CN105399748B - A series of carbazole derivates - Google Patents

A series of carbazole derivates Download PDF

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CN105399748B
CN105399748B CN201510991707.8A CN201510991707A CN105399748B CN 105399748 B CN105399748 B CN 105399748B CN 201510991707 A CN201510991707 A CN 201510991707A CN 105399748 B CN105399748 B CN 105399748B
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CN105399748A (en
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曹建华
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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Abstract

The invention discloses a series of OLED material of carbazole derivates and preparation method thereof and the application in Organic Light Emitting Diode.The structure of the material is shown in formula I.Material shown in the Formulas I has heat endurance good, and emission peak is narrow, the features such as triplet and high quantum efficiency.Using the material prepare organic electroluminescence device power efficiency it is good, long lifespan, and materials synthesis and the method for purification simply be suitable to large-scale production the features such as, be the ideal chose as organic electroluminescence device luminescent material.The organic electroluminescent LED material as the material of main part or dopant material in luminescent layer or separately as luminescent material or as hole mobile material or electron transport material application also in protection domain.

Description

A series of carbazole derivates
Technical field
The invention belongs to ORGANIC ELECTROLUMINESCENCE DISPLAYS and lighting technical field, it is related to a series of carbazole derivates.
Background technology
The research of organic electroluminescent (abbreviation OLED) and correlation is found that and organised first early in pope in 1963 et al. The electro optical phenomenon of compound monocrystalline anthracene.One kind has been made with the method for evaporation organic molecule in the Kodak in the U.S. in 1987 Amorphous membranous type device, driving voltage is fallen below within 20V.This kind of device is due to ultra-thin, all solidstate, self-luminous, bright Spend height, wide visual angle, fast response time, low driving voltage, small power consumption, bright in luster, contrast is high, technical process is simple, temperature Characteristic is good, the advantages of softness is shown can be achieved, and can be widely applied to flat-panel monitor and area source, therefore obtained widely grinding Study carefully, develop and use.
By the development of twenties years, organic EL Material realized red, blue, green emitting, application field comprehensively The fields such as macromolecule and metal complex are extend to from small molecule.Recent years organic electroluminescent Display Technique oneself tend into It is ripe, illumination or display device are prepared into using traditional vacuum vapour deposition, some products have been enter into market, but stock utilization Low, yield is low, causes production cost to remain high.Belong to the OLED solution process of third-generation technology, be with printing ink-jet equipment The RGB luminescent materials of spray solution state turn into pixel, and tri- kinds of RGB faces upward pixel and can independently manufactured.With traditional vacuum vapour deposition method phase Than this can reduce the waste of organic material, and the expense for investing printing equipment is also lower than vacuum evaporation equipment.With white light OLED phase Than, because not needing colored filter, panel production cost can be forced down, and the upward ray structure of microresonator is used, energy The brightness of high intensity is produced, is also one of the reason for being attracted attention.
Unique advantage such as inkjet printable is considered as the direction of display development of future generation.Phosphorescent light-emitting materials can be same Shi Liyong singlet excitons and triplet excitons, effective approach is provided for the further raising of OLED efficiency.It is demonstrated experimentally that 23.4% can be reached using the OLED of phosphor material external quantum efficiency.And inkjet printing is realized, it is necessary to using can solution system Standby luminescent layer.Generally, it is necessary to which phosphor material is doped into polymer body during the luminescent layer that prepared by making solution In, improving the quality of film, suppressing the quenching between phosphorescence triplet excitons and improving the carrier transport of luminescent layer Energy.But most of polymeric material molecular weight distribution inequality, all it is hole mobile material, causes electronics, hole in luminescent layer In the not perfectly flat weighing apparatus of distribution, reduce luminous efficiency.Therefore how to increase the number of electronics in luminescent layer, and then improve device The problem of efficiency is one critically important.
The content of the invention
It is an object of the invention to provide a series of carbazole derivates.
The carbazole derivates that the present invention is provided, its general structure shown in formula I,
In the Formulas I：
R1Straight chain selected from C1-C18 or the aliphatic group with side chain, substituted or unsubstituted C6-C60Aryl, substitution Or unsubstituted C6-C60Aryloxy group, substitution and unsubstituted C2-C60Any one in heterocyclic aryl；
R2Any one in straight chain selected from C1-C18 or the aliphatic group with side chain, itrile group and fluorine atom, specifically For methyl or the tert-butyl group；
R3Straight chain selected from C1-C18 or the aliphatic group with side chain, substituted or unsubstituted C6-C60Aryl, substitution Or unsubstituted C6-C60Aryloxy group, substituted or unsubstituted C6-C60Arylthio, substituted or unsubstituted C6-C60Fragrant phosphine Base, substituted or unsubstituted C6-C60Fragrant silicon substrate, substituted or unsubstituted C6-C60Fragrant boryl and substituted or unsubstituted Any one in C2-C60 heterocyclic aryls；
The substituted C6-C60Aryl, the C of substitution6-C60Aryloxy group, the C of substitution6-C60Arylthio, the C of substitution6-C60Virtue Phosphino-, the C of substitution6-C60Fragrant silicon substrate, the C of substitution6-C60Fragrant boryl, the C of substitution2-C60In heterocyclic aryl, substituent is selected from first It is any in base, ethyl, the tert-butyl group, methoxyl group, cyano group, phenoxy group, halogen atom or aliphatic group containing 2~8 carbon atoms It is a kind of.
