CN107652189A - A kind of fluorene kind derivative and its organic luminescent device - Google Patents

A kind of fluorene kind derivative and its organic luminescent device Download PDF

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CN107652189A
CN107652189A CN201711089080.2A CN201711089080A CN107652189A CN 107652189 A CN107652189 A CN 107652189A CN 201711089080 A CN201711089080 A CN 201711089080A CN 107652189 A CN107652189 A CN 107652189A
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unsubstituted
substituted
fluorene
compound
derivative
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蔡辉
孙敬
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Changchun Haipurunsi Technology Co Ltd
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The invention discloses a kind of fluorene kind derivative and its organic luminescent device, is related to organic optoelectronic materials technology.The conjugated system of the fluorene kind derivative of the present invention is larger, therefore has higher hole mobility, shows preferable hole transport performance, and fluorene kind derivative of the invention also has preferable heat endurance and dissolubility in addition, is advantageous to material filming；Using organic luminescent device of the fluorene kind derivative of the present invention as organic matter layer, there are relatively low driving voltage, higher luminous efficiency and luminous brightness, and there is longer service life.

Description

A kind of fluorene kind derivative and its organic luminescent device
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to a kind of fluorene kind derivative and its organic illuminator Part.
Background technology
Organic photoelectrical material is the organic material for having the generation of photon and electronics, conversion and transmission characteristic.At present, it is organic Photoelectric material is applied to organic luminescent device (Organic Light-Emitting Diode, OLED).OLED refers to have The device that machine photoelectric material lights in the presence of electric current or electric field, electric energy can be converted into luminous energy by it.In recent years OLED is just receiving more and more attention as FPD of new generation and solid state lighting technology.Compared to lcd technology, OLED with its low-power consumption, actively luminous, fast response time, high-contrast, no angle limit, the features such as Flexible Displays can be made, It is increasing to be applied to display and lighting field.
Usual OLED has a sandwich construction, including tin indium oxide (ITO) anode and metallic cathode and be placed in ito anode with Some organic photovoltaic layers between metallic cathode, such as hole injection layer (HIL), hole transmission layer (HTL), luminous material layer (EML), electron transfer layer (ETL) and electron injecting layer (EIL) etc..Under certain voltage driving, electronics is with hole respectively by the moon Pole is injected into electron transfer layer and hole transmission layer with anode, and both move to by electron transfer layer and hole transmission layer respectively Luminous material layer, forms the compound exciton of electron-hole when both meet combination in luminous material layer, and exciton is relaxed by luminous The form in Henan returns to ground state, so as to reach luminous purpose.
As the hole transmission layer in OLED, its basic role is to improve hole efficiency of transmission in the devices, and by electricity Son is effectively blocked in luminescent layer, realizes the maximum compound of carrier；Reduce energy wall of the hole in injection process simultaneously Build, the injection efficiency in hole is improved, so as to improve the brightness of device, efficiency and life-span.
At present, generally there is the problems such as operating voltage is high, luminous efficiency is low, service life is short in OLED.Thus, explore new Organic photoelectrical material for OLED is the emphasis direction that those skilled in the art study all the time.Come for hole transmission layer Say, traditionally material used, can not generally provide the gratifying characteristics of luminescence, therefore, it is still necessary to design new performance more Good hole mobile material is to improve OLED performance.
The content of the invention
Goal of the invention：In view of the above-mentioned problems, it is an object of the invention to provide a kind of fluorene kind derivative and its organic illuminator Part, the derivative are applied in an organic light emitting device, so as to reduce the driving of organic luminescent device as hole mobile material Voltage, improves luminous efficiency and the brightness of organic luminescent device, and extends the service life of organic luminescent device.
The above-mentioned technical purpose of the present invention is achieved through the following technical solutions：A kind of fluorene kind derivative, the derivative With the general structure as shown in Formula I：
Wherein, Ar1、Ar2The independent aryl selected from substituted or unsubstituted C6~C60, substituted or unsubstituted C3~ One kind in C60 heteroaryl；
L be selected from substituted or unsubstituted C6~C60 arlydene, substituted or unsubstituted C3~C60 heteroarylidene, take One kind in generation or unsubstituted C3~C60 alkenylene, substituted or unsubstituted C3~C60 alkynylene.
Preferably, Ar1、Ar2The independent aryl selected from substituted or unsubstituted C6~C30, substituted or unsubstituted C3~ One kind in C30 heteroaryl；
Arlydene of the L selected from substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 heteroarylidene in One kind.
Most preferably, Ar1、Ar2Independent is selected from substituted or unsubstituted phenyl, substituted or unsubstituted carbazyl, substitution Or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substitution It is or unsubstituted terphenyl, substituted or unsubstituted xenyl, substituted or unsubstituted Sanya phenyl, substituted or unsubstituted The fluorenyl of spiral shell two, substituted or unsubstituted pyridine radicals, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted dibenzo sila ring Pentadienyl, substituted or unsubstituted triaryl amido, substituted or unsubstituted triaryl phosphino-, substituted or unsubstituted three virtue Base boryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted indenyl, substituted or unsubstituted indyl, substitution do not take The furyl in generation, substituted or unsubstituted thienyl, substituted or unsubstituted dibenzothiophenes base, substituted or unsubstituted hexichol And furyl, substituted or unsubstituted quinolyl.
Preferably, the one kind of fluorene kind derivative of the invention in chemical constitution as follows：
Present invention also offers a kind of organic luminescent device, the organic luminescent device include negative electrode, anode and one or Multiple organic matter layers, for organic matter layer between negative electrode and anode, at least one layer in organic matter layer contains the invention described above Fluorene kind derivative.
