CN103030630A - Organic material and organic electroluminescent device adopting organic material - Google Patents

Organic material and organic electroluminescent device adopting organic material Download PDF

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CN103030630A
CN103030630A CN2011103024146A CN201110302414A CN103030630A CN 103030630 A CN103030630 A CN 103030630A CN 2011103024146 A CN2011103024146 A CN 2011103024146A CN 201110302414 A CN201110302414 A CN 201110302414A CN 103030630 A CN103030630 A CN 103030630A
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邱勇
李银奎
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Tsinghua University
Beijing Visionox Technology Co Ltd
Kunshan Visionox Display Co Ltd
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Tsinghua University
Beijing Visionox Technology Co Ltd
Kunshan Visionox Display Co Ltd
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Abstract

The invention relates to an organic material and an organic electroluminescent device containing the organic material. The general structural formula of the material is shown as following, wherein R1 to R7 are selected from sub-polycyclic aromatic hydrocarbons with 6 to 30 carbon atoms or selected from sub-polycyclic heterocyclic aromatic hydrocarbons with 6 to 30 carbon atoms or selected from alkanes with 6 to 20 carbon atoms. The organic material provided by the invention can be used as a phosphorescent body material or a hole transport layer material in the organic electroluminescent device.

Description

A kind of organic materials and adopt the organic electroluminescence device of such material
Technical field
The present invention relates to a kind of novel organic materials, adopt the organic electroluminescence device of such novel organic materials, belong to the ORGANIC ELECTROLUMINESCENCE DISPLAYS technical field.
Background technology
Display of organic electroluminescence (claims again Organic Light Emitting Diode, organic light-emitting diode, OLED) research starts from and adds the sixties in century, the people such as Pope (Pope M, Kallmann HP, and Magnante R J.cHEM.PHYs., 1963,38,2042) reported first the electro optical phenomenon of green onion monocrystalline, opened the electroluminescent prelude of organic solid.1987, (the C.W.Tang such as the researchist CW.Tang of Kodak, S.A.Vanslyke, APL.Phys.Lett., 1987,51,913) on the basis of summing up previous work, double-deck design philosophy has been proposed, selection has the derivative of tri-arylamine group of better film forming properties and 8 monohydroxy quinoline aluminum title complexs (Alq3) respectively as hole transmission layer and luminescent layer (hole transmission layer of holding concurrently), has obtained high-quantum efficiency (1%), high-luminous-efficiency (1.5lm/W), high brightness (＞1000cd/m 2) and low driving voltage (＜10V) organic electroluminescence device; Nineteen ninety, (the Burroughes J such as R.H.Friend in Cambridge University Cavendish laboratory, Bradley DDC, Brown AR, Friend RH, Nature (London), 1990,347,539) make polymer electroluminescent device take poly-phenylene vinylene (ppv) (P PV) as the luminescent layer material, opened up another frontier one Polymer Thin Film Electroluminescent Devices of luminescent device.These two breakthroughs make people see the potential hope of organic electroluminescence device as flat-panel display device of new generation.
In the research of recent years, no matter in the demonstration field or in the white-light illuminating field, high efficiency phosphor material has become research emphasis.In phosphor material, because electronics and hole are in organic electroluminescent device, the multiplicity difference that spins during restructuring, the ratio of singlet excimer and triplet state excimer is 1: 3, so the 3-4 when its luminous efficiency can reach independent use fluorescent material in the phosphorescence device doubly.
In the research of phosphorescent light body material and using, carbazole derivative is research, report and use maximum.Merck ﹠ Co., Inc. has applied for aromatic hydrocarbons or the condensed-nuclei aromatics derivative patent (application number 200780050158.8 that two carbazyls replace, publication number CN 101600777A), they declare that when making main body with phenylbenzene CBP in red dye, can reach 11000 hours work-ing life; The Idemitsu Kosen Co., Ltd. of Japan has the many pieces of various carbazole derivative of patent report to can be used as phosphorescent light body material (application number 200480004828.9, publication number CN 1753967A), one type azepine carbazole derivative is wherein arranged as phosphorescent light body material (application number 200380105706.4, publication number CN 1723258A), can in various types of phosphorescent colorings, make the main body material.In present phosphorescent light body material research, remain with the carbazole derivative better performances.
Summary of the invention
The objective of the invention is to propose the acridan derivative of the new carbazyl phenyl substituted of a class, this compounds can be used for organic electroluminescent luminous and technique of display field.
