CN107573927B - A kind of organic electroluminescence device - Google Patents
A kind of organic electroluminescence device Download PDFInfo
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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Abstract
The invention discloses a kind of 6- hydrogen iso-indoles simultaneously [2,1-a] Benzazole compounds, have the structural formula as shown in formula (1), wherein X represents alkyl or aryl, R1Selected from selected from C5‑C30Nitrogen-containing heterocycle, substituted azetidine or thick nitrogen-containing heterocycle aromatic hydrocarbons.The compound can be used as electron transport material, green or the red phosphorescent material of main part of organic electroluminescence device, the brightness of organic electroluminescence device and luminous efficiency can be made to improve, and reduce its driving voltage.
Description
The application is divisional application.Original application is Chinese patent application, application number: 201310456007.X, the applying date:
On September 29th, 2013, denomination of invention: 6- hydrogen iso-indoles simultaneously [2,1-a] Benzazole compounds and its application.
Technical field
The present invention relates to a kind of organic compound, more particularly, to organic electroluminescence device luminescent layer material of main part
Compound；The invention further relates to application of the compound in organic electroluminescence device.
Background technique
Electro optical phenomenon most early in 20th century the '30s be found, initial luminescent material be ZnS powder, thus send out
LED technology has been put on display, has been widely applied on energy-conserving light source now.And organic electroluminescent phenomenon is Pope in 1963 et al.
It finds earliest, they have found that the single layer crystal of anthracene under the driving of 100V or more voltage, can issue faint blue light.Until
Bi-layer devices are made in organic fluorescent dye by doctor Deng Qingyun of Kodak in 1987 et al. in a manner of vacuum evaporation, are being driven
Under voltage of the voltage less than 10 volts, external quantum efficiency has reached 1%, so that electroluminescent organic material and device are provided with reality
With the possibility of property, the research of OLED material and device has been pushed significantly from this.
Relative to phosphor, electroluminescent organic material has the advantage that 1. organic material processing performances are good,
It can be formed a film on any substrate by vapor deposition or the method for spin coating；2. the diversity of organic molecular structure can make can
To adjust thermal stability, the engineering properties, luminous and electric conductivity of organic material by the method for Molecular Design and modification
Can, the space so that material is significantly improved.
The principle of luminosity of organic electroluminescent diode is similar with inorganic light-emitting diode.When element is spread out by direct current
When raw forward bias voltage drop, voltage energy will drive electronics (Electron) and hole (Hole) respectively by cathode and anode in addition outside
Injection element forms the compound exciton of so-called electron-hole, exciton is by shining when the two meets in luminescent layer, combines
The form of relaxation returns to ground state, to achieve the purpose that luminous.
What the generation of organic electroluminescent was leaned on is the carrier (electrons and holes) transmitted in organic semiconducting materials
Recombination, it is well known that the electric conductivity of organic material is very poor, unlike inorganic semiconductor, does not continue in organic semiconductor
Energy band, the transmission of carrier commonly uses jump theory and describes, i.e., under the driving of an electric field, electronics is being excited or is being injected into
In the lumo energy of molecule, achieve the purpose that charge is transmitted via the lumo energy for jumping to another molecule.In order to make
Organic electroluminescence device reaches breakthrough in application aspect, it is necessary to overcome organic material charge inject and transmittability difference it is tired
It is difficult.Scientists are by the adjustment of device architecture, such as increase the number of device organic material layer, and make different organic layers
Play the part of different roles, such as the functional material having helps electronics to inject from cathode and hole from anode, some materials help
The transmission of charge, the material played the role of, which then plays, stops electronics and hole transport, most important certainly in organic electroluminescent
The luminescent material of various colors also to achieve the purpose that match with adjacent functional material, an excellent in efficiency service life long organic
Electroluminescent device is usually the optimization collocation of device architecture and various organic materials as a result, this is just that chemists design
The functionalization material for developing various structures provides greatly opportunities and challenges.
Common functionalization organic material has: hole-injecting material, hole mobile material, hole barrier materials, electronics note
Enter material, electron transport material, electron-blocking materials and light emitting host material and light-emitting guest (dyestuff) etc..
Hole-injecting material (HIM) requires its HOMO energy level between anode and hole transmission layer, is conducive to increase boundary
Hole injection between face.
