CN107325007A - A kind of aromatic amine analog derivative and its preparation method and application - Google Patents

A kind of aromatic amine analog derivative and its preparation method and application Download PDF

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CN107325007A
CN107325007A CN201710505301.3A CN201710505301A CN107325007A CN 107325007 A CN107325007 A CN 107325007A CN 201710505301 A CN201710505301 A CN 201710505301A CN 107325007 A CN107325007 A CN 107325007A
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substituted
unsubstituted
aromatic amine
analog derivative
ring
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刘喜庆
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The present invention provides a kind of aromatic amine analog derivative and its preparation method and application, is related to organic optoelectronic materials technology.By structure optimization, improve the aromatic amine analog derivative thermal stability obtained by the present invention.For preparing organic electroluminescence device, especially as the hole mobile material in organic electroluminescence device, the features such as possessing high brightness, outstanding heat resistance, long-life and high efficiency.The present invention also provides a kind of preparation method of aromatic amine analog derivative, and the preparation method is simple, raw material is easy to get.

Description

A kind of aromatic amine analog derivative and its preparation method and application
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to a kind of aromatic amine analog derivative and its preparation side Method and application.
Background technology
Early in the 1960s, Pope et al. has found that the electro optical phenomenon of organic semiconducting materials, but because It was that, as luminescent layer, the device drive voltage of preparation is high, and luminosity is low, and the weight of people is not caused at that time using monocrystalline anthracene Depending on.Until in the 1980s, Tang and VanSlyke etc. is low using have developed for Organic micromolecular semiconductor material initiative The ultra-thin multilayer electroluminescent diode (Oganic Light Emitting Diodes, OLED) of voltage, high brightness.Before being based on The research of people, by in-depth study and develops first commercial produced based on OLED display product at the end of the nineties. Organic electroluminescence device due to energy-conservation, fast response time, colour stable, strong, radiationless environmental suitability, light weight, The features such as thickness of thin so that its application market is quite varied.
The principle of organic electroluminescent can simply be divided into 3 steps to illustrate, first, in the effect of applying bias Under, hole and electronics are overcome after the obstacle at interface, are injected by anode and negative electrode, the hole mobile material (HTL) into device HOMO can rank and electron transport material (ETL) LUMO can rank, then electric charge transmitted under extraneous electric field driven and reach luminous Layer, last electronics and hole are combined in luminescent layer organic substance, form exciton (exciton).Exciton is not one Stable state, is given off energy in the form of light or heat and returns to stable ground state, therefore be an electricity for entirety afterwards Flow the luminous phenomenon of driving.
With developing rapidly for photoelectric communication in recent years and MultiMedia Field, organic optoelectronic material turns into modern society The core of information and electronic industry.But, OLED will move towards practical, it is necessary to which solution reduces cost, improves luminous efficiency, extension The problems such as luminescent lifetime.
The content of the invention
It is an object of the invention to provide a kind of aromatic amine analog derivative and its preparation method and application, what the present invention was provided Organic compound thermal stability is high, preparation method is simple, the organic luminescent device being made up of the compound, shows luminous effect Rate is high, and the advantage of long lifespan is the luminous organic material of function admirable.
Present invention firstly provides a kind of aromatic amine analog derivative, structural formula is：
Wherein, Ar be selected from C6~C50 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substitution or In unsubstituted hexa-member heterocycle, C10~C30 substituted or unsubstituted condensed ring, C8~C30 substituted or unsubstituted condensed hetero ring One kind；R be selected from hydrogen atom, C6~C50 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substitution or In unsubstituted hexa-member heterocycle, C10~C30 substituted or unsubstituted condensed ring, C8~C30 substituted or unsubstituted condensed hetero ring One kind；X1~X8Respectively carbon atom or nitrogen-atoms.
It is preferred that, the Ar be selected from C6~C30 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, One kind in substituted or unsubstituted hexa-member heterocycle, C10~C30 substituted or unsubstituted condensed ring；R be selected from hydrogen atom, C6~ C50 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substituted or unsubstituted hexa-member heterocycle, C10~ One kind in C30 substituted or unsubstituted condensed ring；X2、X3、X6And X7It is carbon atom, and X1、X4、X5And X8In at least one For nitrogen-atoms.
