CN108586188A - * derivative, material and organic electroluminescence device comprising the * derivatives - Google Patents

* derivative, material and organic electroluminescence device comprising the * derivatives Download PDF

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Publication number
CN108586188A
CN108586188A CN201810556339.8A CN201810556339A CN108586188A CN 108586188 A CN108586188 A CN 108586188A CN 201810556339 A CN201810556339 A CN 201810556339A CN 108586188 A CN108586188 A CN 108586188A
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aryl
substituted
bases
unsubstituted
derivative
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CN108586188B (en
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曹建华
王士波
张建川
董梁
隋岩
唐永顺
华瑞茂
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Abstract

The invention discloses one kindDerivative includes to be somebody's turn to doThe material and organic electroluminescence device of derivative.It is describedThe structural formula of derivative is as shown in following formula I：Shown in Formulas I provided by the inventionDerivative has dark blue fluorescence property, overcomes the aggregation fluorescent quenching effect of fluorescent material, has higher glass transition temperature, high thermal stability and excellent luminescent properties.The features such as its synthesis technology is simple, and the method for purification is simply suitable for large-scale production, and luminescent properties, the thermal stability etc. of product can be adjusted by connecting different groups, it is the ideal chose as organic electroluminescence device light emitting layer material.The present invention uses the OLED device of above-mentioned fluorescent material, and the fluorescence efficiency height of luminescent layer, stability are good, and luminous efficiency and service life to make device are attained by practical requirement.

Description

* derivative, material and organic electroluminescence device comprising the * derivatives
Technical field
The present invention relates to technical field of organic electroluminescence.More particularly, toDerivative includes to be somebody's turn to doDerivative Material and organic electroluminescence device.
Background technology
Organic electroluminescent (abbreviation OLED) and relevant research are found that early in pope in 1963 et al. and organise first Close the electro optical phenomenon of object monocrystalline anthracene.One kind has been made with the method for vapor deposition 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 Degree is high, visual angle is wide, fast response time, driving voltage is low, small power consumption, bright in luster, contrast is high, technical process is simple, temperature Characteristic is good, the advantages that soft display can be achieved, and can be widely applied to flat-panel monitor and area source, therefore obtained widely grinding Study carefully, develop and uses.
By development in twenties years, organic light emission (EL) material realized red, blue, green emitting comprehensively, application Field also extends to the fields such as macromolecule and metal complex from small molecule.Recent years organic electroluminescent display technology oneself Tend to be ripe, some products have been enter into market, but in industrialization time-histories, and still there are many problems demands to solve, and is especially used for The various organic materials of making devices, carrier injection, transmission performance, material electroluminescence performance, service life, excitation purity, Matching etc. between a variety of materials and between each electrode, it is also unresolved that still there are many problems.Especially luminescent device is shining Practical requirement is also not achieved in efficiency and service life, this limits greatly the development of OLED technology.
And utilize the metal complex phosphor material of triplet emission that there is high luminous efficiency, green light and red light material Have reached requirement, but the special Electronic Structure Characteristics of metal complex, cause its blue light material to be unable to reach use It is required that.On the one hand, blue light is one of three primary colours；On the other hand, blue light material passes through energy transfer mode frequently as fertile material Obtain green light or feux rouges.However, due to the broad-band gap of itself, the performance of blue light/dark blue smooth OLEDs is often inferior to green light or red Light OLEDs.Currently, reaching the efficient dark blue of the blu-ray standard (CIE coordinates are (0.15,0.06)) of European Broadcasting Union (EBU) Luminescent material is still seldom.
So far, reported that these material structures can substantially be classified as in the literature there are many blue light material The classes such as anthracene derivative, talan aromatic derivant, pyrene derivatives, fluorenes and spiro fluorene, and wherein anthracene derivative is application In first ancestor's material of organic electroluminescent component, such as 9,10- diphenylanthrancenes (DPA) and 9,10- bis- (2- naphthalenes) anthracene (ADN), although Have many advantages, such as that fluorescence quantum efficiency height and stability are good, but its unstable film is to accelerate device decline, cause device Service life bad one of the major reasons.
Therefore, good the present invention provides a kind of thermal stability and efficientDerivative, and include thisDerivative Material and organic electroluminescence device.
Invention content
First of the present invention is designed to provide one kindDerivative.The present invention'sDerivative is because of its non-planar junction The introducing of structure, different stable groups forms larger conjugated system, molecule aggregation is effectively prevented from, to obtain thermal stability Dark blue luminescent material get well, efficient.
Second object of the present invention is that it includes to be somebody's turn to do to provide a kind ofThe material of derivative.
