CN104870424A - Novel organic compound and organic light emitting device containing same - Google Patents

Novel organic compound and organic light emitting device containing same Download PDF

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Publication number
CN104870424A
CN104870424A CN201380066353.5A CN201380066353A CN104870424A CN 104870424 A CN104870424 A CN 104870424A CN 201380066353 A CN201380066353 A CN 201380066353A CN 104870424 A CN104870424 A CN 104870424A
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layer
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咸昊完
安贤哲
韩政佑
金东骏
金槿泰
李萤振
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Dongjin Semichem Co Ltd
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Priority claimed from PCT/KR2013/012278 external-priority patent/WO2014104797A1/en
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
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    • C07—ORGANIC CHEMISTRY
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    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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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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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
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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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur

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Abstract

The present invention relates to a novel organic compound, and more specifically, to: a novel organic compound having a ring closing structure of indole and furan and an arylamine group; and an organic light emitting device containing the same. The organic compound of the present invention has a simple charge transfer property and has high triplet energy and high glass transition temperature, and thus can provide low driving voltage, high efficiency, low power consumption and long lifespan to an organic light emitting device by being used as a hole injection or a hole transport material.

Description

Novel organic compound and comprise the organic illuminating element of this organic compound
Technical field
The present invention relates to a kind of organic compound of novelty and comprise the organic illuminating element of this organic compound, more particularly, relate to the characteristic having and easily transmit electric charge and there is the organic compound of the novelty of high triplet energy (hightriplet energy) and high glass-transition temperature (glass transition temperature) and comprise the organic illuminating element of this organic compound.
Background technology
Recently, can with the emissive type organic illuminating element of low voltage drive, with the liquid-crystal display (LCD of the main flow as flat panel displaying element, liquid crystal display) compare, field angle, contrast gradient etc. are excellent and without the need to backlight, thus can realize lightweight, slimming, also favourable and color reproduction range is wide in power consumption, therefore, receive much concern as display element of future generation.
In general, organic illuminating element has in negative electrode (electron injection electrode) and anode (hole injecting electrode) and the structure comprising organic matter layer between above-mentioned two electrodes.Now, organic matter layer is except comprising luminescent layer (EML, light emitting layer) outside, hole injection layer (HIL can also be comprised, hole injection layer), hole transmission layer (HTL, hole transport layer), electron transfer layer (ETL, electron transport layer), or electron injecting layer (EIL, electron injection layer), electronic barrier layer (EBL can be comprised further from the characteristics of luminescence of luminescent layer, electron blocking layer) or hole blocking layer (HBL, hole blocking layer).
If apply electric field to the organic illuminating element of this structure, then hole from anode inject and electronics inject from negative electrode, and hole and electronics reconfigure (recombination) at luminescent layer after respectively through hole transmission layer and electron transfer layer and form luminescent excitons (electron-hole pair, exitons).The luminescent excitons formed returns ground state (ground states) and gives out light.In order to improve efficiency and the stability of luminance, sometimes to adulterate luminophore at luminescent layer (main body).
Luminophore can divide into blueness, green, red light emitting substance and the yellow thoroughly realized needed for better self colour and the Yellow luminous material of Zhu according to emission wavelength.In addition, in order to increase purity of color and improve the luminous efficiency by energy trasfer, can the main consuming body/doping agent class as luminophore.
Its principle is as follows: if mix a small amount of doping agent at luminescent layer, then the electron-hole pair produced in main body transfers to doping agent and sends high-level efficiency light, and wherein, its band gap of described doping agent is less than the main body of main composition luminescent layer and luminous efficiency is excellent.Now, because the wavelength of main body moves to the wave band of doping agent, the light of desired wavelength thus can be obtained according to the kind of utilized doping agent and main body.
As the material of the hole injection layer and hole transmission layer that are used in organic illuminating element, there will be a known multiple compounds, but when make use of the organic illuminating element of material known up to now, due to high driving voltage, low efficiency and short work-ing life, thus have any problem in practical more.Therefore, constantly carried out the effort of a kind of organic illuminating element of exploitation, described organic illuminating element utilization has the material of excellent hole transporting properties thus has low voltage drive, high brightness and the characteristic of long life.
Summary of the invention
Technical problem
In order to solve problem as above, the present invention its object is to provide a kind of charge transfer characteristic good and has the organic compound of high triplet energy and high glass-transition temperature (Tg) and comprise this organic compound thus have low driving voltage, high-level efficiency, reduce power consumption and the organic illuminating element of long life.
To deal with problems scheme
In order to achieve the above object, the invention provides a kind of organic compound represented with following chemical formula 1:
[chemical formula 1]
In above-mentioned formula,
X is O, S, Se or Te;
L 1to L 3be hydrogen independently of one another; Heavy hydrogen; Tritium (tritium); or substituted or unsubstituted C 6-C 60aryl, C 4-C 60heteroaryl, C 6-C 30arylidene, C 4-C 30heteroarylidene or C 6-C 60condensation polycyclic base;
N is the integer of 0 to 2 independently of one another, wherein, and L 1to L 3in at least one its n be more than 1 and comprise
Above-mentioned Ar 1and Ar 2be hydrogen independently of one another; Heavy hydrogen; Tritium or substituted or unsubstituted C 6-C 60aryl, C 4-C 60heteroaryl or C 6-C 60condensation polycyclic base, Ar 1and Ar 2ring can be formed.
In addition, the invention provides a kind of organic illuminating element, this organic illuminating element comprises the compound represented with above-mentioned chemical formula 1 at hole injection layer or hole transmission layer.
