CN108129333A - A kind of 4 luxuriant and rich with fragrance substitutive derivatives and its application - Google Patents

A kind of 4 luxuriant and rich with fragrance substitutive derivatives and its application Download PDF

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CN108129333A
CN108129333A CN201611090887.3A CN201611090887A CN108129333A CN 108129333 A CN108129333 A CN 108129333A CN 201611090887 A CN201611090887 A CN 201611090887A CN 108129333 A CN108129333 A CN 108129333A
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substituted
phenanthryl
condensed
heteroaryl
group
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CN108129333B (en
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范洪涛
李之洋
张伟
张向慧
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Beijing Eternal Material Technology Co Ltd
Guan Eternal Material Technology Co Ltd
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Beijing Eternal Material Technology Co Ltd
Guan Eternal Material Technology Co Ltd
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Abstract

The present invention provides a kind of general formula compound as shown in following formula I：Ar is selected from C6~C50Substituted or non-substituted aryl, C6~C50Substituted or non-substituted condensed-nuclei aromatics group, C4~C50Substituted or non-substituted heteroaryl, C4~C50Substituted or non-substituted condensed hetero ring aromatic hydrocarbon group；Above-mentioned heteroaryl and condensed hetero ring aromatic hydrocarbon group are selected from B, N, O, S, P (=O), the hetero atom of Si and P and with the monocyclic or fused ring aryl of 4~50 ring carbon atoms comprising one or more；N is 1 or 2；As n=2, L is selected from structure shown in following formula A, B, C or D：As n=1, L is selected from structure shown in following formula E or F：

Description

A kind of 4 luxuriant and rich with fragrance substitutive derivatives and its application
Technical field
The present invention relates to a kind of novel organic compound more particularly to a kind of virtues that can be used for organic electroluminescence device Fragrant race's amine derivative also relates to a kind of organic electroluminescence device using the aromatic amine derivative.
Background technology
Display of organic electroluminescence (hereinafter referred to as OLED) has from main light emission, low-voltage direct-current driving, all solidstate, regards Angular width, light-weight, composition and a series of advantage such as simple for process, compared with liquid crystal display, display of organic electroluminescence Backlight is not needed to, visual angle is big, and power is low, and up to 1000 times of liquid crystal display, manufacture cost is but less than response speed The liquid crystal display of equal resolution ratio, therefore, organic electroluminescence device has broad application prospects.
The organic electroluminescence device (OLED) of electroluminescent organic material has been used, can be used for the complete of solid luminescence type The fields such as color displays and solid-state white illumination, are known as next-generation novel display and lighting engineering.Usual OLED device contains There is luminescent layer and clamp a pair of of opposite electrode of this layer.When device applies electric field between two electrodes, electronics is injected from cathode side, from Anode-side injects hole, and electronics, with hole-recombination, forms excited state, when excited state is restored to ground state, energy in luminescent layer Amount is released in the form of light.
OLED is shown and is illuminated, blue light material is always a bottleneck for the development of OLED, and one side blue light is On the other hand indispensable component part in display and lighting engineering it is not high also to receive conventional fluorescent material efficiency, blue Phosphor material is although efficient, but stability is poor, while also lacks dark blue luminescent material system.Fluorescence blue light material has very Good stability and quantity is more, and the emerging production of light extraction protects a series of blue light dyestuffs using pyrene as precursor structure, as shown below Blue light material, the CIE coordinates of the device as blue light material are (0.14,0.25), are the pretty good day blue light dyes of a performance Material.But dark blue luminescent material, for reducing display and the energy expenditure of illuminating device, the overall effect for enhancing device has very Important role, and efficient dark blue luminescent material is relatively fewer.Therefore it is significant to develop such material.
As the example of the blue fluorescent material used in luminescent layer, in patent document CN201080003398.4, The blue emitting material with dibenzofurans substituent group is disclosed in US2014326985 (A1), short wavelength can be obtained Blue-light-emitting, but luminous efficiency is low, still needs to further improve.
Although can confirm the improvement of the characteristics of luminescence in any materials and arbitrary combination, all it is not enough, urgently It needs to develop a kind of performance high-luminous-efficiency, realize the luminescent material that shorter wavelength shines.
Invention content
The object of the present invention is to provide one kind can obtain the high deep blue light emitting material of excitation purity with high-luminous-efficiency Material and application long-life of such material, high-luminous-efficiency, high color purity OLED device.
According to the present invention, following a kind of new aromatic amine derivative, organic electroluminescence device are provided.
