CN109096277A - A kind of derivative of phenanthroline and its organic electroluminescence device - Google Patents

A kind of derivative of phenanthroline and its organic electroluminescence device Download PDF

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CN109096277A
CN109096277A CN201811054065.9A CN201811054065A CN109096277A CN 109096277 A CN109096277 A CN 109096277A CN 201811054065 A CN201811054065 A CN 201811054065A CN 109096277 A CN109096277 A CN 109096277A
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derivative
phenanthroline
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蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The invention discloses a kind of derivative of phenanthroline and its organic electroluminescence devices, belong to organic photoelectrical material technical field.Derivative of phenanthroline of the invention is the short of electricity subsystem with big conjugate planes, therefore electron mobility with higher and higher electron affinity show preferable electron-transport and injection efficiency；In addition derivative of phenanthroline of the invention also has certain hole barrier performance.The volume of division center Phen of the invention is larger, effectively raises the glass transition temperature and thermal stability of material, is conducive to material filming.Organic electroluminescence device of the invention includes anode, cathode and organic matter layer, and organic matter layer contains derivative of phenanthroline of the invention between anode and cathode in organic matter layer.Organic electroluminescence device of the invention has lower driving voltage, higher luminous efficiency and luminous brightness, and has longer service life.

Description

A kind of derivative of phenanthroline and its organic electroluminescence device
Technical field
The present invention relates to organic photoelectrical material technical fields, and in particular to a kind of derivative of phenanthroline and its organic electroluminescence Luminescent device.
Background technique
Organic photoelectrical material is the organic material of the generation with photon and electronics, conversion and transmission characteristic.Currently, organic Photoelectric material has been applied to organic electroluminescence device (Organic Light-Emitting Diode, OLED).OLED is Refer to the device that organic photoelectrical material shines under the action of electric current or electric field, electric energy can be converted into luminous energy by it.In recent years Carry out OLED just to receive more and more attention as FPD of new generation and solid state lighting technology.Compared to liquid crystal display skill Art, OLED are shone with its low-power consumption, actively, fast response time, high contrast, no angle limit, can make the spies such as Flexible Displays Point is increasingly used in display and lighting area.
Usual OLED has a multilayered structure, including tin indium oxide (ITO) anode and metallic cathode and be placed in ito anode with Organic matter layer between metallic cathode, such as hole injection layer (HIL), hole transmission layer (HTL), luminescent layer (EML), electron-transport Layer (ETL) and electron injecting layer (EIL) etc..Under certain voltage driving, hole is injected by anode and cathode respectively with electronics Hole transmission layer and electron transfer layer, the two passes through hole transmission layer respectively and electron transfer layer moves to luminescent layer, works as the two It meeting in luminescent layer and forms hole-electron compound exciton when combining, exciton returns to ground state by way of luminescence relaxation, thus Achieve the purpose that luminous.
As the electron transfer layer in OLED, basic role is to improve the efficiency of transmission of electronics in the devices, is dropped simultaneously Energy barrier of the low electronics in injection process, improves the injection efficiency of electronics, so that it is determined that OLED has more stable use Performance.For hole blocking layer, basic role is that hole is effectively blocked in luminescent layer, realizes carrier most It is big compound, to realize that the effective of OLED shines.
Currently, the hole mobility for the hole mobile material being applied in OLED is typically much deeper than the electricity of electron transport material Transport factor, this can directly result in being remarkably decreased for OLED performance.It is embodied in, operation voltage is high, luminous efficiency is low, uses The problems such as service life is short, therefore, design electron transport material with excellent performance or hole barrier materials have it is stronger Realistic meaning.
Summary of the invention
Goal of the invention: in view of the above-mentioned problems, the object of the present invention is to provide a kind of derivative of phenanthroline and its Organic Electricities Electroluminescence device, the derivative of phenanthroline are applied as electron transport material or hole barrier materials in organic electroluminescent In device, to reduce the driving voltage of organic electroluminescence device, the luminous efficiency of organic electroluminescence device is improved And brightness, and extend the service life of organic electroluminescence device.
Above-mentioned technical purpose of the invention is achieved through the following technical solutions: a kind of derivative of phenanthroline, described Derivative of phenanthroline has the general structure as shown in structural formula I:
Wherein, the R1、R2、R3、R4It is independent selected from hydrogen, substituted or unsubstituted C1~C20 alkyl, replace or not One of the aryl of substituted C6~C30, heteroaryl of substituted or unsubstituted C3~C30；
The L1、L2The independent arlydene selected from substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 One of inferior heteroaryl.
Preferably, the R1、R2、R3、R4It is independent to be selected from one of group as shown below,
Wherein, the X is selected from C (R)2、Si(R)2, O or S, the R be selected from the alkane of substituted or unsubstituted C1~C10 One of base, the aryl of substituted or unsubstituted C6~C18, heteroaryl of substituted or unsubstituted C3~C18；
The X1、X2、X3、X4、X5、X6、X7、X8It is independent to be selected from C (R0) or N, the R0Selected from hydrogen, replaces or do not take The alkyl of the C1~C10 in generation, the aryl of substituted or unsubstituted C6~C18, substituted or unsubstituted C3~C18 heteroaryl in One kind；
The L is selected from the Asia of singly-bound, the arlydene of substituted or unsubstituted C6~C18, substituted or unsubstituted C3~C18 One of heteroaryl.
Preferably, the R is selected from methyl, ethyl, propyl, butyl, amyl, phenyl, pyridyl group, pyrimidine radicals, pyrazinyl, rattles away One of piperazine base, triazine radical, naphthalene, quinolyl, xenyl, furyl, thienyl；
The R0Selected from hydrogen, methyl, ethyl, propyl, butyl, amyl, phenyl, pyridyl group, pyrimidine radicals, pyrazinyl, pyridazine One of base, triazine radical, naphthalene, quinolyl, xenyl, terphenyl, triphenylene, furyl, thienyl.
Preferably, the L is selected from singly-bound, phenylene, sub-pyridyl group, sub- pyrimidine radicals, sub- pyrazinyl, sub- pyridazinyl, sub- naphthalene One of base, sub- quinolyl, biphenylene.
