CN106905221A - A kind of benzo fluorene kind derivative and its organic luminescent device - Google Patents
A kind of benzo fluorene kind derivative and its organic luminescent device Download PDFInfo
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- CN106905221A CN106905221A CN201710125368.4A CN201710125368A CN106905221A CN 106905221 A CN106905221 A CN 106905221A CN 201710125368 A CN201710125368 A CN 201710125368A CN 106905221 A CN106905221 A CN 106905221A
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- 0 C*1CCCC1 Chemical compound C*1CCCC1 0.000 description 3
- HRBCNLGJKRQXOG-UHFFFAOYSA-N CC(C)(c1c2)c3c(cccc4)c4c(c(-c(c(C4(C)C)c5)ccc5-c5cc(-[n]6c7ccccc7c7c6cccc7)ccc5)c4c4ccccc44)c4c3-c1ccc2-c1ccccc1 Chemical compound CC(C)(c1c2)c3c(cccc4)c4c(c(-c(c(C4(C)C)c5)ccc5-c5cc(-[n]6c7ccccc7c7c6cccc7)ccc5)c4c4ccccc44)c4c3-c1ccc2-c1ccccc1 HRBCNLGJKRQXOG-UHFFFAOYSA-N 0.000 description 1
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Abstract
The present invention provides a kind of benzo fluorene kind derivative and its organic luminescent device, belongs to organic photoelectrical material technical field.The benzo fluorene kind derivative derivative has structure shown in formula (I).Organic luminescent device prepared by a kind of benzo fluorene kind derivative provided using the present invention, with luminous efficiency higher, external quantum efficiency, relatively low driving voltage.
Description
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to a kind of benzo fluorene kind derivative and use the derivative
The organic luminescent device of thing.
Background technology
Organic electroluminescent refer to organic material under electric field action, excited by electric current and electric field and luminous showed
As.Organic electroluminescent LED (OLED) is the Display Technique of new generation that display is realized using this phenomenon.Such as have complete solid
State, from main light emission, brightness high, high-resolution, visual angle wide, fast response time, thickness of thin, small volume, it is lightweight, can be used flexibility
Substrate, low-voltage direct-current drive, low in energy consumption, operating temperature range is wide etc. so that its application market is quite varied.
In the research of OLED, the selection of organic material plays conclusive effect.Sandwich type OLED is according to work(
Can classify can be divided into hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer etc., and luminescent layer
Main material is called material of main part.Compound of fluorene class is the important material of main part of a class, due to the rigid structure that it has, therefore
The glass transition temperature and heat endurance of material are higher.But, presently disclosed these compound of fluorene class are used as main body material
The driving voltage of material, luminous efficiency are all poor.
The content of the invention
In view of this, it is an object of the invention to provide a kind of benzo fluorene kind derivative and the organic hair using the derivative
Optical device, derivative of the present invention can be applied to organic luminescent device as material of main part.Spread out using benzfluorene class of the present invention
Organic luminescent device prepared by biology, with luminous efficiency higher, lower driving voltage, and external quantum efficiency higher.
Present invention firstly provides a kind of benzo fluorene kind derivative, with the structural formula as described in formula (I)：
Wherein, A1-A8It is independent selected from hydrogen, substituted or unsubstituted alkyl or substituted or unsubstituted aromatic hydrocarbyl；
R1、R2It is independent selected from hydrogen, deuterium, fluorine, substituted or unsubstituted aromatic hydrocarbyl, substituted or unsubstituted arylamine, substitution or not take
Any one in the aromatic heterocycle in generation.
Preferably, A1-A8It is independent selected from hydrogen, substituted or unsubstituted C1-C50 alkyl or substituted or unsubstituted C6-
C50 aromatic hydrocarbyls；R1、R2It is independent selected from hydrogen, deuterium, fluorine, substituted or unsubstituted C6-C50 aromatic hydrocarbyls, substitution or not
Any one in substituted C6-C50 arylamine, substituted or unsubstituted C12-C50 carbazole derivates.
Preferably, A1-A8It is independent selected from hydrogen, substituted or unsubstituted C1-C30 alkyl or substituted or unsubstituted C6-
C30 aromatic hydrocarbyls；R1、R2It is independent selected from hydrogen, it is substituted or unsubstituted C6-C30 aromatic hydrocarbyls, substituted or unsubstituted
Any one in the arylamine of C6-C30, the carbazole derivates of substituted or unsubstituted C12-C30.
