CN106816544A - 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
- Publication number
- CN106816544A CN106816544A CN201710045292.4A CN201710045292A CN106816544A CN 106816544 A CN106816544 A CN 106816544A CN 201710045292 A CN201710045292 A CN 201710045292A CN 106816544 A CN106816544 A CN 106816544A
- Authority
- CN
- China
- Prior art keywords
- light emitting
- emitting diode
- organic light
- carbon atom
- less
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
A kind of Organic Light Emitting Diode, it is characterized in that described Organic Light Emitting Diode is by a negative electrode, an organic semiconductor layer between anode and negative electrode and anode is constituted, and an organic luminous layer is included wherein in organic semiconductor layer, containing a cross-linking bipolarity organic semiconductor compound, its formula is：
Description
Technical field
The present invention relates to organic semiconductor organic luminescent device application, a kind of especially 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, 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.Then, KodaK public affairs in 1987
C. Tang of department etc. have invented organic molecule light emitting diode（OLED）, and nineteen ninety Cambridge University R. Friend and A.
Holmes has invented polymer LED P-OLED, and S. Forrest in 1998 and M. Thomson have invented efficiency
Phosphorescent LED P HOLED higher.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, the requirement of organic photoelectric semiconductor has：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 contain 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 are 3 ~ 4 times of fluorescence OLED material, therefore decrease generation
Heat, increase the competitiveness of OLED display boards.This point provides and generally OLED show 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, 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 is shifted（MLCT）As 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, hole, negative electrode injection electronics, respectively through electron transfer layer and sky to be injected from anode
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 enters 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 influenceed 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 for launching blue light has following structural formula：
Main part 4 therein, 6- difluoro-benzene yl pyridines dominate glow color.The three of transmitting feux rouges（Octyl quinoline）Iridium
（Ⅲ）Coordinate complex compound, with 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 generally 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 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 occupying 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 one as object dopant by a small amount of luminescent material to have the semiconductor of more high level
Material of main part（Or bulk material Host material）Middle composition.Recent study shows, for same luminescent material or one
Colour light emitting device is planted, the difference of material of main part can cause different device light emitting efficiency and working lives.Therefore, develop new
Material of main part is always the important topic for influenceing 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, there is 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 with triphenylene using pyridine.
A. Dyatkin (US 2012/0256169) discloses the bipolarity master being made up 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 with pyridine indoles using carbazole
Material of main part.Lee. Beom Seong (WO 2015/ 2015098062) are disclosed and are made up 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, is conducive to improvement charge balance to inject and stability of photoluminescence, solution preparation OLED devices, acquisition 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
Described Organic Light Emitting Diode by partly constituting as follows：
(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 one
Phosphor dopant, material of main part therein has following general structure：
Y is C or N in described compound；Ar1It is aromatic ring of H, D, F, one carbon atom less than 18, virtue of the carbon atom less than 18
Heterocycle；One carbon atom condenses heteroaromatic less than 18；Ar2-3It is aromatic ring of H, F, one carbon atom less than 18, a carbon atom is less than 18
Heteroaromatic, a carbon atom condenses heteroaromatic less than 18；It is characterized in that Ar2-3It is connected with the list of at least one crosslinked group
Unit, described crosslinked group is 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 to following comprising vinyl on phenyl ring（A）, acrylic（B）And trifluoro vinyl（C）：
,
Above group can reach affiliated effect by chemical bonding in the host compound of invention in principle.
In the case of one kind, luminescent layer material of main part contains crosslinkable groups trifluoro vinyl in described Organic Light Emitting Diode, has
Following structural formula（II）：
In another case, 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 styrene in described Organic Light Emitting Diode
Base, with following structural formula：
Under scope, luminescent layer material of main part also contains crosslinkable groups acrylic acid in described Organic Light Emitting Diode
Ester group, with following structural formula：
Y is C or N in wherein described compound；Ar1It is aromatic ring of H, D, F, one carbon atom less than 18, carbon atom is less than 18
Heteroaromatic；One carbon atom condenses heteroaromatic less than 18；
Ar2-3It is aromatic ring of H, F, one carbon atom less than 18, heteroaromatic of the carbon atom less than 18 a, carbon atom is thick less than 18
Close heteroaromatic.
