CN106784359B - Cross-linking balancing charge injection organic semiconductor and its Organic Light Emitting Diode application - Google Patents
Cross-linking balancing charge injection organic semiconductor and its Organic Light Emitting Diode application Download PDFInfo
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Abstract
A kind of Organic Light Emitting Diode, it is characterized in that the Organic Light Emitting Diode is by a cathode, one organic semiconductor layer between anode and cathode and anode is formed, an organic luminous layer is included wherein in organic semiconductor layer, containing a cross-linking balancing charge injection organic semiconductor compound, its general formula is:(I), it is characterized in that the miscellaneous fusion ring of cross linkable virtue is connected on the N atoms of balancing charge injection naphthopyridine benzazolyl compounds, be conducive to improve charge balance injection and stability of photoluminescence, acquisition can solution film forming then by chemical crosslinking, obtain low cost, the OLED device of large area.
Description
Technical field
The present invention relates to organic semiconductor in the application of organic luminescent device, especially a kind of balancing charge injection and transmission
Organic semiconducting materials, can be applied to organic luminescent device as material of main part, improve device performance.
Background technology
Organic semiconducting materials belong to novel optoelectronic materials, its broad scale research is originating from 1977 by Hideki Shirakawa, A.
Heeger and A. McDiamid are found that doped polyacetylene of the conductivity up to copper level jointly.Then, KodaK public affairs in 1987
C. Tang of department etc. have invented organic molecule light emitting diode(OLED), and the R. Friend and A. of nineteen ninety Cambridge University
Holmes has invented polymer LED P-OLED, and S. Forrest in 1998 and M. Thomson have invented efficiency
The Phosphorescent LED P HOLED of higher.Due to organic semiconducting materials have structure easily adjust can obtain it is numerous in variety,
Can be with adjustable, or even the inexpensive benefit as being processed plastic film is multiple in conductive film, electrostatic plus organic semiconductor
Print, photovoltaic solar cell application, Organic Thin Film Transistors logic circuit, and organic light emission OLED FPD and illumination etc. are many
More applications, three scientists of Bai Chuan-Heeger-McDiamid obtained Nobel chemistry Prize in 2000.
As the Organic Light Emitting Diode of flat panel display of future generation, the requirement of organic photoelectric semiconductor has: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 injection and hole transmission layer between luminescent layer and cathode, thus reach the electronics that is balanced in luminescent layer with
Hole.It is worth noting that, in organic semiconductor, electric transmission mobility is usually less than hole transport mobility.As electronics
Transmission layer material is typically not occupy orbital energy level with relatively low LUMO-- is minimum, such as metal quinoline compound, such as three-(8-
Hydroxyl)Aluminium(Alq3), oxadiazoles or triazole type.Recently, document(Appl.Phys.Lett., 2007,90,183503 grade reports)
The hole mobile material being made of biphenyl and arylamine is reported, but dissolubility difference and film forming are difficult.
Luminescent layer is usually the semiconductor for being had by a small amount of luminescent material as object dopant incorporation one more high level
Material of main part(Or bulk material Host material)Middle composition.Recent study shows, for same luminescent material or one
Kind colour light emitting device, the difference of material of main part can cause different device light emitting efficiencies and working life.Therefore, develop new
Material of main part is always the important topic for influencing Organic Light Emitting Diode practical application.It is preferable for ease of hole, the injection of electronics
Material of main part should possess not only strong but also balance hole and electron injection and transmittability.To reach this purpose, have many
Improved material of main part appears in the newspapers.V. Adamocich (US 2006/0280965) discloses the sheet that carbazole is connected with triphenylene
Body material, but efficiency is very low;C. Adachi (WO 2012/114745) disclose be connected using pyridine with triphenylene it is bipolar
Property material of main part.A. Dyatkin (US 2012/0256169) is disclosed is made of benzothiophene, phenyl and indolepyridinium
Bipolar host material.Doosan Corp.(KR 2016076882)Disclose a kind of bipolarity of double pyridine indoles bridge joints
Material of main part;Li Xiaochang(CN201310699039.2)A kind of 3- naphthopyridines benzazolyl compounds are disclosed as bipolarity main body material
Expect the application in organic luminous layer, which is remarkably improved luminous efficiency compared to CBP, extends device operational lifetime
LT80%.But above-mentioned all material can only often use vacuum evaporation to form a film, be not suitable for obtaining large area, low using solution film forming
Cost OLED devices.
The content of the invention
For this problem, on the basis of CN201310699039.2, design herein has been synthesized with naphthopyridine indoles
Introduced for core at least containing 1 crosslinkable miscellaneous fusion base unit of virtue, construct a series of bipolar host material compounds, have concurrently
Good dissolubility can be converted into insoluble, insoluble performance again after and heating.Be conducive to acquisition can solution film forming then pass through
Chemical crosslinking, increases the heat endurance and anti-solvent ability of film, easy to reuse solution film forming, obtains multilayer solution film forming
Caused low cost, the OLED device with large area.