Preferably, the L1、L2It is independent to be selected from one of group as shown below,
Wherein, the R5、R6、R7、R8、R9、R10、R11、R12、R13、R14It is independent to be selected from hydrogen, methyl, ethyl, propyl, fourth Base, amyl, phenyl, pyridyl group, pyrimidine radicals, pyrazinyl, pyridazinyl, triazine radical, naphthalene, quinolyl, xenyl, fluorenyl, Sanya One of phenyl, dibenzofuran group.
Preferably, the R1、R2、R3、R4It is independent to be selected from one of group as shown below,
Preferably, the L1、L2It is independent to be selected from one of group as shown below,
Most preferably, the derivative of phenanthroline is selected from one of chemical structure as follows,
Further, the present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device includes Anode, cathode and organic matter layer, for the organic matter layer between anode and cathode, the organic matter layer contains above-mentioned hair Bright derivative of phenanthroline.
Preferably, the organic matter layer includes electron transfer layer perhaps the hole blocking layer electron transfer layer or sky Cave barrier layer includes the derivative of phenanthroline of aforementioned present invention.
The utility model has the advantages that compared with prior art, the triazine and division center in derivative of phenanthroline of the invention are adjacent Phenanthroline all has stronger electrophilic characteristic, and total system has preferable coplanarity, for big conjugation The short of electricity subsystem of plane, therefore electron mobility with higher and higher electron affinity, show preferable electronics Transmission and injection efficiency；In addition derivative of phenanthroline of the invention also has certain hole barrier performance, can be effective Hole is limited in light emitting region, realizes that the effective of device shines.The volume of division center Phen of the invention is larger, The glass transition temperature and thermal stability for effectively raising material, are conducive to material filming.Spread out using Phen of the invention Organic luminescent device of the biology as organic matter layer has lower driving voltage, higher luminous efficiency, and has longer Service life.
Specific embodiment
Combined with specific embodiments below, the present invention is furture elucidated, it should be understood that these embodiments are merely to illustrate the present invention Rather than limit the scope of the invention, after the present invention has been read, those skilled in the art are to various equivalences of the invention The modification of form is fallen in protection scope required by the application.
A kind of derivative of phenanthroline, the derivative of phenanthroline have the general structure as shown in structural formula I:
Wherein, the R1、R2、R3、R4It is independent selected from hydrogen, substituted or unsubstituted C1~C20 alkyl, replace or not One of the aryl of substituted C6~C30, heteroaryl of substituted or unsubstituted C3~C30；
The L1、L2The independent arlydene selected from substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 One of inferior heteroaryl.
Preferably, the R1、R2、R3、R4It is independent to be selected from one of group as shown below,
Wherein, the X is selected from C (R)2、Si(R)2, O or S, the R be selected from the alkane of substituted or unsubstituted C1~C10 One of base, the aryl of substituted or unsubstituted C6~C18, heteroaryl of substituted or unsubstituted C3~C18；
The X1、X2、X3、X4、X5、X6、X7、X8It is independent to be selected from C (R0) or N, the R0Selected from hydrogen, replaces or do not take The alkyl of the C1~C10 in generation, the aryl of substituted or unsubstituted C6~C18, substituted or unsubstituted C3~C18 heteroaryl in One kind；
The L is selected from the Asia of singly-bound, the arlydene of substituted or unsubstituted C6~C18, substituted or unsubstituted C3~C18 One of heteroaryl.
Preferably, the R is selected from methyl, ethyl, propyl, butyl, amyl, phenyl, pyridyl group, pyrimidine radicals, pyrazinyl, rattles away One of piperazine base, triazine radical, naphthalene, quinolyl, xenyl, furyl, thienyl；
The R0Selected from hydrogen, methyl, ethyl, propyl, butyl, amyl, phenyl, pyridyl group, pyrimidine radicals, pyrazinyl, pyridazine One of base, triazine radical, naphthalene, quinolyl, xenyl, terphenyl, triphenylene, furyl, thienyl.
Preferably, the L is selected from singly-bound, phenylene, sub-pyridyl group, sub- pyrimidine radicals, sub- pyrazinyl, sub- pyridazinyl, sub- naphthalene One of base, sub- quinolyl, biphenylene.
Preferably, the L1、L2It is independent to be selected from one of group as shown below,
Wherein, the R5、R6、R7、R8、R9、R10、R11、R12、R13、R14It is independent to be selected from hydrogen, methyl, ethyl, propyl, fourth Base, amyl, phenyl, pyridyl group, pyrimidine radicals, pyrazinyl, pyridazinyl, triazine radical, naphthalene, quinolyl, xenyl, fluorenyl, Sanya One of phenyl, dibenzofuran group.
Preferably, the R1、R2、R3、R4It is independent to be selected from one of group as shown below,
Preferably, the L1、L2It is independent to be selected from one of group as shown below,
According to the present invention, the substituent group on abovementioned alkyl is selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, nitro；Alternatively, The alkyl of C1~C10, for example, methyl, ethyl, propyl, butyl, amyl, cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl etc.；Or Person, the alkoxy of C1~C10, for example, methoxyl group, ethyoxyl, propoxyl group, butoxy, amoxy etc.；Alternatively, the virtue of C6~C24 Base, for example, phenyl, naphthalene, phenanthryl, fluorenyl etc.；Alternatively, the heteroaryl of C3~C24, for example, pyridyl group, pyrimidine radicals, triazine radical, Quinolyl, furyl, thienyl, dibenzofuran group, dibenzothiophene, carbazyl etc..
Substituent group on above-mentioned aryl, heteroaryl is independent selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, nitro；Or Person, the alkyl of C1~C10, for example, methyl, ethyl, propyl, butyl, amyl, cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl etc.； Alternatively, the alkoxy of C1~C10, for example, methoxyl group, ethyoxyl, propoxyl group, butoxy, amoxy etc.；Alternatively, C6~C24 Aryl, for example, phenyl, naphthalene, xenyl, phenanthryl, terphenyl, anthryl, triphenylene, fluorenyl etc.；Alternatively, C3~C24 Heteroaryl, for example, pyridyl group, pyrimidine radicals, triazine radical, quinolyl, furyl, thienyl, dibenzofuran group, dibenzothiophenes Base, carbazyl etc..
