CN106336408A - Naphthothioxanthene derivative and preparation method and application thereof - Google Patents
Naphthothioxanthene derivative and preparation method and application thereof Download PDFInfo
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- CN106336408A CN106336408A CN201610715611.3A CN201610715611A CN106336408A CN 106336408 A CN106336408 A CN 106336408A CN 201610715611 A CN201610715611 A CN 201610715611A CN 106336408 A CN106336408 A CN 106336408A
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- 0 *Nc(c(cc1)c23)ccc2Sc(cc2)c4c3c1ccc4c2N(*)N=C Chemical compound *Nc(c(cc1)c23)ccc2Sc(cc2)c4c3c1ccc4c2N(*)N=C 0.000 description 9
- TWUQPLJHUQWBRV-UHFFFAOYSA-N Brc(cc1)c(ccc2ccc3c4c22)c2c1Sc4ccc3Br Chemical compound Brc(cc1)c(ccc2ccc3c4c22)c2c1Sc4ccc3Br TWUQPLJHUQWBRV-UHFFFAOYSA-N 0.000 description 1
- OWYUPBKWIMPSEV-UHFFFAOYSA-N C=S(c(cc1)c2c3c4c5ccc3ccc2c1Br)(c4ccc5Br)=O Chemical compound C=S(c(cc1)c2c3c4c5ccc3ccc2c1Br)(c4ccc5Br)=O OWYUPBKWIMPSEV-UHFFFAOYSA-N 0.000 description 1
- OZOZSRYDEDSCQB-UHFFFAOYSA-N CS(C1CC=C2N(C[AlH2])N)(c3c4C5=C1C2=CCC5=CC=Cc4c(CN[AlH2])cc3)=C Chemical compound CS(C1CC=C2N(C[AlH2])N)(c3c4C5=C1C2=CCC5=CC=Cc4c(CN[AlH2])cc3)=C OZOZSRYDEDSCQB-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention provides a naphthothioxanthene derivative and a preparation method and application thereof, and belongs to the technical field of organic photoelectric materials. According to the material, a naphthothioxanthene group is used as a center to be connected to two amino compounds or carbazole derivatives so as to form a distorted non-planar structure, which has excellent bipolarity of hole-transport capability and electron-transport capability and makes transport equilibration of hole and electron in a luminescent layer and greatly enhances luminescent efficiency. Thus, the material can be used for preparation of organic electroluminescence devices, especially is used as a luminescent layer host-material in an organic electroluminescence device, and is more excellent than existing common OLED devices. The invention also provides a preparation method of the naphthothioxanthene derivative. The preparation method is simple and suitable for industrial production.
Description
Technical field
The present invention relates to organic photoelectrical material technical field is and in particular to a kind of naphtho- thia anthracene derivant and its preparation side
Method and application.
Background technology
Organic Light Emitting Diode (organic light emitting diode, abbreviation oled) is a kind of with organic material
As the current-driven luminescent device of active material, specifically refer to organic semiconducting materials and luminous organic material in electric field
Under driving, by the technology of carrier injection and composite guide photoluminescence.The research of organic electroluminescent phenomenon starts from 20th century 60
Age.Pope of New York Univ USA in 1963 et al. by the voltage of hundreds of volts by anthracene crystal when observe luminescence phenomenon, but
Because driving voltage is too high too low with luminous efficiency, this technology was not taken seriously at that time.Kodak in 1987
C.w.tang et al. first hole transmission layer is incorporated in organic luminescent device, they adopt vacuum evaporation technology alq3
It is made for a kind of amorphous membranous type device of bilayer organic material structure with tpd plated film, so far, oled just causes common people to pay close attention to
(us4356429).This kind of device has frivolous, high brightness, rich color, low power consumption and other advantages, can be widely used for flat luminous
Element such as flat faced display and area source.This research indicates that organic electroluminescent research enters practical stage.1998
Forrest of Princeton university et al. is found that electrophosphorescence phenomenon so that organic electroluminescence device is studied
Enter new period.
The essential structure of electroluminescent device is simple " sandwich style " device.Electro-conductive glass substrate is revolved
Painting, dip-coating or vacuum thermal evaporation luminous organic material (luminescent layer), are then plated with cathode material, connect power supply and constitute Organic Electricity
Electroluminescence device.In order to improve recombination probability and luminous quantum efficiency in organic electroluminescence device luminescent layer, electronics should be made
Injection with hole reaches balance.Electron transfer layer (etl) or/and hole transmission layer is introduced in organic electroluminescence device
(htl), form multiple structure device, contribute to electronics and the balance of hole injection, improve the performance of device.
The machine luminescent material of common are has: 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 etc..
With developing rapidly of photoelectric communication in recent years and MultiMedia Field, luminous organic material has become modern society's letter
Breath and the core of electronic industry.Therefore, with the high speed development in field, luminous organic material be it is also proposed in performance higher
Requirement.
In view of this, how to find a kind of luminous organic material with more preferable performance, improve the luminous effect of luminescent device
Rate and service life, always this area research worker problem demanding prompt solution.
Content of the invention
In view of this, it is an object of the invention to provide a kind of naphtho- thia anthracene derivant and its preparation method and application, adopt
The organic electroluminescence device luminous efficiency of the naphtho- thia anthracene derivant preparation being provided with the present invention is high, preparation method is simple,
It is the luminous organic material of function admirable.
The invention provides a kind of naphtho- thia anthracene derivant, structural formula is:
Or
Wherein, ar1、ar2The independent aryl selected from substituted or unsubstituted c6～c50, substituted or unsubstituted c10～
The condensed ring of c50, the condensed hetero ring of substituted or unsubstituted c8～c50, the aromatic amine of substituted or unsubstituted c6～c50；
Or described ar1、ar2Form substituted or unsubstituted condensed hetero ring with the nitrogen-atoms being located.
Preferably, described ar1、ar2The independent aryl selected from substituted or unsubstituted c6～c30, substituted or unsubstituted
The condensed ring of c10～c30, the condensed hetero ring of substituted or unsubstituted c8～c30, the aromatic amine of substituted or unsubstituted c6～c30.
Preferably, described ar1、ar2Independent selected from following structure:
Wherein, r1、r2Independent selected from hydrogen, the alkyl of c1～c30, the aryl of c6～c30, the condensed ring of c10～c30, c8～
The condensed hetero ring of c30, five-ring heterocycles or hexa-member heterocycle.
Preferably, described ar1、ar2Form the condensed hetero ring of substituted or unsubstituted c12～c30 with the nitrogen-atoms being located.
Preferably, any one in structure shown in following m1～m38 of described naphtho- thia anthracene derivant:
The present invention also provides a kind of preparation method of naphtho- thia anthracene derivant, comprising:
Under nitrogen protection, by the compound shown in formula a or the compound shown in formula b through coupling reaction obtain formula or
Naphtho- thia anthracene derivant shown in formula；
Wherein, ar1、ar2The independent aryl selected from substituted or unsubstituted c6～c50, substituted or unsubstituted c10～
The condensed ring of c50, the condensed hetero ring of substituted or unsubstituted c8～c50, the aromatic amine of substituted or unsubstituted c6～c50；
Or described ar1、ar2Form substituted or unsubstituted condensed hetero ring with the nitrogen-atoms being located.
