CN106654035A - Organic semiconductor host material and application thereof in organic light emitting diode - Google Patents
Organic semiconductor host material and application thereof in organic light emitting diode Download PDFInfo
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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Abstract
The invention relates to an organic semiconductor host material and an application thereof in an organic light emitting diode. The organic light emitting diode is characterized by consisting of a negative electrode, a positive electrode, and an organic semiconductor layer between the negative electrode and the positive electrode, wherein the organic semiconductor layer comprises an organic light emitting layer which comprises an organic semiconductor host material having a general formula as follows: a formula is as shown in the specification; the organic semiconductor layer is characterized in that a nitrogen-atom-containing heteroaromatic fused ring is connected to a N atom of developed indoloquinoxaline, so that charge balance injection and light emitting stability can be improved, and high-stability, high-efficiency and long-service life light emitting performance can be obtained.
Description
Technical field
The present invention relates to application of the organic semiconductor in organic luminescent device, especially a kind of balancing charge injection and transmission
Organic semiconducting materials, organic luminescent device can be applied to as material of main part, improve device performance.
Background technology
Organic semiconducting materials belong to novel optoelectronic materials, and its broad scale research originates from 1977 by Hideki Shirakawa, A.
Heeger and A. McDiamid are found that doped polyacetylene of the conductance up to copper level jointly.Subsequently, 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
Higher Phosphorescent LED P HOLED.Can obtain numerous in variety because there is organic semiconducting materials structure easily to adjust,
Can be with adjustable, or even the inexpensive benefit as plastic sheeting processing adds organic semiconductor in conductive film, and electrostatic is multiple
The crowd such as print, photovoltaic solar cell application, OTFT logic circuit, and organic light emission OLED FPD and illumination
Many applications, three scientists of Bai Chuan-Heeger-McDiamid obtained Nobel chemistry Prize in 2000.
Used as the Organic Light Emitting Diode of flat panel display of future generation, organic photoelectric semiconductor requires have：1. high luminous
Efficiency；2. excellent electronics and hole stability；3. suitable glow color；4. excellent film forming processability.In principle,
Most of conjugacy organic molecule（Comprising star beam）, conjugacy polymer, and containing the organic heavy of conjugacy chromophore part
Metal complex has and 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 and generally OLED is shown or illuminates that to surmount LCD aobvious
Show and conventional light source possibility.Thus, more or less mix phosphorescent OLED material in existing high-end OLED.
Phosphorescent OLED material is chelated as two teeth by the organic light emission group containing certain conjugacy, is formed with metallic element
Ring metal-ligand complex compound, in the case where high energy light shines（Such as ultraviolet excitation）Or electric charge injection（It is electrically excited）Under the conditions of, due to ring
Metal-ligand charge is shifted（MLCT）Become exciton, then revert to ground state and cause to light.The note of electric charge in OLED
Enter is after applying positive voltage in anode, from anode hole, negative electrode injection electronics, respectively through electron transfer layer and sky to be injected
Layer is transferred in cave, while into the material of main part of emission layer, the minimum end that electronics is eventually entered into light-emitting dopant accounts for molecule rail
Road（LUMO）, the highest occupied molecular orbital(HOMO) that hole is entered in light-emitting dopant（HOMO）And form excitation state light-emitting dopant point
Son（Exciton state）.Along with transmitting luminous energy after exciton state replying agent ground state, its transmitting luminous energy wavelength just correspond to light emitting molecule and mix
Miscellaneous dose of energy gap（HOMO-LUMO energy level differences）.
