CN106611823B - A kind of cross-linking organic semiconductor material of main part and its Organic Light Emitting Diode application - Google Patents
A kind of cross-linking organic semiconductor material of main part and its Organic Light Emitting Diode application Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 78
- 239000004065 semiconductor Substances 0.000 title claims abstract description 18
- 238000004132 cross linking Methods 0.000 title abstract description 12
- 238000002347 injection Methods 0.000 claims abstract description 16
- 239000007924 injection Substances 0.000 claims abstract description 16
- -1 heteroaromatic indeno carbazoles Chemical class 0.000 claims abstract description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 72
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 239000002019 doping agent Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 4
- NSXJEEMTGWMJPY-UHFFFAOYSA-N 9-[3-(3-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=CC=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 NSXJEEMTGWMJPY-UHFFFAOYSA-N 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
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- 125000004432 carbon atom Chemical group C* 0.000 claims 22
- 239000000243 solution Substances 0.000 abstract description 20
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- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 230000005611 electricity Effects 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
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- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
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- 125000005580 triphenylene group Chemical group 0.000 description 2
- IVFQIAUDJCXUJJ-UHFFFAOYSA-N 2-octylquinoline Chemical compound C1=CC=CC2=NC(CCCCCCCC)=CC=C21 IVFQIAUDJCXUJJ-UHFFFAOYSA-N 0.000 description 1
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
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- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
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- 239000012296 anti-solvent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000005264 aryl amine group Chemical group 0.000 description 1
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- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
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- 239000012634 fragment Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
A kind of Organic Light Emitting Diode, it is characterized in that the Organic Light Emitting Diode, by a cathode, an organic semiconductor layer between anode and cathode and anode is formed, and an organic luminous layer is included wherein in organic semiconductor layer, containing a kind of cross-linking organic semiconductor material of main part, general formula is：It is characterized in that connection one is containing the miscellaneous fused rings of cross-linking reactive group virtue on the nitrogen-atoms of five Yuans flourishing heteroaromatic indeno carbazoles, be conducive on the basis of the injection of improvement charge balance and stability of photoluminescence is obtained, convenient for being further made of solution film forming, it is obtained by crosslinking and does not melt insoluble stabilized illumination layer, realize continuous inexpensive solution spin coating, inkjet printing multilayer OLED light emitting displays.
Description
Technical field
The present invention relates to organic semiconductor in the application of organic luminescent device, the balance electricity of especially a kind of cross-linking reaction
Lotus injects the organic semiconducting materials with transmission, material of main part can be used as by solution film forming, applied to low cost, large area
Organic luminescent device, improve device performance.
Background technology
Organic semiconducting materials belong to novel optoelectronic materials, and 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
Higher Phosphorescent LED P HOLED.Due to organic semiconducting materials have structure easily adjust can obtain it is numerous in variety,
Energy band is adjustable or even the inexpensive benefit as being processed plastic film, in addition organic semiconductor, in conductive film, electrostatic is multiple
Print, photovoltaic solar cell application, Organic Thin Film Transistors logic circuit and organic light emission OLED FPD and illumination etc. are many
It applies, three scientists of Bai Chuan-Heeger-McDiamid obtained Nobel chemistry Prize in 2000 more.
As the Organic Light Emitting Diode of next-generation flat panel display, organic photoelectric semiconductor requires to have：1. height shines
Efficiency；2. excellent electronics and hole stability；3. suitable luminescent 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, has 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 for 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 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 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）.Light emitting molecule is answered to mix along with transmitting luminous energy, transmitting luminous energy wavelength face after exciton state replying agent ground state
Miscellaneous dose of energy gap（HOMO-LUMO energy level differences）.
Have the heavy metal organic ligand complex compound much reported, influenced by heavy metal and enhance 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)3And its derivative I r (MePPY)3It is with structural formula：
,
The FirPic of transmitting blue light has the following structure formula：
,
Main ligand 4 therein, 6- difluoro-benzene yl pyridines dominate luminescent color.Emit 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 electron-transport need to be usually added between luminescent layer and anode
Layer adds hole note and hole transmission layer between luminescent layer and cathode, so as to reach the electronics balanced in luminescent layer and sky
Cave.It is worth noting that, in organic semiconductor, electron-transport mobility is usually less than hole transport mobility.It is passed as electronics
Defeated layer material is typically not occupy orbital energy level with relatively low LUMO-- is minimum, such as metal quinoline compound, such as three-（8- hydroxyls
Base）Aluminium（Alq3）, oxadiazoles or triazole type.Recently, document（Appl.Phys.Lett., 2007,90,183503 grade reports）Report
The hole mobile material that road is made of biphenyl and arylamine, but dissolubility difference and film forming are difficult.
