CN103664995A - Naphthodithiophene derivative organic electroluminescent material and application thereof - Google Patents

Naphthodithiophene derivative organic electroluminescent material and application thereof Download PDF

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CN103664995A
CN103664995A CN201210591543.6A CN201210591543A CN103664995A CN 103664995 A CN103664995 A CN 103664995A CN 201210591543 A CN201210591543 A CN 201210591543A CN 103664995 A CN103664995 A CN 103664995A
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thiophene
naphtho
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CN103664995B (en
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邱勇
李银奎
段炼
任雪艳
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Tsinghua University
Beijing Visionox Technology Co Ltd
Kunshan Visionox Display Co Ltd
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Beijing Visionox Technology Co Ltd
Kunshan Visionox Display Co Ltd
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Abstract

The invention provides novel compounds, of which the structures are represented as Formula (I), Formula (II), Formula (III) and Formula (IV), wherein Ar1-Ar6 are selected from C1-C20 aliphatic alkyl groups, C4-C30 aromatic rings, C4-C30 aromatic heterocyclic rings, C4-C30 condensed heterocyclic ring aromatics, C4-C30 arylamino or triarylamino groups or C4-C30 aryloxy groups. The compounds are used as a hole injection material, hole transmission material or fluorescence body material in organic electroluminescent devices.

Description

Naphtho-two thiophene derivants electroluminescent organic material and application thereof
Technical field
The present invention relates to a kind of novel organic materials, relate in particular to a kind of compound for organic electroluminescence device and preparation method thereof and the application of this compound in ORGANIC ELECTROLUMINESCENCE DISPLAYS technical field.
Background technology
The hole-injecting material and the transport material that in organic electroluminescent device, use are generally derivative of tri-arylamine group (for example bright dipping patents: publication number CN1152607C always, open day 2004,6,2), its general constructional feature is, as hole-injecting material, in a molecule, its three arylamine structural unit has at least more than three, and with a naphthalene nucleus, separates between two N, sees structural formula 1; As hole mobile material, in a molecule, its three arylamine structural unit is generally two, and with dinaphthalene, separates between two N, and typical example is NPB, and its structure is shown in structural formula 2.
Structural formula 1 structural formula 2
In recent years, the research of this class material has had some new progresses, in molecule, introduce one or more thienyls, or introduce one or more aphthothiophenes bases, see structural formula 3 and structural formula 4(bright dipping patent: publication number CN101506191A, open day 2009,8,12), result is the hole injectability that has greatly increased material; As hole mobile material, when three arylamine structural units in material are replaced with carbazole or dinaphtho furans, the cavity transmission ability of material all has a more substantial increase, see structural formula 5 and structural formula 6(bright dipping patent: publication number CN102334210A, the applying date 2012,1,25; Publication number: WO2010/114017A1, open day 2010,10,7).
Figure BDA00002686628100012
Structural formula 3 structural formulas 4
Figure BDA00002686628100021
Structural formula 5 structural formulas 6
The hole-injecting material that said structure formula 1 ~ 6 is represented and the transporting mechanism of hole mobile material are: injection or transmitting procedure in hole, the lone electron pair that N atom in structural formula contains provides an electronics, form hole, because in whole molecule, the energy of the upper lone electron pair of N is the highest, the most easily provides.
Yet if contain thiophene-structure unit in molecule, the lone electron pair on S atom more easily provides electronics, form hole, i.e. easier transmission electronic.Major cause is, S is period 3 element, and the lone electron pair of S atom is in the 3rd layer of track, and N is element second cycle, the lone electron pair of N atom, in second layer track, is compared with N atom, the lone electron pair of S atom is farther from nucleus, is subject to nuclear magnetism more weak; Therefore, the electronics in the lone electron pair of S atom more easily provides, and electronic injection or hole transport are more easily carried out.
Material disclosed in this invention, no matter how substituent structure changes, can guarantee at least to contain two S atoms in molecule, makes material very easily provide electronics and transmits hole.Therefore, hole-injecting material and/or the hole mobile material of exploitation stability and high efficiency, thus reduced bright voltage, improve device efficiency, there is very important actual application value.
Summary of the invention
Of the present invention solved problem is to provide the novel naphtho-of a class two thiophene derivants, can effectively solve the problem that hole mobility is low.
In order to solve the problems of the technologies described above, the invention provides a kind of naphtho-two thiophene derivants, have suc as formula (I), (II), (III) and the structure (IV):
Figure BDA00002686628100022
Figure BDA00002686628100031
Wherein:
Ar1 ~ Ar6 is selected from the aromatic ring of C1 ~ C20 aliphatic alkyl, C4 ~ C30, the virtue of the fragrant heterocycle of C4 ~ C30, C4 ~ C30 is amino or one of three virtue amino, the annelated heterocycles aromatic hydrocarbons of C4 ~ C30 or aryloxy of C4 ~ C30.
Further, described aliphatic alkyl is selected from: the cycloalkyl of C3 ~ C12 or contain ethylene linkage or the alkyl of the C3 ~ C12 of acetylene bond.
Further, described fragrant heterocycle is selected from pyridyl, thienyl, furyl or pyrryl.
Further, the heteroatoms in described annelated heterocycles aromatic hydrocarbons is N, O, S atom.
In order more to clearly demonstrate content of the present invention, the preferred structure in the type of compounds that lower mask body narration the present invention relates to.