The general formula compound design of the present invention is used with the 4- luxuriant and rich with fragrance compounds for structural unit of substitution, the advantages of protrusion It is：Since luxuriant and rich with fragrance 4- positions substitution has very big steric hindrance, with the obtained aromatic amine one side energy of suitable polycyclic aromatic hydrocarbon The blue light of short wavelength's transmitting is enough obtained, still further aspect can significantly increase material fluorescence radiation efficiency.
Aromatic amine derivative provided by the invention, shown in general structure such as following formula (I).
Wherein, Ar is selected from C6~C50Substituted or non-substituted aryl, C6~C50Substituted or non-substituted condensed-nuclei aromatics Group, C4~C50Substituted or non-substituted heteroaryl, C4~C50Substituted or non-substituted condensed hetero ring aromatic hydrocarbon group.
Specifically, in above-mentioned logical formula (I), C that Ar is selected from6~C50Substituted or unsubstituted aryl refer to 6 to 50 The aromatics ring system of ring skeleton carbon atom including single ring architecture substituent group such as phenyl, also includes being covalently attached the virtue of structure Ring substitute group is such as xenyl, terphenyl.
Specifically, in above-mentioned logical formula (I), C that Ar is selected from6~C50Substituted or unsubstituted condensed-nuclei aromatics refer to 10 to The aromatics ring system of 50 ring skeleton carbon atoms, including condensed cyclic structure substituent group such as naphthalene, anthryl, also including condensed cyclic structure Substituent group such as benzene binaphthyl, naphthalene xenyl, biphenyl dianthranide base, is also wrapped with the building stone that single ring architecture aryl is connected The thick aromatic ring substituents group for being covalently attached structure is included such as binaphthyl.
Specifically, in above-mentioned logical formula (I), heteroaryl and condensed hetero ring aromatic hydrocarbon group that Ar is selected from refer to comprising one or more choosings From the hetero atom of B, N, O, S, P (=O), Si and P and with the monocyclic or fused ring aryl of 4~50 ring carbon atoms.
Specifically, when the Ar be selected from substitution aryl, substitution condensed-nuclei aromatics group, substitution heteroaryl when or substitution Condensed hetero ring aromatic hydrocarbon group when, the substituent group be selected from C1~C12Straight chained alkyl, branched alkyl or cycloalkyl.
In the general formula of the present invention, n is selected from 1 or 2：
As n=2, the L led in formula (I) is selected from structure shown in following formula A, B, C or D：
As n=1, the L led in formula (I) is selected from structure shown in following formula E or F：
Further, in above-mentioned logical formula (I), preferably Ar is selected from C6~C24Substituted or non-substituted aryl, C6~C24Substitution Or non-substituted condensed-nuclei aromatics group, C4~C30Substituted or non-substituted heteroaryl, C4~C30It is substituted or non-substituted thick Ring heteroaryl hydrocarbyl group.
Further, it is above-mentioned when Ar be selected from heteroaryl or condensed ring heteroaryl hydrocarbyl group when, the hetero atom be preferably O, S or N。
In above-mentioned logical formula (I), more preferably Ar is selected from C6~C24Substituted or non-substituted aryl, C6~C24Substitution non-takes The condensed-nuclei aromatics group in generation
Further, in above-mentioned logical formula (I), the Ar is preferably phenyl, aminomethyl phenyl, phenanthryl, xenyl, dibenzo Thienyl, naphthalene and phenanthryl, quinolyl, pyridyl group and preferably anthryl, terphenyl, fluorenyl, furyl, thienyl, pyrrole Cough up base, benzofuranyl, benzothienyl, isobenzofuran-base, indyl, dibenzothiophene, 9- phenyl carbazoles, 9- naphthalenes Carbazole, benzo carbazole, dibenzo-carbazole, indolocarbazole, benzodioxole group etc..
Further, in logical formula (I) of the invention, the chemical combination that the compound of following concrete structures represents can preferably be gone out Object：A1-A15, B1-B4, C1-C4, D1-D2, E1-E4, F1-F10, these compounds are only representative.
The present invention also provides purposes of the above-mentioned compound selected from logical formula (I) in organic electroluminescence device is prepared.
The present invention also provides a kind of organic electroluminescence device, including being included at least between anode, cathode and two electrodes At least one layer in one layer containing luminescent layer and above organic function layer, the wherein organic function layer is individually or as mixing Ingredient contains the compound described in the logical formula (I) of the present invention.