Third object of the present invention is to provide a kind of organic electroluminescence device
To reach above-mentioned first purpose, the present invention uses following technical proposals：
It is a kind ofDerivative, structural formula is as shown in following formula I：
In the Formulas I：
R1、R2、R3、R4、R5、R6、R7And R8It is each independently selected from hydrogen atom, deuterium hydrogen atom, C1-C20Alkyl, C2-C20Alkene Base, C2-C20Alkynyl, C1-C20Alkoxy, C3-C20Cycloalkyl group, C3-C20Cycloalkenyl group, substituted or unsubstituted C6-C60Virtue Base, substituted or unsubstituted C6-C60Oxygen-containing aryl, substituted or unsubstituted C2-C60Any one in heterocyclic aryl；
R9、R10And R11It is each independently selected from hydrogen atom, deuterium hydrogen atom, substituted or unsubstituted C6-C60Aryl, substitution Or unsubstituted C2-C60Any one in heterocyclic aryl；
R12Selected from substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Oxygen-containing aryl, substitution Or unsubstituted C6-C60Sulfur-bearing aryl, substituted or unsubstituted C6-C60Aryl containing phosphine, substituted or unsubstituted C6-C60Contain Silicon aryl, substituted or unsubstituted C6-C60Boracic aryl, substituted or unsubstituted C2-C60It is any one in heterocyclic aryl Kind.
Preferably, the C2-C60Any one of heterocyclic aryl in the group as shown in Formula Il -1 to Formula II -22：
In -1~II-20 of Formula II,Indicate substitution position；
Z1、Z2And Z3It is each independently selected from hydrogen, deuterium hydrogen, halogen atom, hydroxyl, itrile group, nitro, amino, amidino groups, diazanyl, hydrazone Base, carboxyl or its carboxylate, sulfonic group or its sulfonate, phosphate or its phosphate, C1-C60Alkyl, C2-C60Alkenyl, C2-C60 Alkynyl, C1-C60Alkoxy, C3-C60Cycloalkyl group, C3-C60Cycloalkenyl group, C6-C60Aryl, at least contain there are one-F ,-CN or C1-C10The C of alkyl6-C60Aryl, substituted or unsubstituted C6-C60Oxygen-containing aryl, substituted or unsubstituted C6-C60Sulfur-bearing Aryl, substituted or unsubstituted C6-C60Boracic aryl, substituted or unsubstituted C6-C60Siliceous aryl, substitution or do not take The C in generation6-C60Any one in phosphorous aryl；
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.
Preferably, the C6-C60Aryl is selected from phenyl, naphthalene, xenyl, anthryl, dianthranide base, pyrenyl, aphthacene base, phenanthrene Base, benzo phenanthryl, benzo anthryl, benzo pyrenyl, fluorenyl, it is Spirofluorene-based in any one.
Preferably, the C6-C60Oxygen-containing aryl is selected from dibenzo [b, d] furans -2- bases, dibenzo [b, d] furans -4- Base, benzofuran -2- bases, benzofuran -5- bases, benzofuran -7- bases, 9,9- xanthphos -4- bases, 9,9- dimethyl Any one in xanthene -2- bases, spiral shell [fluorenes -9,9 '-xanthene] -2 '-bases, spiral shell [fluorenes -9,9 '-xanthene] -2- bases.
Preferably, the C6-C60Sulfur-bearing aryl is selected from dibenzo [b, d] thiophene -2- bases, dibenzo [b, d] thiophene -4- Base, 4- benzene sulfoxide groups phenyl, 4- benzene sulfuryls phenyl, benzothiophene -2- bases, benzothiophene -5- bases, benzothiophene -7- bases, 9,9- Dimethyl thioxanthene -4- bases, 9,9- dimethyl thioxanthene -2- bases, spiral shell [fluorenes -9,9 '-thioxanthene] -2 '-bases, spiral shell [fluorenes -9,9 ' - Thioxanthene] any one in -2- bases.
Preferably, the C6-C60Aryl containing phosphine is selected from 4- (two phenenyl phosphinyl) phenyl, 3- (two phenenyl phosphinyl) benzene Any one in base, dibenzo [b] phosphine oxide -5- (4- phenyl) -4- bases.
Preferably, the C6-C60Siliceous aryl is selected from 4- (triphenyl silicon substrate) phenyl, 4- (diphenyl methyl silicon substrate) benzene Any one in base, 3- (triphenyl silicon substrate) phenyl, 3- (diphenyl methyl silicon substrate) phenyl.
Preferably, the C6-C60Boracic aryl is selected from 4- (two (2,4,6- trimethyls) phenyl)-borine phenyl, dibenzo Any one in [b, d] borine -5- phenyl -4- bases, triphenyl boryl.
