CN106684253B - A kind of indoles quinoxaline Organic Light Emitting Diode material - Google Patents

A kind of indoles quinoxaline Organic Light Emitting Diode material Download PDF

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CN106684253B
CN106684253B CN201611187198.4A CN201611187198A CN106684253B CN 106684253 B CN106684253 B CN 106684253B CN 201611187198 A CN201611187198 A CN 201611187198A CN 106684253 B CN106684253 B CN 106684253B
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CN106684253A (en
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李晓常
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GUANMAT OPTOELECTRONIC MATERIALS (JIANGXI) Inc
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    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • H10K50/10OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/654Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/655Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/657Polycyclic condensed heteroaromatic hydrocarbons
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/657Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • HELECTRICITY
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    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00Constructional details relating to the organic devices covered by this subclass
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00Constructional details relating to the organic devices covered by this subclass
    • H10K2102/301Details of OLEDs
    • H10K2102/302Details of OLEDs of OLED structures

Abstract

A kind of Organic Light Emitting Diode, it is characterized in that the Organic Light Emitting Diode, by a cathode, an organic semiconductor layer between anode and cathode and anode is formed, and an organic luminous layer is included wherein in organic semiconductor layer, containing an organic semiconductor compound, its general formula is:, it is characterized in that being connected a miscellaneous fusion ring of virtue in indoles quinoxaline, be conducive to improve charge balance injection and stability of photoluminescence, obtain high stable, high efficiency and the luminescent properties of long-life.

Description

A kind of indoles quinoxaline Organic Light Emitting Diode material
Technical field
The present invention relates to organic semiconductor in the application of organic luminescent device, especially a kind of balancing charge injection and transmission Organic semiconducting materials, can be applied to organic luminescent device as material of main part, improve device performance.
Background technology
Organic semiconducting materials belong to novel optoelectronic materials, its broad scale research is originating from 1977 by Hideki Shirakawa, A. Heeger and A. McDiamid are found that doped polyacetylene of the conductivity up to copper level jointly.Then, KodaK public affairs in 1987 C. Tang of department etc. have invented organic molecule light emitting diode(OLED), and the R. Friend and A. of nineteen ninety Cambridge University Holmes has invented polymer LED P-OLED, and S. Forrest in 1998 and M. Thomson have invented efficiency The Phosphorescent LED P HOLED of higher.Due to organic semiconducting materials have structure easily adjust can obtain it is numerous in variety, Can be with adjustable, or even the inexpensive benefit as being processed plastic film is multiple in conductive film, electrostatic plus organic semiconductor Print, photovoltaic solar cell application, Organic Thin Film Transistors logic circuit, and organic light emission OLED FPD and illumination etc. are many More applications, three scientists of Bai Chuan-Heeger-McDiamid obtained Nobel chemistry Prize in 2000.
As the Organic Light Emitting Diode of flat panel display of future generation, the requirement of organic photoelectric semiconductor has:It is 1. occurred frequently Light efficiency;2. excellent electronics and hole stability;3. suitable glow color;4. excellent film forming processability.Principle On, most of conjugacy organic molecule(Include star beam), conjugacy polymer, and contain the organic of conjugacy chromophore ligand Heavy metal complex, which has, possesses electroluminescence performance, applies in all kinds of light emitting diodes, such as organic molecule light emitting diode (OLED), polymer organic LED(POLED), Phosphorescent light emitting diode(PHOLED).Phosphorescence PHOLED dual-purposes Singlet excited state(Fluorescence)And Triplet Excited State(Phosphorescence)Luminescence mechanism, it is clear that than small molecule OLED and macromolecule POLED Much higher luminous efficiency.PHOLED manufacturing technologies and outstanding PHOLED materials are all to realize that low power consumption OLED shows and illuminates It is essential.The quantum efficiency and luminous efficiency of PHOLED is 3 ~ 4 times of fluorescence OLED material, therefore decreases generation Heat, increase the competitiveness of OLED display boards.This point provides so that generally OLED shows or illuminates and surmounts LCD and show Show and the possibility of conventional light source.Thus, more or less mix phosphorescent OLED material in existing high-end OLED device.
