CN106083606B - A kind of 2,6- diphenyl naphthalene derivatives and its preparation method and application - Google Patents

A kind of 2,6- diphenyl naphthalene derivatives and its preparation method and application Download PDF

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CN106083606B
CN106083606B CN201610656011.4A CN201610656011A CN106083606B CN 106083606 B CN106083606 B CN 106083606B CN 201610656011 A CN201610656011 A CN 201610656011A CN 106083606 B CN106083606 B CN 106083606B
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naphthalene derivatives
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diphenyl naphthalene
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CN106083606A (en
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周雯庭
蔡辉
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Changchun Hyperions Technology Co Ltd
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Changchun Haipurunsi Technology Co Ltd
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    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
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    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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Abstract

The present invention provides a kind of 2,6 diphenyl naphthalene derivatives and its preparation method and application, is related to organic optoelectronic materials technology.By optimizing Molecular Design, the present invention obtained 2,6 diphenyl naphthalene derivatives have higher smooth extraction efficiency, available for preparing organic electroluminescence device, material is taken out especially as the light in organic electroluminescence device, the luminous efficiency of OLED device can be effectively improved, better than existing common OLED device.The present invention also provides a kind of preparation methods of 2,6 diphenyl naphthalene derivatives, and the preparation method is simple, raw material is easy to get.

Description

A kind of 2,6- diphenyl naphthalene derivatives and its preparation method and application
Technical field
The present invention relates to organic photoelectrical material technical fields, and in particular to one kind 2,6- diphenyl naphthalene derivatives and its preparation Methods and applications.
Background technology
ORGANIC ELECTROLUMINESCENCE DISPLAYS (organic electroluminesence Display) technology is known as with dream The flat panel display technology of feature is shown as unreal, because its luminescence mechanism is similar to light emitting diode (LED), so also referred to as OLED (organic light emitting diode).Since 2000, OLED receives the very big concern of industry, starts to step into production The industry stage.
OLED after decades of development, has been achieved for significant progress.Although its internal quantum efficiency already close to 100%, but external quantum efficiency only has about 20% or so.Most light is since substrate mode loses, surface plasma damages It loses and is limited in inside luminescent device with factors such as waveguiding effects, result in a large amount of energy losses.In order to which the light for improving device takes Go out efficiency, the use of light removing layer (Capping Layer, CPL) is current effective method.Light removing layer can reduce gold Belong to the surface plasma bulk effect of electrode, have the function that adjust light direction and light extraction efficiency.In addition light removing layer also needs to There are minimum absorption and more suitable refractive index in visible ray, three kinds of colors of red, green, blue are also required for very much like Property.But prepare one layer of CPL material not only needs to increase the cost budgeting of material more, it is also necessary to increase by one and individually steam Chamber is plated, this improves the manufacturing cost of OLED device.
Invention content
In view of this, the purpose of the present invention is to provide one kind 2,6- diphenyl naphthalene derivatives and preparation method thereof and should With.2,6- diphenyl naphthalene derivatives of the present invention are that a kind of broadband system has the function of the CPL materials of hole transport, and It is not significantly absorbed in visible light wave range, hole transmission layer and light removing layer can be used as simultaneously, improve the luminous efficiency of device, And the manufacturing cost of device is greatly saved.
The present invention provides one kind 2,6- diphenyl naphthalene derivatives, which is characterized in that structure formula (I) is as follows：
Wherein, Ar be the aryl of C6-C60, the thick aryl of C10-C60, five yuan of the hexa-member heterocycle of C5-C60 or C4-C60 Heterocycle, X are the aryl amine of C6-C30 or the condensed hetero ring of C6-C30.
Preferably, the Ar is the hexa-member heterocycle or C4-C30 of the aryl of C6-C30, the thick aryl of C10-C30, C5-C30 Five-ring heterocycles.
Preferably, the Ar is aryl, the thick aryl of C10-C30 or the five-ring heterocycles of C4-C30 of C6-C30.
Preferably, the X is the aryl amine of C12-C24 or the condensed hetero ring of C12-C24.
Still more preferably, 2, the 6- diphenyl naphthalene derivatives are any one in structure shown in TM1-TM32：
The present invention also provides the preparation method of one kind 2,6- diphenyl naphthalene derivatives, including：
Intermediate shown in formula (A) and formula (B) compound represented are obtained into formula by coupling reaction under nitrogen protection (I) 2,6- diphenyl naphthalene derivatives：
Wherein, Ar be the aryl of C6-C60, the thick aryl of C10-C60, five yuan of the hexa-member heterocycle of C5-C60 or C4-C60 Heterocycle, X are the aryl amine of C6-C30 or the condensed hetero ring of C6-C30.
The present invention also provides application of the above-mentioned 2,6- diphenyl naphthalene derivatives in organic electroluminescence device.
Preferably, the organic electroluminescence device includes anode, cathode, organic matter layer and light removing layer, organic matter layer Include hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer In at least one layer；
Contain the 2,6- diphenyl naphthalene derivatives in the smooth removing layer.
Preferably, the smooth removing layer and hole transmission layer contain 2, the 6- diphenyl naphthalene derivatives simultaneously.
The present invention also provides a kind of display devices, contain the organic electroluminescence device.