Preferably, organic matter layer includes hole transmission layer, and hole transmission layer includes the fluorene kind derivative of the invention described above.
Beneficial effect：Compared with prior art, it is an advantage of the invention that the present invention fluorene kind derivative conjugated system compared with Greatly, therefore there is higher hole mobility, shows preferable hole transport performance, fluorene kind derivative of the invention is also in addition With preferable heat endurance and dissolubility, be advantageous to material filming；Using the fluorene kind derivative of the present invention as organic matter layer Organic luminescent device, there are relatively low driving voltage, higher luminous efficiency and luminous brightness, and there is longer use Life-span.
Embodiment
With reference to specific embodiment, the present invention is furture elucidated, it should be understood that these embodiments are merely to illustrate the present invention Rather than limitation the scope of the present invention, after the present invention has been read, various equivalences of the those skilled in the art to the present invention The modification of form falls within the application appended claims limited range.
A kind of fluorene kind derivative, the derivative have the general structure as shown in Formula I：
Wherein, Ar1、Ar2The independent aryl selected from substituted or unsubstituted C6~C60, substituted or unsubstituted C3~ One kind in C60 heteroaryl；
L be selected from substituted or unsubstituted C6~C60 arlydene, substituted or unsubstituted C3~C60 heteroarylidene, take One kind in generation or unsubstituted C3~C60 alkenylene, substituted or unsubstituted C3~C60 alkynylene.
Preferably, Ar1、Ar2The independent aryl selected from substituted or unsubstituted C6~C30, substituted or unsubstituted C3~ One kind in C30 heteroaryl；
Arlydene of the L selected from substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 heteroarylidene in One kind.
Most preferably, Ar1、Ar2Independent is selected from substituted or unsubstituted phenyl, substituted or unsubstituted carbazyl, substitution Or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substitution It is or unsubstituted terphenyl, substituted or unsubstituted xenyl, substituted or unsubstituted Sanya phenyl, substituted or unsubstituted The fluorenyl of spiral shell two, substituted or unsubstituted pyridine radicals, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted dibenzo sila ring Pentadienyl, substituted or unsubstituted triaryl amido, substituted or unsubstituted triaryl phosphino-, substituted or unsubstituted three virtue Base boryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted indenyl, substituted or unsubstituted indyl, substitution do not take The furyl in generation, substituted or unsubstituted thienyl, substituted or unsubstituted dibenzothiophenes base, substituted or unsubstituted hexichol And furyl, substituted or unsubstituted quinolyl.
According to the present invention, above-mentioned Ar1、Ar2On substituent independence selected from hydrogen, deuterium, amino, alkyl amino, hydroxyl, acyl Amido, acyloxy, C1~C10 alkoxy, C1~C10 alkyl, C3~C20 cycloalkyl, C6~C24 aryl, C6~ C24 aryloxy group, C6~C24 arylthio, C3~C24 heteroaryl, C3~C20 heterocyclic radical；
Substituent on L be selected from hydrogen, C1~C10 alkoxy, C1~C10 alkyl, C3~C20 cycloalkyl, C6~ C24 aryl, C6~C24 aryloxy group, C6~C24 arylthio, C3~C24 heteroaryl, C3~C20 heterocyclic radical.
Aryl of the present invention refers to after a hydrogen atom is minused on the aromatic core carbon of aromatic hydrocarbon molecule, is left the total of univalent perssad Claiming, it can be monocyclic aryl or fused ring aryl, and example may include phenyl, xenyl, naphthyl, anthryl, phenanthryl or pyrenyl etc., but Not limited to this.
Heteroaryl of the present invention refers to the group that one or more of aryl aromatic core carbon substitutes to obtain 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 pyridine radicals, pyrrole radicals, pyridine radicals, thienyl, furyl, indyl, quinolyl, isoquinolyl, benzo thiophene Fen base, benzofuranyl, dibenzofuran group, dibenzothiophenes base, carbazyl etc., but not limited to this.
Arlydene of the present invention refers to after minusing a hydrogen atom on two aromatic core carbon of aromatic hydrocarbon molecule respectively, is left two The general name of valency group, it can be monocyclic 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 of arlydene aromatic core carbon substitutes to obtain 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 be monocyclic heteroarylidene or Condensed ring heteroarylidene, example may include sub- pyridine radicals, sub- pyrrole radicals, sub- pyridine radicals, sub- thienyl, furylidene, sub- indyl, Sub- quinolyl, sub- isoquinolyl, sub- benzothienyl, sub- benzofuranyl, sub- dibenzofuran group, sub- dibenzothiophenes base, Sub- carbazyl etc., but not limited to this.
Alkenylene of the present invention refers to that the carbon atom at conjugated system both ends in olefin hydrocarbon molecules minuses a hydrogen atom respectively The alkylene formed, the alkenylene can be sub- mono alkenyl, alkadienylene etc., but not limited to this.
Alkynylene of the present invention refers to that the carbon atom at conjugated system both ends in alkynes molecule minuses a hydrogen atom respectively The alkylene formed, the alkynylene can be sub- single alkynyl, sub- diynyl etc., but not limited to this.