Described naphtho-two thiophene derivants, are selected from following structural formula:
Figure BDA00002686628100032
Compound 1
Figure BDA00002686628100041
Compound 2
Figure BDA00002686628100042
Compound 3
Figure BDA00002686628100043
Compound 4
Figure BDA00002686628100044
Compound 5
Figure BDA00002686628100045
Compound 6
Figure BDA00002686628100046
Compound 7
Compound 8
Figure BDA00002686628100048
Compound 9
Figure BDA00002686628100051
Compound 10
Figure BDA00002686628100052
Compound 11
Figure BDA00002686628100053
Compound 12
Figure BDA00002686628100054
Compound 13
Figure BDA00002686628100055
Compound 14
Compound 15
Figure BDA00002686628100061
Compound 16
Figure BDA00002686628100062
Compound 17
Figure BDA00002686628100063
Compound 18
Figure BDA00002686628100064
Compound 19
Figure BDA00002686628100065
Compound 20
Figure BDA00002686628100066
Compound 21
Figure BDA00002686628100071
Compound 22
Figure BDA00002686628100072
Compound 23
Compound 24
Figure BDA00002686628100074
Compound 25
Figure BDA00002686628100075
Compound 26
Compound 27
Figure BDA00002686628100077
Compound 28
Figure BDA00002686628100081
Compound 29
Figure BDA00002686628100082
Compound 30
Figure BDA00002686628100083
Compound 31
Figure BDA00002686628100084
Compound 32
Compound 33
Figure BDA00002686628100086
Compound 34
Compound 35
Figure BDA00002686628100092
Compound 36
Compound 37
Figure BDA00002686628100094
Compound 38
Figure BDA00002686628100095
Compound 39.
Naphtho-two thiophene derivants of the present invention are used as hole-injecting material, hole mobile material or fluorescence material of main part in organic electroluminescence device.
The present invention also provides a kind of organic electroluminescence device, comprises the first electrode and the second electrode and several organic function layers between two electrodes, and wherein, at least one deck in described organic function layer comprises the compound with following structural:
Figure BDA00002686628100101
Wherein:
Ar1 ~ Ar6 is selected from the aromatic ring of C1 ~ C20 aliphatic alkyl, C4 ~ C30, the virtue of the fragrant heterocycle of C4 ~ C30, C4 ~ C30 is amino or one of three virtue amino, the annelated heterocycles aromatic hydrocarbons of C4 ~ C30 or aryloxy of C4 ~ C30.
Naphtho-two thiophene derivants of the present invention have the following advantages:
Naphtho-two thiophene derivants of the present invention have higher hole mobility, can be used as hole and inject or hole mobile material in organic electroluminescence device.
Naphtho-two thiophene derivants of the present invention can be used as fluorescence material of main part in fluorescent device.
Accompanying drawing explanation
For content of the present invention is more likely to be clearly understood, below according to a particular embodiment of the invention and by reference to the accompanying drawings, the present invention is further detailed explanation, wherein
Fig. 1 be compound M1 nuclear magnetic spectrogram ( 13c);
Fig. 2 be compound M9 nuclear magnetic spectrogram ( 13c);
Fig. 3 be compound M20 nuclear magnetic spectrogram ( 13c);
Fig. 4 be compound M26 nuclear magnetic spectrogram ( 13c);
Fig. 5 be compound M32 nuclear magnetic spectrogram ( 13c);
Fig. 6 be compound M39 nuclear magnetic spectrogram ( 13c).
Embodiment
Basic raw material used in the present invention, four kinds of parents, naphtho-[2,3-b:6,7-b '] two thiophene, naphtho-[2,3-b:7,6-b '] two thiophene, naphtho-[1,2-b:5,6-b '] two thiophene, naphtho-[2,1-b:6,5-b '] two thiophene, according to bibliographical information method synthetic (J.Am.Chem.S ℃ of .2011,133,5024 – 5035), other basic chemical industry raw material, has all bought in Chemicals market at home, or customized in the synthetic factory of relevant organic intermediate.
Compou nd synthesis embodiment
Synthesizing of embodiment 1 compound 1
(1) the first step
Figure BDA00002686628100111
Under Ar gas protection, in a dry reactor, add 12.6g(molecular weight 240, naphtho-[2 0.0526mol); 3-b:6,7-b '] two thiophene, 250ml dry THF; be chilled to-80 ℃, under agitation drip t-BuLi(concentration 2.4M, the 0.127mol of 53ml); stir lower nature and be warming up to-10 ℃; and then be once cooled to-50 ℃, drip 35ml(molecular weight 326, proportion 1.20; tributyltin chloride 0.129mol), stirring is spent the night.Second day, by sodium bicarbonate (concentration 0.1M) stopped reaction of 200ml, uses dichloromethane extraction product, with column chromatography separated product (eluent: sherwood oil/triethylamine=95/5), obtain 31g faint yellow solid product, productive rate 71%, molecular weight 818.
(2) second step
Figure BDA00002686628100112
The distannic compound 9.8g(molecular weight 818 that the first step is synthetic, 0.01192mol) with 5-(thiophene-2-yl)-2-bromothiophene 7.1g(molecular weight 245,0.0286mol) be dissolved in the toluene of 400ml, add 2g catalyst P d (PPh3) 4(be bromo-derivative mole number 6%), at 115 ° of C, reflux 24 hours, be chilled to room temperature, steaming desolventizes, with sherwood oil, wash, acetone is washed, and obtains brown solid, then uses the Methods For Purification of vacuum-sublimation, obtain yellow product 6.2g, productive rate 68%.
