CN106611823A - Crosslinkable organic semiconductor host material and organic light emitting diode application thereof - Google Patents

Crosslinkable organic semiconductor host material and organic light emitting diode application thereof Download PDF

Info

Publication number
CN106611823A
CN106611823A CN201710038622.7A CN201710038622A CN106611823A CN 106611823 A CN106611823 A CN 106611823A CN 201710038622 A CN201710038622 A CN 201710038622A CN 106611823 A CN106611823 A CN 106611823A
Authority
CN
China
Prior art keywords
light emitting
carbon atom
emitting diode
organic light
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
Application number
CN201710038622.7A
Other languages
Chinese (zh)
Other versions
CN106611823B (en
Inventor
李晓常
殷正凯
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
GUANMAT OPTOELECTRONIC MATERIALS (JIANGXI) Inc
Original Assignee
GUANMAT OPTOELECTRONIC MATERIALS (JIANGXI) Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by GUANMAT OPTOELECTRONIC MATERIALS (JIANGXI) Inc filed Critical GUANMAT OPTOELECTRONIC MATERIALS (JIANGXI) Inc
Priority to CN201710038622.7A priority Critical patent/CN106611823B/en
Publication of CN106611823A publication Critical patent/CN106611823A/en
Application granted granted Critical
Publication of CN106611823B publication Critical patent/CN106611823B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/615Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings

Landscapes

  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The invention provides an organic light emitting diode. The organic light emitting diode is characterized in that the organic light emitting diode is composed of a cathode, an anode, and an organic semiconductor layer between the cathode and the anode. The organic semiconductor layer comprises an organic light emitting layer containing a crosslinkable organic semiconductor host material, and the general formula is described in the description. The crosslinkable organic semiconductor host material is characterized in that a developed five-membered aromatic heterocycloalkenyl carbazole nitrogen atom is connected with a heterocyclic aromatic fused ring containing a crosslinkable reactive group. On the basis that charge balance injection and luminous stability are improved, solution film formation is conveniently carried out. The insoluble stable light emitting layer is acquired through cross-linking. A continuous low-cost solution spin coating and inkjet printing multi-layer OLED light emitting display is realized.

