CN109400487A - A kind of fluorene kind derivative and its organic electroluminescence device - Google Patents
A kind of fluorene kind derivative and its organic electroluminescence device Download PDFInfo
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Abstract
The invention discloses a kind of fluorene kind derivative and its organic electroluminescence devices, are related to organic optoelectronic materials technology.Fluorene kind derivative of the invention is electron rich system, and has biggish conjugated structure, therefore hole mobility with higher, shows preferable hole transport performance.In addition fluorene kind derivative of the invention due to the fluorenyl and benzo fluorenyl of large volume introducing therefore there is biggish rigid structure, effectively raise the glass transition temperature and thermal stability of material, be conducive to material filming.Organic electroluminescence device of the invention includes anode, cathode with organic matter layer, and for organic matter layer between anode and cathode, organic matter layer contains fluorene kind derivative of the invention.Organic electroluminescence device of the invention has lower driving voltage, higher luminous efficiency, and has longer service life.
Description
Technical field
The present invention relates to organic photoelectrical material technical fields, and in particular to a kind of fluorene kind derivative and its organic electroluminescent
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
Several organic matter layers between metallic cathode, such as hole injection layer (HIL), hole transmission layer (HTL), luminescent layer (EML), electronics
Transport layer (ETL) and electron injecting layer (EIL) etc..Under certain voltage driving, hole and electronics are infused by anode and cathode respectively
Entering to hole transmission layer and electron transfer layer, the two passes through hole transmission layer respectively and electron transfer layer moves to luminescent layer, when
The two is met in luminescent layer forms hole-electron compound exciton when combining, exciton returns to ground state by way of luminescence relaxation,
It is luminous to achieve the purpose that.
As the hole transmission layer in OLED, basic role is the efficiency of transmission of raising hole in the devices, and will be electric
Son is effectively blocked in luminescent layer, realizes that the maximum of carrier is compound；Energy wall of the hole in injection process is reduced simultaneously
It builds, the injection efficiency in hole is improved, to improve the brightness of device, efficiency and service life.
Currently, usually there is the problems such as operation voltage is high, luminous efficiency is low, service life is short in organic electroluminescence device.
Thus, exploring the new organic photoelectrical material for organic electroluminescence device is that those skilled in the art study all the time
Emphasis direction.For hole transmission layer, traditionally material used, can not usually provide the satisfactory characteristics of luminescence,
Therefore, it is still necessary to design the better hole mobile material of new performance to improve the service performance of organic electroluminescence device.
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 fluorene kind derivatives and its organic electroluminescence to send out
Optical device, which applies in organic electroluminescence device as hole mobile material, to reduce Organic Electricity
The driving voltage of electroluminescence device, improves the luminous efficiency of organic electroluminescence device, and extends organic electroluminescent
The service life of device.
Above-mentioned technical purpose of the invention is achieved through the following technical solutions: a kind of fluorene kind derivative, the fluorenes class
Derivative has the general structure as shown in structural formula I:
Wherein, the L1Selected from one of singly-bound, the arlydene of substituted or unsubstituted C6~C18；
The n is selected from the integer between 2~4；
The R is selected from the alkyl of substituted or unsubstituted C1~C10, the alkenyl of substituted or unsubstituted C1~C10, substitution
Or one of the aryl of unsubstituted C6~C18, heteroaryl of substituted or unsubstituted C3~C18, connect between two neighboring R
It connects to form cyclic structure；
The R1、R2The independent alkyl selected from substituted or unsubstituted C1~C10, substituted or unsubstituted C6~C18
One of aryl, heteroaryl of substituted or unsubstituted C3~C18；
The Ar1The heteroaryl of aryl, substituted or unsubstituted C3~C60 selected from substituted or unsubstituted C6~C60
One of；
The Ar2Selected from one of group as follows,
The m is selected from 0 or 1；The X is selected from singly-bound or C (CH3)2, the L2Selected from singly-bound, substituted or unsubstituted phenylene,
It is substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorenylidene, substituted or unsubstituted
One of phenanthrylene, the L is selected from the arlydene of substituted or unsubstituted C6~C18, and the Ar, which is selected from, to be replaced 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 R3、R4It is independent to be selected from hydrogen, the alkyl of substituted or unsubstituted C1~C10, substituted or unsubstituted C6~C18
Aryl, one of the heteroaryl of substituted or unsubstituted C3~C18.
