CN108807707A - A kind of organic luminescent device - Google Patents
A kind of organic luminescent device Download PDFInfo
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- CN108807707A CN108807707A CN201810573458.4A CN201810573458A CN108807707A CN 108807707 A CN108807707 A CN 108807707A CN 201810573458 A CN201810573458 A CN 201810573458A CN 108807707 A CN108807707 A CN 108807707A
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/166—Electron transporting layers comprising a multilayered structure
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- 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
- H10K85/10—Organic polymers or oligomers
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- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
Abstract
The present invention provides a kind of organic luminescent devices, are related to organic field of photoelectric technology.The device of the present invention is two-layer electronic transmission apparatus structure, including making the first electron transfer layer and compound in triazine class as the second electron transfer layer with azepine carbazole compound.Azepine carbazole compound has high electron mobility, and the compound in triazine class with specific fluorenes class group not only has high electron mobility, but also since the addition of fluorenes makes carrier transport in its structure balance.By rationally adjusting the matching of two class compounds in the devices, the luminous efficiency of organic luminescent device of the present invention increases significantly, and driving voltage is decreased obviously, and is a kind of organic luminescent device haveing excellent performance, can be widely applied to display field.
Description
Technical field
The present invention relates to organic photoelectric technical fields, and in particular to a kind of organic luminescent device.
Background technology
In recent years, Organic Light Emitting Diode (OLED:Organic Light Emitting Diode) as a kind of novel
The visual field of people is progressed into promising display technology.It is compared with traditional display technology, in voltage characteristic, luminance
Degree, luminous efficiency, device weight, response speed and appreciative perspective etc. have significant advantage, and because of its low cost potential,
Possess broad mass market foreground.
In general, OLED has stratiform or laminar structure.For example, typical OLED has anode/organic luminous layer/cathode more
Layer structure.OLED can also have various other structures, such as anode/hole injection layer/hole transmission layer/luminescent layer/electronics passes
Defeated layer/electron injecting layer/cathode multilayered structure or anode/hole injection layer/hole transmission layer/luminescent layer/hole blocking layer/electricity
Sub- transport layer/electron injecting layer/cathode multilayered structure.
But there is luminous efficiency and service life more in traditional OLED display device, mainly there is following several originals
Cause：On the one hand the matching degree between the luminescent properties and each layer combined material of luminous organic material used is depended on；On the one hand it takes
Certainly in exciton utilization rate, since hole is different with the transmission speed of electronics in organic photoelectrical material, conventional device structure holds very much
Easily there is carrier and inject unbalanced problem, causes electrons and holes combined efficiency low and the offset of recombination region, to lead
Cause organic electroluminescence device luminous efficiency is low, the service life is low；On the other hand, the packaged type of organic electroluminescence device is more
For thin-film package, in the process, packaging film may will produce tiny channel so that the moisture in environment and oxygen contact
To OLED display device.And the cathode on upper layer often uses the higher metal of activity, is easily generated after being contacted with moisture and oxygen
The failure of device.
As market further increases OLED device requirement, seek higher luminous efficiency, the more long-life, more inexpensive
OLED device become the trend of development, so develop a kind of more excellent performance of organic luminescent device, become it is a kind of urgently
Problem to be solved.
Invention content
The object of the present invention is to provide a kind of organic luminescent devices of achievable higher luminous efficiency and service life.
The present invention provides a kind of organic luminescent device, includes substrate, anode, hole injection layer, hole transmission layer, hair successively
Photosphere, the first electron transfer layer, the second electron transfer layer, electron injecting layer and cathode, wherein
First electron transfer layer includes the azepine carbazole compound indicated by formula (1), and
Second electron transfer layer includes the compound in triazine class indicated by formula (2)：
Wherein, R1、R2It is independent to be selected from substituted or unsubstituted C1~C30Alkyl, substituted or unsubstituted C6~C30's
Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind；X1~X4It is independent to be selected from carbon atom or nitrogen-atoms；L is selected from
Singly-bound, substituted or unsubstituted C6~C30Aryl in one kind,
Wherein, Ar1、Ar2、Ar3It is independent to be selected from substituted or unsubstituted C6~C65Aryl, substituted or unsubstituted C3
~C65Heteroaryl in one kind, and it is at least one be selected from following group：
Wherein, R3、R4It is independent to be selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30's
Aryl, substituted or unsubstituted C6~C30Heteroaryl in one kind；R5Selected from hydrogen atom, substituted or unsubstituted C1~C10's
Alkyl, substituted or unsubstituted C6~C30Aryl in one kind.
Preferably, the X in the formula (1)2、X3In it is at least one be nitrogen-atoms, X1、X4For carbon atom.
Preferably, the general formula for the azepine carbazole compound that first electron transfer layer includes such as (1-1) or (1-2) institute
Show：
L is selected from singly-bound, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, takes
One kind in generation or unsubstituted phenanthryl, substituted or unsubstituted base in the wrong, substituted or unsubstituted triphenylene.
Preferably, R in the formula (1)1、R2It is independent to be selected from methyl, ethyl, isopropyl, tertiary butyl, substitution or unsubstituted
Phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substitution or unsubstituted
Triphenylene, substituted or unsubstituted acridinyl, substituted or unsubstituted phenoxazine base, substituted or unsubstituted phenthazine
Base, substituted or unsubstituted phenoxazine thiophene base, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazyl, substitution do not take
The pyrenyl in generation, substituted or unsubstituted ferrosin base, substituted or unsubstituted base, substituted or unsubstituted acenaphthenyl, substitution or
Unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazine
Base, substituted or unsubstituted triazine radical, substituted or unsubstituted pyrrole radicals, substituted or unsubstituted benzopyrrole base, substitution or
Unsubstituted triazolyl, substituted or unsubstituted thienyl, substituted or unsubstituted furyl, substituted or unsubstituted benzo thiophene
Pheno base, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzo
One kind in furyl.
