CN108623526A - Anthracene substitutive derivative and its application - Google Patents

Anthracene substitutive derivative and its application Download PDF

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Publication number
CN108623526A
CN108623526A CN201710153928.7A CN201710153928A CN108623526A CN 108623526 A CN108623526 A CN 108623526A CN 201710153928 A CN201710153928 A CN 201710153928A CN 108623526 A CN108623526 A CN 108623526A
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compound
layer
organic electroluminescence
phenyl
electroluminescence device
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CN108623526B (en
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邢其锋
李之洋
周惠贤
任雪艳
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Beijing Eternal Material Technology Co Ltd
Guan Eternal Material Technology Co Ltd
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Beijing Eternal Material Technology Co Ltd
Guan Eternal Material Technology Co Ltd
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    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
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    • C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
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    • H10K50/14—Carrier transporting layers
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Abstract

The invention discloses a kind of anthracene substitutive derivative and its applications.The present invention relates to one kind such as formula (1) compounds represented, wherein：Ar1Selected from hydrogen atom, phenyl, naphthalene or Ar1It connect to form fused ring aryl via divalent alkyl with phenyl；Ar2Selected from C4~C20Nitrogenous heteroaryl or Ar2Replaced by itrile group.The present invention also protects application of such compound in organic electroluminescence device, especially as electron transport material, the red phosphorescent material of main part in OLED device.

Description

Anthracene substitutive derivative and its application
Technical field
The present invention relates to a kind of novel organic compound more particularly to a kind of compounds for organic electroluminescence device And the application in organic electroluminescence device.
Background technology
Display of organic electroluminescence (hereinafter referred to as OLED) has from main light emission, low-voltage direct-current driving, all solidstate, regards Angular width, light-weight, composition and a series of advantage such as simple for process, compared with liquid crystal display, display of organic electroluminescence Backlight is not needed, visual angle is big, and power is low, and up to 1000 times of liquid crystal display, manufacturing cost is but less than response speed The liquid crystal display of same resolution ratio, therefore, organic electroluminescence device has broad application prospects.
As OLED technology is in the continuous propulsion for illuminating and showing two big fields, people are for influencing OLED device performance The research of efficient organic material focuses more on, the organic electroluminescence device of an excellent in efficiency long lifespan be typically device architecture with The result of the optimization collocation of various organic materials.In most common OLED device structure, the organic of following type is generally included Material：Hole-injecting material, hole mobile material, electron transport material, and assorted luminescent material (dyestuff or doping visitor Body material) and corresponding material of main part etc..
Currently, the electron transport material that tradition uses in electroluminescent device is Alq3, but the electron mobility ratio of Alq3 It is relatively low (about 10-6cm2/Vs).In order to improve the electronic transmission performance of electroluminescence device, researcher has done a large amount of exploration Journal of Sex Research works.LG patents WO03/060956 discloses chemical combination shown in the following formula (a) with benzimidazole ring and anthracene skeleton Object, there are voltage height, service life insufficient defects for the material.In addition, disclosed in patent KR2015024288A a kind of quinazoline and The compound of anthracene skeleton, as shown in following formula (b), such material voltage is equally higher, while luminous efficiency is relatively low.
The leeway however, existing electroluminescent organic material is also improved in terms of luminescent properties, there is an urgent need for open for industry The electroluminescent organic material for sending out new.
Invention content
The technical problem to be solved in the present invention is to provide a kind of novel compound for organic electroluminescence device, with Further increase the luminescent properties of organic electroluminescence device.
Another technical problems to be solved of the invention are to provide the organic electroluminescence that a kind of operating voltage is low, luminous efficiency is high Luminescent device.
To solve the above problems, present invention research and 2,6,9,10- quaternary anthracene compounds are prepared for, research hair It is existing, when structure shown in compound has following formula (1), there is suitable HOMO and lumo energy, carrier transmission performance is more It is good, thus, it applies in OLED device, there is preferably practical performance.
Invention is designed to provide a kind of electron transfer layer can be used for organic electroluminescence device and/or luminescent layer Compound.The compound of the present invention has structure shown in following general formula (1)：
In formula (1), Ar1Selected from hydrogen atom, phenyl, naphthalene or Ar1Connect via divalent alkyl with phenyl to be formed it is thick Cyclophane base；Ar2Selected from by the substituted or unsubstituted C of itrile group4~C20Nitrogenous heteroaryl.