Specifically, the C6-C60Aryl be selected from phenyl, naphthyl, xenyl, anthryl, dianthranide base, to tert-butyl-phenyl, 2, 4- difluorophenyls, 4- (N, N- dimethyl amido) phenyl, 4- (N, N- diphenyl amido) phenyl, 3- (N, N- diphenyl amido) benzene Base, pyrenyl, aphthacene base, phenanthryl, benzo phenanthryl, benzo anthryl, benzo pyrenyl, fluorenyl, in any one；
The C6-C60Aryloxy group be selected from 4- Phenoxyphenyls, dibenzo [b, d] furans -2- bases, dibenzo [b, d] furans - Any one in 4- bases, benzofuran -2- bases, benzofuran -5- bases, benzofuran -7- bases；
The C6-C60Arylthio is selected from dibenzo [b, d] thiophene -2- bases, dibenzo [b, d] thiophene -4- bases, 4- benzene sulfoxides Any one in base phenyl, 4- benzene sulfuryls phenyl, benzothiophene -2- bases, benzothiophene -5- bases, benzothiophene -7- bases；
The C6-C60Fragrant phosphino- is selected from 4- (two phenenyl phosphinyl) phenyl, 3- (two phenenyl phosphinyl) phenyl, dibenzo Any one in [b] phosphine oxide -5- (4- phenyl) -4- bases；
The C6-C60Fragrant silicon substrate is selected from 4- (triphenyl silicon substrate) phenyl, 4- (diphenyl methyl silicon substrate) phenyl, 3- (triphens Base silicon substrate) phenyl, any one in 3- (diphenyl methyl silicon substrate) phenyl；
The C6-C60Fragrant boryl be selected from 4- (two (2,4,6- trimethyls) phenyl)-borine phenyl, dibenzo [b, d] borine- Any one in 5- phenyl -4- bases, triphenyl boryl；
The C2-C60Any one in the group as shown in Formula Il -1 to Formula II -15 of heterocyclic aryl：
In the Formula II -1~II-15, Z1、Z2、Z3Independent is selected from hydrogen, deuterium hydrogen, halogen atom, hydroxyl, itrile group, nitro, ammonia Base, amidino groups, diazanyl, hydrazone group, carboxyl or its carboxylate, sulfonic group or its sulfonate, phosphate or its phosphate, C1-C60Alkyl, C2-C60Alkenyl, C2-C60Alkynyl, C1-C60Alkoxy, C3-C60Cycloalkyl group, C3-C60Cycloalkenyl group, C6-C60Aryl, at least contain There are-F ,-a CN or C1-C10The C of alkyl6-C60Aryl, substituted or unsubstituted C6-C60Aryloxy group, substitution or it is unsubstituted C6-C60Aromatic sulfide base and substituted or unsubstituted C2-C60Any one in heterocyclic aryl；
The substituted C6-C60Aryloxy group, the C of substitution6-C60Aromatic sulfide base and the C of substitution2-C60In heterocyclic aryl, substitution Base is selected from methyl, ethyl, the tert-butyl group, methoxyl group, cyano group, phenoxy group, halogen atom or the aliphatic group containing 2~8 carbon atoms In any one；
x1For 1~4 integer；
x2For 1~3 integer；
x3For 1~2 integer；
x4For 1~6 integer；
x5For 1~5 integer；
T1For oxygen or sulphur atom.
More specifically, R in above-mentioned Formulas I1、R2And R3Definition in, C1-C18 straight chain or with side chain aliphatic group tool Body is selected from C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C2-C6 hydrocarbon Base, C2-C18 alkyl, C3-C14 alkyl, C4-C15 alkyl, C5-C10 alkyl, C6-C8 alkyl, C7-C15 hydrocarbon At least one of base and C8-C15 alkyl；Wherein, the alkyl concretely alkyl, (CH3)2N- bases orBase； Wherein,Represent substitution position；
More specifically, compound shown in the Formulas I is any one of following compound 1 into compound 66：
In addition, shown in the Organic Light Emitting Diode material and the Formulas I of compound shown in the Formulas I provided containing the invention described above Compound shown in application and the Formulas I of the compound in Organic Light Emitting Diode material is prepared is being prepared as emitting layer material Application in organic electroluminescence device and using compound shown in Formulas I as the organic electroluminescence device of luminescent layer, falls within Protection scope of the present invention.Wherein, the Organic Light Emitting Diode material is specially electroluminescent organic material, more specifically glimmering Light launch wavelength is 380-420nm electroluminescent organic material；The organic electroluminescence device is specially organic electroluminescence hair Optical device.The fluorescence emission wavelengths are specially 388,390,410 or 418nm.
Specifically, the organic electroluminescence device is from the bottom to top successively by transparent substrate, anode, hole injection layer, sky Cave transport layer, organic luminous layer, electron transfer layer and cathode layer composition.