The present invention also provides application in organic electroluminescence device for the described naphtho- thia anthracene derivant.
Preferably, described organic electroluminescence device includes anode, negative electrode and organic matter layer, and organic matter layer comprises hole note
Enter layer, hole transmission layer, electronic barrier layer, organic luminous layer, hole blocking layer, electron transfer layer, in electron injecting layer extremely
Few one layer, described luminescent layer includes material of main part and dopant dye；
At least one of which in described organic matter layer contains described naphtho- thia anthracene derivant.
Preferably, the material of main part of described luminescent layer is the naphtho- thia anthracene derivant described in one or more.
Beneficial effects of the present invention:
Present invention firstly provides a kind of naphtho- thia anthracene derivant, this naphtho- thia anthracene derivant has formula or formula institute
Show structure.This material, centered on naphtho- thioxanthene class group, connects two amine compounds or carbazole derivates, forms distortion
Nonplanar structure, has the bipolarity of excellent cavity transmission ability and electron transport ability, makes hole and electricity in luminescent layer
The transmission balance of son, greatly improves luminous efficiency；Therefore, this material can be used for preparing organic electroluminescence device, especially makees
For the luminescent layer material of main part in organic electroluminescence device, better than existing conventional oled device.Above-mentioned device can be used for flat board
The applications such as display, lighting source, mobile phone screen, signal lighties.The present invention also provides a kind of naphtho- thia anthracene derivant
Preparation method, using classical coupling reaction method synthesis, preparation method is simple, suitable industrialized production for this material.
Specific embodiment
For a further understanding of the present invention, with reference to embodiment, the preferred embodiment of the invention is described, but
It should be appreciated that these descriptions are simply to further illustrate the features and advantages of the present invention, rather than to the claims in the present invention
Limit.
Present invention firstly provides a kind of naphtho- thia anthracene derivant, structural formula is:
Or
Wherein, ar1、ar2The independent aryl selected from substituted or unsubstituted c6～c50, substituted or unsubstituted c10～
The condensed ring of c50, the condensed hetero ring of substituted or unsubstituted c8～c50, the aromatic amine of substituted or unsubstituted c6～c50；
Or described ar1、ar2Form substituted or unsubstituted condensed hetero ring with the nitrogen-atoms being located.
According to the present invention, described ar1、ar2It is preferably the independent aryl selected from substituted or unsubstituted c6～c30, replacement
Or the condensed ring of unsubstituted c10～c30, the condensed hetero ring of substituted or unsubstituted c8～c30, substituted or unsubstituted c6～c30
Aromatic amine；More preferably independent selected from following structure:
Wherein, described r1、r2Independent selected from hydrogen, the alkyl of c1～c30, the aryl of c6～c30, the condensed ring of c10～c30,
The condensed hetero ring of c8～c30, five-ring heterocycles or hexa-member heterocycle；More preferably independent selected from hydrogen, the alkyl of c1～c10, c6～c18
Aryl, the condensed ring of c10～c18, the condensed hetero ring of c8～c18, five-ring heterocycles or hexa-member heterocycle；Most preferably independent being selected from
Hydrogen, methyl, ethyl, propyl group, isopropyl, butyl, isobutyl group, the tert-butyl group, phenyl, xenyl, naphthyl, anthryl, carbazyl or pyrrole
Piperidinyl.
According to the present invention, described ar1、ar2Substituted or unsubstituted condensed hetero ring can also be formed with the nitrogen-atoms being located, excellent
Form slection becomes the condensed hetero ring of substituted or unsubstituted c12～c30, more preferably forms carbazole group.
It should be noted that in substituent groupRepresent connecting key, r1And r2Represent that substituent group can be in the virtue that is located
The optional position of fragrant ring.
Specifically, described naphtho- thia anthracene derivant is preferably selected from any one in structure shown in following m1～m38:
The present invention also provides a kind of preparation method of naphtho- thia anthracene derivant, comprising:
Under nitrogen protection, the compound shown in the compound shown in intermediate formula a or intermediate formula b is anti-through being coupled
The naphtho- thia anthracene derivant shown in formula or formula should be obtained；
Described ar1、ar2The selection of group is all same as above, will not be described here.
According to the present invention, described intermediate a prepares according to method as follows:
(1) be there is nitration reaction with nitric acid in the thioxanthone shown in formula a-1, obtain the disubstituted nitro shown in formula a-2
Compound；
(2) by compound shown in formula a-2 and carbon tetrabromide, in the presence of triphenylphosphine, there is corey-fuchs dibromo alkene
Glycosylation reaction, obtains the dibromoalkene compound shown in formula a-3；
(3) under nitrogen protection, by compound shown in formula a-3 and trimethylsilyl acetylene in pdcl2 (pph3)2Exist with cui
Lower generation sonogashira reaction, then carries out being catalyzed de- trimethyl silicon substrate and obtains the double alkine compounds shown in formula a-4；
(4) under nitrogen protection, compound shown in formula a-4 is dissolved in dry toluene, adds ptcl2Occur cyclization anti-
Should, obtain compound shown in formula a-5；
(5) compound shown in formula a-5 is dissolved in ethanol and thf mixed solvent, carries out catalytic hydrogenation in the presence of pd/c
Nitro is reduced into amido, then carries out diazotising-bromination reaction and obtain intermediate formula a.
The present invention has no particular limits to the reaction condition in step in said method (1)～(5), using this area skill
Reaction condition known to art personnel.
According to the present invention, intermediate b prepares according to method as follows:
(1) be there is oxidation reaction in the thioxanthone shown in formula a-1 and 30% hydrogen peroxide, obtain the oxidation shown in formula b-1
Thioxanthone；
(2) be there is nitration reaction in the thioxanthone of the oxidation shown in formula b-1 and nitric acid, obtain shown in formula b-2 double takes
For nitro compound；
(3) by compound shown in formula b-2 and carbon tetrabromide, in the presence of triphenylphosphine, there is corey-fuchs dibromo alkene
Glycosylation reaction, obtains the dibromoalkene compound shown in formula b-3；
(4) under nitrogen protection, by compound shown in formula b-3 and trimethylsilyl acetylene in pdcl2 (pph3)2Exist with cui
Lower generation sonogashira reaction, then carries out being catalyzed de- trimethyl silicon substrate and obtains the double alkine compounds shown in formula b-4；
(5) under nitrogen protection, compound shown in formula b-4 is dissolved in dry toluene, adds ptcl2Occur cyclization anti-
Should, obtain compound shown in formula b-5；
(6) compound shown in formula b-5 is dissolved in ethanol and thf mixed solvent, carries out catalytic hydrogenation in the presence of pd/c
Nitro is reduced into amido, then carries out diazotising-bromination reaction and obtain intermediate formula b.