Specifically, the compound in the logical formula (I) can be, but not limited in organic electroluminescence device as luminous The material of main part and fluorescence luminescent material of layer.
The compounds of this invention has the luxuriant and rich with fragrance structural unit that special 4- positions replace, this unit and some preferred condensed ring The aromatic amine compound that aromatic hydrocarbons is formed has the advantages that dark blue light can be emitted and with high fluorescence quantum efficiency, Neng Gouying In Nan dian Yao device, it is ensured that the CIE coordinate y values of device are less than 0.15, can be effectively reduced display and illumination Using upper power consumption.
Specific embodiment
In order to which those skilled in the art is made to more fully understand the present invention, this hair is described in detail below with reference to following embodiment The preparation method and hair of bright organic electroluminescent compounds and preparation method thereof and luminescent device comprising the compound Light property is described in further detail the present invention.
The compound for the synthetic method do not mentioned in embodiment is all the raw produce obtained by commercial sources
Main compound synthetic example
Synthesis example 1.
The synthesis of A1
Under argon gas stream, put into 250mL eggplant type flasks 1,6- dibromos pyrene (3.6g, 0.01mol), N- (4- phenanthryl)- Aniline (5.9g, 0.022mol), three (dibenzalacetone) two palladium (0) (Pd2 (dba) 3) 0.1g, 50% toluene of tri-tert-butylphosphine Solution 0.1ml, sodium tert-butoxide (2.9g, 0.03mol), dehydrated toluene 50mL, back flow reaction 3 hours.After cooling, with diatomite mistake Reaction solution is filtered, obtained crude product is obtained into off-white powder 5.3g, yield 72% with re crystallization from toluene.
Synthesis example 2
The synthesis of A2
Using method prepare compound A2 same as Example 1, difference is to replace with N- (4- phenanthryl)-aniline N- (4- phenanthryl) -2-aminotoluene of equivalent, after the completion of reaction, isolated white solid 5.5g, yield 73%.
1H NMR (500MHz, Chloroform) δ 8.98 (dd, J=14.1,3.8Hz, 2H), 8.65-8.52 (m, 2H), 8.00-7.84 (m, 8H), 7.77-7.53 (m, 12H), 7.24-7.08 (m, 6H), 6.90 (ddd, J=15.1,9.1,3.4Hz, 2H), 6.72 (d, J=15.0Hz, 2H), 2.13 (s, 6H)
Synthesis example 3
The synthesis of A3
Using method prepare compound A3 same as Example 1, difference is to replace with N- (4- phenanthryl)-aniline Equivalent N- (4- phenanthryl) -3- methylanilines, after the completion of reaction, isolated white solid 5.5g, yield 73%.
Synthesis example 4
The synthesis of A4
Using method prepare compound A4 same as Example 1, difference is to replace with N- (4- phenanthryl)-aniline Equivalent N- (4- phenanthryl) -4- methylanilines, after the completion of reaction, isolated white solid 5.5g, yield 73%.
Synthesis example 5
The synthesis of A5
Using method prepare compound A5 same as Example 1, difference is to replace with N- (4- phenanthryl)-aniline Equivalent N- (4- phenanthryl) -4- cyclohexyl aniline, after the completion of reaction, isolated white solid 6.8g, yield 75%.
Synthesis example 6
The synthesis of A6
Using method prepare compound A6 same as Example 1, difference is to replace with N- (4- phenanthryl)-aniline Equivalent N- (4- phenanthryl) -4- tertiary butyl aniline, after the completion of reaction, isolated white solid 6.3g, yield 74%.
Synthesis example 7
The synthesis of A7
Using method prepare compound A7 same as Example 1, difference is to replace with N- (4- phenanthryl)-aniline Equivalent N- (4- phenanthryl) -2- benzidine, after the completion of reaction, isolated white solid 6.4g, yield 72%.
1H NMR (500MHz, Chloroform) δ 8.98 (dd, J=14.1,3.8Hz, 2H), 8.19-8.03 (m, 2H), 8.02-7.82 (m, 8H), 7.81-7.51 (m, 12H), 7.50-7.30 (m, 12H), 7.22-6.99 (m, 6H), 6.39 (d, J= 14.8Hz,2H).
Synthesis example 8
The synthesis of A8
Using method prepare compound A8 same as Example 1, difference is to replace with N- (4- phenanthryl)-aniline Equivalent N- (4- phenanthryl) -3- benzidine, after the completion of reaction, isolated white solid 6.4g, yield 72%.