Wherein, the material for constituting the transparent substrate is glass or flexible substrate；
The material for constituting the anode layer is inorganic material or organic conductive polymer；Wherein, the inorganic material is oxygen Change indium tin, zinc oxide, zinc tin oxide, gold, silver or copper；The organic conductive polymer is selected from polythiophene, polyvinylbenzenesulfonic acid At least one of sodium and polyaniline；
The material for constituting the hole injection layer is PEDOT：Compound shown in PSS, TDATA, m-MTDATA and 2-TNATA In any one：
The material for constituting the hole transmission layer is NPB, TPD, PF6TPD, xPTPD, QUPD, OTPD and PDNA shownization Any one in compound：
The material for constituting the organic luminous layer is compound and dopant material shown in Formulas I；
The quality of the Formulas I-shown compound is 90 with the mass ratio of the dopant material：1-10；
Wherein, any one of the dopant material in following compound：
The material of the electron transfer layer is constituted in compound shown in Liq, Gaq3, TPBI or Slichem-EL-068 Any one：
Constitute the material of the cathode layer in following elements any one or it is any two kinds composition alloy or under State the fluoride of element：Lithium, magnesium, silver, calcium, strontium, aluminium, indium, copper, Jin Heyin.
Specifically, the thickness of the hole injection layer is 30-50nm；Specially 50nm；
The thickness of the hole transmission layer is 10-15nm；Specially 10nm；
The thickness of the organic luminous layer is 10-100nm；Specially 40nm；
The thickness of the electron transfer layer is 10-50nm；Specially 50nm；
The thickness of the cathode layer is 90-110nm, specially 100nm.
Electroluminescent organic material shown in the Formulas I that the present invention is provided, is soluble in organic solvent, with higher vitrifying temperature Degree, high heat endurance and excellent carrier transport ability.Its synthesis technique is simple, and the method for purification is simply suitable on a large scale The features such as production, and molecular energy level, regulation and control luminescent properties, heat endurance etc. can be adjusted by connecting different groups, it is to make For the ideal chose of organic electroluminescence device material.Using the OLED of material of the present invention, its luminous efficiency is high, stability The good, life-span is longer, so that the luminous efficiency of device and life-span are attained by practical requirement.
Brief description of the drawings
Fig. 1 is the synthetic route of compound shown in Formulas I, and wherein a is synthetic route 1, and b is synthetic route 2, and c is synthesis road Line 3；
Embodiment
The feature and technology contents of the present invention are further elaborated with reference to specific embodiment, but the present invention is not limited In following examples.Please refer to the following detailed descriptions related to the present invention and accompanying drawing, but accompanying drawing only provides reference and explanation, and It is non-to be used for being any limitation as the present invention.The raw material can be obtained from open commercial sources unless otherwise instructed.
Compound shown in the Formulas I that the present invention is provided can be prepared according to method shown in Fig. 1.Intermediate product chemical combination in Fig. 1 In thing structural formula, R1、R2、R3Definition it is identical with the definition in Formulas I.
The tester and method that following embodiments carry out performance test to OLED material and device are as follows：
OLED performance detection condition：
Brightness and chromaticity coordinate：Tested using spectrum scanner PhotoResearch PR-715；
Current density and bright voltage：Tested using digital sourcemeter Keithley 2420；
Power efficiency：Tested using NEWPORT 1931-C.
Abbreviation used is defined as follows in following embodiments：
THF tetrahydrofurans
DMSO dimethyl sulfoxide (DMSO)s
LDA lithium diisopropyl amidos
Et3N triethylamines
Pd(PPh3)4Tetrakis triphenylphosphine palladium
Boc2O di-tert-butyl dicarbonates
LiTMP 2,2,6,6- tetramethyl piperidine -1- lithiums
The preparation (synthetic route 1) of embodiment 1, Formula 1
The first step：The preparation of -4,4 '-dimethyl diphenyl of 2- nitros (Int.-1)
360ml 85% nitric acid and 360ml acetic acid mixed solution is added portionwise in the 4,4 ' of 20g-dimethyl diphenyl S-0 In, temperature control is extracted three times with dichloromethane, had in 40 DEG C of stirring reactions 30 minutes, the frozen water that reaction solution is poured into 2500ml Machine mutually uses anhydrous Na2SO4Dry, filtering, filtrate decompression concentration is dry, with recrystallizing methanol, obtain 23g Int.-1, yellow solid, Yield 92.5%.
Second step：Intermediate compound I nt.-2 preparation
15g upper step intermediate compound I nt.-1 and 100ml dichloro-benzenes mixing, the lower triphenyl phosphorus for adding 86.5g of stirring, heating It is warming up to 180 DEG C to react 24 hours, is cooled to room temperature, is concentrated under reduced pressure dry, 100ml petroleum ether, heating is added into residue To seething with excitement, filter while hot, filter cake is washed with petroleum ether, filtrate decompression concentration is dry, and residue uses silica gel column separating purification again, obtains 11.5g 2,7- Dimethylcarbazole Int.-2, the solid of yellow, yield 89%.