Preferably, the substituted C6-C60Aryl, substituted C6-C60Oxygen-containing aryl, substituted C2-C60Heterocyclic aryl takes The C in generation6-C60Sulfur-bearing aryl, substituted C6-C60Aryl containing phosphine, substituted C6-C60Siliceous aryl, substituted C6-C60Boracic aryl With substituted C2-C60Substituent group in heterocyclic aryl is each independently selected from hydrogen, deuterium, halogen atom, C1-C20Alkyl, C2-C20Alkene Base, C2-C20Alkynyl, C1-C20Alkoxy, C3-C20Cycloalkyl group and C3-C20It is one or more in cycloalkenyl group.
Preferably, the substituted C6-C60Oxygen-containing aryl, substituted C6-C60Sulfur-bearing aryl, substituted C6-C60Boracic virtue Base, substituted C6-C60Siliceous aryl and substituted C6-C60Substituent group in phosphorous aryl is selected from hydrogen, deuterium, halogen atom or contains 1 It is one or more in the aliphatic group of~8 carbon atoms.
Preferably, the structural formula is Formulas IAny in structural formula formula A-1~A-149 specific as follows of derivative Shown in kind：
To reach above-mentioned second purpose, the present invention also provides a kind of material, the raw material of the material includes one or more It is above-mentionedDerivative.
Preferably, the material is electroluminescent organic material.
Preferably, the electroluminescent organic material is Organic Light Emitting Diode material.
In addition, above-mentionedApplication of the derivative in preparing electroluminescent organic material also belongs to the protection model of the present invention It encloses.
To reach above-mentioned third purpose, the present invention also provides a kind of organic electroluminescence device, the organic electroluminescents The material of device includes above-mentionedIt is one or more in derivative.
Preferably, the organic electroluminescence device is Organic Light Emitting Diode.
Preferably, the material of the organic luminous layer of the organic electroluminescence device includes above-mentionedOne kind in derivative Or it is a variety of.
Preferably, the organic electroluminescence device is concretely such as lower structure：From the bottom to top successively include transparent substrate, Anode layer, hole transmission layer, organic luminous layer, electron transfer layer and cathode layer.
Preferably, the organic electroluminescence device includes transparent substrate, the anode layer on transparent substrate, is set to sun Pole layer on hole transmission layer, the organic luminous layer on hole transmission layer, the electron transfer layer on organic luminous layer, Cathode layer on electron transfer layer.
Preferably, it is additionally provided with hole injection layer between the organic electroluminescence device Anodic layer and hole transmission layer.
Preferably, the material for constituting the transparent substrate is glass or flexible substrate.
Preferably, the material for constituting the anode layer is inorganic material or organic conductive polymer；Wherein, the inorganic material Material is tin indium oxide, zinc oxide, zinc tin oxide, gold, silver or copper；The organic conductive polymer is selected from polythiophene, polyvinyl At least one of benzene sulfonic acid sodium salt and polyaniline.
Preferably, the material for constituting the hole injection layer is TDATA, m-MTDATA or 2-TNATA；Wherein, described The structural formula of TDATA, m-MTDATA, 2-TNATA are as follows：
Preferably, the material for constituting the hole transmission layer is NPB or TPD；Wherein, the structural formula of the NPB isThe structural formula of the TPD is
Preferably, the material for constituting the organic luminous layer is compound, compound and main body shown in Formulas I shown in Formulas I The mixture that the mixture of material composition or the compound shown in Formulas I are formed with dopant material；When the composition organic luminous layer Material when being the mixture of compound and material of main part composition shown in Formulas I, the matter of compound and material of main part shown in the Formulas I Amount is than being 1~10:90；When the mixing that the material for constituting the organic luminous layer is compound shown in Formulas I and dopant material composition When object, the mass ratio of compound and dopant material shown in the Formulas I is 90:1~10.
Preferably, the material of main part be selected from PVK, DPEPO, DPTPO, TBADN, E3, ADN, α, β-ADN, NPA, PNA or Any one in compound shown in APBN：
Preferably, the dopant material be selected from BD01, BD02, BD03, BD04, BD05, BD06, BD07, BD08, BD09, Any one in BD10, BD11, BD12, BD13：
Preferably, the material of the electron transfer layer is constituted in compound shown in Liq, Alq3, Gaq3 and BAlq Any one：
Preferably, constitute the material of the cathode layer in following elements any one or it is arbitrary two kinds composition conjunction The fluoride of golden or following elements：Lithium, magnesium, silver, calcium, strontium, aluminium, indium, copper, Jin Heyin.
Preferably, the thickness of the hole injection layer is 30-50nm, it may be more preferable to be 40nm.
Preferably, the thickness of the hole transmission layer is 5-15nm, it may be more preferable to be 10nm.
Preferably, the thickness of the organic luminous layer is 10-100nm, it may be more preferable to be 40nm.
Preferably, the thickness of the electron transfer layer is 10-30nm, it may be more preferable to be 50nm.
Preferably, the thickness of the cathode layer is 90-110nm, it may be more preferable to be 100nm.