Hole mobile material (HTM), it is desirable that there is high thermal stability (high Tg), with anode or hole-injecting material
There is lesser potential barrier, higher cavity transmission ability can vacuum evaporation formation pin-hole free films.Common HTM is that fragrance is more
Aminated compounds, mainly derivative of tri-arylamine group.
It is reversible and sufficiently high that electron transport material (Electron transport Material, ETM) requires ETM to have
Electrochemical reduction current potential, suitable HOMO and LUMO can rank value electronics is preferably injected, and be preferably provided with sky
Cave blocking capability；Higher electron transport ability, the film forming and thermal stability having had.ETM is typically electron deficient knot
The aromatic compound of the conjugate planes of structure.
Luminescent layer material of main part (host) needs to have following characteristics: reversible electrochemical redox current potential, and adjacent
Hole and the electron transfer layer HOMO that matches and LUMO can rank, the good and hole to match and electron transport ability, it is good
Good high thermal stability and film forming, and suitable singlet or triplet state energy gap are used to control exciton in luminescent layer,
There are also the good energy transfers between corresponding fluorescent dye or phosphorescent coloring.
The luminescent material needs of luminescent layer have the special feature that: having high fluorescence or phosphorescence quantum efficiency；Dyestuff
Absorption spectrum has had overlapping with the emission spectrum of main body, i.e., main body is adapted to dyestuff energy, can be effectively from main body to dyestuff
Energy transmission；Emission peak red, green, blue is as narrow as possible, with the excitation purity obtained；Stability is good, is able to carry out vapor deposition etc..
Up to the present, new electroluminescent organic material is still among continuous research and development, it has been found that Yi Leixin
Organic material, as shown in general formula (1):
It was found that this material may be used as material of main part in organic electroluminescence device, it is also used as electron-transport material
Material has more excellent efficiency and brightness.
Summary of the invention
Technical problem to be solved by the present invention lies in provide a new class of different Yin of 6- hydrogen for organic electroluminescent
Diindyl simultaneously [2,1-a] Benzazole compounds, this compound is as shown in general formula (1):
Wherein: X is selected from C1-C20Alkyl, C6-C20Aromatic radical, replace C6-C20Aromatic radical.R1Selected from C5-C30It is nitrogenous
Heterocycle, substituted azetidine or thick nitrogen-containing heterocycle aromatic hydrocarbons.
Preferably, the X is methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, amyl, isopentyl, ring penta
Base, alkyl-substituted cyclopenta, n-hexyl, cyclohexyl, alkyl-substituted cyclohexyl, phenyl, alkyl-substituted phenyl, benzyl.
Preferably, the R1 be selected from pyridyl group, substituted pyridinyl, pyridinylphenyl, benzimidazole, substituted benzimidazole,
Benzothiazole replaces benzothiazole, oxazole, substituted oxazoline, pyrimidine, substituted pyrimidines, pyrazine, replaces pyrazine, triazine, replaces three
Piperazine, quinolyl or isoquinolyl.
It is furthermore preferred that the compound is selected from following structural formula:
A kind of luminescent layer material of main part of organic electroluminescence device, it is characterised in that its described material of main part can be used
6- hydrogen iso-indoles of the present invention simultaneously [2,1-a] Benzazole compounds.
Also, a kind of organic electroluminescence device, including substrate, and sequentially form anode layer on the substrate,
Several luminescence unit layers and cathode layer；
The luminescence unit layer includes hole transmission layer, organic luminous layer and electron transfer layer, the luminescent layer
Material of main part uses 6- hydrogen iso-indoles of the present invention simultaneously [2,1-a] Benzazole compounds
Also, 6- hydrogen iso-indoles of the present invention simultaneously [2,1-a] Benzazole compounds may be used as red phosphorescent shine
The material of main part of layer, can also be used as the material of main part of green phosphorescent luminescent layer.
Also, simultaneously [2,1-a] Benzazole compounds may be used as electron transfer layer material to 6- hydrogen iso-indoles of the present invention
Material.
Also, simultaneously [2,1-a] Benzazole compounds can be used for organic electroluminescent to 6- hydrogen iso-indoles of the present invention
Device.
Detailed description of the invention
Fig. 1 is the nuclear-magnetism figure of the compound (M1) of the embodiment of the present invention 1.
Fig. 2 is the nuclear-magnetism figure of the compound (M7) of the embodiment of the present invention 7.