Preferably, the aromatic hydrocarbyl is selected from phenyl, xenyl, terphenyl, deuterated phenyl, naphthyl, anthryl, phenanthrene
Base, fluorenyl, the fluorenyl of spiral shell two, 9,9- diphenyl -9H- fluorenyls or pyrenyl.
Preferably, the arylamine is selected from any one in following structure：
Preferably, the carbazole derivates are selected from any one in following structure：
Preferably, the benzo fluorene kind derivative, as shown in any one of formula 1~20：
The present invention also provides a kind of organic luminescent device, including first electrode, second electrode and is placed between two electrodes
One or more organic layers, at least one organic layer includes benzo fluorene kind derivative of the present invention.
Beneficial effects of the present invention：
The present invention provides a kind of benzo fluorene kind derivative and the organic luminescent device using the derivative, the benzfluorene class
Derivative has structure shown in formula (I).Benzo fluorene kind derivative of the present invention can be applied to organic light emission as material of main part
Device.
Test result indicate that, organic luminescent device prepared by the benzo fluorene kind derivative provided using the present invention, light effect
Rate reaches as high as 8.7cd/A, and driving voltage is minimum can reach 3.2V, and maximum external quantum efficiency is 19.7%, is a kind of excellent
Different OLED material.
Specific embodiment
Technical scheme below in conjunction with the embodiment of the present invention is clearly and completely described, it is clear that described implementation
Example is only a part of embodiment of the invention, rather than whole embodiments.Based on the embodiment in the present invention, this area is common
The every other embodiment that technical staff is obtained under the premise of creative work is not made, belongs to the model of present invention protection
Enclose.
It should be noted that unless otherwise prescribed, the implication of scientific and technical terminology used in the present invention and people in the art
The implication that member is generally understood is identical.
Present invention firstly provides a kind of benzo fluorene kind derivative, shown in its general structure such as formula (I)：
Wherein, A1-A8It is independent selected from hydrogen, substituted or unsubstituted alkyl or substituted or unsubstituted aromatic hydrocarbyl；
R1、R2It is independent selected from hydrogen, deuterium, fluorine, substituted or unsubstituted aromatic hydrocarbyl, substituted or unsubstituted arylamine, substitution or not take
Any one in the aromatic heterocycle in generation.It is preferred that A1-A8It is independent selected from hydrogen, substituted or unsubstituted C1-C50 alkyl or substitution
Or unsubstituted C6-C50 aromatic hydrocarbyls；R1、R2It is independent selected from hydrogen, deuterium, fluorine, substituted or unsubstituted C6-C50 aromatic series
Any one in alkyl, substituted or unsubstituted C6-C50 arylamine, substituted or unsubstituted C12-C50 carbazole derivates.Again
It is preferred that A1-A8It is independent selected from hydrogen, substituted or unsubstituted C1-C30 alkyl or substituted or unsubstituted C6-C30 aromatic hydrocarbons
Base；R1、R2It is independent selected from hydrogen, substituted or unsubstituted C6-C30 aromatic hydrocarbyls, substituted or unsubstituted C6-C30 virtue
Any one in amine, the carbazole derivates of substituted or unsubstituted C12-C30.
According to the present invention, the alkyl refers to minus an alkyl for hydrogen atom in alkane molecule, and it can be straight
Alkyl group or straight chained alkyl, for example may be selected from methyl, ethyl, propyl group, isopropyl, normal-butyl, isobutyl group, sec-butyl, the tert-butyl group,
Amyl group, isopentyl or hexyl etc., but not limited to this.
The aromatic hydrocarbyl refers to after removing a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule, to be left the total of univalent perssad
Claim, it can be monocyclic aryl or fused ring aryl, for example, may be selected from phenyl, xenyl, naphthyl, anthryl, phenanthryl or pyrenyl etc., but
Not limited to this.
The arylamine refers to the amine for replacing base with armaticity, i.e.-NH2,-NH- or nitrogen-containing group be connected on aromatic hydrocarbon.
The aromatic heterocycle refers to that one or more the aromatic core carbon in aromatic hydrocarbyl are substituted the group for obtaining by hetero atom
General name, the hetero atom includes but is not limited to oxygen, sulphur and nitrogen-atoms, and the aromatic heterocycle can be monocyclic or condensed ring, for example
Pyridine radicals, pyrimidine radicals, benzo pyrimidine radicals, carbazyl, triazine radical, benzothiazolyl or benzimidazolyl etc. are may be selected from, but is not limited
In this.