Synthesis example 9
The synthesis of A9
Using method prepare compound A9 same as Example 1, difference is to replace with N- (4- phenanthryl)-aniline Equivalent N- (4- phenanthryl)-naphthalidine, after the completion of reaction, isolated white solid 5.7g, yield 68%.
1H NMR(500MHz,Chloroform)δ8.98(s,2H),8.55(s,2H),8.22(s,2H),8.02–7.79 (m,10H),7.79–7.37(m,22H),6.95(s,2H).
Synthesis example 10
The synthesis of A10
Using method prepare compound A10 same as Example 1, difference is to replace with N- (4- phenanthryl)-aniline Equivalent N- (4- phenanthryl) -2- naphthylamines, after the completion of reaction, isolated white solid 5.7g, yield 68%.
Synthesis example 11
The synthesis of A11
Using method prepare compound A11 same as Example 1, difference is to replace with N- (4- phenanthryl)-aniline Equivalent N- (4- phenanthryl) -1- phenanthrene amine, after the completion of reaction, isolated white solid 6.1g, yield 65%.
Synthesis example 12
The synthesis of A12
Using method prepare compound A12 same as Example 1, difference is to replace with N- (4- phenanthryl)-aniline Equivalent N- (4- phenanthryl) -3- phenanthrene amine, after the completion of reaction, isolated white solid 6.1g, yield 65%.
Synthesis example 13
The synthesis of A13
Using method prepare compound A13 same as Example 1, difference is to replace with N- (4- phenanthryl)-aniline Equivalent N- (4- phenanthryl) -2- phenylpyridine -4- amine, after the completion of reaction, isolated white solid 6.0g, yield 67%.
1H NMR (500MHz, Chloroform) δ 8.98 (dd, J=14.1,3.8Hz, 2H), 8.42-8.24 (m, 6H), 8.02-7.84 (m, 8H), 7.81-7.35 (m, 22H), 6.70 (d, J=15.0Hz, 2H), 6.29 (dd, J=15.0,2.9Hz, 2H).
Synthesis example 14
The synthesis of A14
Using method prepare compound A14 same as Example 1, difference is to replace with N- (4- phenanthryl)-aniline Equivalent N- (4- phenanthryl)-quinoline -2- amine, after the completion of reaction, isolated white solid 5.8g, yield 69%.
Synthesis example 15
The synthesis of A15
Using method prepare compound A15 same as Example 1, difference is to replace with N- (4- phenanthryl)-aniline Equivalent N- (4- phenanthryl) base-fluorenes -2- amine, after the completion of reaction, isolated white solid 6.2g, yield 64%.
Synthesis example 16
The synthesis of B1
Under argon gas stream, 6,12- dibromos are put into 250mL eggplant type flasks(10g, 0.026mol), N- (4- phenanthryl)- 2,4- dimethylanilines (15.6g, 0.0546mol), three (dibenzalacetone) two palladium (0) (Pd2 (dba) 3) 0.26g, three uncles 50% toluene solution 0.5ml of butyl phosphine, sodium tert-butoxide (10.6g, 0.1112mol), dehydrated toluene 100mL, back flow reaction 3 are small When.After cooling, with diatomite filtering reacting solution, obtained crude product is obtained into off-white powder 6.5g, yield with re crystallization from toluene 79%.
1H NMR (500MHz, Chloroform) δ 8.98 (dd, J=14.2,3.7Hz, 4H), 8.15-8.00 (m, 4H), 7.96–7.85(m,4H),7.79–7.51(m,14H),7.11–7.00(m,4H),6.93–6.81(m,4H),2.24(s,6H), 2.13(s,6H).
Synthesis example 17
The synthesis of B2
Using the method prepare compound B2 identical with embodiment 17, difference is N- (4- phenanthryl) -2,4- dimethyl Aniline replaces with equivalent N- (4- phenanthryl) -2-aminotoluene, and after the completion of reaction, isolated white solid 6.2g, yield is 78%.
Synthesis example 18
The synthesis of B3
Using the method prepare compound B3 identical with embodiment 17, difference is N- (4- phenanthryl) -2,4- dimethyl Aniline replaces with equivalent N- (4- phenanthryl) -2- benzidine, and after the completion of reaction, isolated white solid 6.9g, yield is 75%.
Synthesis example 19
The synthesis of B4
Using the method prepare compound B4 identical with embodiment 17, difference is N- (4- phenanthryl) -2,4- dimethyl Aniline replaces with equivalent N- (4- phenanthryl)-naphthalidine, after the completion of reaction, isolated white solid 5.8g, and yield 68%.