The heavy metal organic ligand complex compound of existing many reports, is affected by heavy metal and enhances spin(-)orbit and make
With so that should weaker phosphorescence become very strong and excellent phosphorescent emissions be presented.The three of such as green light（Phenylpyridine）Iridium
（Ⅲ）Coordinate complex compound, referred to as Ir (PPY)3, and its derivative I r (MePPY)3It is with structural formula：
The FirPic of transmitting blue light has following structural formula： FirPic
Main part 4 therein, 6- difluoro-benzene yl pyridines dominate glow color.The three of transmitting ruddiness（Octyl quinoline）Iridium
（Ⅲ）Coordinate complex compound, with excellent efficient transmission performance（Adv. Mater. 2007,19,739）Its structural formula is：Ir(piq-hex)3,
The compound of Yellow light-emitting low temperature is such as：Ir(tptpy)2(acac), with PL=560nm（Chem. Mater. 2004, 16, 2480-2488）.
To obtain efficient organic OLED, electron injection and electric transmission generally need to be added between luminescent layer and anode
Layer, hole note and hole transmission layer are added between luminescent layer and negative electrode, so as to reach the electronics balanced in luminescent layer with sky
Cave.It should be noted that in organic semiconductor, electric transmission mobility is usually less than hole transport mobility.Pass as electronics
Defeated layer material does not typically occupy orbital energy level, such as metal quinoline compound with relatively low LUMO-- is minimum, 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 up of biphenyl and arylamine, but dissolubility difference and film forming are difficult.
Luminescent layer is usually to mix a semiconductor with more high level as object dopant by a small amount of luminescent material
Material of main part（Or bulk material Host material）Middle composition.Recent study shows, for same luminescent material or one
Kind of colour light emitting device, the difference of material of main part can cause different device light emitting efficiency and working life.Therefore, develop new
Material of main part always affects the important topic of Organic Light Emitting Diode practical application.It is preferable for ease of hole, the injection of electronics
Material of main part should possess hole that is not only strong but also balancing and electron injection and transmittability.To reach this purpose, there is many
Improved material of main part appears in the newspapers.K.Y.Hwang (US 2014/0225088) is disclosed by indoles quinoxaline, phenyl and N- benzene
The bulk material that base carbazole is constituted.C. Adachi (WO 2012/114745) is disclosed and is connected with triphenylene using pyridine
Bipolar host material.A. Dyatkin (US 2012/0256169) is disclosed by benzothiophene, phenyl and indolepyridinium
The bipolar host material for being constituted.
The content of the invention
The present invention provides a kind of organic compound semiconductor, connect on electrical indoles quinoxaline N atoms a nitrogenous virtue by inhaling
Miscellaneous fused rings, such as pyridine indoles or carbazole, are conducive to improving charge balance injection and stability of photoluminescence, obtain high stable, efficiently
Rate and long-life luminescent properties.A kind of Organic Light Emitting Diode is applied particularly to, it is characterized in that described organic light-emitting diodes
Pipe is made up of following part：
(a) negative electrode
(b) anode
C () sandwich organic semiconductor luminescent layer between negative electrode and anode, the luminescent layer includes a material of main part and
Phosphor dopant, material of main part therein has following general structure：
Y is C or N in wherein described compound；Ar1For aromatic ring of H, D, F, one carbon atom less than 18, carbon atom is less than
18 heteroaromatic a, carbon atom condenses heteroaromatic less than 18；Ar2-3For H, aromatic ring of the carbon atom less than 18 a, carbon atom is little
In 18 heteroaromatic, a carbon atom condenses heteroaromatic less than 18.
For MOLECULE DESIGN purpose, consciously from electrophilicity heteroaromatic（acceptor）Pyridine indoles and hole transport
Property heteroaromatic（donor）Carbazole, it is aided with aromatic ring or heteroaromatic is combined into molecule so that described compound has D-A bipolaritys
Structure.