It is preferred that, the Ar is C6~C10 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, taken Generation or unsubstituted hexa-member heterocycle,；R is hydrogen atom, C6~C10 substituted or unsubstituted aryl, substituted or unsubstituted five Circle heterocycles, substituted or unsubstituted hexa-member heterocycle；X2、X3、X6And X7It is carbon atom, and X1With X5It is nitrogen-atoms or X4With X8 It is nitrogen-atoms.
It is preferred that, any one of the aromatic amine analog derivative in structure shown in following TM1~TM65：
The present invention also provides a kind of preparation method of aromatic amine analog derivative, and syntheti c route is as follows：
Wherein, Ar be selected from C6~C50 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substitution or In unsubstituted hexa-member heterocycle, C10~C30 substituted or unsubstituted condensed ring, C8~C30 substituted or unsubstituted condensed hetero ring One kind；R be selected from hydrogen atom, C6~C50 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substitution or In unsubstituted hexa-member heterocycle, C10~C30 substituted or unsubstituted condensed ring, C8~C30 substituted or unsubstituted condensed hetero ring One kind；X1~X8Respectively carbon atom or nitrogen-atoms.
The present invention also provides application of the aromatic amine analog derivative in organic electroluminescence device.
It is preferred that, the organic electroluminescence device includes containing in anode, negative electrode and organic matter layer, the organic matter layer Described aromatic amine analog derivative.
It is preferred that, the aromatic amine analog derivative is used for the hole transmission layer for preparing organic electroluminescence device.
Beneficial effects of the present invention:
Present invention firstly provides a kind of aromatic amine analog derivative, the aromatic amine analog derivative has structure shown in formula I, By introducing pyrido [3,2-g] quinoline structure, rise electronics degree of excursion, and this novel heterocyclic compound diffraction is prepared into Device, as the hole mobile material in organic electroluminescence device, shows luminous efficiency height, the advantage of long lifespan, is better than Existing conventional OLED.The present invention also provides a kind of preparation method of aromatic amine analog derivative, and the preparation method is simple, former Material is easy to get, the need for disclosure satisfy that industrialization development.Aromatic amine analog derivative of the present invention has good in OLED luminescent devices Good application effect, with good industrialization prospect.
Embodiment
The technical scheme in the embodiment of the present invention will be clearly and completely described below, it is clear that described implementation Example 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 that the present invention is protected Enclose.
Present invention firstly provides a kind of aromatic amine analog derivative, structural formula is：
Wherein, Ar be selected from C6~C50 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substitution or In unsubstituted hexa-member heterocycle, C10~C30 substituted or unsubstituted condensed ring, C8~C30 substituted or unsubstituted condensed hetero ring One kind；R be selected from hydrogen atom, C6~C50 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substitution or In unsubstituted hexa-member heterocycle, C10~C30 substituted or unsubstituted condensed ring, C8~C30 substituted or unsubstituted condensed hetero ring One kind；X1~X8Respectively carbon atom or nitrogen-atoms.
Preferably Ar be selected from C6~C30 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substitution or One kind in unsubstituted hexa-member heterocycle, C10~C30 substituted or unsubstituted condensed ring；R is selected from hydrogen atom, C6~C50 and taken Generation or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substituted or unsubstituted hexa-member heterocycle, C10~C30 substitution Or one kind in unsubstituted condensed ring；X2、X3、X6And X7It is carbon atom, and X1、X4、X5And X8In at least one be nitrogen-atoms.
Further preferably Ar be C6~C10 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substitution or not Substituted hexa-member heterocycle,；R be hydrogen atom, C6~C10 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, Substituted or unsubstituted hexa-member heterocycle；X2、X3、X6And X7It is carbon atom, and X1With X5It is nitrogen-atoms or X4With X8It is that nitrogen is former Son.
According to the present invention, described substituted aryl, the five-ring heterocycles of substitution, the hexa-member heterocycle of substitution, the condensed ring of substitution, In substituted condensed hetero ring, substituent independence be selected from alkyl, alkoxy, amino, halogen, cyano group, nitro, hydroxyl or sulfydryl.