Synthesis example 20
The synthesis of C1
2,8- dibromo, 6,6,12,12- tetramethyl -6,12- dihydro indeno [1,2-B] fluorenes (10g, 0.0214mol) and N- (4- Phenanthryl) -2,4- dimethylanilines (12.9,0.0449mol), three (dibenzalacetone) two palladium (0) (Pd2 (dba) 3) 0.26g, 50% toluene solution 0.5ml of tri-tert-butylphosphine, sodium tert-butoxide (10.6g, 0.1112mol), dehydrated toluene 100mL, back flow reaction 3 Hour.After cooling, with diatomite filtering reacting solution, obtained crude product is obtained into faint yellow color solid 5.6g with re crystallization from toluene, Yield 62%.
Synthesis example 21
The synthesis of C2
Using the method prepare compound C2 identical with synthesis example 21, difference is N- (4- phenanthryl) -2,4- dimethyl Aniline replaces with equivalent N- (4- phenanthryl)-aniline, and after the completion of reaction, isolated faint yellow color solid 5.7g, yield is 68%.
1H NMR (500MHz, Chloroform) δ 8.95 (dd, J=14.2,3.9Hz, 2H), 8.41-8.28 (m, 2H), 8.00 (d, J=15.0Hz, 2H), 7.93-7.78 (m, 6H), 7.76-7.47 (m, 10H), 7.38 (d, J=2.9Hz, 2H), 7.29-7.14 (m, 4H), 7.11-6.89 (m, 6H), 6.47 (dd, J=14.9,3.0Hz, 2H), 1.68 (s, 12H)
Synthesis example 22
The synthesis of C3
Using the method prepare compound C3 identical with synthesis example 21, difference is N- (4- phenanthryl) -2,4- dimethyl Aniline replaces with equivalent N- (4- phenanthryl) -3- benzidine, after the completion of reaction, isolated faint yellow color solid 7.1g, and yield It is 71%.
Synthesis example 23
The synthesis of C4
Using the method prepare compound C4 identical with synthesis example 21, difference is N- (4- phenanthryl) -2,4- dimethyl Aniline replaces with equivalent N- (4- phenanthryl)-naphthalidine, and after the completion of reaction, isolated faint yellow color solid 5.9g, yield is 62%.
Synthesis example 24
The synthesis of D1
5,11- dibromo, 7,7,13,13 tetramethyl 7,13- dihydrobenzos [g] indeno [1,2-B] fluorenes (10mmol, 5.18g) with N- (4- phenanthryl) -3- benzidine (22mmol, 7.4g), sodium tert-butoxide 5.7g, toluene 200mL lead to nitrogen under liquid level of solution 30min adds 0.4g Pd2 (dba) 3, injects 10% tri-tert-butylphosphine 10ml with syringe, opens stirring, be heated to 120 Degree Celsius, after reacting 4 hours, reaction solution washing, organic phase concentrates, and re crystallization from toluene obtains light yellow solid 6.4g, yield 61%.
Synthesis example 25
The synthesis of D2
Using the method prepare compound D2 identical with synthesis example 25, difference is to replace in N- (4- phenanthryl) -3- benzidine Equivalent N- (4- phenanthryl)-aniline is changed to, after the completion of reaction, isolated faint yellow solid 5.8g, yield 65%.
1H NMR (500MHz, Chloroform) δ 8.98 (dd, J=14.1,3.8Hz, 2H), 8.91-8.75 (m, 2H), 8.24–8.08(m,2H),7.98–7.83(m,4H),7.81–7.50(m,13H),7.41–7.17(m,8H),7.16–6.93(m, 7H),1.75(s,6H),1.69(s,6H).
Synthesis example 26
The synthesis of E1
1- bromines pyrene (10mmol, 2.8g) and N- (4- phenanthryl) aniline (22mmol, 5.7g), sodium tert-butoxide 5.7g, toluene 100mL leads to nitrogen 30min under liquid level of solution, adds 0.2g Pd2 (dba) 3, injects 10% tri-tert-butylphosphine with syringe 2ml opens stirring, is heated to 120 degrees Celsius, and after reacting 4 hours, reaction solution washing, organic phase concentration, re crystallization from toluene obtains shallow Yellow solid 3.5g, yield 75%.