In different textural associations, such as（I）There are various differences in described organic semiconductor compound principle
Combination, when Y is N, wherein structure is comprising as follows：
Table 1：
。
In different textural associations, such as（I）There are various differences in described organic semiconductor compound principle
Combination, when Y is C, wherein structure is comprising as follows：
Table 2：
。
Ar in described Organic Light Emitting Diode in luminescent layer material of main part2-3At least one crosslinking group can be also connected with
The unit of group.Have many chemical groups all to possess crosslinking function, wherein be typically included in heating or ultraviolet light shine under friendship
Symbasis group, row are such as connected on phenyl ring and include vinyl as follows（A）, acrylic（B）And trifluoro vinyl（C）：
In principle above group can reach increase dissolubility by chemical bonding in the host compound of invention,
To be conducive to using solution film forming, again through heating or ultraviolet light shine under be chemically crosslinked into it is insoluble melt film, realize connect
Continuous multilayer makes low cost, large-area OLEDs device.In one case, light layer main body in described Organic Light Emitting Diode
Material contains 2 crosslinkable groups trifluoro vinyls, with following structural formula（II）：
In the case of another kind, luminescent layer material of main part has following structural formula in described Organic Light Emitting Diode（III）：
In this patent category, luminescent layer material of main part contains crosslinkable groups acrylate in described Organic Light Emitting Diode
Base, with following structural formula（IV）：
Under scope, luminescent layer material of main part also contains crosslinkable groups styrene in described Organic Light Emitting Diode
Base, with following structural formula：
。
Y is C or N in II～V structural formulas；Ar1For aromatic ring of H, D, F, one carbon atom less than 18, carbon atom is less than 18
Heteroaromatic, a carbon atom condenses heteroaromatic less than 18；Ar2-3For H, aromatic ring of the carbon atom less than 18 a, carbon atom is less than
18 heteroaromatic a, carbon atom condenses heteroaromatic less than 18.
The category according to this patent, has various in the described organic semiconductor compound principle with crosslinked group
Various combination, wherein structure is comprising such as table 3 below structure：
Table 3：Material of main part with crosslinked group
。
Luminescent layer material of main part is soluble in usual solvents, such as dimethylbenzene, 1,2- dichloro in above-mentioned Organic Light Emitting Diode
Ethane, methyl phenyl ethers anisole etc., are easy to form film by spin coating, solution inkjet printing or printing etc..Shine lower in ultraviolet light or add
Hot temperature is more than 160oC, forms insoluble cross-linked network and ties film again.Such as structure（II）Can be formed not by following reaction
Dissolubility cross-linked network structure cross-linked structure II-X：
Structure（III）Cross-linked structure III-X can be formed by following reaction：
Structure（IV）Cross-linked structure IV-X can be formed by following reaction：
Structure（V）Cross-linked structure V-X can be formed by following reaction：
。
Can be prepared by various chemical reactions in any of the above compound principle, most common of which is secondary amine and halo virtue
Heterocycle, is obtained under palladium catalyst by Ullmann reactions or Buchwald- Hartwig reactions：
。
Organic Light Emitting Diode according to this patent scope, wherein in described Organic Light Emitting Diode in luminescent layer
Luminescent material can be an emission wavelength for 510-550nm green light material；Luminescent material can also be for an emission wavelength
The yellow light material of 551-580nm；Or for an emission wavelength for 581-630nm red light material.For obtain efficient green glow and
Ruddiness OLED, typically uses triplet state phosphorescent OLED, and emission layer therein contains phosphorescent light-emitting materials, such as Ir (MePPY)3For
Green glow, or Ir (Piq-Hex)3 As red dopant, lighted with 2 to 15% concentration（Weight）Material, is doped to a master
In body material.Typically carry out being mixed and made into OLED luminescent layers by common evaporation coating method using material of main part and doped luminescent material.
In recent years, it is more and more to also note that exploitation by being simply mixed solution, can obtain certain thickness using spin coating, printing or inkjet printing
The film of degree.The film obtained using solution in the case where ultraviolet light shines, or under heating state, such as larger than or equal to 160oC
Under, then after chemical reaction becomes insoluble insoluble network structure to cross-linking functional group, is on the one hand conducive to fixing dopant, increases
Plus dimensional stability of the film in temperature change, on the other hand when solution spin coating, printing or inkjet printing is further adopted
Still can be immune, to realize that Multifunctional layered solution manufacture OLED devices provide possibility.