The present invention has no particular limits to the reaction condition in step in said method (1)～(6), using this area skill
Reaction condition known to art personnel.
According to the present invention, the compound shown in the compound shown in intermediate formula a or intermediate formula b is protected in nitrogen
Under, obtain the naphtho- thia anthracene derivant shown in formula or formula through coupling reaction, the present invention does not have spy to described coupling reaction
Different restriction, using coupling reaction well-known to those skilled in the art, this preparation method is simple, and raw material is easy to get.
The present invention also provides application in organic electroluminescence device for the above-mentioned naphtho- thia anthracene derivant, described Organic Electricity
Electroluminescence device includes anode, negative electrode and organic matter layer, and organic matter layer comprises hole injection layer, hole transmission layer, electronic blocking
At least one of which in layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer；In described organic matter layer at least one
Layer is containing naphtho- thia anthracene derivant described above；Preferably described naphtho- thia anthracene derivant is as preparing organic electroluminescent
The luminescent layer material of main part of device.The device architecture adopting in the present invention is: the indium stannum oxygen being attached on glass or plastic base
(ito) as anode；Hole injection layer material selects 2-tnata；The preferable n of hole transmission layer, n '-diphenyl-n, n '-two
(1- naphthyl) -1,1 '-xenyl -4,4 '-diamidogen (npb)；Vacuum evaporation material of main part and dopant on hole transmission layer
ir(ppy)3(main body with dopant mass ratio be 100:9), as the luminescent layer of device, material of main part selects n, and n '-two carbazole-
1,1 '-xenyl -4,4 '-diamidogen (cbp) or the present invention naphtho- thia anthracene derivant；Electron transfer layer selects alq3(quinoline
Aluminum)；Lif is as electron injecting layer；Metal al is as negative electrode.Described organic electroluminescence device can be used for flat faced display, photograph
The applications such as Mingguang City source, direction board, signal lighties.
Unless otherwise indicated, the present invention to the raw material employed in following examples and is commercial goods or adopts ability
Preparation method known to field technique personnel prepares.
Embodiment 1: the preparation of intermediate a
(1) synthesis of compound a -2: add 150ml fuming nitric aicd in 500ml reaction bulb, be cooled to about 5 with ice-water bath
DEG C, it is dividedly in some parts 21.2g (0.1mol) thioxanthone (a-1 compound) under stirring, controlling reaction temperature is less than 10 DEG C, add
Keep reacting liquid temperature at 5 DEG C after reactant, react about 30min.Reactant is poured in frozen water and is stirred vigorously, sucking filtration.Filter cake
Through washing, it is dried, after recrystallization, obtains a-2 compound, yield 80%.
(2) add 22.6g compound a -2 (0.075mol) in the reaction bulb that the synthesis of compound a -3: 500ml is dried,
50g carbon tetrabromide (0.15mol), reaction system is evacuated-and after nitrogen replaces, add 250ml dry benzene, stir 5min, plus
Enter 78.6g triphenylphosphine (0.3mol).Stirring reaction mixture at 150 DEG C, reacts 48h, after the cooling of question response system, adds
Q. s. methylene chloride dissolves.Crude by column chromatography separates and obtains a-3 compound, yield 62%.
(3) synthesis of compound a -4: under nitrogen protection, add 100ml front three containing 5.7ml silicon in 250ml reaction bulb
The triethylamine solution of ethyl-acetylene (0.04mol), adds 4.6g compound a -3 (0.01mol), 0.7g pdcl2(pph3)2
(0.001mol) with 0.38g cui (0.002mol), reactant mixture is heated to 100 DEG C, reacts 20h at this temperature.Treat
After reaction system cooling, add q. s. methylene chloride dissolving, washed respectively with saturated ammonium chloride solution and water, be dried, crude product
Obtain brown solid, yield 73% through column chromatography for separation.
Above-mentioned brown solid is dissolved in 30ml dichloromethane, is slowly added dropwise 15ml tetrabutyl ammonium fluoride containing 10g three hydration
The dichloromethane solution of thing, adds stirring under rear room temperature, reacts 1h.Reaction solution silica gel funnel concentrates after filtering after removing solvent and obtains
To compound a -4, yield 97%.
(4) synthesis of compound a -5: under nitrogen protection, 2.8g compound a -4 (0.008mol) is dissolved in 50ml dry toluene
In, add 0.1gptcl2.Back flow reaction 6h, activated carbon decolorizing, obtain compound a -5, yield 52%.
(5) synthesis of intermediate a: 1.31g compound a -5 is dissolved in 10ml ethanol and the 1:1 mixed solvent of thf, plus
Enter 1g 10%pd/c, system is replaced as hydrogen, and keep system for ortho-hydrogen pressure by hydrogen balloon, stir under room temperature, reaction
10h, Filtration of catalyst, filtrate is concentrated to give faint yellow solid, yield 97%.
Above-mentioned faint yellow solid is dissolved in 15ml 48% hydrobromic acid, ice-water bath maintains the temperature at less than 5 DEG C, slow
Plus 10ml contains 2.1gnano2(0.03mol) aqueous solution, keeps not higher than 10 DEG C of system temperature, drips off follow-up during Deca
Continue in 5 DEG C of 0.5h stirred below.It is subsequently adding 5gcubr-48%hbr solution, system is heated to 80 DEG C, stir 3h, use dichloromethane
Alkane extracts, and point liquid is dried, and column chromatography for separation obtains intermediate a, yield 76%.Mass spectrum m/z:416.13 (value of calculation: 415.87).
Theoretical elemental content (%) c18h8br2S:c, 51.95；h,1.94；br,38.40；s,7.71；Actual measurement constituent content (%): c,
51.89；h,1.92；br,38.44；s,7.75.The above results confirm that obtaining product is target product.
Embodiment 2: the preparation of intermediate b
(1) synthesis of compound b-1: compound a -1 is dissolved in 500ml acetone and 25ml water, is then slowly added dropwise
30%h2o2(10ml), stirring is revolved after 2.5 hours and is removed acetone, and with the solid of 500ml dichloromethane solution modeling, organic faciess are with satisfying
With Sal washing, aqueous phase is extracted with dichloromethane, merges organic faciess, and anhydrous magnesium sulfate is dried, column chromatography for separation after solution concentration
Obtain compound b-1, yield 69%.