Preferably, fluorene kind derivative shown in the structural formula I is by structural formula I-1, structural formula I-2, structural formula I-3
Any one expression,
Preferably, the L1Selected from singly-bound, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, take
One of generation or unsubstituted naphthylene, substituted or unsubstituted fluorenylidene, substituted or unsubstituted phenanthrylene.
Preferably, the L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substitution or not
One of substituted naphthylene.
Preferably, the Ar2Selected from one of group as follows,
Preferably, the Ar1Selected from one of group as follows,
The R5、R6The independent alkyl selected from substituted or unsubstituted C1~C10, substituted or unsubstituted C6~C18
One of aryl, heteroaryl of substituted or unsubstituted C3~C18；
The L3Selected from one of singly-bound, the arlydene of substituted or unsubstituted C6~C18.
Preferably, the L3Selected from singly-bound, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, take
One of generation or unsubstituted naphthylene, substituted or unsubstituted fluorenylidene, substituted or unsubstituted phenanthrylene.
Preferably, the fluorene kind derivative 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 include anode,
Cathode and organic matter layer, the organic matter layer contain aforementioned present invention in the organic matter layer between anode and cathode
Fluorene kind derivative.
Preferably, the organic matter layer includes hole transmission layer, and the hole transmission layer includes the fluorenes class of aforementioned present invention
Derivative.
The utility model has the advantages that fluorene kind derivative of the invention is electron rich system, and there is biggish conjugated structure, therefore has
There is higher hole mobility, shows preferable hole transport performance.In addition fluorene kind derivative of the invention is due to large volume
Fluorenyl and benzo fluorenyl introducing therefore there is biggish rigid structure, effectively raise the glass transition temperature and heat of material
Stability is conducive to material filming.
Organic electroluminescence device using fluorene kind derivative of the invention as organic matter layer has lower driving electricity
Pressure, higher luminous efficiency, and there is 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 the application range claimed.
A kind of fluorene kind derivative, the fluorene kind derivative have the general structure as shown in structural formula I:
Wherein, the L1Selected from one of singly-bound, the arlydene of substituted or unsubstituted C6~C18；
The n is selected from the integer between 2~4；
The R is selected from the alkyl of substituted or unsubstituted C1~C10, the alkenyl of substituted or unsubstituted C1~C10, substitution
Or one of the aryl of unsubstituted C6~C18, heteroaryl of substituted or unsubstituted C3~C18, connect between two neighboring R
It connects to form cyclic structure；
The R1、R2The independent alkyl selected from substituted or unsubstituted C1~C10, substituted or unsubstituted C6~C18
One of aryl, heteroaryl of substituted or unsubstituted C3~C18；
The Ar1The heteroaryl of aryl, substituted or unsubstituted C3~C60 selected from substituted or unsubstituted C6~C60
One of；
The Ar2Selected from one of group as follows,The m
Selected from 0 or 1；The X is selected from singly-bound or C (CH3)2, the L2Selected from singly-bound, substituted or unsubstituted phenylene, substitution or
Unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorenylidene, substituted or unsubstituted sub- phenanthrene
One of base, the L are selected from the arlydene of substituted or unsubstituted C6~C18, and the Ar is selected from 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 R3、R4The independent virtue for being selected from hydrogen, the alkyl of substituted or unsubstituted C1~C10, substituted or unsubstituted C6~C18
One of base, heteroaryl of substituted or unsubstituted C3~C18.
Preferably, fluorene kind derivative shown in the structural formula I is by structural formula I-1, structural formula I-2, structural formula I-3
Any one expression,
Preferably, the L1Selected from singly-bound, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, take
One of generation or unsubstituted naphthylene, substituted or unsubstituted fluorenylidene, substituted or unsubstituted phenanthrylene.