Preferably, Ar in the formula (2)1、Ar2、Ar3It is at least one to be selected from following group：
Wherein, R3、R4It is independent to be selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, take
Generation or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene
Base, substituted or unsubstituted base, substituted or unsubstituted ferrosin base, substituted or unsubstituted pyridyl group, substitution do not take
The pyrimidine radicals in generation, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine radical, takes substituted or unsubstituted pyrazinyl
Generation or unsubstituted pyrrole radicals, substituted or unsubstituted benzopyrrole base, substituted or unsubstituted triazolyl, substitution or unsubstituted
Thienyl, substituted or unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuran
Base, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted quinoline
One kind in base, substituted or unsubstituted isoquinolyl, substituted or unsubstituted indyl；R5Selected from hydrogen atom, methyl, second
Base, isopropyl or tertiary butyl.
Preferably, the Ar in the formula (2)1、Ar2、Ar3It is at least one to be selected from following group：
Wherein, R3、R4It is independent to be selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, take
It is generation or unsubstituted anthryl, substituted or unsubstituted ferrosin base, substituted or unsubstituted pyridyl group, substituted or unsubstituted phonetic
Piperidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substitution or
One kind in unsubstituted indyl；R5Selected from hydrogen atom, methyl, ethyl, isopropyl or tertiary butyl.
Preferably, Ar in the formula (2)2、Ar3It is identical, it is selected from following group：
Wherein, R3、R4It is independent to be selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, take
Generation or unsubstituted anthryl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted pyrazine
One kind in base；R5Selected from hydrogen atom, methyl, ethyl, isopropyl or tertiary butyl.
Preferably, the Ar in the formula (2)1Selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution
Or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted acridine
Base, substituted or unsubstituted phenoxazine base, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazine thiophene base, substitution
Or unsubstituted fluorenyl, substituted or unsubstituted carbazyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted ferrosin
It is base, substituted or unsubstituted base, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted
Pyrimidine radicals, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine radical, substitution or
Unsubstituted pyrrole radicals, substituted or unsubstituted benzopyrrole base, substituted or unsubstituted triazolyl, substituted or unsubstituted thiophene
Pheno base, substituted or unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl,
One kind in substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran group.
Further preferably, the one kind of the azepine carbazole compound in following compounds：
Further preferably, the one kind of the compound in triazine class in following compounds：
Beneficial effects of the present invention：
A kind of organic luminescent device provided by the invention, this device is two-layer electronic transmission apparatus structure, including having nitrogen
Miscellaneous carbazole compound makees the first electron transfer layer and compound in triazine class as the second electron transfer layer.
The first electron transfer layer of the present invention includes azepine carbazole compound, this compound not only has azepine carbazyl
Group, also benzimidazole group.On the one hand, the energy that azepine carbazole group has very high triplet energy level (2.96eV) and stablizes
Grade, not only remains the high triplet of carbazole group, undersaturated C=N double bonds is also introduced into group, improves electronics biography
Movement Capabilities, by the way that the adjusting to material carrier transmittability even may be implemented from different group keys；On the one hand, benzimidazole
Class group is a kind of with good rigid planar structure and abundant pi-electron cloud density and excellent electron delocalization environment
Particular molecule, and the pi-pi accumulation of aromatic ring can make the compound with such group with stronger stability on benzimidazole；
On the other hand, benzimidazole group is combined a kind of electron transport material to be formed with azepine carbazole group, increases conjugated system,
Larger molecular weight improves the glass transition temperature of compound, especially intermediate to be connected using a series of aryl, continuous pi-conjugated body
Frenulum carrys out preferable electron mobility, to have high electron mobility.
The second electron transfer layer of the present invention includes compound in triazine class, this compound has the spy being connected with fluorenes class formation
Point.On the one hand, triazine group especially 1,3,5-triazines unit structure is relatively stablized, acid and alkali-resistance and high temperature resistant, has high glass
Change temperature；Triazine group is as typical strong electron-withdrawing group group, and compound of structure has high electron transfer centered on it
Rate and lower energy level.On the one hand, fluorenes class group is the space structure of 3 D stereo, be can effectively prevent intermolecular poly-
Collection, makes it be not easy to crystallize；Easily modification, strong rigid advantage make compound structure stablize in fluorenes class group.On the other hand, triazine radical
Group is combined a kind of triaizine compounds for the class formation containing fluorenes to be formed with fluorenes class group, especially therebetween by phenyl ring or cyclohexyl biphenyl
Connection, increases conjugated system, possesses extensible three-dimensional structure, and continuous pi-conjugated system brings preferable electron mobility,
To have high electron mobility；Also, the combination of the two makes carrier transport balance.
Organic luminescent device of the present invention is by carrying out above-mentioned first electron transfer layer and the second electron transfer layer
Combination improves exciton in the production rate and utilization rate of luminescent layer, avoids carrier and shining to improve electron transfer rate
The imbalance of layer avoids electron transfer layer from deteriorating with device lifetime caused by the heat localization of luminous bed boundary, to reduce device
The cut-in voltage of part improves the luminous efficiency and service life of device.