Substituent group on above-mentioned arlydene, inferior heteroaryl is independent selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, nitro； Alternatively, the alkyl of C1~C10, for example, methyl, ethyl, propyl, butyl, amyl, cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl Deng；Alternatively, the alkoxy of C1~C10, for example, methoxyl group, ethyoxyl, propoxyl group, butoxy, amoxy etc.；Alternatively, C6~ The aryl of C24, for example, phenyl, naphthalene, xenyl, phenanthryl, terphenyl, anthryl, triphenylene, fluorenyl etc.；Alternatively, C3~ The heteroaryl of C24, for example, pyridyl group, pyrimidine radicals, triazine radical, quinolyl, furyl, thienyl, dibenzofuran group, hexichol Bithiophene base, carbazyl etc..
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 refers to remove a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule after, be left the total of univalent perssad 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 aromatic core carbon in aryl are substituted by hetero atom General name, the hetero atom include but is 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.
Arlydene of the present invention refers to remove two hydrogen atoms on the aromatic core carbon of aromatic hydrocarbon molecule after, be left univalent perssad General name, can be monocycle arlydene or condensed ring arlydene, example may include phenylene, biphenylene, naphthylene, anthrylene, Phenanthrylene or sub- pyrenyl etc., but not limited to this.
Inferior heteroaryl of the present invention refers to the base that one or more aromatic core carbon in arlydene are substituted by hetero atom The general name of group, the hetero atom include but is not limited to oxygen, sulphur or nitrogen-atoms, the heteroarylidene can for monocycle heteroarylidene or Condensed ring heteroarylidene, example may include sub-pyridyl group, sub- pyrrole radicals, sub-pyridyl group, sub- thienyl, furylidene, sub- indyl, Sub- quinolyl, sub- isoquinolyl, sub- benzothienyl, sub- benzofuranyl, sub- dibenzofuran group, sub- dibenzothiophene, Sub- carbazyl etc., but not limited to this.
The alkyl of substituted or unsubstituted C1~C20 of the present invention, substituted or unsubstituted C6~C30 aryl, take The heteroaryl of generation or unsubstituted C3~C30 refer to be substituted before alkyl, aryl, heteroaryl the total number of carbon atoms be respectively 1~ 20,6~30,3~30, and so on.
Chain-like alkyl of the carbon atom numbers such as propyl of the present invention, butyl, amyl greater than two includes their isomers, such as Isopropyl, isobutyl group, sec-butyl, tert-butyl, isopentyl, neopentyl, tertiary pentyl etc., but not limited to this.
As an example, it is not particularly limited, derivative of phenanthroline of the present invention is selected from chemical structure as follows One of,
The synthetic route of derivative of phenanthroline of the invention is as follows:
It is obtained by reaction
It is obtained by reaction
It is obtained by carbon carbon coupling reactionAbove-mentioned centre Product andTarget product shown in structural formula I is obtained by carbon carbon coupling reaction.
The R1、R2、R3、R4、L1、L2As defined above.
The synthetic route of derivative of phenanthroline of the invention is not particularly limited, those skilled in the art can be used Known popular response.
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device include anode, cathode with And organic matter layer, for the organic matter layer between anode and cathode, the organic matter layer contains the adjacent Féraud of aforementioned present invention Quinoline derivant.
The organic matter layer of organic electroluminescence device of the invention can have single layer structure, or with two layers or more Multilayered structure.The organic matter layer of organic electroluminescence device of the invention may include hole injection layer, hole transmission layer, electronics Barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer are placed between anode and hole injection layer Any one layer or any multilayer in buffer layer.The thickness of organic matter layer of the invention is not higher than 6 μm, preferably not higher than 0.5 μm, and more preferably 0.02~0.5 μm.
In organic electroluminescence device of the invention, derivative of phenanthroline shown in structural formula I can be used for above-mentioned having Perhaps any multilayer preferably contains in electron transfer layer or hole blocking layer any one layer in machine nitride layer.Content does not have There is special limitation, can according to need appropriate adjustment.
Organic electroluminescence device of the invention is preferred are as follows:
Substrate/ito anode/hole transmission layer/luminescent layer/electron transfer layer/metallic cathode；Alternatively,
Substrate/ito anode/hole transmission layer/luminescent layer/electron transfer layer/electron injecting layer/metallic cathode；Alternatively,
Substrate/ito anode/hole injection layer/hole transmission layer/luminescent layer/electron transfer layer/metallic cathode；Alternatively,
Substrate/ito anode/hole transmission layer/luminescent layer/hole blocking layer/electron transfer layer/metallic cathode；Alternatively,
Substrate/ito anode/hole injection layer/hole transmission layer/luminescent layer/electron transfer layer/electron injecting layer/metal Cathode；Alternatively,
Substrate/ito anode/hole transmission layer/luminescent layer/hole blocking layer/electron transfer layer/electron injecting layer/metal Cathode, alternatively,
Substrate/ito anode/hole injection layer/hole transmission layer/luminescent layer/hole blocking layer/electron transfer layer/metal Cathode, alternatively,
Substrate/ito anode/hole injection layer/hole transmission layer/luminescent layer/hole blocking layer/electron transfer layer/electronics Implanted layer/metallic cathode.
Organic electroluminescence device of the invention can be used known materials and be prepared by known methods, however, Organic Electricity The structure of electroluminescence device is without being limited thereto.
Substrate of the present invention, the substrate of translucency preferably with higher, for example, glass plate, quartz plate, polymer Plate etc., but not limited to this.
Anode of the present invention, preferably with the material of higher work-functions, such as the oxidation of zinc oxide, indium oxide, indium tin The oxides such as object (ITO), indium-zinc oxide (IZO)；The metals such as Ag, Au, Al, Cu, Ni, Mo, Ti, Zn, Pd, Pt or its conjunction Gold；The electroconductive polymers such as polyaniline, polypyrrole；Carbon black etc., but not limited to this.In addition, anode can be single layer structure, it can also To be two layers or more of multilayered structure, the anode material that each layer is included can be homogenous material, be also possible to mixing material.
Cathode of the present invention preferably has compared with the metals such as the material, such as Ag, Al, Mg, Ti of low work function or its conjunction Gold, but not limited to this.In addition, cathode can be single layer structure, it is also possible to two layers or more of multilayered structure, each layer is included Cathode material can be homogenous material, be also possible to mixing material.