Fig. 3 is the nuclear-magnetism figure of the compound (P2) of the embodiment of the present invention 10.
Fig. 4 is the nuclear-magnetism figure of the compound (P1) of the embodiment of the present invention 18.
Fig. 5 is the nuclear-magnetism figure of the compound (P14) of the embodiment of the present invention 22.
Specific embodiment
It below will the invention will be further described by specific embodiment.
Intermediate shown in the present embodiment preparation formula (M1):
Synthetic method is as follows:
(1) synthesis of 1- (2- iodine benzyl) -3- Methyl-1H-indole
700 milliliters of dimethyl sulfoxides, 52 grams of potassium hydroxide, 26.2 grams of 3- are added under nitrogen protection for 1000 milliliters of there-necked flasks
After 30 points of kinds are stirred at room temperature, 50.5 grams of adjacent iodine benzyl chlorides are added in methyl indol.Then it is stirred at room temperature 3 hours, is poured into 2000 milliliters of water
In, ethyl acetate extracts, and is washed to neutrality, silica gel post separation, petroleum ether: ethyl acetate volume ratio=10:1 elution is produced
55.1 grams of product, MS (m/e): 347.
(2) synthesis of 11- methyl -6H- iso-indoles simultaneously [2,1-a] indoles
34.7 grams of 1- (2- iodine benzyl) -3- methyl-1 H- Yin is added in 1000 milliliters of there-necked flasks, nitrogen protection, mechanical stirring
Diindyl, 1 gram of copper powder, 30 grams of potassium carbonate, 600 milliliters of PEG400 (polyethylene glycol 400) are to slowly warm up to 180 degree, react 24 hours,
Cooling, is poured into 2000 milliliters of water, and methylene chloride extracts, after dichloromethane layer magnesium sulfate drying, silica gel column chromatography separation, and stone
Oily ether: ethyl acetate: the elution of methylene chloride volume ratio=10:1:1 obtains 10.2 grams of product, and MS (m/e): 219.
(3) synthesis of M1
500 milliliters of there-necked flasks, are added 9 grams of 11- methyl -6H- iso-indoles simultaneously [2,1-a] indoles, 300 milliliters of methylene chloride,
It is cooled to 0-5 DEG C, is slowly added dropwise 20 milliliters of dichloromethane solutions of 14.5 grams of bromines, drop finishes that be to slowly warm up to 20 DEG C of reactions 2 small
When, solution of sodium bisulfite washing, washing, dichloromethane layer silica gel post separation, petroleum ether: ethyl acetate: methylene chloride is added
The elution of volume ratio=10:1:1, obtains 12.1 grams of product, and MS (m/e): 377, the nuclear magnetic spectrogram (1H) of product M1 is shown in 1 institute of attached drawing
Show.
Intermediate shown in the present embodiment preparation formula (M2):
Synthetic method is as follows:
Under nitrogen protection, 3.8 grams of M1 are added, 300 milliliters of DMSO are slowly added to 1.6 grams of contents in 500 milliliters of there-necked flasks
4.3 grams of iodomethane are added after stirring 30 minutes in 60% sodium hydride, react at room temperature 12 hours, it is not anti-that a small amount of Methanol Decomposition is added
After the sodium hydride answered, reaction solution is poured into 900 milliliters of water, methylene chloride extracts, washing, dichloromethane layer silica gel post separation,
Petroleum ether: ethyl acetate: the elution of methylene chloride volume ratio=10:1:1 obtains 3.0g grams of product, and MS (m/e): 405.
3-embodiment of embodiment 6
Referring to the method for embodiment 2, intermediate M3-M6 totally 4 intermediates are prepared for, specific data are as follows:
Embodiment 7
Intermediate shown in the present embodiment preparation formula (M7):
Synthetic method is as follows:
3.8 grams of M1 are added in 500 milliliters of there-necked flasks, nitrogen protection, and 300 milliliters of DMSO are slowly added to 1.6 grams of contents 60%
After stirring 30 minutes, 6.0 grams of iodobenzenes are added in sodium hydride, and 0.6 gram of Pd (dppp) Cl2 is to slowly warm up to 50 DEG C, are reacted 24 hours,
After the unreacted sodium hydride of a small amount of Methanol Decomposition is added, reaction solution is poured into 900 milliliters of water, methylene chloride extracts, washing, and two
Chloromethanes layer silica gel post separation, petroleum ether: ethyl acetate: methylene chloride volume ratio=10:1:1 elution obtains 1.5g grams of product,
The nuclear magnetic spectrogram (1H) of MS (m/e): 529, product M7 are as shown in attached drawing 2.