3rd step：Intermediate compound I nt.-3 preparation
Bromobenzene, 4.2g Anhydrous potassium carbonate, 19mg cuprous iodide and the use of 2g upper step intermediate compound I nt.-2,3.2g The toluene mixing that 40ml is dried, vacuum decompression deoxidation 10 minutes under nitrogen protection, adds 13.6mg tetramethylethylenediamine, Temperature rising reflux is reacted 24 hours, is cooled to room temperature, suction filtration, filter cake is washed with ethyl acetate, and 50ml water dilution is added into filtrate, Organic phase is separated, is concentrated under reduced pressure dry, residue silica gel column separating purification is eluted with petroleum ether, obtains 2.3g Int.-3, in vain Color solid, yield 82%.
4th step：Intermediate compound I nt.-4 preparation
2g upper step intermediate compound I nt.-3 50ml acetic acid stirring and dissolving, adds 1.24g Potassiumiodate and 1.62g iodine Change potassium, temperature rising reflux reacts 2 hours, is cooled to room temperature, suction filtration, filter cake is washed with water, the aqueous solution of sodium bisulfite of saturation is washed, water Wash, 3.6g intermediate compound I nt.-4, white solid, yield 93% are obtained after drying.
5th step：Intermediate compound I nt.-5 preparation
3.0g upper step intermediate compound I nt.-4 20ml DMF stirring and dissolving, adds 1.4g acetic acid The catalyst PdCl of potassium, 2.88g connection boric acid pinacol ester and 46mg2(dppf)CH2Cl2, under nitrogen protection, heat temperature raising Stayed overnight to 80 DEG C of stirring reactions, be cooled to room temperature, reaction solution is poured into frozen water, be extracted with ethyl acetate three times, collected organic Phase, and anhydrous sodium sulfate drying is used, suction filtration, filtrate decompression concentration is dry, and residue silica gel column separating purification is obtained in 2.9g Mesosome Int.-5, colorless oil, yield 95%.
6th step：Intermediate compound I nt.-6 preparation
2.5g upper step intermediate compound I nt.-5 is dissolved in 40ml tetrahydrofuran, under nitrogen protection, adds 2.2g neighbour Nitrobromobenzene and the natrium carbonicum calcinatum with 2g, add 40ml water and 55mg catalyst Pd (PPh3)4, it is heated to 65 DEG C of stirring reactions are stayed overnight, and are cooled to room temperature, are extracted with ethyl acetate three times, collect organic phase again with the salt washing three of saturation Secondary, organic phase anhydrous sodium sulfate drying, filtering, filtrate decompression concentration is dry, and residue silica gel column separating purification obtains 2.2g Intermediate compound I nt.-6, yellow solid, yield 89.8%.
7th step：Intermediate compound I nt.-7 preparation
2.0g upper step intermediate compound I nt.-6 and 40ml dichloro-benzenes mixing, the lower triphenyl phosphorus for adding 5.1g of stirring, heating It is warming up to 180 DEG C to react 24 hours, is cooled to room temperature, is concentrated under reduced pressure dry, 100ml petroleum ether, heating is added into residue To seething with excitement, filter while hot, filter cake is washed with petroleum ether, filtrate decompression concentration is dry, and residue uses silica gel column separating purification again, obtains 1.4g intermediate compound I nt.-7, the solid of yellow, yield 80%.
8th step：The preparation of compound 1
The iodobenzene of 1.0g upper step intermediate compound I nt.-7,1.0g, 0.92g Anhydrous potassium carbonate, 42mg cuprous iodide and The dimethylbenzene mixing dried with 40ml, vacuum decompression deoxidation 10 minutes under nitrogen protection, adds 51.6mg tetramethyl second two Amine, temperature rising reflux reacts 24 hours, is cooled to room temperature, suction filtration, filter cake is washed with ethyl acetate, and the water that 50ml is added into filtrate is dilute Release, separate organic phase, be concentrated under reduced pressure dry, residue silica gel column separating purification obtains 0.8g Formula 1, yellow solid, Yield 59.7%.
Experimental data：
(1)1HNMR(δ、CDCl3)：7.900~7.928 (d, 2H), 7.613~7.668 (m, 4H), 7.486~7.522 (m, 4H), 7.456~7.475 (d, 2H), 7.415~7.429 (m, 2H), 7.313~7.362 (m, 2H), 7.263~7.296 (m, 3H), 7.240~7.253 (d, 2H), 7.226~7.232 (d, 2H), 7.191~7.202 (d, 2H), 2.503 (s, 6H)；
(2)ESI-MS：C44H31N3, standard molecular weight 601.25, test result 602.32 [M+H]；
(3) uv-absorption maximum wavelength：282nm；
(4) fluorescence emission wavelengths：388nm.
The preparation (synthetic route 2) of embodiment 2, Formula 12
The first step：Intermediate compound I nt.-1 preparation
This step synthetic operation is with reference to the first step of embodiment 1, and by the 4 of the first step of embodiment 1,4 '-dimethyl diphenyl is replaced For 4,4 '-di-t-butyl biphenyl obtains intermediate compound I nt.-1, the solid of yellow, yield 90%.
