CN106816544B - A kind of cross-linking bipolarity organic semiconductor and its Organic Light Emitting Diode application - Google Patents
A kind of cross-linking bipolarity organic semiconductor and its Organic Light Emitting Diode application 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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- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
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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
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 a cross-linking bipolarity organic semiconductor compound, its general formula is：It is characterized in that it is connected one on bipolarity benzo carbazole N atoms containing the miscellaneous fusion ring of cross-linking reactive group virtue, be conducive to improve charge balance injection and stability of photoluminescence, easy to be further made of solution film forming, obtained by crosslinking and do not melt insoluble stabilized illumination layer, realize continuous inexpensive solution spin coating, inkjet printing multilayer OLED light emitting displays.
Description
Technical field
The present invention relates to organic semiconductor in the application of organic luminescent device, especially a kind of cross-linking organic semiconductor material
Material, 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：1. height shines
Efficiency；2. excellent electronics and hole stability；3. suitable glow color；4. excellent film forming processability.In principle,
Most of conjugacy organic molecule（Include star beam）, conjugacy polymer, and contain the organic heavy of conjugacy chromophore ligand
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, and its derivative I r (MePPY)3It 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：
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 master 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.Kim.Bok Yeong (WO 2012/2012081539) disclose 11H- benzos [C] carbazole and are connected with carbazole
Bulk material.Kim. Jung Geun (WO 2014/ 2014067263) disclose what is be connected using carbazole with pyridine indoles
Material of main part.Lee. Beom Seong (WO 2015/ 2015098062) are disclosed is made of carbazole and dibenzothiophenes
Bipolar host material, but these materials are due to the limitation in structure, it is difficult to prepare OLED devices as solution film forming.
The content of the invention
The present invention provides a kind of organic compound semiconductor, one can be handed over by being connected on the N atoms of bipolarity benzo carbazole
The miscellaneous fusion ring of biaryl, be conducive to improve charge balance injection and stability of photoluminescence, solution prepare OLED devices, obtain high stable,
High efficiency and potential low cost, the luminescent device OLED of large area.A kind of Organic Light Emitting Diode is applied particularly to, 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 main body material
Material compound and a phosphor dopant, material of main part compound therein have following general structure：
Y is C or N in the material of main part compound；Ar1It is less than 18 aromatic ring for H, D, F, one carbon atom, carbon is former
Son is less than 18 heteroaromatic；One carbon atom is less than 18 fusion heteroaromatic；Ar2、Ar3It is less than 18 aromatic ring for H, F, one carbon atom,
One carbon atom is less than 18 heteroaromatic, and a carbon atom is less than 18 fusion heteroaromatic；It is characterized in that Ar2、Ar3It is connected with least 1
The unit of a crosslinked group, the crosslinked group are selected from vinyl, acrylate or trifluoro vinyl.
There are many chemical groups all to possess crosslinking function, wherein be typically included in heating or ultraviolet light shine under crosslinking
Group, row are such as connected on phenyl ring and include vinyl as follows（A）, acrylic（B）And trifluoro vinyl（C）：
Above group can reach affiliated effect by chemical bonding in the host compound of invention in principle
Fruit.In the case of one kind, luminescent layer material of main part compound contains crosslinkable groups trifluoro second in the Organic Light Emitting Diode
Alkenyl, has following structural formula（II）：
In another case, luminescent layer material of main part compound has following structural formula in the Organic Light Emitting Diode
（III）：
In this patent category, luminescent layer material of main part compound contains cross-linking base in the Organic Light Emitting Diode
Group's styryl, has following structural formula：
Under scope, luminescent layer material of main part compound is also containing cross-linking in the Organic Light Emitting Diode
Group is acrylate-based, has following structural formula：
Y is C or N in the wherein described compound；Ar1It is less than 18 aromatic ring for H, D, F, one carbon atom, carbon atom is small
In 18 heteroaromatic；One carbon atom is less than 18 fusion heteroaromatic；
Ar2、Ar3It is less than 18 aromatic ring for H, F, one carbon atom, a carbon atom is less than 18 heteroaromatic, and a carbon atom is less than
18 fusion heteroaromatic.
Luminescent layer material of main part compound is soluble in usual solvents, such as dimethylbenzene in above-mentioned Organic Light Emitting Diode, and 1,
2- dichloroethanes, methyl phenyl ethers anisole etc., easy to form film by spin coating, solution inkjet printing or printing etc..Shone in ultraviolet light
Lower or heating-up temperature is more than 160oUnder C, and form insoluble cross-linked network structure film.Such as structure（II）Can be by such as
Lower reaction forms insoluble cross-linked network structure II-X：
Structure（III）Cross-linked structure III-X can be formed by reacting as follows：
Structure（IV）Cross-linked structure IV-X can be formed by reacting as follows：
Structure（V）Cross-linked structure V-X can be formed by reacting as follows：
In the combination of a variety of structures, have in the organic semiconductor material of main part compound principle various
Various combination, wherein including following compound：
It can be prepared in any of the above compound principle by a variety of chemical reactions, most common of which is secondary amine and halo virtue
Heterocycle, is obtained under palladium catalyst by Ullmann reactions or Buchwald- Hartwig reactions.In the case of one kind, benzo
Carbazole radical compound can be by reacting synthesis as follows：
For MOLECULE DESIGN purpose, electrophilicity heteroaromatic is selected consciously（acceptor）With electron-donating hole transport virtue
Heterocycle（donor）It is combined into molecule so that the compound has D-A bipolar structures.