The phosphorescent light body material of the acridan derivative of this type of new carbazyl phenyl substituted that the present invention proposes.In theory, because the existence of sp3 hydridization C atom in the molecule, so that two carbazole groups in the molecule and triarylamine group do not have mutually conjugation, thereby the performance of whole molecule is, triplet energy state is higher, be suitable for doing the material of main part of phosphor material, and carbazole and triarylamine group all are the transport groups of excellent performance, are suitable for doing in the phosphorescence device material of main part of phosphorescent coloring.In addition, because the excellent transmission performance of carbazole and triarylamine group,, in the phosphorescence electroluminescence device, also can be used as hole mobile material.
The present invention provides one type of organic materials that can be used for the phosphorescence device, this material is made the material of main part of phosphorescent coloring in the phosphorescence device, the characteristics of this material are to have higher triplet, and with the molecular orbital(MO) of dyestuff coupling, make electronics and hole successfully enter dyestuff by material of main part, exciton is compound and luminous at dye coating, material provided by the invention has higher second-order transition temperature and excellent film forming properties simultaneously, can in the phosphorescence device, form stable film, can effectively transmit hole and electronics.In addition, we find, because the various materials among the present invention are acridan derivatives of carbazyl phenyl substituted, are rich in electronics, also can be used as hole mobile material in the phosphorescence electroluminescence device.
The acridan derivative of carbazyl phenyl substituted of the present invention, its structural formula is suc as formula shown in (1):
Figure BDA0000096724570000021
Wherein, it is 6 to 30 inferior condensed-nuclei aromatics that R1 to R7 is selected from carbonatoms, or to be selected from carbonatoms be 6 to 30 inferior fused heterocycle aromatic hydrocarbons, or to be selected from carbonatoms be 6 to 20 alkane.
The compound of above-mentioned general formula (1) can be described for following formula:
In order more to clearly demonstrate content of the present invention, lower mask body has been listed the preferred structure in the type of compounds that the present invention relates to:
Figure BDA0000096724570000031
Figure BDA0000096724570000041
Figure BDA0000096724570000051
Figure BDA0000096724570000061
Figure BDA0000096724570000071
Figure BDA0000096724570000081
The above-mentioned novel cpd that contains carbazole group of the present invention can be used as the material of main part of phosphorescent coloring, and these materials have higher hole migration ability and triplet simultaneously, can be used as the hole mobile material of phosphorescence device.
The present invention also protects a kind of organic electroluminescence device, wherein comprises pair of electrodes and is arranged on this to the organic light emitting medium between the electrode, comprises at least a kind of described material of above-mentioned general formula (1) that is selected from this organic light emitting medium.
Comprise luminescent layer and hole transport one functional layer in the above-mentioned organic light emitting medium, wherein comprise at least a described material of above-mentioned general formula (1) that is selected from phosphorescence luminescent layer or the hole transport functional layer.
Embodiment
The synthetic method embodiment of novel material part:
Used various o-dibromobenzenes among the present invention, various replacement or not the basic chemical industry raw materials such as substituted diphenylamine, organic bases, phosphorous palladium-containing catalyst all can conveniently buy in Chemicals market.
Synthesizing of embodiment 1 compound 1
The first step
Figure BDA0000096724570000091
11.8 gram (50mmol) o-dibromobenzene, 9.31 gram (55mmol) pentanoic are dissolved in the 150ml toluene, add 7.9 gram (82.5mmol) sodium tert-butoxides, the Pd (dba) of 0.86 gram (1.5mmol, 3%) 2, the tri-butyl phosphine of 4ml10% () 2mmol.Stir heating, back flow reaction.After 3 hours, produce a lot of product precipitations, can't stir, add saturated sodium bicarbonate solution and make reaction terminating, separatory.Product separates with column chromatography, obtains thick faint yellow oily thing 8.7 grams.The point plate only has a point, namely drops into the next step.
Second step
Figure BDA0000096724570000092
8.7 the adjacent bromine triphenylamine of gram is dissolved among the THF of 60ml, is chilled to-78 ℃, adds the n-Butyl Lithium of 14.5ml.Behind the low-temp reaction 1 hour, add 12 grams to the bromine benzophenone, at-78 ℃ of lower reaction 30min, then naturally be warming up to room temperature, stirring is spent the night, adding ammonium chloride solution termination reaction, ethyl acetate extraction is drained, and gets thick thing, is directly used in next step reaction.
The 3rd step
The second step reaction product is dissolved in the THF of 20ml, 50ml acetic acid, and the 5ml concentrated hydrochloric acid, reflux 5hrs, solid is separated out in cooling, leaches, and content 98.6% without further processing, directly drops into next step reaction.