The present invention provides one kind 2,6- diphenyl naphthalene derivatives, which has shown in formula (I) Structure is the organic material of greater band gap, significantly do not absorbed in visible light wave range, can simultaneously as hole mobile material and Light take out material be applied to OLED device in, by 2, the 6- diphenyl naphthalene derivatives as light taking-up layer material can improve it is semi-transparent The transmitance of radio pole improves the external quantum efficiency of OLED device, it is seen that transmitance is up to more than 80% in optical range；By described 2, 6- diphenyl naphthalene derivatives are applied to as hole transmission layer and light removing layer in OLED device simultaneously, not only increase device Luminous efficiency, moreover it is possible to effectively save cost.
Specific embodiment
The invention will be further elaborated With reference to embodiment, but the present invention is not limited to following embodiment party Formula.
Present invention firstly provides one kind 2,6- diphenyl naphthalene derivatives, structural formula is：
Wherein, Ar be the aryl of C6-C60, the thick aryl of C10-C60, five yuan of the hexa-member heterocycle of C5-C60 or C4-C60 Heterocycle, X are the aryl amine of C6-C30 or the condensed hetero ring of C6-C30.
Preferably, Ar is the five of the aryl of C6-C30, the thick aryl of C10-C30, the hexa-member heterocycle of C5-C30 or C4-C30 Circle heterocyclic ring, X are the aryl amine of C6-C30 or the condensed hetero ring of C6-C30；
Optionally, the structure of Ar is as follows：
Optionally, the structure of X is as follows：
It is furthermore preferred that Ar is aryl, the thick aryl of C10-C30 or the five-ring heterocycles of C4-C30 of C6-C30, X C12- The aryl amine of C24 or the condensed hetero ring of C12-C24.
Most preferably, the structure of Ar is as follows：
The structure of X is as follows：
Specifically, 2, the 6- diphenyl naphthalene derivatives be preferably selected from it is any one in structure shown in following TM1-TM32 Kind：
The present invention also provides the preparation method of 2, the 6- diphenyl naphthalene derivatives, including：
Formula (A) compound represented and formula (B) compound represented are obtained into formula by coupling reaction under nitrogen protection (I) the 2,6- diphenyl naphthalene derivatives shown in：
Wherein, Ar be the aryl of C6-C60, the thick aryl of C10-C60, five yuan of the hexa-member heterocycle of C5-C60 or C4-C60 Heterocycle, X are the aryl amine of C6-C30 or the condensed hetero ring of C6-C30.
According to the present invention, the intermediate shown in formula (A) is prepared according to method as follows：
(1) by 2, the 6- dichloronaphtalenes shown in formula A-1 and simple substance bromine reaction, formula A-2 compounds represented are obtained；
(2) formula A-2 compounds represented with form reagent A r-MgBr are reacted, obtains the intermediate shown in formula (A).
The present invention is not particularly limited the reaction condition in step in the above method (1)~(2), using this field skill Reaction condition known to art personnel.
According to the present invention, by the intermediate shown in formula (A) and formula (B) compound represented under nitrogen protection by being coupled 2, the 6- diphenyl naphthalene derivatives shown in formula (I) are obtained by the reaction, the present invention does not have the coupling reaction special limitation, uses Coupling reaction well-known to those skilled in the art, the preparation method is simple, and raw material is easy to get.
Invention further provides application of the 2,6- diphenyl naphthalene derivatives in organic electroluminescence device. The organic electroluminescence device includes anode, cathode, organic matter layer and light removing layer, and organic matter layer is injected comprising hole At least one layer in layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer； It is preferred that contain 2, the 6- diphenyl naphthalene derivatives, the more preferable smooth removing layer and hole transmission layer in the smooth removing layer Contain the 2,6- diphenyl naphthalene derivatives simultaneously.
The device architecture of use is preferred, specially：Using transparent glass as anode；NPB or described 2,6- diphenyl Naphthalene derivatives (in TM1-TM32 any one) are as hole transmission layer；TCTA is as luminescent layer or is used as the same phosphorescence of main body Material doped (mass concentration of doping is 0.5~30.0%) is as luminescent layer；TPBI is as electron transfer layer；Using Al layers as Cathode；Finally 2, the 6- diphenyl naphthalene derivatives (in TM1~TM32 any one) are vaporized on above-mentioned cathode, are made For light removing layer.Above-mentioned device employs 2,6- diphenyl naphthalene derivatives of the present invention (in TM1-TM32 any one) As light removing layer or simultaneously as light removing layer and hole transmission layer, it is significantly improved compared with traditional devices luminous efficiency： For the luminous efficiency of above-mentioned device between 35cd/A~56cd/A, the luminous efficiency of traditional devices is 28cd/A.
The organic electroluminescence device can be used for the application neck such as flat-panel monitor, lighting source, direction board, signal lamp Domain.
Invention still further provides a kind of display device, including the organic electroluminescence device.
The present invention, but so as not to the limitation present invention are more fully explained by following embodiment.In the base of the description On plinth, those of ordinary skill in the art will be real in disclosed entire scope without creative efforts It applies the present invention and prepares other compounds according to the present invention.
Embodiment 1：The preparation of intermediate A
(1) synthesis of compound A-2：82ml fuming nitric aicds (29%SO is added in into 150ml three-necked flasks3), add successively Enter the 2,6- dichloronaphtalenes (compound A-1) of 11.0g (56mmol), the Br of 36g (225mmol)2, 0.25g Fe and 0.25g I2, It is vigorously stirred at 60-70 DEG C 6 hours.Mixed system is poured into ice water, is filtered, solid is water-soluble with sodium hydrogensulfite successively Liquid, sodium bicarbonate aqueous solution and water washing.It is recrystallized in toluene, obtains the compound A-2 of 26.1g (yield 91%).