Preferably, the L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substitution or not
One of substituted naphthylene.
Preferably, the Ar2Selected from one of group as follows,
Preferably, the Ar1Selected from one of group as follows,
The R5、R6The independent alkyl selected from substituted or unsubstituted C1~C10, substituted or unsubstituted C6~C18
One of aryl, heteroaryl of substituted or unsubstituted C3~C18；
The L3Selected from one of singly-bound, the arlydene of substituted or unsubstituted C6~C18.
Preferably, the L3Selected from singly-bound, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, take
One of generation or unsubstituted naphthylene, substituted or unsubstituted fluorenylidene, substituted or unsubstituted phenanthrylene.
According to the present invention, substituent group on abovementioned alkyl, alkenyl it is independent selected from hydrogen, deuterium, cyano, trifluoromethyl, C1~
The alkyl of C10, the alkoxy of C1~C10, the aryl of C6~C24 or the heteroaryl of C3~C24.
Substituent group on above-mentioned aryl, heteroaryl it is independent selected from hydrogen, deuterium, cyano, trifluoromethyl, C1~C10 alkyl,
The heteroaryl of the alkoxy of C1~C10, the aryl of C6~C24 or C3~C24.
Substituent group on above-mentioned arlydene, inferior heteroaryl it is independent selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, nitro,
The alkyl of C1~C10, the alkoxy of C1~C10, the aryl of C6~C24 or the heteroaryl of C3~C24.
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.
Alkenyl of the present invention refers to that alkyl made of minusing a hydrogen atom in olefin hydrocarbon molecules, the alkenyl can be single
Alkenyl, dialkylene 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.
Heteroarylidene 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~C10 of the present invention, substituted or unsubstituted C6~C18 aryl, take
The heteroaryl of generation or unsubstituted C3~C18 refer to be substituted before alkyl, aryl, heteroaryl the total number of carbon atoms be respectively 1~
10,6~18,3~18, and so on.As an example, it is not particularly limited, fluorene kind derivative of the invention is selected from as follows
One of chemical structure,
Some particular chemicals shown in structural formula I of the present invention, but structure of the invention Formulas I institute is enumerated above
The compound of expression is not limited to these listed chemical structures, all based on structure shown in structural formula I, and substituent group is such as
Group defined by upper should be all included.
The synthetic method of fluorene kind derivative shown in structural formula I of the invention is as follows:
It is obtained by carbon nitrogen coupling reactionAbove-mentioned intermediate product and
It is obtained by carbon nitrogen coupling reaction
Wherein, the X is selected from Cl, Br or I, described R, R1、R2、n、Ar1、Ar2、L1As defined above.
The synthetic route of fluorene kind derivative of the invention is not particularly limited, it can be ripe using those skilled in the art
The popular response known.
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device include anode, cathode with
And machine nitride layer, organic matter layer contain the fluorene kind derivative of aforementioned present invention between anode and cathode in organic matter layer.
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 of buffer layer or any multilayer.The thickness of organic matter layer of the invention is not higher than 6 μm, preferably not higher than 0.5 μ
M, and more preferably 0.02~0.5 μm.
In organic electroluminescence device of the invention, structural formula I compound represented can be used for above-mentioned organic matter layer
Any one layer or any multilayer, preferably contain in hole transmission layer.Content is not particularly limited, and can according to need suitable
Work as adjustment.
Organic electroluminescence device of the invention is preferred are as follows:
Substrate/anode/hole transmission layer/luminescent layer/electron transfer layer/metallic cathode；Alternatively,
Substrate/anode/hole injection layer/hole transmission layer/luminescent layer/electron transfer layer/electron injecting layer/metal yin
Pole；Alternatively,
Substrate/anode/hole injection layer/hole transmission layer/luminescent layer/hole blocking layer/electron transfer layer/electron injection
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 higher work-functions material, such as Ag, Au, Al, Cu, Ni, Mo, Ti,
The metals such as Zn, Pd, Pt or its alloy；The oxidation such as zinc oxide, indium oxide, indium tin oxide (ITO), indium-zinc oxide (IZO)
Object；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, derivative of tri-arylamine group, benzidine derivative, phthalocyanine derivates, naphthalocyanine derivative, porphyrin spread out
Biology, polyvinyl carbazole, polysilane, electroconductive polymer etc., but not limited to this.In addition, hole injection layer can be single layer
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
To be mixing material.