The raw materials of compound that organic luminescent device of the present invention uses is easy to get, and synthesis is simple, easy to operate.
Description of the drawings
Fig. 1 is a kind of organic luminescent device sectional view.
Wherein, 1/ anode of substrate, 2/ hole injection layer, 3/ hole transmission layer, 4/ luminescent layer, 5/ first electron transfer layer 6/ second
7/ electron injecting layer of electron transfer layer, 8/ cathode 9.
Specific implementation mode
For a further understanding of the present invention, the preferred embodiment of the invention is described with reference to embodiment, still
It should be appreciated that these descriptions are only the feature and advantage further illustrated the present invention, rather than to the claims in the present invention
Limitation.
Alkyl of the present invention refers to alkyl made of minusing a hydrogen atom in alkane molecule, can be straight chain alkane
Base, branched alkyl, naphthenic base, example may include methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, tertiary fourth
Base, amyl, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Aryl of the present invention refer to aromatic hydrocarbon molecule aromatic core carbon on remove a hydrogen atom after, be left univalent perssad it is total
Claiming, can be monocyclic aryl or fused ring aryl, example may include phenyl, xenyl, naphthalene, anthryl, phenanthryl or pyrenyl etc., but
It is without being limited thereto.
Heteroaryl of the present invention refers to the group that one or more of aryl aromatic core carbon is substituted by hetero atom
General name, the hetero atom include but not limited to oxygen, sulphur or nitrogen-atoms, and the heteroaryl can be bicyclic heteroaryl or condensed ring heteroaryl
Base, example may include pyridyl group, pyrrole radicals, pyridyl group, thienyl, furyl, indyl, quinolyl, isoquinolyl, benzo thiophene
Pheno base, benzofuranyl, dibenzofuran group, dibenzothiophene, carbazyl etc., but not limited to this.
Substituted alkyl of the present invention, substituted alkoxy, substituted aryl, substituted aryl amine, substituted heteroaryl
In base, the substituent group is independently selected from deuterium, C1-C10 alkyl, cyano, nitro, C6-C24 aryl or C3-C20 heteroaryls.
The present invention provides a kind of organic luminescent devices, successively include substrate, anode, hole injection layer, hole transmission layer,
Luminescent layer, the first electron transfer layer, the second electron transfer layer, electron injecting layer and cathode, wherein
First electron transfer layer includes the azepine carbazole compound indicated by formula (1), and
Second electron transfer layer includes the compound in triazine class indicated by formula (2)：
Wherein, R1、R2It is independent to be selected from substituted or unsubstituted C1~C30Alkyl, substituted or unsubstituted C6~C30's
Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind；X1~X4It is independent to be selected from carbon atom or nitrogen-atoms；L is selected from
Singly-bound, substituted or unsubstituted C6~C30Aryl in one kind,
Wherein, Ar1、Ar2、Ar3It is independent to be selected from substituted or unsubstituted C6~C65Aryl, substituted or unsubstituted C3
~C65Heteroaryl in one kind, and it is at least one be selected from following group：
Wherein, R3、R4It is independent to be selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30's
Aryl, substituted or unsubstituted C6~C30Heteroaryl in one kind；R5Selected from hydrogen atom, substituted or unsubstituted C1~C10's
Alkyl, substituted or unsubstituted C6~C30Aryl in one kind.
Preferably, the X in the formula (1)2、X3In it is at least one be nitrogen-atoms, X1、X4For carbon atom.
Preferably, the general formula for the azepine carbazole compound that first electron transfer layer includes such as (1-1) or (1-2) institute
Show：
L is selected from singly-bound, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, takes
One kind in generation or unsubstituted phenanthryl, substituted or unsubstituted base in the wrong, substituted or unsubstituted triphenylene.
Preferably, R in the formula (1)1、R2It is independent to be selected from methyl, ethyl, isopropyl, tertiary butyl, substitution or unsubstituted
Phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substitution or unsubstituted
Triphenylene, substituted or unsubstituted acridinyl, substituted or unsubstituted phenoxazine base, substituted or unsubstituted phenthazine
Base, substituted or unsubstituted phenoxazine thiophene base, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazyl, substitution do not take
The pyrenyl in generation, substituted or unsubstituted ferrosin base, substituted or unsubstituted base, substituted or unsubstituted acenaphthenyl, substitution or
Unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazine
Base, substituted or unsubstituted triazine radical, substituted or unsubstituted pyrrole radicals, substituted or unsubstituted benzopyrrole base, substitution or
Unsubstituted triazolyl, substituted or unsubstituted thienyl, substituted or unsubstituted furyl, substituted or unsubstituted benzo thiophene
Pheno base, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzo
One kind in furyl.
Preferably, Ar in the formula (2)1、Ar2、Ar3It is at least one to be selected from following group：
Wherein, R3、R4It is independent to be selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, take
Generation or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene
Base, substituted or unsubstituted base, substituted or unsubstituted ferrosin base, substituted or unsubstituted pyridyl group, substitution do not take
The pyrimidine radicals in generation, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine radical, takes substituted or unsubstituted pyrazinyl
Generation or unsubstituted pyrrole radicals, substituted or unsubstituted benzopyrrole base, substituted or unsubstituted triazolyl, substitution or unsubstituted
Thienyl, substituted or unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuran
Base, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted quinoline
One kind in base, substituted or unsubstituted isoquinolyl, substituted or unsubstituted indyl；R5Selected from hydrogen atom, methyl, second
Base, isopropyl or tertiary butyl.