(2) synthesis of intermediate A-a：The tetrahydrofuran of 32ml dryings is sequentially added into dry 150ml three-necked flasks With 5.8g (32mmol) phenyl-magnesium-bromide, the compound A-2 of 2.45g (4.0mmol) is dissolved in the tetrahydrofuran of 20ml dryings, In N2Protection under add in reaction system in, be stirred at room temperature 12 hours.At 0 DEG C, by the I of 6.35g (25mmol)2Add in reaction In system, stir 2 hours at room temperature.It is quenched and reacted with water, use CHCl3(3 × 100ml) is extracted.Organic layer uses the Asia of 2M successively Sodium bisulphate solution (2 × 200ml), saturated salt solution (50ml) and water (50ml) washing, are then dried with anhydrous magnesium sulfate. Magnesium sulfate solid is filtered, organic solvent, filtering are fallen in vacuum distillation, and obtained solid is washed with a small amount of toluene and hexane, obtained 1.4g crude product.Column chromatography (n-hexane/toluene=30:1, V/V) 1.17g intermediate As-a is obtained.Gross production rate is 43%.Mass spectrum m/ z：684.03 (calculated values：683.98).Theoretical elemental content (%) C34H22I2：C,59.67；H,3.24；I,37.09；Actual measurement member Cellulose content (%)：C,59.35；H,3.14；I,37.01.The above results confirm that it is target product to obtain product.
(3) synthesis of intermediate A-b：Other steps are identical with the synthesis step of intermediate A-a, and phenyl-magnesium-bromide is replaced Equimolar 1- naphthyl-magnesium bromides are changed to, obtain intermediate A-b.Mass spectrum m/z：884.62 (calculated values：884.58).Theoretical elemental Content (%) C50H30I2：C,67.89；H,3.42；I,28.69；Survey constituent content (%)：C,67.71；H,3.33；I, 28.44.The above results confirm that it is target product to obtain product.
(4) synthesis of intermediate A-c：Other steps are identical with the synthesis step of intermediate A-a, and phenyl-magnesium-bromide is replaced Equimolar 2- naphthyl-magnesium bromides are changed to, obtain intermediate A-c.Mass spectrum m/z：884.89 (calculated values：884.58).Theoretical elemental Content (%) C50H30I2：C,67.89；H,3.42；I,28.69；Survey constituent content (%)：C,67.82；H,3.39；I, 28.43.The above results confirm that it is target product to obtain product.
(5) synthesis of intermediate A-d：Other steps are identical with the synthesis step of intermediate A-a, and phenyl-magnesium-bromide is replaced Equimolar 2- thiophene magnesium bromide is changed to, obtains intermediate A-d.Mass spectrum m/z：708.55 (calculated values：708.46).Theoretical elemental Content (%) C26H14I2S4：C,44.08；H,1.99；I,35.83；S,18.10.Survey constituent content (%)：C,43.88；H, 1.67；I,35.48；S,18.07.The above results confirm that it is target product to obtain product.
Embodiment 2：The synthesis of compound TM1
The tetrakis triphenylphosphine palladium mixture of the intermediate A-a and 231mg (0.2mmol) of 684mg (1mmol) are added in In the toluene of 10ml removal air, in N2Under protection, system is heated to 60 DEG C, is stirred 5 minutes.It is sequentially added into system The sodium carbonate of the 2M of 636mg (2.2mmol) triphenylamine -4- boric acid, the ethyl alcohol of 2.5ml removal air and 5ml removal air is water-soluble Liquid stirs 21 hours at 80 DEG C.Reaction system is poured into a large amount of water, is extracted with dichloromethane.Organic layer uses saturation successively Saline solution and water washing, are dried with anhydrous magnesium sulfate, vacuum distillation.Residual solids are through column chromatography (hexanes/ch=4:4, V/V) after purification, recrystallized in hexane/chloroform mixed solution, obtain the compound TM1 of 597mg (0.65mmol), yield is 65%.Mass spectrum m/z：919.35 (calculated values：919.16).Theoretical elemental content (%) C70H50N2：C,91.47；H,5.48；N, 3.05.Survey constituent content (%)：C,91.24；H,5.41；N,3.03.The above results confirm that it is target product to obtain product.
Embodiment 3：The synthesis of compound TM2
Triphenylamine -4- boric acid in embodiment 2 is replaced with into equimolar 4- (N- (naphthalene -1- bases)-N- anilino-s) benzene boron Acid, other steps are same as Example 2, obtain compound TM2.Mass spectrum m/z：1019.36 (calculated value：1019.28).It is theoretical Constituent content (%) C78H54N2：C,91.91；H,5.34；N,2.75.Survey constituent content (%)：C,91.47；H,5.19；N, 2.44.The above results confirm that it is target product to obtain product.
Embodiment 4：The synthesis of compound TM3
Triphenylamine -4- boric acid in embodiment 2 is replaced with into equimolar 4- (N- (1- naphthalenes)-N- (2- naphthalenes) amido) Phenyl boric acid, other steps are same as Example 2, obtain compound TM3.Mass spectrum m/z：1119.66 (calculated value：1119.39). Theoretical elemental content (%) C86H58N2：C,92.27；H,5.22；N,2.50.Survey constituent content (%)：C,92.33；H,5.14； N,2.37.The above results confirm that it is target product to obtain product.