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 160oUnder C, insoluble cross-linked network structure film is formed again.Such as structure（II）Can be by following reaction
Form insoluble cross-linked network 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：
。
In a variety of textural associations, there are various different groups in described organic semiconductor compound principle
Close, wherein comprising following compound：
。
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 reacted under palladium catalyst and obtained by Ullmann reactions or Buchwald- Hartwig.In the case of one kind, benzo
Carbazole radical compound can be by being synthesized as follows：
。
For MOLECULE DESIGN purpose, consciously from electrophilicity heteroaromatic（acceptor）With electron-donating hole transport virtue
Heterocycle（donor）It is combined into molecule so that described compound has D-A bipolar structures.
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 be 510-550nm green light material；Luminescent material can also be that an emission wavelength is
The yellow light material of 551-580nm；Or for an emission wavelength is the red light material of 581-630nm.For obtain efficient green glow and
Feux rouges OLED, typically uses triplet state phosphorescent OLED.Emission layer therein contains phosphorescent light-emitting materials, such as Ir (MePPY)3
It is green glow, or Ir (Piq-Hex)3 As red dopant, lighted 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 for being obtained then shows to suffer erosion when solution molding is continuing with, it is unfavorable with it is acquired
The excellent solution of energy is made OLED.But using under invention technology, made film in the case where ultraviolet light shines, or
Under heating state, such as larger than or equal to 160oC under, then after chemical reaction turns into insoluble insoluble net to cross-linking functional group
Network structure, is on the one hand conducive to fixing dopant, increases dimensional stability of the film in temperature change, is on the other hand entering one
Can be from solvent corrosive effect, to realize that Multifunctional layered solution manufactures OLED when step is using solution spin coating, printing or inkjet printing
Device is provided may.
Organic Light Emitting Diode according to this patent scope, it is characterized in that can also contain in described 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
Material is 5-45% with the proportioning of primary body material.Used as green and red phosphorescent OLED, any triplet is more than 2.4
The material of main part of eV all can be used as the application of luminescent material OLED of the invention.Preferred co-host material has electron-donating material
Material DBPP：
DBPP
Co-host material can also be following electronegativity material MCBP：
。
In traditional Organic Light Emitting Diode chip, transparent conducting glass is typically with, or be coated with indium-tin-oxide
On ITO be deposited with one layer of hole injection layer HIL, then successively its surface be made one layer of hole transmission layer HTL, luminescent layer EML,
Electron transfer layer ETL, electron injecting layer EIL, are finally deposited with 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 passes through from ITO
HIL is injected and HTL is transmitted to EML, and is transmitted to EML after the EIL injections that electronics is connected from aluminium, by ETL.Electronics and hole
Met in EML, be combined into exciton（Exciton), then part exciton gives off energy in light radiation form 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 glow, gold-tinted etc..
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
To reach excellent phosphorescent devices performance, on anode, can an optional hole injection layer, such as blue or green blue（CuPc）Or other
Containing fragrant ammonia compound (Appl.Phys.Lett., 69,2160 (1996), such as m-TDATA,
。
Similarly, between hole injection layer and emission layer EML, a hole transmission layer also may be selected, such as use 4,4 '-
Double [N- (1- naphthyls)-N- phenylaminos] biphenyl（α-NPD）
,
Or it is poly-（3,4-rthylene dioxythiophene）/ polystyrolsulfon acid（PEDOT）（CAS：155090-83-8）：
。
It is the injection in balance electronic and hole, improves luminous efficiency, 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, also usually using electron injecting layer.Electron injecting layer is typically the relatively low metal Lithium of work content,
LiF or its organic 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 preferably 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 is empty
Intend helmet AR to show.
Brief description of the drawings
Fig. 1 is organic LED structure schematic diagram.
Specific embodiment
To enable the above objects, features and advantages of the present invention more obvious understandable, 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 implemented with being much different from other manner described here, 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 it is synthetically prepared：
Following each cross-linking material of main part compound is prepared according to chemical reaction formula principle respectively, listed compound passes through
Mass spectrum demonstrates the fragment that molecular weight and molecule have, and is specifically shown in table 1 below.
The synthesis of the compound of table 1 and sign
。
The device application example of embodiment 2.：
On an electro-conductive glass ITO surfaces, by 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）Solution spin-coating film as hole transmission layer, then using 2% master
Body material/light-emitting dopant green glow Ir (Me-PPY)3Or feux rouges Ir (piq-hex)3(weight of doping concentration 8%) mixed solution spin coating
Afterwards, by heated under nitrogen to 160oC is processed 30 minutes, and turning into its film do not melt insoluble；Secondly one layer of solution spin coating is used
TPBi（300 Å）, finally in a base vacuum up to 10-5In the Multisource evaporation OLED Preparation equipments of handkerchief, electron injection is deposited with
Layer LiF（10 Å）/ Al100, prepares OLED devices.Using different material of main part OLED luminescent devices to do ratio
Compared with.Contrast material of main part：
All OLED devices being made test I-V-L and accelerated aging test by being carried out after encapsulation, as a result summarize such as table 2.