8-embodiment of embodiment 9
According to the method for embodiment 7, intermediate M8 and M9 totally 2 intermediates are prepared for, specific data are as follows:
Embodiment 10
Shown in compound manufactured in the present embodiment such as formula (P2):
Synthetic method is as follows:
4.0g M2,2.7g pyridine -3- boric acid, 0.6g tetra-triphenylphosphine palladium, 9.1g carbonic acid is added in 250 milliliters of there-necked flasks
Potassium, 80 milliliters of toluene, 50 milliliters of ethyl alcohol, 30 milliliters of water under nitrogen protection, heating reflux reaction 8 hours, cool down, filtering, solid
After drying, silica gel column chromatography separation, petroleum ether: ethyl acetate: methylene chloride volume ratio=10:1:3 elution obtains product 3.1g
Gram, MS (m/e): 401, the nuclear magnetic spectrogram (1H) of compound P2 is as shown in attached drawing 3.
11-embodiment of embodiment 17
According to the method for embodiment 10, using intermediate M2 and corresponding acid reaction, following 7 products have been synthesized,
Specific data are as follows:
Embodiment 18
Shown in compound manufactured in the present embodiment such as formula (P1):
Synthetic method is as follows:
500 milliliters of there-necked flasks, are added 4.0g M2, and 300 milliliters of tetrahydrofurans are cooled to -78 DEG C, are slowly added dropwise 10 milliliters
The butyl lithium hexane solution of 2.4M finishes and keeps the temperature 1 hour in -78 DEG C, and 5.6g triisopropyl borate ester is added, is warmed to room temperature naturally
Reaction 2 hours, is poured into aqueous ammonium chloride solution, and ethyl acetate extracts organic layer, after the drying of organic layer magnesium sulfate, is concentrated into
It is dry, it is directly added into 80 milliliters of toluene, 50 milliliters of ethyl alcohol, 30 milliliters of water, 1.13g 2- chloropyridine, 0.4g tetra-triphenylphosphine palladium, nitrogen
Under gas shielded, heating reflux reaction 8 hours, cool down, filtering, after solid is dry, silica gel column chromatography separation, petroleum ether: acetic acid second
Ester: the elution of methylene chloride volume ratio=10:1:3 obtains 1.4g grams of product, and MS (m/e): 401, the nuclear magnetic spectrogram of compound P1
(1H) is as shown in attached drawing 4.
19-embodiment of embodiment 21
It according to the method for embodiment 18, is reacted using intermediate M2 and corresponding chloro thing, has synthesized following 3 productions
Product, specific data are as follows:
Embodiment 22
Shown in compound manufactured in the present embodiment such as formula (P14):
The same P11 of synthetic method, only changes M2 into M7, obtains 6.1g grams of product, and MS (m/e): 857, the core of compound P14
Magnetic spectrum figure (1H) is as shown in attached drawing 5.
Embodiment 23
Shown in compound manufactured in the present embodiment such as formula (P15):
The same P2 of synthetic method, only changes M2 into M7, obtains 4.1g grams of product, and MS (m/e): 525.
Embodiment 24
Shown in compound manufactured in the present embodiment such as formula (P16):
The same P7 of synthetic method, only changes M2 into M3, obtains 6.7g grams of product, and MS (m/e): 919.
Embodiment 25
Shown in compound manufactured in the present embodiment such as formula (P17):
The same P13 of synthetic method, only changes M2 into M3, obtains 3.3g grams of product, and MS (m/e): 845.
Embodiment 26
Shown in compound manufactured in the present embodiment such as formula (P18):
The same P3 of synthetic method, only changes M2 into M4, obtains 5.7g grams of product, and MS (m/e): 693.
Embodiment 27
Shown in compound manufactured in the present embodiment such as formula (P19):
The same P2 of synthetic method, only changes M2 into M4, obtains 4.1g grams of product, and MS (m/e): 541.
Embodiment 28
Shown in compound manufactured in the present embodiment such as formula (P21):
The same P8 of synthetic method, only changes M2 into M5, obtains 5.6g grams of product, and MS (m/e): 733.