Hole-injecting material of the invention preferably has the material of preferable hole injection efficiency, for example, molybdenum oxide, Titanium oxide, silver oxide, triarylamine derivative, benzidine derivative, phthalocyanine derivates, naphthalocyanine derivative, porphyrin are derivative Object, polyvinyl carbazole, polysilane, electroconductive polymer etc., but not limited to this.In addition, hole injection layer can be single layer knot Structure is also possible to two layers or more of multilayered structure, and the hole-injecting material that each layer is included can be homogenous material, can also be with It is mixing material.
Hole mobile material of the invention, preferably with the material of preferable hole transport performance, for example, triaryl amine is derivative Object, benzidine derivative, carbazole derivates, anthracene derivant, poly- (N- vinyl carbazole) (abbreviation PVK), poly- (4- vinyl triphen Amine) (referred to as: PVTPA) etc., but not limited to this.In addition, hole transmission layer can be single layer structure, it is also possible to two layers or more Multilayered structure, the hole mobile material that each layer is included can be homogenous material, be also possible to mixing material.
Luminescent layer of the invention, may include a kind of material, also may include two or more mixing materials, preferably comprises The mixing material of main body and doping, the dopant material include fluorescence luminescent material and phosphorescent light-emitting materials.The fluorescence radiation Material includes blue-fluorescence luminescent material, for example, pyrene derivatives,Derivative, fluoranthene derivative, fluorene derivative, triaryl amine spread out Biology etc., green fluorescence luminescent material, for example, carbazole derivates, triarylamine derivative etc., red fluorescence luminescent material, such as Carbazole derivates, triarylamine derivative etc..The phosphorescent light-emitting materials include blue phosphorescent luminescent material, for example, complex of iridium, Platinum complex, osmium complex etc., green phosphorescent luminescent material, for example, complex of iridium etc., red phosphorescent luminescent material, for example, iridium Complex, platinum complex, europium complex etc..The material of main part, the lowest unoccupied molecular orbital energy level preferably compared with dopant material Material high, HOMO highest occupied molecular orbital energy level is low, for example, aluminum complex, carbazole derivates, anthracene derivant, benzimidizole derivatives, Triarylamine derivative etc..But not limited to this.
Electron transport material of the invention preferably has the material of preferable electronic transmission performance, for example, aluminum complex, Zn complex, imdazole derivatives, benzimidizole derivatives, pyrrolotriazine derivatives, derivative of phenanthroline etc., but not limited to this.Separately Outside, electron transfer layer can be single layer structure, be also possible to two layers or more of multilayered structure, the electron-transport that each layer is included Material can be homogenous material, be also possible to mixing material.
Electron injection material of the invention, preferably with the material of preferable electron injection performance, for example, alkali metal, alkali Earth metal, the compound containing alkali metal, compound containing alkaline-earth metal etc., but not limited to this.In addition, electron injecting layer can To be single layer structure, it is also possible to two layers or more of multilayered structure, the electron injection material that each layer is included can be single Material is also possible to mixing material.
It to the forming method of each layer of organic electroluminescence device of the invention, is not particularly limited, dry type can be used Method well known to membrane formation process, wet type membrane formation etc..Dry type membrane formation process includes vacuum vapour deposition, sputtering method, plasma method etc..Wet type Membrane formation process includes spin-coating method, infusion process, ink-jet method etc., but not limited to this.
Organic electroluminescence device of the invention can be widely applied to FPD, solid state lighting, Organophotoreceptor or have The fields such as machine thin film transistor (TFT).
The present invention is not particularly limited raw material employed in following embodiment, can be for commercial product or using this Preparation method known to the technical staff of field is prepared.
Synthetic example 1: the preparation of compound TM1
Sequentially added into reaction flask compound E1 (41.4g, 106.6mmol), connection boric acid pinacol ester (29.8g, 117.3mmol)、KOAc(31.4g,319.8mmol)、Pd(dba)2(1.7g,3mmol)、PCy3(1.7g, 6mmol) and two evils Alkane (500ml) stirs 12 hours under conditions of reflux.After reaction, it is cooled to room temperature, filters, be spin-dried for filtrate and obtain slightly Crude product chloroform/re-crystallizing in ethyl acetate is obtained compound F1 (37.1g, 80%) by product.
Compound F1 (19.2g, 44.2mmol), the bromo- 1,10- phenanthroline of 5,6- bis- are sequentially added into reaction flask (7.47g,22.1mmol)、Pd(PPh3)4(0.81g,0.7mmol)、K2CO3(6.11g,44.2mmol)、THF(110ml)、H2O (55ml) is stirred 12 hours under conditions of reflux.After reaction, it is cooled to room temperature, is extracted with dichloromethane, dry, mistake Filter, crude product obtain compound TM1 (11.8g, 67%) through column chromatographic purifying.Mass spectrum m/z: theoretical value: 794.92；Measured value: 794.28.Theoretical elemental content (%) C54H34N8: C, 81.59；H,4.31；N,14.10；Constituent content (%): C is surveyed, 81.56；H,4.36；N,14.08.The above results confirm that obtaining product is target product.
Synthetic example 2: the preparation of compound TM5
In the preparation method of the compound TM1 in synthetic example 1, compound E1 is changed into equimolar compound E2, other steps are identical, obtain compound TM5 (15.1g, 72%).Mass spectrum m/z: theoretical value: 947.12；Measured value: 946.33.Theoretical elemental content (%) C66H42N8: C, 83.70；H,4.47；N,11.83；Constituent content (%): C is surveyed, 83.67；H,4.52；N,11.81.The above results confirm that obtaining product is target product.
Synthetic example 3: the preparation of compound TM12
In the preparation method of the compound TM1 in synthetic example 1, compound E1 is changed into equimolar compound E3, other steps are identical, obtain compound TM12 (15.2g, 69%).Mass spectrum m/z: theoretical value: 995.16；Measured value: 994.36.Theoretical elemental content (%) C70H42N8: C, 84.49；H,4.25；N,11.26；Constituent content (%): C is surveyed, 84.47；H,4.28；N,11.25.The above results confirm that obtaining product is target product.
Synthetic example 4: the preparation of compound TM14
In the preparation method of the compound TM1 in synthetic example 1, compound E1 is changed into equimolar compound E4, other steps are identical, obtain compound TM14 (14.7g, 70%).Mass spectrum m/z: theoretical value: 949.09；Measured value: 948.36.Theoretical elemental content (%) C64H40N10: C, 80.99；H,4.25；N,14.76；Constituent content (%): C is surveyed, 80.95；H,4.30；N,14.75.The above results confirm that obtaining product is target product.