Embodiment 5：The synthesis of compound TM4
Triphenylamine -4- boric acid in embodiment 2 is replaced with into equimolar B- [4- [1,1'- biphenyl] -4- bases (9,9- bis- Methyl-9 H-fluorene -2- bases) amido] phenyl boric acid, other steps are same as Example 2, obtain compound TM4.Mass spectrum m/z： 1303.88 (calculated value：1303.67).Theoretical elemental content (%) C100H74N2：C,92.13；H,5.72；N,2.15.Actual measurement member Cellulose content (%)：C,91.01；H,5.64；N,2.12.The above results confirm that it is target product to obtain product.
Embodiment 6：The synthesis of compound TM5
Triphenylamine -4- boric acid in embodiment 2 is replaced with into equimolar B- [4- [two (4- methoxyphenyls) amidos]] Phenyl boric acid, other steps are same as Example 2, obtain compound TM5.Mass spectrum m/z：1039.46 (calculated value：1039.26). Theoretical elemental content (%) C74H58N2O4：C,85.52；H,5.63；N,2.70；O,6.16.Survey constituent content (%)：C, 85.36；H,5.57；N,2.48；O,6.05.The above results confirm that it is target product to obtain product.
Embodiment 7：The synthesis of compound TM6
Triphenylamine -4- boric acid in embodiment 2 is replaced with into equimolar 4- (dibiphenylyl -4- amino) phenyl boric acid, His step is same as Example 2, obtains compound TM6.Mass spectrum m/z：1223.88 (calculated value：1223.54).Theoretical elemental Content (%) C94H66N2：C,92.27；H,5.44；N,2.29.Survey constituent content (%)：C,92.13；H,5.29；N,2.17. The above results confirm that it is target product to obtain product.
Embodiment 8：The synthesis of compound TM7
Triphenylamine -4- boric acid in embodiment 2 is replaced with into equimolar 4- [two (4- tolyls) amine] phenyl] boric acid, Other steps are same as Example 2, obtain compound TM7.Mass spectrum m/z：975.34 (calculated values：975.27).Theoretical elemental Content (%) C74H58N2：C,91.13；H,5.99；N,2.87.Survey constituent content (%)：C,91.07；H,5.85；N,2.61. The above results confirm that it is target product to obtain product.
Embodiment 9：The synthesis of compound TM8
Triphenylamine -4- boric acid in embodiment 2 is replaced with into equimolar 4- carbazoles -9- base phenyl boric acids, other steps are equal It is same as Example 2, obtain compound TM8.Mass spectrum m/z：915.31 (calculated values：915.13).Theoretical elemental content (%) C70H46N2：C,91.87；H,5.07；N,3.06.Survey constituent content (%)：C,91.65；H,5.01；N,3.03.The above results Confirm that it is target product to obtain product.
Embodiment 10：The synthesis of compound TM9
The tetrakis triphenylphosphine palladium mixture of the intermediate A-b and 231mg (0.2mmol) of 884mg (1mmol) are added in In the benzene of 10ml removal air, in N2Under protection, system is heated to 60 DEG C, is stirred 5 minutes.It is sequentially added into system The sodium carbonate of the 2M of 636mg (2.2mmol) triphenylamine -4- boric acid, the ethyl alcohol of 2.5ml removal air and 5ml removal air is water-soluble Liquid stirs 21 hours at 80 DEG C.Reaction system is poured into a large amount of water, is extracted with dichloromethane.Organic layer uses saturation successively Saline solution and water washing, are dried with anhydrous magnesium sulfate, vacuum distillation.Residual solids are through column chromatography (hexanes/ch=4:4, V/V) after purification, recrystallized in hexane/chloroform mixed solution, obtain the compound TM9 of 705mg (0.63mmol), yield is 63%.Mass spectrum m/z：1119.46 calculated value：1119.39).Theoretical elemental content (%) C86H58N2：C,92.27；H,5.22；N, 2.50.Survey constituent content (%)：C,92.11；H,5.16；N,2.38.The above results confirm that it is target product to obtain product.
Embodiment 11：The synthesis of compound TM10
Triphenylamine -4- boric acid in embodiment 10 is replaced with into equimolar 4- (N- (naphthalene -1- bases)-N- anilino-s) benzene boron Acid, other steps are same as in Example 10, obtain compound TM10.Mass spectrum m/z：1219.74 (calculated value：1219.51).Reason Argument cellulose content (%) C94H62N2：C,92.58；H,5.12；N,2.30.Survey constituent content (%)：C,92.41；H,5.07；N, 2.11.The above results confirm that it is target product to obtain product.
Embodiment 12：The synthesis of compound TM11
Triphenylamine -4- boric acid in embodiment 10 is replaced with into equimolar 4- (N- (1- naphthalenes)-N- (2- naphthalenes) amine Base) phenyl boric acid, other steps are same as in Example 10, obtain compound TM11.Mass spectrum m/z：1319.96 (calculated value： 1319.63).Theoretical elemental content (%) C102H66N2：C,92.84；H,5.04；N,2.12.Survey constituent content (%)：C, 92.51；H,5.01；N,2.06.The above results confirm that it is target product to obtain product.