Product MS(m/e): 568, ultimate analysis (C 30h 16s 6): theoretical value C:63.34%, H:2.82%, S:33.82%; Measured value C:63.41%, H:2.75%, S:33.84%.
Synthesizing of embodiment 2 compounds 2
Figure BDA00002686628100121
Synthesis step is same as the second step in embodiment 1, just by a kind of raw material 5-(thiophene-2-yl wherein)-2-bromothiophene changes into 5-(2-naphthyl)-2-bromothiophene, obtain yellow solid product.
Product MS(m/e): 656, ultimate analysis (C 42h 24s 4): theoretical value C:76.79%, H:3.68%, S:19.53%; Measured value C:76.82%, H:3.73%, S:19.45%.
Synthesizing of embodiment 3 compounds 3
Figure BDA00002686628100122
Synthesis step is same as the second step in embodiment 1, just by a kind of raw material 5-(thiophene-2-yl wherein)-2-bromothiophene changes into 4-(thionaphthene-2-yl) bromobenzene, obtain faint yellow solid product.
Product MS(m/e): 656, ultimate analysis (C 42h 24s 4): theoretical value C:76.79%, H:3.68%, S:19.53%; Measured value C:76.72%, H:3.65%, S:19.63%.
Synthesizing of embodiment 4 compounds 4
Figure BDA00002686628100123
Synthesis step is same as the second step in embodiment 1, just by a kind of raw material 5-(thiophene-2-yl wherein)-2-bromothiophene changes into 4-bromine triphenylamine, obtains faint yellow solid product.
Product MS(m/e): 726, ultimate analysis (C 50h 34n 2s 2): theoretical value C:82.61%, H:4.71%, N:3.85%, S:8.82%; Measured value C:82.58%, H:4.70%, N:3.83%, S:8.89%.
Synthesizing of embodiment 5 compounds 5
Figure BDA00002686628100131
Synthesis step is same as the second step in embodiment 1, just by a kind of raw material 5-(thiophene-2-yl wherein)-2-bromothiophene changes into N-(4-bromophenyl) carbazole, obtain faint yellow solid product.
Product MS(m/e): 722, ultimate analysis (C 50h 30n 2s 2): theoretical value C:83.07%, H:4.18%, N:3.88%, S:8.87%; Measured value C:83.03%, H:4.13%, N:3.91%, S:8.93%.
Synthesizing of embodiment 6 compounds 6
Figure BDA00002686628100132
Synthesis step is same as the second step in embodiment 1, just by a kind of raw material 5-(thiophene-2-yl wherein)-2-bromothiophene changes into N-phenyl-3-bromine carbazole, obtains faint yellow solid product.
Product MS(m/e): 722, ultimate analysis (C 50h 30n 2s 2): theoretical value C:83.07%, H:4.18%, N:3.88%, S:8.87%; Measured value C:83.11%, H:4.21%, N:3.90%, S:8.78%.
Synthesizing of embodiment 7 compounds 7
Figure BDA00002686628100133
Synthesis step is same as the second step in embodiment 1, just by a kind of raw material 5-(thiophene-2-yl wherein)-2-bromothiophene changes into 6-phenyl-3-bromine dibenzothiophene, obtains faint yellow solid product.
Product MS(m/e): 756, ultimate analysis (C 50h 28s 4): theoretical value C:79.33%, H:3.73%, S:16.94%; Measured value C:79.40%, H:3.78%, S:16.82%.
Synthesizing of embodiment 8 compounds 8
Figure BDA00002686628100141
Synthesis step is same as the second step in embodiment 1, just by a kind of raw material 5-(thiophene-2-yl wherein)-2-bromothiophene changes into 6-phenyl-3-bromine diphenylene-oxide, obtains faint yellow solid product.
Product MS(m/e): 724, ultimate analysis (C 50h 28o 2s 2): theoretical value C:82.85%, H:3.89%, O:4.41%, S:8.85%; Measured value C:82.82%, H:3.93%, O:4.46%, S:8.79%.
Synthesizing of embodiment 9 compounds 9
Figure BDA00002686628100142
Synthesis step is same as the second step in embodiment 1, just by a kind of raw material 5-(thiophene-2-yl wherein)-2-bromothiophene changes into 4-bromine phenylbenzene-(1-naphthyl) amine, obtains faint yellow solid product.
Product MS(m/e): 826, ultimate analysis (C 58h 38n 2s 2): theoretical value C:84.23%, H:4.63%, N:3.39%, S:7.75%; Measured value C:84.25%, H:4.60%, N:3.35%, S:7.80%.
Synthesizing of embodiment 10 compounds 10
Figure BDA00002686628100151
Synthesis step is same as the second step in embodiment 1, just by a kind of raw material 5-(thiophene-2-yl wherein)-2-bromothiophene changes into N-phenyl-6-phenyl-3-bromine carbazole, obtains faint yellow solid product.
Product MS(m/e): 874, ultimate analysis (C 62h 38n 2s 2): theoretical value C:85.09%, H:4.38%, N:3.20%, S:7.33%; Measured value C:85.12%, H:4.40%, N:3.25%, S:7.23%.