Hole mobile material of the invention, preferably with the material of preferable hole transport performance, for example, tri-arylamine group spreads out
Biology, diphenyl amine derivative, carbazole analog derivative, anthracene derivant, poly- (N- vinyl carbazole) (abbreviation PVK), poly- (4- ethylene
Base triphenylamine) (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
Above 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, Phen analog derivative etc., but not limited to this.
In addition, electron transfer layer can be single layer structure, it is also possible to two layers or more of multilayered structure, the electronics that each layer is included passes
Defeated 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.
Embodiment 1: the preparation of compound I-1
Under protection of argon gas, into flask be added compound D1 (42.8g, 150mmol), compound E1 (37.3g,
100mmol), sodium tert-butoxide (28.8g, 300mmol), tris(dibenzylideneacetone) dipalladium (1.4g, 1.5mmol), 1,1'- connection
The bis- diphenyl phosphines of naphthalene -2,2'- (1.9g, 3mmol) and toluene (350ml) react 24 hours under conditions of 130 DEG C.It, will after cooling
Mixture is filtered, and filtrate is concentrated under reduced pressure.Resulting crude product is subjected to column purification, is recrystallized with toluene,
It after being filtered, is dried, as a result obtains compound F1 (41.6g, 80%).
Under protection of argon gas, into flask be added compound F1 (5.20g, 10mmol), compound G1 (3.23g,
10mmol), sodium tert-butoxide (1.3g, 13.5mmol), tris(dibenzylideneacetone) dipalladium (0.046g, 0.05mmol), three tertiary fourths
Base phosphine (0.021g, 0.1mmol) and dehydrated toluene (50ml) react 2 hours at 80 DEG C.After cooling, it is added water (500ml),
Mixture is filtered, filtrate is extracted with toluene, organic phase is dry with anhydrous magnesium sulfate.It is concentrated under reduced pressure, it will
Resulting crude product carries out column purification, is recrystallized with toluene, after being filtered, is dried, as a result obtains product I-1
(5.41g, 71%).Mass spectrum m/z: theoretical value: 762.05；Measured value: 761.41.Theoretical elemental content (%) C58H51N:C,
91.42；H,6.75；N,1.84；Survey constituent content (%): C, 91.39；H,6.80；N,1.82.The above results confirmation is produced
Object is target product.
Embodiment 2: the preparation of compound I-33
Change the compound D1 in embodiment 1 into equimolar compound D2, compound G1 changes equimolar compound into
G2, other steps are identical as the synthesis of embodiment 1, obtain compound I-33 (5.52g, 75%).Mass spectrum m/z: theoretical value:
736.02；Measured value: 735.37.Theoretical elemental content (%) C56H49N:C, 91.39；H,6.71；N,1.90；Actual measurement element contains
Measure (%): C, 91.36；H,6.73；N,1.91.The above results confirm that obtaining product is target product.
Embodiment 3: the preparation of compound I-58
Change the compound D1 in embodiment 1 into equimolar compound D3, compound E1 changes equimolar E2, chemical combination into
Object G1 changes equimolar compound G3 into, other steps are identical as the synthesis of embodiment 1, obtain compound I-58 (5.33g,
70%).Mass spectrum m/z: theoretical value: 762.05；Measured value: 761.40.Theoretical elemental content (%) C58H51N:C, 91.42；H,
6.75；N,1.84；Survey constituent content (%): C, 91.41；H,6.78；N,1.83.The above results confirm that obtaining product is target
Product.