The naphthalene can be 1- naphthalenes, 2- naphthalenes, especially preferably 2- naphthalenes.
The Ar1It can be phenanthryl, pyrenyl, Qu Ji etc. that the fused ring aryl to be formed is connect via divalent alkyl with phenyl.
Ar2The C being selected from4~C20Nitrogenous heteroaryl be preferably five yuan or hexa-atomic of the fragrance containing 1 or 2 nitrogen-atoms The carbon atom number 5~20 that group in race's heterocycle and phenyl ring are formed by connecting by singly bound and/or condensed mode it is nitrogenous Heteroaryl, Ar2Particularly preferably group shown in following formula (2)~(11)：
(* indicates link position).
As a kind of preferred embodiment of compound shown in general formula (1), Ar1When selected from phenyl or naphthyl, Ar2Expression (2) institute Show group
As another preferred embodiment of compound shown in general formula (1), Ar1Selected from hydrogen atom, Ar2Selected from formula (3)~(11) Group：
Some specific examples of the compounds of this invention are enumerated below, but these are only example, be not limited effect.
Discovery of the researcher after a large amount of quantum chemical method carries out Structure Selection-experiment-feedback-adjustment structure, anthracene 2,6,9,10 exist simultaneously substituent group, and 2,6 by phenylene bridging strong electron-withdrawing group, can be with modulating compound HOMO and LUMO values to preferably match the energy level of adjacent layer, while keeping coplanar structure to be conducive to the film forming of molecule Property, have both carrier mobility height；On the other hand, active site is protected, to keeping the stability of compound to have product Pole meaning.Group can induce the Cloud Distribution of anthracene skeleton moderately to expand on substituent group shown in formula (2)~(11), make electricity Sub- cloud distribution is wider, carrier mobility is helped to improve, to obtain performance more material.
The compounds of this invention may be used as the electron transport material in organic electroluminescence device, be also used as Organic Electricity The material of main part of luminescent layer in electroluminescence device.
It should be noted that when as electron transport material, compound is preferably Ar shown in general formula (1)1Selected from phenyl or When naphthalene, Ar2Group shown in expression (2), particularly preferably structure shown in A1
When material of main part as luminescent layer, compound shown in general formula (1) is preferably structure shown in formula A5 to A14, more excellent It is selected as structure shown in formula A7 to A14.
The present invention also provides a kind of organic electroluminescence devices, including substrate, and sequentially form on the substrate Anode layer, organic function layer and cathode layer at least containing one layer of luminescent layer, which is characterized in that in the organic function layer extremely Few one layer contains the compounds of this invention individually or as blending constituent.
As a kind of preferred embodiment of organic electroluminescence device of the present invention, organic function layer includes hole injection Layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer, which is characterized in that electron transfer layer includes the present inventionization Close object.
As another preferred embodiment of organic electroluminescence device of the present invention, organic function layer includes hole transport Layer, luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer, the luminescent layer include light emitting host material and shine Dyestuff, which is characterized in that the material of main part of luminescent layer includes the compounds of this invention.Preferred luminescent layer shines for red phosphorescent Layer.
Further, the thickness of organic electroluminescence device of the invention, the preferably described luminescent layer is 5nm to 50nm, more The thickness of preferred luminescent layer is 10nm to 30nm.It is preferred that its electron-transport layer thickness is 30-80nm, more preferably electron-transport Layer thickness is 40-60nm
The organic electroluminescence device of the present invention, the mass ratio of the preferably described luminescent dye and light emitting host material by Regulate and control the evaporation rate of the two in device fabrication process to control, usually controls the evaporation rate ratio of luminescent dye and material of main part It is 1% to 8%, it is furthermore preferred that the evaporation rate ratio of control luminescent dye and material of main part is 3% to 5%.
Compared with prior art, the compound of the present invention has the following advantages that：
(1) the compound of the present invention has good electron transport ability, is used as electron transport material, can be preferably Match with the lumo energy of luminescent layer material of main part, so as to effectively reduce device operating voltages and improve the luminous effect of device Rate extends device lifetime, has very important practical significance in the manufacture of organic electroluminescence device.
(2) this kind of new material in the present invention can be used as electron transport material in efficient OLED device, also act as The material of main part of red phosphorescent luminescent layer.