The compound of the present invention is applied particularly to a kind of Organic Light Emitting Diode, and technical solution is as follows:A kind of organic light emission
Diode, it is characterized in that the Organic Light Emitting Diode is made of such as lower part:
(a)One cathode
(b) anode
(c) a sandwich organic semiconductor luminescent layer between cathode and anode, the luminescent layer include a material of main part
Compound and a phosphor dopant, material of main part compound therein have following general structure:
It is characterized in that X is a singly-bound in the compound, a carbon atom is less than 18 aromatic ring, and a carbon atom is less than
18 heteroaromatic, a carbon atom are less than 18 fusion heteroaromatic;
It is characterized in that Ar in the compound1For H, a carbon atom is less than 8 alkyl, and a carbon atom is less than 18
Aromatic ring, a carbon atom are less than 18 heteroaromatic, and a carbon atom is less than 18 fusion heteroaromatic;
It is characterized in that Y is C or N in the compound;
It is characterized in that Ar2、Ar3For H, a carbon atom is less than 18 aromatic ring, and a carbon atom is less than 18 heteroaromatic, a carbon
Atom is less than 18 fusion heteroaromatic;
It is characterized in that Ar2、Ar3Be connected with the unit of at least one crosslinked group, the crosslinked group be 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 has following structure formula (II) in the Organic Light Emitting Diode:
In another case, luminescent layer material of main part compound has following structural formula in the Organic Light Emitting Diode
(III):
Or
Or
Wherein(II)~(V)Middle X is a singly-bound, and a carbon atom is less than 18 aromatic ring, and a carbon atom is fragrant miscellaneous less than 18
Ring, a carbon atom are less than 18 fusion heteroaromatic;Ar in the compound1For H, a carbon atom is less than 8 alkyl, and one
Carbon atom is less than 18 aromatic ring, and a carbon atom is less than 18 heteroaromatic, and a carbon atom is less than 18 fusion heteroaromatic;The change
Y is C or N in compound;Ar2、Ar3For H, a carbon atom is less than 18 aromatic ring, and a carbon atom is less than 18 heteroaromatic, and a carbon is former
Son is less than 18 fusion 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., easy to form film by spin coating, solution inkjet printing or printing etc., ultraviolet light shine it is lower or
Under heating condition, as temperature is more than 160oUnder C, and form insoluble cross-linked network structure film.Such as structure(II)It can lead to
Cross following reaction and form cross-linked structure:
Under other structures can be by shining lower or heating condition in ultraviolet light, heating-up temperature is more than 160oUnder C, reaction
Form following cross-linked structure:
Or
Or
Or
X is a singly-bound wherein in chemical formula, and a carbon atom is less than 18 aromatic ring, and a carbon atom is less than 18 heteroaromatic,
One carbon atom is less than 16 fusion heteroaromatic;Ar in the compound1For H, a carbon atom is less than 8 alkyl, and a carbon is former
Son is less than 18 aromatic ring, and a carbon atom is less than 18 heteroaromatic, and a carbon atom is less than 18 fusion heteroaromatic;The chemical combination
Y is C or N in thing;Ar2For H, a carbon atom is less than 18 aromatic ring, and a carbon atom is less than 18 heteroaromatic, and a carbon atom is less than
18 fusion heteroaromatic.
Within the scope of the present invention, include as follows can solution spin coating and can for luminescent layer material of main part in Organic Light Emitting Diode
Crosslinked material of main part structure:
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.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, has balance electronic concurrently in hole injection efficiency.
According to the Organic Light Emitting Diode described in this patent scope, wherein in the Organic Light Emitting Diode in luminescent layer
Luminescent material can be an emission wavelength be 510-550nm green light material;Luminescent material can also be that an emission wavelength is
The yellow light material of 551-580nm;Or it is the red light material that an emission wavelength is 581-630nm.For obtain efficient green light and
Feux rouges OLED, typically uses triplet state phosphorescent OLED emission layers therein and contains phosphorescent light-emitting materials, such as Ir (ppy)3For
Green light, or Ir (Piq)3 As red dopant, shone with 2 to 15% concentration(Weight)Material, is doped to a main body material
In material.
According to the Organic Light Emitting Diode described in this patent scope, it is characterized in that the Organic Light Emitting Diode is sometimes
Acquisition higher performance light emitting diode, the co-host of an increase electronics or Hole injection capacity can also be contained in luminescent layer
Material, namely hybrid agent material is used, wherein co-host material and the proportioning of primary body material is 5-45%.As green
Color and red phosphorescent OLED, material of main part of any triplet more than 2.4 eV all can be as the luminescent materials of the present invention
The application of OLED.Preferable 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, typically using transparent conducting glass, or indium-tin-oxide is coated with
One layer of hole injection layer HIL is deposited on ITO, then one layer of hole transmission layer HTL, luminescent layer EML, electron transfer layer successively
ETL, electron injecting layer EIL, finally add one layer of metal, such as aluminum metal layer, as anode conducting and sealant.(Fig. 1)Work as ITO
Connect positive electricity, after aluminium connection negative electricity arrives certain electric field, hole is transmitted to EML from ITO through HIL injections and HTL, and electronics is from aluminium company
EML is transmitted to after the EIL injections connect, by ETL.Electronics meets in EML with hole, is combined into exciton(Exciton),
Then part exciton is given off energy in the form of light radiation returns to ground state.The wavelength of light radiation is by the luminescent dopant in EML layers
The energy gap of agent determines.