In traditional Organic Light Emitting Diode chip, transparent conducting glass is typically with, or is coated with indium-tin-oxide
One layer of hole injection layer HIL is deposited with ITO, then one layer of hole transmission layer HTL, luminescent layer EML, electron transfer layer successively
ETL, electron injecting layer EIL, finally plus layer of metal, such as aluminum metal layer, as anode conducting and sealant.（Fig. 1）Work as ITO
Positive electricity is connect, aluminium connects negative electricity to after certain electric field, and hole is transmitted to EML from ITO Jing HIL injections and HTL, and electronics connects from aluminium
Transmit to EML after the EIL injections for connecing, through ETL.Electronics meets in EML, is combined into exciton with hole（Exciton),
Then part exciton gives off energy in light radiation form and returns to ground state.The wavelength of light radiation is by the luminescent dopant in EML layers
The energy gap of agent is determined.
What material of main part was commonly used is containing carbazole or arylamine structure class material.A kind of conventional material of main part is 4,4 '-N, N '-
Two carbazoles-biphenyl (CBP)：
CBP,
More senior has IPA-PCz and IPA-Ph-PCz：
。
IPA-PCz IPA-Ph-PCz
Organic Light Emitting Diode according to this patent scope, is characterized in that described organic material is higher sometimes for obtaining
Performance light emitting diode, in luminescent layer can also containing a co-host material for increasing electronics or Hole injection capacity, namely
Using hybrid agent material, wherein co-host material and the proportioning of primary body material are 5-45%.As green and red phosphorus
Light OLED, what material of main part of any triplet more than 2.4 eV all can be as the luminescent material OLED of the present invention should
With.Preferred co-host material has electron-donating material DBPP：,
Co-host material can also be following electronegativity material MCBP：。
To reach excellent phosphorescent devices performance, on anode, can an optional hole injection layer, such as blue or green blue（CuPc）Or
Other compounds containing fragrant ammonia (Appl.Phys.Lett., 69,2160 (1996), such as m-TDATA,
。
Similarly, between hole injection layer and emission layer EML, a hole transmission layer is also may be selected, such as use 4,4 '-it is bis-
[N- (1- naphthyls)-N- phenylaminos] biphenyl（α-NPD）,, or it is poly-（3,4- ethylene dioxy thiophenes
Fen）- polystyrolsulfon acid（PEDOT）（CAS：155090-83-8）：
。
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, and its structure is：
。
Between ETHL and negative electrode, electron injecting layer is also usually used.Electron injecting layer is typically the relatively low metal of work content
Lithium, LiF or its compound such as 8- hydroxyls lithium（Liq）：。
Therefore, OLED luminescent devices are the sandwich constructions of a complexity, 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 preferred gross thickness is 80-180 nanometers.
Using OLED luminescent devices, can be used for flat screen and show, such as Mobile phone screen, i-Pack screens, TV screen, computer screen etc..
Description of the drawings
Fig. 1 is organic LED structure schematic diagram.
Specific embodiment
It is understandable to enable the above objects, features and advantages of the present invention to become apparent from, with reference to examples of implementation to this
The specific embodiment of invention is described in detail.Elaborate many details in order to fully understand in the following description
The present invention.But the present invention can be to be much different from alternate manner described here implementing, and 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 present invention is not limited by following public specific embodiment
System.
Embodiment 1：Compound 1-2's is synthetically prepared：
According to chemical equation a, b, midbody compound 1-2A and 1-2B are prepared respectively, final reaction formula c is with 45% yield system
Standby compound 1-2.
Specific experiment scheme is as follows：
The preparation of intermediate 1-2A：By pyridine indoles (1.67g, 10mmol), 2- chloroquinolines (1.8g, 11mmol), Pd2
(dba)3(0.1g, 0.1mmol), sphos (0.123g, 0.3mmol), NaOBu (2.88g, 30mmol), 35mL toluene according to
In the there-necked flask of secondary addition 50mL, flow back overnight after displacement nitrogen three times, reaction is cooled to after room temperature after terminating, and is filtered, decompression
Concentration, gained solid is beaten again with petroleum ether, and final to obtain beige solid 2.27g, yield is 77%.