As an example, it is not particularly limited, the one kind of fluorene kind derivative of the invention in chemical constitution as follows：
The synthetic route of the fluorene kind derivative of the present invention is as follows：
Wherein, Ar1、Ar2The independent aryl selected from substituted or unsubstituted C6~C60, substituted or unsubstituted C3~ One kind in C60 heteroaryl；
L be selected from substituted or unsubstituted C6~C60 arlydene, substituted or unsubstituted C3~C60 heteroarylidene, take One kind in generation or unsubstituted C3~C60 alkenylene, substituted or unsubstituted C3~C60 alkynylene.
The synthesis step of above-mentioned fluorene kind derivative is as follows：
(1) compound I, compound II, t-BuONa, Pd (OAc) are sequentially added into round-bottomed flask2And ultrasonic deoxygenation Toluene, under nitrogen protection backflow overnight, question response liquid cooling after use ethyl acetate and water process, and the organic layer that will be obtained Use MgSO4Dry, decompression boils off solvent, obtains compound III crude product, and using silica gel as stationary phase, dichloromethane/hexane is to wash De- agent, carries out column chromatography by crude product, obtains compound III.
(2) compound III is added in round-bottomed flask, adding appropriate anhydrous THF makes its dissolving, at -78 DEG C At a temperature of, n-BuLi is added dropwise into reaction bulb, after reacting 0.5h, the fast drop trimethyl borate into reaction solution, temperature is delayed Slowly it is warmed to room temperature, continues to react 30min, after completion of the reaction, reaction solution is poured into diluted hydrochloric acid aqueous solution, there is solid matter precipitation And filtered, crude product crosses silicagel column and obtains compound IV.
(3) compound V is added in round-bottomed flask, adding toluene makes its dissolving, is added into solution to toluene sulphur Hydrazides, after reacting 2h under conditions of 80 DEG C, compound IV and K are sequentially added into reaction solution2CO3, back flow reaction 5h will be anti- Answer liquid to be cooled to room temperature, reaction solution is washed with deionized, organic phase obtains the production of Formula I through drying, concentration, column chromatography Product.
The synthetic route of the fluorene kind derivative of the present invention is not particularly limited, those skilled in the art institute can be used ripe The popular response known.
Present invention also offers a kind of organic luminescent device, the organic luminescent device include negative electrode, anode and one or Multiple organic matter layers, for organic matter layer between negative electrode and anode, at least one layer in organic matter layer contains the invention described above Fluorene kind derivative.
The organic matter layer of the organic luminescent device of the present invention has a single layer structure, or optionally have two of which or The sandwich construction of more organic matter layers layering.The present invention organic luminescent device can have hole injection layer, hole transmission layer, Luminous material layer, electron transfer layer, electron injecting layer or the cushion that is placed between anode and hole injection layer are as organic matter Layer.However, the structure not limited to this of organic luminescent device, but may include small number of organic matter layer.Contain the present invention's The thickness of the organic matter layer of fluorene kind derivative is not higher than 6 μm, preferably not higher than 0.3 μm, and more preferably 0.002~0.3 μm. If desired, the organic matter layer of the fluorene kind derivative containing the present invention, which can further include, as known in the art can carry out hole Injection, hole transport, the other materials of luminous, electric transmission and electron injection.
The organic luminescent device of the present invention can be prepared by known methods using known materials, only can be at one layer or more The fluorene kind derivative of the present invention is included in layer organic matter layer.
The fluorene kind derivative of the present invention specifically can be as the hole transmission layer for preparing organic luminescent device.What is used is organic Luminescent device is preferably：The ITO being attached on transparent glass makees as anode, hole injection layer, fluorene kind derivative of the invention For hole transmission layer, luminous material layer, hole blocking layer, electron transfer layer, electron injecting layer, metallic cathode.
The organic luminescent device of the present invention can be widely applied to FPD, solid state lighting, Organophotoreceptor or organic thin The fields such as film transistor.
The present invention has no particular limits to the raw material employed in following examples, can be for commercially available prod or using this Preparation method known to art personnel is prepared.
Embodiment 1：
Compound III-1 preparation
Sequentially added into round-bottomed flask compound I-1 (12.5g, 73.8mmol), compound II-1 (20.9g, 73.8mmol)、t-BuONa(10.7g,111mmol)、Pd(OAc)2(0.33g, 1.47mmol) and the toluene of ultrasonic deoxygenation (1.5L), under nitrogen protection backflow overnight, ethyl acetate and water process, and the organic layer that will be obtained are used after the cooling of question response liquid Use MgSO4Dry, decompression boils off solvent, obtains compound III-1 crude product, using silica gel as stationary phase, dichloromethane/hexane is Eluant, eluent, crude product is subjected to column chromatography, obtains compound III-1 (18.7g, 78%).Mass spectrum m/z：Theoretical value：324.22；It is real Measured value：326.31.Theoretical elemental content (%) C18H14BrN：C,66.68；H,4.35；Br,24.64；N,4.32；Survey element Content (%)：C,66.64；H,4.38；Br,24.62；N,4.31.The above results confirm that it is target product to obtain product.
Compound IV-1 preparation
Compound III-1 (16.2g, 50mmol) is added in round-bottomed flask, adding appropriate anhydrous THF makes its molten Solution, at a temperature of -78 DEG C, n-BuLi (4.9ml, 60mmol) is added dropwise into reaction bulb, it is fast into reaction solution after reacting 0.5h Trimethyl borate (7.8g, 75mmol) is added dropwise in speed, and temperature is slowly increased into room temperature, continues to react 30min, after completion of the reaction, will Reaction solution is poured into diluted hydrochloric acid aqueous solution, is had solid matter to separate out and is filtered, crude product crosses silicagel column and obtains compound IV-1 (10.8g, 75%).Mass spectrum m/z：Theoretical value：289.14；Measured value：291.14.Theoretical elemental content (%) C18H16BNO2：C, 74.77；H,5.58；B,3.74；N,4.84；O,11.07；Survey constituent content (%)：C,74.75；H,5.61；B,3.72；N, 4.83；O,11.04.The above results confirm that it is target product to obtain product.