The 4th step
The 3rd step product that in the there-necked flask of a 500ml, adds 1.766 grams (content 98.6%, 0.00307mol, molecular weight 567), 2.116 gram (content 80%, 0.0101mol, molecular weight 167) carbazole, cuprous iodide 0.176 gram (0.00092mol, molecular weight 190), salt of wormwood 2.54 grams (0.0184mol, molecular weight 138), 18-hat-6 usefulness 0.122 gram (0.00046mol, molecular weight 264), DMPU (N, N-dimethyl propylene thiazolinyl urea) 25ml.Under nitrogen protection, reflux 10hrs adds 5 gram carbazoles again in the middle of the reaction.Behind the stopped reaction, naturally be chilled to room temperature, in reaction solution impouring 450ml water, solid is separated out, filter, solid dissolves with methylene dichloride, concentrates most of methylene dichloride, under agitation add dehydrated alcohol, have yellow solid product to separate out, solid product adds the mixed solvent heat of methylene dichloride and dehydrated alcohol again and boils, and filters to obtain faint yellow solid product 2.107 grams, purity 98.3%, yield 92.9%.
Product MS (m/e): 739; Ultimate analysis (C 55H 37N 3): theoretical value C:89.28%, H:5.04%, N:5.68%; Measured value C:89.40%, H:4.99%, N:5.61%.
Synthesizing of embodiment 2 compounds 2
Figure BDA0000096724570000102
Synthesis step is same as the synthetic of compound 1, just the starting material carbazole in the four-step reaction is changed to 3-methyl carbazole, obtains the faint yellow solid product.
Product MS (m/e): 767; Ultimate analysis (C 57H 41N 3): theoretical value C:89.15%, H:5.38%, N:5.47%; Measured value C:89.20%, H:5.29%, N:5.51%.
Synthesizing of embodiment 3 compounds 3
Figure BDA0000096724570000111
Synthesis step is same as the synthetic of compound 1, just the starting material carbazole in the four-step reaction is changed to 3, and the 6-Dimethylcarbazole obtains the faint yellow solid product.
Product MS (m/e): 795; Ultimate analysis (C 59H 45N 3): theoretical value C:89.02%, H:5.70%, N:5.28%; Measured value C:89.08%, H:5.65%, N:5.27%.
Synthesizing of embodiment 4 compounds 4
Synthesis step is same as the synthetic of compound 1, just the starting material pentanoic in the first step reaction is changed to 4, and 4 '-dimethyl pentanoic obtains the faint yellow solid product.
Product MS (m/e): 767; Ultimate analysis (C 57H 41N 3): theoretical value C:89.15%, H:5.38%, N:5.47%; Measured value C:89.10%, H:5.42%, N:5.48%.
Synthesizing of embodiment 5 compounds 5
Figure BDA0000096724570000121
Synthesis step is same as the synthetic of compound 1, just the starting material pentanoic in the first step reaction is changed to 4, and 4 '-dimethyl pentanoic is changed to 3-methyl carbazole with the starting material carbazole in the four-step reaction, obtains the faint yellow solid product.
Product MS (m/e): 795; Ultimate analysis (C 59H 45N 3): theoretical value C:89.02%, H:5.70%, N:5.28%; Measured value C:89.05%, H:5.73%, N:5.22%.
Synthesizing of embodiment 6 compounds 6
Synthesis step is same as the synthetic of compound 1, just the starting material pentanoic in the first step reaction is changed to 4, and 4 '-dimethyl pentanoic is changed to 3 with the starting material carbazole in the four-step reaction, and the 6-Dimethylcarbazole obtains the faint yellow solid product.
Product MS (m/e): 823; Ultimate analysis (C 61H 49N 3): theoretical value C:88.91%, H:5.99%, N:5.10%; Measured value C:89.02%, H:5.95%, N:5.03%.
Synthesizing of embodiment 7 compounds 7
Synthesis step is same as the synthetic of compound 1, just the starting material pentanoic in the first step reaction is changed to 3, and 3 '-dimethyl pentanoic obtains the faint yellow solid product.
Product MS (m/e): 767; Ultimate analysis (C 57H 41N 3): theoretical value C:89.15%, H:5.38%, N:5.47%; Measured value C:89.14%, H:5.40%, N:5.46%.
Synthesizing of embodiment 8 compounds 8
Synthesis step is same as the synthetic of compound 1, just the starting material pentanoic in the first step reaction is changed to 3,3 '-dimethyl pentanoic, and the starting material carbazole in the four-step reaction is changed to 3-methyl carbazole, obtains the faint yellow solid product.
Product MS (m/e): 795; Ultimate analysis (C 59H 45N 3): theoretical value C:89.02%, H:5.70%, N:5.28%; Measured value C:89.01%, H:5.69%, N:5.30%.
Synthesizing of embodiment 9 compounds 9
Figure BDA0000096724570000133
Synthesis step is same as the synthetic of compound 1, just the starting material pentanoic in the first step reaction is changed to 3,3 '-dimethyl pentanoic, and the starting material carbazole in the four-step reaction is changed to 3, and the 6-Dimethylcarbazole obtains the faint yellow solid product.