Embodiment 13：The synthesis of compound TM12
Triphenylamine -4- boric acid in embodiment 10 is replaced with into equimolar B- [4- [1,1'- biphenyl] -4- bases (9,9- bis- Methyl-9 H-fluorene -2- bases) amido] phenyl boric acid, other steps are same as in Example 10, obtain compound TM12.Mass spectrum m/z： 1504.24 (calculated value：1503.91).Theoretical elemental content (%) C116H82N2：C,92.64；H,5.50；N,1.86.Actual measurement member Cellulose content (%)：C,92.58；H,5.39；N,1.74.The above results confirm that it is target product to obtain product.
Embodiment 14：The synthesis of compound TM13
Triphenylamine -4- boric acid in embodiment 10 is replaced with into equimolar B- [4- [two (4- methoxyphenyls) amidos]] Phenyl boric acid, other steps are same as in Example 10, obtain compound TM13.Mass spectrum m/z：1239.64 (calculated value： 1239.50).Theoretical elemental content (%) C90H66N2O4：C,87.21；H,5.37；N,2.26；O,5.16.Survey constituent content (%)：C,87.14；H,5.23；N,2.14；O,5.03.The above results confirm that it is target product to obtain product.
Embodiment 15：The synthesis of compound TM14
Triphenylamine -4- boric acid in embodiment 10 is replaced with into equimolar 4- (dibiphenylyl -4- amino) phenyl boric acid, His step is same as in Example 10, obtains compound TM14.Mass spectrum m/z：1423.89 (calculated value：1423.78).Theoretical member Cellulose content (%) C110H74N2：C,92.79；H,5.24；N,1.97.Survey constituent content (%)：C,92.63；H,5.08；N, 1.86.The above results confirm that it is target product to obtain product.
Embodiment 16：The synthesis of compound TM15
Triphenylamine -4- boric acid in embodiment 10 is replaced with into equimolar 4- [two (4- tolyls) amine] phenyl] boric acid, Other steps are same as in Example 10, obtain compound TM15.Mass spectrum m/z：1175.64 (calculated value：1175.50).It is theoretical Constituent content (%) C90H66N2：C,91.96；H,5.66；N,2.38.Survey constituent content (%)：C,91.78；H,5.53；N, 2.18.The above results confirm that it is target product to obtain product.
Embodiment 17：The synthesis of compound TM16
Triphenylamine -4- boric acid in embodiment 10 is replaced with into equimolar 4- carbazoles -9- base phenyl boric acids, other steps are equal It is same as in Example 10, obtain compound TM16.Mass spectrum m/z：1115.63 (calculated value：1115.36).Theoretical elemental content (%) C86H54N2：C,92.61；H,4.88；N,2.51.Survey constituent content (%)：C,92.47；H,4.73；N,2.47.It is above-mentioned As a result confirm that it is target product to obtain product.
Embodiment 18：The synthesis of compound TM17
The tetrakis triphenylphosphine palladium mixture of the intermediate A-c and 231mg (0.2mmol) of 884mg (1mmol) are added in In the benzene of 10ml removal air, in N2Under protection, system is heated to 60 DEG C, is stirred 5 minutes.It is sequentially added into system The sodium carbonate of the 2M of 636mg (2.2mmol) triphenylamine -4- boric acid, the ethyl alcohol of 2.5ml removal air and 5ml removal air is water-soluble Liquid stirs 21 hours at 80 DEG C.Reaction system is poured into a large amount of water, is extracted with dichloromethane.Organic layer uses saturation successively Saline solution and water washing, are dried with anhydrous magnesium sulfate, vacuum distillation.Residual solids are through column chromatography (hexanes/ch=4:4, V/V) after purification, recrystallized in hexane/chloroform mixed solution, obtain the compound TM17 of 663mg (0.593mmol), yield It is 59%.Mass spectrum m/z：1119.64 (calculated value：1119.39).Theoretical elemental content (%) C86H58N2：C,92.27；H,5.22； N,2.50.Survey constituent content (%)：C,92.13；H,5.08；N,2.28.The above results confirm that it is target product to obtain product.
Embodiment 19：The synthesis of compound TM18
Triphenylamine -4- boric acid in embodiment 18 is replaced with into equimolar 4- (N- (naphthalene -1- bases)-N- anilino-s) benzene boron Acid, other steps are identical with embodiment 18, obtain compound TM18.Mass spectrum m/z：1219.68 (calculated value：1219.51).Reason Argument cellulose content (%) C94H62N2：C,92.58；H,5.12；N,2.30.Survey constituent content (%)：C,92.44；H,5.08；N, 2.16.The above results confirm that it is target product to obtain product.
Embodiment 20：The synthesis of compound TM19
Triphenylamine -4- boric acid in embodiment 18 is replaced with into equimolar 4- (N- (1- naphthalenes)-N- (2- naphthalenes) amine Base) phenyl boric acid, other steps are identical with embodiment 18, obtain compound TM19.Mass spectrum m/z：1319.77 (calculated value： 1319.63).Theoretical elemental content (%) C102H66N2：C,92.84；H,5.04；N,2.12.Survey constituent content (%)：C, 92.75；H,4.96；N,2.03.The above results confirm that it is target product to obtain product.
Embodiment 21：The synthesis of compound TM20
Triphenylamine -4- boric acid in embodiment 18 is replaced with into equimolar B- [4- [1,1'- biphenyl] -4- bases (9,9- bis- Methyl-9 H-fluorene -2- bases) amido] phenyl boric acid, other steps are identical with embodiment 18, obtain compound TM20.Mass spectrum m/z： 1503.99 (calculated value：1503.91).Theoretical elemental content (%) C116H82N2：C,92.64；H,5.50；N,1.86.Actual measurement member Cellulose content (%)：C,92.57；H,5.46；N,1.74.The above results confirm that it is target product to obtain product.