According to the present invention, the substituted alkyl, the aromatic hydrocarbyl of substitution, the arylamine of substitution, the aromatic heterocycle of substitution
In, the substitution base preferably is selected from the one kind or several in the aromatic hydrocarbyl of halogen, deuterium, cyano group, the alkyl of C1-C10 or C6-C20
Kind, the number of the substitution base is preferably 0~3.
According to the present invention, the carbazole derivates refer to hydrogen atom or atomic group in carbazole by other atoms or atomic group
Replace and derivative more complicated product.
According to the present invention, more preferably described aromatic hydrocarbyl is selected from phenyl, xenyl, terphenyl, deuterated phenyl, naphthalene
Base, anthryl, phenanthryl, fluorenyl, the fluorenyl of spiral shell two, 9,9- diphenyl -9H- fluorenyls or pyrenyl.
More preferably described arylamine is selected from any one in following structure：
。
More preferably described carbazole derivates are selected from any one in following structure：
It should be noted that shown dotted line " ﹍ " represent and be joined directly together between two atoms in compound molecule or not phase
Even.
It is more highly preferred to, the benzo fluorene kind derivative, as shown in any one of formula 1~20：
It is enumerated above some specific structure types of benzo fluorene kind derivative of the present invention, but benzene of the present invention
And fluorene kind derivative is not limited to these listed chemical constitutions, every based on structure shown in formula (I), R1、R2、A1-A8
For group as defined above should all be included.
Benzo fluorene kind derivative described in formula (I) of the present invention can be prepared by following reaction scheme：
The present invention does not have particular/special requirement to the reaction condition of above-mentioned all kinds of reactions, with well known to those skilled in the art such
The normal condition of reaction.The present invention has no particular limits to the source of the raw material employed in above-mentioned all kinds of reactions, can
Think commercially available prod or prepared using preparation method well-known to those skilled in the art.Wherein, the R1、R2、A1-A8
Selection it is same as above, will not be repeated here.
The present invention also provides a kind of organic luminescent device.What the organic luminescent device was well known to those skilled in the art
Organic luminescent device, organic luminescent device of the present invention includes first electrode, second electrode and is placed between two electrodes
One or more organic layers, the organic layer preferably include hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer,
At least one of which in hole blocking layer, electron transfer layer and electron injecting layer, contains institute of the present invention in preferably described luminescent layer
The benzo fluorene kind derivative stated.
Embodiment 1：The preparation of compound 1
Step1, takes the compound II of 100mmol, adds enough solvent chloroforms, is adding NBS 300mmol, BPO (mistakes
BP) 2mmol, under nitrogen protection, backflow is warmed up to, react 5h.After reaction, three are washed with solution of sodium bisulfite
Secondary, organic phase is spin-dried for solvent, and crude product crosses silicagel column, obtains product 83mmol III.
Step2, under nitrogen protection, takes 83mmol III, is dissolved in dioxane solvent, and 200mmol is added afterwards
1- (1- pyrrolidines) cyclohexene, react 24h under reflux temperature.After the completion of reaction, enough water, mixture is added to be heated to reflux
2h.After being spin-dried for solvent, crude product ether dissolution, successively with 5% HCl, and 5% sodium bicarbonate aqueous solution washing, solvent rotation
Dry, the crude product for obtaining crosses silicagel column purification.Obtain intermediate 56mmol.56mmol intermediates are dissolved in chloroform, are added
10% methanesulfonic acid, mixed liquor reacts 2h at room temperature.After the completion of reaction, solution is washed with sodium bicarbonate solution, and solvent is evaporated
Afterwards, crude product silicagel column purification obtains intermediate II 20mmol, is dissolved in solvent triglyme, adds 10%
Palladium carbon, mixture back flow reaction 16h, crude product crosses silicagel column and obtains product I V 18mmol.
Step3,18mmol compounds IV is dissolved in anhydrous THF, cools to -78 degrees Celsius, adds n-BuLi molten
The equivalent of liquid 5, reacts 1h at this temperature.The equivalent of iodomethane 5 is added dropwise afterwards, room temperature is slowly warmed up to, reaction is overnight.Use saturation chlorine
Change ammonium salt solution and reaction is quenched, solvent is spin-dried for, and crude product crosses silicagel column and obtains product 5mmol V.
Step4, takes the ferric trichloride of the compound V of 5mmol, the enough solvent chloroforms of addition and catalytic amount, cools to 0 and takes the photograph
Family name's degree, is added dropwise the chloroformic solution of the bromine of 5 equivalents, reacts 24 hours at this temperature, is quenched instead with aqueous solution of sodium bisulfite
Should, organic solvent is evaporated, crude product crosses silicagel column and obtains VI, 3mmol.