Preferably, the Ar in the formula (2)1、Ar2、Ar3It is at least one to be selected from following group：
Wherein, R3、R4It is independent to be selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, take
It is generation or unsubstituted anthryl, substituted or unsubstituted ferrosin base, substituted or unsubstituted pyridyl group, substituted or unsubstituted phonetic
Piperidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substitution or
One kind in unsubstituted indyl；R5Selected from hydrogen atom, methyl, ethyl, isopropyl or tertiary butyl.
Preferably, Ar in the formula (2)2、Ar3It is identical, it is selected from following group：
Wherein, R3、R4It is independent to be selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, take
Generation or unsubstituted anthryl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted pyrazine
One kind in base；R5Selected from hydrogen atom, methyl, ethyl, isopropyl or tertiary butyl.
Preferably, the Ar in the formula (2)1Selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution
Or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted acridine
Base, substituted or unsubstituted phenoxazine base, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazine thiophene base, substitution
Or unsubstituted fluorenyl, substituted or unsubstituted carbazyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted ferrosin
It is base, substituted or unsubstituted base, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted
Pyrimidine radicals, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine radical, substitution or
Unsubstituted pyrrole radicals, substituted or unsubstituted benzopyrrole base, substituted or unsubstituted triazolyl, substituted or unsubstituted thiophene
Pheno base, substituted or unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl,
One kind in substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran group.
Most preferably, the one kind of the azepine carbazole compound in following compounds：
Most preferably, the one kind of the compound in triazine class in following compounds：
Formula (1) compound of the present invention can be collectively referred to as route synthesis by following：
Wherein, R1、R2It is independent to be selected from substituted or unsubstituted C1~C30Alkyl, substituted or unsubstituted C6~C30's
Aryl, substituted or unsubstituted C3~C30Heteroaryl in one kind；X1~X4It is independent to be selected from carbon atom or nitrogen-atoms；L is selected from
Singly-bound, substituted or unsubstituted C6~C30Aryl in one kind.
According to the present invention, intermediate A is prepared according to method as follows：
The azepine carbazole of bromo is in nitrogen protection, and palladium, tri-tert-butylphosphine are catalyst, and tertiary butyl sodium alkoxide is alkali, molten
Agent be toluene under conditions of, reacted with bromo-derivative via C-N coupling reactions, obtain intermediate A；
According to the present invention, intermediate B is prepared according to method as follows：
For 2-Chlorobenzimidazole in nitrogen protection, palladium, tri-tert-butylphosphine are catalyst, and tertiary butyl sodium alkoxide is alkali, solvent
Under conditions of toluene, is reacted with bromo-derivative via C-N coupling reactions, obtain intermediate B；
According to the present invention, intermediate C is prepared according to method as follows：
For intermediate B in nitrogen protection, tetra-triphenylphosphine palladium is catalyst, and potassium carbonate is alkali, and tetrahydrofuran is the item of solvent
Under part, intermediate C is obtained by C-C coupling reactions with hypoboric acid compound；
According to the present invention, compound I is prepared according to method as follows：
For intermediate C in nitrogen protection, tetra-triphenylphosphine palladium is catalyst, and potassium carbonate is alkali, and tetrahydrofuran is the item of solvent
Under part, compound I is obtained by C-C coupling reactions with hypoboric acid compound.
Formula (2) compound of the present invention can be collectively referred to as route synthesis by following：
Wherein, Ar1、Ar2、Ar3It is independent to be selected from substituted or unsubstituted C6~C65Aryl, substituted or unsubstituted C3
~C65Heteroaryl in one kind, and it is at least one be selected from following group：
Wherein, R3、R4It is independent to be selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30's
Aryl, substituted or unsubstituted C6~C30Heteroaryl in one kind；R5Selected from hydrogen atom, substituted or unsubstituted C1~C10's
Alkyl, substituted or unsubstituted C6~C30Aryl in one kind.
Above-mentioned synthesis is to be coupled to obtain target via a series of C-C for starting material with 2,4,6- tri- chloro-1,3,5-triazines
Product I, it is recommended to use Suzuki coupling reactions, under nitrogen protection, using tetra-triphenylphosphine palladium as catalyst, potassium carbonate is alkali, four
Hydrogen furans is solvent, and reflux is reacted.
Device architecture of the present invention is most preferably as shown in Figure 1：1/ anode of substrate, 2/ hole injection layer, 3/ hole passes
4/ luminescent layer of defeated layer, 5/ first 6/ second electron transfer layer of electron transfer layer, 7/ electron injecting layer, 8/ cathode 9.Wherein, substrate 1 is
Transparent glass, plastics or quartz；Anode 2 is transparent tin indium oxide ITO or indium zinc oxide IZO；First electron transfer layer 6 is adopted
With the material with unipolarity electron transport property, it is used for the transmission of electronics, is conducive to hole and electronics in the effective multiple of luminescent layer
It closes, film thickness monitoring existsIn range；Second electron transfer layer 7 can be applied to the by deposition or ink ejecting method
On one electron transfer layer, thickness control existsLuminescent layer 6 includes luminescent layer material of main part and object dopant material；
Cathode 9 uses the alloy of Ag or Ag.A kind of organic luminescent device of the present invention can be according to device parameter requirements and material
Characteristic is selected and is combined.To manufacture the organic electroluminescence device of construction same as below：ITO/NPB-DPA/NPB/
AND：A kind of a kind of compound in triazine class of azepine carbazole compound of DPVBi (2wt%)/described/described：Liq/LiF/
Al。
Organic electroluminescence device of the present invention can be widely applied to Display panel, illumination OLED, flexibility OLED, electronics
The fields such as paper, Organophotoreceptor or Organic Thin Film Transistors.