Compound TM1 preparation
Compound V (5.4g, 30mmol) is added in round-bottomed flask, adding toluene makes its dissolving, adds into solution Enter unifor (8.4g, 45mmol), after reacting 2h under conditions of 80 DEG C, compound is sequentially added into reaction solution IV-1 (13.0g, 45mmol) and K2CO3(12.4g, 90mmol), back flow reaction 5h, reaction solution is cooled to room temperature, uses deionization Water washing reaction solution, organic phase obtain compound TM1 (10.1g, 82%) through drying, concentration, column chromatography.Mass spectrum m/z：It is theoretical Value：409.53；Measured value：411.69.Theoretical elemental content (%) C31H23N：C,90.92；H,5.66；N,3.42；Survey element Content (%)：C,90.89；H,5.68；N,3.41.The above results confirm that it is target product to obtain product.
Embodiment 2:
Compound III-2 preparation
Sequentially added into round-bottomed flask compound I-2 (23.7g, 73.8mmol), compound II-2 (20.9g, 73.8mmol)、t-BuONa(10.7g,111mmol)、Pd(OAc)2(0.33g, 1.47mmol) and the toluene of ultrasonic deoxygenation (1.5L), under nitrogen protection backflow overnight, ethyl acetate and water process, and the organic layer that will be obtained are used after the cooling of question response liquid Use MgSO4Dry, decompression boils off solvent, obtains compound III-2 crude product, using silica gel as stationary phase, dichloromethane/hexane is Eluant, eluent, crude product is subjected to column chromatography, obtains compound III-2 (28.8g, 82%).Mass spectrum m/z：Theoretical value：476.41；It is real Measured value：478.54.Theoretical elemental content (%) C30H22BrN：C,75.63；H,4.65；Br,16.77；N,2.94；Survey element Content (%)：C,75.61；H,4.68；Br,16.75；N,2.93.The above results confirm that it is target product to obtain product.
Compound IV-2 preparation
Compound III-2 (23.8g, 50mmol) is added in round-bottomed flask, adding appropriate anhydrous THF makes its molten Solution, at a temperature of -78 DEG C, n-BuLi (4.9ml, 60mmol) is added dropwise into reaction bulb, it is fast into reaction solution after reacting 0.5h Trimethyl borate (7.8g, 75mmol) is added dropwise in speed, and temperature is slowly increased into room temperature, continues to react 30min, after completion of the reaction, will Reaction solution is poured into diluted hydrochloric acid aqueous solution, is had solid matter to separate out and is filtered, crude product crosses silicagel column and obtains compound IV-2 (16.3g, 74%).Mass spectrum m/z：Theoretical value：441.33；Measured value：443.47.Theoretical elemental content (%) C30H24BNO2：C, 81.64；H,5.48；B,2.45；N,3.17；O,7.25；Survey constituent content (%)：C,81.61；H,5.52；B,2.43；N, 3.16；O,7.23.The above results confirm that it is target product to obtain product.
Compound TM2 preparation
Compound V (5.4g, 30mmol) is added in round-bottomed flask, adding toluene makes its dissolving, adds into solution Enter unifor (8.4g, 45mmol), after reacting 2h under conditions of 80 DEG C, compound is sequentially added into reaction solution IV-2 (19.8g, 45mmol) and K2CO3(12.4g, 90mmol), back flow reaction 5h, reaction solution is cooled to room temperature, uses deionization Water washing reaction solution, organic phase obtain compound TM2 (13.5g, 80%) through drying, concentration, column chromatography.Mass spectrum m/z：It is theoretical Value：561.73；Measured value：563.87.Theoretical elemental content (%) C43H31N：C,91.94；H,5.56；N,2.49；Survey element Content (%)：C,91.91；H,5.59；N,2.44.The above results confirm that it is target product to obtain product.
Embodiment 3:
Compound III-3 preparation
Sequentially added into round-bottomed flask compound I-3 (19.9g, 73.8mmol), compound II-3 (20.9g, 73.8mmol)、t-BuONa(10.7g,111mmol)、Pd(OAc)2(0.33g, 1.47mmol) and the toluene of ultrasonic deoxygenation (1.5L), under nitrogen protection backflow overnight, ethyl acetate and water process, and the organic layer that will be obtained are used after the cooling of question response liquid Use MgSO4Dry, decompression boils off solvent, obtains compound III-3 crude product, using silica gel as stationary phase, dichloromethane/hexane is Eluant, eluent, crude product is subjected to column chromatography, obtains compound III-3 (23.5g, 75%).Mass spectrum m/z：Theoretical value：424.33；It is real Measured value：426.47.Theoretical elemental content (%) C26H18BrN：C,73.59；H,4.28；Br,18.83；N,3.30；Survey element Content (%)：C,73.54；H,4.31；Br,18.82；N,3.27.The above results confirm that it is target product to obtain product.