Step5, takes the compound VI of 3mmol, adds the carbazole of 6mmol, 9mmol potassium tert-butoxides, 0.3mmol Pd2
(dba)3, toluene, argon gas displacement three times, addition 0.6mmol tri-butyl phosphines, argon gas displacement three times, anti-under reflux temperature again
10h is answered, crude product crosses silicagel column, obtain product 2.5mmol compounds 1.
Mass spectrum m/z：790.45 (calculated value 790.33) the above results confirm that it is target product to obtain product.
Embodiment 2：The synthesis of compound 2
Step1, takes the compound II of 100mmol, adds enough solvent chloroforms, is adding NBS 300mmol, BPO
2mmol, under nitrogen protection, is warmed up to backflow, reacts 5h.After reaction, washed with solution of sodium bisulfite three times, organic phase is spin-dried for
Solvent, crude product crosses silicagel column, obtains product 83mmol III.
Step2, under nitrogen protection, takes 83mmol III, is dissolved in dioxane solvent, and 200mmol is added afterwards
1- (1- pyrrolidines) cyclohexene, react 24h under reflux temperature.After the completion of reaction, enough water, mixture is added to be heated to reflux
2h.After being spin-dried for solvent, crude product ether dissolution, successively with 5% HCl, and 5% sodium bicarbonate aqueous solution washing, solvent rotation
Dry, the crude product for obtaining crosses silicagel column purification.Obtain intermediate 56mmol.56mmol intermediates are dissolved in chloroform, are added
10% methanesulfonic acid, mixed liquor reacts 2h at room temperature.After the completion of reaction, solution is washed with sodium bicarbonate solution, and solvent is evaporated
Afterwards, crude product silicagel column purification obtains intermediate II 20mmol, is dissolved in solvent triglyme, adds 10%
Palladium carbon, mixture back flow reaction 16h, crude product crosses silicagel column and obtains product I V 18mmol.
Step3,18mmol compounds IV is dissolved in anhydrous THF, cools to -78 degrees Celsius, adds n-BuLi molten
The equivalent of liquid 5, reacts 1h at this temperature.The equivalent of iodomethane 5 is added dropwise afterwards, room temperature is slowly warmed up to, reaction is overnight.Use saturation chlorine
Change ammonium salt solution and reaction is quenched, solvent is spin-dried for, and crude product crosses silicagel column and obtains product 5mmol V.
Step4, takes the ferric trichloride of the compound V of 5mmol, the enough solvent chloroforms of addition and catalytic amount, cools to 0 and takes the photograph
Family name's degree, is added dropwise the chloroformic solution of the bromine of 5 equivalents, reacts 24 hours at this temperature, is quenched instead with aqueous solution of sodium bisulfite
Should, organic solvent is evaporated, crude product crosses silicagel column and obtains VI, 3mmol.
Step5, takes the compound VI of 3mmol, adds the phenyl boric acid of 6mmol, 9mmol sodium carbonate, the triphenyls of 0.3mmol tetra-
Phosphorus palladium, toluene, argon gas is replaced three times, and 10h is reacted under reflux temperature, and crude product crosses silicagel column, obtains product 2.5mmol compounds
2。
Mass spectrum m/z：612.37 (calculated value 612.28) the above results confirm that it is target product to obtain product.
Embodiment 3：The synthesis of compound 3
Step1, takes the compound II of 100mmol, adds enough solvent chloroforms, is adding NBS 300mmol, BPO
2mmol, under nitrogen protection, is warmed up to backflow, reacts 5h.After reaction, washed with solution of sodium bisulfite three times, organic phase is spin-dried for
Solvent, crude product crosses silicagel column, obtains product 83mmol III.
Step2, under nitrogen protection, takes 83mmol III, is dissolved in dioxane solvent, and 200mmol is added afterwards
1- (1- pyrrolidines) cyclohexene, react 24h under reflux temperature.After the completion of reaction, enough water, mixture is added to be heated to reflux
2h.After being spin-dried for solvent, crude product ether dissolution, successively with 5% HCl, and 5% sodium bicarbonate aqueous solution washing, solvent rotation
Dry, the crude product for obtaining crosses silicagel column purification.Obtain intermediate 56mmol.56mmol intermediates are dissolved in chloroform, are added
10% methanesulfonic acid, mixed liquor reacts 2h at room temperature.After the completion of reaction, solution is washed with sodium bicarbonate solution, and solvent is evaporated
Afterwards, crude product silicagel column purification obtains intermediate II 20mmol, is dissolved in solvent triglyme, adds 10%
Palladium carbon, mixture back flow reaction 16h, crude product crosses silicagel column and obtains product I V 18mmol.