Synthetic example 5: the preparation of compound TM19
In the preparation method of the compound TM1 in synthetic example 1, compound E1 is changed into equimolar compound E5, other steps are identical, obtain compound TM19 (16.2g, 75%).Mass spectrum m/z: theoretical value: 975.08；Measured value: 974.31.Theoretical elemental content (%) C66H38N8O2: C, 81.30；H,3.93；N,11.49；O,3.28；Survey constituent content (%): C, 81.28；H,3.99；N,11.48；O,3.25.The above results confirm that obtaining product is target product.
Synthetic example 6: the preparation of compound TM27
In the preparation method of the compound TM1 in synthetic example 1, compound E1 is changed into equimolar compound E6, other steps are identical, obtain compound TM27 (16.9g, 65%).Mass spectrum m/z: theoretical value: 1179.44；Measured value: 1178.46.Theoretical elemental content (%) C84H58N8: C, 85.54；H,4.96；N,9.50；Constituent content (%): C is surveyed, 85.52；H,4.99；N,9.49.The above results confirm that obtaining product is target product.
Synthetic example 7: the preparation of compound TM29
In the preparation method of the compound TM1 in synthetic example 1, compound E1 is changed into equimolar compound E7, other steps are identical, obtain compound TM29 (11.8g, 67%).Mass spectrum m/z: theoretical value: 794.92；Measured value: 794.29.Theoretical elemental content (%) C54H34N8: C, 81.59；H,4.31；N,14.10；Constituent content (%): C is surveyed, 81.56；H,4.36；N,14.8.The above results confirm that obtaining product is target product.
Synthetic example 8: the preparation of compound TM32
In the preparation method of the compound TM1 in synthetic example 1, compound E1 is changed into equimolar compound E8, other steps are identical, obtain compound TM32 (15.3g, 73%).Mass spectrum m/z: theoretical value: 947.12；Measured value: 946.32.Theoretical elemental content (%) C66H42N8: C, 83.70；H,4.47；N,11.83；Constituent content (%): C is surveyed, 83.67；H,4.52；N,11.81.The above results confirm that obtaining product is target product.
Synthetic example 9: the preparation of compound TM44
In the preparation method of the compound TM1 in synthetic example 1, compound E1 is changed into equimolar compound E9, other steps are identical, obtain compound TM44 (14.2g, 66%).Mass spectrum m/z: theoretical value: 975.08；Measured value: 974.31.Theoretical elemental content (%) C66H38N8O2: C, 81.30；H,3.93；N,11.49；O,3.28；Survey constituent content (%): C, 81.29；H,3.98；N,11.47；O,3.27.The above results confirm that obtaining product is target product.
Synthetic example 10: the preparation of compound TM53
In the preparation method of the compound TM1 in synthetic example 1, compound E1 is changed into equimolar compound E10, other steps are identical, obtain compound TM53 (14.6g, 74%).Mass spectrum m/z: theoretical value: 895.04；Measured value: 894.31.Theoretical elemental content (%) C62H38N8: C, 83.20；H,4.28；N,12.52；Constituent content (%): C is surveyed, 83.18；H,4.31；N,12.51.The above results confirm that obtaining product is target product.
Synthetic example 11: the preparation of compound TM80
In the preparation method of the compound TM1 in synthetic example 1, compound E1 is changed into equimolar compound E11, other steps are identical, obtain compound TM80 (14.8g, 64%).Mass spectrum m/z: theoretical value: 1047.24；Measured value: 1046.36.Theoretical elemental content (%) C74H46N8: C, 84.87；H,4.43；N,10.70；Constituent content (%): C is surveyed, 84.84；H,4.47；N,10.69.The above results confirm that obtaining product is target product.
Synthetic example 12: the preparation of compound TM81
In the preparation method of the compound TM1 in synthetic example 1, compound E1 is changed into equimolar compound E12, other steps are identical, obtain compound TM81 (14.0g, 71%).Mass spectrum m/z: theoretical value: 895.04；Measured value: 894.35.Theoretical elemental content (%) C62H38N8: C, 83.20；H,4.28；N,12.52；Constituent content (%): C is surveyed, 83.17；H,4.33；N,12.50.The above results confirm that obtaining product is target product.
Synthesis implementation 13: the preparation of compound TM93
In the preparation method of the compound TM1 in synthetic example 1, compound E1 is changed into equimolar compound E13, other steps are identical, obtain compound TM93 (13.2g, 63%).Mass spectrum m/z: theoretical value: 947.12；Measured value: 946.33.Theoretical elemental content (%) C66H42N8: C, 83.70；H,4.47；N,11.83；Constituent content (%): C is surveyed, 83.67；H,4.53；N,11.80.The above results confirm that obtaining product is target product.
Synthetic example 14: the preparation of compound TM101
In the preparation method of the compound TM1 in synthetic example 1, compound E1 is changed into equimolar compound E14, other steps are identical, obtain compound TM101 (14.4g, 69%).Mass spectrum m/z: theoretical value: 947.12；Measured value: 946.37.Theoretical elemental content (%) C66H42N8: C, 83.70；H,4.47；N,11.83；Constituent content (%): C is surveyed, 83.68；H,4.51；N,11.81.The above results confirm that obtaining product is target product.
Synthetic example 15: the preparation of compound TM113
In the preparation method of the compound TM1 in synthetic example 1, compound E1 is changed into equimolar compound E15, other steps are identical, obtain compound TM113 (17.5g, 72%).Mass spectrum m/z: theoretical value: 1101.29；Measured value: 1100.40.Theoretical elemental content (%) C76H48N10: C, 82.89；H,4.39；N,12.72；Constituent content (%): C is surveyed, 82.86；H,4.43；N,12.71.The above results confirm that obtaining product is target product.
Other target products are synthesized referring to the synthetic method of above-described embodiment 1-15.
Application Example 1: the preparation of organic electroluminescence device 1
Selection ito glass is anode, dries after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, above-mentioned Vacuum evaporation 2T-NATA is as hole injection layer, evaporation thickness 10nm in anode grid substrate.The vacuum evaporation on hole injection layer NPB is as hole transmission layer, evaporation thickness 30nm.The visitor of vacuum evaporation material of main part ADN on the hole transport layer, 2wt% Body material DPAVBi, as luminescent layer, evaporation thickness 45nm.Vacuum evaporation the compound of the present invention TM1 makees on the light-emitting layer For electron transfer layer, evaporation thickness 40nm.As electron injecting layer, evaporation thickness is vapor deposition LiF on the electron transport layer 0.5nm.Vacuum evaporation Al is as cathode, evaporation thickness 150nm on electron injecting layer.