Phosphorescent OLED material is to be chelated by the organic light emission group containing certain conjugacy as two teeth, is formed with metallic element Ring metal-ligand complex compound, under high energy light photograph(Such as ultraviolet excitation)Or electric charge injection(It is electrically excited)Under the conditions of, due to ring Metal-ligand charge shifts(MLCT)As exciton, then revert to ground state and cause to shine.The note of electric charge in OLED device Enter is by after anode applies positive voltage, injecting hole, cathode injection electronics, respectively by electron transfer layer and sky from anode Layer is transferred in cave, while enters in the material of main part of emission layer, and the minimum end that electronics is eventually entered into light-emitting dopant accounts for molecule rail Road(LUMO), hole enters the highest occupied molecular orbital(HOMO) in light-emitting dopant(HOMO)And form excitation state light-emitting dopant point Son(Exciton state).With transmitting luminous energy after exciton state replying agent ground state, it is launched luminous energy wavelength face and answers light emitting molecule to mix Miscellaneous dose of energy gap(HOMO-LUMO energy level differences).
The existing heavy metal organic ligand complex compound much reported, is influenced by heavy metal and enhances spin(-)orbit and make With so that should weaker phosphorescence become very strong and excellent phosphorescent emissions be presented.Such as the three of green light(Phenylpyridine)Iridium (Ⅲ)Coordinate complex compound, referred to as Ir (PPY)3, it is with structural formula:
The FirPic of transmitting blue light has following structural formula:
Main ligand 4 therein, 6- difluoro-benzene yl pyridines dominate glow color.Launch the three of feux rouges(Octyl quinoline) Iridium(Ⅲ)Coordinate complex compound, there is excellent efficient transmission performance(Adv. Mater. 2007,19,739)Its structural formula is:
The compound of Yellow light-emitting low temperature is such as:
Ir(tptpy)2(acac)
With PL=560 nm(Chem. Mater. 2004, 16, 2480-2488)
To obtain efficient organic OLED, electron injection and electric transmission need to be usually added between luminescent layer and anode Layer, adds hole note and hole transmission layer between luminescent layer and cathode, so as to reach the electronics and sky balanced in luminescent layer Cave.It is worth noting that, in organic semiconductor, electric transmission mobility is usually less than hole transport mobility.Passed as electronics Defeated layer material is typically not occupy orbital energy level with relatively low LUMO-- is minimum, such as metal quinoline compound, such as three-(8- hydroxyls Base)Aluminium(Alq3), oxadiazoles or triazole type.Recently, document(Appl.Phys.Lett., 2007,90,183503 grade reports)Report The hole mobile material that road is made of biphenyl and arylamine, but dissolubility difference and film forming are difficult.
Luminescent layer is usually the semiconductor for being had by a small amount of luminescent material as object dopant incorporation one more high level Material of main part(Or bulk material Host material)Middle composition.Recent study shows, for same luminescent material or one Kind colour light emitting device, the difference of material of main part can cause different device light emitting efficiencies and working life.Therefore, develop new Material of main part is always the important topic for influencing Organic Light Emitting Diode practical application.It is preferable for ease of hole, the injection of electronics Material of main part should possess not only strong but also balance hole and electron injection and transmittability.To reach this purpose, have many Improved material of main part appears in the newspapers.V. Adamocich (US 2006/0280965) discloses the sheet that carbazole is connected with triphenylene Body material.C. Adachi (WO 2012/114745) discloses the bipolar host material being connected using pyridine with triphenylene. A. Dyatkin (US 2012/0256169) discloses the bipolarity master being made of benzothiophene, phenyl and indolepyridinium Body material.