Luminescent layer is usually the semiconductor for being had by a small amount of luminescent material as object dopant incorporation one more high level
Material of main part（Or bulk material Host material）Middle composition.Recent study shows for same luminescent material or one
Kind colour light emitting device, the difference of material of main part can lead to different device light emitting efficiencies and working life.Therefore, it develops novel
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 have 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 connect with triphenylene
Body material.C. Adachi (WO 2012/114745) discloses the bipolar host material being connect using pyridine with triphenylene.
A. Dyatkin (US 2012/0256169) discloses the bipolarity master being made of benzothiophene, phenyl and indolepyridinium
Body material.A.M.Parham has delivered bipolar host material（WO2013041176A)：
,
But the OLED device application of superperformance is not disclosed, especially such compound is only suitable for steaming using traditional vacuum
Plating film forming is not suitable for preparing large area, low cost OLED luminescent devices using solution film forming.
Invention content
The present invention provides a kind of organic compound semiconductor, on the nitrogen-atoms of five Yuans flourishing heteroaromatic indeno carbazoles
Connection one is constructed a series of bipolar host material compounds, is had both good molten containing the miscellaneous fused rings of cross-linking reactive group virtue
Insoluble, insoluble performance can be converted into after solution performance and heating again.Be conducive to obtain can solution film forming then by chemical crosslinking,
Increase the thermal stability of film and anti-solvent ability, convenient for reusing solution film forming being crosslinked function layer surface, realize low
Cost spin coating, inkjet printing obtain low cost caused by multilayer solution film forming, the OLED device with large area.It is applied particularly to
A kind of Organic Light Emitting Diode, it is characterized in that the Organic Light Emitting Diode is made of such as lower part：
(a), a cathode
（b）, an anode
（c）, a sandwich organic semiconductor luminescent layer between cathode and anode, which includes a material of main part
With a phosphor dopant, material of main part therein has the following structure general formula：
,
It is characterized in that Z=O in the compound, S, S (O)2, C (R)2, Si(R)2, R is carbon atom number less than 18
Alkyl, aryl；
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 thick and 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 condensed heteroaromatic；
It is characterized in that Y is C or N in the compound；
It is characterized in that Ar2-3For 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 condensed heteroaromatic；
It is characterized in that Ar2-3The unit of at least one crosslinked group is connected with, the crosslinked group is selected from vinyl, third
Olefin(e) acid fat or trifluoro vinyl.
All have crosslinking function there are many chemical group, wherein be typically included in heating or ultraviolet light shine under crosslinking
Group, such as be connected on phenyl ring and include vinyl as follows（A）, acrylic（B）And trifluoro vinyl（C）：
。
Yi Shang 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 contains crosslinkable groups trifluoro vinyl in the Organic Light Emitting Diode, tool
Just like lower structure formula（II）：
,
In another case, luminescent layer material of main part has the following structure formula in the Organic Light Emitting Diode（III）：
,
In another case, luminescent layer material of main part contains crosslinkable groups benzene second in the Organic Light Emitting Diode
Alkenyl has the following structure formula：
,
Under scope, luminescent layer material of main part contains crosslinkable groups propylene in the Organic Light Emitting Diode
Perester radical has the following structure formula：
。
Above-mentioned compound（II）（V）Z=O in compound, S, S (O)2, C (R)2, Si(R)2, R is carbon atom number
Alkyl, aryl less than 18；X is a singly-bound, and 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 thick and heteroaromatic；Ar1For H, a carbon atom is less than 8 alkyl, and a carbon atom is less than 18 aromatic ring, a carbon
Atom is less than 18 heteroaromatic, and a carbon atom is less than 18 condensed heteroaromatic；Y is C or N；Ar2-3For H, 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 condensed 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. form film convenient for passing through spin coating, solution inkjet printing or printing etc..It shines lower in ultraviolet light or adds
Hot temperature is more than 160oC, and form insoluble cross-linked network knot film.Such as structure（II）Friendship can be formed by reacting as follows
It is coupled structure II-X：
；
Structure（III）Cross-linked structure III-X can be formed by reacting as follows：
Structure（IV）Cross-linked structure IV-X can be formed by reacting as follows：
；
Structure（V）Cross-linked structure V-X can be formed by reacting as follows：
。
In without departing from the scope of the invention, chemical formula（I）Middle X be singly-bound, Y N, Z C3H6When have below formula：
Ar wherein in compound1It is less than 18 aromatic ring for carbon atom, carbon atom is less than 18 heteroaromatic, and carbon atom is less than
18 condensed heteroaromatic；Ar in compound2-3For H, a carbon atom is less than 18 aromatic ring, and a carbon atom is less than 18 heteroaromatic,
One carbon atom is less than 18 fused rings；Wherein Ar2-3The unit of at least one crosslinked group is connected with, the crosslinked group is selected from
Vinyl, acrylate or trifluoro vinyl.X is singly-bound in another case, and Y N have below formula when Z is S：
,
Ar wherein in compound1It is less than 18 aromatic ring for carbon atom, carbon atom is less than 18 heteroaromatic, and carbon atom is less than
18 condensed heteroaromatic；Ar in compound2-3For H, a carbon atom is less than 18 aromatic ring, and a carbon atom is less than 18 heteroaromatic,
One carbon atom is less than 18 fused rings；Wherein Ar2-3The unit of at least one crosslinked group is connected with, the crosslinked group is selected from
Vinyl, acrylate or trifluoro vinyl.