Common material of main part is to contain carbazole or arylamine structure class material.A kind of common material of main part is 4,4 '-N, N '-
Two carbazoles-biphenyl (CBP):
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 asm-TDATA。
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
Material, example is 1,3,5- tri- (1- phenyl -1H- benzimidazolyl-2 radicals-yl) benzene TPBi, its structure is:
Between ETL and cathode, also usually using electron injecting layer.Electron injecting layer is typically the relatively low metal of work content
Lithium, or its compound such as 8-hydroxyquinoline lithium(Liq):
Therefore, OLED luminescent devices are a complicated sandwich constructions, and Fig. 1 is a typical construction, but is not uniquely should
Use structure.The general thickness of wherein organic semiconductor layer is 50-250 nanometers, and preferably gross thickness is 80-180 nanometers.
Using OLED luminescent devices, shown available for flat screen, such as Mobile phone screen, i-Pack screens, TV screen, computer screen etc..
Brief description of the drawings
Fig. 1 is organic LED structure schematic diagram.
Embodiment
Embodiment 1
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.
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, specifically see the table 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, evaporation electricity
Sub- implanted layer LiF(10 Å)/ Al100, prepares OLED devices.Using different Host OLED luminescent devices to do
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:I-V-L and accelerated aging test result
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, more right than existing material of main part DBCz institutes
Comparative device A, B answered, has the luminous efficiency LE of higher(Lifting amplitude is more than 30%), and driving voltage is lower, accelerates
Aging life-span LT90%Extended for more than 50% time;Meanwhile compound 1-11 of the invention mixes institute with MCBP co-host materials
The device 13 and 14 of preparation has excellent current efficiency and longer aging life-span.
Indicated above, to connect a cross linkable virtue miscellaneous on the N atoms of balancing charge injection naphthopyridine benzazolyl compounds
Merge ring, be conducive to improve charge balance injection and stability of photoluminescence, can especially obtain can solution film forming then pass through chemistry
Luminescent layer is crosslinked, then can continuously reuse solution film forming electron transfer layer ET, it is molten to be conducive to acquisition low cost, large area
The OLED device of liquid manufacture.
The above is only presently preferred embodiments of the present invention, not makees 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(c)One sandwich organic semiconductor luminescent layer between cathode and anode, the luminescent layer include a material of main part chemical combination Thing and a phosphor dopant, material of main part compound therein have following general structure:It is characterized in that X is a singly-bound in the compound, a carbon atom is less than 18 aromatic ring, and a carbon atom is less than 18 Heteroaromatic, a carbon atom are less than 18 fusion heteroaromatic;It is characterized in that Ar in the compound1For H, a carbon atom is less than 8 alkyl, and a carbon atom is less than 18 aromatic ring, One carbon atom is less than 16 heteroaromatic, and a carbon atom is less than 18 fusion heteroaromatic;It is characterized in that Y is C or N in the compound;It is characterized in that Ar2、Ar3For H, a carbon atom is less than 18 aromatic ring, and a carbon atom is less than 18 heteroaromatic, a carbon atom Fusion heteroaromatic less than 18;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 X is a singly-bound in the compound, a carbon atom is less than 18 aromatic ring, and a carbon atom is less than 18 Heteroaromatic, a carbon atom are less than 18 fusion heteroaromatic;It is characterized in that Ar in the compound1For H, a carbon atom is less than 8 alkyl, and a carbon atom is less than 18 aromatic ring, One carbon atom is less than 18 heteroaromatic, and a carbon atom is less than 18 fusion heteroaromatic;It is characterized in that Y is C or N in the compound;It is characterized in that Ar2、Ar3For H, a carbon atom is less than 18 aromatic ring, and a carbon atom is less than 18 heteroaromatic, a carbon atom Fusion heteroaromatic less than 18.
- 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 is more than 160 in heating-up temperatureoC, forms insoluble cross-linked network structure:OrOrOr(V-X)It is characterized in that X is a singly-bound in the compound, a carbon atom is less than 18 aromatic ring, and a carbon atom is less than 18 Heteroaromatic, a carbon atom are less than 18 fusion heteroaromatic;It is characterized in that Ar in the compound1For H, a carbon atom is less than 8 alkyl, and a carbon atom is less than 18 aromatic ring, One carbon atom is less than 18 heteroaromatic, and a carbon atom is less than 18 fusion heteroaromatic;It is characterized in that Y is C or N in the compound;It is characterized in that Ar2、Ar3For H, a carbon atom is less than 18 aromatic ring, and a carbon atom is less than 18 heteroaromatic, a carbon atom Fusion heteroaromatic less than 18.
- 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 includes 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 Electronegativity material MCBP:
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