The content of the invention
The present invention provides a kind of organic compound semiconductor, is connected a miscellaneous fusion ring of virtue by inhaling electrical indoles quinoxaline, Be conducive to improve charge balance injection and stability of photoluminescence, obtain high stable, high efficiency and the luminescent properties of long-life.Specifically should For a kind of Organic Light Emitting Diode, it is characterized in that the Organic Light Emitting Diode is made of such as lower part:
(a)One cathode,
(b) anode,
(c) a sandwich organic semiconductor luminescent layer between cathode and anode, the luminescent layer include a material of main part With a phosphor dopant, material of main part therein has following compound structure general formula:
It is characterized in that Y=O in the compound, S, S (O)2, C (R3)2, Si(R3)2, R3It is less than 16 for carbon number Alkyl, aryl;
It is characterized in that X is a singly-bound in the compound, a carbon atom is less than 16 aromatic ring, and a carbon atom is less than 16 heteroaromatic;
It is characterized in that Ar in the compound1-2It is less than 16 aromatic ring for carbon atom, carbon atom is fragrant miscellaneous less than 16 Ring;
It is characterized in that R1, R2 For H, D, F, alkyl of the carbon atom less than 16, alkoxy, containing fluoroalkyl.
High electronegativity indoles quinoxaline described in this patent can be obtained by various ways, and a typical multistep reaction is anti-as follows Answer shown in formula 1:
Fragrant miscellaneous fusion ring described in this patent can be obtained by various ways, a typical following institute of reaction equation 2 of multistep reaction Show:
A6, B6 or B7 that association reaction formula 1 and 2 is obtained, by typical coupled reaction as described in reaction equation 3,4 " Suzuki Suzuki " is reacted, and can obtain the compound described in this patent:
According to this patent requirement category, luminescent layer material of main part has a variety of in the Organic Light Emitting Diode Structural formula, includes 1 array structure of table in the case of one of which, hetero atom Y is O, S, or S in its formula of(O)2, be conducive to The electric charge injection efficiency of flat perseverance material of main part, obtains OLED device performances and improves.
Table 1:A kind of material of main part structure included in the case of
The category according to required by this patent, luminescent layer material of main part has more in the Organic Light Emitting Diode Kind structural formula, wherein including 2 array structures of table in another case, both hetero atom Y was C (R in general formula3)2, Si(R3)2, R3 For alkyl of the carbon number less than 16, aryl;Specifically, R3Can be that methyl, ethyl, propyl group, butyl or carbon number are less than 16 Other alkyl, carbon number be less than 16 heteroaromatic.These R3Substitution, is conducive to increase dissolubility, is conducive to purify or makes OLED luminescent devices are manufactured with solution spin coating, appearance liquid inkjet printing plated film.
Table 2:The structure included in another case
According to this patent requirement Organic Light Emitting Diode, it is characterized in that shining in the Organic Light Emitting Diode Ar in layer main body material compound1-2 Crosslinked group is partly or entirely connected with, crosslinked group is selected from vinyl, acrylate or three It is fluoride-based.On the one hand being connected with the compound of these crosslinked groups increases dissolubility, on the other hand dried by holding liquid film forming solvent It is in a heated condition, intermolecular that insoluble insoluble macromolecular network structure is formed by chemical crosslink reaction after dry, increase film Dimensional stability, and another layer of organic film can be applied again by solution methods in its surface, prepare sophisticated multilevel OLED devices.
In the case of one kind in the range of this patent, such as Ar1Or Ar2Have such as containing trifluoro vinyl luminescent layer material of main part Lower structure formula:
OrOr
Wherein Y=O, S, S (O)2, C (R3)2, Si(R3)2, R3For alkyl of the carbon number less than 16, aryl;Its feature exists X is a singly-bound in the compound, and a carbon atom is less than 16 aromatic ring, and a carbon atom is less than 16 heteroaromatic;
It is characterized in that Ar in the compound1-2It is less than 16 aromatic ring for carbon atom, carbon atom is fragrant miscellaneous less than 16 Ring;
It is characterized in that R1, R2 For H, D, F, alkyl of the carbon atom less than 16, alkoxy, containing fluoroalkyl.