Product MS (m/e): 823; Ultimate analysis (C 61H 49N 3): theoretical value C:88.91%, H:5.99%, N:5.10%; Measured value C:88.86%, H:5.93%, N:5.21%.
Synthesizing of embodiment 10 compounds 10
Figure BDA0000096724570000141
Synthesis step is same as the synthetic of compound 1, just the starting material pentanoic in the first step reaction is changed to 2, and 2 '-dimethyl pentanoic obtains the faint yellow solid product.
Product MS (m/e): 767; Ultimate analysis (C 57H 41N 3): theoretical value C:89.15%, H:5.38%, N:5.47%; Measured value C:89.19%, H:5.45%, N:5.36%.
Synthesizing of embodiment 11 compounds 11
Synthesis step is same as the synthetic of compound 1, just the starting material pentanoic in the first step reaction is changed to 2,2 '-dimethyl pentanoic, and the starting material carbazole in the four-step reaction is changed to 3-methyl carbazole, obtains the faint yellow solid product.
Product MS (m/e): 795; Ultimate analysis (C 59H 45N 3): theoretical value C:89.02%, H:5.70%, N:5.28%; Measured value C:89.05%, H:5.83%, N:5.12%.
Synthesizing of embodiment 12 compounds 12
Figure BDA0000096724570000143
Synthesis step is same as the synthetic of compound 1, just the starting material pentanoic in the first step reaction is changed to 2,2 '-dimethyl pentanoic, and the starting material carbazole in the four-step reaction is changed to 3, and the 6-Dimethylcarbazole obtains the faint yellow solid product.
Product MS (m/e): 823; Ultimate analysis (C 61H 49N 3): theoretical value C:88.91%, H:5.99%, N:5.10%; Measured value C:88.89%, H:5.91%, N:5.20%.
Synthesizing of embodiment 13 compounds 13
Figure BDA0000096724570000151
Synthesis step is same as the synthetic of compound 1, just the starting material carbazole in the four-step reaction is changed to the 3-phenyl carbazole, obtains the faint yellow solid product.
Product MS (m/e): 891; Ultimate analysis (C 67H 45N 3): theoretical value C:90.21%, H:5.08%, N:4.71%; Measured value C:90.10%, H:5.03%, N:4.87%.
Synthesizing of embodiment 14 compounds 14
Figure BDA0000096724570000152
Synthesis step is same as the synthetic of compound 1, just the starting material pentanoic in the first step reaction is changed to 4,4 '-dimethyl pentanoic, and the starting material carbazole in the four-step reaction is changed to the 3-phenyl carbazole, obtains the faint yellow solid product.
Product MS (m/e): 919; Ultimate analysis (C 69H 49N 3): theoretical value C:90.07%, H:5.37%, N:4.57%; Measured value C:90.10%, H:5.03%, N:4.87%.
Synthesizing of embodiment 15 compounds 15
Synthesis step is same as the synthetic of compound 1, just the starting material pentanoic in the first step reaction is changed to 3,3 '-dimethyl pentanoic, and the starting material carbazole in the four-step reaction is changed to the 3-phenyl carbazole, obtains the faint yellow solid product.
Product MS (m/e): 919; Ultimate analysis (C 69H 49N 3): theoretical value C:90.07%, H:5.37%, N:4.57%; Measured value C:90.02%, H:5.59%, N:4.39%.
Synthesizing of embodiment 16 compounds 16
Synthesis step is same as the synthetic of compound 1, just the starting material pentanoic in the first step reaction is changed to 2,2 '-dimethyl pentanoic, and the starting material carbazole in the four-step reaction is changed to the 3-phenyl carbazole, obtains the faint yellow solid product.
Product MS (m/e): 919; Ultimate analysis (C 69H 49N 3): theoretical value C:90.07%, H:5.37%, N:4.57%; Measured value C:90.12%, H:5.39%, N:4.49%.
Synthesizing of embodiment 17 compounds 17
Figure BDA0000096724570000162
Synthesis step is same as the synthetic of compound 1, just the starting material o-dibromobenzene in the first step reaction is changed to the adjacent bromo-iodobenzene of methyl, obtains the faint yellow solid product.
Product MS (m/e): 753; Ultimate analysis (C 56H 39N 3): theoretical value C:89.21%, H:5.21%, N:5.57%; Measured value C:89.19%, H:5.34%, N:5.47%.
Synthesizing of embodiment 18 compounds 18
Synthesis step is same as the synthetic of compound 1, just the starting material o-dibromobenzene in the first step reaction is changed to the adjacent bromo-iodobenzene of methyl, and pentanoic is changed to 4, and 4 '-dimethyl pentanoic obtains the faint yellow solid product.