Invention effect
The compound of chemical formula 1 of the present invention is owing to comprising structure and the arylamine of indoles (indole) and furans (furan) institute closed loop (ring closing), thus there is the characteristic of easily transmission electric charge and there is high triplet energy and high glass-transition temperature, therefore, it is possible to effectively as be suitable for all colours such as redness, green, blueness, white fluorescence and phosphorescence element, hole-injection characteristics and the excellent hole-injecting material of hole transport property and/or hole mobile material.
In addition, if use the compound of above-mentioned chemical formula 1 at hole injection layer or hole transmission layer, then low driving voltage, high-level efficiency, reduce power consumption and the organic illuminating element of long life can be made.
Accompanying drawing explanation
Fig. 1 schematically illustrates the section of the OLED according to one embodiment of the invention.
Embodiment
With the compound of the present invention that following chemical formula 1 represents, it is characterized in that there is structure and the aryl amine of indoles and furans institute closed loop (ring-closing):
[chemical formula 1]
In above-mentioned formula,
X is O, S, Se or Te;
L 1to L 3be hydrogen independently of one another; Heavy hydrogen; Tritium (tritium); or substituted or unsubstituted C 6-C 60aryl, C 4-C 60heteroaryl, C 6-C 30arylidene, C 4-C 30heteroarylidene or C 6-C 60condensation polycyclic base;
N is the integer of 0 to 2 independently of one another, wherein, and L 1to L 3in at least one its n be more than 1 and comprise
Above-mentioned Ar 1and Ar 2be hydrogen independently of one another; Heavy hydrogen; Tritium or substituted or unsubstituted C 6-C 60aryl, C 4-C 60heteroaryl or C 6-C 60condensation polycyclic base, Ar 1and Ar 2ring can be formed.
In addition, with regard to above-mentioned substituting group, be selected from by heavy hydrogen, halogen, amino, itrile group, nitro, C 1~ C 40alkyl, C 2~ C 40thiazolinyl, C 1~ C 40alkoxyl group, C 3~ C 40cycloalkyl, C 3~ C 40heterocyclylalkyl, C 6~ C 40aryl and C 3~ C 40heteroaryl composition group in the base of more than a kind can be substituted.
In compound of the present invention, above-mentioned furans is owing to having high triplet energy, and thus when being applicable to organic illuminating element, play a part to provide low driving voltage, high-level efficiency and reduce power consumption, indoles makes electric charge easily transmit.Therefore, when above-mentioned furans and indoles closed loop (ring-closing), can high glass-transition temperature being obtained, the characteristic of thermostability and long life can be obtained thus when being applicable to organic illuminating element.
In addition, above-mentioned arylamine part (moiety) plays a part electric charge is easily transmitted.
In the present invention, the compound of above-mentioned chemical formula 1 can be selected from the group be made up of the compound represented with following chemical formula 2 to chemical formula 8, but is not limited thereto:
[chemical formula 2]
[chemical formula 3]
[chemical formula 4]
[chemical formula 5]
[chemical formula 6]
[chemical formula 7]
[chemical formula 8]
X is O, S, Se or Te;
L 4to L 6be substituted or unsubstituted C independently of one another 6-C 60aryl, C 4-C 60heteroaryl, C 6-C 30arylidene, C 4-C 30heteroarylidene or C 6-C 60condensation polycyclic base;
N is the integer of 0 to 2 independently of one another, wherein, and L 4to L 6in at least one its n be more than 1;
Ar 1to Ar 7be hydrogen independently of one another; Heavy hydrogen; Tritium or substituted or unsubstituted C 6-C 60aryl, C 4-C 60heteroaryl or C 6-C 60condensation polycyclic base, adjacent Ar can form ring each other.
In the present invention, the preference of the compound represented with above-mentioned chemical formula 1 is as follows:
Compound of the present invention is due to the high furans closed loop of the indoles and triplet energies that make easily to transmit electric charge, and comprise the arylamine easily transmitting electric charge, therefore, there is the characteristic easily transmitting electric charge, and high triplet energy and high glass-transition temperature can be had.
Aromatic series boron compound and aromatic halogen compound are undertaken reacting the compound just can prepared according to chemical formula 1 of the present invention by Suzuki-coupling (Suzuki-coupling) reaction be widely known by the people in C-C coupling reaction.Such as, the compound of chemical formula 2a, 2b, 3a, 3b and 4a of the present invention can be prepared separately as shown in following reaction formula 1 to reaction formula 5.
[reaction formula 1]
[reaction formula 2]
[reaction formula 3]
[reaction formula 4]
[reaction formula 5]
L 6substituted or unsubstituted C 6-C 60aryl, C 4-C 60heteroaryl, C 6-C 30arylidene, C 4-C 30heteroarylidene or C 6-C 60condensation polycyclic base;
N is the integer of 0 to 2,
Ar 1to Ar 7be hydrogen independently of one another; Or substituted or unsubstituted C 6-C 60aryl, C 4-C 60heteroaryl or C 6-C 60condensation polycyclic base.
In addition, the invention provides and a kind ofly comprise the compound or their mixture that represent using above-mentioned chemical formula 1 and as the organic illuminating element of hole injecting material or hole transporting material.
In addition, organic illuminating element of the present invention comprises the organic thin film layer of more than 1 layer, and this organic thin film layer contains the compound represented with above-mentioned chemical formula 1, and the preparation method that the following describes above-mentioned organic illuminating element is as follows.Preferably, the organic thin film layer of more than 1 layer comprising the compound represented with above-mentioned chemical formula 1 is hole injection layer or hole transmission layer.