Luminescent layer material of main part is more than 160 in heating-up temperature in the Organic Light Emitting DiodeoC, passes through chemical crosslinking Reaction forms insoluble cross-linked network structure:
What is more important of the present invention is that the organic semiconductor is applied to luminescent device.Usually, it is simplest Organic Light Emitting Diode is made of following several parts:
(a), a cathode;
(b), an anode;
(c), a sandwich organic semiconductor luminescent layer between cathode and anode, which includes a material of main part and one Phosphor dopant, material of main part compound therein have following general structure:
It is characterized in that Y=O in the compound, S, S (O)2, C (R3)2, Si(R3)2, R3It is less than 16 for carbon number Alkyl, aryl;It is characterized in that X is a singly-bound in the compound, a carbon atom is less than 16 aromatic ring, a carbon atom Heteroaromatic less than 16;
It is characterized in that Ar in the compound1-2It is less than 16 aromatic ring for carbon atom, carbon atom is fragrant miscellaneous less than 16 Ring;
It is characterized in that R1, R2 For H, D, F, alkyl of the carbon atom less than 16, alkoxy, containing fluoroalkyl.
According to the Organic Light Emitting Diode described in this patent scope, wherein in the Organic Light Emitting Diode in luminescent layer Luminescent material can be an emission wavelength be 510-550nm green light material;Luminescent material can also be that an emission wavelength is The yellow light material of 551-580nm;Or it is the red light material that an emission wavelength is 581-630nm.For obtain efficient green light and Feux rouges OLED, typically uses triplet state phosphorescent OLED emission layers therein and contains phosphorescent light-emitting materials, such as Ir (ppy)3To be green Light, or Ir (Piq)3 As red dopant, shone with 2 to 15% concentration(Weight)Material, is doped to a material of main part In.
According to the Organic Light Emitting Diode described in this patent scope, it is characterized in that described is organic sometimes for acquisition higher Performance light emitting diode, co-host material that can also be containing an increase electronics or Hole injection capacity in luminescent layer, namely Using hybrid agent material, wherein co-host material and the proportioning of primary body material is 5-45%.As green and red phosphorus Light OLED, material of main part of any triplet more than 2.4 eV all can answering as the luminescent material OLED of the present invention With.Preferable co-host material has electron-donating material DBPP:DBPP
Co-host material can also be following electronegativity material MCBP:
In traditional Organic Light Emitting Diode chip, typically using transparent conducting glass, or indium-tin-oxide is coated with One layer of hole injection layer HIL is deposited on ITO, then one layer of hole transmission layer HTL, luminescent layer EML, electron transfer layer successively ETL, electron injecting layer EIL, finally add one layer of metal, such as aluminum metal layer, as anode conducting and sealant.(Fig. 1)Work as ITO Connect positive electricity, after aluminium connection negative electricity arrives certain electric field, hole is transmitted to EML from ITO through HIL injections and HTL, and electronics is from aluminium company EML is transmitted to after the EIL injections connect, by ETL.Electronics meets in EML with hole, is combined into exciton(Exciton), Then part exciton is given off energy in the form of light radiation returns to ground state.The wavelength of light radiation is by the luminescent dopant in EML layers The energy gap of agent determines.
Common material of main part is to contain carbazole or arylamine structure class material.A kind of common material of main part is 4,4 '-N, N '- Two carbazoles-biphenyl (CBP):
More advanced has IPA-PCz and IPA-Ph-PCz(US20140225088):
To reach excellent phosphorescent devices performance, on anode, can an optional hole injection layer, such as blue or green blue(CuPc)Or Other compound (Appl.Phys.Lett., 69,2160 (1996), such as m-TDATA containing fragrant ammonia.