X is singly-bound in another case, and Y N have below formula when Z is SO2：
Ar wherein in compound1It is less than 18 aromatic ring for carbon atom, carbon atom is less than 18 heteroaromatic, and carbon atom is less than
18 condensed heteroaromatic；Ar in compound2-3For H, a carbon atom is less than 18 aromatic ring, and a carbon atom is less than 18 heteroaromatic,
One carbon atom is less than 18 fused rings；Wherein Ar2-3The unit of at least one crosslinked group is connected with, the crosslinked group is selected from
Vinyl, acrylate or trifluoro vinyl.
In another case X be singly-bound, Y N, Z NC6H5When have below formula：
Ar wherein in compound1It is less than 18 aromatic ring for carbon atom, carbon atom is less than 18 heteroaromatic, and carbon atom is less than
18 condensed heteroaromatic；Ar in compound2-3For H, a carbon atom is less than 18 aromatic ring, and a carbon atom is less than 18 heteroaromatic,
One carbon atom is less than 18 fused rings；Wherein Ar2-3The unit of at least one crosslinked group is connected with, the crosslinked group is selected from
Vinyl, acrylate or trifluoro vinyl.
In the combination of a variety of different structures, there are various different groups in the organic semiconductor compound principle
It closes, wherein preferred structure includes following compound：
。
It can be prepared in any of the above compound principle by a variety of chemical reactions, the most commonly used is secondary amine and halogenated 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.
According to the Organic Light Emitting Diode described in this patent range, 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 may 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 (MePPY)3
For green light or Ir (Piq-Hex)3 As red dopant, shone with 2 to 15% concentration（Weight）Material is doped to one
In material of main part.Using material of main part and doped luminescent material mixed solution, it spin coating, printing or inkjet printing that can be used can obtain
Obtain certain thickness film.The film obtained is in the case where ultraviolet light shines or under heating state, such as larger than or equal to 160oC
Under, then after chemical reaction becomes insoluble insoluble network structure to cross-linking functional group, is on the one hand conducive to fixed dopant, increases
Add dimensional stability of the film in temperature change, on the other hand when further using solution spin coating, printing or inkjet printing
It can still be not affected, possibility is provided to realize that Multifunctional layered solution manufactures OLED devices.
According to the Organic Light Emitting Diode described in this patent range, it is characterized in that described is organic sometimes for acquisition higher
Performance light emitting diode, the co-host material that electronics or Hole injection capacity can also be increased containing one in luminescent layer namely
Using hybrid agent material, the proportioning of wherein co-host material and primary body material is 5-45%.As green and red phosphorus
Light OLED, material of main part of any triplet more than 2.4 eV all can answering as the luminescent material OLED of the present invention
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, typically using transparent conducting glass or it is coated with indium-tin-oxide
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
Positive electricity is connect, after aluminium connects negative electricity to certain electric field, hole is transmitted to EML from ITO through HIL injections and HTL, and electronics connects from aluminium
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.
The most commonly used is containing carbazole or arylamine structure class material for material of main part.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 as m-TDATA,
。
Similarly, between hole injection layer and emission layer EML, a hole transmission layer also may be selected, such as using 4,4 '-
Bis- [N- (1- naphthalenes)-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, it can optional electron-transport hole barrier（ETHB) material
Material, example is 1,3,5- tri- (1- phenyl -1H- benzimidazolyl-2 radicals-yl) benzene TPBi, and structure is：
Between ETHL and cathode, also usually using electron injecting layer.Electron injecting layer is typically the relatively low metal of work content
Lithium or its compound such as 8- hydroxyls Lithium（Liq）：
Therefore, OLED luminescent devices are a complicated multilayered structures, 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 overall thickness is 80-180 nanometers.
It using OLED luminescent devices, is shown available for flat screen, such as Mobile phone screen, i-Pack screens, TV screen, computer screen etc..