(3) preparation is simple for the compounds of this invention, and raw material is easy to get, and is suitable for volume production amplification.
Description of the drawings
From the detailed description below in conjunction with the accompanying drawings to the embodiment of the present invention, these and/or other aspects of the invention and Advantage will become clearer and be easier to understand, wherein：
Fig. 1 is the highest occupied molecular orbital (HOMO) of the compounds of this invention A5；
Fig. 2 is the lowest unoccupied molecular orbital (LUMO) of the compounds of this invention A5；
Fig. 3 is the highest occupied molecular orbital HOMO of the compounds of this invention A7；
Fig. 4 is the lowest unoccupied molecular orbital LUMO of the compounds of this invention A7.
Specific implementation mode
In order to make those skilled in the art more fully understand the present invention, with reference to the accompanying drawings and detailed description to this hair It is bright to be described in further detail.
Synthetic example：
The compound for the synthetic method that do not mentioned in the present invention is all the raw produce obtained by commercial sources.Implement Various chemicals such as petroleum ether, ethyl acetate, n-hexane, toluene, tetrahydrofuran, dichloromethane, four chlorinations used in example Bis- (bromomethyl) benzene of carbon, acetone, 1,2-, CuI, o-phthaloyl chloride, phenylhydrazine hydrochloride, trifluoroacetic acid, acetic acid, trans--diamino Hexamethylene, iodobenzene, cesium carbonate, potassium phosphate, ethylenediamine, benzophenone, cyclopentanone, 9-Fluorenone, sodium tert-butoxide, Loprazolam, 1- Bromo- 2- methyl naphthalenes, o-dibromobenzene, butyl lithium, Bromofume, o-dibromobenzene, benzoyl peroxide, 1- (2- bromophenyls) -2- first Base naphthalene, N- bromo-succinimides, methoxyl methyl San Jia Ji phosphonium chlorides, tris(dibenzylideneacetone) dipalladium, four (triphenylphosphines) Palladium, 1,3- pairs of 2-phenyl-phosphine oxide nickel chloride, carbazole, 3,6- Dimethylcarbazoles, 3- (2- naphthalenes) -6- phenyl carbazoles, N- phenyl The basic chemical industries raw materials such as carbazole -3- boric acid, 9- (2- naphthalenes) carbazole -3- boric acid chemical products can be commercially available at home.
The synthesis of 1. compound A1 of synthetic example
Nitrogen protection, intermediate M1 (36.5g, 100mmol) and 1- (4- boric acid phenyl) -2- phenyl -1H- benzimidazoles (2.30eq), potassium carbonate (5eq), Pd2(dba)3(2%eq) toluene 1000mL+ ethyl alcohol 500ml+ water 300ml open stirring, add Heat reacts 12h, reaction solution washing to 100 DEG C of reflux, and organic phase drying crosses silicagel column, concentrates, boiled and washed with petroleum ether, in obtaining Mesosome M2 (31.2g, yield 85.4%).
Under nitrogen protection, to equipped with mechanical agitation, 4- bromo biphenyls are added in the 10L there-necked flasks of low-reading thermometer (2.5eq.), tetrahydrofuran 200ml open stirring, and ice ethyl alcohol cryostat, to -90 DEG C to -80 DEG C, 30min is interior to be added dropwise liquid nitrogen cooling N-BuLi (2.45eq.), -90 DEG C to -80 DEG C of temperature control during dropwise addition are added intermediate M2 (3.62g, 10mmol), finish Naturally it heats up, removes cryostat, continue stirring 8 hours.Aqueous ammonium chloride solution is added, detaches organic phase, dry, toluene is used in concentration Recrystallization, obtains intermediate M3 (4.8g, 92.3%)
Acetic acid 100ml is added into 250ml reaction bulbs for nitrogen protection, opens stirring, heating, and reaction solution is warming up to 60 DEG C Intermediate M3 (5.2g, 10mmol), KI (5eq.), NaHPO2.H2O (8eq.) are added when left and right, flow back (120 DEG C or so) reactions 5 hours.Filtering, with acetic acid, water, ethyl alcohol washes much filtrate.Re crystallization from toluene obtains A1 (4.2g, 87.5%).