Synthesizing of embodiment 11 compounds 11
Figure BDA00002686628100152
Synthesis step is same as the second step in embodiment 1, just by a kind of raw material 5-(thiophene-2-yl wherein)-2-bromothiophene changes into 1-(4-bromophenyl)-2-Phenylbenzimidazole, obtains faint yellow solid product.
Product MS(m/e): 776, ultimate analysis (C 52h 32n 4s 2): theoretical value C:80.38%, H:4.15%, N:7.21%, S:8.25%; Measured value C:80.40%, H:4.18%, N:7.24%, S:8.18%.
Synthesizing of embodiment 12 compounds 12
Synthesis step is same as the second step in embodiment 1, just by a kind of raw material 5-(thiophene-2-yl wherein)-2-bromothiophene changes into 1-phenyl-2-(4-bromophenyl) benzoglyoxaline, obtains faint yellow solid product.
Product MS(m/e): 776, ultimate analysis (C 52h 32n 4s 2): theoretical value C:80.38%, H:4.15%, N:7.21%, S:8.25%; Measured value C:80.33%, H:4.13%, N:7.26%, S:8.28%.
Synthesizing of embodiment 13 compounds 13
Figure BDA00002686628100162
Synthesis step is same as the second step in embodiment 1, just by a kind of raw material 5-(thiophene-2-yl wherein)-2-bromothiophene changes into 2-phenyl-5-bromopyridine, obtains faint yellow solid product.
Product MS(m/e): 546, ultimate analysis (C 36h 22n 2s 2): theoretical value C:79.09%, H:4.06%, N:5.12%, S:11.73%; Measured value C:79.12%, H:4.06%, N:5.16%, S:11.66%.
Synthesizing of embodiment 14 compounds 14
Figure BDA00002686628100163
Synthesis step is same as the second step in embodiment 1, just by a kind of raw material 5-(thiophene-2-yl wherein)-2-bromothiophene changes into 2,3-phenylbenzene-6-bromine imidazo (1,2a) pyridine, obtains faint yellow solid product.
Product MS(m/e): 776, ultimate analysis (C 52h 32n 4s 2): theoretical value C:80.38%, H:4.15%, N:7.21%, S:8.25%; Measured value C:80.36%, H:4.19%, N:7.16%, S:8.29%.
Synthesizing of embodiment 15 compounds 15
Figure BDA00002686628100171
Synthesis step is same as the second step in embodiment 1, just by a kind of raw material 5-(thiophene-2-yl wherein)-2-bromothiophene changes into 5-bromine benzophenanthrene, obtains faint yellow solid product.
Product MS(m/e): 692, ultimate analysis (C 50h 28s 2): theoretical value C:86.67%, H:4.07%, S:9.26%; Measured value C:86.70%, H:4.11%, S:9.19%.
Synthesizing of embodiment 16 compounds 16
Figure BDA00002686628100172
Synthesis step is same as the second step in embodiment 1, just by a kind of raw material 5-(thiophene-2-yl wherein)-2-bromothiophene changes into 10-(2-naphthyl)-9-bromine anthracene, obtain faint yellow solid product.
Product MS(m/e): 844, ultimate analysis (C 62h 36s 2): theoretical value C:88.12%, H:4.29%, S:7.59%; Measured value C:88.16%, H:4.31%, S:7.53%.
Synthesizing of embodiment 17 compounds 17
Figure BDA00002686628100173
Synthesis step is same as embodiment 1, just by the raw material naphtho-[2 in the first step, 3-b:6,7-b '] two thiophene change into naphtho-[2,3-b:7,6-b '] two thiophene, the raw material 5-(thiophene-2-yl in second step)-2-bromothiophene changes into 1-(4-bromophenyl)-2-Phenylbenzimidazole, obtains faint yellow solid product.
Product MS(m/e): 776, ultimate analysis (C 52h 32n 4s 2): theoretical value C:80.38%, H:4.15%, N:7.22%, S:8.25%; Measured value C:80.34%, H:4.16%, N:7.24%, S:8.26%.
Synthesizing of embodiment 18 compounds 18
Figure BDA00002686628100181
Synthesis step is same as embodiment 1, just by the raw material naphtho-[2 in the first step, 3-b:6,7-b '] two thiophene change into naphtho-[2,3-b:7,6-b '] two thiophene, raw material 5-(thiophene-2-yl in second step)-2-bromothiophene changes into 2, (1,2-a) pyridine, obtains faint yellow solid product to 3-phenylbenzene-6-bromine imidazo.
Product MS(m/e): 776, ultimate analysis (C 52h 32n 4s 2): theoretical value C:80.38%, H:4.15%, N:7.22%, S:8.25%; Measured value C:80.34%, H:4.16%, N:7.24%, S:8.26%.
Synthesizing of embodiment 19 compounds 19
Figure BDA00002686628100182
Synthesis step is same as embodiment 1, just by raw material naphtho-[2, the 3-b:6 in the first step, 7-b '] two thiophene change into naphtho-[2,3-b:7,6-b '] two thiophene, raw material 5-(thiophene-2-yl in second step)-2-bromothiophene is changed into 4 bromine triphenylamines, obtains faint yellow solid product.
Product MS(m/e): 726, ultimate analysis (C 50h 34n 2s 2): theoretical value C:82.61%, H:4.71%, N:3.85%, S:8.82%; Measured value C:82.65%, H:4.67%, N:3.88%, S:8.80%.