The preparation of intermediate 1-2B：During N- (2- quinoline) pyridine indoles (1g, 3.4mmol) is dissolved in into 20mLDMF, 3 are added
Drop acetic acid, adds NBS solids (0.67g, 3.75mmol, a small amount of multiple) under normal temperature, HPLC monitoring reactions, reaction is poured into after terminating
It is counter in water to be precipitated, filter, after filtration cakes torrefaction, ethyl acetate and petroleum ether mixed solvent are beaten to it, white admittedly final
Body 0.91g, yield is 71.5%.
The preparation of compound 1-2：By indoles quinoxaline (0.25g, 0.91mmol), the bromo- N- of 6- (2- quinoline) pyridine indoles
(0.44g, 1.18mmol), CuI (0.18g, 0.91mmol), cyclohexanediamine (0.21g, 1.82mmol), anhydrous K3PO4
(0.58g, 2.73mmol), DMAC 15mL are sequentially added in 100mL there-necked flasks, are stirred at 165 DEG C after displacement nitrogen three times
Overnight.Reactant liquor is down to after room temperature and is poured into frozen water, is filtered, and obtains brown solid, crosses silicagel column (with petroleum ether and ethyl acetate
For leacheate, its volume ratio is 5:1), final to obtain yellow solid 0.26g, yield is 45%.
Embodiment 2：Compound 2-2's is synthetically prepared：
Midbody compound 2-2A is prepared according to chemical equation d, final reaction formula e is with 52% yield prepare compound 2-2.
Specific experiment scheme is as follows：
The preparation of intermediate 2-2A：By 3- bromine carbazoles (2.7g, 10mmol), 2- chloroquinolines (1.63g, 11mmol), Pd2
(dba)3(0.1g, 0.1mmol), sphos (0.123g, 0.3mmol), NaOBu (2.88g, 30mmol), 35mL dimethylbenzene
In sequentially adding the two-mouth bottle of 50mL, flow back overnight after displacement nitrogen three times, reaction is cooled to room temperature after terminating, and filters, decompression
Concentration, crosses silicagel column and obtains white solid 2.12g, and yield is 57%.
The preparation of compound 2-2：By indoles quinoxaline (0.27g, 1.23mmol), N- (2- quinoline) -3- bromine carbazoles
(0.6g, 1.6mmol), CuI (0.23g, 1.23mmol), cyclohexanediamine (0.28g, 2.46mmol), anhydrous K3PO4
(0.79g, 3.69mmol), DMAC 20mL are sequentially added in 100mL there-necked flasks, are stirred at 165 DEG C after displacement nitrogen three times
Overnight.Reactant liquor is down to after room temperature and is poured into frozen water, is filtered, and obtains brown solid, crosses silicagel column (with petroleum ether and ethyl acetate
For leacheate, its volume ratio is 10:1), final to obtain yellow solid 0.37g, yield is 59%.
Embodiment 3：Compound 2-6's is synthetically prepared：
Midbody compound 2-6A is prepared according to chemical equation f, final reaction formula h is with 67% yield prepare compound 2-6.
The preparation of intermediate 2-6A：By the chloro- 4,6- diphenyl -1,3,5- of 3- bromopyridine indoles (12.3g, 50mmol), 2-
Triazine (13.2g, 50mmol), K2CO3(13.8g, 100mmol) 100ml DMF are sequentially added in the there-necked flask of 250mL, are put
Change and flow back after nitrogen three times overnight, reaction is cooled to room temperature after terminating, and reactant liquor is poured into the deionized water of 500mL and is stirred
30min, DCM extract organic phase, and DCM is used in concentration:PE=5:2 cross post, obtain white solid 20.1g, and yield is 84.5%.