Embodiment 4: the preparation of compound I-68
Change the compound D1 in embodiment 1 into equimolar compound D3, compound E1 changes equimolar E3, chemical combination into
Object G1 changes equimolar compound G4 into, other steps are identical as the synthesis of embodiment 1, obtain compound I-68 (5.51g,
68%).Mass spectrum m/z: theoretical value: 810.10；Measured value: 809.40.Theoretical elemental content (%) C62H51N:C, 91.93；H,
6.35；N,1.73；Survey constituent content (%): C, 91.91；H,6.38；N,1.72.The above results confirm that obtaining product is target
Product.
Embodiment 5: the preparation of compound I-73
Changing the compound D1 in embodiment 1 into equimolar compound D3, compound E1 changes equimolar E4 into, other
Step is identical as the synthesis of embodiment 1, obtains compound I-73 (6.16g, 76%).Mass spectrum m/z: theoretical value: 810.10；It is real
Measured value: 809.36.Theoretical elemental content (%) C62H51N:C, 91.93；H,6.35；N,1.73；Constituent content (%): C is surveyed,
91.90；H,6.39；N,1.72.The above results confirm that obtaining product is target product.
Embodiment 6: the preparation of compound I-84
Changing the compound D1 in embodiment 1 into equimolar compound D4, compound E1 changes equimolar E4 into, other
Step is identical as the synthesis of embodiment 1, obtains compound I-84 (6.82g, 73%).Mass spectrum m/z: theoretical value: 934.24；It is real
Measured value: 933.41.Theoretical elemental content (%) C72H55N:C, 92.57；H,5.93；N,1.50；Constituent content (%): C is surveyed,
92.54；H,5.98；N,1.48.The above results confirm that obtaining product is target product.
Embodiment 7: the preparation of compound I-106
Change the compound D1 in embodiment 1 into equimolar compound D5, compound E1 changes equimolar E4, chemical combination into
Object G1 changes equimolar compound G2 into, other steps are identical as the synthesis of embodiment 1, obtain compound I-106 (6.62g,
77%).Mass spectrum m/z: theoretical value: 860.16；Measured value: 859.42.Theoretical elemental content (%) C66H53N:C, 92.16；H,
6.21；N,1.63；Survey constituent content (%): C, 92.13；H,6.26；N,1.61.The above results confirm that obtaining product is target
Product.
Embodiment 8: the preparation of compound I-145
Changing the compound D1 in embodiment 1 into equimolar compound D3, compound E1 changes equimolar E5 into, other
Step is identical as the synthesis of embodiment 1, obtains compound I-145 (5.20g, 80%).Mass spectrum m/z: theoretical value: 649.92；
Measured value: 649.36.Theoretical elemental content (%) C49H47N:C, 90.56；H,7.29；N,2.16；It surveys constituent content (%):
C,90.52；H,7.34；N,2.15.The above results confirm that obtaining product is target product.
Embodiment 9: the preparation of compound I-149
Changing the compound D1 in embodiment 1 into equimolar compound D6, compound E1 changes equimolar E5 into, other
Step is identical as the synthesis of embodiment 1, obtains compound I-149 (5.25g, 75%).Mass spectrum m/z: theoretical value: 699.98；
Measured value: 699.39.Theoretical elemental content (%) C53H49N:C, 90.94；H,7.06；N,2.00；It surveys constituent content (%):
C,90.92；H,7.09；N,1.99.The above results confirm that obtaining product is target product.
Embodiment 10: the preparation of compound I-161
Changing the compound D1 in embodiment 1 into equimolar compound D3, compound E1 changes equimolar E6 into, other
Step is identical as the synthesis of embodiment 1, obtains compound I-161 (5.13g, 72%).Mass spectrum m/z: theoretical value: 711.99；
Measured value: 711.37.Theoretical elemental content (%) C54H49N:C, 91.10；H,6.94；N,1.97；It surveys constituent content (%):
C,91.08；H,6.97；N,1.96.The above results confirm that obtaining product is target product.