Embodiment 1：The synthesis of compound 1-A1
The synthesis of intermediate A 1-1
By tri-tert-butylphosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium (0.4g,
1.83mmol) and sodium tert-butoxide (22.8g, 238mmol) be added to bromo- 5H- pyridos [4, the 3-B] indoles of 7- (45.2g,
183mmol) and solution of the iodobenzene (37.7g, 185mmol) in degassed toluene (1L), and the mixture is added under reflux
Heat 2 hours.The reaction mixture is cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is dilute
It releases, toluene is used in combination to extract, and merge organic phase, it is evaporated under vacuum.The residue was carried out via silica gel
Filter, and recrystallize.Obtain intermediate A 1-1 (47.2g, yield 80%).
Mass spectrum m/z：323.23 (calculated values：323.19).Theoretical elemental content (%) C17H11N2Br：C,63.18；H,
3.43；Br,24.72；N, 8.67 actual measurement constituent contents (%)：C,63.19；H,3.45；Br,24.72；N,8.64.The above results
Confirm that it is target product to obtain product.
The synthesis of intermediate B 1-1
By tri-tert-butylphosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium (0.4g,
1.83mmol) and sodium tert-butoxide (22.8g, 238mmol) is added to 2-Chlorobenzimidazole (27.8g, 183mmol) and iodobenzene
The solution of (37.7g, 185mmol) in degassed toluene (1L), and the mixture is heated 2 hours under reflux.This is anti-
It answers mixture to be cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, toluene is used in combination to carry
It takes, and merges organic phase, it is evaporated under vacuum.The residue is filtered via silica gel, and is recrystallized.?
To intermediate B 1-1 (33.5g, yield 80%).
Mass spectrum m/z：228.73 (calculated values：228.68).Theoretical elemental content (%) C13H9N2Cl：C,68.28；H,
3.97；Cl,15.50；N, 12.25 actual measurement constituent contents (%)：C,68.27；H,3.97；Cl,15.52；N,12.24.Above-mentioned knot
Fruit confirms that it is target product to obtain product.
The synthesis of intermediate C1-1
Intermediate B 1-1 (9.6g, 42.4mmol) is taken to be added in there-necked flask, addition THF 100mL, nitrogen protection, -78
DEG C stirring 30 minutes, then be added n-BuLi (2.5M) 21mL, react 1 hour, add triisopropyl borate ester 7g, low temperature is anti-
It answers 1 hour, gradually restores room temperature.Last handling process, 2M hydrochloric acid is added in system makes solution pH value be 4-5, stands liquid separation, water layer
It is extracted with ethyl acetate, merges organic layer, be spin-dried for, obtain intermediate C1-1 (8.2g, yield 80%).
Mass spectrum m/z：242.16 (calculated values：242.09).Theoretical elemental content (%) C13H11BN2O2：C,65.59；H,
4.66；B,4.54；N,11.77；O, 13.44 actual measurement constituent contents (%)：C,65.58；H,4.66；B,4.55；N,11.77；O,
13.44.The above results confirm that it is target product to obtain product.
The synthesis of compound 1-A1
By tri-tert-butylphosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium (0.4g,
1.83mmol) and sodium tert-butoxide (22.8g, 238mmol) is added to intermediate A 1-1 (60.4g, 187mmol) and intermediate C1-1
The solution of (44.3g, 183mmol) in degassed toluene (1L), and the mixture is heated 2 hours under reflux.This is anti-
It answers mixture to be cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, toluene is used in combination to carry
It takes, and merges organic phase, it is evaporated under vacuum.The residue is filtered via silica gel, and is recrystallized.?
To compound 1-A1 (67.8g, yield 85%).
Mass spectrum m/z：436.53 (calculated values：436.51).Theoretical elemental content (%) C30H20N4：C,82.55；H,4.62；
N, 12.84 actual measurement constituent contents (%)：C,82.53；H,4.61；N,12.86.The above results confirm that obtain product produces for target
Product.
Embodiment 2：The synthesis of compound 1-B2
The synthesis of intermediate A 1-1
By tri-tert-butylphosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium (0.4g,
1.83mmol) and sodium tert-butoxide (22.8g, 238mmol) be added to bromo- 5H- pyridos [4, the 3-B] indoles of 7- (45.2g,
183mmol) and solution of the iodobenzene (37.7g, 185mmol) in degassed toluene (1L), and the mixture is added under reflux
Heat 2 hours.The reaction mixture is cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is dilute
It releases, toluene is used in combination to extract, and merge organic phase, it is evaporated under vacuum.The residue was carried out via silica gel
Filter, and recrystallize.Obtain intermediate A 1-1 (47.2g, yield 80%).
Mass spectrum m/z：323.23 (calculated values：323.19).Theoretical elemental content (%) C17H11N2Br：C,63.18；H,
3.43；Br,24.72；N, 8.67 actual measurement constituent contents (%)：C,63.19；H,3.45；Br,24.72；N,8.64.The above results
Confirm that it is target product to obtain product.