Product MS (m/e): 781; Ultimate analysis (C 58H 43N 3): theoretical value C:89.08%, H:5.55%, N:5.37%; Measured value C:89.06%, H:5.51%, N:5.43%.
Synthesizing of embodiment 19 compounds 19
Figure BDA0000096724570000171
Synthesis step is same as the synthetic of compound 1, just the starting material o-dibromobenzene in the first step reaction is changed to the adjacent bromo-iodobenzene of methyl, and pentanoic is changed to 3, and 3 '-dimethyl pentanoic obtains the faint yellow solid product.
Product MS (m/e): 781; Ultimate analysis (C 58H 43N 3): theoretical value C:89.08%, H:5.55%, N:5.37%; Measured value C:89.12%, H:5.58%, N:5.30%.
Synthesizing of embodiment 20 compounds 20
Figure BDA0000096724570000172
Synthesis step is same as the synthetic of compound 1, just the starting material o-dibromobenzene in the first step reaction is changed to the adjacent bromo-iodobenzene of methyl, and pentanoic is changed to 2, and 2 '-dimethyl pentanoic obtains the faint yellow solid product.
Product MS (m/e): 781; Ultimate analysis (C 58H 43N 3): theoretical value C:89.08%, H:5.55%, N:5.37%; Measured value C:89.10%, H:5.61%, N:5.29%.
Synthesizing of embodiment 21 compounds 21
Figure BDA0000096724570000173
Synthesis step is same as the synthetic of compound 1, just the starting material o-dibromobenzene in the first step reaction is changed to the adjacent bromo-iodobenzene of methyl, pentanoic is changed to 4,4 '-dimethyl pentanoic, starting material carbazole in the four-step reaction is changed to 3-methyl carbazole, obtains the faint yellow solid product.
Product MS (m/e): 809; Ultimate analysis (C 60H 47N 3): theoretical value C:88.96%, H:5.85%, N:5.19%; Measured value C:89.03%, H:5.74%, N:5.23%.
Synthesizing of embodiment 22 compounds 22
Figure BDA0000096724570000181
Synthesis step is same as the synthetic of compound 1, just the starting material o-dibromobenzene in the first step reaction is changed to the adjacent bromo-iodobenzene of methyl, and pentanoic is changed to 4,4 '-dimethyl pentanoic, starting material carbazole in the four-step reaction is changed to 3, and the 6-Dimethylcarbazole obtains the faint yellow solid product.
Product MS (m/e): 837; Ultimate analysis (C 62H 51N 3): theoretical value C:88.85%, H:6.13%, N:5.01%; Measured value C:88.91%, H:5.98%, N:5.11%.
Synthesizing of embodiment 23 compounds 23
Figure BDA0000096724570000182
Synthesis step is same as the synthetic of compound 1, just the starting material o-dibromobenzene in the first step reaction is changed to the adjacent bromo-iodobenzene of methyl, pentanoic is changed to 4,4 '-dimethyl pentanoic, starting material carbazole in the four-step reaction is changed to the 3-phenyl carbazole, obtains the faint yellow solid product.
Product MS (m/e): 837; Ultimate analysis (C 70H 51N 3): theoretical value C:90.00%, H:5.50%, N:4.50%; Measured value C:90.05%, H:5.34%, N:4.61%.
Synthesizing of embodiment 24 compounds 24
Synthesis step is same as the synthetic of compound 1, just the starting material o-dibromobenzene in the first step reaction is changed to the adjacent bromo-iodobenzene of methyl, pentanoic is changed to 2,2 '-dimethyl pentanoic, starting material carbazole in the four-step reaction is changed to 3-methyl carbazole, obtains the faint yellow solid product.
Product MS (m/e): 809; Ultimate analysis (C 60H 47N 3): theoretical value C:88.96%, H:5.85%, N:5.19%; Measured value C:88.89%, H:5.90%, N:5.21%.
Synthesizing of embodiment 25 compounds 25
Figure BDA0000096724570000191
Synthesis step is same as the synthetic of compound 1, just the starting material o-dibromobenzene in the first step reaction is changed to the adjacent bromo-iodobenzene of methyl, and pentanoic is changed to 2,2 '-dimethyl pentanoic, starting material carbazole in the four-step reaction is changed to 3, and the 6-Dimethylcarbazole obtains the faint yellow solid product.
Product MS (m/e): 837; Ultimate analysis (C 62H 51N 3): theoretical value C:88.85%, H:6.13%, N:5.01%; Measured value C:88.89%, H:6.03%, N:5.08%.