The magnetic resonance spectroscopy data of compound A1：
1H NMR(400MHz,Chloroform)δ8.97(s,1H),8.56(s,1H),8.35(s,1H),8.28(s, 2H), 7.98-7.72 (m, 7H), 7.57 (d, J=3.0Hz, 3H), 7.56-7.38 (m, 8H), 7.27 (d, J=12.0Hz, 5H)
The synthesis of 2. compound A2 of synthetic example
Synthesis step is bromo- (2- naphthalenes) benzene of the 4-- that 4- bromo biphenyls are replaced with to equivalent with compound A1, difference, instead After answering, isolated white solid 6.0g, yield 84.5%.
The magnetic resonance spectroscopy data of compound A2：
1H NMR (400MHz, Chloroform) δ 8.97 (s, 3H), 8.45 (d, J=84.0Hz, 5H), 8.35-8.31 (m, 2H), 8.28 (s, 5H), 8.07 (d, J=12.0Hz, 6H), 7.99 (s, 3H), 7.79 (t, J=8.0Hz, 5H), 7.63 (s, 3H), 7.60-7.47 (m, 21H), 7.38 (s, 3H), 7.26 (d, J=12.0Hz, 5H)
The synthesis of 3. compound A-13 of synthetic example
For synthesis step with compound A1, difference is that the 2- bromines that 4- bromo biphenyls are replaced with to equivalent are luxuriant and rich with fragrance, after reaction, Isolated white solid 6.2g, yield 88.3%.
1H NMR(400MHz,Chloroform)δ9.11(s,1H),8.97(s,1H),8.70(s,1H),8.56(s, 1H), 8.43 (s, 1H), 8.35 (s, 1H), 8.28 (s, 2H), 8.15 (s, 1H), 7.91 (d, J=8.0Hz, 2H), 7.84-7.68 (m, 8H), 7.66 (d, J=10.0Hz, 2H), 7.59-7.48 (m, 6H), 7.28 (s, 1H)
The synthesis of 4. compound A4 of synthetic example
With compound A1, difference is to replace with 4- bromo biphenyls into the 2- bromine pyrenes of equivalent synthesis step, after reaction, Isolated white solid 4.6g, yield 75.9%.
1H NMR (400MHz, Chloroform) δ 8.97 (s, 1H), 8.46 (d, J=84.0Hz, 2H), 8.34-8.31 (m, 1H), 8.28 (s, 2H), 8.19 (s, 1H), 8.06 (d, J=16.0Hz, 5H), 7.92 (d, J=1.8Hz, 5H), 7.79 (t, J=8.0Hz, 6H), 7.59-7.47 (m, 6H), 7.28 (s, 1H)
The synthesis of 5. compound A-45 of synthetic example
Synthesis step is with compound A1, and difference is to replace with 4- bromo biphenyls into the bromobenzene of equivalent, by 1- (4- boric acid benzene Base) -2- phenyl -1H- benzimidazoles replace with 2- (4- phenyl boric acids)-pyrazine of equivalent, after reaction, isolated white Solid 5.2g, yield 80.0%.
1H NMR(400MHz,Chloroform)δ8.97(s,1H),8.93–8.86(m,2H),8.86–8.76(m,4H), 8.35 (s, 4H), 7.89 (s, 2H), 7.65 (s, 2H), 7.54 (d, J=12.0Hz, 4H), 7.41 (s, 2H)
The synthesis of 6. compound A6 of synthetic example
The same compound A-45 of synthesis step, difference are to replace with 1- (4- boric acid phenyl) -2- phenyl -1H- benzimidazoles Equivalent
5- (4- phenyl boric acids)-pyrimidine, after reaction, isolated white solid 4.9g, yield 72.4%.
1H NMR(400MHz,Chloroform)δ9.57(s,2H),9.09(s,4H),8.97(s,2H),8.35(s, 2H), 7.65 (s, 4H), 7.54 (d, J=12.0Hz, 7H), 7.41 (s, 1H), 7.25 (s, 8H)
The synthesis of 7. compound A7 of synthetic example
With compound A1, difference is to replace with 1- (4- boric acid phenyl) -2- phenyl -1H- benzimidazoles synthesis step Equivalent
2- (4- phenyl boric acids) -5- cyanopyrimidines, after reaction, isolated white solid 5.2g, yield 78.5%.