Embodiment 11: the preparation of compound I-166
Changing the compound D1 in embodiment 1 into equimolar compound D2, compound E1 changes equimolar E7 into, other
Step is identical as the synthesis of embodiment 1, obtains compound I-166 (6.36g, 82%).Mass spectrum m/z: theoretical value: 776.08；
Measured value: 775.43.Theoretical elemental content (%) C59H53N:C, 91.31；H,6.88；N,1.80；It surveys constituent content (%):
C,91.29；H,6.91；N,1.79.The above results confirm that obtaining product is target product.
Embodiment 12: the preparation of compound I-177
Change the compound D1 in embodiment 1 into equimolar compound D3, compound E1 changes equimolar E7, chemical combination into
Object G1 changes equimolar compound G2 into, other steps are identical as the synthesis of embodiment 1, obtain compound I-177 (6.17g,
85%).Mass spectrum m/z: theoretical value: 726.02；Measured value: 725.41.Theoretical elemental content (%) C55H51N:C, 90.99；H,
7.08；N,1.93；Survey constituent content (%): C, 90.96；H,7.13；N,1.91.The above results confirm that obtaining product is target
Product.
Embodiment 13: the preparation of compound I-193
Change the compound D1 in embodiment 1 into equimolar compound D3, compound E1 changes equimolar E8, chemical combination into
Object G1 changes equimolar compound G2 into, other steps are identical as the synthesis of embodiment 1, obtain compound I-193 (5.90g,
76%).Mass spectrum m/z: theoretical value: 776.08；Measured value: 775.43.Theoretical elemental content (%) C59H53N:C, 91.31；H,
6.88；N,1.80；Survey constituent content (%): C, 91.28；H,6.92；N,1.79.The above results confirm that obtaining product is target
Product.
Embodiment 14: the preparation of compound I-199
Change the compound D1 in embodiment 1 into equimolar compound D3, compound E1 changes equimolar E9, chemical combination into
Object G1 changes equimolar compound G4 into, other steps are identical as the synthesis of embodiment 1, obtain compound I-199 (5.34g,
75%).Mass spectrum m/z: theoretical value: 711.99；Measured value: 711.37.Theoretical elemental content (%) C54H49N:C, 91.10；H,
6.94；N,1.97；Survey constituent content (%): C, 91.09；H,6.96；N,1.96.The above results confirm that obtaining product is target
Product.
Embodiment 15: the preparation of compound I-218
Changing the compound D1 in embodiment 1 into equimolar compound D7, compound E1 changes equimolar E7 into, other
Step is identical as the synthesis of embodiment 1, obtains compound I-218 (6.34g, 79%).Mass spectrum m/z: theoretical value: 802.12；
Measured value: 801.45.Theoretical elemental content (%) C61H55N:C, 91.34；H,6.91；N,1.75；It surveys constituent content (%):
C,91.31；H,6.95；N,1.74.The above results confirm that obtaining product is target product.
Embodiment 16: the preparation of compound I-223
Change the compound D1 in embodiment 1 into equimolar compound D3, compound E1 changes equimolar E10 into, changes
It closes object G1 and changes equimolar compound G5 into, other steps are identical as the synthesis of embodiment 1, obtain compound I-223
(6.12g, 86%).Mass spectrum m/z: theoretical value: 711.99；Measured value: 711.40.Theoretical elemental content (%) C54H49N:C,
91.10；H,6.94；N,1.97；Survey constituent content (%): C, 91.07；H,6.99；N,1.95.The above results confirmation is produced
Object is target product.
Other target products are synthesized referring to the synthetic method of above-described embodiment 1-16.
Application Example 1: the preparation of luminescent 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 60nm on anode.This hair of vacuum evaporation on hole injection layer
Bright compound I-1 is as hole transmission layer, evaporation thickness 30nm.Vacuum evaporation weight ratio is 40:2 on the hole transport layer
Material of main part CBP and dopant material Ir (ppy)3As luminescent layer, evaporation thickness 45nm.Vacuum evaporation on the light-emitting layer
Alq3As electron transfer layer, evaporation thickness 40nm.For vapor deposition 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 2: the preparation of luminescent device 2
Change the compound I-1 in Application Example 1 into compound I-33, other steps are identical.