Synthesizing of embodiment 26 compounds 26
Synthesis step is same as the synthetic of compound 1, just the starting material o-dibromobenzene in the first step reaction is changed to the adjacent bromo-iodobenzene of methyl, pentanoic is changed to 2,2 '-dimethyl pentanoic, starting material carbazole in the four-step reaction is changed to the 3-phenyl carbazole, obtains the faint yellow solid product.
Product MS (m/e): 933; Ultimate analysis (C 70H 51N 3): theoretical value C:90.00%, H:5.50%, N:4.50%; Measured value C:89.91%, H:5.38%, N:4.71%.
Synthesizing of embodiment 27 compounds 27
Figure BDA0000096724570000193
Synthesis step is same as the synthetic of compound 1, just the starting material o-dibromobenzene in the first step reaction is changed to the adjacent bromo-iodobenzene of methyl, pentanoic is changed to 3,3 '-dimethyl pentanoic, starting material carbazole in the four-step reaction is changed to the 3-phenyl carbazole, obtains the faint yellow solid product.
Product MS (m/e): 933; Ultimate analysis (C 70H 51N 3): theoretical value C:90.00%, H:5.50%, N:4.50%; Measured value C:90.15%, H:5.48%, N:4.37%.
Synthesizing of embodiment 28 compounds 28
Figure BDA0000096724570000201
Synthesis step is same as the synthetic of compound 1, just the starting material in the second step reaction is changed to a bromobenzene ketone to the bromobenzene ketone, obtains the faint yellow solid product.
Product MS (m/e): 739; Ultimate analysis (C 55H 37N 3): theoretical value C:89.28%, H:5.04%, N:5.68%; Measured value C:89.34%, H:5.11%, N:5.55%.
Synthesizing of embodiment 29 compounds 29
Figure BDA0000096724570000202
Synthesis step is same as the synthetic of compound 1, just the starting material pentanoic in the first step reaction is changed to 4,4 '-dimethyl pentanoic, and the starting material in the second step reaction are changed to a bromobenzene ketone to the bromobenzene ketone, obtain the faint yellow solid product.
Product MS (m/e): 767; Ultimate analysis (C 57H 41N 3): theoretical value C:89.15%, H:5.38%, N:5.47%; Measured value C:89.20%, H:5.41%, N:5.39%.
Synthesizing of embodiment 30 compounds 30
Figure BDA0000096724570000203
Synthesis step is same as the synthetic of compound 1, just the starting material o-dibromobenzene in the first step reaction is changed to the adjacent bromo-iodobenzene of methyl, pentanoic is changed to 3,3 '-dimethyl pentanoic, starting material in the second step reaction are changed to a bromobenzene ketone to the bromobenzene ketone, obtain the faint yellow solid product.
Product MS (m/e): 781; Ultimate analysis (C 58H 43N 3): theoretical value C:89.08%, H:5.55%, N:5.37%; Measured value C:89.12%, H:5.63%, N:5.25%.
Synthesizing of embodiment 31 compounds 31
Figure BDA0000096724570000211
Synthesis step is same as the synthetic of compound 1, just the starting material o-dibromobenzene in the first step reaction is changed to the adjacent bromo-iodobenzene of methyl, pentanoic is changed to 3,3 '-dimethyl pentanoic, starting material in the second step reaction are changed to a bromobenzene ketone to the bromobenzene ketone, starting material carbazole in the four-step reaction is changed to 3, and the 6-Dimethylcarbazole obtains the faint yellow solid product.
Product MS (m/e): 837; Ultimate analysis (C 62H 51N 3): theoretical value C:88.85%, H:6.13%, N:5.01%; Measured value C:88.80%, H:6.21%, N:4.99%.
Synthesizing of embodiment 32 compounds 32
Figure BDA0000096724570000212
Synthesis step is same as the synthetic of compound 1, just the starting material in the second step reaction is changed to a bromobenzene ketone to the bromobenzene ketone, and the starting material carbazole in the four-step reaction is changed to 3, and the 6-Dimethylcarbazole obtains the faint yellow solid product.
Product MS (m/e): 795; Ultimate analysis (C 59H 45N 3): theoretical value C:89.02%, H:5.70%, N:5.28%; Measured value C:89.04%, H:5.78%, N:5.18%.
Synthesizing of embodiment 33 compounds 33
Figure BDA0000096724570000221
Synthesis step is same as the synthetic of compound 1, just the starting material in the second step reaction is changed to a bromobenzene ketone to the bromobenzene ketone, and the starting material carbazole in the four-step reaction is changed to 3 phenyl carbazoles, obtains the faint yellow solid product.
Product MS (m/e): 891; Ultimate analysis (C 67H 45N 3): theoretical value C:90.21%, H:5.08%, N:4.71%; Measured value C:90.18%, H:5.01%, N:4.81%.