1H NMR(400MHz,Chloroform)δ9.29(s,2H),8.97(s,1H),8.35(s,1H),7.96(s, 2H), 7.65 (s, 2H), 7.54 (d, J=12.0Hz, 4H), 7.41 (s, 2H), 7.25 (s, 2H)
The synthesis of 8. compound A-28 of synthetic example
With compound A7, difference is to replace with 1- (4- boric acid phenyl) -2- phenyl -1H- benzimidazoles synthesis step Equivalent
5- (4- phenyl boric acids)-pyrimidine, after reaction, isolated white solid 4.9g, yield 72.4%.
1H NMR(400MHz,Chloroform)δ9.57(s,2H),9.09(s,4H),8.97(s,2H),8.35(s, 2H), 7.65 (s, 4H), 7.54 (d, J=12.0Hz, 7H), 7.41 (s, 1H), 7.25 (s, 8H)
The synthesis of 9. compound A9 of synthetic example
With compound A1, difference is to replace with 1- (4- boric acid phenyl) -2- phenyl -1H- benzimidazoles synthesis step Equivalent
Bis- naphthopyridines of 2- (4- phenyl boric acids) -1,8-, after reaction, isolated white solid 4.8g, yield is 75.3%.1H NMR (400MHz, Chloroform) δ 8.97 (s, 2H), 8.69 (d, J=8.0Hz, 4H), 8.37 (d, J= 10.0Hz, 3H), 8.07 (d, J=10.0Hz, 3H), 7.94 (s, 1H), 7.85 (s, 3H), 7.65 (s, 3H), 7.54 (d, J= 12.0Hz,4H),7.41(s,3H).
The synthesis of 10. compound A10 of synthetic example
With compound A1, difference is to replace with 1- (4- boric acid phenyl) -2- phenyl -1H- benzimidazoles synthesis step Equivalent
7- (4- phenyl boric acids)-quinoline, obtains faint yellow solid 4.7g, yield 73.6%.
1H NMR (400MHz, Chloroform) δ 9.13 (s, 2H), 8.97 (s, 3H), 8.92 (s, 1H), 8.28 (d, J= 10.0Hz, 4H), 8.07 (s, 2H), 7.65 (s, 4H), 7.63-7.44 (m, 9H), 7.40 (d, J=8.0Hz, 3H), 7.25 (s, 8H).
The synthesis of 11. compound A11 of synthetic example
With compound A1, difference is to replace with 1- (4- boric acid phenyl) -2- phenyl -1H- benzimidazoles synthesis step Equivalent
2- (4- phenyl boric acids)-quinoline, obtains faint yellow solid 5.9g, yield 92.4%.
1H NMR (400MHz, Chloroform) δ 8.97 (s, 1H), 8.69 (s, 2H), 8.37 (d, J=16.0Hz, 2H), 8.10(s,2H),8.10(s,1H),8.18–7.79(m,4H),8.18–7.68(m,4H),8.18–7.59(m,4H),8.18– 7.43(m,4H),8.18–7.11(m,5H).
The synthesis of 12. compound A12 of synthetic example
With compound A1, difference is to replace with 1- (4- boric acid phenyl) -2- phenyl -1H- benzimidazoles synthesis step Equivalent
- 2 boric acid of 4,6- diphenyl-pyrimidine obtains faint yellow solid 3.4g, yield 74.5%.
1H NMR (400MHz, Chloroform) δ 8.38 (d, J=12.0Hz, 2H), 8.23 (s, 1H), 7.94 (s, 4H), 7.81(s,1H),7.65(s,2H),7.55(s,6H),7.49(s,2H),7.41(s,2H).
The synthesis of 13. compound A13 of synthetic example
With compound A1, difference is to replace with 1- (4- boric acid phenyl) -2- phenyl -1H- benzimidazoles synthesis step Equivalent
3,5- bis- (2- pyridines)-phenyl boric acids, obtain faint yellow solid 4.8g, yield 74.5%.
1H NMR (400MHz, Chloroform) δ 8.97 (s, 1H), 8.87 (s, 2H), 8.74 (s, 1H), 8.36 (d, J= 8.0Hz, 3H), 7.65 (s, 2H), 7.54 (d, J=12.0Hz, 4H), 7.39 (d, J=12.0Hz, 3H), 7.14 (s, 2H), 6.90(s,2H).
The synthesis of 14. compound A14 of synthetic example
With compound A1, difference is to replace with 1- (4- boric acid phenyl) -2- phenyl -1H- benzimidazoles synthesis step 4- (4- phenyl boric acids)-terpyridyl of equivalent, obtains faint yellow solid 3.2g, yield 75.2%.