Specifically, the aromatic amine analog derivative is preferably selected from any one in structure shown in following TM1~TM65：
The present invention also provides a kind of preparation method of aromatic amine analog derivative, and syntheti c route is as follows：
Wherein, Ar be selected from C6~C50 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substitution or In unsubstituted hexa-member heterocycle, C10~C30 substituted or unsubstituted condensed ring, C8~C30 substituted or unsubstituted condensed hetero ring One kind；R be selected from hydrogen atom, C6~C50 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substitution or In unsubstituted hexa-member heterocycle, C10~C30 substituted or unsubstituted condensed ring, C8~C30 substituted or unsubstituted condensed hetero ring One kind；X1~X8Respectively carbon atom or nitrogen-atoms.
According to the present invention, the compound shown in intermediate A is prepared according to method as follows：
Substrate departs from via coupling reaction, methoxyl group and the displacement reaction of ketone group obtains intermediate A.Under nitrogen protection, Tetra-triphenylphosphine palladium is catalyst, and in the case that potassium carbonate is alkali, intermediate A is obtained with boronic acid compounds through Suzuki coupling reactions To intermediate B.
According to the present invention, the compound shown in target product is prepared according to method as follows：
Under nitrogen protection, triphenylphosphine palladium is catalyst, in the case that potassium carbonate is alkali, intermediate B and primary amine chemical combination Thing obtains target product via Buchwald-Hartwig coupling reactions.
According to the present invention, compound and synthesis target product shown in synthetic intermediate B are to pass through under nitrogen protection Coupling reaction is obtained, and the present invention does not have special limitation to the coupling reaction, using idol well-known to those skilled in the art Connection reaction, the preparation method is simple, and raw material is easy to get.
The present invention also provides application of the aromatic amine analog derivative in organic electroluminescence device, virtue of the invention Fragrant race's amine derivant can be applied as hole mobile material in terms of organic electroluminescence device, the organic electroluminescence Luminescent device include anode, negative electrode and organic matter layer, organic matter layer comprising hole injection layer, hole transmission layer, electronic barrier layer, At least one layer in luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer；At least one layer in the organic matter layer Contain aromatic amine analog derivative described above.The aromatic amine analog derivative can specifically be sent out as organic electroluminescence is prepared The hole transmission layer of optical device.The device architecture of use is preferably specially：BH1 and BD1 is used as luminescent layer material, and Alq3 is used as electricity Sub- transport materials, described aromatic amine analog derivative is used as hole transmission layer material, to manufacture construction same as below Organic luminescent device：Aromatic amine analog derivative/BH1 described in ITO/:BD1/Alq3/LiF/Al.The organic electroluminescent Device can be used for the application fields such as flat-panel monitor, lighting source, direction board, signal lamp.
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 A：The synthesis of intermediate A
The preparation of intermediate A
3- pyridine boronic acids (0.1mol) are dissolved in 300mL absolute ethers, -78 DEG C of the dry ice bath, in the condition of starvation Under, 44mL butyl lithium (2.5M) is added, stirring reaction 1 hour adds the bromo- pyridine carboxylic acid methyl esters (0.1mol) of 2-, reaction 2 Hour, after be gradually raised to 15~25 DEG C, add water terminating reaction.A point liquid, branch vibration layer, water layer acetic acid are carried out to reaction product Ethyl ester is extracted, and is merged organic phase, is spin-dried for organic solvent, white solid A-1 (yield 51%) is obtained by silica gel column chromatography.
A-1 (41.5mmol) is dissolved in 300mL tetrahydrofuran, 0 DEG C is cooled to, mixed liquor LTMP (LTMP are added As 500mL tetrahydrofuran dissolves 0.13mol butyl lithiums and 0.14mol 2,2,6,6- tetramethyl piperidines at 0 DEG C) after Stirring reaction 2 hours at 0 DEG C.200mL water terminating reactions are added, organic layer is spin-dried for by branch vibration layer, and column chromatography obtains solid A-2 (yield 54%).
Accurately weigh A-2 (10g, 47.8mmol) to be added in reaction bulb, add 200mL acetonitriles, then weigh 30g trichlorine oxygen Phosphorus is slowly dropped in reaction bulb, and slow after completion of dropping to be warming up to 60 DEG C, the reaction time is 5 hours.After completion of the reaction, add Water carefully go out by extraction, then places substantial amounts of saturated solution of sodium carbonate tune pH value to 7-8, adds dichloromethane, extracts three times, be spin-dried for It is intermediate A (7.5g, yield 63%) to obtain solid.