Application Example 2: the preparation of organic electroluminescence device 2
Change the compound TM1 in Application Example 1 into compound TM5, other steps are identical.
Application Example 3: the preparation of organic electroluminescence device 3
Change the compound TM1 in Application Example 1 into compound TM12, other steps are identical.
Application Example 4: the preparation of organic electroluminescence device 4
Change the compound TM1 in Application Example 1 into compound TM14, other steps are identical.
Application Example 5: the preparation of organic electroluminescence device 5
Change the compound TM1 in Application Example 1 into compound TM19, other steps are identical.
Comparative example 1:
Selection ito glass is anode, dries after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, above-mentioned Vacuum evaporation 2T-NATA is as hole injection layer, evaporation thickness 10nm in anode grid substrate.The vacuum evaporation on hole injection layer NPB is as hole transmission layer, evaporation thickness 30nm.The visitor of vacuum evaporation material of main part AND on the hole transport layer, 2wt% Body material DPAVBi, as luminescent layer, evaporation thickness 45nm.Vacuum evaporation vacuum evaporation Alq on the light-emitting layer3As electronics Transport layer, evaporation thickness 40nm.Vapor deposition LiF is as electron injecting layer, evaporation thickness 0.5nm on the electron transport layer.? Vacuum evaporation Al is as cathode, evaporation thickness 150nm on electron injecting layer.
The characteristics of luminescence of organic electroluminescence device prepared by Application Example 1-5 of the present invention and comparative example 1 is surveyed Test result is as shown in table 1.
Table 1
Application Example 6: the preparation of organic electroluminescence device 6
Selection ito glass is anode, dries after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, above-mentioned Vacuum evaporation 2T-NATA is as hole injection layer, evaporation thickness 10nm in anode grid substrate.The vacuum evaporation on hole injection layer NPB is as hole transmission layer, evaporation thickness 30nm.The visitor of vacuum evaporation material of main part CBP on the hole transport layer, 10wt% Body material Ir (ppy)3, as luminescent layer, evaporation thickness 30nm.Vacuum evaporation the compound of the present invention TM27 on the light-emitting layer As electron transfer layer, evaporation thickness 35nm.For vacuum evaporation LiF as electron injecting layer, vapor deposition is thick on the electron transport layer Degree is 0.2nm.Vacuum evaporation Al is as cathode, evaporation thickness 100nm on electron injecting layer.
Application Example 7: the preparation of organic electroluminescence device 7
Change the compound TM27 in Application Example 6 into compound TM29, other steps are identical.
Application Example 8: the preparation of organic electroluminescence device 8
Change the compound TM27 in Application Example 6 into compound TM32, other steps are identical.
Application Example 9: the preparation of organic electroluminescence device 9
Change the compound TM27 in Application Example 6 into compound TM44, other steps are identical.
Application Example 10: the preparation of organic electroluminescence device 10
Change the compound TM27 in Application Example 6 into compound TM53, other steps are identical.
Comparative example 2:
Selection ito glass is anode, dries after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, above-mentioned Vacuum evaporation 2T-NATA is as hole injection layer, evaporation thickness 10nm in anode grid substrate.The vacuum evaporation on hole injection layer NPB is as hole transmission layer, evaporation thickness 30nm.The visitor of vacuum evaporation material of main part CBP on the hole transport layer, 10wt% Body material Ir (ppy)3, as luminescent layer, evaporation thickness 30nm.Vacuum evaporation Alq on the light-emitting layer3As electron transfer layer, Evaporation thickness is 35nm.Vacuum evaporation LiF is as electron injecting layer, evaporation thickness 0.2nm on the electron transport layer.In electronics Vacuum evaporation Al is as cathode, evaporation thickness 100nm on implanted layer.
The characteristics of luminescence of organic electroluminescence device prepared by Application Example 6-10 of the present invention and comparative example 2 Test result is as shown in table 2.
Table 2
Application Example 11: the preparation of organic electroluminescence device 11
Selection ito glass is anode, dries after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, above-mentioned Vacuum evaporation NPB is as hole transmission layer, evaporation thickness 30nm in anode grid substrate.Vacuum evaporation main body on the hole transport layer The guest materials (piq) of material C BP, 10wt%2Ir (acac), as luminescent layer, evaporation thickness 30nm.It is true on the light-emitting layer Sky vapor deposition the compound of the present invention TM80 is as electron transfer layer, evaporation thickness 20nm.Vacuum evaporation on the electron transport layer LiF is as electron injecting layer, evaporation thickness 0.5nm.Vacuum evaporation Al is as cathode, evaporation thickness on electron injecting layer 100nm。
Application Example 12: the preparation of organic electroluminescence device 12
Change the compound TM80 in Application Example 11 into compound TM81, other steps are identical.
Application Example 13: the preparation of organic electroluminescence device 13
Change the compound TM80 in Application Example 11 into compound TM93, other steps are identical.
Application Example 14: the preparation of organic electroluminescence device 14
Change the compound TM80 in Application Example 11 into compound TM101, other steps are identical.
Application Example 15: the preparation of organic electroluminescence device 15
Change the compound TM80 in Application Example 11 into compound TM113, other steps are identical.
Comparative example 3:
Selection ito glass is anode, dries after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, above-mentioned Vacuum evaporation NPB is as hole transmission layer, evaporation thickness 30nm in anode grid substrate.Vacuum evaporation CBP on the hole transport layer As luminous layer main body, 10% (piq)2Ir (acac) is as doping, evaporation thickness 30nm.Vacuum evaporation on the light-emitting layer Alq3As electron transfer layer, evaporation thickness 20nm.Vacuum evaporation LiF is steamed as electron injecting layer on the electron transport layer Plating is with a thickness of 0.5nm.Vacuum evaporation Al is as cathode, evaporation thickness 100nm on electron injecting layer.
The characteristics of luminescence of organic electroluminescence device prepared by Application Example 11-15 of the present invention and comparative example 3 Test result is as shown in table 3.