The organic thin film layers such as hole injection layer (HIL), hole transmission layer (HTL), luminescent layer (EML), electron transfer layer (ETL), electron injecting layer (EIL) can be comprised more than 1 by above-mentioned organic illuminating element between anode (anode) and negative electrode (cathode).
First, at substrate top evaporation, there is the positive electrode material of high work function and form anode.Now, aforesaid substrate can be used in the substrate that common organic illuminating element uses, and especially preferably uses glass substrate or transparent plastic substrate that physical strength, thermostability, transparency, surface flatness, handling easiness and water-repellancy are excellent.In addition, as positive electrode material, the tin indium oxide (ITO) that transparent and electrically conductive can be used excellent, indium zinc oxide (IZO), stannic oxide (SnO 2), zinc oxide (ZnO) etc.Above-mentioned positive electrode material can utilize common anodic formation method to carry out evaporation, specifically, vapour deposition method or sputtering method can be utilized to carry out evaporation.
Thereafter, utilize as vacuum vapour deposition, spin-coating method, teeming practice, Langmuir-Blodgett (Langmuir-Blodgett, LB) method such as method can form the compound or known hole injection layer material that represent with above-mentioned chemical formula 1 on above-mentioned positive electrode top, and the uniform film quality and not easily produce pin hole (pinhole) angularly of being easy to get calmly, preferably utilize vacuum vapour deposition and formed.When forming hole injection layer when utilizing above-mentioned vacuum vapour deposition, although its evaporation condition is with being used as the compound of material of hole injection layer, the structure of desired hole injection layer and thermal property etc. and different, but in general, preferably the evaporation temperature, 10 of 50-500 DEG C -8to 10 -3holder (torr) vacuum tightness, 0.01 to evaporation rate and suitably select to the layer thicknesses of 5 μm.
Above-mentioned known hole injection layer material, although be not particularly limited, but can by United States Patent (USP) the 4th, 356, phthalocyanine compound or the TCTA (4 as star burst sulfonamide derivatives class such as the CuPc disclosed in No. 429,4 ＇, 4 "-three (N-carbazyl) triphenylamine), m-MTDATA (4; 4 ＇; 4 "-three (3-MethYlphenylamino) triphenylamine), m-MTDAPB (4,4 ＇, 4 "-three (3-MethYlphenylamino) phenoxy group benzene), HI-406 (N 1, N 1＇-(xenyl-4,4 ＇-two base) two (N 1-(naphthalene-1-base)-N 4, N 4-diphenyl benzene-Isosorbide-5-Nitrae-diamines) etc. be used as hole injection layer material.
Then, utilize the compound as the methods such as vacuum vapour deposition, spin-coating method, teeming practice, LB method can represent with above-mentioned chemical formula 1 in the formation of above-mentioned hole injection layer top or known hole transmission layer material, and be easy to get calmly uniform film quality and not easily produce pin hole angularly, preferably utilize vacuum vapour deposition and formed.When forming hole transmission layer when utilizing above-mentioned vacuum vapour deposition, although its evaporation condition is different with used compound, in general, preferably select in the condition and range almost identical with forming hole injection layer.
In addition, above-mentioned known hole transmission layer material, although be not particularly limited, it can select and use arbitrarily in the common known material being used in hole transmission layer.Specifically, above-mentioned hole transmission layer material can use carbazole derivative and the N such as N-phenyl carbazole, Polyvinyl carbazole, N ＇-bis-(3-aminomethyl phenyl)-N, N ＇-phenylbenzene-[1,1-xenyl]-4,4 ＇-diamines (TPD), N, N ＇-two (naphthalene-1-base)-N, N ＇-diphenylbenzidine (α-NPD) etc. have the common sulfonamide derivatives etc. of aromatic fused ring.
Thereafter, can at above-mentioned hole transmission layer top coating luminescent layer material by vapour deposition method or solution-treated.When forming luminescent layer when utilizing above-mentioned vacuum vapour deposition, although its evaporation condition is different with used compound, in general, preferably select in the condition and range almost identical with forming hole injection layer.In addition, above-mentioned emitting layer material can use known emitting layer material, and phosphorescence or fluorescent dopants can be used in the lump and forms luminescent layer.Now, IDE102 or IDE105 or BD142 (N that can buy in Co., Ltd.'s bright dipping (Idemitsu company) can be used as fluorescent dopants 6, N 12-bis-(3,4-3,5-dimethylphenyl)-N 6, N 12-two sym-trimethylbenzene bases (chrysene)-6,12-diamines), can by green phosphorescent doping agent Ir (ppy) as phosphorescent dopants 3(three (2-phenylpyridine) iridium), F2Irpic (two (4 as blue phosphorescent doping agent, 6-difluorophenyl pyridinato-N, C2 ＇) pyridinecarboxylic closes iridium (III)), the red phosphorescent doping agent RD61 etc. of UDC company (Universal Display Corporation, the U.S.) jointly carries out vacuum evaporation (doping) and uses.
In addition, when being used on luminescent layer together with phosphorescent dopants, in order to prevent the phenomenon that triplet exciton or hole are spread to electron transfer layer, preferably by vacuum vapour deposition or spin-coating method, further stacked hole suppresses material (HBL).Now, although the hole inhibitory substance that can use is not particularly limited, can selects arbitrarily in the known material being used as hole suppression material and utilize.Such as, hole described in oxadiazoles (oxadiazole) derivative or triazole derivative, phenanthroline derivative or Japanese Unexamined Patent Publication 11-329734 (A1) can be enumerated and suppress material etc., as its representative, Balq (two (8-hydroxy-2-methylquinoline-N1 can be used, O8)-biphenylyloxy aluminium), phenanthroline (phenanthrolines) compounds (such as: UDC company bathocuproine (Bathocuproine, BCP)) etc.