Similarly, between hole injection layer and emission layer EML, an also optional hole transmission layer, such as general 4,4 '- Double [N- (1- naphthyls)-N- phenylaminos] biphenyl(α-NPD)
For the injection in balance electronic and hole, luminous efficiency is improved, can optional electric transmission hole barrier(ETHB) material Material, example is 1,3,5- tri- (1- phenyl -1H- benzimidazolyl-2 radicals-yl) benzene TPBi, its structure is:
Between ETHL and cathode, also usually using electron injecting layer.Electron injecting layer is typically the relatively low metal of work content Lithium, lithium salts such as LiF, or its compound such as 8- hydroxyls lithium(Liq):
Therefore, OLED luminescent devices are a complicated sandwich constructions, and Fig. 1 is a typical construction, but is not uniquely should Use structure.The general thickness of wherein organic semiconductor layer is 50-250 nanometers, and preferably gross thickness is 80-180 nanometers.
Using OLED luminescent devices, shown available for flat screen, such as Mobile phone screen, i-Pack screens, TV screen, computer screen etc..
Brief description of the drawings
Fig. 1 is organic LED structure schematic diagram.
Embodiment
In order to make the foregoing objectives, features and advantages of the present invention clearer and more comprehensible, with reference to examples of implementation to this The embodiment of invention is described in detail.Many details are elaborated in the following description in order to fully understand The present invention.But the invention can be embodied in many other ways as described herein, those skilled in the art can be with Similar popularization is done in the case of without prejudice to intension of the present invention.Therefore the limit of the invention from following public specific embodiment System.
Embodiment 1:Compound it is synthetically prepared:
According to chemical equation 6,7, midbody compound A6-1 and B6-1 are prepared respectively, final reaction formula 8 is with 82% Yield prepare compound 2-1.
Similarly, the principles of chemistry are synthesized more than, without prejudice under scope, have synthesized following each material of main part Compound, specific listed compound by mass spectrum demonstrate molecular weight and molecule possessed by fragment, be specifically shown in table 3 below:
Table 3:Compound synthesis and characterization
2. device application example of embodiment:
In a base vacuum up to 10-5In the Multisource evaporation OLED Preparation equipments of pa, using following device mechanism: ITO/mTDATA(100Å)/NPD(400 Å)/Host:5% light-emitting dopant 10%(300 Å )/TPBi(300 Å)/LiF(10 Å)/ Al, using different Host OLED luminescent devices to compare.The vacuum deposition speed of wherein each organic layer and electrode Spend and table 4 is listed in the time.
Contrast material of main part:
Table 4:OLED device preparation conditions(Wt concentration 9% is adulterated in luminescent layer)
For cross-linking material of main part, material of main part and luminescent dopant agent solution, such as 15% are used(Weight)Dimethylbenzene is molten Liquid, heating evaporation solvent and completes that to be cross-linked into the insoluble luminescent layer not melted thin using spin coating and then in nitrogen glove box at the same time Film.
OLED devices made of all are tested after encapsulation and accelerated aging test.Its result summarizes such as table 5.
Table 5:OLED device performances (1000 nits of@)
Table 5 illustrates that the material of main part exemplified by the compounds of this invention is applied to known green light(512 nm of emission wavelength), feux rouges (619 nm of emission wavelength) doping illuminating OLED, which has, is obviously improved luminescent properties, than existing material of main part IPA-PCz, IPA-Ph-PCz has the luminous efficiency LE of higher(Lift up to 30%), and driving voltage is lower, accelerated life LT90%Extend 72%.
The above described is only a preferred embodiment of the present invention, not make limitation in any form to the present invention.Appoint What those skilled in the art, without departing from the scope of the technical proposal of the invention, all using the skill of the disclosure above Art content makes technical solution of the present invention many possible changes and modifications, or is revised as the equivalent embodiment of equivalent variations. Therefore, every content without departing from technical solution of the present invention, the technical spirit according to the present invention is to made for any of the above embodiments What simple modification, equivalent variation and modification, is still within the scope of the technical scheme of the invention.