Synthesizing of embodiment 20 compounds 20
Figure BDA00002686628100191
Synthesis step is same as embodiment 1, just by the raw material naphtho-[2 in the first step, 3-b:6,7-b '] two thiophene change into naphtho-[2,3-b:7,6-b '] two thiophene, the raw material 5-(thiophene-2-yl in second step)-2-bromothiophene changes into 4 bromine phenylbenzene-(1-naphthyl) amine, obtains faint yellow solid product.
Product MS(m/e): 826, ultimate analysis (C 58h 38n 2s 2): theoretical value C:84.23%, H:4.63%, N:3.39%, S:7.75%; Measured value C:84.20%, H:4.67%, N:3.42%, S:7.71%.
Synthesizing of embodiment 21 compounds 21
Figure BDA00002686628100192
Synthesis step is same as embodiment 1, just by the raw material naphtho-[2 in the first step, 3-b:6,7-b '] two thiophene change into naphtho-[2,3-b:7,6-b '] two thiophene, the raw material 5-(thiophene-2-yl in second step)-2-bromothiophene changes into N-(4-bromophenyl) carbazole, obtain faint yellow solid product.
Product MS(m/e): 722, ultimate analysis (C 50h 30n 2s 2): theoretical value C:83.07%, H:4.18%, N:3.88%, S:8.87%; Measured value C:83.11%, H:4.23%, N:3.85%, S:8.81%.
Synthesizing of embodiment 22 compounds 22
Figure BDA00002686628100201
Synthesis step is same as embodiment 1, just by the raw material naphtho-[2 in the first step, 3-b:6,7-b '] two thiophene change into naphtho-[2,3-b:7,6-b '] two thiophene, the raw material 5-(thiophene-2-yl in second step)-2-bromothiophene changes into N-phenyl-6-phenyl-3-bromine carbazole, obtains faint yellow solid product.
Product MS(m/e): 874, ultimate analysis (C 62h 38n 2s 2): theoretical value C:85.09%, H:4.38%, N:3.20%, S:7.33%; Measured value C:85.12%, H:4.33%, N:3.17%, S:7.38%.
Synthesizing of embodiment 23 compounds 23
Figure BDA00002686628100202
Synthesis step is same as embodiment 1, just by the raw material naphtho-[2 in the first step, 3-b:6,7-b '] two thiophene change into naphtho-[2,3-b:7,6-b '] two thiophene, the raw material 5-(thiophene-2-yl in second step)-2-bromothiophene changes into 10(2-naphthyl)-9-bromine anthracene, obtain faint yellow solid product.
Product MS(m/e): 844, ultimate analysis (C 62h 36s 2): theoretical value C:88.12%, H:4.29%, S:7.59%; Measured value C:88.13%, H:4.25%, S:7.62%.
Synthesizing of embodiment 24 compounds 24
Figure BDA00002686628100203
Synthesis step is same as embodiment 1, just by raw material naphtho-[2, the 3-b:6 in the first step, 7-b '] two thiophene change into naphtho-[2,3-b:7,6-b '] two thiophene, raw material 5-(thiophene-2-yl in second step)-2-bromothiophene is changed into 5 bromine benzophenanthrenes, obtains faint yellow solid product.
Product MS(m/e): 692, ultimate analysis (C 50h 28s 2): theoretical value C:86.67%, H:4.07%, S:9.26%; Measured value C:86.71%, H:4.05%, S:9.24%.
Synthesizing of embodiment 25 compounds 25
Figure BDA00002686628100211
Synthesis step is same as embodiment 1, just by the raw material naphtho-[2 in the first step, 3-b:6,7-b '] two thiophene change into naphtho-[2,3-b:7,6-b '] two thiophene, the raw material 5-(thiophene-2-yl in second step)-2-bromothiophene changes into 6 phenyl-3-bromine dibenzothiophene, obtains faint yellow solid product.
Product MS(m/e): 756, ultimate analysis (C 50h 28s 4): theoretical value C:79.33%, H:3.73%, S:16.94%; Measured value C:79.35%, H:3.76%, S:16.89%.
Synthesizing of embodiment 26 compounds 26
Synthesis step is same as embodiment 1, just by the raw material naphtho-[2 in the first step, 3-b:6,7-b '] two thiophene change into naphtho-[2,3-b:7,6-b '] two thiophene, the raw material 5-(thiophene-2-yl in second step)-2-bromothiophene changes into 6 phenyl-3-bromine diphenylene-oxide, obtains faint yellow solid product.
Product MS(m/e): 724, ultimate analysis (C 50h 28o 2s 2): theoretical value C:82.85%, H:3.89%, O:4.41%, S:8.85%; Measured value C:82.90%, H:3.85%, O:4.45%, S:8.80%.
Synthesizing of embodiment 27 compounds 27
Figure BDA00002686628100221
Synthesis step is same as embodiment 1, just by raw material naphtho-[2, the 3-b:6 in the first step, 7-b '] two thiophene change into naphtho-[1,2-b:5,6-b '] two thiophene, raw material 5-(thiophene-2-yl in second step)-2-bromothiophene is changed into 10 phenyl-9-bromine anthracene, obtains faint yellow solid product.
Product MS(m/e): 744, ultimate analysis (C 54h 32s 2): theoretical value C:87.06%, H:4.33%, S:8.61%; Measured value C:87.11%, H:4.29%, S:8.60%.