Embodiment 22：The synthesis of compound TM21
Triphenylamine -4- boric acid in embodiment 18 is replaced with into equimolar B- [4- [two (4- methoxyphenyls) amidos]] Phenyl boric acid, other steps are identical with embodiment 18, obtain compound TM21.Mass spectrum m/z：1239.66 (calculated value： 1239.50).Theoretical elemental content (%) C90H66N2O4：C,87.21；H,5.37；N,2.26；O,5.16.Survey constituent content (%)：C,87.06；H,5.23；N,2.17；O,5.09.The above results confirm that it is target product to obtain product.
Embodiment 23：The synthesis of compound TM22
Triphenylamine -4- boric acid in embodiment 18 is replaced with into equimolar 4- (dibiphenylyl -4- amino) phenyl boric acid, His step is identical with embodiment 18, obtains compound TM22.Mass spectrum m/z：1423.86 (calculated value：1423.78).Theoretical member Cellulose content (%) C110H74N2：C,92.79；H,5.24；N,1.97.Survey constituent content (%)：C,92.61；H,5.13；N, 1.88.The above results confirm that it is target product to obtain product.
Embodiment 24：The synthesis of compound TM23
Triphenylamine -4- boric acid in embodiment 18 is replaced with into equimolar 4- [two (4- tolyls) amine] phenyl] boric acid, Other steps are identical with embodiment 18, obtain compound TM23.Mass spectrum m/z：1175.71 (calculated value：1175.50).It is theoretical Constituent content (%) C90H66N2：C,91.96；H,5.66；N,2.38.Survey constituent content (%)：C,91.78；H,5.54；N, 2.26.The above results confirm that it is target product to obtain product.
Embodiment 25：The synthesis of compound TM24
Triphenylamine -4- boric acid in embodiment 18 is replaced with into equimolar 4- carbazoles -9- base phenyl boric acids, other steps are equal It is identical with embodiment 18, obtain compound TM24.Mass spectrum m/z：1115.47 (calculated value：1115.36).Theoretical elemental content (%) C86H54N2：C,92.61；H,4.88；N,2.51.Survey constituent content (%)：C,92.48；H,4.74；N,2.43.It is above-mentioned As a result confirm that it is target product to obtain product.
Embodiment 26：The synthesis of compound TM25
The tetrakis triphenylphosphine palladium mixture of the intermediate A-d and 231mg (0.2mmol) of 708mg (1mmol) are added in In the benzene of 10ml removal air, in N2Under protection, system is heated to 60 DEG C, is stirred 5 minutes.It is sequentially added into system The sodium carbonate of the 2M of 636mg (2.2mmol) triphenylamine -4- boric acid, the ethyl alcohol of 2.5ml removal air and 5ml removal air is water-soluble Liquid stirs 21 hours at 80 DEG C.Reaction system is poured into a large amount of water, is extracted with dichloromethane.Organic layer uses saturation successively Saline solution and water washing, are dried with anhydrous magnesium sulfate, vacuum distillation.Residual solids are through column chromatography (hexanes/ch=4:4, V/V) after purification, recrystallized in hexane/chloroform mixed solution, obtain the compound TM25 of 529mg (0.561mmol), yield It is 55%.Mass spectrum m/z：943.38 (calculated values：943.27).Theoretical elemental content (%) C62H42N2S4：C,78.94；H,4.49； N,2.97；S,13.60.Survey constituent content (%)：C,78.86；H,4.35；N,2.78；S,13.54.The above results confirmation obtains It is target product to obtain product.
Embodiment 27：The synthesis of compound TM26
Triphenylamine -4- boric acid in embodiment 26 is replaced with into equimolar 4- (N- (naphthalene -1- bases)-N- anilino-s) benzene boron Acid, other steps are identical with embodiment 26, obtain compound TM26.Mass spectrum m/z：1043.51 (calculated value：1043.39).Reason Argument cellulose content (%) C70H46N2S4：C,80.58；H,4.44；N,2.68；S,12.29.Survey constituent content (%)：C, 80.44；H,4.32；N,2.54；S,12.13.The above results confirm that it is target product to obtain product.
Embodiment 28：The synthesis of compound TM27
Triphenylamine -4- boric acid in embodiment 26 is replaced with into equimolar 4- (N- (1- naphthalenes)-N- (2- naphthalenes) amine Base) phenyl boric acid, other steps are identical with embodiment 26, obtain compound TM27.Mass spectrum m/z：1143.68 (calculated value： 1143.51).Theoretical elemental content (%) C78H50N2S4：C,81.93；H,4.41；N,2.45；S,11.22.Survey constituent content (%)：C,81.85；H,4.31；N,2.34；S,11.13.The above results confirm that it is target product to obtain product.
Embodiment 29：The synthesis of compound TM28
Triphenylamine -4- boric acid in embodiment 26 is replaced with into equimolar B- [4- [1,1'- biphenyl] -4- bases (9,9- bis- Methyl-9 H-fluorene -2- bases) amido] phenyl boric acid, other steps are identical with embodiment 26, obtain compound TM28.Mass spectrum m/z： 1327.88 (calculated value：1327.78).Theoretical elemental content (%) C92H66N2S4：C,83.22；H,5.01；N,2.11；S, 9.66.Survey constituent content (%)：C,83.07；H,4.93；N,2.04；S,9.57.The above results confirm that it is target to obtain product Product.