Compound IV-3 preparation
Compound III-3 (21.2g, 50mmol) is added in round-bottomed flask, adding appropriate anhydrous THF makes its molten Solution, at a temperature of -78 DEG C, n-BuLi (4.9ml, 60mmol) is added dropwise into reaction bulb, it is fast into reaction solution after reacting 0.5h Trimethyl borate (7.8g, 75mmol) is added dropwise in speed, and temperature is slowly increased into room temperature, continues to react 30min, after completion of the reaction, will Reaction solution is poured into diluted hydrochloric acid aqueous solution, is had solid matter to separate out and is filtered, crude product crosses silicagel column and obtains compound IV-3 (13.8g, 71%).Mass spectrum m/z：Theoretical value：389.25；Measured value：391.31.Theoretical elemental content (%) C26H20BNO2：C, 80.22；H,5.18；B,2.78；N,3.60；O,8.22；Survey constituent content (%)：C,80.18；H,5.22；B,2.77；N, 3.59；O,8.21.The above results confirm that it is target product to obtain product.
Compound TM3 preparation
Compound V (5.4g, 30mmol) is added in round-bottomed flask, adding toluene makes its dissolving, adds into solution Enter unifor (8.4g, 45mmol), after reacting 2h under conditions of 80 DEG C, compound is sequentially added into reaction solution IV-3 (17.5g, 45mmol) and K2CO3(12.4g, 90mmol), back flow reaction 5h, reaction solution is cooled to room temperature, uses deionization Water washing reaction solution, organic phase obtain compound TM3 (12.8g, 84%) through drying, concentration, column chromatography.Mass spectrum m/z：It is theoretical Value：509.65；Measured value：511.77.Theoretical elemental content (%) C39H27N：C,91.91；H,5.34；N,2.75；Survey element Content (%)：C,91.88；H,5.37；N,2.74.The above results confirm that it is target product to obtain product.
Embodiment 4：
Compound III-11 preparation
Sequentially added into round-bottomed flask compound I-11 (26.7g, 73.8mmol), compound II-11 (20.9g, 73.8mmol)、t-BuONa(10.7g,111mmol)、Pd(OAc)2(0.33g, 1.47mmol) and the toluene of ultrasonic deoxygenation (1.5L), under nitrogen protection backflow overnight, ethyl acetate and water process, and the organic layer that will be obtained are used after the cooling of question response liquid Use MgSO4To dry, decompression boils off solvent, obtains compound III-11 crude product, using silica gel as stationary phase, dichloromethane/hexane For eluant, eluent, crude product is subjected to column chromatography, obtains compound III-11 (29.7g, 78%).Mass spectrum m/z：Theoretical value：516.48； Measured value：518.57.Theoretical elemental content (%) C33H26BrN：C,76.74；H,5.07；Br,15.47；N,2.71；Actual measurement member Cellulose content (%)：C,76.72；H,5.11；Br,15.46；N,2.70.The above results confirm that it is target product to obtain product.
Compound IV-11 preparation
Compound III-11 (25.8g, 50mmol) is added in round-bottomed flask, adding appropriate anhydrous THF makes it Dissolving, at a temperature of -78 DEG C, n-BuLi (4.9ml, 60mmol) is added dropwise into reaction bulb, after reacting 0.5h, into reaction solution Fast drop trimethyl borate (7.8g, 75mmol), room temperature is slowly increased to by temperature, continues to react 30min, after completion of the reaction, Reaction solution is poured into diluted hydrochloric acid aqueous solution, has solid matter to separate out and is filtered, crude product crosses silicagel column and obtains compound IV- 11 (18.1g, 75%).Mass spectrum m/z：Theoretical value：481.40；Measured value：483.52.Theoretical elemental content (%) C33H28BNO2： C,82.34；H,5.86；B,2.25；N,2.91；O,6.65；Survey constituent content (%)：C,82.31；H,5.90；B,2.24；N, 2.90；O,6.66.The above results confirm that it is target product to obtain product.
Compound TM11 preparation
Compound V (5.4g, 30mmol) is added in round-bottomed flask, adding toluene makes its dissolving, adds into solution Enter unifor (8.4g, 45mmol), after reacting 2h under conditions of 80 DEG C, compound is sequentially added into reaction solution IV-11 (21.7g, 45mmol) and K2CO3(12.4g, 90mmol), back flow reaction 5h, reaction solution is cooled to room temperature, spend from Sub- water washing reaction solution, organic phase obtain compound TM11 (15.2g, 84%) through drying, concentration, column chromatography.Mass spectrum m/z：Reason By value：601.79；Measured value：603.85.Theoretical elemental content (%) C46H35N：C,91.81；H,5.86；N,2.33；Actual measurement member Cellulose content (%)：C,91.78；H,5.89；N,2.31.The above results confirm that it is target product to obtain product.
Embodiment 5：
Compound III-33 preparation
Sequentially added into round-bottomed flask compound I-33 (16.8g, 73.8mmol), compound II-33 (26.5g, 73.8mmol)、t-BuONa(10.7g,111mmol)、Pd(OAc)2(0.33g, 1.47mmol) and the toluene of ultrasonic deoxygenation (1.5L), under nitrogen protection backflow overnight, ethyl acetate and water process, and the organic layer that will be obtained are used after the cooling of question response liquid Use MgSO4To dry, decompression boils off solvent, obtains compound III-33 crude product, using silica gel as stationary phase, dichloromethane/hexane For eluant, eluent, crude product is subjected to column chromatography, obtains compound III-33 (26.7g, 79%).Mass spectrum m/z：Theoretical value：458.40； Measured value：460.55.Theoretical elemental content (%) C27H24BrNO：C,70.75；H,5.28；Br,17.43；N,3.06；O, 3.49；Survey constituent content (%)：C,70.73；H,5.34；Br,17.42；N,3.05；O,3.47.The above results confirm to obtain Product is target product.