Synthesizing of embodiment 28 compounds 28
Synthesis step is same as embodiment 1, just by the raw material naphtho-[2 in the first step, 3-b:6,7-b '] two thiophene change into naphtho-[1,2-b:5,6-b '] two thiophene, the raw material 5-(thiophene-2-yl in second step)-2-bromothiophene changes into N-phenyl-6-phenyl-3-bromine carbazole, obtains faint yellow solid product.
Product MS(m/e): 874, ultimate analysis (C 62h 38n 2s 2): theoretical value C:85.09%, H:4.38%, N:3.20%, S:7.33%; Measured value C:85.14%, H:4.40%, N:3.18%, S:7.28%.
Synthesizing of embodiment 29 compounds 29
Figure BDA00002686628100231
Synthesis step is same as embodiment 1, just by raw material naphtho-[2, the 3-b:6 in the first step, 7-b '] two thiophene change into naphtho-[1,2-b:5,6-b '] two thiophene, raw material 5-(thiophene-2-yl in second step)-2-bromothiophene is changed into 4-bromine triphenylamine, obtains faint yellow solid product.
Product MS(m/e): 726, ultimate analysis (C 50h 34n 2s 2): theoretical value C:82.61%, H:4.71%, N:3.85%, S:8.82%; Measured value C:82.65%, H:4.75%, N:3.80%, S:8.80%.
Synthesizing of embodiment 30 compounds 30
Figure BDA00002686628100232
Synthesis step is same as embodiment 1, just by the raw material naphtho-[2 in the first step, 3-b:6,7-b '] two thiophene change into naphtho-[1,2-b:5,6-b '] two thiophene, the raw material 5-(thiophene-2-yl in second step)-2-bromothiophene changes into 4-bromine phenylbenzene-(1-naphthyl) amine, obtains faint yellow solid product.
Product MS(m/e): 826, ultimate analysis (C 58h 38n 2s 2): theoretical value C:84.23%, H:4.63%, N:3.39%, S:7.75%; Measured value C:8425%, H:4.67%, N:3.36%, S:7.72%.
Synthesizing of embodiment 31 compounds 31
Figure BDA00002686628100241
Synthesis step is same as embodiment 1, just by the raw material naphtho-[2 in the first step, 3-b:6,7-b '] two thiophene change into naphtho-[1,2-b:5,6-b '] two thiophene, the raw material 5-(thiophene-2-yl in second step)-2-bromothiophene changes into N-(4-bromophenyl) carbazole, obtain faint yellow solid product.
Product MS(m/e): 722, ultimate analysis (C 50h 30n 2s 2): theoretical value C:83.07%, H:4.18%, N:3.88%, S:8.87%; Measured value C:83.05%, H:4.20%, N:3.90%, S:8.85%.
Synthesizing of embodiment 32 compounds 32
Figure BDA00002686628100242
Synthesis step is same as embodiment 1, just by the raw material naphtho-[2 in the first step, 3-b:6,7-b '] two thiophene change into naphtho-[1,2-b:5,6-b '] two thiophene, the raw material 5-(thiophene-2-yl in second step)-2-bromothiophene changes into N-phenyl-6-phenyl-3-bromine carbazole, obtains faint yellow solid product.
Product MS(m/e): 874, ultimate analysis (C 62h 38n 2s 2): theoretical value C:85.09%, H:4.38%, N:3.20%, S:7.33%; Measured value C:85.05%, H:4.40%, N:3.23%, S:7.32%.
Synthesizing of embodiment 33 compounds 33
Synthesis step is same as embodiment 1, just by the raw material naphtho-[2 in the first step, 3-b:6,7-b '] two thiophene change into naphtho-[1,2-b:5,6-b '] two thiophene, the raw material 5-(thiophene-2-yl in second step)-2-bromothiophene changes into 6 phenyl-3-bromine dibenzothiophene, obtains faint yellow solid product.
Product MS(m/e): 756, ultimate analysis (C 50h 28s 4): theoretical value C:79.33%, H:3.73%, S:16.94%; Measured value C:79.27%, H:3.76%, S:16.97%.
Synthesizing of embodiment 34 compounds 34
Figure BDA00002686628100251
Synthesis step is same as embodiment 1, just by the raw material naphtho-[2 in the first step, 3-b:6,7-b '] two thiophene change into naphtho-[1,2-b:5,6-b '] two thiophene, the raw material 5-(thiophene-2-yl in second step)-2-bromothiophene changes into 6 phenyl-3-bromine diphenylene-oxide, obtains faint yellow solid product.
Product MS(m/e): 724, ultimate analysis (C 50h 28o 2s 2): theoretical value C:82.85%, H:3.89%, O:4.41%, S:8.85%; Measured value C:82.83%, H:3.85%, O:4.45%, S:8.87%.
Synthesizing of embodiment 35 compounds 35
Figure BDA00002686628100252
Synthesis step is same as embodiment 1, just by the raw material naphtho-[2 in the first step, 3-b:6,7-b '] two thiophene change into naphtho-[2,1-b:6,5-b '] two thiophene, the raw material 5-(thiophene-2-yl in second step)-2-bromothiophene changes into 6 phenyl-3-bromine dibenzothiophene, obtains faint yellow solid product.