Application Example 3: the preparation of luminescent device 3
Change the compound I-1 in Application Example 1 into compound I-58, other steps are identical.
Application Example 4: the preparation of luminescent device 4
Change the compound I-1 in Application Example 1 into compound I-68, other steps are identical.
Application Example 5: the preparation of luminescent device 5
Change the compound I-1 in Application Example 1 into compound I-73, other steps are identical.
Application Example 6: the preparation of luminescent device 6
Change the compound I-1 in Application Example 1 into compound I-84, other steps are identical.
Application Example 7: the preparation of luminescent device 7
Change the compound I-1 in Application Example 1 into compound I-106, other steps are identical.
Application Example 8: the preparation of luminescent device 8
Change the compound I-1 in Application Example 1 into compound I-145, 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 60nm on anode.The vacuum evaporation NPB on hole injection layer
As hole transmission layer, evaporation thickness 30nm.Vacuum evaporation weight ratio is the material of main part CBP of 40:2 on the hole transport layer
With dopant material body Ir (ppy)3As luminescent layer, evaporation thickness 45nm.Vacuum evaporation Alq on the light-emitting layer3It is passed as electronics
Defeated layer, evaporation thickness 40nm.Vapor deposition LiF is as electron injecting layer, evaporation thickness 0.2nm on the electron transport layer.In electricity
Vacuum evaporation Al is as cathode, evaporation thickness 100nm on sub- implanted layer.
The characteristics of luminescence of organic electroluminescence device prepared by Application Example 1-8 of the present invention and comparative example 1 is surveyed
Test result is as shown in table 1.
Table 1
Application Example 9: the preparation of luminescent device 9
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 60nm on anode.This hair of vacuum evaporation on hole injection layer
Bright compound I-149 is as hole transmission layer, evaporation thickness 30nm.Vacuum evaporation weight ratio is on the hole transport layer
The material of main part CBP and dopant material (piq) of 40:22Ir (acac) is used as luminescent layer, evaporation thickness 45nm.On the light-emitting layer
Vacuum evaporation Alq3As electron transfer layer, evaporation thickness 40nm.Vapor deposition LiF is as electron injection on the electron transport layer
Layer, evaporation thickness 0.2nm.Vacuum evaporation Al is as cathode, evaporation thickness 100nm on electron injecting layer.
Application Example 10: the preparation of luminescent device 10
Change the compound I-149 in Application Example 9 into compound I-161, other steps are identical.
Application Example 11: the preparation of luminescent device 11
Change the compound I-149 in Application Example 9 into compound I-166, other steps are identical.
Application Example 12: the preparation of luminescent device 12
Change the compound I-149 in Application Example 9 into compound I-177, other steps are identical.
Application Example 13: the preparation of luminescent device 13
Change the compound I-149 in Application Example 9 into compound I-193, other steps are identical.
Application Example 14: the preparation of luminescent device 14
Change the compound I-149 in Application Example 9 into compound I-199, other steps are identical.
Application Example 15: the preparation of luminescent device 15
Change the compound I-149 in Application Example 9 into compound I-218, other steps are identical.
Application Example 16: the preparation of luminescent device 16
Change the compound I-149 in Application Example 9 into compound I-223, other steps are identical.
Compare Application 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 60nm on anode.The vacuum evaporation NPB on hole injection layer
As hole transmission layer, evaporation thickness 30nm.Vacuum evaporation weight ratio is the material of main part CBP of 40:2 on the hole transport layer
With dopant material (piq)2Ir (acac) is used as luminescent layer, evaporation thickness 45nm.Vacuum evaporation Alq on the light-emitting layer3As electricity
Sub- transport layer, evaporation thickness 40nm.Vapor deposition LiF is as electron injecting layer, evaporation thickness 0.2nm 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 9-16 of the present invention and comparative example 2
Test result is as shown in table 2.
Table 2
As can be seen that fluorene kind derivative of the invention is applied to organic electroluminescence as hole mobile material from table 1, table 2
In luminescent device, which shows lower driving voltage, higher luminous efficiency and longer use
Service life, and there is preferable durability and reliability.