Compound IV-33 preparation
Compound III-33 (22.9g, 50mmol) is added in round-bottomed flask, adding appropriate anhydrous THF makes it Dissolving, at a temperature of -78 DEG C, n-BuLi (4.9ml, 60mmol) is added dropwise into reaction bulb, after reacting 0.5h, into reaction solution Fast drop trimethyl borate (7.8g, 75mmol), room temperature is slowly increased to by temperature, continues to react 30min, after completion of the reaction, Reaction solution is poured into diluted hydrochloric acid aqueous solution, has solid matter to separate out and is filtered, crude product crosses silicagel column and obtains compound IV- 33 (16.3g, 77%).Mass spectrum m/z：Theoretical value：423.32；Measured value：425.46.Theoretical elemental content (%) C27H26BNO3： C,76.61；H,6.19；B,2.55；N,3.31；O,11.34；Survey constituent content (%)：C,76.58；H,6.24；B,2.54； N,3.29；O,11.35.The above results confirm that it is target product to obtain product.
Compound TM33 preparation
Compound V (5.4g, 30mmol) is added in round-bottomed flask, adding toluene makes its dissolving, adds into solution Enter unifor (8.4g, 45mmol), after reacting 2h under conditions of 80 DEG C, compound is sequentially added into reaction solution IV-33 (19.0g, 45mmol) and K2CO3(12.4g, 90mmol), back flow reaction 5h, reaction solution is cooled to room temperature, spend from Sub- water washing reaction solution, organic phase obtain compound TM33 (13.4g, 82%) through drying, concentration, column chromatography.Mass spectrum m/z：Reason By value：543.71；Measured value：545.83.Theoretical elemental content (%) C40H33NO：C,88.36；H,6.12；N,2.58；O, 2.94；Survey constituent content (%)：C,88.34；H,6.17；N,2.57；O,2.92.The above results confirm that it is target to obtain product Product.
Embodiment 6：
Compound III-39 preparation
Sequentially added into round-bottomed flask compound I-39 (23.9g, 73.8mmol), compound II-39 (28.7g, 73.8mmol)、t-BuONa(10.7g,111mmol)、Pd(OAc)2(0.33g, 1.47mmol) and the toluene of ultrasonic deoxygenation (1.5L), under nitrogen protection backflow overnight, ethyl acetate and water process, and the organic layer that will be obtained are used after the cooling of question response liquid Use MgSO4To dry, decompression boils off solvent, obtains compound III-39 crude product, using silica gel as stationary phase, dichloromethane/hexane For eluant, eluent, crude product is subjected to column chromatography, obtains compound III-39 (32.3g, 75%).Mass spectrum m/z：Theoretical value：584.54； Measured value：586.62.Theoretical elemental content (%) C34H22BrN3S：C,69.86；H,3.79；Br,13.67；N,7.19；S, 5.48；Survey constituent content (%)：C,69.83；H,3.87；Br,13.66；N,7.17；S,5.46.The above results confirm to obtain Product is target product.
Compound IV-39 preparation
Compound III-39 (29.2g, 50mmol) is added in round-bottomed flask, adding appropriate anhydrous THF makes it Dissolving, at a temperature of -78 DEG C, n-BuLi (4.9ml, 60mmol) is added dropwise into reaction bulb, after reacting 0.5h, into reaction solution Fast drop trimethyl borate (7.8g, 75mmol), room temperature is slowly increased to by temperature, continues to react 30min, after completion of the reaction, Reaction solution is poured into diluted hydrochloric acid aqueous solution, has solid matter to separate out and is filtered, crude product crosses silicagel column and obtains compound IV- 39 (19.8g, 72%).Mass spectrum m/z：Theoretical value：549.46；Measured value：551.57.Theoretical elemental content (%) C34H24BN3O2S：C,74.32；H,4.40；B,1.97；N,7.65；O,5.82；S,5.83；Survey constituent content (%)：C, 74.29；H,4.45；B,1.96；N,7.63；O,5.84；S,5.81.The above results confirm that it is target product to obtain product.
Compound TM39 preparation
Compound V (5.4g, 30mmol) is added in round-bottomed flask, adding toluene makes its dissolving, adds into solution Enter unifor (8.4g, 45mmol), after reacting 2h under conditions of 80 DEG C, compound is sequentially added into reaction solution IV-39 (24.7g, 45mmol) and K2CO3(12.4g, 90mmol), back flow reaction 5h, reaction solution is cooled to room temperature, spend from Sub- water washing reaction solution, organic phase obtain compound TM39 (16.1g, 80%) through drying, concentration, column chromatography.Mass spectrum m/z：Reason By value：669.85；Measured value：671.90.Theoretical elemental content (%) C47H31N3S：C,84.28；H,4.66；N,6.27；S, 4.79；Survey constituent content (%)：C,84.27；H,4.70；N,6.25；S,4.78.The above results confirm that it is target to obtain product Product.