Second step：Intermediate compound I nt.-2 preparation
This step synthetic operation is with reference to the second step of embodiment 1, and by 2- nitro -4 of the second step of embodiment 1,4 '-dimethyl joins Benzene replaces with 2- nitro -4, and 4 '-di-t-butyl biphenyl obtains intermediate compound I nt.-2, the solid of yellow, yield 90%.
3rd step：Intermediate compound I nt.-3 preparation
15g upper step intermediate compound I nt.-2 is dissolved in 150ml and dried in the tetrahydrofuran steamed again, under nitrogen protection, in batches 2.5g sodium hydride (60% oil dispersed) is added, stirring reaction 30 minutes, the chlorobenzoyl chloride being slowly added dropwise into 9.8g is dissolved in tetrahydrochysene The solution of furans, stirring reaction adds 50ml saturated sodium-chloride water solutions, is extracted with ethyl acetate three times after 12 hours, collects Organic phase is washed three times with the salt of saturation again, and organic phase anhydrous sodium sulfate drying, filtering, filtrate decompression concentration is dry, remaining Thing silica gel column separating purification, obtains 18.5g intermediate compound I nt.-3, white solid, yield 90%.
4th step：Intermediate compound I nt.-4 preparation
4th step of this step synthetic operation reference embodiment 1, by 2, the 7- dimethyl -9- phenyl clicks of the step of embodiment 1 the 4th Azoles replaces with 2,7- di-t-butyl -9- benzoyl carbazoles, obtains intermediate compound I nt.-4, white solid, yield 89%.
5th step：Intermediate compound I nt.-5 preparation
This step synthetic operation with reference to embodiment 1 the 5th step, by iodo- 2, the 7- dimethyl of 3, the 6- bis- of the step of embodiment 1 the 5th- 9- phenyl carbazoles replace with iodo- 2, the 7- di-t-butyls -9- benzoyl carbazoles of 3,6- bis-, obtain intermediate compound I nt.-5, white Solid, yield 86%.
6th step：Intermediate compound I nt.-6 preparation
10g upper step intermediate compound I nt.-5 is dissolved in 100ml toluene, under nitrogen protection, adds 7.0g adjacent nitro Bromobenzene and the Anhydrous potassium carbonate with 8.7g, add the catalyst Pd (PPh of 50ml water, 20ml ethanol and 0.18g3)4, Heat temperature raising return stirring reaction stays overnight, be cooled to room temperature, be extracted with ethyl acetate three times, collect organic phase be concentrated under reduced pressure it is dry, Residue 50ml tetrahydrofuran stirring and dissolving, the water of the sodium hydroxide and 10ml that add 2g is warming up to 60 DEG C of stirring reactions 4 Hour, it is added dropwise to concentrated hydrochloric acid and is adjusted to acidity, be extracted with ethyl acetate three times, collects organic phase and be concentrated under reduced pressure dry, residue is warm Methanol wash, obtain 6.0g intermediate compound I nt.-6, yellow solid, yield 76%.
7th step：Intermediate compound I nt.-7 preparation
Under nitrogen protection, the dimethylbenzene of 6.0g upper step intermediate compound I nt.-6,80ml, the 4.0g bromo- 9- phenyl clicks of 3- The palladium mixing of azoles, 1.65g sodium tert-butoxide and 26mg, adds 0.1ml 10% tri-tert phosphorus-hexane solution, plus Hot temperature rising reflux stirring reaction is stayed overnight, and is cooled to room temperature, and the water for adding 80ml is stirred 30 minutes, separates organic phase, aqueous phase second Acetoacetic ester is extracted three times, is collected organic phase and is concentrated under reduced pressure dry, residue silica gel column separating purification, obtains 8.2g intermediate Int.-7, yellow solid, yield 93%.
8th step：Intermediate compound I nt.-8 preparation
7th step of this step synthetic operation reference embodiment 1, intermediate compound I nt.-7 and triphenyl phosphorus prepared by upper step is mixed Close, reacted 24 hours in 180 DEG C, obtain intermediate compound I nt.-8, the solid of yellow, yield 82%.
9th step：The preparation of compound 12
8th step of this step synthetic operation reference embodiment 1, intermediate compound I nt.-8 prepared by upper step and iodobenzene reaction, silicon Glue column separating purification, obtains Formula 12, the solid of yellow, yield 62%.
Experimental data：
(1)1HNMR(δ、CDCl3)：8.152~8.185 (m, 1H), 7.982~8.008 (m, 2H), 7.872~7.922 (m, 2H), 7.534~7.585 (m, 4H), 7.428~7.503 (m, 7H), 7.308~7.366 (m, 4H), 7.237~7.287 (m, 4H), 7.112~7.175 (m, 8H), 0.826 (s, 18H)；
(2)ESI-MS：C62H50N4, standard molecular weight 663.39, test result 664.20 [M+H]；
(3) uv-absorption maximum wavelength：245nm；
(4) fluorescence emission wavelengths：390nm.