Table 2：OLED device performances (nits of room temperature@1000)
。
Material of main part as a example by the explanation the compounds of this invention of table 2 is applied to known green glow（The nm of emission wavelength 520）, feux rouges
(nm of emission wavelength 620) adulterates illuminating OLED with luminescent properties are obviously improved, than corresponding to existing material of main part PH
Comparative device A, B that is made of solution, with luminous efficiency LE higher（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 mixing of co-host material prepared device 18,19 comparator devices 16, current efficiency and longer aging longevity with lifting
Life.
It is indicated above, one is connected on double electrical benzo carbazole N atoms containing the cross-linking reactive group miscellaneous fusion ring of virtue, have
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 obtaining low cost, the OLED of large area solution manufacture
Device.Conversely, the general material of main part without crosslinkable groups, then when solution film forming is further used, because its surface is easy to
Corroded by solvent and make device performance degradation.
The above, is only presently preferred embodiments of the present invention, and any formal limitation is not made to the present invention.Appoint
What those of ordinary skill in the art, in the case where technical solution of the present invention ambit is not departed from, 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 technical solution of the present invention.
Therefore, every content without departing from technical solution of the present invention, according to technical spirit of the invention 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)
1. a kind of Organic Light Emitting Diode, it is characterized in that described Organic Light Emitting Diode by partly constituting as follows：
（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 one
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 compound1It is aromatic ring of H, D, F, one carbon atom less than 18, carbon atom is fragrant miscellaneous less than 18
Ring；One carbon atom condenses heteroaromatic less than 18；
It is characterized in that Ar2-3It is aromatic ring of H, F, one carbon atom less than 18, heteroaromatic of the carbon atom less than 18, a carbon atom
Heteroaromatic is condensed less than 18；
It is characterized in that Ar2-3The unit of at least one crosslinked group is connected with, described crosslinked group is selected from vinyl, acrylic acid
Fat or trifluoro vinyl.
2. Organic Light Emitting Diode according to claim 1, it is characterized in that luminescent layer in described Organic Light Emitting Diode
Material of main part has following structural formula：
Or：
Or：
Or：
It is characterized in that Y is C or N in described compound；
It is characterized in that Ar in described compound1It is aromatic ring of H, D, F, one carbon atom less than 18, carbon atom is fragrant miscellaneous less than 18
Ring；One carbon atom condenses heteroaromatic less than 18；
It is characterized in that Ar2-3It is aromatic ring of H, F, one carbon atom less than 18, heteroaromatic of the carbon atom less than 18, a carbon atom
Heteroaromatic is condensed less than 18.
3. Organic Light Emitting Diode according to claim 2, it is characterized in that luminescent layer in described Organic Light Emitting Diode
Material of main part is more than 160 in heating-up temperatureoC, forms insoluble cross-linked network structure：
Or：
Or：
Or：。
4. Organic Light Emitting Diode according to claim 1, it is characterized in that luminescent layer in described Organic Light Emitting Diode