In addition, above-mentionedApplication of the derivative as light emitting layer material in preparing organic electroluminescence device, It belongs to the scope of protection of the present invention.
Beneficial effects of the present invention are as follows：
Shown in Formulas I provided by the inventionDerivative has dark blue fluorescence property, overcomes the aggregation fluorescence of fluorescent material Quenching effect has higher glass transition temperature, high thermal stability and excellent luminescent properties.Its synthesis technology is simple, carries Pure method is simply suitable for the features such as large-scale production, and can adjust the luminescent properties of product, heat by connecting different groups Stability etc. is the ideal chose as organic electroluminescence device light emitting layer material.The present invention uses above-mentioned phosphor The OLED device of material, the fluorescence efficiency height of luminescent layer, stability are good, and luminous efficiency and service life to make device are attained by Practical requirement.
Description of the drawings
Specific embodiments of the present invention will be described in further detail below in conjunction with the accompanying drawings.
Fig. 1 shows that compound shown in formula I applies the structure chart in OLED device；Wherein, 1- transparent substrates, 2- sun Pole layer, 3- hole injection layers, 4- hole transmission layers, 5- organic luminous layers, 6- electron transfer layers, 7- cathode layers.
Fig. 2 shows the synthetic route charts of compound shown in formula I.
Specific implementation mode
In order to illustrate more clearly of the present invention, the present invention is done further with reference to preferred embodiments and drawings It is bright.Similar component is indicated with identical reference numeral in attached drawing.It will be appreciated by those skilled in the art that institute is specific below The content of description is illustrative and be not restrictive, and should not be limited the scope of the invention with this.
In the present invention, preparation method is then conventional method unless otherwise specified.Raw material used is equal unless otherwise instructed It can be obtained from disclosed commercial sources.
Compound shown in Formulas I provided by the invention can be prepared according to method shown in Fig. 2.In Fig. 2, intermediate product chemical combination In object Int.-1 structural formulas, R1、R2、R3、R4、R5、R6、R7、R8、R9、R10And R11Definition it is identical as the definition in Formulas I, Ar's Definition and R in Formulas I12Definition it is identical.
The test equipment and method that following embodiments are tested for the property OLED material and device are as follows：
OLED device performance detection condition：
Brightness and chromaticity coordinate：It is tested using spectrum scanner PhotoResearch PR-715；
Current density and bright voltage：It is tested using digital sourcemeter Keithley 2420；
Power efficiency：It is tested using NEWPORT 1931-C.
The preparation of embodiment 1, Formula A-1
The first step, 11- (4- bromophenyls) -3- chlorinePreparation, preparation route is as follows：
The concrete operations flow of preparation：
The raw material SM-0 of 20.0g (0.07mol) is dissolved in 360ml anhydrous methylene chlorides, and ice salt bath is cooled to 0 DEG C, adds The raw material SM-1 for entering 13.5g (46.8mmol), the trifluoromethayl sulfonic acid being slowly added dropwise into 11.2g (74.9mmol) are dissolved in dichloromethane The solution of alkane is stirred to react 1 hour, is warming up to 30 DEG C, is stirred to react 18 hours, be concentrated under reduced pressure it is dry, with silica gel column separating purification, It is concentrated under reduced pressure and does, obtain 13.2g white solids, yield 45%.
The preparation of bromo- 4,4 '-dibromomethylene biphenyl of second step, 2-, preparation route are as follows：
The concrete operations flow of preparation：
The upper step intermediate compound I nt.-1 of 5.0g (11.97mmol) 100ml tetrahydrofurans are dissolved, 5.2g is added The 1- naphthalene boronic acids of (30mmol) are added 8.3g (60mmol) Anhydrous potassium carbonates and 10ml water, add 0.2g (0.89mmol) vinegar Sour palladium and 466.8mg (1.78mmol) triphenyl phosphorus, temperature rising reflux are stirred to react 16 hours, are cooled to room temperature, are concentrated under reduced pressure It is dry, it is extracted with dichloromethane and water, collects organic phase, dried with anhydrous sodium sulfate, filtered, filtrate decompression concentration is dry, uses silica gel Column separating purification is concentrated under reduced pressure and does, obtains 5.8g white solids, yield 87%.
Experimental data：
(1)1HNMR(δ、CDCl3)：9.17(s,1H),8.89(d,1H),8.56(d,2H),8.34(m,3H),7.99(d, 2H), 7.93 (t, 1H), 7.89 (m, 2H), 7.77~7.48 (m, 10H), 7.39~7.36 (m, 2H), 7.18 (s, 4H)；
(2)HRMS：C44H28, standard molecular weight 556.2191, test result 556.2183 [M+]；
The preparation of embodiment 2, Formula A-17
The first step, bis- chloro- 5- of intermediate 2,9- (1- naphthalenes)Preparation, preparation route is as follows：
The concrete operations flow of preparation：
With reference to the preparation method of 1 first step of embodiment, the SM-1 of 1 first step of embodiment is replaced with into SM-4, obtains centre Body Int.-2, white solid, yield 38%.