The synthesis of intermediate B 2-1
By tri-tert-butylphosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium (0.4g,
1.83mmol) and sodium tert-butoxide (22.8g, 238mmol) is added to 2-Chlorobenzimidazole (27.8g, 183mmol) and 2- bromonaphthalenes
The solution of (38.3g, 185mmol) in degassed toluene (1L), and the mixture is heated 2 hours under reflux.This is anti-
It answers mixture to be cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, toluene is used in combination to carry
It takes, and merges organic phase, it is evaporated under vacuum.The residue is filtered via silica gel, and is recrystallized.?
To intermediate B 2-1 (40.7g, yield 80%).
Mass spectrum m/z：278.73 (calculated values：278.74).Theoretical elemental content (%) C17H11N2Cl：C,73.25；H,
3.98；Cl,12.72；N, 10.05 actual measurement constituent contents (%)：C,73.25；H,3.96；Cl,12.74；N,10.05.Above-mentioned knot
Fruit confirms that it is target product to obtain product.
The synthesis of intermediate C2-1
By tri-tert-butylphosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium (0.4g,
1.83mmol) and sodium tert-butoxide (22.8g, 238mmol) is added to two boron of intermediate B 2-1 (50.8g, 183mmol) and Isosorbide-5-Nitrae-benzene
The solution of sour (30.2g, 183mmol) in degassed toluene (1L), and the mixture is heated 2 hours under reflux.It should
Reaction mixture is cooled to room temperature, and is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, toluene is used in combination to carry
It takes, and merges organic phase, it is evaporated under vacuum.The residue is filtered via silica gel, and is recrystallized.?
To intermediate C2-1 (67.8g, yield 85%).
Mass spectrum m/z：314.13 (calculated values：314.15).Theoretical elemental content (%) C19H15BN2O2：C,72.64；H,
4.81；B,3.44；N,8.92；O, 10.19 actual measurement constituent contents (%)：C,72.64；H,4.83；B,3.44；N,8.92；O,
10.17.The above results confirm that it is target product to obtain product.
The synthesis of compound 1-B2
By tri-tert-butylphosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium (0.4g,
1.83mmol) and sodium tert-butoxide (22.8g, 238mmol) is added to intermediate A 1-1 (60.4g, 187mmol) and intermediate C2-1
The solution of (57.5g, 183mmol) in degassed toluene (1L), and the mixture is heated 2 hours under reflux.This is anti-
It answers mixture to be cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, toluene is used in combination to carry
It takes, and merges organic phase, it is evaporated under vacuum.The residue is filtered via silica gel, and is recrystallized.?
To compound 1-B2 (82.3g, yield 80%).
Mass spectrum m/z：562.53 (calculated values：562.66).Theoretical elemental content (%) C40H26N4：C,85.38；H,4.66；
N, 9.96 actual measurement constituent contents (%)：C,85.37；H,4.67；N,9.96.The above results confirm that it is target product to obtain product.
Embodiment 3：The synthesis of compound 2-A1
The synthesis of intermediate a1-1
3,5- dichlorobenzenes (9.4g, 42.4mmol) are taken to be added in there-necked flask, addition THF 100mL, nitrogen protection ,-
78 DEG C are stirred 30 minutes, and n-BuLi (2.5M) 21mL is then added, reacts 1 hour, adds triisopropyl borate ester 14g, low
Temperature reaction 1 hour, gradually restores room temperature.Last handling process, 2M hydrochloric acid is added in system makes solution pH value be 4-5, stands liquid separation,
Aqueous layer with ethyl acetate extracts, and merges organic layer, is spin-dried for, obtains intermediate a1-1 (8.2g, yield 80%).
Mass spectrum m/z：242.16 (calculated values：242.09).Theoretical elemental content (%) C12H12B2O4：C,59.60；H,
5.00；B,8.94；O, 26.46 actual measurement constituent contents (%)：C,59.61；H,5.02；B,8.94；O,26.43.The above results are demonstrate,proved
The real product that obtains is target product.
The synthesis of intermediate a1-2
Tetra-triphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) are added to intermediate a1-1
Bromo- 9, the 9- dimethyl fluorenes (50.3g, 185mmol) of (44.3g, 183mmol) and 2- are molten in degassing tetrahydrofuran (500mL)
Liquid, and the mixture is heated 4 hours under reflux.It filters while hot, obtains a large amount of solids, with solvent dissolved solid, later
Concentration, intermediate a1-2 (50.0g, theoretical value 70%) is obtained via silica gel column chromatography.
Mass spectrum m/z：390.25 (calculated values：390.28).Theoretical elemental content (%) C27H23BO2：C,83.09；H,
5.94；B,2.77；O, 8.20 actual measurement constituent contents (%)：C,83.07；H,5.94；B,2.77；O,8.22.The above results confirm
Acquisition product is target product.
The synthesis of compound 2-A1
Tetra-triphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) are added to intermediate a1-2
(150g, 384mmol) and 2, bis- bromo- 6- phenyl of 4- -1,3,5-triazines (41.3g, 183mmol) is in degassing tetrahydrofuran
Solution in (500mL), and the mixture is heated 4 hours under reflux.It filters while hot, obtains a large amount of solids, use solvent
Dissolved solid concentrates later, and compound 2-A1 (92.9g, theoretical value 60%) is obtained via silica gel column chromatography.