Embodiment 29
Shown in compound manufactured in the present embodiment such as formula (P22):
The same P3 of synthetic method, only changes M2 into M5, obtains 6.1g grams of product, and MS (m/e): 773.
Embodiment 30
Shown in compound manufactured in the present embodiment such as formula (P23):
The same P12 of synthetic method, only changes M2 into M8, obtains 2.1g grams of product, and MS (m/e): 707.
Embodiment 31
Shown in compound manufactured in the present embodiment such as formula (P24):
The same P3 of synthetic method, only changes M2 into M8, obtains 2.1g grams of product, and MS (m/e): 705.
Embodiment 32
Shown in compound manufactured in the present embodiment such as formula (P25):
The same P1 of synthetic method, only changes M2 into M9, obtains 3.0g grams of product, and MS (m/e): 843.
Embodiment 33
Shown in compound manufactured in the present embodiment such as formula (P26):
The same P3 of synthetic method, only changes M2 into M9, obtains 5.6g grams of product, and MS (m/e): 841.
Embodiment 34
Shown in compound manufactured in the present embodiment such as formula (P27):
The same P2 of synthetic method, only changes M2 into M6, obtains 5.0g grams of product, and MS (m/e): 553.
Embodiment 35
Shown in compound manufactured in the present embodiment such as formula (P28):
The same P3 of synthetic method, only changes M2 into M6, obtains 5.2g grams of product, and MS (m/e): 705.
It is the Application Example of the compounds of this invention below:
The typical structure of OLED organic electroluminescence device are as follows:
Substrate/anode/hole transmission layer (HTL)/organic luminous layer (EL)/electron transfer layer (ETL)/cathode
The substrate in conventional organic luminescence organic electroluminescence device can be used in substrate, such as: glass or plastics.Anode
Material can use transparent high conductivity material, such as indium tin oxygen (ITO), indium zinc oxygen (IZO), stannic oxide (SnO2), oxygen
Change zinc (ZnO) etc..Glass substrate is selected in organic electroluminescence device production of the invention, ITO makees anode material.
Hole transmission layer can use N, N '-two (3- tolyl)-N, N '-diphenyl-[1,1- xenyl] -4,4 '-two
The tri-arylamine groups material such as amine (TPD) or N, N '-diphenyl-N, N '-two (1- naphthalene)-(1,1 '-xenyl) -4,4 '-diamines (NPB)
Material.Wherein NPB is common hole mobile material, and selected hole passes in organic electroluminescence device production of the invention
Defeated material selection NPB.
Organic electroluminescence device structure can be also possible to multi-luminescent layer structure for single-shot photosphere.
Electron transfer layer uses Alq3 or TAZ or TPBi or any two kinds of the collocation for being derived from these three materials.
Selected cathode material is LiF/Al in organic electroluminescence device production of the invention.
Different materials specific structure used in the present invention is seen below:
Embodiment 36:
The present embodiment prepares 16 organic electroluminescence devices, structure altogether are as follows: and ITO/NPB (40nm)/EM1 (30nm)/
ETL material (20nm)/LiF (0.5nm)/Al (150nm)；
One of comparison organic electroluminescence device, electron transport material select Bphen, remaining 15 organic electroluminescence hair
Optical device selects material of the invention.
Organic electroluminescence device preparation process is as follows in the present embodiment:
The glass plate for being coated with transparent conductive layer is ultrasonically treated in commercial detergent, is rinsed in deionized water,
In acetone: ultrasonic oil removing in alcohol mixed solvent is baked under clean environment and completely removes moisture content, clear with ultraviolet light and ozone
It washes, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned
Anode tunic vacuum evaporation NPB is 50nm as hole transmission layer, evaporation rate 0.1nm/s, vapor deposition film thickness；
Luminescent layer of the vacuum evaporation EM1 as device on hole transmission layer, evaporation rate 0.1nm/s, vapor deposition are total
Film thickness is 30nm；
The electricity of one layer of the compound of the present invention of vacuum evaporation or Bphen as organic electroluminescence device on luminescent layer
Sub- transport layer, evaporation rate 0.1nm/s, vapor deposition total film thickness are 50nm；
The LiF of vacuum evaporation 0.5nm is as electron injecting layer on electron transfer layer (ETL), and the Al of 150nm is as yin
Pole.
Organic electroluminescence device performance see the table below:
It can see by upper table, organic material of the invention may be used as electron transfer layer in organic electroluminescence device
Materials'use.