The preparation of second step, Formula A-17, preparation route are as follows：
The concrete operations flow of preparation：
Phenyl boric acid, the 1.36g (1.2mmol) of upper step intermediate compound I nt.-2,6.9g (56.5mmol) of 10g (23.6mmol) Palladium catalyst Pd (PPh3)4And the sodium carbonate of 10g (94.3mmol), add the toluene of 60ml, the ethyl alcohol of 20ml and The water of 20ml, under nitrogen protection, temperature rising reflux are stirred to react 12 hours, are cooled to room temperature, are extracted with ethyl acetate, organic phase It is dried, is filtered with anhydrous sodium sulfate, filtrate decompression concentration is dry, and with silica gel column separating purification, petroleum ether-ethyl acetate elutes, then It is recrystallized with tetrahydrofuran, obtains 7.0g white solids, yield 58%.
Experimental data：
(1)1HNMR(δ、CDCl3)：9.16 (s, 1H), 9.04 (d, 1H), 8.86 (m, 1H), 8.49~8.34 (m, 5H), 8.18 (s, 1H), 8.15~7.91 (m, 3H), 7.87~7.72 (m, 6H), 7.69~7.36 (m, 8H)；
(2)HRMS：C40H26, standard molecular weight 506.2035, test result 506.2026 [M+]；
The preparation of embodiment 3, Formula A-33
The first step, intermediate 11- ([1,1'- biphenyl] -2- bases) -2- chlorinePreparation, preparation route is as follows：
The concrete operations flow of preparation：
With reference to the preparation method of 1 first step of embodiment, the SM-0 of 1 first step of embodiment is replaced with into SM-5, SM-1 is replaced It is changed to SM-6, obtains intermediate compound I nt.-3, white solid, yield 47%.
The preparation of second step, Formula A-33, preparation route are as follows：
The concrete operations flow of preparation：
With reference to the preparation method of 2 second step of embodiment, the Int.-2 of 2 second step of embodiment is replaced with into Int.-3, by benzene Boric acid replaces with 2- phenyl phenyl boric acids, obtains product A-33, white solid, yield 88%.
Experimental data：
(1)1HNMR(δ、CDCl3)：9.06 (d, 1H), 8.86 (m, 1H), 8.42~8.38 (t, 2H), 8.34 (s, 1H), 7.87~7.78 (m, 6H), 7.70~7.58 (m, 11H), 7.37~7.34 (m, 6H)；
(2)HRMS：C42H28, standard molecular weight 532.2191, test result 532.2178 [M+].
With reference to embodiment 1, the synthetic method of embodiment 2 or embodiment 3, following compounds are prepared, i.e., method and step is the same as real Example 1 or embodiment 2 or embodiment 3 are applied, the difference is that only according to required product difference, use according to actual needs different The SM-1 of 1 first step of reactant alternative embodiment, the SM-2 of 1 second step of alternative embodiment；Or 2 first step of alternative embodiment SM-4, the phenyl boric acid of 2 second step of alternative embodiment；Or the SM-6 of 3 first step of alternative embodiment, 3 second step of alternative embodiment 2- phenyl phenyl boric acids, and the quality dosage of the compound is changed according to mole, the results are shown in Table 1：
The mass spectrometric measurement result of the different compounds of table 1
The preparation of embodiment 4, Formula A-4
Preparation route is as follows：
The concrete operations flow of preparation：
The xylene soluble of intermediate compound I nt.-1 80ml prepared by 1 first step of embodiment of 5.0g (11.97mmol), The 4 of addition 5.9g (30.0mmol), the sodium tert-butoxide of 4 '-dimethyl-diphenylamines and 3.0g (32mmol), under nitrogen protection, The palladium catalyst Pd of 124mg (0.12mmol) is added2(dba)3CHCl3And 90% toluene solution of tri-tert phosphorus of 0.2ml, It being warming up to 120 DEG C to be stirred to react 16 hours, is cooled to room temperature, 50ml water is added, stir 30 minutes, filtering, filter cake is washed with ethyl alcohol, Dry, again with toluene-tetrahydrofuran recrystallization obtains 6.8g yellow solids, yield 82%.
Experimental data：
(1)1HNMR(δ、CDCl3)：8.78 (d, 1H), 8.64 (s, 1H), 8.08 (s, 1H), 7.45~7.41 (m, 3H), 7.39~7.28 (m, 8H), 7.22~7.07 (m, 16H), 2.42 (s, 12H)；
(2)HRMS：C52H42N2, standard molecular weight 694.3348, test result 695.3326 [M+H].