Form electron transfer layer on the luminescent layer top formed as described above, and now utilize the methods such as vacuum vapour deposition, spin-coating method, teeming practice to form above-mentioned electron transfer layer, especially preferably utilize vacuum vapour deposition and formed.
Above-mentioned electron transport layer materials transmits the function from electron injection electrode institute injected electrons with playing stably, and its kind is not particularly limited, and such as, can use quinoline, especially can use three (oxine) aluminium (Alq 3) or ET4 (6,6 ＇-(3,4-bis-sym-trimethylbenzene base-1,1-dimethyl-1H-thiophene coughs up-2,5-bis-bases) two-2,2 ＇-dipyridyl).In addition, portion stackedly can have the material of function and electron injecting layer (EIL) that electronics is easily injected from negative electrode on the electron transport layer, as electron injecting layer material, LiF (lithium fluoride), NaCl (sodium-chlor), CsF (cesium fluoride), Li can be utilized 2the materials such as O (Lithium Oxide 98min), BaO (barium oxide).
In addition, although the evaporation condition of above-mentioned electron transfer layer is different with used compound, in general, preferably select in the condition and range almost identical with forming hole injection layer.
Thereafter, electron injecting layer material can be formed on above-mentioned electron transfer layer top, now, common electron injecting layer material is formed above-mentioned electron transfer layer by methods such as vacuum vapour deposition, spin-coating method, teeming practices, especially forms above-mentioned electron transfer layer preferably by vacuum vapour deposition.
Finally, the method such as vacuum vapour deposition or sputter (sputtering) method is utilized to form negative electrode formation metal on electron injecting layer top and be used as negative electrode.Here, there is the metal of low work function, alloy, electric conductivity compound and their mixture and can be used as negative electrode formation metal.As object lesson, there are lithium (Li), magnesium (Mg), aluminium (Al), aluminium-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-Yin (Mg-Ag) etc.In addition, in order to obtain top emitting element, the transmission-type negative electrode employing ITO, IZO can also be utilized.
Organic illuminating element of the present invention can be not only the organic illuminating element with anode, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer, cathode construction, and the organic luminous element structure of various structures can be had, also can form the middle layer of 1 layer or 2 layers as required further.
As mentioned above, the thickness of each organic thin film layer formed according to the present invention can regulate according to required degree, and described thickness is preferably 10 to 1,000nm, is more preferably 20 to 150nm.
In addition, in the present invention, comprise the organic thin film layer of the compound represented with above-mentioned chemical formula 1 owing to can regulate the thickness of organic thin film layer with molecular unit, therefore, there is surface uniform and the preeminent advantage of morphological stability.
Below, in order to help to understand the present invention, preferred embodiment is shown, and following embodiment just illustrates the present invention, scope of the present invention also be can't help following embodiment and limited.
The synthesis of intermediate 1-3
[synthesis of 1-1]
In round-bottomed flask, cumarone-3-ylboronic acid (benzofuran-3-ylboronic acid) the bromo-2-of 59.3g, 4-iodo-1-oil of mirbane (4-bromo-2-iodo-1-nitrobenzene) 100g to be dissolved in toluene 1600ml and to add K 2cO 3(2M) 450ml and Pd (PPh 3) 4return stirring has been carried out after (tetrakis triphenylphosphine palladium) 10.5g.Confirm to react with TLC (thin layer chromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 82.5g intermediate 1-1 (productive rate is 85%).
[synthesis of 1-2]
P (OEt) is added after being dissolved by above-mentioned for 80g 1-1 in 1,2-dichlorobenzene (1,2-dichlorobenzene) 400ml 3(triethoxy phosphine) 260ml has also carried out return stirring.MC (methylene dichloride) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 43.9g intermediate 1-2 (productive rate is 61%).
[synthesis of 1-3]
By above-mentioned for 40g 1-2, iodobenzene (Iodobenzene) 57g, t-BuONa (sodium tert-butoxide) 20.1g, Pd 2(dba) 3(three (dibenzalacetone) two palladium) 5.1g, (t-Bu) 3p (tri-butyl phosphine) 11.3ml has carried out return stirring after dissolving in toluene 800ml.Confirm to react with TLC (thin layer chromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 13.2g intermediate 1-3 (productive rate is 26%).
The synthesis of intermediate 2-3
[synthesis of 2-1]
In round-bottomed flask, cumarone-3-ylboronic acid (benzofuran-3-ylboronic acid) the bromo-1-of 59.3g, 4-iodo-2-oil of mirbane (4-bromo-1-iodo-2-nitrobenzene) 100g to be dissolved in toluene 1600ml and to add K 2cO 3(2M) 450ml and Pd (PPh 3) 4return stirring has been carried out after (tetrakis triphenylphosphine palladium) 10.5g.Confirm to react with TLC (thin layer chromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 73.7g intermediate 2-1 (productive rate is 76%).
[synthesis of 2-2]
P (OEt) is added after being dissolved by above-mentioned for 70g 1-1 in 1,2-dichlorobenzene (1,2-dichlorobenzene) 350ml 3(triethoxy phosphine) 220ml has also carried out return stirring.MC (methylene dichloride) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 35.2g intermediate 2-2 (productive rate is 56%).