Mass spectrum m/z：247.97 (calculated values：247.99).Theoretical elemental content (%) C12H6Cl2N2：C,57.86；H, 2.43；Br,28.47；N, 11.25 actual measurement constituent contents (%)：C,57.85；H,2.43；Br,28.48；N,11.24.Above-mentioned knot Fruit confirms that it is target product to obtain product.
Embodiment B：The synthesis of intermediate B
(B1) preparation of intermediate B 1
Tetra-triphenylphosphine palladium (2.1g, 1.83mmol) and potassium carbonate (75.7g, 549mmol) are added to phenyl boric acid The solution of (22.3g, 183mmol) and intermediate A (45.8g, 185mmol) in degassing tetrahydrofuran (500mL), and should Mixture is heated 4 hours under reflux.The reactant mixture is cooled to room temperature, rotation afterwards removes solvent.Via silica gel column chromatography Obtain intermediate B 1 (49.5g, theoretical value 70%).
Mass spectrum m/z：290.05 (calculated values：290.06).Theoretical elemental content (%) C18H11ClN2：C,74.36；H, 3.81；Cl,12.19；N, 9.63 actual measurement constituent contents (%)：C,74.36；H,3.81；Cl,12.17；N,9.65.The above results Confirm that it is target product to obtain product.
(B2) preparation of intermediate B 2
Phenyl boric acid in embodiment B1 is replaced with into equimolar 1- naphthalene boronic acids, other steps are identical with embodiment B1, Obtain intermediate B 2.Mass spectrum m/z：340.05 (calculated values：340.08).Theoretical elemental content (%) C22H13ClN2：C,77.53； H,3.84；Cl,10.40；N, 8.22 actual measurement constituent contents (%)：C,77.51；H,3.85；Cl,10.41；N,8.23.Above-mentioned knot Fruit confirms that it is target product to obtain product.
(B3) preparation of intermediate B 3
Phenyl boric acid in embodiment B1 is replaced with into equimolar 2- naphthalene boronic acids, other steps are identical with embodiment B1, Obtain intermediate B 3.Mass spectrum m/z：340.06 (calculated values：340.08).Theoretical elemental content (%) C22H13ClN2：C,77.53； H,3.84；Cl,10.40；N, 8.22 actual measurement constituent contents (%)：C,77.52；H,3.85；Cl,10.42；N,8.21.Above-mentioned knot Fruit confirms that it is target product to obtain product.
(B4) preparation of intermediate B 4
Phenyl boric acid in embodiment B1 is replaced with it is equimolar to tert-butylbenzeneboronic acid, other steps with embodiment B1 It is identical, obtain intermediate B 4.Mass spectrum m/z：346.13 (calculated values：346.12).Theoretical elemental content (%) C22H19ClN2：C, 76.18；H,5.52；Cl,10.22；N, 8.08 actual measurement constituent contents (%)：C,76.19；H,5.52；Cl,10.22；N,8.07. The above results confirm that it is target product to obtain product.
(B5) preparation of intermediate B 5
Phenyl boric acid in embodiment B1 is replaced with into equimolar 4- pyridine boronic acids, other steps with embodiment B1 phases Together, intermediate B 5 is obtained.Mass spectrum m/z：291.05 (calculated values：291.06).Theoretical elemental content (%) C17H10ClN3：C, 69.99；H,3.45；Cl,12.15；N, 14.40 actual measurement constituent contents (%)：C,69.97；H,3.46；Cl,12.15；N, 14.42.The above results confirm that it is target product to obtain product.
Embodiment C：The synthesis of target product
(C1) compound TM1 preparation
By tri-butyl phosphine (3mL 1.0M toluene solution, 7.32mmol), palladium (0.4g, 1.83mmol) and uncle Sodium butoxide (37.0g, 402mmol) is added to 9- bromines anthracene (98.3g, 384mmol) and aniline (17.0g, 183mmol) in degassing first Solution in benzene (500mL), and the mixture is heated 2 hours under reflux.The reactant mixture is cooled to room temperature, used Dilution with toluene and filtered via diatomite.The filtrate water is diluted, and extracted with toluene, and merges organic phase, by it It is evaporated under vacuo.The residue is filtered via silica gel, target product TM1 (65.1g, yield is recrystallized to give For 80%).