With reference to the synthetic method of embodiment 4, preparation structure formula is the compound of A-5, i.e., method and step is with embodiment 4, no It is only that according to required product difference with place, uses the SM-3 of different reactant alternative embodiments 4 according to actual needs, and The quality dosage of the compound, the experimental data HRMS of compound A-5 are changed according to mole：C60H38N2O2, standard molecular weight 818.2933 test result 819.2778 [M+H].
The preparation of embodiment 5, Formula A-148
The first step, intermediate 2- (8,9- dichloros- 5- bases) -4,6- diphenyl -1,3,5-triazines preparation, preparation route It is as follows：
The concrete operations flow of preparation：
With reference to the preparation method of 1 first step of embodiment, the SM-0 of 1 first step of embodiment is replaced with into SM-7, SM-1 is replaced It is changed to SM-8, obtains intermediate compound I nt.-4, yellow solid, yield 36%.
The preparation of second step, intermediate compound I nt.-5, preparation route are as follows：
The concrete operations flow of preparation：
With reference to the preparation method of 2 second step of embodiment, the Int.-2 of 2 second step of embodiment is replaced with into Int.-4, is obtained Intermediate compound I nt.-5, yellow solid, yield 76%.
The preparation of third step, Formula A-148, preparation route are as follows：
The concrete operations flow of preparation：
The anhydrous ferric chloride of upper step intermediate compound I nt.-5,13.5g (81.7mmol) of 5g (8.1mmol) and 250ml's Dichloromethane, under nitrogen protection, temperature rising reflux are stirred to react 12 hours, are cooled to room temperature, filtering, and filtrate decompression concentration is dry, With silica gel column separating purification, petroleum ether-ethyl acetate elution obtains 4.5g white solids, yield 90%.
Experimental data：
(1)1HNMR(δ、CDCl3)：9.47 (d, 2H), 9.02 (s, 1H), 8.58 (d, 1H), 8.49 (s, 1H), 8.35~ 8.28 (m, 5H), 7.82~7.68 (m, 9H), 7.64~7.49 (m, 8H)；
(2)HRMS：C45H27N3, standard molecular weight 609.2205, test result 610.2184 [M+H].
With reference to the synthetic method of embodiment 5, preparation structure formula is respectively the compound of A-146 and A-147, i.e. method and step It with embodiment 5, the difference is that only according to required product difference, replaced implement using different reactants according to actual needs SM-8 in 5 first step of example, and change according to mole the quality dosage of the compound, the experimental data of compound A-146 HRMS：C38H26, standard molecular weight 482.2035, test result 483.1910 [M+H]；The experimental data of compound A-147 HRMS：C40H24, standard molecular weight 504.1878, test result 505.1722 [M+H].
Embodiment 6 prepares device OLED-1~OLED-4
A kind of organic electroluminescence device, structure is as shown in Figure 1, include transparent substrate 1, on transparent substrate 1 Anode layer 2, the hole transmission layer 4 on hole injection layer 3, is set to hole biography at the hole injection layer 3 on anode layer 2 Organic luminous layer 5 on defeated layer 4, the electron transfer layer 6 on organic luminous layer 5, the cathode layer on electron transfer layer 6 7, preparation includes the following steps：
1) glass substrate for being coated with ITO conductive layer is ultrasonically treated 30 minutes in cleaning agent, is rushed in deionized water It washes, it is 30 minutes ultrasonic in acetone/ethanol in the mixed solvent, it is baked to is completely dried under a clean environment, use ultraviolet rays cleaning Machine irradiates 10 minutes, and low energy cation beam bombarded surface is used in combination.
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 0.1nm/s, film thickness, which is deposited, is 40nm；
3) continue that NPB is deposited on above-mentioned hole injection layer to be hole transmission layer, evaporation rate 0.1nm/s, evaporation film Thickness is 10nm；
4) continue to be deposited material based on 1 gained compound A-1 of the embodiment of the present invention, BD05 conducts on the hole transport layer Dopant material, compound A-1：The mass ratio of BD05 is 90:10, as the organic luminous layer of device, evaporation rate 0.1nm/ The film thickness of s, vapor deposition gained organic luminous layer are 40nm；
5) continue that electron transfer layers of the one layer of Liq as device, evaporation rate 0.1nm/ is deposited on organic luminous layer S, vapor deposition film thickness are 50nm；
6) cathode layer of the magnesium/ag alloy layer as device, wherein magnesium/ag alloy layer is deposited successively on electron transfer layer Evaporation rate be 2.0~3.0nm/s, vapor deposition film thickness be 100nm, magnesium and silver mass ratio be 1：9, it obtains provided by the invention OLED device OLED-1.