Mass spectrum m/z：846.05 (calculated values：846.07).Theoretical elemental content (%) C63H47N3：C,89.43；H,
5.60；N, 4.97 actual measurement constituent contents (%)：C,89.43；H,5.63；N,4.94.The above results confirm that it is target to obtain product
Product.
Embodiment 4：The synthesis of compound 2-A27
Tetra-triphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) are added to 2- naphthalene boronic acids
(31.5g, 183mmol) and 2,4,6- tri- chloro-1,3,5-triazines (41.8g, 185mmol) are in degassing tetrahydrofuran (500mL)
Solution, and the mixture is heated 4 hours under reflux.It filters while hot, obtains a large amount of solids, with solvent dissolved solid,
It concentrates later, 2,4-, bis- chloro- 6- (naphthalene -2- bases) -1,3,5-triazines (35.3g, theoretical value 70%) is obtained via silica gel column chromatography.
Change bromo- 9, the 9- dimethyl fluorenes of 2- in embodiment 1 into equimolar bromo- 9, the 9- dimethyl fluorenes of 2- tertiary butyls -7-,
2,4- bis- bromo- 6- phenyl -1,3,5-triazines change bis- chloro- 6- of equimolar 2,4- (naphthalene -2- bases) -1,3,5-triazines into, other steps
It is rapid identical as the synthesis of embodiment 1, obtain target product compound A27.Mass spectrum m/z：1255.57 (calculated value：
1255.58).Theoretical elemental content (%) C95H73N3：C,90.80；H,5.86；N, 3.34 actual measurement constituent contents (%)：C,
90.82；H,5.82；N,3.36.The above results confirm that it is target product to obtain product.
Comparative example 1
Transparent anode electrode ito substrate is cleaned by ultrasonic 15 minutes in isopropanol, and is exposed 30 minutes under ultraviolet light,
Then handled 10 minutes with plasma.Then by treated, ito substrate is put into evaporated device.One layer of 60nm's of vapor deposition first
The NPB of 20nm is deposited as hole transmission layer, vapor deposition as hole injection layer, evaporation rate 0.1nm/s in NPB-DPA later
Speed is 0.1nm/s, followed by ADN/DPAVBi, doping concentration 2wt%, host material is deposited in the vapor deposition of luminescent layer, mixing
Evaporation rate be 0.1nm/s, dopant material evaporation rate is 0.002nm/s, evaporation thickness 35nm, and 30nm is then deposited
Alq3As electron transfer layer, evaporation rate 0.1nm/s, vacuum evaporation LiF and Al is used as the moon successively on the electron transport layer
Pole, thickness 200nm.
Application Example：
Transparent anode electrode ito substrate is cleaned by ultrasonic 15 minutes in isopropanol, and is exposed 30 minutes under ultraviolet light,
Then handled 10 minutes with plasma.Then by treated, ito substrate is put into evaporated device.One layer of 60nm's of vapor deposition first
The NPB of 20nm is deposited as hole transmission layer, vapor deposition as hole injection layer, evaporation rate 0.1nm/s in NPB-DPA later
Speed is 0.1nm/s, followed by ADN/DPAVBi, doping concentration 2wt%, host material is deposited in the vapor deposition of luminescent layer, mixing
Evaporation rate be 0.1nm/s, dopant material evaporation rate is 0.002nm/s, evaporation thickness 35nm, and 30nm is deposited later
For the azepine carbazole compound as the first electron transfer layer, the compound in triazine class and the Liq that 30nm is then deposited are total
Evaporation (50:It 50wt%) is used as the second electron transfer layer, evaporation rate 0.05nm/s, vacuum is steamed successively on the electron transport layer
LiF and Al is plated as cathode, thickness 200nm.
Table 1
The above result shows that using the organic luminescent device of the compounds of this invention compared with comparative example 1, show efficiently
The advantages of rate, low driving voltage is organic luminescent device of good performance.
Obviously, the explanation of above example is only intended to facilitate the understanding of the method and its core concept of the invention.It should refer to
Go out, it, without departing from the principle of the present invention, can also be to this hair for the those of ordinary skill of the technical field
Bright some improvement and modification can also be carried out, these improvement and modification are also fallen within the protection scope of the claims of the present invention.
Claims (10)
1. a kind of organic luminescent device includes substrate, anode, hole injection layer, hole transmission layer, luminescent layer, the first electricity successively
Sub- transport layer, the second electron transfer layer, electron injecting layer and cathode, wherein
First electron transfer layer includes the azepine carbazole compound indicated by formula (1), and
Second electron transfer layer includes the compound in triazine class indicated by formula (2)：
Wherein, R1、R2It is independent to be selected from substituted or unsubstituted C1~C30Alkyl, substituted or unsubstituted C6~C30Aryl,
Substituted or unsubstituted C3~C30Heteroaryl in one kind；X1~X4It is independent to be selected from carbon atom or nitrogen-atoms；L be selected from singly-bound,
Substituted or unsubstituted C6~C30Aryl in one kind,
Wherein, Ar1、Ar2、Ar3It is independent to be selected from substituted or unsubstituted C6~C65Aryl, substituted or unsubstituted C3~C65
Heteroaryl in one kind, and it is at least one be selected from following group：
Wherein, R3、R4It is independent to be selected from substituted or unsubstituted C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl,
Substituted or unsubstituted C6~C30Heteroaryl in one kind；R5Selected from hydrogen atom, substituted or unsubstituted C1~C10Alkyl,
Substituted or unsubstituted C6~C30Aryl in one kind.