Embodiment 37:
The compound of the present invention is as the material of main part in red phosphorescent OLED organic electroluminescence device:
7 organic electroluminescence devices, organic electroluminescence device structure are prepared altogether are as follows:
ITO/NPB (20nm)/feux rouges material of main part (30nm): Ir (piq) 3 [5%]/TPBI (10nm)/Alq3 (15nm)/
LiF(0.5nm)/Al(150nm)。
One of them is comparison organic electroluminescence device, and feux rouges material of main part selects CBP, other 6 organic electroluminescences hairs
Optical device selects material of the invention.
Organic electroluminescence device preparation process is as follows: the glass plate for being coated with transparent conductive layer is cleaned in commercialization
It is ultrasonically treated in agent, rinses in deionized water, in acetone: ultrasonic oil removing in alcohol mixed solvent is toasted under clean environment
To completely removing moisture content, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, 1 × 10-5~9 × 10-3Pa is evacuated to,
Vacuum evaporation hole transmission layer NPB on above-mentioned anode tunic, evaporation rate 0.1nm/s, vapor deposition film thickness are 20nm；
Vacuum evaporation light emitting host material and dyestuff on hole transmission layer, as shining for organic electroluminescence device
Layer, evaporation rate 0.1nm/s, vapor deposition total film thickness are 30nm；
Successively vacuum evaporation electron transfer layer TPBI and Alq3, evaporation rate are 0.1nm/s on luminescent layer, are steamed
Plating film thickness is respectively 10nm and 15nm；
The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as cathode.
Organic electroluminescence device performance see the table below:
Can see by upper table, using chemical combination of the present invention as phosphorescence host organic electroluminescence device relative to use
CBP obtains preferable effect as the organic electroluminescence device of main body, obtains higher current efficiency and lower drive
Dynamic voltage.
Embodiment 38:
The compound of the present invention is as the material of main part in green phosphorescent OLED organic electroluminescence device:
8 organic electroluminescence devices, organic electroluminescence device structure are prepared altogether are as follows:
ITO/NPB (20nm)/green light material of main part (30nm): Ir (ppy) 3 [7%]/TPBI (10nm)/Alq3 (15nm)/
LiF(0.5nm)/Al(150nm)。
One of them is comparison organic electroluminescence device, and green light material of main part selects CBP, other 7 organic electroluminescences
Luminescent device selects material of the invention.
Organic electroluminescence device preparation process is as follows: the glass plate for being coated with transparent conductive layer is cleaned in commercialization
It is ultrasonically treated in agent, rinses in deionized water, in acetone: ultrasonic oil removing in alcohol mixed solvent is toasted under clean environment
To completely removing moisture content, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, 1 × 10-5~9 × 10-3Pa is evacuated to,
Vacuum evaporation hole transmission layer NPB on above-mentioned anode tunic, evaporation rate 0.1nm/s, vapor deposition film thickness are 20nm；
Vacuum evaporation light emitting host material and dyestuff on hole transmission layer, as shining for organic electroluminescence device
Layer, evaporation rate 0.1nm/s, vapor deposition total film thickness are 30nm；
Successively vacuum evaporation electron transfer layer TPBI and Alq3, evaporation rate are 0.1nm/s on luminescent layer, are steamed
Plating film thickness is respectively 10nm and 15nm；
The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as electron injecting layer and cathode.
Organic electroluminescence device performance see the table below:
Can see by upper table, using chemical combination of the present invention as phosphorescence host organic electroluminescence device relative to use
CBP obtains preferable effect as the organic electroluminescence device of main body, obtains higher current efficiency and lower drive
Dynamic voltage.
Obviously, the above embodiments are merely examples for clarifying the description, and does not limit the embodiments.It is right
For those of ordinary skill in the art, can also make on the basis of the above description it is other it is various forms of variation or
It changes.There is no necessity and possibility to exhaust all the enbodiments.And it is extended from this it is obvious variation or
It changes still within the protection scope of the invention.