Claims (10)
1. a kind of fluorene kind derivative, which is characterized in that the fluorene kind derivative has the general structure as shown in structural formula I:
Wherein, the L1Selected from one of singly-bound, the arlydene of substituted or unsubstituted C6~C18；
The n is selected from the integer between 2~4；
The R be selected from the alkyl of substituted or unsubstituted C1~C10, substituted or unsubstituted C1~C10 alkenyl, replace or not
One of the aryl of substituted C6~C18, heteroaryl of substituted or unsubstituted C3~C18, connect shape between two neighboring R
Circlewise structure；
The R1、R2The virtue of the independent alkyl selected from substituted or unsubstituted C1~C10, substituted or unsubstituted C6~C18
One of base, heteroaryl of substituted or unsubstituted C3~C18；
The Ar1Aryl selected from substituted or unsubstituted C6~C60, one in the heteroaryl of substituted or unsubstituted C3~C60
Kind；
The Ar2Selected from one of group as follows,
The m is selected from 0 or 1；The X is selected from singly-bound or C (CH3)2, the L2Selected from singly-bound, substituted or unsubstituted phenylene,
It is substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorenylidene, substituted or unsubstituted
One of phenanthrylene, the L is selected from the arlydene of substituted or unsubstituted C6~C18, and the Ar, which is selected from, to be replaced or do not take
The alkyl of the C1~C10 in generation, the aryl of substituted or unsubstituted C6~C18, in substituted or unsubstituted C3~C18 heteroaryl
One kind, the R3、R4It is independent selected from hydrogen, the alkyl of substituted or unsubstituted C1~C10, substituted or unsubstituted C6~C18
One of aryl, substituted or unsubstituted C3~C18 heteroaryl.
2. a kind of fluorene kind derivative according to claim 1, which is characterized in that fluorenes class shown in the structural formula I is derivative
Object by any of structural formula I-1, structural formula I-2, structural formula I-3 indicate,
3. a kind of fluorene kind derivative according to claim 1, which is characterized in that the L1Selected from singly-bound, substituted or unsubstituted
Phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorenylidene, take
One of generation or unsubstituted phenanthrylene.
4. a kind of fluorene kind derivative according to claim 1, which is characterized in that the L is selected from substituted or unsubstituted Asia
One of phenyl, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene.
5. a kind of fluorene kind derivative according to claim 1, which is characterized in that the Ar2In group as follows
One kind,
6. a kind of fluorene kind derivative according to claim 1, which is characterized in that the Ar1In group as follows
One kind,
The R5、R6The virtue of the independent alkyl selected from substituted or unsubstituted C1~C10, substituted or unsubstituted C6~C18
One of base, heteroaryl of substituted or unsubstituted C3~C18；
The L3Selected from one of singly-bound, the arlydene of substituted or unsubstituted C6~C18.
7. a kind of fluorene kind derivative according to claim 6, which is characterized in that the L3Selected from singly-bound, substituted or unsubstituted
Phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorenylidene, take
One of generation or unsubstituted phenanthrylene.
8. a kind of fluorene kind derivative according to claim 1, which is characterized in that the fluorene kind derivative is selected from as follows
One of chemical structure,
9. a kind of organic electroluminescence device, which is characterized in that the organic electroluminescence device includes anode, cathode and has
Machine nitride layer, the organic matter layer is between anode and cathode, containing described in any one of claim 1-8 in the organic matter layer
Fluorene kind derivative.
10. a kind of organic electroluminescence device according to claim 9, which is characterized in that the organic matter layer includes sky
Cave transport layer, the hole transmission layer include the described in any item fluorene kind derivatives of claim 1-8.
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| CN113773207B (en) * | 2021-06-18 | 2022-08-02 | 北京莱特众成光电材料科技有限公司 | Organic compound, and electronic element and electronic device comprising same |
| CN115093335A (en) * | 2022-08-29 | 2022-09-23 | 吉林奥来德光电材料股份有限公司 | Luminous auxiliary material and preparation method and application thereof |
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