Embodiment 7：
Compound III-43 preparation
Sequentially added into round-bottomed flask compound I-43 (29.6g, 73.8mmol), compound II-43 (29.4g, 73.8mmol)、t-BuONa(10.7g,111mmol)、Pd(OAc)2(0.33g, 1.47mmol) and the toluene of ultrasonic deoxygenation (1.5L), under nitrogen protection backflow overnight, ethyl acetate and water process, and the organic layer that will be obtained are used after the cooling of question response liquid Use MgSO4To dry, decompression boils off solvent, obtains compound III-43 crude product, using silica gel as stationary phase, dichloromethane/hexane For eluant, eluent, crude product is subjected to column chromatography, obtains compound III-43 (38.2g, 77%).Mass spectrum m/z：Theoretical value：672.71； Measured value：674.87.Theoretical elemental content (%) C45H38BrN：C,80.35；H,5.69；Br,11.88；N,2.08；Actual measurement member Cellulose content (%)：C,80.32；H,5.75；Br,11.87；N,2.06.The above results confirm that it is target product to obtain product.
Compound IV-43 preparation
Compound III-43 (33.6g, 50mmol) is added in round-bottomed flask, adding appropriate anhydrous THF makes it Dissolving, at a temperature of -78 DEG C, n-BuLi (4.9ml, 60mmol) is added dropwise into reaction bulb, after reacting 0.5h, into reaction solution Fast drop trimethyl borate (7.8g, 75mmol), room temperature is slowly increased to by temperature, continues to react 30min, after completion of the reaction, Reaction solution is poured into diluted hydrochloric acid aqueous solution, has solid matter to separate out and is filtered, crude product crosses silicagel column and obtains compound IV- 43 (24.2g, 76%).Mass spectrum m/z：Theoretical value：637.63；Measured value：639.79.Theoretical elemental content (%) C45H40BNO2： C,84.77；H,6.32；B,1.70；N,2.20；O,5.02；Survey constituent content (%)：C,84.74；H,6.39；B,1.69；N, 2.18；O,5.01.The above results confirm that it is target product to obtain product.
Compound TM43 preparation
Compound V (5.4g, 30mmol) is added in round-bottomed flask, adding toluene makes its dissolving, adds into solution Enter unifor (8.4g, 45mmol), after reacting 2h under conditions of 80 DEG C, compound is sequentially added into reaction solution IV-43 (28.7g, 45mmol) and K2CO3(12.4g, 90mmol), back flow reaction 5h, reaction solution is cooled to room temperature, spend from Sub- water washing reaction solution, organic phase obtain compound TM43 (19.8g, 87%) through drying, concentration, column chromatography.Mass spectrum m/z：Reason By value：758.02；Measured value：760.15.Theoretical elemental content (%) C58H47N：C,91.90；H,6.25；N,1.85；Actual measurement member Cellulose content (%)：C,91.87；H,6.29；N,1.84.The above results confirm that it is target product to obtain product.
Embodiment 8：
Compound III-60 preparation
Sequentially added into round-bottomed flask compound I-60 (30.8g, 73.8mmol), compound II-60 (28.3g, 73.8mmol)、t-BuONa(10.7g,111mmol)、Pd(OAc)2(0.33g, 1.47mmol) and the toluene of ultrasonic deoxygenation (1.5L), under nitrogen protection backflow overnight, ethyl acetate and water process, and the organic layer that will be obtained are used after the cooling of question response liquid Use MgSO4To dry, decompression boils off solvent, obtains compound III-60 crude product, using silica gel as stationary phase, dichloromethane/hexane For eluant, eluent, crude product is subjected to column chromatography, obtains compound III-60 (37.7g, 76%).Mass spectrum m/z：Theoretical value：672.74； Measured value：674.83.Theoretical elemental content (%) C43H34BrNSi：C,76.77；H,5.09；Br,11.88；N,2.08；Si, 4.17；Survey constituent content (%)：C,76.75；H,5.16；Br,11.87；N,2.06；Si,4.15.The above results confirm to obtain Product is target product.
Compound IV-60 preparation
Compound III-60 (33.6g, 50mmol) is added in round-bottomed flask, adding appropriate anhydrous THF makes it Dissolving, at a temperature of -78 DEG C, n-BuLi (4.9ml, 60mmol) is added dropwise into reaction bulb, after reacting 0.5h, into reaction solution Fast drop trimethyl borate (7.8g, 75mmol), room temperature is slowly increased to by temperature, continues to react 30min, after completion of the reaction, Reaction solution is poured into diluted hydrochloric acid aqueous solution, has solid matter to separate out and is filtered, crude product crosses silicagel column and obtains compound IV- 60 (24.9g, 74%).Mass spectrum m/z：Theoretical value：672.74；Measured value：674.86.Theoretical elemental content (%) C43H34BrNSi：C,76.77；H,5.09；Br,11.88；N,2.08；Si,4.17；Survey constituent content (%)：C,76.75；H, 5.17；Br,11.87；N,2.06；Si,4.14.The above results confirm that it is target product to obtain product.
Compound TM60 preparation
Compound V (5.4g, 30mmol) is added in round-bottomed flask, adding toluene makes its dissolving, adds into solution Enter unifor (8.4g, 45mmol), after reacting 2h under conditions of 80 DEG C, compound is sequentially added into reaction solution IV-60 (30.2g, 45mmol) and K2CO3(12.4g, 90mmol), back flow reaction 5h, reaction solution is cooled to room temperature, spend from Sub- water washing reaction solution, organic phase obtain compound TM60 (18.9g, 83%) through drying, concentration, column chromatography.Mass spectrum m/z：Reason By value：758.05；Measured value：760.18.Theoretical elemental content (%) C56H43NSi：C,88.73；H,5.72；N,1.85；Si, 3.70；Survey constituent content (%)：C,88.71；H,5.77；N,1.84；Si,3.68.The above results confirm that it is mesh to obtain product Mark product.