The preparation (synthetic route 3) of embodiment 3, Formula 28
The first step：Intermediate compound I nt.-6 preparation
Intermediate compound I nt.-5 prepared by the 10g step of embodiment 2 the 5th 80ml tetrahydrofuran dissolves, and adds 7.0g's Adjacent nitro iodobenzene, adds 3.5g sodium carbonate and 0.18g palladium catalyst Pd (PPh3)4, 80ml water is added, is warming up to 60 DEG C of stirring reactions 12 hours, are cooled to room temperature, separate organic phase, aqueous phase is extracted with ethyl acetate, organic phase anhydrous slufuric acid Sodium is dried, filtering, and filtrate decompression concentration is dry, uses silica gel column separating purification, obtains 9.0g intermediate compound I nt.-6, yellow crystal, yield 92%.
Second step：Intermediate compound I nt.-7 preparation
7th step of this step synthetic operation reference embodiment 1, intermediate compound I nt.-6 and triphenyl phosphorus prepared by upper step is mixed Close, reacted 24 hours in 180 DEG C, obtain intermediate compound I nt.-7, the solid of yellow, yield 72%.
3rd step：Intermediate compound I nt.-8 preparation
8th step of this step synthetic operation reference embodiment 1, intermediate compound I nt.-7 prepared by upper step and iodobenzene reaction, silicon Glue column separating purification, obtains intermediate, the solid of yellow, yield 85%.
Obtained intermediate 5g 20ml tetrahydrofuran stirring and dissolving, adds 1.12g sodium hydroxide and 5ml water liter Temperature was added dropwise to concentrated hydrochloric acid and is adjusted to acidity, be extracted with ethyl acetate three times, collect organic phase decompression to 60 DEG C of stirring reactions 4 hours Concentration is dry, and residue is washed with the methanol of heat, obtains 4.0g intermediate compound I nt.-8, yellow solid, yield 96%.
4th step：The preparation of Formula 28
The 4 of intermediate compound I nt.-8 and 0.83g prepared by 4.0g upper step, 4 '-difluorodiphenyl base sulfone mixing, add 80ml DMF, add and add 0.8g potassium tert-butoxide, be warming up to 100 DEG C of stirring reactions 24 hours, be cooled to In room temperature, the frozen water for pouring into 360ml, filtering, filter cake is washed with water, and ethanol is washed, and uses silica gel column separating purification, obtains 3.5g Formulas 28, white solid, yield 75%.
Experimental data：
(1)1HNMR(δ、CDCl3)：7.985~8.027 (m, 2H), 7.925~7.961 (m, 2H), 7.534~7.582 (m, 4H), 7.354~7.432 (m, 5H), 7.297~7.323 (m, 2H), 7.235~7.286 (m, 9H), 0.824 (s, 18H)；
(2)ESI-MS：C100H84N6O2S, standard molecular weight 1432.64, test result 1433.82 [M+H]；
(3) uv-absorption maximum wavelength：306nm；
(4) fluorescence emission wavelengths：418nm.
The preparation (synthetic route 1) of embodiment 4, Formula 65
The first step：Intermediate compound I nt.-3 preparation
This step synthetic operation is with reference to the 3rd step of embodiment 1, intermediate compound I nt.-2 and 1- prepared by the second step of embodiment 2 Bromo- 4- (benzenesulfonyl) benzene reaction, obtains intermediate compound I nt.-3, the solid of yellow, yield 90%.
Second step：Intermediate compound I nt.-4 preparation
4th step of this step synthetic operation reference embodiment 1, by 2, the 7- dimethyl -9- phenyl clicks of the step of embodiment 1 the 4th Azoles replaces with the intermediate compound I nt.-3 of step preparation, obtains intermediate compound I nt.-4, white solid, yield 92%.
3rd step：Intermediate compound I nt.-5 preparation
This step synthetic operation with reference to embodiment 1 the 5th step, by iodo- 2, the 7- dimethyl of 3, the 6- bis- of the step of embodiment 1 the 5th- 9- phenyl carbazoles replace with the intermediate compound I nt.-4 of step preparation, obtain intermediate compound I nt.-5, white solid, yield 88%.
4th step：Intermediate compound I nt.-6 preparation
This step synthetic operation with reference to embodiment 1 the 6th step, by 3, the 6- hypoboric acid pinacols ester of the step of embodiment 1 the 6th- 2,7- dimethyl -9- phenyl carbazoles replace with the intermediate compound I nt.-5 of step preparation, obtain intermediate compound I nt.-6, and yellow is consolidated Body, yield 76%.
5th step：Intermediate compound I nt.-7 preparation
7th step of this step synthetic operation reference embodiment 1, intermediate compound I nt.-6 and triphenyl phosphorus prepared by upper step is mixed Close, reacted 24 hours in 180 DEG C, obtain intermediate compound I nt.-7, the solid of grey, yield 86%.
6th step：The preparation of Formula 65
5.0g upper step intermediate compound I nt.-7 is dissolved in 100ml and dried in the tetrahydrofuran steamed again, under nitrogen protection, in batches 0.65g sodium hydride (60% oil dispersed) is added, the iodomethane into 2.2g, stirring reaction 12 is slowly added dropwise in stirring reaction 2 hours After hour, 50ml 2M diluted hydrochloric acid aqueous solutions are added, are extracted with ethyl acetate three times, collect the saline solution that organic phase uses saturation again Wash three times, organic phase anhydrous sodium sulfate drying, filter, filtrate decompression concentration is dry, and residue silica gel column separating purification is obtained 4.7g Formula 65, white solid, yield 90%.