The preparation of intermediate 2-6：By indoles quinoxaline (1g, 4.57mmol), the bromo- N- of 6- (triphen triazine between 4-) pyridine
Indoles (2.8g, 5.94mmol), CuI (0.87g, 4.57mmol), cyclohexanediamine (1.04g, 9.14mmol), anhydrous K 3PO4
(2.9g, 13.71mmol), DMAC 20mL are sequentially added in 100mL there-necked flasks, are stirred at 165 DEG C after displacement nitrogen three times
Overnight.During reactant liquor cooling is fallen back, filter, obtain dark brown solid, (leacheate volume ratio is PE to cross silicagel column:EA:
DCM=10:1) yellow solid 1.87g yields, are obtained for 67%.
Similarly, the synthesis principles of chemistry according to more than, under without prejudice to scope, have synthesized following each material of main part
Compound, concrete listed compound demonstrates the fragment that molecular weight and molecule have by mass spectrum, is specifically shown in table 4 below：
Table 4：Compound synthesis and sign
The Gauss quantum chemistry calculation of embodiment 4 can band HOMO LUMO results
Show from upper table result of calculation, compound 2-2 and compound 1-2 have similar HOMO lumo energy, that is to say, that
2 kinds of compounds have similar acquisition hole, electronic capability.However, comparing result it can also be seen that, the chemical combination with pyridine indoles
The HOMO electron cloud localities of thing 1-2 are bigger, are conducive to the transmission in hole, obtain performance improvement.
Embodiment 5 is deposited with OLED application example：
Evaporation OLED is made：In a base vacuum up to 10-5In the Multisource evaporation OLED Preparation equipments of handkerchief, using as follows
Device mechanism：ITO/mTDATA（100Å）/NPD(400 Å)/Host:Light-emitting dopant 10%（300 Å ）/TPBi（300
Å）/LiF（10 Å）/Al .
Using different Host OLED luminescent devices to compare.The vacuum moulding machine speed of wherein each organic layer and electrode
Spend and be listed in table 5 in the time.
The known material of main part of contrast：
Material of main part as a example by the explanation the compounds of this invention of table 5 is applied to OLED luminescent devices (nm of emission wavelength 620) doping
With luminescent properties are obviously improved, with comparative device A, B is compared illuminating OLED, with higher luminous efficiency LE（Lifted high
Up to 10%）, particularly speed up aging life-span LT90% and extend more than 50%.After using co-host material, such as device 11,12, accelerate
Aging life-span LT90% extends more.
Table 5：Vacuum evaporation OLED device performances (nits of room temperature@1000)
。
The solution of embodiment 6 makes OLED：
On an electro-conductive glass ITO surfaces, after solvent, plasma cleaning, solution spin coating PEDOT conducting polymers are used as sky
Cave implanted layer, using poly-（The heptane fluorenes of triphenylamine -9.9- two）PTW solution spin-coating film as hole transmission layer, then using 2%
Material of main part/light-emitting dopant green glow Ir (Me-PPY）3Or ruddiness Ir (piq-hex)3(weight of doping content 8%) mixed solution
After spin coating, through heated under nitrogen to 160oC is processed 30 minutes so as to which film cannot not become moltenly insoluble；Secondly solution spin coating is used
One layer of TPBi（300 Å）, finally in a base vacuum up to 10-5In the Multisource evaporation OLED Preparation equipments of handkerchief, evaporation electronics note
Enter a layer LiF（10 Å）/ Al100, prepares OLED device ITO/PEDOT/PTW/Host:5% light-emitting dopant/TPBi/LiF/
Al。
Table 6：Solution spin coating OLED device performances (nits of room temperature@1000)
Comparative device C shows similar material of main part with 1 and device D with 2, using the solution spin coating OLED devices of cross-linking material of main part
Part 1 and 2 has higher current efficiency LE and longer device lifetime.