1H NMR (500MHz, Chloroform) δ 8.98 (dd, J=14.1,3.8Hz, 1H), 8.39-8.24 (m, 1H), 8.17–7.97(m,6H),7.97–7.83(m,4H),7.79–7.49(m,6H),7.31–7.17(m,2H),7.13–6.93(m, 3H).
Synthesis example 27
The synthesis of E2
Using the method prepare compound E2 identical with synthesis example 27, difference is to replace with N- (4- phenanthryl) aniline Equivalent N- (4- phenanthryl) 2- naphthylamines, after the completion of reaction, isolated faint yellow solid 3.7g, yield 61%.
Synthesis example 28
The synthesis of E3
Using the method prepare compound E3 identical with synthesis example 27, difference is to replace with N- (4- phenanthryl) aniline Equivalent N- (4- phenanthryl) 2- dibenzothiophenes, after the completion of reaction, isolated faint yellow solid 3.7g, yield 65%.
Synthesis example 29
The synthesis of E4
Using the method prepare compound E4 identical with synthesis example 27, difference is to replace with N- (4- phenanthryl) aniline Equivalent N- (4- phenanthryl) -9,9- dimethyl fluorene -2- amine, after the completion of reaction, isolated faint yellow solid 3.8g, yield is 64%.
Synthesis example 30
The synthesis of F1
5- bromines 7,7,13,13- tetramethyl -7,13- dihydrobenzo [g] indeno [1,2-B] fluorenes (10mmol, 4.4g) (10mmol, 2.8g) and N- (4- phenanthryl) -2-aminotoluene (22mmol, 6g), sodium tert-butoxide 5.7g, toluene 100mL, solution liquid Lead to nitrogen 30min under face, add 0.2g Pd2 (dba) 3, inject 10% tri-tert-butylphosphine 2ml with syringe, open stirring, 120 degrees Celsius are heated to, after reacting 4 hours, reaction solution washing, organic phase concentrates, and re crystallization from toluene obtains light yellow solid 4.8g, Yield 75%.
1H NMR(500MHz,Chloroform)δ8.98(s,1H),8.85(s,1H),8.70(s,1H),8.24(s, 1H), 8.13 (d, J=17.9Hz, 2H), 7.91 (d, J=10.0Hz, 2H), 7.81-7.44 (m, 9H), 7.40-7.08 (m, 6H),6.90(s,1H),2.13(s,3H),1.75(s,6H),1.69(s,6H).
Synthesis example 31
The synthesis of F2
Using the method prepare compound F2 identical with synthesis example 27, difference is N- (4- phenanthryl) -2-aminotoluene Equivalent N- (4- phenanthryl) -2,4- dimethylanilines are replaced with, after the completion of reaction, isolated faint yellow solid 4.9g, yield It is 74%.
Synthesis example 32
The synthesis of F3
Using the method prepare compound F3 identical with synthesis example 27, difference is N- (4- phenanthryl) -2-aminotoluene Equivalent N- (4- phenanthryl) -4- cyclohexyl aniline is replaced with, after the completion of reaction, isolated faint yellow solid 5.0g, yield is 71%.
Synthesis example 33
The synthesis of F4
Using the method prepare compound F4 identical with synthesis example 27, difference is N- (4- phenanthryl) -2-aminotoluene Equivalent N- (4- phenanthryl) -2- benzidine is replaced with, after the completion of reaction, isolated faint yellow solid 5.4g, yield 76%.
Synthesis example 34
The synthesis of F5
Using the method prepare compound F5 identical with synthesis example 27, difference is N- (4- phenanthryl) -2-aminotoluene Equivalent N- (4- phenanthryl)-naphthalidine is replaced with, after the completion of reaction, isolated faint yellow solid 5.0g, yield 73%.
Synthesis example 35
The synthesis of F6
Using the method prepare compound F6 identical with synthesis example 27, difference is N- (4- phenanthryl) -2-aminotoluene Equivalent N- (4- phenanthryl) -1- phenanthrene amine is replaced with, after the completion of reaction, isolated faint yellow solid 4.5g, yield 62%.
Synthesis example 36
The synthesis of F7
Using the method prepare compound F7 identical with synthesis example 27, difference is N- (4- phenanthryl) -2-aminotoluene Equivalent N- (4- phenanthryl) -3- benzidine is replaced with, after the completion of reaction, isolated faint yellow solid 5.1g, yield 74%.