(2) synthesis of compound b-2: this step is essentially identical with the step (1) in embodiment 1, difference is to use
Compound b-1 substitutes a-1 as initiation material, and addition is 24.4g compound b-1 (0.1mol), the compound b-2 obtaining,
Yield 78%；
(3) synthesis of compound b-3: this step is essentially identical with the step (2) in embodiment 1, difference is to use
Compound b-2 substitutes a-2 as raw material, and addition is 26.7g compound b-2 (0.08mol), the compound b-3 obtaining, yield
66%；
(4) preparation of compound b-4: this step is essentially identical with the step (3) in embodiment 1, difference is to use
Compound b-3 substitutes a-3 as raw material, and addition is 4.9g compound b-3 (0.01mol), the compound b-4 obtaining, yield
68%；
(5) synthesis of compound b-5: this step is essentially identical with the step (4) in embodiment 1, difference is to use
Compound b-4 substitutes a-4 as raw material, and addition is 3.0g compound b-4 (0.008mol), the compound b-5 obtaining, yield
50%；
(6) preparation of intermediate b: this step is essentially identical with the step (5) in embodiment 1, and difference is useization
Compound b-5 substitutes a-5 as raw material, and addition is 1.43g compound b-5, the intermediate b obtaining, yield 85%；Mass spectrum m/z:
448.13 (value of calculation: 447.86).Theoretical elemental content (%) c18h8br2o2S:c, 48.24；h,1.80；br,35.66；o,
7.14；s,7.16；Actual measurement constituent content (%): c, 48.24；h,1.78；br,35.64；o,7.16；s,7.18.The above results are demonstrate,proved
The real product that obtains is target product.
Embodiment 3: the synthesis of compound m1:
Under nitrogen protection, the intermediate a (12.4g, 0.03mol) that embodiment 1 prepared, carbazole (11.0g,
0.065mol) and sodium tert-butoxide (12.7g, 0.130mol) is added in 600ml dry toluene, two are added under stirring (sub-
Benzylacetone) palladium (0.86g, 1.5mmol) and tri-butyl phosphine (3g 10% solution, 1.5mmol), by above-mentioned reactant liquor in magnetic
The lower 90 DEG C of oil baths of power stirring flow back 6h, cooling, then through after appropriate water washing 2-3 time, reactant liquor is carried out a point liquid, gained is had
The anhydrous mgso of machine phase4After drying, rotary evaporation removes organic solvent and obtains crude product.Compound is obtained after crude product recrystallization
m1.Mass spectrum m/z:588.72 (value of calculation: 588.17).Theoretical elemental content (%) c42h24n2S:c, 85.69；h,4.11；n,
4.76；s,5.45；Actual measurement constituent content (%): c, 85.71；h,4.09；n,4.78；s,5.42.The above results confirm to obtain produces
Thing is target product.
Embodiment 4: the synthesis of compound m2:
Implementation process, with embodiment 3, except for the difference that changes intermediate a into intermediate b (13.4g, 0.03mol), is changed
Compound m2.Mass spectrum m/z:620.72 (value of calculation: 620.16).Theoretical elemental content (%) c42h24n2o2S:c, 81.27；h,
3.90；n,4.51；o,5.16；s,5.17；Actual measurement constituent content (%): c, 81.29；h,3.84；n,4.51；o,5.18；s,
5.19.The above results confirm that obtaining product is target product.
Embodiment 5: the synthesis of compound m3:
Implementation process, with embodiment 3, except for the difference that changes carbazole into equimolar phenyl substituted carbazole, obtains compound
m3.Mass spectrum m/z:740.91 (value of calculation: 740.23).Theoretical elemental content (%) c54h32n2S:c, 87.54；h,4.35；n,
3.78；s,4.33；Actual measurement constituent content (%): c, 87.50；h,4.39；n,3.74；s,4.37.The above results confirm to obtain produces
Thing is target product.
Embodiment 6: the synthesis of compound m4:
Implementation process, with embodiment 4, except for the difference that changes carbazole into equimolar phenyl carbazole, obtains compound m4.Matter
Spectrum m/z:772.91 (value of calculation: 772.22).Theoretical elemental content (%) c54h32n2o2S:c, 83.91；h,4.17；n,3.62；
o,4.14；s,4.15；Actual measurement constituent content (%): c, 83.93；h,4.15；n,3.66；o,4.12；s,4.13.The above results are demonstrate,proved
The real product that obtains is target product.
Embodiment 7: the synthesis of compound m5:
The first step, reaction implementation condition, with embodiment 3, simply changes intermediate a and carbazole into equimolar bromophenyl click
Azoles and aniline, obtain aromatic amine compound.Second step, reaction implementation condition with embodiment 3, simply changes carbazole into equimolar the
The aromatic amine compound that single step reaction generates, obtains compound m5.Mass spectrum m/z:922.53 (value of calculation: 922.31).Theoretical elemental
Content (%) c66h42n4S:c, 85.87；h,4.59；n,6.07；s,3.47；Actual measurement constituent content (%): c, 85.91；h,4.55；
n,6.05；s,3.49.The above results confirm that obtaining product is target product.
Embodiment 8: the synthesis of compound m6:
The first step, reaction implementation condition, with embodiment 4, simply changes intermediate b and carbazole into equimolar bromophenyl click
Azoles and aniline, obtain aromatic amine compound.Second step, reaction implementation condition with embodiment 4, simply changes carbazole into equimolar the
The aromatic amine compound that single step reaction generates, obtains compound m6.Mass spectrum m/z:954.56 (value of calculation: 954.30).Theoretical elemental
Content (%) c66h42n4o2S:c, 82.99；h,4.43；n,5.87；o,3.35；s,3.36；Actual measurement constituent content (%): c,
83.05；h,4.37；n,5.91；o,3.37；s,3.38.The above results confirm that obtaining product is target product.
Embodiment 9: the synthesis of compound m7:
The first step, reaction implementation condition, with embodiment 3, simply changes intermediate a and carbazole into equimolar bromobenzene and benzene
Amine, obtains aromatic amine compound.Second step, reaction implementation condition, with embodiment 3, simply changes carbazole into the equimolar first step anti-
The aromatic amine compound that should generate, obtains compound m7.Mass spectrum m/z:592.28 (value of calculation: 592.20).Theoretical elemental content
(%) c42h28n2S:c, 85.10；h,4.76；n,4.73；s,5.41；Actual measurement constituent content (%): c, 85.12；h,4.74；n,
4.75；s,5.39.The above results confirm that obtaining product is target product.
Embodiment 10: the synthesis of compound m8:
The first step, reaction implementation condition, with embodiment 4, simply changes intermediate b and carbazole into equimolar bromobenzene and benzene
Amine, obtains aromatic amine compound.Second step, reaction implementation condition, with embodiment 4, simply changes carbazole into the equimolar first step anti-
The aromatic amine compound that should generate, obtains compound m8.Mass spectrum m/z:624.75 (value of calculation: 624.19).Theoretical elemental content
(%) c42h28n2o2S:c, 80.74；h,4.52；n,4.48；o,5.12；s,5.13；Actual measurement constituent content (%): c, 80.76；h,
4.50；n,4.44；o,5.14；s,5.15.The above results confirm that obtaining product is target product.