[synthesis of 2-3]
By above-mentioned for 35g 2-2, iodobenzene (Iodobenzene) 49g, t-BuONa (sodium tert-butoxide) 17.6g, Pd 2(dba) 3(three (dibenzalacetone) two palladium) 4.5g, (t-Bu) 3p (tri-butyl phosphine) 10ml has carried out return stirring after dissolving in toluene 700ml.Confirm to react with TLC (thin layer chromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 16.6g intermediate 2-3 (productive rate is 33%).
The synthesis of intermediate 3-3
[synthesis of 3-1]
In round-bottomed flask, benzo [b] thiene-3-yl-boric acid (benzo [b] thiophen-3-ylboronicacid) the bromo-2-of 65.1g, 4-iodo-1-oil of mirbane (4-bromo-2-iodo-1-nitrobenzene) 100g to be dissolved in toluene 1600ml and to add K 2cO 3(2M) 455ml and Pd (PPh 3) 4return stirring has been carried out after (tetrakis triphenylphosphine palladium) 10.5g.Confirm to react with TLC (thin layer chromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 87.6g intermediate 3-1 (productive rate is 86%).
[synthesis of 3-2]
Above-mentioned for 85g 3-1 to be dissolved in 1,2-dichlorobenzene (1,2-dichlorobenzene) 430ml and to add P (OEt) 3return stirring has been carried out after (triethoxy phosphine) 260ml.MC (methylene dichloride) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 49.1g intermediate 3-2 (productive rate is 64%).
[synthesis of 3-3]
By above-mentioned for 49g 3-2, iodobenzene (Iodobenzene) 66g, t-BuONa (sodium tert-butoxide) 23.3g, Pd 2(dba) 3(three (dibenzalacetone) two palladium) 5.9g, (t-Bu) 3p (tri-butyl phosphine) 13.1ml has carried out return stirring after dissolving in toluene 980ml.Confirm to react with TLC (thin layer chromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 19g intermediate 3-3 (productive rate is 31%).
The synthesis of intermediate 4-3
[synthesis of 4-1]
In round-bottomed flask, benzo [b] thiene-3-yl-boric acid (benzo [b] thiophen-3-ylboronicacid) the bromo-1-of 65.1g, 4-iodo-2-oil of mirbane (4-bromo-1-iodo-2-nitrobenzene) 100g to be dissolved in toluene 1600ml and to add K 2cO 3(2M) 455ml and Pd (PPh 3) 4return stirring has been carried out after (tetrakis triphenylphosphine palladium) 10.5g.Confirm to react with TLC (thin layer chromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 84.5g intermediate 4-1 (productive rate is 83%).
[synthesis of 4-2]
Above-mentioned for 84g 4-1 to be dissolved in 1,2-dichlorobenzene (1,2-dichlorobenzene) 420ml and to add P (OEt) 3return stirring has been carried out after (triethoxy phosphine) 250ml.MC (methylene dichloride) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 41.7g intermediate 4-2 (productive rate is 55%).
[synthesis of 4-3]
By above-mentioned for 40g 4-2, iodobenzene (Iodobenzene) 54g, t-BuONa (sodium tert-butoxide) 19g, Pd 2(dba) 3(three (dibenzalacetone) two palladium) 4.8g, (t-Bu) 3p (tri-butyl phosphine) 10.7ml has carried out return stirring after dissolving in toluene 800ml.Confirm to react with TLC (thin layer chromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 17.5g intermediate 4-3 (productive rate is 35%).
The synthesis of intermediate 5-2
[synthesis of 5-1]
In round-bottomed flask, cumarone-3-ylboronic acid (benzofuran-3-ylboronic acid) 78.5g, 1-iodo-2-oil of mirbane (1-iodo-2-nitrobenzene) 100g to be dissolved in toluene 1000ml and to add K 2cO 3(2M) 600ml and Pd (PPh 3) 4return stirring has been carried out after (tetrakis triphenylphosphine palladium) 13.9g.Confirm to react with TLC (thin layer chromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 78.7g intermediate 5-1 (productive rate is 82%).
[synthesis of 5-2]
Above-mentioned for 78g 5-1 to be dissolved in 1,2-dichlorobenzene (1,2-dichlorobenzene) 400ml and to add P (OEt) 3return stirring has been carried out after (triethoxy phosphine) 260ml.MC (methylene dichloride) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 36.4g intermediate 5-2 (productive rate is 54%).
The synthesis of intermediate 6-2
[synthesis of 6-1]
In round-bottomed flask, benzo [b] thiene-3-yl-boric acid (benzo [b] thiophen-3-ylboronicacid) 87.7g, 1-iodo-2-oil of mirbane (1-iodo-2-nitrobenzene) 100g to be dissolved in toluene 1000ml and to add K 2cO 3(2M) 600ml and Pd (PPh 3) 4return stirring has been carried out after (tetrakis triphenylphosphine palladium) 13.9g.Confirm to react with TLC (thin layer chromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 82g intermediate 6-1 (productive rate is 80%).
[synthesis of 6-2]
Above-mentioned for 80g 6-1 to be dissolved in 1,2-dichlorobenzene (1,2-dichlorobenzene) 400ml and to add P (OEt) 3return stirring has been carried out after (triethoxy phosphine) 310ml.MC (methylene dichloride) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 39.8g intermediate 6-2 (productive rate is 57%).