Experimental data：
(1)1HNMR(δ、CDCl3)：7.921~7.976 (m, 2H), 7.873~7.905 (m, 2H), 7.714~7.752 (m, 2H), 7.571~7.625 (m, 5H), 7.473~7.512 (m, 2H), 7.426~7.460 (m, 2H), 7.373~7.411 (m,2H),7.183(s,2H),3.862(s,6H),0.825(s,18H)；
(2)ESI-MS：C46H43N3O2S, standard molecular weight 701.31, test result 702.32 [M+H]；
(3) uv-absorption maximum wavelength：286nm；
(4) fluorescence emission wavelengths：410nm.
Embodiment 5, prepare device OLED-1~OLED-5
1) glass substrate for being coated with ITO conductive layer is rushed in deionized water ultrasonically treated 30 minutes in cleaning agent Wash, it is ultrasonic 30 minutes in acetone/ethanol in the mixed solvent, it is baked to is completely dried under a clean environment, uses ultraviolet rays cleaning Machine irradiates 10 minutes, and with low energy cation beam bombarded surface.
2) the above-mentioned ito glass substrate handled well is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-4Pa, Compound 2-TNATA is deposited on above-mentioned anode tunic as hole injection layer, evaporation rate is 0.1nm/s, evaporation thickness is 40nm；
3) it is hole transmission layer to continue that NPB is deposited on above-mentioned hole injection layer, and evaporation rate is 0.1nm/s, evaporation film Thickness is 10nm；
4) continue to be deposited on hole transmission layer present invention ownership formula I compound 21 as material of main part and DPVQ is as dopant material, and compound 21 and DPVQ mass ratio are 90:10, it is used as the organic luminous layer of device, evaporation rate For 0.1nm/s, the thickness of evaporation gained organic luminous layer is 40nm；
5) continue to be deposited one layer of Liq and Slichem-EL-068 on organic luminous layer as the electron transfer layer of device, Liq and Slichem-EL-068 mass ratio is 95:5, evaporation rate is 0.1nm/s, and evaporation thickness is 50nm；
6) magnesium/ag alloy layer is deposited successively on electron transfer layer as the cathode layer of device, wherein magnesium/ag alloy layer Evaporation rate be 2.0~3.0nm/s, evaporation thickness be 100nm, magnesium and silver mass ratio be 1：9, obtain what the present invention was provided OLED OLED-1.
According to upper identical step, by step 4) in compound 21 replace with the gained compound 28 of embodiment 3, obtain The OLED-2 that the present invention is provided；
According to upper identical step, by step 4) in compound 21 replace with the gained compound 65 of embodiment 4, obtain The OLED-3 that the present invention is provided；
According to upper identical step, by step 4) in compound 21 replace with the gained compound 1 of embodiment 1, obtain The OLED-4 that the present invention is provided；
According to upper identical step, by step 4) in compound 21 replace with the gained compound 12 of embodiment 2, obtain The OLED-5 that the present invention is provided；
Obtained device OLED-1 to OLED-5 performance test results are as shown in table 1.
Table 1, OLED-1 to OLED-5 performance test results
From the foregoing, it will be observed that the device bright voltage that organic material shown in the Formulas I that the present invention is provided is prepared into is low, brightness is maintained at 500cd/m2Under the conditions of, the 9cd/A that the power efficiency of device exceedes, and be navy blue OLED.
Although with reference to preferred embodiment, the present invention is described, the invention is not limited in above-described embodiment, should Work as understanding, under the guiding of present inventive concept, those skilled in the art can carry out various modifications and improvements, and appended claims are general The scope of the present invention is included.

Claims (17)

1. compound shown in Formulas I,
In the Formulas I：
R1Selected from substituted or unsubstituted C6-C60Any one in aryl；
R2Selected from C1-C18Straight chain or aliphatic group with side chain in any one；
R3Selected from C1-C18Straight chain or aliphatic group with side chain, any one in phenyl；
The substituted C6-C60In aryl, it is former that substituent is selected from methyl, ethyl, the tert-butyl group, methoxyl group, cyano group, phenoxy group, halogen Son and the aliphatic group containing 2~8 carbon atoms in any one.
2. compound according to claim 1, it is characterised in that：The C6-C60Aryl be selected from phenyl, naphthyl, xenyl, Anthryl, dianthranide base, to tert-butyl-phenyl, 2,4 difluorobenzene base, 4- (N, N- dimethyl amido) phenyl, 4- (N, N- diphenylamines Base) phenyl, 3- (N, N- diphenyl amido) phenyl, pyrenyl, aphthacene base, phenanthryl, benzo phenanthryl, benzo anthryl, benzo pyrenyl With any one in fluorenyl.
3. the compound of Formulas I -1, it is characterised in that：The compound of Formulas I -1 for it is following any one：
4. the organic light emission two containing the compound of Formulas I -1 described in compound shown in Formulas I described in claim 1 or 2 or claim 3 Pole pipe material.