Embodiment 11: the synthesis of compound m9:
The first step, reaction implementation condition with embodiment 3, simply by intermediate a and carbazole change into equimolar to methyl bromide
Benzene and dimethylaniline, obtain aromatic amine compound.Second step, carbazole with embodiment 3, is simply changed into etc. and rubs by reaction implementation condition
The aromatic amine compound that your first step reaction generates, obtains compound m9.Mass spectrum m/z:676.91 (value of calculation: 676.29).Reason
Argument cellulose content (%) c48h40n2S:c, 85.17；h,5.96；n,4.14；s,4.74；Actual measurement constituent content (%): c, 85.13；
h,5.94；n,4.16；s,4.78.The above results confirm that obtaining product is target product.
Embodiment 12: the synthesis of compound m10:
The first step, reaction implementation condition with embodiment 4, simply by intermediate b and carbazole change into equimolar to methyl bromide
Benzene and dimethylaniline, obtain aromatic amine compound.Second step, carbazole with embodiment 4, is simply changed into etc. and rubs by reaction implementation condition
The aromatic amine compound that your first step reaction generates, obtains compound m10.Mass spectrum m/z:708.91 (value of calculation: 708.28).Reason
Argument cellulose content (%) c48h40n2o2S:c, 81.32；h,5.69；n,3.95；o,4.51；s,4.52；Actual measurement constituent content (%):
c,81.36；h,5.65；n,3.91；o,4.53；s,4.54.The above results confirm that obtaining product is target product.
Embodiment 13: the synthesis of compound m11:
The first step, reaction implementation condition with embodiment 3, simply by intermediate a and carbazole change into equimolar 2- bromonaphthalene and
Naphthalidine, obtains aromatic amine compound.Second step, reaction implementation condition, with embodiment 3, simply changes carbazole into equimolar first
The aromatic amine compound that step reaction generates, obtains compound m11.Mass spectrum m/z:792.98 (value of calculation: 792.26).Theoretical elemental contains
Amount (%) c58h36n2S:c, 87.85；h,4.58；n,3.53；s,4.04；Actual measurement constituent content (%): c, 87.83；h,4.60；n,
3.55；s,4.02.The above results confirm that obtaining product is target product.
Embodiment 14: the synthesis of compound m12:
The first step, reaction implementation condition with embodiment 4, simply by intermediate b and carbazole change into equimolar 2- bromonaphthalene and
Naphthalidine, obtains aromatic amine compound.Second step, reaction implementation condition, with embodiment 4, simply changes carbazole into equimolar first
The aromatic amine compound that step reaction generates, obtains compound m12.Mass spectrum m/z:824.98 (value of calculation: 824.25).Theoretical elemental contains
Amount (%) c58h36n2o2S:c, 84.44；h,4.40；n,3.40；o,3.88；s,3.89；Actual measurement constituent content (%): c, 84.50；
h,4.38；n,3.44；o,3.90；s,3.91.The above results confirm that obtaining product is target product.
Embodiment 15: the synthesis of compound m13:
The first step, reaction implementation condition, with embodiment 3, simply changes intermediate a and carbazole into equimolar 4- bromo biphenyl
And naphthalidine, obtain aromatic amine compound.Second step, reaction implementation condition with embodiment 3, simply changes carbazole into equimolar the
The aromatic amine compound that single step reaction generates, obtains compound m13.Mass spectrum m/z:844.29 (value of calculation: 844.26).Theoretical elemental
Content (%) c62h40n2S:c, 88.12；h,4.77；n,3.31；s,3.79；Actual measurement constituent content (%): c, 88.18；h,4.75；
n,3.29；s,3.77.The above results confirm that obtaining product is target product.
Embodiment 16: the synthesis of compound m14:
The first step, reaction implementation condition, with embodiment 4, simply changes intermediate b and carbazole into equimolar 4- bromo biphenyl
And naphthalidine, obtain aromatic amine compound.Second step, reaction implementation condition with embodiment 4, simply changes carbazole into equimolar the
The aromatic amine compound that single step reaction generates, obtains compound m14.Mass spectrum m/z:876.22 (value of calculation: 876.28).Theoretical elemental
Content (%) c62h40n2o2S:c, 84.90；h,4.60；n,3.19；o,3.65；s,3.66；Actual measurement constituent content (%): c,
84.82；h,4.62；n,3.21；o,3.67；s,3.68.The above results confirm that obtaining product is target product.
Embodiment 17: the synthesis of compound m15:
The first step, reaction implementation condition, with embodiment 3, simply changes intermediate a and carbazole into equimolar bromophenyl naphthalene
And aniline, obtain aromatic amine compound.Second step, reaction implementation condition, with embodiment 3, simply changes carbazole into equimolar first
The aromatic amine compound that step reaction generates, obtains compound m15.Mass spectrum m/z:846.38 (value of calculation: 846.31).Theoretical elemental contains
Amount (%) c62h42n2S:c, 87.91；h,5.00；n,3.31；s,3.79；Actual measurement constituent content (%): c, 87.83；h,5.02；n,
3.33；s,3.82.The above results confirm that obtaining product is target product.
Embodiment 18: the synthesis of compound m16:
The first step, reaction implementation condition, with embodiment 4, simply changes intermediate b and carbazole into equimolar bromophenyl naphthalene
And aniline, obtain aromatic amine compound.Second step, reaction implementation condition, with embodiment 4, simply changes carbazole into equimolar first
The aromatic amine compound that step reaction generates, obtains compound m16.Mass spectrum m/z:878.98 (value of calculation: 878.30).Theoretical elemental contains
Amount (%) c62h42n2o2S:c, 84.71；h,4.82；n,3.19；o,3.64；s,3.65；Actual measurement constituent content (%): c, 84.75；
h,4.84；n,3.62；o,3.62；s,3.63.The above results confirm that obtaining product is target product.
Embodiment 19: the synthesis of compound m17:
The first step, reaction implementation condition, with embodiment 3, simply changes intermediate a and carbazole into equimolar 1- bromine (4- benzene
Base) naphthalene and aniline, obtain aromatic amine compound.Second step, reaction implementation condition, with embodiment 3, simply changes carbazole into equimolar
The first step reaction generate aromatic amine compound, obtain compound m17.Mass spectrum m/z:844.29 (value of calculation: 844.26).Theoretical
Constituent content (%) c62h40n2S:c, 88.12；h,4.77；n,3.31；s,3.79；Actual measurement constituent content (%): c, 88.20；h,
4.73；n,3.29；s,3.77.The above results confirm that obtaining product is target product.
Embodiment 20: the synthesis of compound m18:
The first step, reaction implementation condition, with embodiment 4, simply changes intermediate b and carbazole into equimolar 1- bromine (4- benzene
Base) naphthalene and aniline, obtain aromatic amine compound.Second step, reaction implementation condition, with embodiment 4, simply changes carbazole into equimolar
The first step reaction generate aromatic amine compound, obtain compound m18.Mass spectrum m/z:876.28 (value of calculation: 876.36).Theoretical
Constituent content (%) c62h40n2o2S:c, 84.90；h,4.60；n,3.19；o,3.65；s,3.66；Actual measurement constituent content (%): c,
84.82；h,4.62；n,3.22；o,3.67；s,3.68.The above results confirm that obtaining product is target product.