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 layer therein contains phosphorescent light-emitting materials, such as Ir (MePPY)3
For green light, or Ir (Piq-Hex)3 As red dopant, shone with 2 to 15% concentration（Weight）Material, is doped to one
In material of main part.Using material of main part and doped luminescent material mixed solution, spin coating, printing or inkjet printing can be used to obtain
Certain thickness film.The film obtained then shows to suffer erosion when being continuing with solution molding, it is unfavorable with it is acquired
OLED device is made in the excellent solution of energy.But using under invention technology, made film in the case where ultraviolet light shines, or
Under heating state, such as larger than or equal under 160oC, then after chemical reaction becomes insoluble insoluble net to cross-linking functional group
Network structure, is on the one hand conducive to the dimensional stability of fixed dopant, increase film in temperature change, on the other hand into one
Walking can be from solvent corrosive effect, to realize that Multifunctional layered solution manufactures OLED when using solution spin coating, printing or inkjet printing
Device provides may.
According to the Organic Light Emitting Diode described in this patent scope, it is characterized in that can also contain in the organic luminous layer
There is the co-host material of an increase electronics or Hole injection capacity, namely use hybrid agent material, wherein co-host material
The proportioning of material and primary body material is 5-45%.As green and red phosphorescent OLED, any triplet is more than 2.4
The material of main part of eV all can be as the application of the luminescent material OLED of the present invention.Preferable co-host material has electron-donating material
Expect 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
On ITO be deposited one layer of hole injection layer HIL, be then made successively on its surface one layer of hole transmission layer HTL, luminescent layer EML,
Electron transfer layer ETL, electron injecting layer EIL, are finally deposited one layer of metal, such as aluminum metal layer, as anode conducting and sealant,
Specific multilayer OLED structure is as shown in Fig. 1.When ITO connects positive electricity, after aluminium connection negative electricity applies certain electric field, hole is passed through from ITO
HIL injects and HTL is transmitted to EML, and electronics is transmitted to EML after the EIL injections that aluminium connects, by ETL.Electronics and hole
Meet in EML, be combined into exciton（Exciton), then part exciton is given off energy in the form of light radiation and returns to base
State.The wavelength of light radiation determines by the energy gap of the light-emitting dopant in EML layers, can be feux rouges, green light, yellow light etc..
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)：
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, a hole transmission layer also may be selected, such as using 4,4 '-
Double [N- (1- naphthyls)-N- phenylaminos] biphenyl（α-NPD）
It is or poly-（3,4-rthylene dioxythiophene）/ 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, example are 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, LiF or its organic 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, it is empty
Intend helmet AR to show.
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：
Following each cross-linking material of main part compound, listed compound are prepared according to chemical reaction general formula principle respectively
By mass spectrum demonstrate molecular weight and molecule possessed by fragment, be specifically shown in table 1 below.
Table 1：Compound synthesis and characterization
2. device application example of embodiment：
On an electro-conductive glass ITO surfaces, after solvent, plasma cleaning, solution spin coating PEDOT conducting polymers are made
For hole injection layer, using poly-（Two heptane fluorenes of triphenylamine -9.9-）Solution spin-coating film is as hole transmission layer, then using 2%
Material of main part/light-emitting dopant green light Ir (Me-PPY)3Or feux rouges Ir (piq-hex)3(8% weight of doping concentration) mixed solution
After spin coating, by heated under nitrogen to 160oC is handled 30 minutes, its film is become not molten 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 pa, electronics is deposited
Implanted layer LiF（10 Å）/ Al100, prepares OLED devices.Using different material of main part OLED luminescent devices so as to
Compare.Contrast material of main part：
OLED devices made of all carry out test I-V-L and accelerated aging test after encapsulation, as a result summarize such as table 2：
Table 2：OLED device performances (1000 nits of room temperature@)
Table 2 illustrates that the material of main part exemplified by the compounds of this invention is applied to known green light（520 nm of emission wavelength）, feux rouges
(620 nm of emission wavelength) doping illuminating OLED, which has, is obviously improved luminescent properties, than corresponding to existing material of main part PH
Solution made of comparative device A, B, have higher luminous efficiency LE（Lifting amplitude is more than 35%）, and driving voltage is more
It is low, accelerated life LT90%Extended for more than 50% time；Meanwhile compound of the invention, such as 3-3 and DBPP, MCBP
The prepared device 18 of co-host material mixing, 19 comparator devices 16, have the current efficiency of lifting and longer aging longevity
Life.