Material of main part has following structural formula：
。
5. Organic Light Emitting Diode according to claim 1, it 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.
6. Organic Light Emitting Diode according to claim 1, it 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.
7. Organic Light Emitting Diode according to claim 1, it 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.
8. Organic Light Emitting Diode according to claim 1, it 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：
。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710045292.4A CN106816544B (en) | 2017-01-22 | 2017-01-22 | A kind of cross-linking bipolarity organic semiconductor and its Organic Light Emitting Diode application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710045292.4A CN106816544B (en) | 2017-01-22 | 2017-01-22 | A kind of cross-linking bipolarity organic semiconductor and its Organic Light Emitting Diode application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106816544A true CN106816544A (en) | 2017-06-09 |
| CN106816544B CN106816544B (en) | 2018-04-24 |
Family
ID=59112507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710045292.4A Active CN106816544B (en) | 2017-01-22 | 2017-01-22 | A kind of cross-linking bipolarity organic semiconductor and its Organic Light Emitting Diode application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106816544B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111180602A (en) * | 2020-01-06 | 2020-05-19 | 深圳市华星光电半导体显示技术有限公司 | Display panel and preparation method thereof |
| WO2021120299A1 (en) * | 2019-12-16 | 2021-06-24 | 深圳市华星光电半导体显示技术有限公司 | Ink composition for ink-jet printing of organic light emitting diode and preparation method therefor |
| EP3872882A4 (en) * | 2018-10-25 | 2022-08-17 | Sumitomo Chemical Company Limited | Light-emitting element |
| EP3872883A4 (en) * | 2018-10-25 | 2022-08-17 | Sumitomo Chemical Company Limited | Light-emitting element |
| US11441045B2 (en) | 2019-12-16 | 2022-09-13 | Shenzhen China Star Optoelectronics Semiconductor Display Technology Co., Ltd. | Ink composition for inkjet printing organic light-emitting diodes and method of manufacturing the same |
| 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 |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3872882A4 (en) * | 2018-10-25 | 2022-08-17 | Sumitomo Chemical Company Limited | Light-emitting element |
| EP3872883A4 (en) * | 2018-10-25 | 2022-08-17 | Sumitomo Chemical Company Limited | Light-emitting element |
| WO2021120299A1 (en) * | 2019-12-16 | 2021-06-24 | 深圳市华星光电半导体显示技术有限公司 | Ink composition for ink-jet printing of organic light emitting diode and preparation method therefor |
| US11441045B2 (en) | 2019-12-16 | 2022-09-13 | Shenzhen China Star Optoelectronics Semiconductor Display Technology Co., Ltd. | Ink composition for inkjet printing organic light-emitting diodes and method of manufacturing the same |
| CN111180602A (en) * | 2020-01-06 | 2020-05-19 | 深圳市华星光电半导体显示技术有限公司 | Display panel and preparation method thereof |
| CN111180602B (en) * | 2020-01-06 | 2022-04-05 | 深圳市华星光电半导体显示技术有限公司 | Display panel and preparation method thereof |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106816544B (en) | 2018-04-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106831884A (en) | Organic metal iridium complex and its organic electroluminescence device application | |
| CN106816544B (en) | A kind of cross-linking bipolarity organic semiconductor and its Organic Light Emitting Diode application | |
| CN106611823B (en) | A kind of cross-linking organic semiconductor material of main part and its Organic Light Emitting Diode application | |
| CN102044634B (en) | Organic light-emitting diode and method of manufacturing the same | |
| CN106977520B (en) | One kind organic semiconducting materials containing indolocarbazole and its organic luminescent device application | |
| CN1711652B (en) | Structure and method of fabricating organic devices | |
| CN107221611B (en) | A kind of stable easy processing organic semiconducting materials and its organic luminescent device application | |
| CN107431140B (en) | Organic electroluminescent device | |
| CN102651454B (en) | Electroluminescent device, display device and preparation method of electroluminescent device | |
| CN106800555A (en) | A kind of organic semiconductor material of main part and its Organic Light Emitting Diode application | |
| CN106977527B (en) | A kind of organic semiconductor compound and the organic electroluminescence device using the compound | |
| CN104557440A (en) | Substituted benzophenanthrene derivative organic light emitting diode material | |
| CN105111243A (en) | Light-emitting metal iridium complex and organic electroluminescence device prepared from same | |
| CN106165140B (en) | Organic luminescent device | |
| CN113135945A (en) | Organic boron semiconductor material and OLED device application | |
| CN102144015A (en) | Pyrrole compounds and organic photoelectric device including the same | |
| CN106749341B (en) | Balancing charge injects organic semiconductor and its Organic Light Emitting Diode application | |
| CN104447505B (en) | Stable organic light emitting diode | |
| CN106654035B (en) | A kind of organic semiconductor material of main part and its Organic Light Emitting Diode application | |
| CN103956436B (en) | A kind of organic semiconductor hole transferring material | |
| CN106784359B (en) | Cross-linking balancing charge injection organic semiconductor and its Organic Light Emitting Diode application | |
| CN106684253B (en) | A kind of indoles quinoxaline Organic Light Emitting Diode material | |
| KR102128299B1 (en) | Novel organic electroluminescent compound, organic electroluminescent device including the same and electric apparatus | |
| CN106654036B (en) | A kind of bipolarity organic semiconductor and its Organic Light Emitting Diode application | |
| CN108707168B (en) | Sulfone ring-containing metal iridium complex and organic electroluminescent device based on complex |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |