CN103664995B - Naphtho-two thiophene derivants electroluminescent organic material and application thereof - Google Patents

Naphtho-two thiophene derivants electroluminescent organic material and application thereof Download PDF

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CN103664995B
CN103664995B CN201210591543.6A CN201210591543A CN103664995B CN 103664995 B CN103664995 B CN 103664995B CN 201210591543 A CN201210591543 A CN 201210591543A CN 103664995 B CN103664995 B CN 103664995B
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thiophene
compound
naphtho
synthesis
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CN103664995A (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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    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

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Abstract

The invention provides a kind of new compound, its structure formula (I), (II), (III) and (IV) represent.Wherein Ar1Ar6 is selected from C1 ~ C20 aliphatic alkyl, the aromatic ring of C4 ~ C30, the heteroaromatic of C4 ~ C30, the annelated heterocycles aromatic hydrocarbons of C4 ~ C30, the fragrant amino of C4 ~ C30 or three virtue amino or the aryloxy group of C4 ~ C30.This compounds is used as hole-injecting material, hole mobile material or fluorescent host material in organic electroluminescence device.

Description

Naphtho-two thiophene derivants electroluminescent organic material and application thereof
Technical field
The present invention relates to a kind of new organic materials, particularly relate to a kind of compound for organic electroluminescence device and Its preparation method and the application in ORGANIC ELECTROLUMINESCENCE DISPLAYS technical field of this compound.
Background technology
The hole-injecting material always used in organic electroluminescent device and transmission material are usually tri-arylamine group and derive Thing (such as go out light patent: publication number CN1152607C, publication date 2004,6,2), its general being structurally characterized in that, as hole Injection material, in a molecule, its tertiary aromatic amine structure unit at least more than three, and separate with a naphthalene nucleus between two N, See structural formula 1；As hole mobile material, in a molecule, its tertiary aromatic amine structure unit is usually two, and between two N Separating with dinaphthalene, 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 kind of material has had some new progresses, introduces one or more thienyl in the molecule, or Person introduces one or more aphthothiophenes base, sees that structural formula 3 and structural formula 4(go out light patent: publication number CN101506191A, public Open day 2009,8,12), result is to considerably increase the Hole injection capacity of material；As hole mobile material, when by material A tertiary aromatic amine structure unit carbazole or dinaphtho furan when replacing, the cavity transmission ability of material has and carries by a relatively large margin Height, is shown in that structural formula 5 and structural formula 6(go out light patent: publication number CN102334210A, the applying date 2012,1,25；Publication number: WO2010/114017A1, publication date 2010,10,7).
Structural formula 3 structural formula 4
Structural formula 5 structural formula 6
Hole-injecting material and the transporting mechanism of hole mobile material represented by structure above 1 ~ 6 be: in hole Injecting or in transmitting procedure, the lone electron pair that the atom N in structural formula contains provides an electronics, forms hole, because whole In individual molecule, the energy of the upper lone electron pair of N is the highest, is the most easily given.
But, if containing thiophene-structure unit in molecule, the lone electron pair on S atom is more easy to provide electronics, forms hole, I.e. it is more easy to transmit electronics.Main cause is, S is period 3 element, and the lone electron pair of S atom is in third layer track, and N is Second round element, the lone electron pair of atom N is in second layer track, and compared with atom N, the lone electron pair of S atom is from atom Core is farther, more weak by nuclear captivation；Therefore, the electronics in the lone electron pair of S atom is more easy to be given so that electronics injects Or hole transport is more easy to carry out.
Material disclosed in this invention, no matter how substituent structure changes, can guarantee at least to contain two S in molecule Atom so that material easily provides electronics and transmission hole.Therefore, hole-injecting material and/or the hole of stability and high efficiency are developed Transmission material, thus reduced bright voltage, improve device efficiency, there is critically important actual application value.
Summary of the invention
The problem solved of the present invention is to provide a class novel naphtho-two thiophene derivants, can effectively solve sky The problem that cave mobility is low.
In order to solve above-mentioned technical problem, the invention provides a kind of naphtho-two thiophene derivant, have as formula (I), (II), the structure shown in (III) and (IV):
Wherein:
Ar1 ~ Ar6 is selected from C1 ~ C20 aliphatic alkyl, the aromatic ring of C4 ~ C30, the heteroaromatic of C4 ~ C30, the fragrant ammonia of C4 ~ C30 One of aryloxy group of base or three virtue amino, the annelated heterocycles aromatic hydrocarbons of C4 ~ C30 or C4 ~ C30.
Further, described aliphatic alkyl is selected from: the cycloalkyl of C3 ~ C12 or containing ethylene linkage or the C3 ~ C12 of acetylene bond Alkyl.
Further, described heteroaromatic is selected from pyridine radicals, thienyl, furyl or pyrrole radicals.
Further, the hetero atom in described annelated heterocycles aromatic hydrocarbons is N, O, S atom.
In order to become apparent from that present invention is described, describe in the type of compounds that the present invention relates in detail below is preferred Structure.
Described naphtho-two thiophene derivant, selected from following structural formula:
Compound 1
Compound 2
Compound 3
Compound 4
Compound 5
Compound 6
Compound 7
Compound 8
Compound 9
Compound 10
Compound 11
Compound 12
Compound 13
Compound 14
Compound 15
Compound 16
Compound 17
Compound 18
Compound 19
Compound 20
Compound 21
Compound 22
Compound 23
Compound 24
Compound 25
Compound 26
Compound 27
Compound 28
Compound 29
Compound 30
Compound 31
Compound 32
Compound 33
Compound 34
Compound 35
Compound 36
Compound 37
Compound 38
Compound 39.
Naphtho-two thiophene derivant of the present invention is used as hole-injecting material, hole in organic electroluminescence device Transmission material or fluorescent host material.
Present invention also offers a kind of organic electroluminescence device, including the first electrode and the second electrode and be positioned at two Several organic function layers between electrode, wherein, at least one of which in described organic function layer comprises and has following structural Compound:
Wherein:
Ar1 ~ Ar6 is selected from C1 ~ C20 aliphatic alkyl, the aromatic ring of C4 ~ C30, the heteroaromatic of C4 ~ C30, the fragrant ammonia of C4 ~ C30 One of aryloxy group of base or three virtue amino, the annelated heterocycles aromatic hydrocarbons of C4 ~ C30 or C4 ~ C30.
Naphtho-two thiophene derivant of the present invention has the advantage that
Naphtho-two thiophene derivant of the present invention has higher hole mobility, available in organic electroluminescence device Make hole to inject or hole mobile material.
Naphtho-two thiophene derivant of the present invention, can be used as fluorescent host material in fluorescent device.
Accompanying drawing explanation
In order to make present disclosure be more likely to be clearly understood, below according to the specific embodiment of the present invention and combine Accompanying drawing, 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).
Detailed description of the invention
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 are according to document Report method synthesis (J.Am.Chem.S DEG C of .2011,133,5,024 5035), other basic chemical industry raw material, all can change at home Chemical product is commercially available, or it is customized to synthesize factory at relevant organic intermediate.
Compou nd synthesis embodiment
The synthesis of embodiment 1 compound 1
(1) first step
Under Ar gas shielded, one be dried reactor in add 12.6g(molecular weight 240,0.0526mol) naphtho-[2, 3-b:6,7-b '] two thiophene, 250ml dry THF, it is cooled to-80 DEG C, under agitation drips t-BuLi(concentration 2.4M of 53ml, 0.127mol), under stirring, warm naturally to-10 DEG C, be cooled to-50 DEG C the most again, drip 35ml(molecular weight 326, proportion 1.20,0.129mol) tributyltin chloride, is stirred overnight.Second day, stop with the sodium bicarbonate (concentration 0.1M) of 200ml Reaction, uses dichloromethane extraction product, with pillar layer separation product (eluent: petroleum ether/triethylamine=95/5), obtains 31g light Yellow solid product, productivity 71%, molecular weight 818.
(2) second step
The distannic compound 9.8g(molecular weight 818,0.01192mol of first step synthesis) and 5-(thiophene-2-base)-2-bromine Thiophene 7.1g(molecular weight 245,0.0286mol) it is dissolved in the toluene of 400ml, adding 2g catalyst Pd (PPh3) 4(is bromo The 6% of thing molal quantity), reflux 24 hours at 115 ° of C, be cooled to room temperature, solvent is evaporated off, wash with petroleum ether, acetone is washed, and obtains brown Solid, then with the Methods For Purification of vacuum sublimation, obtains yellow product 6.2g, productivity 68%.
Product MS(m/e): 568, elementary analysis (C30H16S6): theoretical value C:63.34%, H:2.82%, S:33.82%； Measured value C:63.41%, H:2.75%, S:33.84%.
The synthesis of embodiment 2 compound 2
Synthesis step is same as the second step in embodiment 1, simply by a kind of raw material 5-(thiophene-2-base therein)-2-bromine Thiophene changes into 5-(2-naphthyl)-2-bromothiophene, obtain yellow solid product.
Product MS(m/e): 656, elementary analysis (C42H24S4): theoretical value C:76.79%, H:3.68%, S:19.53%； Measured value C:76.82%, H:3.73%, S:19.45%.
The synthesis of embodiment 3 compound 3
Synthesis step is same as the second step in embodiment 1, simply by a kind of raw material 5-(thiophene-2-base therein)-2-bromine Thiophene changes into 4-(benzothiophene-2-base) bromobenzene, obtain faint yellow solid product.
Product MS(m/e): 656, elementary analysis (C42H24S4): theoretical value C:76.79%, H:3.68%, S:19.53%； Measured value C:76.72%, H:3.65%, S:19.63%.
The synthesis of embodiment 4 compound 4
Synthesis step is same as the second step in embodiment 1, simply by a kind of raw material 5-(thiophene-2-base therein)-2-bromine Thiophene changes into 4-bromine triphenylamine, obtains faint yellow solid product.
Product MS(m/e): 726, elementary analysis (C50H34N2S2): 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%.
The synthesis of embodiment 5 compound 5
Synthesis step is same as the second step in embodiment 1, simply by a kind of raw material 5-(thiophene-2-base therein)-2-bromine Thiophene changes into N-(4-bromophenyl) carbazole, obtain faint yellow solid product.
Product MS(m/e): 722, elementary analysis (C50H30N2S2): 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%.
The synthesis of embodiment 6 compound 6
Synthesis step is same as the second step in embodiment 1, simply by a kind of raw material 5-(thiophene-2-base therein)-2-bromine Thiophene changes into N-phenyl-3-bromine carbazole, obtains faint yellow solid product.
Product MS(m/e): 722, elementary analysis (C50H30N2S2): 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%.
The synthesis of embodiment 7 compound 7
Synthesis step is same as the second step in embodiment 1, simply by a kind of raw material 5-(thiophene-2-base therein)-2-bromine Thiophene changes into 6-phenyl-3-bromine dibenzothiophenes, obtains faint yellow solid product.
Product MS(m/e): 756, elementary analysis (C50H28S4): theoretical value C:79.33%, H:3.73%, S:16.94%； Measured value C:79.40%, H:3.78%, S:16.82%.
The synthesis of embodiment 8 compound 8
Synthesis step is same as the second step in embodiment 1, simply by a kind of raw material 5-(thiophene-2-base therein)-2-bromine Thiophene changes into 6-phenyl-3-bromine dibenzofurans, obtains faint yellow solid product.
Product MS(m/e): 724, elementary analysis (C50H28O2S2): 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%.
The synthesis of embodiment 9 compound 9
Synthesis step is same as the second step in embodiment 1, simply by a kind of raw material 5-(thiophene-2-base therein)-2-bromine Thiophene changes into 4-bromine diphenyl-(1-naphthyl) amine, obtains faint yellow solid product.
Product MS(m/e): 826, elementary analysis (C58H38N2S2): 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%.
The synthesis of embodiment 10 compound 10
Synthesis step is same as the second step in embodiment 1, simply by a kind of raw material 5-(thiophene-2-base therein)-2-bromine Thiophene changes into N-phenyl-6-phenyl-3-bromine carbazole, obtains faint yellow solid product.
Product MS(m/e): 874, elementary analysis (C62H38N2S2): 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%.
The synthesis of embodiment 11 compound 11
Synthesis step is same as the second step in embodiment 1, simply by a kind of raw material 5-(thiophene-2-base therein)-2-bromine Thiophene changes into 1-(4-bromophenyl)-2-Phenylbenzimidazole, obtains faint yellow solid product.
Product MS(m/e): 776, elementary analysis (C52H32N4S2): 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%.
The synthesis of embodiment 12 compound 12
Synthesis step is same as the second step in embodiment 1, simply by a kind of raw material 5-(thiophene-2-base therein)-2-bromine Thiophene changes into 1-phenyl-2-(4-bromophenyl) benzimidazole, obtains faint yellow solid product.
Product MS(m/e): 776, elementary analysis (C52H32N4S2): 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%.
The synthesis of embodiment 13 compound 13
Synthesis step is same as the second step in embodiment 1, simply by a kind of raw material 5-(thiophene-2-base therein)-2-bromine Thiophene changes into 2-phenyl-5-bromopyridine, obtains faint yellow solid product.
Product MS(m/e): 546, elementary analysis (C36H22N2S2): 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%.
The synthesis of embodiment 14 compound 14
Synthesis step is same as the second step in embodiment 1, simply by a kind of raw material 5-(thiophene-2-base therein)-2-bromine Thiophene changes into 2, and 3-diphenyl-6-bromine imidazo (1,2a) pyridine obtains faint yellow solid product.
Product MS(m/e): 776, elementary analysis (C52H32N4S2): 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%.
The synthesis of embodiment 15 compound 15
Synthesis step is same as the second step in embodiment 1, simply by a kind of raw material 5-(thiophene-2-base therein)-2-bromine Thiophene changes into 5-bromine benzophenanthrene, obtains faint yellow solid product.
Product MS(m/e): 692, elementary analysis (C50H28S2): theoretical value C:86.67%, H:4.07%, S:9.26%；Real Measured value C:86.70%, H:4.11%, S:9.19%.
The synthesis of embodiment 16 compound 16
Synthesis step is same as the second step in embodiment 1, simply by a kind of raw material 5-(thiophene-2-base therein)-2-bromine Thiophene changes into 10-(2-naphthyl)-9-bromine anthracene, obtain faint yellow solid product.
Product MS(m/e): 844, elementary analysis (C62H36S2): theoretical value C:88.12%, H:4.29%, S:7.59%；Real Measured value C:88.16%, H:4.31%, S:7.53%.
The synthesis of embodiment 17 compound 17
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[2,3-b:7,6-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene changes into 1-(4-bromine Phenyl)-2-Phenylbenzimidazole, obtain faint yellow solid product.
Product MS(m/e): 776, elementary analysis (C52H32N4S2): 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%.
The synthesis of embodiment 18 compound 18
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[2,3-b:7,6-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene changes into 2,3-hexichol Base-6-bromine imidazo (1,2-a) pyridine, obtains faint yellow solid product.
Product MS(m/e): 776, elementary analysis (C52H32N4S2): 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%.
The synthesis of embodiment 19 compound 19
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[2,3-b:7,6-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene changes into 4 bromine triphens Amine, obtains faint yellow solid product.
Product MS(m/e): 726, elementary analysis (C50H34N2S2): 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%.
The synthesis of embodiment 20 compound 20
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[2,3-b:7,6-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene changes into 4 bromine hexichol Base-(1-naphthyl) amine, obtains faint yellow solid product.
Product MS(m/e): 826, elementary analysis (C58H38N2S2): 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%.
The synthesis of embodiment 21 compound 21
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[2,3-b:7,6-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene changes into N-(4-bromine Phenyl) carbazole, obtain faint yellow solid product.
Product MS(m/e): 722, elementary analysis (C50H30N2S2): 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%.
The synthesis of embodiment 22 compound 22
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[2,3-b:7,6-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene change into N-phenyl- 6-phenyl-3-bromine carbazole, obtains faint yellow solid product.
Product MS(m/e): 874, elementary analysis (C62H38N2S2): 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%.
The synthesis of embodiment 23 compound 23
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[2,3-b:7,6-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene changes into 10(2-naphthalene Base)-9-bromine anthracene, obtain faint yellow solid product.
Product MS(m/e): 844, elementary analysis (C62H36S2): theoretical value C:88.12%, H:4.29%, S:7.59%；Real Measured value C:88.13%, H:4.25%, S:7.62%.
The synthesis of embodiment 24 compound 24
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[2,3-b:7,6-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene changes into 5 bromobenzenes also Phenanthrene, obtains faint yellow solid product.
Product MS(m/e): 692, elementary analysis (C50H28S2): theoretical value C:86.67%, H:4.07%, S:9.26%；Real Measured value C:86.71%, H:4.05%, S:9.24%.
The synthesis of embodiment 25 compound 25
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[2,3-b:7,6-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene changes into 6 phenyl-3- Bromine dibenzothiophenes, obtains faint yellow solid product.
Product MS(m/e): 756, elementary analysis (C50H28S4): theoretical value C:79.33%, H:3.73%, S:16.94%； Measured value C:79.35%, H:3.76%, S:16.89%.