Step3,18mmol compounds IV is dissolved in anhydrous THF, cools to -78 degrees Celsius, adds n-BuLi molten
The equivalent of liquid 5, reacts 1h at this temperature.The equivalent of iodomethane 5 is added dropwise afterwards, room temperature is slowly warmed up to, reaction is overnight.Use saturation chlorine
Change ammonium salt solution and reaction is quenched, solvent is spin-dried for, and crude product crosses silicagel column and obtains product 5mmol V.
Step4, takes the ferric trichloride of the compound V of 5mmol, the enough solvent chloroforms of addition and catalytic amount, cools to 0 and takes the photograph
Family name's degree, is added dropwise the chloroformic solution of the bromine of 5 equivalents, reacts 24 hours at this temperature, is quenched instead with aqueous solution of sodium bisulfite
Should, organic solvent is evaporated, crude product crosses silicagel column and obtains VI, 3mmol.
Step5, takes the compound VI of 3mmol, adds the phenyl boric acid of 2.8mmol, 9mmol sodium carbonate, the triphens of 0.3mmol tetra-
Base phosphorus palladium, toluene, argon gas is replaced three times, and 10h is reacted under reflux temperature, and crude product crosses silicagel column, obtains product 2.5mmol chemical combination
Thing VII.
Step6, takes the compound VII of 2.5mmol, adds the naphthalene boronic acids of 2.6mmol, 7.5mmol sodium carbonate, 0.25mmol
Four triphenyl phosphorus palladiums, toluene, argon gas is replaced three times, and 10h is reacted under reflux temperature, and crude product crosses silicagel column, obtains product
2.0mmol compounds 3.
Mass spectrum m/z：662.37 (calculated value 662.3) the above results confirm that it is target product to obtain product.
Embodiment 4：The synthesis of compound 4
By the R in embodiment 31And R2Group replaces with R as implied above1And R2Group, other steps with the phase of embodiment 3
Together, compound 4 is obtained.Mass spectrum m/z：738.02 (calculated values：738.33).
Embodiment 5：The synthesis of compound 5
By the R in embodiment 31And R2Group replaces with R as implied above1And R2Group, other steps with the phase of embodiment 3
Together, compound 5 is obtained.Mass spectrum m/z：728.18 (calculated values：728.34).
Embodiment 6：The synthesis of compound 6
Step1, takes the compound II of 100mmol, adds enough solvent chloroforms, in addition NBS 300mmol,
BPO2mmol, under nitrogen protection, is warmed up to backflow, reacts 5h.After reaction, three times, organic phase are washed with solution of sodium bisulfite
Solvent is spin-dried for, crude product crosses silicagel column, obtains product 83mmol III.
Step2, under nitrogen protection, takes 83mmol III, is dissolved in dioxane solvent, and 200mmol is added afterwards
1- (1- pyrrolidines) cyclohexene, react 24h under reflux temperature.After the completion of reaction, enough water, mixture is added to be heated to reflux
2h.After being spin-dried for solvent, crude product ether dissolution, successively with 5% HCl, and 5% sodium bicarbonate aqueous solution washing, solvent rotation
Dry, the crude product for obtaining crosses silicagel column purification.Obtain intermediate 56mmol.56mmol intermediates are dissolved in chloroform, are added
10% methanesulfonic acid, mixed liquor reacts 2h at room temperature.After the completion of reaction, solution is washed with sodium bicarbonate solution, and solvent is evaporated
Afterwards, crude product silicagel column purification obtains intermediate II 20mmol, is dissolved in solvent triglyme, adds 10%
Palladium carbon, mixture back flow reaction 16h, crude product crosses silicagel column and obtains product I V 18mmol.
Step3,18mmol compounds IV is dissolved in anhydrous THF, cools to -78 degrees Celsius, adds n-BuLi molten
The equivalent of liquid 5, reacts 1h at this temperature.The equivalent of iodomethane 5 is added dropwise afterwards, room temperature is slowly warmed up to, reaction is overnight.Use saturation chlorine
Change ammonium salt solution and reaction is quenched, solvent is spin-dried for, and crude product crosses silicagel column and obtains product 5mmol V.