Synthesizing of embodiment 34 compounds 34
Synthesis step is same as the synthetic of compound 1, just the starting material pentanoic in the first step reaction is changed to 4,4 '-dimethyl pentanoic, starting material in the second step reaction are changed to a bromobenzene ketone to the bromobenzene ketone, starting material carbazole in the four-step reaction is changed to the 3-phenyl carbazole, obtains the faint yellow solid product.
Product MS (m/e): 919; Ultimate analysis (C69H49N3): theoretical value C:90.07%, H:5.36%, N:4.57%; Measured value C:90.03%, H:5.25%, N:4.72%.
The application implementation scheme of compound of the present invention:
The compounds of this invention is used as the embodiment that is prepared with organic electroluminescence devices:
Basic structure in the organic electroluminescence device that the present invention proposes comprises: substrate, pair of electrodes, and be arranged on this to the organic light emitting medium between the electrode, the hole transport functional layer is being set between organic light emitting medium and the anode, the hole transport functional layer is being set between organic light emitting medium and negative electrode respectively.
Matrix is transparent base, can be glass or flexible substrate, and flexible substrate adopts a kind of material in polyester, the polyimide compounds; The first electrode layer (anode layer), can adopt inorganic materials or organic conductive polymkeric substance, inorganic materials is generally the higher metals of work function such as the metal oxides such as ITO, zinc oxide, zinc tin oxide or gold, copper, silver, the optimized ITO that is chosen as, organic conductive polymkeric substance are preferably a kind of material in Polythiophene/polyvinylbenzenesulfonic acid sodium (hereinafter to be referred as PEDOT:PSS), the polyaniline (hereinafter to be referred as PANI); The second electrode lay (cathode layer, metal level), the general alloy that adopts the lower metal of the work functions such as lithium, magnesium, calcium, strontium, aluminium, indium or they and copper, gold and silver, or the electrode layer that alternately forms of metal and metal fluoride, the present invention is preferably Mg:Ag alloy layer, Ag layer and LiF layer successively, Al layer successively.
Organic light emitting medium mainly includes organic electroluminescent layer (EML), and the luminescent layer material can adopt the compound doped phosphorescent coloring in the general formula of the present invention, such as three (2-phenylpyridine) iridium (Ir (ppy) 3), two (2-phenylpyridine) (methyl ethyl diketone) iridium (Ir (ppy) 2(acac)), octaethylporphyrin platinum (PtOEP) etc.;
Can also comprise hole injection layer and hole transmission layer in the above-mentioned device architecture, the substrate material of hole injection layer (HIL) can adopt copper phthalocyanine (CuPc), 4,4 ' 4 " (N-3-aminomethyl phenyl-N-phenyl-amino)-triphenylamine (m-MTDATA), 4-three, 4 ' 4 "-three (N-2-naphthyl-N-phenyl-amino)-triphenylamines (2-TNATA).
The material of hole transmission layer can be selected N, N '-bis-(1-naphthyl)-N, and N '-diphenyl-1,1 '-biphenyl-4,4 '-diamine (NPB), TPD etc. also can select the compound in the general formula of the present invention.
The following making of device of the present invention:
Sheet glass supersound process in commercial clean-out system of ITO transparency conducting layer will be coated with, in deionized water, wash, at acetone: ultrasonic oil removing in the alcohol mixed solvent (volume ratio 1: 1), under clean environment, be baked to and remove moisture content fully, with UV-light and ozone clean, and with low energy positively charged ion bundle bombarded surface;
Above-mentioned glass substrate with anode is placed in the vacuum chamber, be evacuated to 1 * 10 -5To 9 * 10 -3Pa, vacuum evaporation NPB is as hole transmission layer on above-mentioned anode tunic, and evaporation speed is 0.1nm/s, and the evaporation thickness is 40nm; Also can select compound of the present invention as hole transport layer material.
Vacuum evaporation compound of the present invention and contrast evaporation material C BP of the prior art are as the material of main part in the luminescent layer of device on hole transmission layer, and the while is evaporation luminescent dye Ir (ppy) jointly 3(shown in following each device architecture of its weight percent that adds separately), evaporation speed is 0.1nm/s, the evaporation total film thickness is 30nm;
Vacuum evaporation one deck Bphen is the electron transfer layer of device on luminescent layer, and its evaporation speed is 0.1nm/s, and the evaporation total film thickness is 20nm;
The LiF of vacuum evaporation 0.5nm is that the Al layer of 150nm is as the negative electrode of device as electron injecting layer and thickness on electron transfer layer.