1H NMR (400MHz, Chloroform) δ 9.16 (d, J=16.0Hz, 8H), 8.97 (s, 2H), 8.45 (d, J= 80.0Hz, 6H), 7.74 (s, 4H), 7.65 (s, 3H), 7.53 (d, J=12.0Hz, 7H), 7.41 (s, 1H), 7.24 (d, J= 8.0Hz,12H).
The intermediate of the present invention and the analysis detection of compound use AB SCIEX mass spectrographs (4000QTRAP) and Brooker Nuclear Magnetic Resonance (400M).
Table 1：The analysis detecting data of composite structure compound in synthetic example
Compound Molecular formula MS(m/e) Elemental analysis (%)
A1 C76H50N4 1018.2 C,89.43；H,4.69；N,5.38
A2 C84H54N4 1118.3 C,90.28；H,4.63；N,4.74
A3 C80H50N4 1066.6 C,90.37；H,5.00；N,5.32
A4 C84H50N4 1114.9 C,90.41；H,4.65；N,4.73
A5 C46H30N4 638.4 C,86.39；H,4.47；N,8.31
A6 C46H30N4 638.7 C,86.35；H,4.53；N,8.62
A7 C48H28N6 688.4 C,83.43；H,5.69；N,12.35
A8 C48H28N6 688.7 C,83.26；H,5.47；N,12.38
A9 C54H34N4 738.4 C,87.85；H,4.29；N,7.46
A10 C56H36N2 736.8 C,92.85；H,5.29；N,3.46
A11 C46H30N4 638.5 C,86.36；H,4.65；N,8.38
A12 C70H46N4 942.4 C,89.22；H,4.76；N,5.64
A13 C70H46N4 942.2 C,89.53；H,4.82；N,6.15
A14 C68H44N6 944.2 C,86.53；H,4.52；N,9.15
Structure optimization is carried out to compound using Gauss software, computational methods are that the hydridization of density functional theory (DFT) is general Letter B3LYP and base group 6-31G (d, p), and the highest for evaluating compound A1, A5, A7, A9, A13 and known compound a, b accounts for There are molecular orbit (HOMO), lowest unoccupied molecular orbital (LUMO) and triplet state (T1) energy level, the results are shown in table 2.
Table 2：The compounds of this invention and documents compound energy level value
The compounds of this invention and the compound in patent KR2015024288A are can be seen that from above-mentioned comparison of computational results It compares, HOMO and LUMO are deeper, are more advantageous to the effect for playing hole barrier, while can reduce between successive functional layers It can be poor, advantageously reduce the voltage of device；And this patent compound is compared with patent WO03/060956, this patent compound Active site on parent nucleus is protected, and Thermodynamically stable can improve, and can be improved the device lifetime of material, more likely be realized Commercialized purposes, while having the characteristics that HOMO and LUMO are deeper, it can play the role of reducing voltage and hole barrier. Compared with publication compound, performance has obviously to be improved the compounds of this invention.
Device embodiments：
The structure of organic electroluminescence device of the present invention does not require particularly, can be well known to those skilled in the art Structure, be preferably as described below the structure of composition：
(1) anode/hole injection layer (HIL)/hole transmission layer (HTL)/luminescent layer (EML)/electron transfer layer (ETL)/ Electron injecting layer (EIL)/cathode；
(2) anode/hole transmission layer (HTL)/luminescent layer (EML)/hole blocking layer (HBL)/electron transfer layer (ETL)/ Electron injecting layer (EIL)/cathode
Above-mentioned "/" indicates to be laminated in order between different function layer.
In the preferred embodiment, organic electroluminescence device has lower operating voltage and higher luminous effect Rate.
Substrate can use the substrate in conventional organic luminescence organic electroluminescence device, such as：Glass or plastics.Anode Transparent high conductivity material, such as indium tin oxygen (ITO), indium zinc oxygen (IZO), stannic oxide (SnO2), oxygen may be used in material Change zinc (ZnO) etc..Glass substrate, ITO is selected to make anode material in the organic electroluminescence device of embodiment makes.
Common hole-injecting material has CuPc, TNATA and PEDT：PSS etc..The organic electroluminescence device of the present invention Hole injection layer uses 2-TNATA.