Synthesis example 37
The synthesis of F8
Using the method prepare compound F8 identical with synthesis example 27, difference is N- (4- phenanthryl) -2-aminotoluene Equivalent N- (4- phenanthryl) -4- phenylpyridine -2- amine is replaced with, after the completion of reaction, isolated faint yellow solid 4.8g, yield It is 68%.
Synthesis example 38
The synthesis of F9
Using the method prepare compound F9 identical with synthesis example 27, difference is N- (4- phenanthryl) -2-aminotoluene Equivalent N- (4- phenanthryl)-quinoline -2- amine is replaced with, after the completion of reaction, isolated faint yellow solid 4.4g, yield is 65%.
Synthesis example 39
The synthesis of F10
Using the method prepare compound F10 identical with synthesis example 27, difference is N- (4- phenanthryl) -2-aminotoluene Equivalent N- (4- phenanthryl) -9,9- dimethyl fluorene -2- amine is replaced with, after the completion of reaction, isolated faint yellow solid 4.7g is received Rate is 63%.
1H NMR (500MHz, Chloroform) δ 8.98 (dd, J=14.1,3.8Hz, 1H), 8.93-8.80 (m, 1H), 8.73 (s, 1H), 8.24 (dd, J=14.9,3.1Hz, 1H), 8.20-8.08 (m, 2H), 7.98-7.82 (m, 4H), 7.80- 7.45 (m, 11H), 7.41-7.16 (m, 5H), 6.98 (dd, J=15.0,3.1Hz, 1H), 1.75 (s, 6H), 1.69 (s, 12H)
Using mass spectral analysis and elemental analysis compound A1 to A15, B1 to B4, C1 to C4, D1 to D2, E1 to E4, F1 extremely F10 is characterized, and data are shown in Table 1.
1 synthetic example characterization of compound data of table
The device embodiments of each compound of the present invention
The technique effect of the compounds of this invention is described in detail below by way of device embodiments.
Device embodiments 1
The glass plate for being coated with transparent conductive layer in commercial detergent is ultrasonically treated, is rinsed in deionized water, In acetone: ultrasonic oil removing in alcohol mixed solvent (volume ratio 1: 1) is baked under clean environment and removes moisture content completely, with purple Outer light and ozone clean, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, 1 × 10-5~9 × 10-3Pa is evacuated to, upper It states vacuum evaporation 2-TNATA on anode tunic and film thickness 10nm is deposited as hole injection layer, evaporation rate 0.1nm/s；
Hole transmission layers of the vacuum evaporation NPB as device on hole injection layer, evaporation rate 0.1nm/s steam Plating total film thickness is 80nm；
The luminescent layer of vacuum evaporation device on hole transmission layer, luminescent layer include material of main part and dye materials, profit The method steamed altogether with multi-source, it is 0.1nm/s to adjust material of main part ADN evaporation rates, and 3% ratio of dyestuff DSA-Ph evaporation rates is set Fixed, vapor deposition total film thickness is 30nm；
The electron transport layer materials Bphen of vacuum evaporation device, evaporation rate 0.1nm/s on luminescent layer steam Plating total film thickness is 30nm；
Vacuum evaporation thickness is the LiF of 0.5nm as electron injecting layer, thickness 150nm on electron transfer layer (ETL) Cathode of the Al layers as device.
The structure of organic electroluminescence device is in device embodiments 1 of the present invention：
ITO/2-TNATA (10nm)/NPB (80nm)/ADN ﹕ DSA-Ph (30nm)/Bphen (30nm)/LiF (1nm)/Al.
Each functional layer material molecular structure is as follows：
Device embodiments 2
Method is identical with device embodiments 1, different from DSA-Ph to be replaced with to the A1 of equivalent
Device embodiments 3
Method is identical with device embodiments 1, different from DSA-Ph to be replaced with to the A7 of equivalent
Device embodiments 4
Method is identical with device embodiments, different from DSA-Ph to be replaced with to the A14 of equivalent
Device embodiments 5
Method is identical with device embodiments, different from DSA-Ph to be replaced with to the A15 of equivalent
Device embodiments 6
Method is identical with device embodiments, different from DSA-Ph to be replaced with to the B2 of equivalent
Device embodiments 7
Method is identical with device embodiments, different from DSA-Ph to be replaced with to the C2 of equivalent
Device embodiments 8
Method is identical with device embodiments, different from DSA-Ph to be replaced with to the D2 of equivalent
Device embodiments 9
Method is identical with device embodiments, different from DSA-Ph to be replaced with to the E4 of equivalent
Device embodiments 10
Method is identical with device embodiments, different from DSA-Ph to be replaced with to the F1 of equivalent
Device embodiments 11
Method is identical with device embodiments, different from DSA-Ph to be replaced with to the F5 of equivalent
Under similary brightness 1000cd/m2, the drive of organic electroluminescence device being prepared in device embodiments 1 is measured Dynamic voltage and current efficiency and CIE coordinate values, corresponding performance indicator refer to the following table 2.