Product MS(m/e): 756, ultimate analysis (C 50h 28s 4): theoretical value C:79.33%, H:3.73%, S:16.94%; Measured value C:79.29%, H:3.76%, S:16.95%.
Synthesizing of embodiment 36 compounds 36
Figure BDA00002686628100261
Synthesis step is same as embodiment 1, just by the raw material naphtho-[2 in the first step, 3-b:6,7-b '] two thiophene change into naphtho-[2,1-b:6,5-b '] two thiophene, the raw material 5-(thiophene-2-yl in second step)-2-bromothiophene changes into 6-phenyl-3-bromine diphenylene-oxide, obtains faint yellow solid product.
Product MS(m/e): 724, ultimate analysis (C 50h 28o 2s 2): theoretical value C:82.85%, H:3.89%, O:4.41%, S:8.85%; Measured value C:82.82%, H:3.90%, O:4.44%, S:8.84%.
Synthesizing of embodiment 37 compounds 37
Figure BDA00002686628100262
Synthesis step is same as embodiment 1, just by the raw material naphtho-[2 in the first step, 3-b:6,7-b '] two thiophene change into naphtho-[2,1-b:6,5-b '] two thiophene, the raw material 5-(thiophene-2-yl in second step)-2-bromothiophene changes into 4-bromine phenylbenzene-(1-naphthyl) amine, obtains faint yellow solid product.
Product MS(m/e): 826, ultimate analysis (C 58h 38n 2s 2): theoretical value C:84.23%, H:4.63%, N:3.39%, S:7.75%; Measured value C:84.27%, H:4.60%, N:3.35%, S:7.78%.
Synthesizing of embodiment 38 compounds 38
Synthesis step is same as embodiment 1, just by the raw material naphtho-[2 in the first step, 3-b:6,7-b '] two thiophene change into naphtho-[2,1-b:6,5-b '] two thiophene, the raw material 5-(thiophene-2-yl in second step)-2-bromothiophene changes into N-phenyl-6-phenyl-3-bromine carbazole, obtains faint yellow solid product.
Product MS(m/e): 874, ultimate analysis (C 62h 38n 2s 2): theoretical value C:85.09%, H:4.38%, N:3.20%, S:7.33%; Measured value C:85.07%, H:4.42%, N:3.24%, S:7.27%.
Synthesizing of embodiment 39 compounds 39
Figure BDA00002686628100271
Synthesis step is same as embodiment 1, just by raw material naphtho-[2, the 3-b:6 in the first step, 7-b '] two thiophene change into naphtho-[2,1-b:6,5-b '] two thiophene, raw material 5-(thiophene-2-yl in second step)-2-bromothiophene is changed into 10 phenyl-9-bromine anthracene, obtains faint yellow solid product.
Product MS(m/e): 744, ultimate analysis (C 54h 32s 2): theoretical value C:87.06%, H:4.33%, S:8.61%; Measured value C:87.12%, H:4.30%, S:8.58%.
The Application Example of the compounds of this invention below:
Embodiment 40: fabricate devices OLED-1 ~ OLED-10
The preferred implementation of fabricate devices:
(1) device design
For convenient relatively these holes are injected, the performance of transport material, the present invention has designed a simple electroluminescence device (substrate/anode/hole injection layer (HIL)/hole transmission layer (HTL)/organic luminous layer (EL)/electron transfer layer (ETL)/negative electrode), only uses compound 1,7,9,10,16,20,22,28,30,37 as hole injection, transport material illustration, and efficient hole-injecting material 2-TNATA is material as a comparison, and TBPe is as luminescent layer material in ADN doping.The structure of 2-TNATA, NPB, AND and TBPe is:
Figure BDA00002686628100272
Figure BDA00002686628100281
Substrate can be used the substrate in traditional organic luminescent device, for example: glass or plastics.In element manufacturing of the present invention, select glass substrate, ITO makes anode material.
Hole transmission layer can adopt various tri-arylamine group materials.In element manufacturing of the present invention, selected hole mobile material is NPB.
Negative electrode can adopt metal and composition thereof structure, as Mg:Ag, Ca:Ag etc., can be also electron injecting layer/metal-layer structure, as LiF/Al, Li 2the common cathode construction such as O.In element manufacturing of the present invention, selected electron injection material is LiF, and cathode material is Al.
(2) make device OLED-1
Sheet glass supersound process in commercial clean-out system of ITO transparency conducting layer will be coated with; in deionized water, rinse, at acetone: ultrasonic oil removing in alcohol mixed solvent is baked to and removes moisture content completely under clean environment; by UV-light and ozone clean, and with low energy positively charged ion bundle bombarded surface;
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 * 10 -5～9 * 10 -3pa, the material 1,7,9,10,16,20,22,28 on above-mentioned anode tunic in vacuum evaporation this patent, 30,37,39 as hole injection layer, and evaporation speed is 0.1nm/s, and evaporation thickness is 80nm;
Then on hole injection layer material, evaporation one deck NPB is as hole transmission layer again, and evaporation speed is 0.1nm/s, and evaporation thickness is 20nm;
Vacuum evaporation luminescent layer on hole transmission layer, the method for steaming altogether with double source, evaporation ADN and TBPe, the evaporation speed of ADN is 0.1nm/s, and the evaporation speed of TBPe is 0.005nm/s, and evaporation total film thickness is 30nm;
On luminescent layer, vacuum evaporation one deck AlQ3 is as electron transport material respectively, and its evaporation speed is 0.1nm/s,
Evaporation total film thickness is 20nm;
On electron transfer layer (ETL), vacuum evaporation LiF and Al layer are as the negative electrode of device, and thickness is respectively 0.5nm and 150nm.