N, N '-two (3- tolyls)-N, N '-diphenyl-[1,1- xenyls] -4,4 '-two may be used in hole transmission layer The tri-arylamine groups material such as amine (TPD) or N, N '-diphenyl-N, N '-two (1- naphthalenes)-(1,1 '-xenyl) -4,4 '-diamines (NPB) Material.Hole mobile material selects NPB in the organic electroluminescence device that the present invention makes.
Organic electroluminescence device structure can be that single-shot photosphere can also be multi-luminescent layer structure.In the embodiment of the present invention Use the structure of single-shot photosphere.Luminescent layer includes light emitting host material and luminescent dye, wherein luminescent dye and the master that shines The mass ratio of body material is controlled by the evaporation rate both regulated and controled in device fabrication process, usually control luminescent dye with The evaporation rate ratio of light emitting host material is 1% to 8%, preferably 3% to 5%.
Common luminescent dye include metal iridium complex Ir (ppy), FIrpic and pure organic molecule, rubrene, DPP, DCJ, DCM etc..
Common light emitting host material includes Alq3, BAlq, AND, CBP, mCP, TBPe etc..
Common electron transport material has Alq3, Bphen, BCP, PBD etc., the present invention that Alq3, formula (a) is selected to be used as electronics Transmission layer material is compared with the compounds of this invention.
Selected cathode material is LiF/Al in the organic electroluminescence device of the present invention makes.
The different materials concrete structure used in the present invention is seen below：
Above-mentioned electroluminescent organic material, those skilled in the art, which are based on known method, can voluntarily prepare or be purchased from Chemical market It buys.
1. the compounds of this invention of device embodiments is used as electron transport material
The present embodiment prepares 9 organic electroluminescence devices altogether, and structure is, according to " hole injection layer on substrate (HIL) sequence of/hole transmission layer (HTL)/luminescent layer (EML)/electron transfer layer (ETL)/electron injecting layer (EIL)/cathode " Stacking, each layer are made of following material：
ITO/2-TNATA(30nm)/NPB(20nm)/CBP：Ir(ppy)3(5%) (20nm)/the compounds of this invention (50nm)/LiF(1nm)/Al。
Two of which compares organic electroluminescence device, and electron transport material selects Alq3 or formula (a) compound.
Organic electroluminescence device preparation process is as follows in the present embodiment：
The glass substrate that surface is coated with to transparent conductive film is cleaned by ultrasonic in cleaning solution, in deionized water It is ultrasonically treated, in ethyl alcohol：Ultrasonic oil removing, is baked under clean environment and completely removes moisture, use is ultraviolet in acetone mixed solution Lamp performs etching and ozone treatment, and low energy cation beam bombarded surface is used in combination；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned Vacuum evaporation 2-TNATA on anode tunic, adjusting evaporation rate are 0.1nm/s, form the hole injection layer that thickness is 30nm； Vacuum evaporation compound N PB on hole injection layer forms the hole transmission layer that thickness is 20nm, evaporation rate 0.1nm/s； Luminescent layers of the vacuum evaporation EML as device on hole transmission layer, EML include material of main part and dye materials, using more The method that source is steamed altogether, adjusting material of main part CBP evaporation rates are 0.1nm/s, and 3 evaporation rates of dye materials Ir (ppy) are according to mixing Miscellaneous ratio setting, vapor deposition total film thickness are 20nm；
The compounds of this invention or Alq3 is used to transmit layer material as device electronic, evaporation rate 0.1nm/s, vapor deposition is always Film thickness is 50nm；
For the LiF that vacuum evaporation thickness is 1nm on electron transfer layer (ETL) as electron injecting layer, thickness is 150nm's The Al layers of cathode as device.
To gained organic electroluminescence device in same brightness (10000cd/m2) under measure driving voltage and current efficiency, Performance is shown in Table 3.
Table 3：
The device performance data of device embodiments 1-1 to the 1-9 disclosed in table 3 are as it can be seen that in organic electroluminescence device In the case of other materials is identical in structure, the ETL materials of device are adjusted, compare device comparative example 1-8,1-9, can To significantly decrease the operating voltage of device, and increase substantially the luminous efficiency of device.This and the serial chemical combination in the present invention Object has deeper LUMO values and preferable electron mobility related.
2. the compound of the present invention of device embodiments is as light emitting host material.