The synthesis of compound 1
In round-bottomed flask, by bromo-to N-phenyl-1-naphthylamine (N-phenylnaphthalen-1-amine) 10g, 1-4-iodobenzene (1-bromo-4-Iodobenzene) 18.0g, t-BuONa (sodium tert-butoxide) 6.5g, Pd 2(dba) 3(three (dibenzalacetone) two palladium) 1.7g, (t-Bu) 3p (tri-butyl phosphine) 2.6ml stirs with the temperature of 50 DEG C after dissolving in toluene 100ml.Confirm to react with TLC (thin layerchromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 7.6g intermediate OP1 (productive rate is 45%).
By above-mentioned for 7.5g OP1, two (tetramethyl ethylene ketone conjunction) two boron (bis (pinacolato) diboron) 6.62g, Pd (dppf) Cl 2([two (diphenylphosphino) ferrocene of 1,1'-] palladium chloride) 0.07g, KOAc (Potassium ethanoate) 5.9g has carried out return stirring after dissolving in toluene 80ml.Confirm to react with TLC (thin layerchromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 6.8g intermediate OP2 (productive rate is 81%).
In round-bottomed flask, above-mentioned for 2.0g intermediate 1-3 and 2.8gOP2 to be dissolved in toluene 40ml and to add K 2cO 3(2M) 8ml and Pd (PPh 3) 4return stirring has been carried out after (tetrakis triphenylphosphine palladium) 0.2g.Confirm to react with TLC (thin layer chromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 2.3g compound 1 (productive rate is 72%).
m/z：576.22(100.0％)、577.22(46.2％)、578.23(10.2％)、579.23(1.6％)
The synthesis of compound 2
Two (naphthalene-1-base) amine (di (naphthalen-1-yl) amine) has been synthesized N-(naphthalene-1-base)-N-(4-(4 as initial substance with the method identical with OP1, OP2 of compound 1,4,5,5-tetramethyl--1,3,2-dioxy boron penta ring-2-base) phenyl) naphthalene-1-amine (N-(naphthalen-1-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) naphthalen-1-amine).
In round-bottomed flask, by 2.0g intermediate 1-3, N-(naphthalene-1-base)-N-(4-(4,4,5,5-tetramethyl--1,3,2-dioxy boron penta ring-2-base) phenyl) naphthalene-1-amine (N-(naphthalen-1-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) naphthalen-1-amine) 3.12g to dissolve in toluene 40ml and to add K 2cO 3(2M) 8ml and Pd (PPh 3) 4return stirring has been carried out after (tetrakis triphenylphosphine palladium) 0.19g.Confirm to react with TLC (thin layer chromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 2.4g compound 2 (productive rate is 70%).
m/z：626.24(100.0％)、627.24(50.1％)、628.24(12.7％)、629.25(2.0％)
The synthesis of compound 3
By N-([1, 1'-biphenyl]-4-base) naphthalene-1-amine (N-([1, 1 ＇-biphenyl]-4-yl) naphthalen-1-amine) as initial substance and with the OP1 with compound 1, the method that OP2 is identical has synthesized N-([1, 1'-biphenyl]-4-base)-N-(4-(4, 4, 5, 5-tetramethyl--1, 3, 2-dioxy boron penta ring-2-base) phenyl) naphthalene-1-amine (N-([1, 1 ＇-biphenyl]-4-yl)-N-(4-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) naphthalen-1-amine).
In round-bottomed flask, by 2.0g intermediate 1-3, N-([1,1'-biphenyl]-4-base)-N-(4-(4,4,5,5-tetramethyl--1,3,2-dioxy boron penta ring-2-base) phenyl) naphthalene-1-amine (N-([1,1 ＇-biphenyl]-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) naphthalen-1-amine) naphthalene-1-amine) 3.3g to dissolve in toluene 40ml and to add K 2cO 3(2M) 8ml and Pd (PPh 3) 4return stirring has been carried out after (tetrakis triphenylphosphine palladium) 0.19g.Confirm to react with TLC (thin layer chromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 2.6g compound 3 (productive rate is 73%).
m/z：652.25(100.0％)、653.25(52.7％)、654.26(13.6％)、655.26(2.4％)
The synthesis of compound 4
By two ([1, 1'-biphenyl]-4-base) amine (di ([1, 1 ＇-biphenyl]-4-yl) amine) as initial substance and with the OP1 with compound 1, the method that OP2 is identical has synthesized N-([1, 1'-biphenyl]-4-base)-N-(4-(4, 4, 5, 5-tetramethyl--1, 3, 2-dioxy boron penta ring-2-base) phenyl)-[1, 1'-biphenyl]-4-amine (N-([1, 1 ＇-biphenyl]-4-yl)-N-(4-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl)-[1, 1 ＇-biphenyl]-4-amine).
In round-bottomed flask, by 2.0g intermediate 1-3, N-([1,1'-biphenyl]-4-base)-N-(4-(4,4,5,5-tetramethyl--1,3,2-dioxy boron penta ring-2-base) phenyl)-[1,1'-biphenyl]-4-amine (N-([1,1 ＇-biphenyl]-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-[1,1 ＇-biphenyl]-4-amine) 3.4g to dissolve in toluene 40ml and to add K 2cO 3(2M) 8.2ml and Pd (PPh 3) 4return stirring has been carried out after (tetrakis triphenylphosphine palladium) 0.19g.Confirm to react with TLC (thin layerchromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 2.5g compound 4 (productive rate is 69%).
m/z：678.27(100.0％)、679.27(54.5％)、680.27(15.0％)、681.28(2.5％)
The synthesis of compound 5
By N-([1, 1'-biphenyl]-4-base)-9, 9-dimethyl-9H-fluorenes-2-amine (N-([1, 1 ＇-biphenyl]-4-yl)-9, 9-dimethyl-9H-fluoren-2-amine) as initial substance and with the OP1 with compound 1, the method that OP2 is identical has synthesized N-([1, 1'-biphenyl]-4-base)-N-(4-(4, 4, 5, 5-tetramethyl--1, 3, 2-dioxy boron penta ring-2-base) phenyl)-9, 9-dimethyl-9H-fluorenes-2-amine (N-([1, 1 ＇-biphenyl]-4-yl)-9, 9-dimethyl-N-(4-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl)-9H-fluoren-2-amine).