According to upper identical step, the compound A-1 in step 4) is replaced with into compound A- made from embodiment 3 17, obtain OLED-2 provided by the invention；
According to upper identical step, the compound A-1 in step 4) is replaced with into compound A- made from embodiment 4 33, obtain OLED-3 provided by the invention；
According to upper identical step, the compound A-1 in step 4) is replaced with into compound α, β-ADN, obtains this hair The OLED-4 of bright offer devices as a contrast；
The performance test results of obtained device OLED-1 to OLED-4 are as shown in table 2.
The performance test results of table 2, OLED-1 to OLED-4
From the foregoing, it will be observed that the device bright voltage that the organic material of invention is prepared into is low, brightness current density exists 10mA/cm2Under the conditions of, the 820Cd/m for the reference device OLED-4 that the brightness of device is more than2, and the T97 service life of device is equal It has been more than reference device.
Embodiment 7 prepares device OLED-5~OLED-8
A kind of organic electroluminescence device, structure include the following steps with embodiment 6, preparation：
1) glass substrate for being coated with ITO conductive layer is ultrasonically treated 30 minutes in cleaning agent, is rushed in deionized water It washes, it is 30 minutes ultrasonic in acetone/ethanol in the mixed solvent, it is baked to is completely dried under a clean environment, use ultraviolet rays cleaning Machine irradiates 10 minutes, and low energy cation beam bombarded surface is used in combination.
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 0.1nm/s, film thickness, which is deposited, is 40nm；
3) continue that NPB is deposited on above-mentioned hole injection layer to be hole transmission layer, evaporation rate 0.1nm/s, evaporation film Thickness is 10nm；
4) continue that 2 gained compound A-4 of the embodiment of the present invention is deposited on the hole transport layer to be dopant material, α, β-ADN As material of main part, α, β-ADN：The mass ratio of compound A-4 is 90:10, as the organic luminous layer of device, evaporation rate is The film thickness of 0.1nm/s, vapor deposition gained organic luminous layer are 40nm；
5) continue that electron transfer layers of the one layer of Liq as device, evaporation rate 0.1nm/ is deposited on organic luminous layer S, vapor deposition film thickness are 50nm；
6) cathode layer of the magnesium/ag alloy layer as device, wherein magnesium/ag alloy layer is deposited successively on electron transfer layer Evaporation rate be 2.0~3.0nm/s, vapor deposition film thickness be 100nm, magnesium and silver mass ratio be 1：9, it obtains provided by the invention OLED device OLED-5.
According to upper identical step, the compound A-4 in step 4) is replaced with into compound A-2, the present invention is obtained and carries The OLED-6 of confession；
According to upper identical step, the compound A-4 in step 4) is replaced with into compound A-107, obtains the present invention The OLED-7 of offer；
According to upper identical step, the compound A-4 in step 4) is replaced with into compound BD01, the present invention is obtained and carries The OLED-8 of confession devices as a contrast；
The performance test results of obtained device OLED-5 to OLED-8 are as shown in table 3.
The performance test results of table 3, OLED-5 to OLED-8
From the foregoing, it will be observed that the device bright voltage that the organic material of invention is prepared into is low, brightness current density exists 10mA/cm2Under the conditions of, the 900Cd/m for the reference device OLED-8 that the brightness of device is more than2, and the T97 service life of device is equal It has been more than reference device.
Obviously, the above embodiment of the present invention be only to clearly illustrate example of the present invention, and not be pair The restriction of embodiments of the present invention may be used also on the basis of the above description for those of ordinary skill in the art To make other variations or changes in different ways, all embodiments can not be exhaustive here, it is every to belong to this hair Row of the obvious changes or variations that bright technical solution is extended out still in protection scope of the present invention.

Claims (10)

1. a kind ofDerivative, which is characterized in that describedThe structural formula of derivative is as shown in following formula I：
In the Formulas I：
R1、R2、R3、R4、R5、R6、R7And R8It is each independently selected from hydrogen atom, deuterium hydrogen atom, C1-C20Alkyl, C2-C20Alkenyl, C2-C20Alkynyl, C1-C20Alkoxy, C3-C20Cycloalkyl group, C3-C20Cycloalkenyl group, substituted or unsubstituted C6-C60Aryl, Substituted or unsubstituted C6-C60Oxygen-containing aryl, substituted or unsubstituted C2-C60Any one in heterocyclic aryl；
R9、R10And R11It is each independently selected from hydrogen atom, deuterium hydrogen atom, substituted or unsubstituted C6-C60Aryl, substitution or Unsubstituted C2-C60Any one in heterocyclic aryl；
R12Selected from substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Oxygen-containing aryl, substitution or not Substituted C6-C60Sulfur-bearing aryl, substituted or unsubstituted C6-C60Aryl containing phosphine, substituted or unsubstituted C6-C60Siliceous virtue Base, substituted or unsubstituted C6-C60Boracic aryl, substituted or unsubstituted C2-C60Any one in heterocyclic aryl.