Description

A kind of cross-linking organic semiconductor material of main part and its Organic Light Emitting Diode application
Technical field
The present invention relates to application of the organic semiconductor in organic luminescent device, a kind of balance electricity of especially cross-linking reaction Lotus injects the organic semiconducting materials with transmission, can be applied to low cost, large area as material of main part by solution film forming Organic luminescent device, 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 conductivity 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 as 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 flat pannel display and illumination Apply, three scientists of Bai Chuan-Heeger-McDiamid obtained Nobel chemistry Prize in 2000 more.
Used as the Organic Light Emitting Diode of flat panel display of future generation, organic photoelectric quasiconductor 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 panels.This point provides and generally OLED is shown or illuminates that to surmount LCD aobvious Show and conventional light source possibility.Thus, phosphorescent OLED material has more or less been mixed 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, in high energy light according under(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, to inject hole, negative electrode injection electronics, respectively through electron transfer layer and sky from anode Layer is transferred in cave, while in the material of main part of emission layer, the minimum end that electronics is eventually entered in 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 excited 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 of existing many reports, is affected by heavy metal and is enhanced spin(-)orbit work 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, referred to as Ir (PPY)3, and its derivative I r (MePPY)3With structural formula it is:
,
The FirPic of transmitting blue light has following structural formula:
,
Main part 4 therein, 6- difluoro-benzene yl pyridines dominate glow color.The three of transmitting HONGGUANG(Octyl quinoline)Iridium (Ⅲ)Coordinate complex, 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 generally need to be added between luminescent layer and anode Layer, adds hole note and hole transmission layer 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)Aluminum(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 quasiconductor 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 Colour light emitting device is planted, the difference of material of main part can cause different device light emitting efficiencies and working life.Therefore, develop new Material of main part always affects the important topic of Organic Light Emitting Diode practical application.It is for ease of hole, the injection of electronics, preferable Material of main part should possess hole that is not only strong but also balancing and electron injection and transmittability.To reach this purpose, have many Improved material of main part appears in the newspapers.V. Adamocich (US 2006/0280965) discloses the sheet that carbazole is connected with triphenylene Body material.C. Adachi (WO 2012/114745) discloses the bipolar host material being connected with triphenylene using pyridine. A. Dyatkin (US 2012/0256169) discloses the bipolarity master being made up of benzothiophene, phenyl and indolepyridinium Body material.A.M.Parham has delivered bipolar host material(WO2013041176A):
,
But the OLED application of superperformance is not disclosed, especially such compound is only suitable for being deposited with into using traditional vacuum Film, is not suitable for preparing large area, low cost OLED luminescent devices using solution film forming.
The content of the invention
The present invention provides a kind of organic compound semiconductor, on the nitrogen-atoms of five Yuans heteroaromatic indeno carbazoles of a prosperity Connection one constructs a series of bipolar host material compounds containing the cross-linking reactive group miscellaneous fused rings of virtue, has concurrently good molten Insoluble, insoluble performance can be converted into again after solution performance and heating.Be conducive to acquisition can solution film forming then by chemical crosslinking, Increase the heat stability and anti-solvent ability of thin film, be easy to solution film forming be reused being crosslinked function layer surface, realize low Cost spin coating, inkjet printing obtain low cost and the large-area OLED brought by multilamellar solution film forming.It is applied particularly to A kind of Organic Light Emitting Diode, is characterized in that described Organic Light Emitting Diode is made up of following part:
(a), negative electrode
(b), an anode
(c), a 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 have following general structure:
,
It is characterized in that Z=O in described compound, S, S (O)2, C (R)2, Si(R)2, R is alkane of the carbon number less than 18 Base, aryl;
It is characterized in that X is a singly-bound in described compound, aromatic ring of the carbon atom less than 18, a carbon atom are less than 18 Heteroaromatic, thick and heteroaromatic of the carbon atom less than 18;
It is characterized in that Ar in described compound1For H, alkyl of the carbon atom less than 8, virtue of the carbon atom less than 18 Ring, heteroaromatic of the carbon atom less than 18, a carbon atom condense heteroaromatic less than 18;
It is characterized in that Y is C or N in described compound;
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 are little Heteroaromatic is condensed in 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, propylene Sour fat or trifluoro vinyl.
Have many chemical groups all to possess crosslinking function, wherein be typically included in heating or ultraviolet light shine under crosslinking Group, for example, be connected to following comprising vinyl on phenyl ring(A), acrylic(B), and trifluoro vinyl(C):
Above group can pass through host compound of the chemical bonding in invention in principle, reach affiliated effect Really.In the case of one kind, in described Organic Light Emitting Diode, luminescent layer material of main part contains crosslinkable groups trifluoro vinyl, tool There is following structural formula(II):
,
In the case of another kind, in described Organic Light Emitting Diode, luminescent layer material of main part has following structural formula(III):
,
In another case, in described Organic Light Emitting Diode, luminescent layer material of main part contains crosslinkable groups styrene Base, with following structural formula:
,
Under scope, in described Organic Light Emitting Diode, luminescent layer material of main part contains crosslinkable groups acrylate Base, with following structural formula:
Above-mentioned compound(II)-(V)Z=O in compound, S, S (O)2, C (R)2, Si(R)2, R is carbon number Alkyl, aryl less than 18;X is a singly-bound, and aromatic ring of the carbon atom less than 18, a carbon atom are less than 18 heteroaromatic, a carbon Thick and heteroaromatic of the atom less than 18;Ar1For H, alkyl of the carbon atom less than 8, aromatic ring of the carbon atom less than 18, a carbon Heteroaromatic of the atom less than 18, a carbon atom condense heteroaromatic less than 18;Y is C or N;Ar2-3For H, a carbon atom is less than 18 aromatic ring, heteroaromatic of the carbon atom less than 18, a carbon atom condense heteroaromatic less than 18.
In above-mentioned Organic Light Emitting Diode, luminescent layer material of main part is soluble in usual solvents, such as dimethylbenzene, 1,2- dichloro Ethane, methyl phenyl ethers anisole etc., are easy to form thin 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 again and ties thin film.Such as structure(II)Can be formed by following reaction and be handed over It is coupled 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 without departing from the scope of the invention, chemical formula(I)Middle X is singly-bound, and Y is N, and Z is C3H6When there is below formula:
Ar wherein in compound1For aromatic ring of the carbon atom less than 18, heteroaromatic of the carbon atom less than 18, carbon atom are less than 18 Condense heteroaromatic;Ar in compound2-3For H, aromatic ring of the carbon atom less than 18, heteroaromatic of the carbon atom less than 18, one Fused rings of the carbon atom less than 18;Wherein Ar2-3The unit of at least one crosslinked group is connected with, described crosslinked group is selected from second Thiazolinyl, acrylate or trifluoro vinyl.X is singly-bound in another case, and Y is N, and Z has below formula when being S:
,
Ar wherein in compound1For aromatic ring of the carbon atom less than 18, heteroaromatic of the carbon atom less than 18, carbon atom are less than 18 Condense heteroaromatic;Ar in compound2-3For H, aromatic ring of the carbon atom less than 18, heteroaromatic of the carbon atom less than 18, one Fused rings of the carbon atom less than 18;Wherein Ar2-3The unit of at least one crosslinked group is connected with, described crosslinked group is selected from second Thiazolinyl, acrylate or trifluoro vinyl.
X is singly-bound in another case, and Y is N, and Z has below formula when being SO2:
Ar wherein in compound1For aromatic ring of the carbon atom less than 18, heteroaromatic of the carbon atom less than 18, carbon atom are less than 18 Condense heteroaromatic;Ar in compound2-3For H, aromatic ring of the carbon atom less than 18, heteroaromatic of the carbon atom less than 18, one Fused rings of the carbon atom less than 18;Wherein Ar2-3The unit of at least one crosslinked group is connected with, described crosslinked group is selected from second Thiazolinyl, acrylate or trifluoro vinyl.
X is singly-bound in another case, and Y is N, and Z is NC6H5When there is below formula:
Ar wherein in compound1For aromatic ring of the carbon atom less than 18, heteroaromatic of the carbon atom less than 18, carbon atom are less than 18 Condense heteroaromatic;Ar in compound2-3For H, aromatic ring of the carbon atom less than 18, heteroaromatic of the carbon atom less than 18, one Fused rings of the carbon atom less than 18;Wherein Ar2-3The unit of at least one crosslinked group is connected with, described crosslinked group is selected from second Thiazolinyl, acrylate or trifluoro vinyl.
In a variety of structural groupings, in described organic semiconductor compound principle, there are various different groups Close, wherein preferred structure includes 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 by Ullmann under palladium catalyst or Buchwald- Hartwig reacts and obtain.For MOLECULE DESIGN purpose, Electrophilicity heteroaromatic is selected consciously(acceptor)With hole transport ability heteroaromatic(donor)It is combined into molecule so that institute The compound stated has D-A structure.
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 for an emission wavelength can also be The yellow light material of 551-580nm;Or for an emission wavelength for 581-630nm red light material.For obtain efficient green glow and HONGGUANG OLED, typically uses triplet state phosphorescent OLED. and emission layer therein contains phosphorescent light-emitting materials, such as Ir (MePPY)3 For 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, be able to can be obtained using spin coating, printing or inkjet printing Obtain certain thickness thin film.The thin film for being obtained such as larger than or is equal to 160oC in the case where ultraviolet light shines or under heating state 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 thin film in temperature change, on the other hand when further using solution spin coating, printing or inkjet printing Can still be immune, to realize that Multifunctional layered solution manufacture OLED devices provide possibility.
Organic Light Emitting Diode according to this patent scope, is characterized in that described organic 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, any triplet can answering as the luminescent material OLED of the present invention more than the material of main part of 2.4 eV With.Preferred co-host material has electron-donating material 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 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, aluminum 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 aluminum Transmit to EML after the EIL injections for connecing, through ETL.Electronics is met in EML, is combined into exciton with hole(Exciton), Then part exciton is given off energy with 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 conventional 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):
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 '- Double [N- (1- naphthyls)-N- phenylaminos] biphenyl(α-NPD)
,
Or it is poly-(3,4-rthylene dioxythiophene)- polystyrolsulfon acid(PEDOT)(CAS:155090-83-8):
For balance electronic and the injection in 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:
TPBi 。
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, or its compound such as 8- hydroxyls Lithium(Liq):
Therefore, OLED luminescent devices are the multiple structures of a complexity, and Fig. 1 is a typical construction, but is not unique answering 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, television 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 it is synthetically prepared:
Following each cross-linking material of main part compound is prepared respectively according to chemical reaction formula principle, listed compound passes through Mass spectrum demonstrates the fragment that molecular weight and molecule have, and is specifically shown in table 1 below.
Table 1:The synthesis of compound and sign
2. device application example of embodiment:
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-(Two heptane fluorenes of triphenylamine -9.9-)Solution spin-coating film as hole transmission layer, then using 2% master Body material/light-emitting dopant green glow Ir (Me-PPY)3Or HONGGUANG Ir (piq-hex)3(8% weight of doping content) mixed solution spin coating Afterwards, through heated under nitrogen to 160oC is processed 30 minutes so as to which thin film cannot not become moltenly insoluble;Secondly use one layer of solution spin coating 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 devices.Using different Host OLED luminescent devices to compare. Contrast material of main part:
,
OLED devices made by all carry out testing 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@)
Material of main part as a example by the explanation the compounds of this invention of table 2 is applied to known green glow(520 nm of emission wavelength), HONGGUANG (620 nm of emission wavelength) adulterates illuminating OLED with luminescent properties are obviously improved, than corresponding to existing material of main part PH Solution made by comparative device A, B, with higher luminous efficiency LE(Lifting amplitude is more than 30%), and driving voltage is more It is low, accelerated life LT90%Extended for more than 50% time;Meanwhile, the present invention compound, such as 3-5 and DBPP, MCBP it is auxiliary Material of main part is helped to mix prepared device 20,21 comparator devices 18, with the current efficiency and longer aging life-span that are lifted.
Indicated above, the connection one on the nitrogen-atoms of five Yuans heteroaromatic indeno carbazoles of a prosperity can be handed over containing fragrant miscellaneous fused rings Connection reactive group, is conducive to improving charge balance injection and stability of photoluminescence, can especially obtain and can pass through to change after solution film forming Crosslinking luminescent layer is learned, solution film forming electron transfer layer ET then can be continuously reused, is conducive to obtaining low cost, large area The OLED of solution manufacture.
The above, is only presently preferred embodiments of the present invention, not makees any pro forma restriction 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 technical solution of the present invention. Therefore, 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 What simple modification, equivalent variations and modification, still falls within the protection domain of technical solution of the present invention.