Preparation preparation OLED-2 ~ OLED-10, is only the compound having changed as hole-injecting material as stated above.
Comparative example 1
Method, with embodiment 40, changes HIL material into 2-TNATA.
Device performance is in Table 1(normal component structure: ITO/ hole-injecting material (80nm)/NPB(20nm)/ADN:5%wtTBPe (30nm)/Alq3(20nm)/LiF(0.5nm)/Al(150nm)).
Table 1
Figure BDA00002686628100291
Embodiment 41: fabricate devices OLED-11, OLED-12 and OLED-13
Method, with embodiment 40, changes HIL material into compound 34, and changes HIL thickness.The performance of device is in Table 2:
Table 2
Embodiment 42: fabricate devices OLED-14, OLED-15 and OLED-16
Method, with embodiment 40, changes HIL material into 2-TNATA, and fluorescence material of main part is selected compound 11,26 and 32.
The performance of device is in Table 3:(normal component structure: ITO/2-TNATA(80nm)/NPB(20nm)/fluorescence main body: 5%wt TBPe (30nm)/Alq3(20nm)/LiF(0.5nm)/Al(150nm))
Table 3
Figure BDA00002686628100301
Above result shows, novel organic materials of the present invention, for organic electroluminescence device, can effectively reduce landing voltage, improves current efficiency, is well behaved hole-injecting material.
Although describe the present invention in conjunction with the embodiments, the present invention is not limited to above-described embodiment, should be appreciated that those skilled in the art can carry out various modifications and improvement under the guiding of the present invention's design, and claims have been summarized scope of the present invention.

Claims (7)

1. naphtho-two thiophene derivants, is characterized in that, have suc as formula (I), (II), (III) and the structure (IV):
Figure FDA00002686628000011
Wherein:
Ar1 ~ Ar6 is selected from the aromatic ring of C1 ~ C20 aliphatic alkyl, C4 ~ C30, the virtue of the fragrant heterocycle of C4 ~ C30, C4 ~ C30 is amino or one of three virtue amino, the annelated heterocycles aromatic hydrocarbons of C4 ~ C30 or aryloxy of C4 ~ C30.
2. naphtho-two thiophene derivants according to claim 1, is characterized in that, described aliphatic alkyl is selected from: the cycloalkyl of C3 ~ C12 or contain ethylene linkage or the alkyl of the C3 ~ C12 of acetylene bond.
3. naphtho-two thiophene derivants according to claim 1, is characterized in that, described fragrant heterocycle is selected from pyridyl, thienyl, furyl or pyrryl.
4. naphtho-two thiophene derivants according to claim 1, is characterized in that, the heteroatoms in described annelated heterocycles aromatic hydrocarbons is N, O or S atom.
5. according to arbitrary described naphtho-two thiophene derivants of claim 1-4, described structural formula of compound is as follows:
Figure FDA00002686628000021
Compound 1
Compound 2
Figure FDA00002686628000023
Compound 3
Figure FDA00002686628000024
Compound 4
Compound 5
Figure FDA00002686628000026
Compound 6
Figure FDA00002686628000027
Compound 7
Figure FDA00002686628000031
Compound 8
Compound 9
Compound 10
Figure FDA00002686628000034
Compound 11
Figure FDA00002686628000035
Compound 12
Figure FDA00002686628000036
Compound 13
Compound 14
Figure FDA00002686628000041
Compound 15
Figure FDA00002686628000042
Compound 16
Figure FDA00002686628000043
Compound 17
Figure FDA00002686628000044
Compound 18
Figure FDA00002686628000045
Compound 19
Figure FDA00002686628000046
Compound 20
Compound 21
Compound 22
Figure FDA00002686628000053
Compound 23
Figure FDA00002686628000054
Compound 24
Compound 25
Figure FDA00002686628000056
Compound 26
Figure FDA00002686628000057
Compound 27
Figure FDA00002686628000061
Compound 28
Figure FDA00002686628000062
Compound 29
Figure FDA00002686628000063
Compound 30
Figure FDA00002686628000064
Compound 31
Figure FDA00002686628000065
Compound 32
Figure FDA00002686628000071
Compound 33
Compound 34
Figure FDA00002686628000073
Compound 35
Figure FDA00002686628000074
Compound 36
Compound 37
Figure FDA00002686628000076
Compound 38
Compound 39.
6. naphtho-two thiophene derivants claimed in claim 1 are used as hole-injecting material, hole mobile material or fluorescence material of main part in organic electroluminescence device.
7. an organic electroluminescence device, comprises the first electrode and the second electrode and several organic function layers between two electrodes, it is characterized in that, at least one deck in organic function layer comprises the compound with following structural:
Figure FDA00002686628000082
Figure FDA00002686628000091
Wherein:
Ar1 ~ Ar6 be selected from the aromatic ring of C1 ~ C20 aliphatic alkyl, C4 ~ C30, the annelated heterocycles aromatic hydrocarbons of the fragrant heterocycle of C4 ~ C30, C4 ~ C30, the virtue of C4 ~ C30 is amino or three virtues are amino or one of aryloxy of C4 ~ C30.
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