2. according to claim 1Derivative, which is characterized in that the C2-C60Heterocyclic aryl is selected from such as Formula Il -1 To any one in group shown in Formula II -22：
In -1~II-20 of Formula II,Indicate substitution position；
Z1、Z2And Z3Be each independently selected from hydrogen, deuterium hydrogen, halogen atom, hydroxyl, itrile group, nitro, amino, amidino groups, diazanyl, hydrazone group, Carboxyl or its carboxylate, sulfonic group or its sulfonate, phosphate or its phosphate, C1-C60Alkyl, C2-C60Alkenyl, C2-C60Alkynes Base, C1-C60Alkoxy, C3-C60Cycloalkyl group, C3-C60Cycloalkenyl group, C6-C60Aryl, at least contain there are one-F ,-CN or C1- C10The C of alkyl6-C60Aryl, substituted or unsubstituted C6-C60Oxygen-containing aryl, substituted or unsubstituted C6-C60Sulfur-bearing virtue Base, substituted or unsubstituted C6-C60Boracic aryl, substituted or unsubstituted C6-C60Siliceous aryl, substitution or it is unsubstituted C6-C60Any one in phosphorous aryl；
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.
3. according to claim 1 or 2Derivative, which is characterized in that the C6-C60Aryl is selected from phenyl, naphthalene, connection Phenyl, anthryl, dianthranide base, pyrenyl, aphthacene base, phenanthryl, benzo phenanthryl, benzo anthryl, benzo pyrenyl, fluorenyl, it is Spirofluorene-based in Any one；
The C6-C60Oxygen-containing aryl is selected from dibenzo [b, d] furans -2- bases, dibenzo [b, d] furans -4- bases, benzofuran - 2- bases, benzofuran -5- bases, benzofuran -7- bases, 9,9- xanthphos -4- bases, 9,9- xanthphos -2- bases, Any one in spiral shell [fluorenes -9,9 '-xanthene] -2 '-bases, spiral shell [fluorenes -9,9 '-xanthene] -2- bases；
The C6-C60Sulfur-bearing aryl is selected from dibenzo [b, d] thiophene -2- bases, dibenzo [b, d] thiophene -4- bases, 4- benzene sulfoxide groups Phenyl, 4- benzene sulfuryls phenyl, benzothiophene -2- bases, benzothiophene -5- bases, benzothiophene -7- bases, 9,9- dimethyl thioxanthene - In 4- bases, 9,9- dimethyl thioxanthene -2- bases, spiral shell [fluorenes -9,9 '-thioxanthene] -2 '-bases, spiral shell [fluorenes -9,9 '-thioxanthene] -2- bases Any one；
The C6-C60Aryl containing phosphine is selected from 4- (two phenenyl phosphinyl) phenyl, 3- (two phenenyl phosphinyl) phenyl, dibenzo [b] Any one in phosphine oxide -5- (4- phenyl) -4- bases；
The C6-C60Siliceous aryl is selected from 4- (triphenyl silicon substrate) phenyl, 4- (diphenyl methyl silicon substrate) phenyl, 3- (triphenyls Silicon substrate) phenyl, any one in 3- (diphenyl methyl silicon substrate) phenyl；
The C6-C60Boracic aryl is selected from 4- (two (2,4,6- trimethyls) phenyl)-borine phenyl, dibenzo [b, d] borine -5- Any one in phenyl -4- bases, triphenyl boryl.
4. according to claim 1 or 2Derivative, which is characterized in that the substituted C6-C60Aryl, substituted C6- C60Oxygen-containing aryl, substituted C2-C60Heterocyclic aryl, substituted C6-C60Sulfur-bearing aryl, substituted C6-C60Aryl containing phosphine, substitution C6-C60Siliceous aryl, substituted C6-C60Boracic aryl and substituted C2-C60Substituent group in heterocyclic aryl selects each independently From hydrogen, deuterium, halogen atom, C1-C20Alkyl, C2-C20Alkenyl, C2-C20Alkynyl, C1-C20Alkoxy, C3-C20Cycloalkyl group and C3-C20 It is one or more in cycloalkenyl group.
5. according to claim 1Derivative, which is characterized in that the structural formula is Formulas IThe structure of derivative Shown in any one of formula formula A-1~A-149 specific as follows：
6. a kind of material, which is characterized in that the material includes described in any one of claim 1-5 claimsIt is derivative Object.
7. as described in any one of claim 1-5 claimsDerivative answering in preparing electroluminescent organic material With.
8. a kind of organic electroluminescence device, which is characterized in that described in any one of claim 1-5 claimsSpread out Biology.
9. organic electroluminescence device according to claim 8, which is characterized in that describedDerivative is to constitute the electricity The material of the organic luminous layer of electroluminescence device.
10. as described in any one of claim 1-5 claimsDerivative answering in preparing organic electroluminescence device With.
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