The synthesis of embodiment 26 compound 26
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[2,3-b:7,6-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene changes into 6 phenyl-3- Bromine dibenzofurans, obtains faint yellow solid product.
Product MS(m/e): 724, elementary analysis (C50H28O2S2): 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%.
The synthesis of embodiment 27 compound 27
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[1,2-b:5,6-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene change into 10 phenyl- 9-bromine anthracene, obtains faint yellow solid product.
Product MS(m/e): 744, elementary analysis (C54H32S2): theoretical value C:87.06%, H:4.33%, S:8.61%；Real Measured value C:87.11%, H:4.29%, S:8.60%.
The synthesis of embodiment 28 compound 28
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[1,2-b:5,6-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene change into N-phenyl- 6-phenyl-3-bromine carbazole, obtains faint yellow solid product.
Product MS(m/e): 874, elementary analysis (C62H38N2S2): 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%.
The synthesis of embodiment 29 compound 29
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[1,2-b:5,6-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene changes into 4-bromine triphen Amine, obtains faint yellow solid product.
Product MS(m/e): 726, elementary analysis (C50H34N2S2): 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%.
The synthesis of embodiment 30 compound 30
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[1,2-b:5,6-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene changes into 4-bromine hexichol Base-(1-naphthyl) amine, obtains faint yellow solid product.
Product MS(m/e): 826, elementary analysis (C58H38N2S2): 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%.
The synthesis of embodiment 31 compound 31
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[1,2-b:5,6-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene changes into N-(4-bromine Phenyl) carbazole, obtain faint yellow solid product.
Product MS(m/e): 722, elementary analysis (C50H30N2S2): 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%.
The synthesis of embodiment 32 compound 32
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[1,2-b:5,6-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene change into N-phenyl- 6-phenyl-3-bromine carbazole, obtains faint yellow solid product.
Product MS(m/e): 874, elementary analysis (C62H38N2S2): 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%.
The synthesis of embodiment 33 compound 33
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[1,2-b:5,6-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene changes into 6 phenyl-3- Bromine dibenzothiophenes, obtains faint yellow solid product.
Product MS(m/e): 756, elementary analysis (C50H28S4): theoretical value C:79.33%, H:3.73%, S:16.94%； Measured value C:79.27%, H:3.76%, S:16.97%.
The synthesis of embodiment 34 compound 34
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[1,2-b:5,6-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene changes into 6 phenyl-3- Bromine dibenzofurans, obtains faint yellow solid product.
Product MS(m/e): 724, elementary analysis (C50H28O2S2): 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%.
The synthesis of embodiment 35 compound 35
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[2,1-b:6,5-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene changes into 6 phenyl-3- Bromine dibenzothiophenes, obtains faint yellow solid product.
Product MS(m/e): 756, elementary analysis (C50H28S4): theoretical value C:79.33%, H:3.73%, S:16.94%； Measured value C:79.29%, H:3.76%, S:16.95%.
The synthesis of embodiment 36 compound 36
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[2,1-b:6,5-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene change into 6-phenyl- 3-bromine dibenzofurans, obtains faint yellow solid product.
Product MS(m/e): 724, elementary analysis (C50H28O2S2): 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%.
The synthesis of embodiment 37 compound 37
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[2,1-b:6,5-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene changes into 4-bromine hexichol Base-(1-naphthyl) amine, obtains faint yellow solid product.
Product MS(m/e): 826, elementary analysis (C58H38N2S2): 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%.
The synthesis of embodiment 38 compound 38
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[2,1-b:6,5-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene change into N-phenyl- 6-phenyl-3-bromine carbazole, obtains faint yellow solid product.
Product MS(m/e): 874, elementary analysis (C62H38N2S2): 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%.
The synthesis of embodiment 39 compound 39
Synthesis step is same as embodiment 1, is simply changed by raw material naphtho-[2,3-b:6,7-b '] two thiophene in the first step For naphtho-[2,1-b:6,5-b '] two thiophene, the raw material 5-(thiophene-2-base in second step)-2-bromothiophene change into 10 phenyl- 9-bromine anthracene, obtains faint yellow solid product.
Product MS(m/e): 744, elementary analysis (C54H32S2): theoretical value C:87.06%, H:4.33%, S:8.61%；Real Measured value C:87.12%, H:4.30%, S:8.58%.