The material of main part better to obtain performance indicated above, the key with indoles quinoxaline as substrate, on its N atom
Carbazole or pyridine indoles are connect to inhale electrfic centre, a nitrogenous heteroaromatic is re-introduced into and has been synthesized a series of material of main parts, OLED can be obtained
It is obviously improved in performance.Additionally, the miscellaneous fusion ring of a virtue containing cross-linking reactive group that is connected on indoles quinoxaline N atoms, has
Beneficial to further being made using solution film forming, obtain through crosslinking and do not melt insoluble stabilized illumination layer, improve device light emitting efficiency with
In the life-span, facilitate implementation continuous low cost solution spin coating, inkjet printing multilayer OLED light emitting display.
The above, is only presently preferred embodiments of the present invention, and any pro forma restriction is not made to the present invention.Appoint
What those of ordinary skill in the art, under without departing from technical solution of the present invention ambit, all using the skill of the disclosure above
Art content makes many possible variations and modification, or the Equivalent embodiments for being revised as equivalent variations to inventive technique scheme.Cause
This, every content without departing from technical solution of the present invention, according to the technical spirit of the present invention to made for any of the above embodiments any
Simple modification, equivalent variations and modification, still fall within the protection domain of technical solution of the present invention.
Claims (10)
1. a kind of Organic Light Emitting Diode, is characterized in that described Organic Light Emitting Diode is made up of following part：
（a）One negative electrode,
（b）One anode,
（c）One sandwich organic semiconductor luminescent layer between negative electrode and anode, the luminescent layer includes a material of main part and
Phosphor dopant, material of main part therein has following general structure：
It is characterized in that Y is C or N in described compound；
It is characterized in that Ar in described compound1For H, D, F, one carbon atom less than 18 aromatic ring, carbon atom less than 18 it is fragrant miscellaneous
Ring a, carbon atom condenses heteroaromatic less than 18；
It is characterized in that Ar2-3For H, aromatic ring of the carbon atom less than 18, heteroaromatic of the carbon atom less than 18 a, carbon atom is little
Heteroaromatic is condensed in 18.
2. Organic Light Emitting Diode according to claim 1, is characterized in that luminescent layer in described Organic Light Emitting Diode
Ar in material of main part2-3The unit of at least one crosslinked group is connected with, described crosslinked group is selected from vinyl, acrylic acid
Fat or trifluoro vinyl.
3. Organic Light Emitting Diode according to claim 2, is characterized in that luminescent layer in described Organic Light Emitting Diode
Material of main part has following structural formula：
Or
Or
Or。
4. Organic Light Emitting Diode according to claim 2, is characterized in that luminescent layer in described Organic Light Emitting Diode
Material of main part is more than 160 DEG C in heating-up temperature, forms insoluble cross-linked network structure：
Or：
Or：
。
5. Organic Light Emitting Diode according to claim 1, is characterized in that luminescent layer in described Organic Light Emitting Diode
Material of main part has following structural formula：
。
6. Organic Light Emitting Diode according to claim 2, is characterized in that luminescent layer in described Organic Light Emitting Diode
Material of main part has following structural formula：
。
7. Organic Light Emitting Diode according to claim 1, is characterized in that luminescent layer in described Organic Light Emitting Diode
In luminescent material be an emission wavelength be 510-550nm green light material.
8. Organic Light Emitting Diode according to claim 1, is characterized in that luminescent layer in described Organic Light Emitting Diode
In luminescent material be an emission wavelength be 551-580nm yellow light material.
9. Organic Light Emitting Diode according to claim 1, is characterized in that luminescent layer in described Organic Light Emitting Diode
In luminescent material be an emission wavelength be 581-630nm red light material.
10. Organic Light Emitting Diode according to claim 1, is characterized in that luminescent layer in described Organic Light Emitting Diode
In containing a co-host material for increasing electronics or Hole injection capacity, have confession comprising electron-donating material co-host material
Electric material DBPP or electronegativity co-host material MCBP：
。
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