Claims (4)
1. a kind of organic electroluminescence device, contain simultaneously [2, the 1-a] Benzazole compounds of 6- hydrogen iso-indoles shown in formula (1):
Wherein: X is selected from methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, amyl, isopentyl, cyclopenta, alkyl substitution
Cyclopenta, n-hexyl, cyclohexyl, alkyl-substituted cyclohexyl, phenyl, alkyl-substituted phenyl, benzyl；
R1 is selected from pyridyl group, substituted pyridinyl, pyridinylphenyl, benzimidazole, substituted benzimidazole, benzothiazole, substituted benzene
And thiazole, pyrimidine, substituted pyrimidines, pyrazine, substitution pyrazine, substitution triazine, quinolyl or isoquinolyl；
The organic electroluminescence device is red organic electroluminescence device；Simultaneously [the 2,1- of 6- hydrogen iso-indoles shown in the formula (1)
A] Benzazole compounds are used as luminescent layer material of main part in organic electroluminescence device.
2. organic electroluminescence device according to claim 1, which is characterized in that the different Yin of 6- hydrogen shown in formula (1) therein
Simultaneously [2,1-a] Benzazole compounds are selected from flowering structure diindyl:
3. organic electroluminescence device according to claim 1, it is characterised in that including substrate, and be sequentially formed at institute
State anode layer, several luminescence unit layers and the cathode layer on substrate；
The luminescence unit layer includes hole transmission layer, luminescent layer and electron transfer layer；
The luminescent layer is red phosphorescent luminescent layer；
The material of main part of the red phosphorescent luminescent layer is simultaneously [2,1-a] Benzazole compounds of 6- hydrogen iso-indoles described in formula (1).
4. organic electroluminescence device according to claim 3, it is characterised in that:
The material of main part of the red phosphorescent luminescent layer is selected from following compound:
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| CN201710819240.8A CN107573927B (en) | 2013-09-29 | 2013-09-29 | A kind of organic electroluminescence device |
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| CN201310456007.XA CN104513244B (en) | 2013-09-29 | 2013-09-29 | Simultaneously [2,1 a] Benzazole compounds and its application of 6 hydrogen iso-indoles |
| CN201710819240.8A CN107573927B (en) | 2013-09-29 | 2013-09-29 | A kind of organic electroluminescence device |
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| CN201710818081.XA Active CN107546339B (en) | 2013-09-29 | 2013-09-29 | A kind of organic electroluminescence device |
| CN201710818055.7A Withdrawn CN107556321A (en) | 2013-09-29 | 2013-09-29 | A kind of organic electroluminescence device |
| CN201710814416.0A Withdrawn CN107602562A (en) | 2013-09-29 | 2013-09-29 | The synthetic method of 6 hydrogen iso-indoles simultaneously [2,1 a] Benzazole compounds |
| CN201710819240.8A Active CN107573927B (en) | 2013-09-29 | 2013-09-29 | A kind of organic electroluminescence device |
| CN201310456007.XA Active CN104513244B (en) | 2013-09-29 | 2013-09-29 | Simultaneously [2,1 a] Benzazole compounds and its application of 6 hydrogen iso-indoles |
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| CN201710818055.7A Withdrawn CN107556321A (en) | 2013-09-29 | 2013-09-29 | A kind of organic electroluminescence device |
| CN201710814416.0A Withdrawn CN107602562A (en) | 2013-09-29 | 2013-09-29 | The synthetic method of 6 hydrogen iso-indoles simultaneously [2,1 a] Benzazole compounds |
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| US6713194B2 (en) * | 2002-05-14 | 2004-03-30 | Lightronik Technology Inc. | Organic electroluminescence element |
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| CN1192684C (en) * | 2002-06-05 | 2005-03-09 | 谢爽 | Organic electroluminescent device |
| WO2012040923A1 (en) * | 2010-09-29 | 2012-04-05 | Merck Sharp & Dohme Corp. | Tetracyclic indole derivatives and methods of use thereof for the treatment of viral diseases |
| WO2012050848A1 (en) * | 2010-09-29 | 2012-04-19 | Schering Corporation | Fused tetracycle derivatives and methods of use thereof for the treatment of viral diseases |
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| US6713194B2 (en) * | 2002-05-14 | 2004-03-30 | Lightronik Technology Inc. | Organic electroluminescence element |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107556321A (en) | 2018-01-09 |
| CN104513244B (en) | 2017-12-08 |
| CN107573927A (en) | 2018-01-12 |
| CN107546339A (en) | 2018-01-05 |
| CN107546339B (en) | 2019-02-05 |
| CN104513244A (en) | 2015-04-15 |
| CN107602562A (en) | 2018-01-19 |
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