Step4, takes the ferric trichloride of the compound V of 5mmol, the enough solvent chloroforms of addition and catalytic amount, cools to 0 and takes the photograph
Family name's degree, is added dropwise the chloroformic solution of the bromine of 5 equivalents, reacts 24 hours at this temperature, is quenched instead with aqueous solution of sodium bisulfite
Should, organic solvent is evaporated, crude product crosses silicagel column and obtains VI, 3mmol.
Step5, takes the compound VI of 3mmol, adds the phenyl boric acid of 2.8mmol, 9mmol sodium carbonate, the triphens of 0.3mmol tetra-
Base phosphorus palladium, toluene, argon gas is replaced three times, and 10h is reacted under reflux temperature, and crude product crosses silicagel column, obtains product 2.5mmol chemical combination
Thing VII.
Step6, takes the compound VII of 2.5mmol, adds THF and methyl alcohol 5:1 mixed solvent, adds 10% Pd/C,
5h is reacted under hydrogen atmosphere.Obtain product 2mmol 6.
Mass spectrum m/z：774.66 (calculated values：774.33).
Embodiment 7：The synthesis of compound 7
By the R in embodiment 31And R2Group replaces with R as implied above1And R2Group, other steps with the phase of embodiment 3
Together, compound 7 is obtained.Mass spectrum m/z：779.15 (calculated values：779.36).
Embodiment 8：The synthesis of compound 8
By the R in embodiment 31And R2Group replaces with R as implied above1And R2Group, other steps with the phase of embodiment 3
Together, compound 8 is obtained.Mass spectrum m/z：777.76 (calculated values：777.34).
Embodiment 9：The synthesis of compound 9
By the R in embodiment 31And R2Group replaces with R as implied above1And R2Group, other steps with the phase of embodiment 3
Together, compound 9 is obtained.Mass spectrum m/z：777.56 (calculated values：777.34).
Embodiment 10：The synthesis of compound 10
By the R in embodiment 31And R2Group replaces with R as implied above1And R2Group, other steps with the phase of embodiment 3
Together, compound 10 is obtained.Mass spectrum m/z：829.57 (calculated values：829.37).
Embodiment 11：The synthesis of compound 11
By the R in embodiment 61And R2Group replaces with R as implied above1And R2Group, other steps with the phase of embodiment 6
Together, compound 11 is obtained.Mass spectrum m/z：541.63 (calculated values：541.28).
Embodiment 12：The synthesis of compound 12
By the R in embodiment 21And R2Group replaces with R as implied above1And R2Group, other steps with the phase of embodiment 2
Together, compound 12 is obtained.Mass spectrum m/z：622.43 (calculated values：622.34).
Embodiment 13：The synthesis of compound 13
By the R in embodiment 61And R2Group replaces with R as implied above1And R2Group, other steps with the phase of embodiment 6
Together, compound 13 is obtained.Mass spectrum m/z：688.37 (calculated values：688.31).
Embodiment 14：The synthesis of compound 14
By the R in embodiment 61And R2Group replaces with R as implied above1And R2Group, other steps with the phase of embodiment 6
Together, compound 14 is obtained.Mass spectrum m/z：776.56 (calculated values：776.34).
Embodiment 15：The synthesis of compound 15
By the R in embodiment 21And R2Group replaces with R as implied above1And R2Group, other steps with the phase of embodiment 2
Together, compound 15 is obtained.Mass spectrum m/z：712.35 (calculated values：712.31).
Embodiment 16：The synthesis of compound 16
By the R in embodiment 61And R22 groups replace with R as implied above1And R2Group, other steps with the phase of embodiment 6
Together, compound 16 is obtained.Mass spectrum m/z：660.82 (calculated values：660.28).
Embodiment 17：The synthesis of compound 17
By the R in embodiment 61And R2Group replaces with R as implied above1And R2Group, other steps with the phase of embodiment 6
Together, compound 17 is obtained.Mass spectrum m/z：870.51 (calculated values：870.4).
Embodiment 18：The synthesis of compound 18
By the R in embodiment 61And R2Group replaces with as above institute R1And R2Group, other steps are same as Example 6,
Obtain compound 18.Mass spectrum m/z：868.36 (calculated values：868.38.
Embodiment 19：The synthesis of compound 19
By the R in embodiment 21And R2Group replaces with R as implied above1And R2Group, other steps with the phase of embodiment 2
Together, compound 19 is obtained.Mass spectrum m/z：944.17 (calculated values：944.41).
Embodiment 20：The synthesis of compound 20
By the R in embodiment 21With the R in embodiment 12Group replaces with R as implied above1And R2Group, other steps are equal
It is identical with embodiment, obtain compound 20.Mass spectrum m/z：792.63 (meters 792.35).