In round-bottomed flask, by 2.0g intermediate 1-3, N-([1,1'-biphenyl]-4-base)-N-(4-(4,4,5,5-tetramethyl--1,3,2-dioxy boron penta ring-2-base) phenyl)-9,9-dimethyl-9H-fluorenes-2-amine (N-([1,1 ＇-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-9H-fluoren-2-amine) 3.7g to dissolve in toluene 40ml and to add K 2cO 3(2M) 8.2ml and Pd (PPh 3) 4return stirring has been carried out after (tetrakis triphenylphosphine palladium) 0.19g.Confirm to react with TLC (thin layerchromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 2.9g compound 5 (productive rate is 73%).
m/z：718.30(100.0％)、719.30(58.5％)、720.31(16.4％)、721.31(3.2％)
The synthesis of compound 6
By N-([1, 1'-biphenyl]-4-base)-9, 9-phenylbenzene-9H-fluorenes-2-amine (N-([1, 1 ＇-biphenyl]-4-yl)-9, 9-diphenyl-9H-fluoren-2-amine) as initial substance and with the OP1 with compound 1, the method that OP2 is identical has synthesized N-([1, 1'-biphenyl]-4-base)-N-(4-(4, 4, 5, 5-tetramethyl--1, 3, 2-dioxy boron penta ring-2-base) phenyl)-9, 9-phenylbenzene-9H-fluorenes-2-amine (N-([1, 1 ＇-biphenyl]-4-yl)-9, 9-diphenyl-N-(4-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl)-9H-fluoren-2-amined).
In round-bottomed flask, by 2.0g intermediate 1-3, N-([1,1'-biphenyl]-4-base)-N-(4-(4,4,5,5-tetramethyl--1,3,2-dioxy boron penta ring-2-base) phenyl)-9,9-phenylbenzene-9H-fluorenes-2-amine (N-([1,1 ＇-biphenyl]-4-yl)-9,9-diphenyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-9H-fluoren-2-amined) 4.5g to dissolve in toluene 40ml and to add K 2cO 3(2M) 8.2ml and Pd (PPh 3) 4return stirring has been carried out after (tetrakis triphenylphosphine palladium) 0.19g.Confirm to react with TLC (thin layer chromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 3.0g compound 6 (productive rate is 65%).
m/z：842.33(100.0％)、843.33(68.9％)、844.34(23.2％)、845.34(5.3％)
The synthesis of compound 7
By two ([1, 1'-biphenyl]-4-base) amine (di ([1, 1 ＇-biphenyl]-4-yl) amine) and the bromo-3-iodobenzene (1-bromo-3-Iodobenzene) of 1-as initial substance and with the OP1 with compound 1, the method that OP2 is identical has synthesized N-([1, 1'-biphenyl]-4-base)-N-(3-(4, 4, 5, 5-tetramethyl--1, 3, 2-dioxy boron penta ring-2-base) phenyl)-[1, 1'-biphenyl]-4-amine (N-([1, 1 ＇-biphenyl]-4-yl)-N-(3-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl)-[1, 1 ＇-biphenyl]-4-amine).
In round-bottomed flask, by 2.0g intermediate 1-3, N-([1,1'-biphenyl]-4-base)-N-(3-(4,4,5,5-tetramethyl--1,3,2-dioxy boron penta ring-2-base) phenyl)-[1,1'-biphenyl]-4-amine (N-([1,1 ＇-biphenyl]-4-yl)-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-[1,1 ＇-biphenyl]-4-amine) 3.4g to dissolve in toluene 40ml and to add K 2cO 3(2M) 8.2ml and Pd (PPh 3) 4return stirring has been carried out after (tetrakis triphenylphosphine palladium) 0.19g.Confirm to react with TLC (thin layerchromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 2.1g compound 7 (productive rate is 60%).
m/z：678.27(100.0％)、679.27(54.5％)、680.27(15.0％)、681.28(2.5％)
The synthesis of compound 8
By N-([1, 1'-biphenyl]-4-base)-9, 9-dimethyl-9H-fluorenes-2-amine (N-([1, 1 ＇-biphenyl]-4-yl)-9, 9-dimethyl-9H-fluoren-2-amine) and the bromo-3-iodobenzene (1-bromo-3-Iodobenzene) of 1-as initial substance and with the OP1 with compound 1, the method that OP2 is identical has synthesized N-([1, 1'-biphenyl]-4-base)-N-(3-(4, 4, 5, 5-tetramethyl--1, 3, 2-dioxy boron penta ring-2-base) phenyl)-9, 9-dimethyl-9H-fluorenes-2-amine (N-([1, 1 ＇-biphenyl]-4-yl)-9, 9-dimethyl-N-(3-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl)-9H-fluoren-2-amine).