2. a kind of organic luminescent device according to claim 1, which is characterized in that the X in the formula (1)2、X3In at least
One is nitrogen-atoms, X1、X4For carbon atom.
3. a kind of organic luminescent device according to claim 1, which is characterized in that first electron transfer layer includes
The general formula of azepine carbazole compound is such as shown in (1-1) or (1-2)：
L be selected from singly-bound, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, substitution or
One kind in unsubstituted phenanthryl, substituted or unsubstituted base in the wrong, substituted or unsubstituted triphenylene.
4. a kind of organic luminescent device according to claim 1, which is characterized in that R in the formula (1)1、R2Independent choosing
From methyl, ethyl, isopropyl, tertiary butyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution or unsubstituted
Anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted acridinyl, substitution or
It is unsubstituted phenoxazine base, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazine thiophene base, substituted or unsubstituted
Fluorenyl, substituted or unsubstituted carbazyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted ferrosin base, substitution or not
Substituted base, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substitution
Or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine radical, substituted or unsubstituted pyrroles
Base, substituted or unsubstituted benzopyrrole base, substituted or unsubstituted triazolyl, substituted or unsubstituted thienyl, substitution or
Unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl, substitution or unsubstituted
Dibenzothiophene, one kind in substituted or unsubstituted dibenzofuran group.
5. a kind of organic luminescent device according to claim 1, which is characterized in that Ar in the formula (2)1、Ar2、Ar3Extremely
Few one is selected from following group：
Wherein, R3、R4It is independent selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution or
Unsubstituted anthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, takes substituted or unsubstituted phenanthryl
It is generation or unsubstituted base, substituted or unsubstituted ferrosin base, substituted or unsubstituted pyridyl group, substituted or unsubstituted phonetic
Piperidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine radical, substitution or not
Substituted pyrrole radicals, substituted or unsubstituted benzopyrrole base, substituted or unsubstituted triazolyl, substituted or unsubstituted thiophene
Base, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl, takes substituted or unsubstituted furyl
Generation or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted quinolyl, substitution
Or one kind in unsubstituted isoquinolyl, substituted or unsubstituted indyl；R5Selected from hydrogen atom, methyl, ethyl, isopropyl
Or tertiary butyl.
6. a kind of organic luminescent device according to claim 1, which is characterized in that the Ar in the formula (2)1、Ar2、Ar3
It is at least one to be selected from following group：
Wherein, R3、R4It is independent selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution or
Unsubstituted anthryl, substituted or unsubstituted ferrosin base, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine
Base, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substitution or not
One kind in substituted indyl；R5Selected from hydrogen atom, methyl, ethyl, isopropyl or tertiary butyl.
7. a kind of organic luminescent device according to claim 1, which is characterized in that Ar in the formula (2)2、Ar3It is identical, choosing
From following group：
Wherein, R3、R4It is independent selected from methyl, ethyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution or
In unsubstituted anthryl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted pyrazinyl
One kind；R5Selected from hydrogen atom, methyl, ethyl, isopropyl or tertiary butyl.
8. a kind of organic luminescent device according to claim 1, which is characterized in that the Ar in the formula (2)1Selected from substitution
Or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substitution
Or it is unsubstituted triphenylene, substituted or unsubstituted acridinyl, substituted or unsubstituted phenoxazine base, substituted or unsubstituted
Phenothiazinyl, substituted or unsubstituted phenoxazine thiophene base, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazyl, substitution
Or unsubstituted pyrenyl, substituted or unsubstituted ferrosin base, substituted or unsubstituted base, substituted or unsubstituted acenaphthenyl,
It is substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted pyrazinyl, substituted or unsubstituted
Pyridazinyl, substituted or unsubstituted pyrrole radicals, substituted or unsubstituted benzopyrrole base, takes substituted or unsubstituted triazine radical
Generation or unsubstituted triazolyl, substituted or unsubstituted thienyl, substituted or unsubstituted furyl, substituted or unsubstituted benzene
Bithiophene base, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted two
One kind in benzofuranyl.
9. a kind of organic luminescent device according to claim 1, which is characterized in that the azepine carbazole compound is selected from
One kind in following compounds：
10. a kind of organic luminescent device according to claim 1, which is characterized in that the compound in triazine class is selected from down
State one kind in compound：
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108503636A (en) * | 2018-06-06 | 2018-09-07 | 长春海谱润斯科技有限公司 | A kind of electron transport material and its organic luminescent device |
| CN111747951A (en) * | 2020-05-30 | 2020-10-09 | 浙江华显光电科技有限公司 | Triazine compound and organic light-emitting device thereof |
| WO2022120583A1 (en) * | 2020-12-08 | 2022-06-16 | 京东方科技集团股份有限公司 | Oled device and manufacturing method |
-
2018
- 2018-06-06 CN CN201810573458.4A patent/CN108807707A/en not_active Withdrawn
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108503636A (en) * | 2018-06-06 | 2018-09-07 | 长春海谱润斯科技有限公司 | A kind of electron transport material and its organic luminescent device |
| CN111747951A (en) * | 2020-05-30 | 2020-10-09 | 浙江华显光电科技有限公司 | Triazine compound and organic light-emitting device thereof |
| WO2022120583A1 (en) * | 2020-12-08 | 2022-06-16 | 京东方科技集团股份有限公司 | Oled device and manufacturing method |
| GB2615484A (en) * | 2020-12-08 | 2023-08-09 | Boe Technology Group Co Ltd | OLED device and manufacturing method |
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