Contrast Application Example 1：
Transparent glass is taken for anode, in being dried as vacuum chamber after ultrasonic cleaning, 5 × 10 is evacuated to-5Pa, upper
, used as hole transmission layer, evaporation rate is 0.1nm/s to state vacuum evaporation NPB in anode grid substrate, and evaporation thickness is 70nm.In hole
Used as luminescent layer, doping concentration is 15wt% to vacuum evaporation mCP/FIrpic in transport layer, and evaporation rate is 0.005nm/s, is steamed
Plating thickness is 30nm.The vacuum evaporation Alq on luminescent layer3Used as electron transfer layer, evaporation rate is 0.01nm/s, evaporation thickness
It is 50nm.Vacuum evaporation Al layers used as negative electrode on the electron transport layer, and thickness is 200nm.
Application example 1：
Transparent glass is taken for anode, in being dried as vacuum chamber after ultrasonic cleaning, 5 × 10 is evacuated to-5Pa, upper
, used as hole transmission layer, evaporation rate is 0.1nm/s to state vacuum evaporation NPB in anode grid substrate, and evaporation thickness is 70nm.In hole
Used as luminescent layer, doping concentration is 15wt% to vacuum evaporation compound 1/FIrpic in transport layer, and evaporation rate is 0.005nm/
S, evaporation thickness is 30nm.The vacuum evaporation Alq on luminescent layer3Used as electron transfer layer, evaporation rate is 0.01nm/s, evaporation
Thickness is 50nm.Vacuum evaporation Al layers used as negative electrode on the electron transport layer, and thickness is 200nm.
Application example 2：
Change the compound 1 in Application Example 1 into compound 2.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 3：
Change the compound 1 in Application Example 1 into compound 3.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 4：
Change the compound 1 in Application Example 1 into compound 4.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 5：
Change the compound 1 in Application Example 1 into compound 5.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 6：
Change the compound 1 in Application Example 1 into compound 6.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 7：
Change the compound 1 in Application Example 1 into compound 7.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 8：
Change the compound 1 in Application Example 1 into compound 8.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 9：
Change the compound 1 in Application Example 1 into compound 9.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 10：
Change the compound 1 in Application Example 1 into compound 10.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 11：
Change the compound 1 in Application Example 1 into compound 11.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 12：
Change the compound 1 in Application Example 1 into compound 12.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 13：
Change the compound 1 in Application Example 1 into compound 13.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 14：
Change the compound 1 in Application Example 1 into compound 14.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 15：
Change the compound 1 in Application Example 1 into compound 15.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 16：
Change the compound 1 in Application Example 1 into compound 16.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 17：
Change the compound 1 in Application Example 1 into compound 17.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 18：
Change the compound 1 in Application Example 1 into compound 18.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 19：
Change the compound 1 in Application Example 1 into compound 19.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 20：
Change the compound 1 in Application Example 1 into compound 20.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Measurement embodiment 1：The luminescent properties of comparative sample and sample 1-20, measurement comparative sample and sample 1-20 are
Using Keithley SMU235, PR650 evaluates driving voltage, luminous efficiency, external quantum efficiency.Comparative sample and sample 1-
20 are equally tested.The results are shown in Table 1：
The characteristics of luminescence of luminescent device prepared by the embodiment of the present invention of table 1
From the above, it can be seen that the organic luminescent device prepared using the benzo fluorene kind derivative that the present invention is provided, is lighted
Efficiency reaches as high as 8.7cd/A, and driving voltage is minimum can reach 3.2V, and maximum external quantum efficiency is 19.7%, above device
The luminous key index of part is significantly improved compared with comparative sample.
Although the present invention has carried out special description with exemplary embodiment, but it is understood that without departing from claim
In the case of the spirit and scope of the invention for being limited, those of ordinary skill in the art can carry out various forms and details to it
On change.
Claims (8)
1. a kind of benzo fluorene kind derivative, shown in its general structure such as formula (I)：
Wherein, A1-A8It is independent selected from hydrogen, substituted or unsubstituted alkyl or substituted or unsubstituted aromatic hydrocarbyl；R1、R2
It is independent selected from hydrogen, it is deuterium, fluorine, substituted or unsubstituted aromatic hydrocarbyl, substituted or unsubstituted arylamine, substituted or unsubstituted
Any one in aromatic heterocycle.