The Application Example of the compounds of this invention be presented herein below:
Embodiment 40: prepare device OLED-1 ~ OLED-10
Prepare the preferred implementation of device:
(1) device design
Comparing the performance that these holes are injected, transmitted material for convenience, the present invention devises a simple electroluminescence device (substrate/anode/hole injection layer (HIL)/hole transmission layer (HTL)/organic luminous layer (EL)/electron transfer layer (ETL)/the moon Pole), only use compound 1,7,9,10,16,20,22,28,30,37 to inject as hole, transmit material illustration, efficient hole Injection material 2-TNATA is as comparing material, and ADN doping TBPe is as emitting layer material.2-TNATA, NPB, AND and TBPe's Structure is:
Substrate can use the substrate in conventional organic luminescence device, such as: glass or plastics.Device system in the present invention Selecting glass substrate in work, ITO makees anode material.
Hole transmission layer can use various tri-arylamine group material.Hole selected in the element manufacturing of the present invention passes Defeated material is NPB.
Negative electrode can use metal and mixture structure thereof, such as Mg:Ag, Ca:Ag etc., it is also possible to is electron injecting layer/gold Belong to Rotating fields, such as LiF/Al, Li2The common cathode structures such as O.Electron injection material selected in the element manufacturing of the present invention Being LiF, cathode material is Al.
(2) making devices OLED-1
Glass plate supersound process in commercial detergent of transparent conductive layer will be coated with, rinse in deionized water, At acetone: ultrasonic oil removing in alcohol mixed solvent, it is baked to completely remove moisture content under clean environment, clear with ultraviolet light and ozone Wash, and with mental retardation cation bundle bombarded surface;
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5～9 × 10-3Pa, above-mentioned On anode tunic, the material 1,7,9,10,16,20,22,28,30,37,39 in vacuum evaporation this patent is as hole injection layer, Evaporation rate is 0.1nm/s, and evaporation thickness is 80nm；
Then being deposited with one layer of NPB on hole injection layer material again as hole transmission layer, evaporation rate is 0.1nm/s, Evaporation thickness is 20nm；
Vacuum evaporation luminescent layer on hole transmission layer, the method steamed altogether with double source, the steaming of evaporation ADN and TBPe, ADN Plating speed be the evaporation rate of 0.1nm/s, TBPe be 0.005nm/s, evaporation total film thickness is 30nm；
On luminescent layer, one layer of AlQ3 of vacuum evaporation is as electron transport material respectively, and its evaporation rate is 0.1nm/s,
Evaporation total film thickness is 20nm；
At the upper vacuum evaporation LiF of electron transfer layer (ETL) and Al layer as the negative electrode of device, thickness be respectively 0.5nm and 150nm。
Preparation OLED-2 ~ OLED-10, is only to change the compound as hole-injecting material as stated above.
Comparative example 1
Method, with embodiment 40, changes HIL material into 2-TNATA.
Device performance is shown 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
Embodiment 41: prepare device OLED-11, OLED-12 and OLED-13
HIL material, with embodiment 40, is changed into compound 34, and changes HIL thickness by method.The performance of device is shown in Table 2:
Table 2
Embodiment 42: prepare device OLED-14, OLED-15 and OLED-16
HIL material, with embodiment 40, is changed into 2-TNATA by method, and fluorescent host material selects compound 11,26 and 32.
The performance of device is shown in Table 3:(normal component structure: ITO/2-TNATA(80nm)/NPB(20nm)/fluorescent host: 5% Wt TBPe (30nm)/Alq3(20nm)/LiF(0.5nm)/Al(150nm))
Table 3
Result above shows, the new organic materials of the present invention is used for organic electroluminescence device, can effectively reduce Landing voltage, improves current efficiency, is hole-injecting material of good performance.
Although describe the present invention in conjunction with the embodiments, but the invention is not limited in above-described embodiment, it should reason Solving, under the guiding of present inventive concept, those skilled in the art can carry out various modifications and improvements, and claims summarise The scope of the present invention.

Claims (3)

1. naphtho-two thiophene derivant, described derivant structure formula is as follows:
2. naphtho-two thiophene derivant described in claim 1 is used as hole-injecting material, sky in organic electroluminescence device Hole transport materials or the application of fluorescent host material.
3. an organic electroluminescence device, including the first electrode and the second electrode and several between two electrodes Organic function layer, it is characterised in that at least one of which in organic function layer comprises the compound with following structural:
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