Embodiment 30：The synthesis of compound TM29
Triphenylamine -4- boric acid in embodiment 26 is replaced with into equimolar B- [4- [two (4- methoxyphenyls) amidos]] Phenyl boric acid, other steps are identical with embodiment 26, obtain compound TM29.Mass spectrum m/z：1063.48 (calculated value： 1063.37).Theoretical elemental content (%) C66H50N2O4S4：C,74.55；H,4.74；N,2.63；O,6.02；S,12.06.Actual measurement Constituent content (%)：C,74.36；H,4.59；N,2.51；O,5.94；S,11.89.The above results confirm that it is target to obtain product Product.
Embodiment 31：The synthesis of compound TM30
Triphenylamine -4- boric acid in embodiment 26 is replaced with into equimolar 4- (dibiphenylyl -4- amino) phenyl boric acid, His step is identical with embodiment 26, obtains compound TM30.Mass spectrum m/z：1247.74 (calculated value：1247.65).Theoretical member Cellulose content (%) C86H58N2S4：C,82.79；H,4.69；N,2.25；S,10.28.Survey constituent content (%)：C,82.65；H, 4.53；N,2.14；S,10.16.The above results confirm that it is target product to obtain product.
Embodiment 32：The synthesis of compound TM31
Triphenylamine -4- boric acid in embodiment 26 is replaced with into equimolar 4- [two (4- tolyls) amine] phenyl] boric acid, Other steps are identical with embodiment 26, obtain compound TM31.Mass spectrum m/z：999.46 (calculated values：999.38).Theoretical member Cellulose content (%) C66H50N2S4：C,79.32；H,5.04；N,2.80；S,12.83.Survey constituent content (%)：C,79.16；H, 4.93；N,2.67；S,12.74.The above results confirm that it is target product to obtain product.
Embodiment 33：The synthesis of compound TM32
Triphenylamine -4- boric acid in embodiment 26 is replaced with into equimolar 4- carbazoles -9- base phenyl boric acids, other steps are equal It is identical with embodiment 26, obtain compound TM32.Mass spectrum m/z：939.46 (calculated values：939.24).Theoretical elemental content (%) C62H38N2S4：C,79.28；H,4.08；N,2.98；S,13.66.Survey constituent content (%)：C,79.15；H,4.05；N, 2.86；S,13.54.The above results confirm that it is target product to obtain product.
Embodiment 34：The preparation of luminescent device 1
It is anode to choose transparent glass, is dried after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, Vacuum evaporation NPB is as hole transmission layer, evaporation rate 0.1nm/s, evaporation thickness 70nm in above-mentioned anode grid substrate.In sky Vacuum evaporation TCTA/FIrpic is as luminescent layer in the transport layer of cave, doping concentration 13wt%, evaporation rate 0.005nm/s, Evaporation thickness is 30nm.Vacuum evaporation TPBI is as electron transfer layer, evaporation rate 0.01nm/s, vapor deposition thickness on the light-emitting layer It spends for 50nm.It is used as cathode, thickness 200nm for vacuum evaporation Al layers on the electron transport layer.TM1ization is finally deposited on cathode Object is closed as light removing layer, evaporation rate 0.1nm/s, evaporation thickness 50nm.The device blue light-emitting, luminous efficiency are 38cd/A。
Embodiment 35：The preparation of luminescent device 2
It is anode to choose transparent glass, is dried after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, Vacuum evaporation NPB is as hole transmission layer, evaporation rate 0.1nm/s, evaporation thickness 70nm in above-mentioned anode grid substrate.In sky Vacuum evaporation TCTA/FIrpic is as luminescent layer in the transport layer of cave, doping concentration 13wt%, evaporation rate 0.005nm/s, Evaporation thickness is 30nm.Vacuum evaporation TPBI is as electron transfer layer, evaporation rate 0.01nm/s, vapor deposition thickness on the light-emitting layer It spends for 50nm.It is used as cathode, thickness 200nm for vacuum evaporation Al layers on the electron transport layer.TM14 is finally deposited on cathode Compound is as light removing layer, evaporation rate 0.1nm/s, evaporation thickness 50nm.The device blue light-emitting, luminous efficiency are 45cd/A。
Embodiment 36：The preparation of luminescent device 3
It is anode to choose transparent glass, is dried after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, Vacuum evaporation NPB is as hole transmission layer, evaporation rate 0.1nm/s, evaporation thickness 70nm in above-mentioned anode grid substrate.In sky Vacuum evaporation TCTA/FIrpic is as luminescent layer in the transport layer of cave, doping concentration 13wt%, evaporation rate 0.005nm/s, Evaporation thickness is 30nm.Vacuum evaporation TPBI is as electron transfer layer, evaporation rate 0.01nm/s, vapor deposition thickness on the light-emitting layer It spends for 50nm.It is used as cathode, thickness 200nm for vacuum evaporation Al layers on the electron transport layer.TM20 is finally deposited on cathode Compound is as light removing layer, evaporation rate 0.1nm/s, evaporation thickness 50nm.The device blue light-emitting, luminous efficiency are 35cd/A。
Embodiment 37：The preparation of luminescent device 4
It is anode to choose transparent glass, is dried after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, Vacuum evaporation NPB is as hole transmission layer, evaporation rate 0.1nm/s, evaporation thickness 70nm in above-mentioned anode grid substrate.In sky Vacuum evaporation TCTA/FIrpic is as luminescent layer in the transport layer of cave, doping concentration 13wt%, evaporation rate 0.005nm/s, Evaporation thickness is 30nm.Vacuum evaporation TPBI is as electron transfer layer, evaporation rate 0.01nm/s, vapor deposition thickness on the light-emitting layer It spends for 50nm.It is used as cathode, thickness 200nm for vacuum evaporation Al layers on the electron transport layer.TM32 is finally deposited on cathode Compound is as light removing layer, evaporation rate 0.1nm/s, evaporation thickness 50nm.The device blue light-emitting, luminous efficiency are 50cd/A。
Embodiment 38：The preparation of luminescent device 5
It is anode to choose transparent glass, is dried after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, Vacuum evaporation TM32 compounds are as hole transmission layer in above-mentioned anode grid substrate, evaporation rate 0.1nm/s, and evaporation thickness is 70nm.Vacuum evaporation TCTA/FIrpic is as luminescent layer on the hole transport layer, doping concentration 13wt%, and evaporation rate is 0.005nm/s, evaporation thickness 30nm.Vacuum evaporation TPBI is as electron transfer layer, evaporation rate on the light-emitting layer 0.01nm/s, evaporation thickness 50nm.It is used as cathode, thickness 200nm for vacuum evaporation Al layers on the electron transport layer.Finally exist TM32 compounds are deposited on cathode as light removing layer, evaporation rate 0.1nm/s, evaporation thickness 50nm.The device turns blue Light, luminous efficiency 56cd/A.