Embodiment 21: the synthesis of compound m19:
The first step, reaction implementation condition with embodiment 3, simply by intermediate a and carbazole change into equimolar 9- bromine anthracene and
Aniline, obtains aromatic amine compound.Second step, reaction implementation condition, with embodiment 3, simply changes carbazole into the equimolar first step
The aromatic amine compound that reaction generates, obtains compound m19.Mass spectrum m/z:792.98 (value of calculation: 792.26).Theoretical elemental content
(%) c58h36n2S:c, 87.85；h,4.58；n,3.53；s,4.04；Actual measurement constituent content (%): c, 87.83；h,4.60；n,
3.55；s,4.02.The above results confirm that obtaining product is target product.
Embodiment 22: the synthesis of compound m20:
The first step, reaction implementation condition with embodiment 4, simply by intermediate b and carbazole change into equimolar 9- bromine anthracene and
Aniline, obtains aromatic amine compound.Second step, reaction implementation condition, with embodiment 4, simply changes carbazole into the equimolar first step
The aromatic amine compound that reaction generates, obtains compound m20.Mass spectrum m/z:824.78 (value of calculation: 824.25).Theoretical elemental content
(%) c58h36n2o2S:c, 84.44；h,4.40；n,3.40；o,3.88；s,3.89；Actual measurement constituent content (%): c, 84.50；h,
4.38；n,3.44；o,3.90；s,3.91.The above results confirm that obtaining product is target product.
Embodiment 23: the synthesis of compound m21:
The first step, reaction implementation condition with embodiment 3, simply by intermediate a and carbazole change into equimolar 9- bromine luxuriant and rich with fragrance and
Aniline, obtains aromatic amine compound.Second step, reaction implementation condition, with embodiment 3, simply changes carbazole into the equimolar first step
The aromatic amine compound that reaction generates, obtains compound m21.Mass spectrum m/z:792.88 (value of calculation: 792.26).Theoretical elemental content
(%) c58h36n2S:c, 87.85；h,4.58；n,3.53；s,4.04；Actual measurement constituent content (%): c, 87.83；h,4.60；n,
3.55；s,4.02.The above results confirm that obtaining product is target product.
Embodiment 24: the synthesis of compound m22:
The first step, reaction implementation condition with embodiment 4, simply by intermediate b and carbazole change into equimolar 9- bromine luxuriant and rich with fragrance and
Aniline, obtain aromatic amine compound.Second step, reaction implementation condition, with embodiment 4, simply changes carbazole into equimolar first
The aromatic amine compound that step reaction generates, obtains compound m22.Mass spectrum m/z:824.66 (value of calculation: 824.25).Theoretical elemental contains
Amount (%) c58h36n2o2S:c, 84.44；h,4.40；n,3.40；o,3.88；s,3.89；Actual measurement constituent content (%): c, 84.50；
h,4.38；n,3.44；o,3.90；s,3.91.The above results confirm that obtaining product is target product.
Embodiment 25: the synthesis of compound m23:
The first step, reaction implementation condition with embodiment 3, simply by intermediate a and carbazole change into equimolar 1- bromine pyrene and
Aniline, obtains aromatic amine compound.Second step, reaction implementation condition, with embodiment 3, simply changes carbazole into the equimolar first step
The aromatic amine compound that reaction generates, obtains compound m23.Mass spectrum m/z:842.86 (value of calculation: 840.26).Theoretical elemental content
(%) c62h36n2S:c, 88.54；h,4.31；n,3.33；s,3.81；Actual measurement constituent content (%): c, 88.39；h,4.52；n,
3.30；s,3.78.The above results confirm that obtaining product is target product.
Embodiment 26: the synthesis of compound m24:
The first step, reaction implementation condition with embodiment 4, simply by intermediate b and carbazole change into equimolar 1- bromine pyrene and
Aniline, obtains aromatic amine compound.Second step, reaction implementation condition, with embodiment 4, simply changes carbazole into the equimolar first step
The aromatic amine compound that reaction generates, obtains compound m24.Mass spectrum m/z:872.98 (value of calculation: 872.25).Theoretical elemental content
(%) c62h36n2o2S:c, 85.30；h,4.16；n,3.21；o,3.66；s,3.67；Actual measurement constituent content (%): c, 85.40；h,
4.12；n,3.19；o,3.64；s,3.65.The above results confirm that obtaining product is target product.
Embodiment 27: the synthesis of compound m25:
The first step, reaction implementation condition, with embodiment 3, simply changes intermediate a and carbazole into equimolar, 2- bromo- 9,
9- dimethyl fluorene and aniline, obtain aromatic amine compound.Second step, carbazole, with embodiment 3, is simply changed into by reaction implementation condition
Mole the first step reaction generate aromatic amine compound, obtain compound m25.Mass spectrum m/z:824.88 (value of calculation: 824.32).
Theoretical elemental content (%) c60h44n2S:c, 87.34；h,5.38；n,3.40；s,3.89；Actual measurement constituent content (%): c,
87.38；h,5.42；n,3.36；s,3.85.The above results confirm that obtaining product is target product.
Embodiment 28: the synthesis of compound m26:
The first step, reaction implementation condition, with embodiment 4, simply changes intermediate b and carbazole into equimolar 2- bromo- 9,9-
Dimethyl fluorene and aniline, obtain aromatic amine compound.Second step, carbazole with embodiment 4, is simply changed into etc. and rubs by reaction implementation condition
The aromatic amine compound that your first step reaction generates, obtains compound m26.Mass spectrum m/z:856.98 (value of calculation: 856.31).Reason
Argument cellulose content (%) c60h44n2o2S:c, 84.08；h,5.17；n,3.27；o,3.73；s,3.74；Actual measurement constituent content (%):
c,84.16；h,5.15；n,3.25；o,3.71；s,3.72.The above results confirm that obtaining product is target product.
Embodiment 29: the synthesis of compound m27:
The first step, reaction implementation condition, with embodiment 3, simply changes intermediate a and carbazole into equimolar 2- bromine fluoranthene
And aniline, obtain aromatic amine compound.Second step, reaction implementation condition, with embodiment 3, simply changes carbazole into equimolar first
The aromatic amine compound that step reaction generates, obtains compound m27.Mass spectrum m/z:840.98 (value of calculation: 840.26).Theoretical elemental contains
Amount (%) c62h36n2S:c, 88.54；h,4.31；n,3.33；s,3.81；Actual measurement constituent content (%): c, 88.60；h,4.29；n,
3.31；s,3.79.The above results confirm that obtaining product is target product.
Embodiment 30: the synthesis of compound m28:
The first step, reaction implementation condition, with embodiment 4, simply changes intermediate b and carbazole into equimolar 2- bromine fluoranthene
And aniline, obtain aromatic amine compound.Second step, reaction implementation condition, with embodiment 4, simply changes carbazole into equimolar first
The aromatic amine compound that step reaction generates, obtains compound m28.Mass spectrum m/z:872.91 (value of calculation: 872.25).Theoretical elemental contains
Amount (%) c62h36n2o2S:c, 85.30；h,4.16；n,3.21；o,3.66；s,3.67；Actual measurement constituent content (%): c, 85.42；
h,4.12；n,3.17；o,3.64；s,3.65.The above results confirm that obtaining product is target product.
Embodiment 31: the synthesis of compound m29:
The first step, reaction implementation condition, with embodiment 3, simply changes intermediate a and carbazole into equimolar 1- bromo- 4- pyrrole
Piperidinyl benzene and aniline, obtain aromatic amine compound.Second step, reaction implementation condition, with embodiment 3, simply changes carbazole into equimolar
The first step reaction generate aromatic amine compound, obtain compound m29.Mass spectrum m/z:746.38 (value of calculation: 746.25).Theoretical
Constituent content (%) c52h34n4S:c, 83.62；h,4.59；n,7.50；s,4.29；Actual measurement constituent content (%): c, 83.74；h,
4.55；n,7.46；s,4.25.The above results confirm that obtaining product is target product.
Embodiment 32: the synthesis of compound m30:
The first step, reaction implementation condition, with embodiment 4, simply changes intermediate b and carbazole into equimolar 1- bromo- 4- pyrrole
Piperidinyl benzene and aniline, obtain aromatic amine compound.Second step, reaction implementation condition, with embodiment 4, simply changes carbazole into equimolar
The first step reaction generate aromatic amine compound, obtain compound m30.Mass spectrum m/z:778.38 (value of calculation: 778.25).Theoretical
Constituent content (%) c52h34n4o2S:c, 80.18；h,4.40；n,7.19；o,4.11；s,4.12；Actual measurement constituent content (%): c,
80.30；h,4.36；n,7.15；o,4.09；s,4.10.The above results confirm that obtaining product is target product.
Embodiment 33: the synthesis of compound m31:
The first step, reaction implementation condition, with embodiment 3, simply changes intermediate a and carbazole into equimolar 8- bromoquinoline
And aniline, obtain aromatic amine compound.Second step, reaction implementation condition, with embodiment 3, simply changes carbazole into equimolar first
The aromatic amine compound that step reaction generates, obtains compound m31.Mass spectrum m/z:694.28 (value of calculation: 694.22).Theoretical elemental contains
Amount (%) c48h30n4S:c, 82.97；h,4.35；n,8.06；s,4.61；Actual measurement constituent content (%): c, 82.85；h,4.39；n,
8.10；s,4.65.The above results confirm that obtaining product is target product.
Embodiment 34: the synthesis of compound m32:
The first step, reaction implementation condition, with embodiment 4, simply changes intermediate b and carbazole into equimolar 8- bromoquinoline
And aniline, obtain aromatic amine compound.Second step, reaction implementation condition, with embodiment 4, simply changes carbazole into equimolar first
The aromatic amine compound that step reaction generates, obtains compound m32.Mass spectrum m/z:726.88 (value of calculation: 726.21).Theoretical elemental contains
Amount (%) c48h30n4o2S:c, 79.32；h,4.16；n,7.71；o,4.40；s,4.41；Actual measurement constituent content (%): c, 79.48；
h,4.12；n,7.67；o,4.36；s,4.37.The above results confirm that obtaining product is target product.
Embodiment 35: the synthesis of compound m33:
The first step, reaction implementation condition, with embodiment 3, simply changes intermediate a and carbazole into equimolar 4- bromine triphen
Amine and aniline, obtain aromatic amine compound.Second step, reaction implementation condition with embodiment 3, simply changes carbazole into equimolar the
The aromatic amine compound that single step reaction generates, obtains compound m33.Mass spectrum m/z:926.38 (value of calculation: 926.34).Theoretical elemental
Content (%) c66h46n4S:c, 85.50；h,5.00；n,6.04；s,3.46；Actual measurement constituent content (%): c, 85.62；h,4.96；
n,6.00；s,3.42.The above results confirm that obtaining product is target product.
Embodiment 36: the synthesis of compound m34:
The first step, reaction implementation condition, with embodiment 4, simply changes intermediate b and carbazole into equimolar 4- bromine triphen
Amine and aniline, obtain aromatic amine compound.Second step, reaction implementation condition with embodiment 4, simply changes carbazole into equimolar the
The aromatic amine compound that single step reaction generates, obtains compound m34.Mass spectrum m/z:958.38 (value of calculation: 958.33).Theoretical elemental
Content (%) c66h46n4o2S:c, 82.65；h,4.83；n,5.84；o,3.34；s,3.34；Actual measurement constituent content (%): c,
82.51；h,4.85；n,5.88；o,3.38；s,3.38.The above results confirm that obtaining product is target product.
Embodiment 37: the synthesis of compound m35:
The first step, reaction implementation condition, with embodiment 3, simply changes intermediate a and carbazole into equimolar 4- bromo- 4'-
Methyl triphenylamine and aniline, obtain aromatic amine compound.Second step, carbazole, with embodiment 3, is simply changed into by reaction implementation condition
Mole the first step reaction generate aromatic amine compound, obtain compound m35.Mass spectrum m/z:954.98 (value of calculation: 954.38).
Theoretical elemental content (%) c68h50n4S:c, 85.50；h,5.28；n,5.87；s,3.36；Actual measurement constituent content (%): c,
85.62；h,5.24；n,5.83；s,3.32.The above results confirm that obtaining product is target product.
Embodiment 38: the synthesis of compound m36:
The first step, reaction implementation condition, with embodiment 4, simply changes intermediate b and carbazole into equimolar 4- bromo- 4'-
Methyl triphenylamine and aniline, obtain aromatic amine compound.Second step, carbazole, with embodiment 4, is simply changed into by reaction implementation condition
Mole the first step reaction generate aromatic amine compound, obtain compound m36.Mass spectrum m/z:986.28 (value of calculation: 986.37).
Theoretical elemental content (%) c68h50n4o2S:c, 82.73；h,5.10；n,5.68；o,3.24；s,3.25；Actual measurement constituent content
(%): c, 82.89；h,5.06；n,5.64；o,3.20；s,3.21.The above results confirm that obtaining product is target product.
Embodiment 39: the synthesis of compound m37:
The first step, reaction implementation condition, with embodiment 3, simply changes intermediate a and carbazole into equimolar 4- bromo- 2'-
Naphthalene aniline and aniline, obtain aromatic amine compound.Second step, reaction implementation condition, with embodiment 3, simply changes carbazole into equimolar
The first step reaction generate aromatic amine compound, obtain compound m37.Mass spectrum m/z:1026.26 (value of calculation: 1026.28).Reason
Argument cellulose content (%) c74h50n4S:c, 86.52；h,4.91；n,5.45；s,3.12；Actual measurement constituent content (%): c, 86.40；
h,4.95；n,5.49；s,3.16.The above results confirm that obtaining product is target product.
Embodiment 40: the synthesis of compound m38:
The first step, reaction implementation condition, with embodiment 4, simply changes intermediate b and carbazole into equimolar 4- bromo- 2'-
Naphthalene aniline and aniline, obtain aromatic amine compound.Second step, reaction implementation condition, with embodiment 4, simply changes carbazole into equimolar
The first step reaction generate aromatic amine compound, obtain compound m38.Mass spectrum m/z:1058.30 (value of calculation: 1058.37).Reason
Argument cellulose content (%) c74h50n4o2S:c, 83.91；h,4.76；n,5.29；o,3.02；s,3.03；Actual measurement constituent content (%):
c,83.75；h,4.80；n,5.33；o,3.06；s,3.07.The above results confirm that obtaining product is target product.
Embodiment 41: the preparation of luminescent device 1
With ito glass as anode, be repeatedly cleaned by ultrasonic ito glass substrate with ethanol, deionized water, after as vacuum tank
Middle drying.It is evacuated to 5 × 10-4pa；On above-mentioned anode substrate, as hole transmission layer, evaporation rate is vacuum evaporation npb
0.1nm/s, evaporation thickness is 40nm.Vacuum evaporation light emitting host material compound m1 on hole transmission layer: dopant ir
(ppy)3(100:9) as device luminescent layer, evaporation rate is 0.005nm/s, and evaporation thickness is 30nm.Vacuum on luminescent layer
Evaporation alq3As electron transfer layer, evaporation rate is 0.01nm/s, and evaporation thickness is 20nm.Vacuum is steamed on the electron transport layer
Plating lif is respectively 1.0nm and 100nm as electron injecting layer, al layer as negative electrode, thickness.Peak position 415nm launched by this device,
Require brightness 1000cd/m2, cut-in voltage 5.0v, maximum current efficiency is 32.7cd/a.
Embodiment 42: the preparation of luminescent device 2
With ito glass as anode, be repeatedly cleaned by ultrasonic ito glass substrate with ethanol, deionized water, after as vacuum tank
Middle drying.It is evacuated to 5 × 10-4pa；On above-mentioned anode substrate, as hole transmission layer, evaporation rate is vacuum evaporation npb
0.1nm/s, evaporation thickness is 40nm.Vacuum evaporation light emitting host material compound m7 on hole transmission layer: dopant ir
(ppy)3(100:9) as device luminescent layer, evaporation rate is 0.005nm/s, and evaporation thickness is 30nm.Vacuum on luminescent layer
Evaporation alq3As electron transfer layer, evaporation rate is 0.01nm/s, and evaporation thickness is 20nm.Vacuum is steamed on the electron transport layer
Plating lif is respectively 1.0nm and 100nm as electron injecting layer, al layer as negative electrode, thickness.Peak position 410nm launched by this device,
Require brightness 1000cd/m2, cut-in voltage 5.2v, maximum current efficiency is 31.6cd/a.
Result above shows, the naphtho- thia anthracene derivant of the present invention is applied in organic electroluminescence device, starts electricity
Force down, current efficiency is high, luminous efficiency is high, is luminous organic material of good performance.
Obviously, the explanation of above example is only intended to help and understands the method for the present invention and its core concept.Should refer to
Go out, for the those of ordinary skill of described technical field, under the premise without departing from the principles of the invention, can also be to this
Bright carry out some improve and modify, these improve and modify also fall in the protection domain of the claims in the present invention.
Claims (9)
1. a kind of naphtho- thia anthracene derivant is it is characterised in that structural formula is:
Wherein, ar1、ar2The independent aryl selected from substituted or unsubstituted c6～c50, substituted or unsubstituted c10～c50
Condensed ring, the condensed hetero ring of substituted or unsubstituted c8～c50, the aromatic amine of substituted or unsubstituted c6～c50；
Or described ar1、ar2Form substituted or unsubstituted condensed hetero ring with the nitrogen-atoms being located.
2. a kind of naphtho- thia anthracene derivant according to claim 1 is it is characterised in that described ar1、ar2Independent is selected from
The aryl of substituted or unsubstituted c6～c30, the condensed ring of substituted or unsubstituted c10～c30, substituted or unsubstituted c8～
The condensed hetero ring of c30, the aromatic amine of substituted or unsubstituted c6～c30.
3. a kind of naphtho- thia anthracene derivant according to claim 1 is it is characterised in that described ar1、ar2Independent is selected from
Following structure:
Wherein, r1、r2Independent selected from hydrogen, the alkyl of c1～c30, the aryl of c6～c30, the condensed ring of c10～c30, c8～c30
Condensed hetero ring, five-ring heterocycles or hexa-member heterocycle.
4. a kind of naphtho- thia anthracene derivant according to claim 1 is it is characterised in that described ar1、ar2With the nitrogen being located
Atom forms the condensed hetero ring of substituted or unsubstituted c12～c30.
5. a kind of naphtho- thia anthracene derivant according to claim 1 is it is characterised in that described naphtho- thia anthracene derivant
Any one in structure shown in following m1～m38:
.
6. the preparation method of the naphtho- thia anthracene derivant described in any one of Claims 1 to 5 is it is characterised in that protect in nitrogen
Under shield, the compound shown in formula a or the compound shown in formula b are obtained the naphtho- sulfur shown in formula or formula through coupling reaction
Miscellaneous anthracene derivant；
Wherein, ar1、ar2The independent aryl selected from substituted or unsubstituted c6～c50, substituted or unsubstituted c10～c50
Condensed ring, the condensed hetero ring of substituted or unsubstituted c8～c50, the aromatic amine of substituted or unsubstituted c6～c50；
Or described ar1、ar2Form substituted or unsubstituted condensed hetero ring with the nitrogen-atoms being located.
7. application in organic electroluminescence device for the naphtho- thia anthracene derivant described in Claims 1 to 5 any one.
8. application in organic electroluminescence device for the naphtho- thia anthracene derivant according to claim 7, described organic
Electroluminescent device includes anode, negative electrode and organic matter layer, and organic matter layer comprises hole injection layer, hole transmission layer, electronics resistance
At least one of which in barrier, organic luminous layer, hole blocking layer, electron transfer layer, electron injecting layer, described luminescent layer includes leading
Body material and dopant dye；
At least one of which in described organic matter layer contains the naphtho- thia anthracene derivant described in any one of Claims 1 to 5.
9. application in organic electroluminescence device for the naphtho- thia anthracene derivant according to claim 8, its feature exists
In the material of main part of described luminescent layer is the naphtho- thia anthracene derivant described in one or more Claims 1 to 5.
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| CN108752317A (en) * | 2018-05-16 | 2018-11-06 | 上海道亦化工科技有限公司 | One kind is containing anthracene derivant and application thereof and luminescent device |
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| US20150255723A1 (en) * | 2014-03-05 | 2015-09-10 | Samsung Display Co., Ltd. | Compound and organic light-emitting device including the same |
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