Mass spectrum m/z：445.19 (calculated values：445.18).Theoretical elemental content (%) C34H23N：C,91.65；H,5.20； N, 3.14 actual measurement constituent contents (%)：C,91.66；H,5.21；N,3.13.The above results confirm that it is target product to obtain product.
(C2) compound TM4 synthesis：
Aniline in embodiment C1 is replaced with into equimolar 4-aminopyridine, other steps are identical with embodiment C1, Obtain target product TM4.Mass spectrum m/z：446.15 (calculated values：446.18).Theoretical elemental content (%) C33H22N2：C,88.76； H,4.97；N, 6.27 actual measurement constituent contents (%)：C,88.75；H,4.98；N,6.27.The above results confirm that it is mesh to obtain product Mark product.
(C3) compound TM9 synthesis：
By tri-butyl phosphine (3mL 1.0M toluene solution, 7.32mmol), palladium (0.4g, 1.83mmol) and uncle Sodium butoxide (37.0g, 402mmol) added to 10- chlorobenzenes simultaneously [g] quinoline (81.8g, 384mmol) and aniline (17.0g, 183mmol) the solution in degassed toluene (500mL), and the mixture is heated 2 hours under reflux.The reaction is mixed Compound is cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and extracted with toluene, and And merge organic phase, it is evaporated under vacuo.The residue is filtered via silica gel, target production is recrystallized to give (76%) 62.1g, yield is to thing TM1.
Mass spectrum m/z：447.15 (calculated values：447.17).Theoretical elemental content (%) C32H21N3：C,85.88；H,4.73； N, 9.39 actual measurement constituent contents (%)：C,87.89；H,4.74；N,9.37.The above results confirm that it is target product to obtain product.
(C4) compound TM13 synthesis：
Aniline in embodiment C3 is replaced with into equimolar 4-aminopyridine, other steps are identical with embodiment C3, Obtain target product TM13.Mass spectrum m/z：448.15 (calculated values：448.17).Theoretical elemental content (%) C31H20N4：C, 83.01；H,4.49；N, 12.49 actual measurement constituent contents (%)：C,83.02；H,4.48；N,12.49.The above results confirm to obtain Product is target product.
(C5) compound TM21 synthesis：
By tri-butyl phosphine (3mL 1.0M toluene solution, 7.32mmol), palladium (0.4g, 1.83mmol) and uncle Sodium butoxide (37.0g, 402mmol) is added to intermediate B 1 (111.3g, 384mmol) and aniline (17.0g, 183mmol) de- Solution in gas toluene (500mL), and the mixture is heated 2 hours under reflux.The reactant mixture is cooled to room Temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and extracted with toluene, and merges organic phase, It is evaporated under vacuo.The residue is filtered via silica gel, be recrystallized to give target product TM21 (79.1g, 72%) yield is.
Mass spectrum m/z：601.25 (calculated values：601.23).Theoretical elemental content (%) C42H27N5：C,83.84；H,4.52； N, 11.64 actual measurement constituent contents (%)：C,83.85；H,4.52；N,11.63.The above results confirm that obtain product produces for target Product.
(C6) compound TM25 synthesis
Aniline in embodiment C5 is replaced with into equimolar 4-aminopyridine, other steps are identical with embodiment C5, Obtain target product TM25.Mass spectrum m/z：602.25 (calculated values：602.22).Theoretical elemental content (%) C41H26N6：C, 81.71；H,4.35；N, 13.94 actual measurement constituent contents (%)：C,81.72；H,4.35；N,13.93.The above results confirm to obtain Product is target product.
(C7) compound TM30 synthesis
Intermediate B 1 in embodiment C5 is replaced with into equimolar intermediate B 2, other steps with embodiment C5 phases Together, target product TM30 is obtained.Mass spectrum m/z：701.25 (calculated values：701.26).Theoretical elemental content (%) C50H31N5：C, 85.57；H,4.45；N, 9.98 actual measurement constituent contents (%)：C,85.58；H,4.43；N,9.99.The above results confirm to be produced Thing is target product.