Description of the drawings
Fig. 1 is organic LED structure schematic diagram.
Specific embodiment
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 specific 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 without violating the connotation of the present invention.Therefore the present invention is not limited by following public specific embodiment
System.
Embodiment 1：Compound is synthetically prepared：
Following each cross-linking material of main part compound, listed compound are prepared according to chemical reaction general formula principle respectively
By mass spectrum demonstrate molecular weight and molecule possessed by fragment, be specifically shown in the following table 1.
Table 1：The synthesis of compound 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 made to 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, vapor deposition electricity
Sub- implanted layer LiF（10 Å）/ Al100 prepares OLED devices.Using different Host OLED luminescent devices to do ratio
Compared with.Compare material of main part：
,
OLED devices made of all carry out test I-V-L and accelerated aging test after encapsulation, as a result summarize such as table 2.
Table 2：OLED device performances (1000 nits of@)
。
Table 2 illustrates that the material of main part for the compounds of this invention is applied to known green light（520 nm of emission wavelength）, feux rouges
(620 nm of emission wavelength) doping illuminating OLED, which has, is obviously improved luminescent properties, than corresponding to existing material of main part PH
Solution made of comparative device A, B, have higher luminous efficiency LE（Promotion amplitude is more than 30%）, and driving voltage is more
It is low, accelerated life LT90%Extended for more than 50% time；Meanwhile the compound of the present invention, such as 3-5 and DBPP, MCBP is auxiliary
Material of main part is helped to mix prepared device 20,21 comparator devices 18, there is the current efficiency promoted and longer aging life-span.
Indicated above, the miscellaneous fused rings containing virtue of connection one can be handed on the nitrogen-atoms of five Yuans flourishing heteroaromatic indeno carbazoles
Join reactive group, be conducive to improve charge balance injection and stability of photoluminescence, can especially obtain can passing through after solution film forming
Crosslinking luminescent layer is learned, then can continuously reuse solution film forming electron transfer layer ET, is conducive to obtain low cost, large area
The OLED device of solution manufacture.
The above described is only a preferred embodiment of the present invention, not make limitation in any form to the present invention.Appoint
What those skilled in the art, without departing from the scope of the technical proposal of the invention, all using the skill of the disclosure above
Art content makes technical solution of the present invention many possible changes and modifications or is revised as the equivalent embodiment of equivalent variations.
Therefore, every content without departing from technical solution of the present invention, made to the above embodiment of technical spirit according to the present invention
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 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
Object and a phosphor dopant compound, material of main part compound therein have the following structure general formula：
It is characterized in that Z=O in the compound, S, S (O)2, C (R)2, Si(R)2, wherein R is chosen as carbon atom number and is less than
18 alkyl, aryl；
It is characterized in that X is chosen as a singly-bound in compound, a carbon atom is less than 18 aromatic ring, and a carbon atom is less than 18 virtue
Heterocycle, a carbon atom are less than 18 thick and heteroaromatic；
It is characterized in that Ar in compound1It is chosen as H, a carbon atom is less than 8 alkyl, and a carbon atom is less than 18 aromatic ring, and one
Carbon atom is less than 18 heteroaromatic, and a carbon atom is less than 18 condensed heteroaromatic；
It is characterized in that Y is C or N in compound；
It is characterized in that Ar2、Ar3H is chosen as, 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 condensed heteroaromatic, wherein Ar2 、Ar3It can be the same or different；
It is characterized in that Ar2,Ar3To be connected with the unit of at least one crosslinked group, the crosslinked group is selected from vinyl, third
Olefin(e) acid fat or trifluoro vinyl, wherein Ar2 、Ar3It can be the same or different.
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 the following structure formula：
Or
Or
It is characterized in that Z=O in the compound, S, S (O)2, C (R)2, Si(R)2, it is small to be chosen as carbon atom number wherein R
Alkyl, aryl in 18；
It is characterized in that X is chosen as 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 thick and heteroaromatic；
It is characterized in that Ar in the compound1H is chosen as, 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 condensed heteroaromatic；
It is characterized in that Y is C or N in the compound；
It is characterized in that Ar2、Ar3H is chosen as, 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 condensed heteroaromatic, wherein Ar2 、Ar3It can be the same or different.
3. Organic Light Emitting Diode according to claim 2, it is characterized in that luminescent layer in the Organic Light Emitting Diode
Material of main part compound is more than 160 in heating 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 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 increase electronics or Hole injection capacity containing one co-host material, co-host material be electron-donating material DBPP or
Electronegativity material MCBP：
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| 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 |
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| CN104860868A (en) * | 2014-02-21 | 2015-08-26 | 环球展览公司 | Organic Electroluminescent Materials And Devices |
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