Claims (10)

  1. A kind of 1. Organic Light Emitting Diode, it is characterized in that the Organic Light Emitting Diode is made of such as lower part:
    (a)One cathode,
    (b)One anode,
    (c)One sandwich organic semiconductor luminescent layer between cathode and anode, the luminescent layer include a material of main part and one Phosphor dopant, material of main part therein have following compound structure general formula:
    It is characterized in that Y=O in the compound, S, S (O)2, C (R3)2, Si(R3)2, R3It is less than 16 alkane for carbon number Base, aryl;
    It is characterized in that X is a singly-bound in the compound, a carbon atom is less than 16 aromatic ring, and a carbon atom is less than 16 Heteroaromatic;
    It is characterized in that Ar in the compound1-2It is less than 16 aromatic ring for carbon atom, carbon atom is less than 16 heteroaromatic;
    It is characterized in that R1, R2 For H, D, F, alkyl of the carbon atom less than 16, alkoxy, containing fluoroalkyl.
  2. 2. Organic Light Emitting Diode according to claim 1, it is characterized in that luminescent layer in the Organic Light Emitting Diode Ar in material of main part compound1-2 Crosslinked group is partly or entirely connected with, the crosslinked group is selected from vinyl, acrylate Or trifluoro vinyl.
  3. 3. Organic Light Emitting Diode according to claim 2, it is characterized in that luminescent layer in the Organic Light Emitting Diode Material of main part compound has following structural formula:
    Or Or
    It is characterized in that Y=O in the compound, S, S (O)2, C (R3)2, Si(R3)2, R3It is less than 16 alkane for carbon number Base, aryl;
    It is characterized in that X is a singly-bound in the compound, a carbon atom is less than 16 aromatic ring, and a carbon atom is less than 16 Heteroaromatic;
    It is characterized in that Ar in the compound1-2It is less than 16 aromatic ring for carbon atom, carbon atom is less than 16 heteroaromatic;
    It is characterized in that R in the compound1, R2 For H, D, F, alkyl of the carbon atom less than 16, alkoxy, containing fluoroalkyl.
  4. 4. Organic Light Emitting Diode according to claim 3, it is characterized in that luminescent layer in the Organic Light Emitting Diode Material of main part compound is more than 160 in heating-up temperatureoC, forms insoluble cross-linked network structure:
  5. 5. according to the Organic Light Emitting Diode described in claim 1, it is characterized in that luminescent layer in the Organic Light Emitting Diode Material of main part compound has following structural formula:
  6. 6. according to the Organic Light Emitting Diode described in claim 1, it is characterized in that luminescent layer in the Organic Light Emitting Diode Material of main part compound has following structural formula:
  7. 7. according to the Organic Light Emitting Diode described in claim 1, it is characterized in that luminescent layer in the Organic Light Emitting Diode In luminescent material be green light material that an emission wavelength is 510-550nm.
  8. 8. according to the Organic Light Emitting Diode described in claim 1, it is characterized in that luminescent layer in the Organic Light Emitting Diode In luminescent material be yellow light material that an emission wavelength is 551-580nm.
  9. 9. according to the Organic Light Emitting Diode described in claim 1, it is characterized in that luminescent layer in the Organic Light Emitting Diode In luminescent material be red light material that an emission wavelength is 581-630nm.
  10. 10. according to the Organic Light Emitting Diode described in claim 1, it is characterized in that luminescent layer in the Organic Light Emitting Diode In containing one increase electronics or Hole injection capacity co-host material, co-host material be electron-donating material DBPP or It is electronegativity material MCBP:
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* Cited by examiner, † Cited by third party
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CN104119370A (en) * 2013-04-25 2014-10-29 海洋王照明科技股份有限公司 Organic semiconductor material, preparation method thereof and electroluminescent device
CN105529407A (en) * 2014-10-17 2016-04-27 三星显示有限公司 Organic light-emitting device
CN106046006A (en) * 2015-04-06 2016-10-26 环球展览公司 Organic electroluminescent materials and devices

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Publication number Priority date Publication date Assignee Title
CN104119370A (en) * 2013-04-25 2014-10-29 海洋王照明科技股份有限公司 Organic semiconductor material, preparation method thereof and electroluminescent device
CN105529407A (en) * 2014-10-17 2016-04-27 三星显示有限公司 Organic light-emitting device
CN106046006A (en) * 2015-04-06 2016-10-26 环球展览公司 Organic electroluminescent materials and devices

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