(C8) compound TM34 synthesis
Intermediate B 1 in embodiment C5 is replaced with into equimolar intermediate B 2, aniline changes equimolar 4- amino pyrrole into Pyridine, other steps are identical with embodiment C5, obtain target product TM34.Mass spectrum m/z：702.26 (calculated values：702.25).Reason Argument cellulose content (%) C49H30N6：C,83.74；H,4.30；N, 11.96 actual measurement constituent contents (%)：C,83.75；H,4.31；N, 11.95.The above results confirm that it is target product to obtain product.
(C9) compound TM39 synthesis
Intermediate B 1 in embodiment C5 is replaced with into equimolar intermediate B 3, other steps with embodiment C5 phases Together, target product TM39 is obtained.Mass spectrum m/z：701.25 (calculated values：701.26).Theoretical elemental content (%) C50H31N5：C, 85.57；H,4.45；N, 9.98 actual measurement constituent contents (%)：C,85.56；H,4.45；N,9.99.The above results confirm to be produced Thing is target product.
(C10) compound TM43 synthesis
Intermediate B 1 in embodiment C5 is replaced with into equimolar intermediate B 3, aniline changes equimolar 4- amino pyrrole into Pyridine, other steps are identical with embodiment C5, obtain target product TM43.Mass spectrum m/z：702.25 (calculated values：702.25).Reason Argument cellulose content (%) C49H30N6：C,83.74；H,4.30；N, 11.96 actual measurement constituent contents (%)：C,83.73；H,4.31；N, 11.96.The above results confirm that it is target product to obtain product.
(C11) compound TM48 synthesis
Intermediate B 1 in embodiment C5 is replaced with into equimolar intermediate B 4, other steps with embodiment C5 phases Together, target product TM48 is obtained.Mass spectrum m/z：713.34 (calculated values：713.35).Theoretical elemental content (%) C50H43N5：C, 84.12；H,6.07；N, 9.81 actual measurement constituent contents (%)：C,84.13；H,6.05；N,9.82.The above results confirm to be produced Thing is target product.
(C12) compound TM52 synthesis
Intermediate B 1 in embodiment C5 is replaced with into equimolar intermediate B 4, aniline changes equimolar 4- amino pyrrole into Pyridine, other steps are identical with embodiment C5, obtain target product TM52.Mass spectrum m/z：714.32 (calculated values：714.35).Reason Argument cellulose content (%) C49H42N6：C,82.32；H,5.92；N, 11.76 actual measurement constituent contents (%)：C,82.33；H,5.92；N, 11.75.The above results confirm that it is target product to obtain product.
(C13) compound TM52 synthesis
Intermediate B 1 in embodiment C5 is replaced with into equimolar intermediate B 5, other steps with embodiment C5 phases Together, target product TM57 is obtained.Mass spectrum m/z：603.24 (calculated values：603.22).Theoretical elemental content (%) C40H25N7：C, 79.58；H,4.17；N, 16.24 actual measurement constituent contents (%)：C,79.58；H,4.16；N,16.26.The above results confirm to obtain Product is target product.
(C14) compound TM61 synthesis
Intermediate B 1 in embodiment C5 is replaced with into equimolar intermediate B 5, aniline changes equimolar 4- amino pyrrole into Pyridine, other steps are identical with embodiment C5, obtain target product TM61.Mass spectrum m/z：604.22 (calculated values：604.21).Reason Argument cellulose content (%) C39H24N8：C,77.47；H,4.00；N, 18.53 actual measurement constituent contents (%)：C,77.46；H,4.01；N, 18.53.The above results confirm that it is target product to obtain product
Contrast Application Example：
Transparent anode electrode ito substrate is cleaned by ultrasonic 15 minutes in isopropanol, and exposed 30 minutes under ultraviolet light, Then handled 10 minutes with plasma.The ito substrate after processing is then put into evaporated device.One layer of 30nm's of evaporation first NPB is as hole transmission layer, followed by the evaporation of luminescent layer, mixing evaporation BH1 and 5% BD1, then evaporation 30nm Alq3 As electron transfer layer, 0.5nm LiF are then deposited again, then evaporation 60nm metal Al.