Claims (8)

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 include a material of main part and Phosphor dopant, material of main part therein have following general structure:
It is characterized in that Z=O in described compound, S, S (O)2, C (R)2, Si(R)2, R is alkane of the carbon number less than 18 Base, aryl;
It is characterized in that X is a singly-bound in described compound, aromatic ring of the carbon atom less than 18, a carbon atom are less than 18 Heteroaromatic, thick and heteroaromatic of the carbon atom less than 18;
It is characterized in that Ar in described compound1For H, alkyl of the carbon atom less than 8, aromatic ring of the carbon atom less than 18, Heteroaromatic of one carbon atom less than 18, a carbon atom condense heteroaromatic less than 18;
It is characterized in that Y is C or N in described compound;
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 are little Heteroaromatic is condensed in 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, 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 Z=O in described compound, S, S (O)2, C (R)2, Si(R)2, R is alkane of the carbon number less than 18 Base, aryl;
It is characterized in that X is a singly-bound in described compound, aromatic ring of the carbon atom less than 18, a carbon atom are less than 18 Heteroaromatic, thick and heteroaromatic of the carbon atom less than 18;
It is characterized in that Ar in described compound1For H, alkyl of the carbon atom less than 8, aromatic ring of the carbon atom less than 18, Heteroaromatic of one carbon atom less than 18, a carbon atom condense heteroaromatic less than 18;
It is characterized in that Y is C or N in described compound;
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 are little Heteroaromatic is condensed in 18.
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 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, is characterized in that luminescent layer in described Organic Light Emitting Diode Material of main part includes following structural formula:
5. 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.
6. 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.
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 581-630nm red light material.
8. 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:
CN201710038622.7A 2017-01-19 2017-01-19 A kind of cross-linking organic semiconductor material of main part and its Organic Light Emitting Diode application Active CN106611823B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201710038622.7A CN106611823B (en) 2017-01-19 2017-01-19 A kind of cross-linking organic semiconductor material of main part and its Organic Light Emitting Diode application

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201710038622.7A CN106611823B (en) 2017-01-19 2017-01-19 A kind of cross-linking organic semiconductor material of main part and its Organic Light Emitting Diode application

Publications (2)

Publication Number Publication Date
CN106611823A true CN106611823A (en) 2017-05-03
CN106611823B CN106611823B (en) 2018-07-10

Family

ID=58636388

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201710038622.7A Active CN106611823B (en) 2017-01-19 2017-01-19 A kind of cross-linking organic semiconductor material of main part and its Organic Light Emitting Diode application

Country Status (1)