The different materials structural formula that uses among the present invention is as follows:
Prepare following each device according to method mentioned above: make it have following structure:
Comparative Examples 1:
ITO/NPB(40nm)/CBP:6％Ir(ppy) 3(30nm)/Bphen(20nm)/LiF(0.5nm)/Al(150nm)
Embodiment 35:
ITO/NPB (40nm)/compound (1): 6%Ir (ppy) 3(30nm)/Bphen (20nm)/LiF (0.5nm)/Al (150nm)
Embodiment 36:
ITO/NPB (40nm)/compound (5): 5%Ir (ppy) 3(30nm)/Bphen (20nm)/LiF (0.5nm)/Al (150nm)
Embodiment 37:
ITO/NPB (40nm)/compound (22): 3%Ir (ppy) 3(30nm)/Bphen (20nm)/LiF (0.5nm)/Al (150nm)
Embodiment 38:
ITO/NPB (40nm)/compound (32): 8%Ir (ppy) 3(30nm)/Bphen (20nm)/LiF (0.5nm)/Al (150nm)
Embodiment 39:
ITO/NPB (40nm)/compound (33): 5%Ir (ppy) 3(30nm)/Bphen (20nm)/LiF (0.5nm)/Al (150nm)
Embodiment 40:
ITO/NPB (40nm)/compound (1) (10nm)/compound (1): 4%Ir (ppy) 3(30nm)/Bphen (20nm)/LiF (0.5nm)/Al (150nm)
Table 1 device performance
Device Brightness cd/m 2 Voltage V Current efficiency cd/A Chromaticity coordinates (x, y)
Comparative Examples 1 1000 3.9 36.2 (0.301，0.640)
Embodiment 35 1000 3.56 42.3 (0.295，0.644)
Embodiment 36 1000 3.61 39.9 (0.297，0.647)
Embodiment 37 1000 3.69 39.6 (0.302，0.641)
Embodiment 38 1000 3.73 39.4 (0.296，0.643)
Embodiment 39 1000 3.61 41.9 (0.298，0.645)
Embodiment 40 1000 3.69 40.6 (0.301，0.645)
Although describe the present invention in conjunction with the embodiments, but the present invention is not limited to above-described embodiment, should be appreciated that under the guiding of the present invention's design, those skilled in the art can carry out various changes and modifications, and these changes and improvements also belong to content of the present invention.

Claims (6)

1. organic materials, its general structure is as follows:
Figure FDA0000096724560000011
Wherein, it is 6 to 30 inferior condensed-nuclei aromatics that R1 to R7 is selected from carbonatoms, or to be selected from carbonatoms be 6 to 30 inferior fused heterocycle aromatic hydrocarbons, or to be selected from carbonatoms be 6 to 20 alkane.
2. according to claim 1 organic materials is characterized in that its general structure is as follows:
Figure FDA0000096724560000012
(2) (3) wherein, it is 6 to 30 inferior condensed-nuclei aromatics that R1 to R7 is selected from carbonatoms, or to be selected from carbonatoms be 6 to 30 inferior fused heterocycle aromatic hydrocarbons, or to be selected from carbonatoms be 6 to 20 alkane.
3. according to claim 1 and 2 organic materials is characterized in that the structure of described general formula compound is:
Figure FDA0000096724560000021
Figure FDA0000096724560000031
Figure FDA0000096724560000041
Figure FDA0000096724560000051
Figure FDA0000096724560000061
4. claim 1 or 2 described organic materialss are used as phosphorescent light body material and hole mobile material in organic electroluminescence device.
5. an organic electroluminescence device wherein comprises pair of electrodes and is arranged on this to the organic light emitting medium between the electrode, comprises at least a kind of material described in the claim 1 that is selected from this organic light emitting medium.
6. device according to claim 5 comprises luminescent layer and hole transport one functional layer in the described organic light emitting medium, wherein comprises at least a material described in the claim 1 that is selected from phosphorescence luminescent layer or the hole transport functional layer.
CN2011103024146A 2011-09-28 2011-09-28 Organic material and organic electroluminescent device adopting organic material Pending CN103030630A (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100019658A1 (en) * 2008-07-22 2010-01-28 Industrial Technology Research Institute Organic compound and organic electroluminescence device employing the same
CN101659638A (en) * 2008-08-26 2010-03-03 财团法人工业技术研究院 Organic compound and organic electroluminescent device containing same
US20100219406A1 (en) * 2007-10-02 2010-09-02 Basf Se Use of acridine derivatives as matrix materials and/or electron blockers in oleds

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100219406A1 (en) * 2007-10-02 2010-09-02 Basf Se Use of acridine derivatives as matrix materials and/or electron blockers in oleds
US20100019658A1 (en) * 2008-07-22 2010-01-28 Industrial Technology Research Institute Organic compound and organic electroluminescence device employing the same
CN101659638A (en) * 2008-08-26 2010-03-03 财团法人工业技术研究院 Organic compound and organic electroluminescent device containing same

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