Table 3
Application Example 16: the preparation of organic electroluminescence device 16
Selection ito glass is anode, dries after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, above-mentioned Vacuum evaporation 2T-NATA is as hole injection layer, evaporation thickness 10nm in anode grid substrate.The vacuum evaporation on hole injection layer NPB is as hole transmission layer, evaporation thickness 30nm.The visitor of vacuum evaporation material of main part ADN on the hole transport layer, 2wt% Body material DPAVBi, as luminescent layer, evaporation thickness 45nm.Vacuum evaporation the compound of the present invention TM1 makees on the light-emitting layer For hole blocking layer, evaporation thickness 10nm.Vacuum evaporation Alq on the hole blocking layer3As electron transfer layer, evaporation thickness For 40nm.Vapor deposition LiF is as electron injecting layer, evaporation thickness 0.5nm on the electron transport layer.The vacuum on electron injecting layer Evaporating Al is as cathode, evaporation thickness 150nm.
Application Example 17: the preparation of organic electroluminescence device 17
Change the compound TM1 in Application Example 16 into compound TM5, other steps are identical.
Application Example 18: the preparation of organic electroluminescence device 18
Change the compound TM1 in Application Example 16 into compound TM12, other steps are identical.
Application Example 19: the preparation of organic electroluminescence device 19
Change the compound TM1 in Application Example 16 into compound TM14, other steps are identical.
Application Example 20: the preparation of organic electroluminescence device 20
Change the compound TM1 in Application Example 16 into compound TM19, other steps are identical.
Comparative example 4
Selection ito glass is anode, dries after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, above-mentioned Vacuum evaporation 2T-NATA is as hole injection layer, evaporation thickness 10nm in anode grid substrate.The vacuum evaporation on hole injection layer NPB is as hole transmission layer, evaporation thickness 30nm.The visitor of vacuum evaporation material of main part ADN on the hole transport layer, 2wt% Body material DPAVBi, as luminescent layer, evaporation thickness 45nm.Vacuum evaporation BAlq is as hole blocking layer on the light-emitting layer, Evaporation thickness is 10nm.Vacuum evaporation Alq on the hole blocking layer3As electron transfer layer, evaporation thickness 40nm.In electronics Vacuum evaporation LiF is as electron injecting layer, evaporation thickness 0.5nm in transport layer.Vacuum evaporation Al makees on electron injecting layer For cathode, evaporation thickness 150nm.
The characteristics of luminescence of organic electroluminescence device prepared by Application Example 16-20 of the present invention and comparative example 4 Test result is as shown in table 4.
Table 4
Application Example 21: the preparation of organic electroluminescence device 21
Selection ito glass is anode, dries after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, above-mentioned Vacuum evaporation 2T-NATA is as hole injection layer, evaporation thickness 10nm in anode grid substrate.The vacuum evaporation on hole injection layer NPB is as hole transmission layer, evaporation thickness 30nm.The visitor of vacuum evaporation material of main part CBP on the hole transport layer, 10wt% Body material Ir (ppy)3, as luminescent layer, evaporation thickness 30nm.Vacuum evaporation the compound of the present invention TM27 on the light-emitting layer As hole blocking layer, evaporation thickness 10nm.Vacuum evaporation Alq on the hole blocking layer3As electron transfer layer, vapor deposition is thick Degree is 35nm.Vacuum evaporation LiF is as electron injecting layer, evaporation thickness 0.2nm on the electron transport layer.In electron injecting layer Upper vacuum evaporation Al is as cathode, evaporation thickness 100nm.
Application Example 22: the preparation of organic electroluminescence device 22
Change the compound TM27 in Application Example 21 into compound TM29, other steps are identical.
Application Example 23: the preparation of organic electroluminescence device 23
Change the compound TM27 in Application Example 21 into compound TM32, other steps are identical.
Application Example 24: the preparation of organic electroluminescence device 24
Change the compound TM27 in Application Example 21 into compound TM44, other steps are identical.
Application Example 25: the preparation of organic electroluminescence device 25
Change the compound TM27 in Application Example 21 into compound TM53, other steps are identical.
Comparative example 5:
Selection ito glass is anode, dries after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, above-mentioned Vacuum evaporation 2T-NATA is as hole injection layer, evaporation thickness 10nm in anode grid substrate.The vacuum evaporation on hole injection layer NPB is as hole transmission layer, evaporation thickness 30nm.The visitor of vacuum evaporation material of main part CBP on the hole transport layer, 10wt% Body material Ir (ppy)3, as luminescent layer, evaporation thickness 30nm.This BAlq of vacuum evaporation is used as hole barrier on the light-emitting layer Layer, evaporation thickness 10nm.Vacuum evaporation Alq on the hole blocking layer3As electron transfer layer, evaporation thickness 35nm.? Vacuum evaporation LiF is as electron injecting layer, evaporation thickness 0.2nm on electron transfer layer.The vacuum evaporation on electron injecting layer Al is as cathode, evaporation thickness 100nm.
The characteristics of luminescence of organic electroluminescence device prepared by Application Example 21-25 of the present invention and comparative example 5 Test result is as shown in table 5.
Table 5
Application Example 26: the preparation of organic electroluminescence device 26
Selection ito glass is anode, dries after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, above-mentioned Vacuum evaporation NPB is as hole transmission layer, evaporation thickness 30nm in anode grid substrate.Vacuum evaporation main body on the hole transport layer The guest materials (piq) of material C BP, 10wt%2Ir (acac), as luminescent layer, evaporation thickness 30nm.It is true on the light-emitting layer Sky vapor deposition the compound of the present invention TM80 is as hole blocking layer, evaporation thickness 10nm.Vacuum evaporation on the hole blocking layer Alq3As electron transfer layer, evaporation thickness 20nm.Vacuum evaporation LiF is steamed as electron injecting layer on the electron transport layer Plating is with a thickness of 0.5nm.Vacuum evaporation Al is as cathode, evaporation thickness 100nm on electron injecting layer.
Application Example 27: the preparation of organic electroluminescence device 27
Change the compound TM80 in Application Example 26 into compound TM81, other steps are identical.
Application Example 28: the preparation of organic electroluminescence device 28
Change the compound TM80 in Application Example 26 into compound TM93, other steps are identical.
Application Example 29: the preparation of organic electroluminescence device 29
Change the compound TM80 in Application Example 26 into compound TM101, other steps are identical.