Application Example
Transparent anode electrode ito substrate is cleaned by ultrasonic 15 minutes in isopropanol, and exposed 30 minutes under ultraviolet light, Then handled 10 minutes with plasma.The ito substrate after processing is then put into evaporated device.One layer of 30nm reality is deposited first The compound TM of C synthesis is applied as hole transmission layer, followed by the evaporation of luminescent layer, mixing evaporation BH1 and 5% BD1, with 0.5nm LiF are then deposited as electron transfer layer in evaporation 30nm Alq3 again afterwards, then evaporation 60nm metal Al.
The electron luminescence characteristic of the organic luminescent device of above method manufacture is represented in the following table：
Result above shows that aromatic amine analog derivative of the invention is applied in organic electroluminescence device, especially As hole mobile material, luminous efficiency height, the advantage of long lifespan are shown, is luminous organic material of good performance.
Obviously, the explanation of above example is only intended to the method and its core concept for helping to understand the present invention.It should refer to Go out, under the premise without departing from the principles of the invention, can also be to this hair for the those of ordinary skill of the technical field Bright to carry out some improvement and modification, these are improved and modification is also fallen into the protection domain of the claims in the present invention.

Claims (8)

1. a kind of aromatic amine analog derivative, it is characterised in that structural formula is as shown in formula I：
Wherein, Ar is selected from C6~C50 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substitution or not taken One in the hexa-member heterocycle in generation, C10~C30 substituted or unsubstituted condensed ring, C8~C30 substituted or unsubstituted condensed hetero ring Kind；R is selected from hydrogen atom, C6~C50 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substitution or not taken One in the hexa-member heterocycle in generation, C10~C30 substituted or unsubstituted condensed ring, C8~C30 substituted or unsubstituted condensed hetero ring Kind；X1~X8Respectively carbon atom or nitrogen-atoms.
2. a kind of aromatic amine analog derivative according to claim 1, it is characterised in that Ar is selected from C6~C30 substitution Or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substituted or unsubstituted hexa-member heterocycle, C10~C30 substitution or One kind in unsubstituted condensed ring；R is selected from hydrogen atom, C6~C50 substituted or unsubstituted aryl, substituted or unsubstituted five One kind in circle heterocycles, substituted or unsubstituted hexa-member heterocycle, C10~C30 substituted or unsubstituted condensed ring；X2、X3、X6With X7It is carbon atom, and X1、X4、X5And X8In at least one be nitrogen-atoms.
3. a kind of aromatic amine analog derivative according to claim 1, it is characterised in that Ar for C6~C10 substitution or Unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substituted or unsubstituted hexa-member heterocycle,；R is hydrogen atom, C6~C10 Substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substituted or unsubstituted hexa-member heterocycle；X2、X3、X6With X7It is carbon atom, and X1With X5It is nitrogen-atoms or X4With X8It is nitrogen-atoms.
4. a kind of aromatic amine analog derivative according to claim 1, it is characterised in that the aromatic amine analog derivative Any one in structure shown in following TM1~TM65：
5. the preparation method of the aromatic amine analog derivative described in claim any one of 1-4, it is characterised in that pass through following road Line synthesis obtains the analog derivative containing aromatic amine：
Wherein, Ar is selected from C6~C50 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substitution or not taken One in the hexa-member heterocycle in generation, C10~C30 substituted or unsubstituted condensed ring, C8~C30 substituted or unsubstituted condensed hetero ring Kind；R is selected from hydrogen atom, C6~C50 substituted or unsubstituted aryl, substituted or unsubstituted five-ring heterocycles, substitution or not taken One in the hexa-member heterocycle in generation, C10~C30 substituted or unsubstituted condensed ring, C8~C30 substituted or unsubstituted condensed hetero ring Kind；X1~X8Respectively carbon atom or nitrogen-atoms.
6. application of the aromatic amine analog derivative described in claim 1-4 any one in organic electroluminescence device.
7. application of the aromatic amine analog derivative according to claim 6 in organic electroluminescence device, its feature exists In the organic electroluminescence device includes containing Claims 1 to 4 in anode, negative electrode and organic matter layer, the organic matter layer Aromatic amine analog derivative described in any one.
8. application of the aromatic amine analog derivative according to claim 7 in organic electroluminescence device, its feature exists In the organic layer includes containing the aromatic amine described in any one of Claims 1 to 4 in hole transmission layer, hole transmission layer Analog derivative.
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Application publication date: 20171107