It is indicated above, electrically it is connected one on benzo carbazole N atoms containing the miscellaneous fusion ring of cross-linking reactive group virtue double, has
Beneficial to charge balance injection and stability of photoluminescence is improved, can especially obtain can after solution film forming by being chemically crosslinked luminescent layer,
Then solution film forming electron transfer layer ET can be continuously reused, is conducive to obtain low cost, the OLED of large area solution manufacture
Device.On the contrary, the general material of main part without crosslinkable groups, then when further using solution film forming, since its surface is easy to
It is subject to solvent to corrode and make device performance degradation.
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 (8)
- 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,One sandwich organic semiconductor luminescent layer between cathode and anode, the luminescent layer include a material of main part compound and One phosphor dopant, material of main part compound therein have following general structure：It is characterized in that Y is C or N in the compound；It is characterized in that Ar in the compound1It is less than 18 aromatic ring for H, D, F, one carbon atom, carbon atom is fragrant miscellaneous less than 18 Ring；One carbon atom is less than 18 fusion heteroaromatic；It is characterized in that Ar2、Ar3It is less than 18 aromatic ring for H, F, one carbon atom, a carbon atom is less than 18 heteroaromatic, and a carbon is former Son is less than 18 fusion heteroaromatic；It is characterized in that Ar2、Ar3The unit of at least one crosslinked group is connected with, the crosslinked group is selected from vinyl, propylene Sour fat or trifluoro vinyl.
- 2. Organic Light Emitting Diode according to claim 1, it is characterized in that luminescent layer in the Organic Light Emitting Diode Material of main part compound has following structural formula：OrOrOrIt is characterized in that Y is C or N in the compound；It is characterized in that Ar in the compound1It is less than 18 aromatic ring for H, D, F, one carbon atom, carbon atom is fragrant miscellaneous less than 18 Ring；One carbon atom is less than 18 fusion heteroaromatic；It is characterized in that Ar2、Ar3It is less than 18 aromatic ring for H, F, one carbon atom, a carbon atom is less than 18 heteroaromatic, and a carbon is former Son is less than 18 fusion heteroaromatic.
- 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 is more than 160 in heating-up temperatureoC, forms insoluble cross-linked network structure：OrOrOr（IV-X）。
- 4. Organic Light Emitting Diode according to claim 1, it is characterized in that luminescent layer in the Organic Light Emitting Diode Material of main part compound has following structural formula：。
- 5. Organic Light Emitting Diode according to 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.
- 6. Organic Light Emitting Diode according to 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.
- 7. Organic Light Emitting Diode according to 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.
- 8. Organic Light Emitting Diode according to 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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| CN115772341A (en) * | 2021-09-06 | 2023-03-10 | 牛津大学(苏州)科技有限公司 | Coating liquid for forming organic light-emitting layer or photosensitive layer, and method for producing same |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101220154A (en) * | 2008-01-31 | 2008-07-16 | 上海交通大学 | Crosslinked polyalcohol membrana body material, method for producing the same and process of using |
| CN102010499A (en) * | 2010-11-11 | 2011-04-13 | 常州大学 | Fluorene polymer with crosslinkable group, crosslinked film and preparation method thereof |
| CN103012173A (en) * | 2012-12-11 | 2013-04-03 | 京东方科技集团股份有限公司 | Crosslinkable compound, preparation method thereof and luminescent device made from crosslinkable compound |
| CN103682169A (en) * | 2013-12-19 | 2014-03-26 | 江西冠能光电材料有限公司 | Bipolar body material |
| KR20140120089A (en) * | 2013-04-02 | 2014-10-13 | 에스에프씨 주식회사 | An organoelectro luminescent compounds and organoelectro luminescent device using the same |
| KR20140125061A (en) * | 2013-04-18 | 2014-10-28 | (주)경인양행 | An organoelectro luminescent compound and an organoelectroluminescent device using the same |
| CN104364345A (en) * | 2012-06-13 | 2015-02-18 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same |
-
2017
- 2017-01-22 CN CN201710045292.4A patent/CN106816544B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101220154A (en) * | 2008-01-31 | 2008-07-16 | 上海交通大学 | Crosslinked polyalcohol membrana body material, method for producing the same and process of using |
| CN102010499A (en) * | 2010-11-11 | 2011-04-13 | 常州大学 | Fluorene polymer with crosslinkable group, crosslinked film and preparation method thereof |
| CN104364345A (en) * | 2012-06-13 | 2015-02-18 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same |
| CN103012173A (en) * | 2012-12-11 | 2013-04-03 | 京东方科技集团股份有限公司 | Crosslinkable compound, preparation method thereof and luminescent device made from crosslinkable compound |
| KR20140120089A (en) * | 2013-04-02 | 2014-10-13 | 에스에프씨 주식회사 | An organoelectro luminescent compounds and organoelectro luminescent device using the same |
| KR20140125061A (en) * | 2013-04-18 | 2014-10-28 | (주)경인양행 | An organoelectro luminescent compound and an organoelectroluminescent device using the same |
| CN103682169A (en) * | 2013-12-19 | 2014-03-26 | 江西冠能光电材料有限公司 | Bipolar body material |
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