Application Example 30: the preparation of organic electroluminescence device 30
Change the compound TM80 in Application Example 26 into compound TM113, other steps are identical.
Comparative example 6:
Selection ito glass is anode, dries after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, above-mentioned Vacuum evaporation NPB is as hole transmission layer, evaporation thickness 30nm in anode grid substrate.Vacuum evaporation main body on the hole transport layer The guest materials (piq) of material C BP, 10wt%2Ir (acac), as luminescent layer, evaporation thickness 30nm.It is true on the light-emitting layer Sky vapor deposition BAlq is as hole blocking layer, evaporation thickness 10nm.Vacuum evaporation Alq on the hole blocking layer3It is passed as electronics Defeated layer, evaporation thickness 20nm.Vacuum evaporation LiF is as electron injecting layer, evaporation thickness 0.5nm on the electron transport layer. Vacuum evaporation Al is as cathode, evaporation thickness 100nm on electron injecting layer.
The characteristics of luminescence of organic electroluminescence device prepared by Application Example 26-30 of the present invention and comparative example 6 Test result is as shown in table 6.
Table 6
As can be seen that derivative of phenanthroline of the invention is hindered as electron transport material or hole from 1-table of table 6 Obstructing material is applied in organic electroluminescence device, which shows lower driving voltage, higher Luminous efficiency and longer service life, and there is preferable durability and reliability.

Claims (10)

1. a kind of derivative of phenanthroline, which is characterized in that the derivative of phenanthroline has the structure as shown in structural formula I General formula:
Wherein, the R1、R2、R3、R4The independent alkyl, substituted or unsubstituted selected from hydrogen, substituted or unsubstituted C1~C20 One of the aryl of C6~C30, heteroaryl of substituted or unsubstituted C3~C30；
The L1、L2The Asia of the independent arlydene selected from substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 One of heteroaryl.
2. a kind of derivative of phenanthroline according to claim 1, which is characterized in that the R1、R2、R3、R4Independent choosing From one of group as shown below,
Wherein, the X is selected from C (R)2、Si(R)2, O or S, the R be selected from the alkyl of substituted or unsubstituted C1~C10, take One of the aryl of generation or unsubstituted C6~C18, heteroaryl of substituted or unsubstituted C3~C18；
The X1、X2、X3、X4、X5、X6、X7、X8It is independent to be selected from C (R0) or N, the R0Selected from hydrogen, substituted or unsubstituted C1 The alkyl of~C10, the aryl of substituted or unsubstituted C6~C18, substituted or unsubstituted C3~C18 heteroaryl in one Kind；
The L is selected from the sub- heteroaryl of singly-bound, the arlydene of substituted or unsubstituted C6~C18, substituted or unsubstituted C3~C18 One of base.
3. a kind of derivative of phenanthroline according to claim 2, which is characterized in that the R is selected from methyl, ethyl, third Base, butyl, amyl, phenyl, pyridyl group, pyrimidine radicals, pyrazinyl, pyridazinyl, triazine radical, naphthalene, quinolyl, xenyl, furans One of base, thienyl；
The R0Selected from hydrogen, methyl, ethyl, propyl, butyl, amyl, phenyl, pyridyl group, pyrimidine radicals, pyrazinyl, pyridazinyl, three One of piperazine base, naphthalene, quinolyl, xenyl, terphenyl, triphenylene, furyl, thienyl.
4. a kind of derivative of phenanthroline according to claim 2, which is characterized in that the L be selected from singly-bound, phenylene, One of sub-pyridyl group, sub- pyrimidine radicals, sub- pyrazinyl, sub- pyridazinyl, naphthylene, sub- quinolyl, biphenylene.
5. a kind of derivative of phenanthroline according to claim 1, which is characterized in that the L1、L2It is independent selected from following One of shown group,
Wherein, the R5、R6、R7、R8、R9、R10、R11、R12、R13、R14It is independent to be selected from hydrogen, methyl, ethyl, propyl, butyl, penta Base, phenyl, pyridyl group, pyrimidine radicals, pyrazinyl, pyridazinyl, triazine radical, naphthalene, quinolyl, xenyl, fluorenyl, triphenylene, One of dibenzofuran group.
6. a kind of derivative of phenanthroline according to claim 1, which is characterized in that the R1、R2、R3、R4Independent choosing From one of group as shown below,
7. a kind of derivative of phenanthroline according to claim 1, which is characterized in that the L1、L2It is independent selected from following One of shown group,
8. a kind of derivative of phenanthroline according to claim 1, which is characterized in that the derivative of phenanthroline is selected from One of chemical structure as follows,
9. a kind of organic electroluminescence device, which is characterized in that the organic electroluminescence device includes anode, cathode and has Machine nitride layer, for the organic matter layer between the anode and the cathode, it is any that the organic matter layer contains claim 1-8 Derivative of phenanthroline described in one.
10. a kind of organic electroluminescence device according to claim 9, which is characterized in that the organic matter layer includes electricity Perhaps the hole blocking layer electron transfer layer or the hole blocking layer include claim 1-8 any one to sub- transport layer Derivative of phenanthroline described in.
CN201811054065.9A 2018-09-11 2018-09-11 A kind of derivative of phenanthroline and its organic electroluminescence device Withdrawn CN109096277A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110041159A (en) * 2019-04-24 2019-07-23 北京诚志永华显示科技有限公司 New compound, electroluminescent organic material, organic electroluminescent device, electronic device
CN114249685A (en) * 2021-12-31 2022-03-29 华南理工大学 Ortho-diaryl substituted phenanthrene or phenanthroline carrier transport material and preparation method and application thereof
CN114621257A (en) * 2022-03-31 2022-06-14 宇瑞(上海)化学有限公司 Phenanthroline compound, organic electroluminescent device and display or lighting device

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110041159A (en) * 2019-04-24 2019-07-23 北京诚志永华显示科技有限公司 New compound, electroluminescent organic material, organic electroluminescent device, electronic device
CN114249685A (en) * 2021-12-31 2022-03-29 华南理工大学 Ortho-diaryl substituted phenanthrene or phenanthroline carrier transport material and preparation method and application thereof
CN114621257A (en) * 2022-03-31 2022-06-14 宇瑞(上海)化学有限公司 Phenanthroline compound, organic electroluminescent device and display or lighting device

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