Comparative example：The preparation of luminescent device 6
It is anode to choose transparent glass, is dried after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, Vacuum evaporation NPB is as hole transmission layer, evaporation rate 0.1nm/s, evaporation thickness 70nm in above-mentioned anode grid substrate.In sky Vacuum evaporation TCTA/FIrpic is as luminescent layer in the transport layer of cave, doping concentration 13wt%, evaporation rate 0.005nm/s, Evaporation thickness is 30nm.Vacuum evaporation TPBI is as electron transfer layer, evaporation rate 0.01nm/s, vapor deposition thickness on the light-emitting layer It spends for 50nm.Finally on the electron transport layer vacuum evaporation Al layer as cathode, thickness 200nm.The device blue light-emitting shines Efficiency is 28cd/A.
Luminescent device Luminous efficiency (cd/A)
1 38
2 45
3 35
4 50
5 56
6 28
The above result shows that 2,6- diphenyl naphthalene derivatives of the invention take out layer material as light, applied to Organic Electricity In electroluminescence device, luminous efficiency is high, is luminous organic material of good performance.
Obviously, the explanation of above example is only intended to facilitate the understanding of the method and its core concept of the invention.It should refer to Go out, it, without departing from the principle of the present invention, can also be to this hair for the those of ordinary skill of the technical field Bright some improvement and modification can also be carried out, these improvement and modification are also fallen within the protection scope of the claims of the present invention.

Claims (9)

1. one kind 2,6- diphenyl naphthalene derivatives, which is characterized in that structure formula (I) is as follows：
Wherein, Ar be the aryl of C6-C60, the thick aryl of C10-C60, the hexa-member heterocycle of C5-C60 or the five-ring heterocycles of C4-C60, X is the aryl amine of C6-C30 or the condensed hetero ring of C6-C30.
2. a kind of 2,6- diphenyl naphthalene derivatives according to claim 1, which is characterized in that Ar be C6-C30 aryl, Thick aryl, the hexa-member heterocycle of C5-C30 or the five-ring heterocycles of C4-C30 of C10-C30.
3. a kind of 2,6- diphenyl naphthalene derivatives according to claim 1, which is characterized in that Ar be C6-C30 aryl, The thick aryl of C10-C30 or the five-ring heterocycles of C4-C30.
4. a kind of 2,6- diphenyl naphthalene derivatives according to claim 1, which is characterized in that X is the aryl amine of C12-C24 Or the condensed hetero ring of C12-C24.
5. according to claim 1-4 any one of them one kind 2,6- diphenyl naphthalene derivatives, which is characterized in that described 2,6- Diphenyl naphthalene derivatives are any one in compound TM1~TM32：
6. claim 1-5 any one of them 2, the preparation method of 6- diphenyl naphthalene derivatives, which is characterized in that including：
Intermediate shown in formula (A) and formula (B) compound represented are obtained into formula (I) institute by coupling reaction under nitrogen protection The 2,6- diphenyl naphthalene derivatives shown：
Wherein, Ar be the aryl of C6-C60, the thick aryl of C10-C60, the hexa-member heterocycle of C5-C60 or the five-ring heterocycles of C4-C60, X is the aryl amine of C6-C30 or the condensed hetero ring of C6-C30.
7. application of the 2,6- diphenyl naphthalene derivatives in organic electroluminescence device described in claim 1-5 any one.
8. application of 2, the 6- diphenyl naphthalene derivatives according to claim 7 in organic electroluminescence device, feature It is, the organic electroluminescence device includes anode, cathode, organic matter layer and light removing layer, and organic matter layer is noted comprising hole Enter at least one in layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer Layer；Contain claim 1-5 any one of them 2,6- diphenyl naphthalene derivatives in the smooth removing layer.
9. application of 2, the 6- diphenyl naphthalene derivatives according to claim 8 in organic electroluminescence device, feature It is, simultaneously containing Claims 1 to 5 any one of them 2,6- diphenyl naphthalene derives for the smooth removing layer and hole transmission layer Object.
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