米蓝新材料有限公司 A kind of compound and its preparation method and application

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