Table 2：
It can be seen from upper table dark blue light, color can be realized compared to skyr blue photoinitiator dye DSA-Ph, the compounds of this invention Between coordinate y values 0.1-0.18, the demand of a variety of different blue-light devices can be met；Comparative device embodiment 1 and device are real Apply example 2, it can be seen that using the sky blue photoinitiator dye DSA-Ph of control compounds as luminescent material, chromaticity coordinates for (0.14, 0.35), apply the blue-light device of the compounds of this invention A1, chromaticity coordinates has reached (0.14,0.15), be a kind of performance more preferably Deeper blue light material.The above result shows that new organic materials of the invention are used for organic electroluminescence device, it can be effective Reduction landing voltage, improve current efficiency, be blue light dye materials of good performance.
During the preferred embodiment of the present invention has been described above in detail, but present invention is not limited to the embodiments described above Detail within the scope of the technical concept of the present invention, can carry out a variety of simple variants to technical scheme of the present invention, these Simple variant all belongs to the scope of protection of the present invention, and in order to avoid unnecessary repetition, the present invention is to various possible simple changes Type mode no longer separately illustrates.In addition, various embodiments of the present invention can be combined randomly, as long as Its thought without prejudice to the present invention, it should also be regarded as the disclosure of the present invention.

Claims (8)

1. shown in a kind of general formula compound such as following formula (I)：
Wherein：
Ar is selected from C6~C50Substituted or non-substituted aryl, C6~C50Substituted or non-substituted condensed-nuclei aromatics group, C4~ C50Substituted or non-substituted heteroaryl, C4~C50Substituted or non-substituted condensed hetero ring aromatic hydrocarbon group；
Above-mentioned heteroaryl and condensed hetero ring aromatic hydrocarbon group are comprising one or more miscellaneous originals for being selected from B, N, O, S, P (=O), Si and P Son and the monocyclic or fused ring aryl with 4~50 ring carbon atoms；
It is above-mentioned when Ar be selected from substitution aryl, substitution condensed-nuclei aromatics group, substitution heteroaryl when or substituted condensed hetero ring virtue During hydrocarbyl group, the substituent group is selected from C1~C12Straight chained alkyl, branched alkyl or cycloalkyl；
N is 1 or 2；
As n=2, L is selected from structure shown in following formula A, B, C or D：
As n=1, L is selected from structure shown in following formula E or F：
2. according to the general formula compound described in claim 1, wherein：
Ar is selected from C6~C24Substituted or non-substituted aryl, C6~C24Substituted or non-substituted condensed-nuclei aromatics group, C4~C30's Substituted or non-substituted heteroaryl, C4~C30Substituted or non-substituted condensed ring heteroaryl hydrocarbyl group；The above-mentioned Ar that works as is selected from heteroaryl Or during condensed ring heteroaryl hydrocarbyl group, the hetero atom is selected from O, S or N.
3. according to the general formula compound described in claim 1, wherein：
Ar is selected from phenyl, aminomethyl phenyl, phenanthryl, xenyl, dibenzothiophene, naphthalene, phenanthryl, quinolyl, pyridyl group, anthracene Base, terphenyl, fluorenyl, furyl, thienyl, pyrrole radicals, benzofuranyl, benzothienyl, isobenzofuran-base, indoles Two between base, dibenzothiophene, 9- phenyl carbazoles, 9- naphthyl carbazoles, benzo carbazole, dibenzo-carbazole, indolocarbazole, benzo Oxole base.
4. according to the general formula compound described in one of claim 1-3, selected from following concrete structure formulas
5. purposes of the general formula compound according to one of claim 1-3 in organic electroluminescence device.
6. purposes of the structural compounds according to claim 4 in organic electroluminescence device.
7. a kind of organic electroluminescence device, including including one layer at least containing luminescent layer between anode, cathode and two electrodes And above organic function layer, at least one layer wherein in the organic function layer contain claim individually or as blending constituent Compound described in any one of 1-4.
8. organic electroluminescence device according to claim 7, wherein, at least one layer organic function layer is luminous Layer.
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