Country Link
CN (1) CN106611823B (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108766244A (en) * 2018-06-06 2018-11-06 京东方科技集团股份有限公司 A kind of flexible display panels and preparation method thereof, display device
CN109728204A (en) * 2018-12-29 2019-05-07 上海天马微电子有限公司 Method for preparing organic functional layer of OLED
CN109796500A (en) * 2018-10-31 2019-05-24 冠能光电材料(深圳)有限责任公司 It is a kind of miscellaneous with metal complex and its electroluminescent organic luminescent device application
CN112447914A (en) * 2019-08-30 2021-03-05 冠能光电材料(深圳)有限责任公司 High-performance organic semiconductor main body material and OLED device application
CN113161497A (en) * 2021-02-08 2021-07-23 冠能光电材料(深圳)有限责任公司 Deep red organic luminescent metal iridium complex and application of organic electroluminescent device thereof
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

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102077381A (en) * 2008-06-27 2011-05-25 通用显示公司 Cross linkable ionic dopants
CN104860868A (en) * 2014-02-21 2015-08-26 环球展览公司 Organic Electroluminescent Materials And Devices
WO2016046077A1 (en) * 2014-09-25 2016-03-31 Cynora Gmbh Crosslinkable host materials
CN106255687A (en) * 2014-04-30 2016-12-21 默克专利有限公司 Material for electronic device

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102077381A (en) * 2008-06-27 2011-05-25 通用显示公司 Cross linkable ionic dopants
CN104860868A (en) * 2014-02-21 2015-08-26 环球展览公司 Organic Electroluminescent Materials And Devices
CN106255687A (en) * 2014-04-30 2016-12-21 默克专利有限公司 Material for electronic device
WO2016046077A1 (en) * 2014-09-25 2016-03-31 Cynora Gmbh Crosslinkable host materials

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108766244A (en) * 2018-06-06 2018-11-06 京东方科技集团股份有限公司 A kind of flexible display panels and preparation method thereof, display device
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
CN109796500A (en) * 2018-10-31 2019-05-24 冠能光电材料(深圳)有限责任公司 It is a kind of miscellaneous with metal complex and its electroluminescent organic luminescent device application
CN109796500B (en) * 2018-10-31 2022-07-01 冠能光电材料(深圳)有限责任公司 Hybrid metal complex and application of hybrid metal complex to organic electroluminescent device
CN109728204A (en) * 2018-12-29 2019-05-07 上海天马微电子有限公司 Method for preparing organic functional layer of OLED
CN112447914A (en) * 2019-08-30 2021-03-05 冠能光电材料(深圳)有限责任公司 High-performance organic semiconductor main body material and OLED device application
CN112447914B (en) * 2019-08-30 2024-09-24 江西冠能光电材料有限公司 High-performance organic semiconductor main body material and application of OLED device
CN113161497A (en) * 2021-02-08 2021-07-23 冠能光电材料(深圳)有限责任公司 Deep red organic luminescent metal iridium complex and application of organic electroluminescent device thereof

Also Published As

Publication number Publication date
CN106611823B (en) 2018-07-10

Similar Documents

Publication Publication Date Title
CN106611823B (en) A kind of cross-linking organic semiconductor material of main part and its Organic Light Emitting Diode application
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
CN107221611B (en) A kind of stable easy processing organic semiconducting materials and its organic luminescent device application
CN106611822A (en) Organic light-emitting device
CN106800555B (en) A kind of organic semiconductor material of main part and its Organic Light Emitting Diode application
CN106977520A (en) A kind of organic semiconducting materials containing indolocarbazole and its organic luminescent device application
CN107431140A (en) Organic electroluminescent device
CN113135945B (en) Organic boron semiconductor material and application of OLED device
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
CN104447505B (en) Stable organic light emitting diode
CN106749341B (en) Balancing charge injects organic semiconductor and its Organic Light Emitting Diode application
CN106749050B (en) It is a kind of using cyclic diketones as the hot activation delayed fluorescence OLED material of core and its application
CN103956436B (en) A kind of organic semiconductor hole transferring material
CN106654035B (en) A kind of organic semiconductor material of main part and its Organic Light Emitting Diode application
CN106800526A (en) A kind of electroluminescent organic material and its application with cyclic diketones as core
CN106784359B (en) Cross-linking balancing charge injection organic semiconductor and its Organic Light Emitting Diode application
CN107331783A (en) A kind of free radical doublet sensitized fluorescence organic electroluminescence device
CN106684253B (en) A kind of indoles quinoxaline Organic Light Emitting Diode material
CN103951657A (en) High-electronegativity organic semiconductor
CN106654036B (en) A kind of bipolarity organic semiconductor and its Organic Light Emitting Diode application
KR102128299B1 (en) Novel organic electroluminescent compound, organic electroluminescent device including the same and electric apparatus
CN108558951B (en) Sulfoxide-containing cyclometalated iridium complex and application thereof in preparation of organic electroluminescent device

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