Prepare 8 organic electroluminescence devices altogether, structure is, on substrate according to " anode/hole transmission layer (HTL)/ Each layer of luminescent layer (EL)/hole blocking layer (HBL)/electron transfer layer (ETL)/electron injecting layer (EIL)/cathode " is by following material Material is constituted：
ITO/NPB(50nm)/H1：D1 (5%) (30nm)/PBD (10nm)/Alq3 (50nm)/LiF (0.5nm)/Al (100nm).The feux rouges material of main part of one of device comparative example selects H1, the feux rouges of other 7 organic electroluminescence devices Material of main part selects the material of the present invention.
Organic electroluminescence device preparation process is as follows：
A) ITO (tin indium oxide) glass is cleaned：Respectively each 15 points of ito glass is cleaned with deionized water, acetone, EtOH Sonicate Then clock is handled 2 minutes in plasma cleaner；
B) vacuum evaporation or solution film forming hole transmission layer NPB, thickness 50nm on anode ito glass；
C) on hole transmission layer NPB, vacuum evaporation luminescent layer H1+D1 (5%), thickness 30nm；
D) on luminescent layer, vacuum evaporation hole blocking layer PBD, thickness 10nm；
E) on hole blocking layer PBD, vacuum evaporation electron transfer layer Alq3
F) on electron transfer layer Alq3, vacuum evaporation electron injecting layer LiF, thickness 0.5nm；
G) on electron injecting layer LiF, vacuum evaporation cathode Al, thickness 100nm.
To gained organic electroluminescence device in same brightness 5000cd/m2Lower measurement driving voltage and current efficiency, property 4 can be shown in Table.
Table 4：
The device performance data of device example 2-1 to the 2-8 disclosed in table 4 are as it can be seen that in organic electroluminescence device structure In the case of middle other materials is identical, the material of main part of luminescent layer in device is adjusted, compare device comparative example 2-1, It can be significantly improved and carry for the use of voltage and luminous efficiency two using the organic electroluminescence device of the compounds of this invention Height shows material of main part of the compounds of this invention as luminescent layer, and red phosphorescent organic electroluminescence device can be made to obtain more Good performance.
The preferred embodiment of the present invention has been described above in detail, still, during present invention is not limited to the embodiments described above Detail can carry out a variety of simple variants to technical scheme of the present invention within the scope of the technical concept of the present invention, this A little simple variants all belong to the scope of protection of the present invention.
It is further to note that specific technical features described in the above specific embodiments, in not lance In the case of shield, can be combined by any suitable means, in order to avoid unnecessary repetition, the present invention to it is various can The combination of energy no longer separately illustrates.
In addition, various embodiments of the present invention can be combined randomly, as long as it is without prejudice to originally The thought of invention, it should also be regarded as the disclosure of the present invention.

Claims (10)

1. compound has structure shown in following general formula (1)：
In formula (1), Ar1Selected from hydrogen atom, phenyl, naphthalene or Ar1It connect to form condensed ring virtue via divalent alkyl with phenyl Base；Ar2Selected from by the substituted or unsubstituted C of itrile group4~C20Nitrogenous heteroaryl.
2. compound according to claim 1, which is characterized in that Ar2Selected from following formula group：
3. compound according to claim 1, which is characterized in that Ar1Selected from phenyl, naphthalene, Ar2It indicates
4. compound according to claim 1, which is characterized in that Ar1Indicate hydrogen atom, Ar2It is selected from
5. compound according to claim 1, which is characterized in that the compound represents for following structural formula A1 to A14 Compound in one kind：
6. application of any compound of claim 1 to 5 in organic electroluminescence device.
7. application according to claim 6, any compound of claim 1 to 5 is in organic electroluminescence device In be used as electron transport material or light emitting host material.
8. a kind of organic electroluminescence device, including substrate, and sequentially forms anode layer on the substrate, at least contains The organic function layer and cathode layer of one layer of luminescent layer, it is characterised in that：In the organic function layer it is at least one layer of individually or as Blending constituent contains any compound of claim 1 to 5.
9. organic electroluminescence device according to claim 8, organic function layer includes hole injection layer, hole biography Defeated layer, luminescent layer, electron transfer layer and electron injecting layer, it is characterised in that：The electron transfer layer includes claim 1 to 5 Any compound.
10. organic electroluminescence device according to claim 8, it is characterised in that：The organic function layer includes red Color phosphorescence luminescent layer, the red phosphorescent luminescent layer material of main part include any compound of claim 1 to 5.
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