Other target products are synthesized with reference to above-described embodiment 1-8 synthetic method.
Application Example 1：The preparation of luminescent device 1
Selection ito glass is anode, is dried 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 The compound TM2 of the present invention is as hole transmission layer, evaporation thickness 30nm.The vacuum evaporation ADN conducts on hole transmission layer Luminescent material layer main body, 2% DPAVB is as doping, evaporation thickness 45nm.Vacuum evaporation BAlq makees on luminous material layer For hole blocking layer, evaporation thickness 10nm.The vacuum evaporation Alq on hole blocking layer3As electron injecting layer, evaporation thickness For 40nm.0.2nm LiF and 150nm Al is deposited on electron injecting layer as negative electrode.
Application Example 2：The preparation of luminescent device 2
Change the compound TM2 in Application Example 1 into compound TM11.
Application Example 3：The preparation of luminescent device 3
Change the compound TM2 in Application Example 1 into compound TM33.
Application Example 4：The preparation of luminescent device 4
Change the compound TM2 in Application Example 1 into compound TM43.
Application Example 5：The preparation of luminescent device 5
Change the compound TM2 in Application Example 1 into compound TM60.
Comparative example 1
Selection ito glass is anode, is dried 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.Vacuum evaporation ADN is as luminescent material layer main body on hole transmission layer, 2% DPAVB is as doping, evaporation thickness 45nm.Vacuum evaporation BAlq steams as hole blocking layer on luminous material layer Plating thickness is 10nm.The vacuum evaporation Alq on hole blocking layer3As electron injecting layer, evaporation thickness 40nm.Noted in electronics Enter to be deposited 0.2nm LiF and 150nm Al on layer as negative electrode.Application Example 1-5 of the present invention and comparative example 1 The characteristics of luminescence test result of the luminescent device of preparation is as shown in table 2.
Table 2
From Table 2, it can be seen that the fluorene kind derivative of the present invention is applied to organic luminescent device as hole mobile material In, the organic luminescent device shows relatively low driving voltage, higher luminous efficiency and longer service life, and has Preferable durability and reliability.

Claims (6)

1. a kind of fluorene kind derivative, it is characterised in that the derivative has the general structure as shown in Formula I：
Wherein, Ar1、Ar2The independent aryl selected from substituted or unsubstituted C6~C60, substituted or unsubstituted C3~C60 One kind in heteroaryl；
L be selected from substituted or unsubstituted C6~C60 arlydene, substituted or unsubstituted C3~C60 heteroarylidene, substitution or Unsubstituted C3~C60 alkenylene, substituted or unsubstituted C3~C60 alkynylene in one kind.
A kind of 2. fluorene kind derivative according to claim 1, it is characterised in that the Ar1、Ar2It is independent selected from substitution or Unsubstituted C6~C30 aryl, substituted or unsubstituted C3~C30 heteroaryl in one kind；
Arlydene of the L selected from substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 heteroarylidene in One kind.
A kind of 3. fluorene kind derivative according to claim 1, it is characterised in that the Ar1、Ar2It is independent selected from substitution or Unsubstituted phenyl, substituted or unsubstituted carbazyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substitution Or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted biphenyl Base, substituted or unsubstituted Sanya phenyl, the fluorenyl of substituted or unsubstituted spiral shell two, substituted or unsubstituted pyridine radicals, substitution or Unsubstituted pyrimidine radicals, substituted or unsubstituted dibenzo Silole base, substituted or unsubstituted triaryl amido, take Generation or unsubstituted triaryl phosphino-, substituted or unsubstituted triaryl boryl, substituted or unsubstituted pyrenyl, substitution or do not take The indenyl in generation, substituted or unsubstituted indyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substitution Or unsubstituted dibenzothiophenes base, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted quinolyl.
4. a kind of fluorene kind derivative according to claim 1, it is characterised in that the fluorene kind derivative is selected from as follows One kind in chemical constitution：
5. a kind of organic luminescent device, it is characterised in that the organic luminescent device includes negative electrode, anode and one or more Organic matter layer, for the organic matter layer between negative electrode and anode, at least one layer in the organic matter layer contains claim Fluorene kind derivative described in 1-4 any one.
6. a kind of organic luminescent device according to claim 5, it is characterised in that the organic matter layer includes hole transport Layer, the hole transmission layer include the fluorene kind derivative described in claim 1-4 any one.
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CN111196822A (en) * 2018-11-20 2020-05-26 北京夏禾科技有限公司 Compound containing silicon fluorenyl and fluorenyl structures and electroluminescent device containing compound
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CN111892614B (en) * 2019-05-06 2023-10-10 香港科技大学 Donor-acceptor type aggregation-induced emission luminescent agent with multi-stimulus response property
CN111892614A (en) * 2019-05-06 2020-11-06 香港科技大学 Donor-receptor type aggregation-induced emission luminescent agent with multi-stimulus responsiveness
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TWI759158B (en) * 2020-04-21 2022-03-21 南韓商三星Ｓｄｉ股份有限公司 Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device, and display device
CN113651785A (en) * 2021-09-17 2021-11-16 长春海谱润斯科技股份有限公司 Heterocyclic compound and organic light-emitting device thereof
CN113651785B (en) * 2021-09-17 2024-01-26 长春海谱润斯科技股份有限公司 Heterocyclic compound and organic light-emitting device thereof
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CN113698340A (en) * 2021-09-26 2021-11-26 长春海谱润斯科技股份有限公司 Carbazole derivative and organic electroluminescent device thereof
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