5. the compound of Formulas I -1 is preparing organic light emission two described in compound shown in Formulas I described in claim 1 or 2 or claim 3 Application in pole pipe material.
6. the compound of Formulas I -1 described in compound shown in Formulas I described in claim 1 or 2 or claim 3 exists as emitting layer material Prepare the application in organic electroluminescence device.
7. application according to claim 6, it is characterised in that：The organic electroluminescence device is from the bottom to top successively by saturating Bright substrate, anode, hole injection layer, hole transmission layer, organic luminous layer, electron transfer layer and cathode layer composition.
8. application according to claim 7, it is characterised in that：It is glass or flexible base to constitute the material of the transparent substrate Piece；
The material for constituting the anode layer is inorganic material or organic conductive polymer；The material for constituting the hole injection layer is PEDOT：Any one in compound shown in PSS, TDATA, m-MTDATA and 2-TNATA：
The material for constituting the hole transmission layer is compound shown in NPB, TPD, PF6TPD, xPTPD, QUPD, OTPD and PDNA In any one：
Constitute the material of organic luminous layer formula described in compound shown in Formulas I described in claim 1 or 2 or claim 3 I-1 compounds and dopant material；
The quality of compound shown in the Formulas I or the compound of Formulas I -1 is 90 with the mass ratio of the dopant material：1-10；
Wherein, any one of the dopant material in following compound：
Constitute the electron transfer layer material be compound shown in Liq, Gaq3, TPBI or Slichem-EL-068 in it is any It is a kind of：
Constitute the material of the cathode layer in following elements any one or it is any two kinds composition alloy or following members The fluoride of element：Lithium, magnesium, silver, calcium, strontium, aluminium, indium, copper, Jin Heyin.
9. application according to claim 8, it is characterised in that：The inorganic material is tin indium oxide, zinc oxide, tin oxide Zinc, gold, silver or copper；The organic conductive polymer in polythiophene, polyvinylbenzenesulfonic acid sodium and polyaniline at least one Kind.
10. application according to claim 7, it is characterised in that：The thickness of the hole injection layer is 30-50nm；
The thickness of the hole transmission layer is 10-15nm；The thickness of the organic luminous layer is 10-100nm；The electric transmission The thickness of layer is 10-50nm；
The thickness of the cathode layer is 90-110nm.
11. application according to claim 10, it is characterised in that：The thickness of the hole injection layer is 50nm；
The thickness of the hole transmission layer is 10nm；
The thickness of the organic luminous layer is 40nm；
The thickness of the electron transfer layer is 50nm；
The thickness of the cathode layer is 100nm.
12. luminescent layer is used as using the compound of Formulas I -1 described in compound shown in Formulas I described in claim 1 or 2 or claim 3 Organic electroluminescence device.
13. device according to claim 12, it is characterised in that：The organic electroluminescence device from the bottom to top successively by Transparent substrate, anode, hole injection layer, hole transmission layer, organic luminous layer, electron transfer layer and cathode layer composition.
14. device according to claim 13, it is characterised in that：The material for constituting the transparent substrate is glass or flexibility Substrate；
The material for constituting the anode layer is inorganic material or organic conductive polymer；
The material for constituting the hole injection layer is PEDOT：In compound shown in PSS, TDATA, m-MTDATA and 2-TNATA Any one：
The material for constituting the hole transmission layer is compound shown in NPB, TPD, PF6TPD, xPTPD, QUPD, OTPD and PDNA In any one：
Constitute the material of organic luminous layer formula described in compound shown in Formulas I described in claim 1 or 2 or claim 3 I-1 compounds and dopant material；
The quality of compound shown in the Formulas I or the compound of Formulas I -1 is 90 with the mass ratio of the dopant material：1-10；
Wherein, any one of the dopant material in following compound：
Constitute the electron transfer layer material be compound shown in Liq, Gaq3, TPBI or Slichem-EL-068 in it is any It is a kind of：
Constitute the material of the cathode layer in following elements any one or it is any two kinds composition alloy or following members The fluoride of element：Lithium, magnesium, silver, calcium, strontium, aluminium, indium, copper, Jin Heyin.
15. device according to claim 14, it is characterised in that：The inorganic material is tin indium oxide, zinc oxide, oxidation Tin zinc, gold, silver or copper；The organic conductive polymer in polythiophene, polyvinylbenzenesulfonic acid sodium and polyaniline at least It is a kind of.
16. device according to claim 13, it is characterised in that：The thickness of the hole injection layer is 30-50nm；
The thickness of the hole transmission layer is 10-15nm；
The thickness of the organic luminous layer is 10-100nm；
The thickness of the electron transfer layer is 10-50nm；
The thickness of the cathode layer is 90-110nm.
17. device according to claim 16, it is characterised in that：The thickness of the hole injection layer is 50nm；
The thickness of the hole transmission layer is 10nm；
The thickness of the organic luminous layer is 40nm；
The thickness of the electron transfer layer is 50nm；
The thickness of the cathode layer is 100nm.
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