2. a kind of benzo fluorene kind derivative according to claim 1, it is characterised in that A1-A8It is independent selected from hydrogen, substitution
Or unsubstituted C1-C50 alkyl or substituted or unsubstituted C6-C50 aromatic hydrocarbyls；R1、R2It is independent selected from hydrogen, deuterium, fluorine,
Substituted or unsubstituted C6-C50 aromatic hydrocarbyls, substituted or unsubstituted C6-C50 arylamine, substituted or unsubstituted C12-C50
Any one in carbazole derivates.
3. a kind of benzo fluorene kind derivative according to claim 1, it is characterised in that A1-A8It is independent selected from hydrogen, substitution
Or unsubstituted C1-C30 alkyl or substituted or unsubstituted C6-C30 aromatic hydrocarbyls；R1、R2It is independent selected from hydrogen, substitution or
Unsubstituted C6-C30 aromatic hydrocarbyls, the arylamine of substituted or unsubstituted C6-C30, the click of substituted or unsubstituted C12-C30
Any one in Zole derivatives.
4. a kind of benzo fluorene kind derivative according to claim 1, it is characterised in that the aromatic hydrocarbyl is selected from benzene
Base, xenyl, terphenyl, deuterated phenyl, naphthyl, anthryl, phenanthryl, fluorenyl, the fluorenyl of spiral shell two, 9,9- diphenyl -9H- fluorenyls or
Pyrenyl.
5. a kind of benzo fluorene kind derivative according to claim 1, it is characterised in that the arylamine is selected from following structure
Any one：
6. a kind of benzo fluorene kind derivative according to claim 2, it is characterised in that the carbazole derivates are selected from as follows
Any one in structure：
7. a kind of benzo fluorene kind derivative according to claim 1~6 any one, it is characterised in that such as formula 1~20
Shown in one：
8. a kind of organic luminescent device, including first electrode, second electrode and be placed between two electrodes one or more are organic
Layer, at least one organic layer includes the benzo fluorene kind derivative as described in claim 1~7 any one.
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| CN107602440A (en) * | 2017-10-09 | 2018-01-19 | 长春海谱润斯科技有限公司 | A kind of benzo carbazole class electroluminescent organic material and its organic luminescent device |
| CN107629062A (en) * | 2017-10-09 | 2018-01-26 | 长春海谱润斯科技有限公司 | A kind of carbazole analog derivative and its organic luminescent device |
| CN107698486A (en) * | 2017-10-09 | 2018-02-16 | 长春海谱润斯科技有限公司 | A kind of benzo carbazole organic compound and its organic luminescent device |
| CN107698488A (en) * | 2017-10-09 | 2018-02-16 | 长春海谱润斯科技有限公司 | A kind of benzo carbazole analog derivative and its organic luminescent device |
| CN112877782A (en) * | 2021-01-12 | 2021-06-01 | 南京工业大学 | Molecular design strategy of two-dimensional organic single crystal and preparation method thereof |
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| CN104650090A (en) * | 2013-12-26 | 2015-05-27 | 北京鼎材科技有限公司 | Fluorene derivative containing carbazole-3-yl group and application thereof |
| CN104672230A (en) * | 2013-12-26 | 2015-06-03 | 北京鼎材科技有限公司 | Arylamino-containing fluorene type derivative and application thereof in electroluminescent device |
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| CN104650090A (en) * | 2013-12-26 | 2015-05-27 | 北京鼎材科技有限公司 | Fluorene derivative containing carbazole-3-yl group and application thereof |
| CN104672230A (en) * | 2013-12-26 | 2015-06-03 | 北京鼎材科技有限公司 | Arylamino-containing fluorene type derivative and application thereof in electroluminescent device |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107602440A (en) * | 2017-10-09 | 2018-01-19 | 长春海谱润斯科技有限公司 | A kind of benzo carbazole class electroluminescent organic material and its organic luminescent device |
| CN107629062A (en) * | 2017-10-09 | 2018-01-26 | 长春海谱润斯科技有限公司 | A kind of carbazole analog derivative and its organic luminescent device |
| CN107698486A (en) * | 2017-10-09 | 2018-02-16 | 长春海谱润斯科技有限公司 | A kind of benzo carbazole organic compound and its organic luminescent device |
| CN107698488A (en) * | 2017-10-09 | 2018-02-16 | 长春海谱润斯科技有限公司 | A kind of benzo carbazole analog derivative and its organic luminescent device |
| CN112877782A (en) * | 2021-01-12 | 2021-06-01 | 南京工业大学 | Molecular design strategy of two-dimensional organic single crystal and preparation method thereof |
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