In round-bottomed flask, by 2.0g intermediate 1-3, N-([1,1'-biphenyl]-4-base)-N-(3-(4,4,5,5-tetramethyl--1,3,2-dioxy boron penta ring-2-base) phenyl)-9,9-dimethyl-9H-fluorenes-2-amine (N-([1,1 ＇-biphenyl]-4-yl)-9,9-dimethyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-9H-fluoren-2-amine) 3.7g to dissolve in toluene 40ml and to add K 2cO 3(2M) 8ml and Pd (PPh 3) 4return stirring has been carried out after (tetrakis triphenylphosphine palladium) 0.19g.Confirm to react with TLC (thin layerchromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 2.4g compound 8 (productive rate is 62%).
m/z：718.30(100.0％)、719.30(58.5％)、720.31(16.4％)、721.31(3.2％)
The synthesis of compound 9
Carry out except replacing 1-3 with 3-3, except reaction, synthesizing with the method identical with compound 4.
m/z：694.24(100.0％)、695.25(54.5％)、696.25(15.0％)、696.24(4.9％)、697.25(2.7％)、697.24(2.5％)、695.24(1.5％)
The synthesis of compound 10
Carry out except replacing 1-3 with 3-3, except reaction, synthesizing with the method identical with compound 5.
m/z：734.28(100.0％)、735.28(57.8％)、736.28(17.0％)、736.27(4.5％)、737.29(3.0％)、737.27(2.6％)、735.27(1.5％)
The synthesis of compound 11
Carry out except replacing 1-3 with 3-3, except reaction, synthesizing with the method identical with compound 6.
m/z：858.31(100.0％)、859.31(69.4％)、860.31(23.9％)、861.32(5.1％)、860.30(4.5％)、861.31(3.5％)、862.31(1.1％)
The synthesis of compound 12
Carry out except replacing 1-3 with 3-3, except reaction, synthesizing with the method identical with compound 7.
m/z：694.24(100.0％)、695.25(54.5％)、696.25(15.0％)、696.24(4.9％)、697.25(2.7％)、697.24(2.5％)、695.24(1.5％)
The synthesis of compound 13
Carry out except replacing 1-3 with 3-3, except reaction, synthesizing with the method identical with compound 8.
m/z：734.28(100.0％)、735.28(57.8％)、736.28(17.0％)、736.27(4.5％)、737.29(3.0％)、737.27(2.6％)、735.27(1.5％)
The synthesis of compound 14
Carry out except replacing 1-3 with 2-3, except reaction, synthesizing with the method identical with compound 5.
m/z：718.30(100.0％)、719.30(58.5％)、720.31(16.4％)、721.31(3.2％)
The synthesis of compound 15
Carry out except replacing 1-3 with 2-3, except reaction, synthesizing with the method identical with compound 8.
m/z：718.30(100.0％)、719.30(58.5％)、720.31(16.4％)、721.31(3.2％)
The synthesis of compound 16
Carry out except replacing 1-3 with 4-3, except reaction, synthesizing with the method identical with compound 5.
m/z：734.28(100.0％)、735.28(57.8％)、736.28(17.0％)、736.27(4.5％)、737.29(3.0％)、737.27(2.6％)、735.27(1.5％)
The synthesis of compound 17
Carry out except replacing 1-3 with 4-3, except reaction, synthesizing with the method identical with compound 8.
m/z：734.28(100.0％)、735.28(57.8％)、736.28(17.0％)、736.27(4.5％)、737.29(3.0％)、737.27(2.6％)、735.27(1.5％)
The synthesis of compound 18
In round-bottomed flask, by bromo-to 2g5-2,4-N, N-phenylbenzene aniline (4-bromo-N, N-diphenylaniline) 3.7g, t-BuONa (sodium tert-butoxide) 1.4g, Pd 2(dba) 3(three (dibenzalacetone) two palladium) 0.35g, (t-Bu) 3p (tri-butyl phosphine) 0.23ml has carried out return stirring after dissolving in toluene 40ml.Confirm to react with TLC (thin layer chromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 2.47g compound 18 (productive rate is 63%).
m/z：450.17(100.0％)、451.18(34.9％)、452.18(6.1％)
The synthesis of compound 19
In round-bottomed flask, by bromo-to 2g5-2,5-N1, N1, N3, N3-tetraphenyl benzene-1,3-diamines (5-bromo-N1, N1, N3, N3-tetraphenylbenzene-1,3-diamine) 5.7g, t-BuONa (sodium tert-butoxide) 1.4g, Pd 2(dba) 3(three (dibenzalacetone) two palladium) 0.35g, (t-Bu) 3p (tri-butyl phosphine) 0.23ml has carried out return stirring after dissolving in toluene 40ml.Confirm to react with TLC (thin layerchromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 3.8g compound 19 (productive rate is 65%).
m/z：617.25(100.0％)、618.25(48.0％)、619.25(11.8％)、620.26(1.7％)、618.24(1.1％)
The synthesis of compound 20
In round-bottomed flask, by bromo-to 1.5g5-2,4-N, N-phenylbenzene aniline (4-bromo-N, N-diphenylaniline) 1.46g, t-BuONa (sodium tert-butoxide) 1.0g, Pd 2(dba) 3(three (dibenzalacetone) two palladium) 0.3g, (t-Bu) 3p (tri-butyl phosphine) 0.15ml has carried out return stirring after dissolving in toluene 30ml.Confirm to react with TLC (thin layer chromatography, tlc) and finish reaction after adding water.EA (ethanol) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 2.61g compound 20 (productive rate is 55%).
m/z：657.24(100.0％)、658.24(50.9％)、659.25(12.7％)、660.25(2.3％)
The synthesis of compound 21
Carry out except replacing 5-3 with 6-2, except reaction, synthesizing with the method identical with compound 19.
m/z：633.22(100.0％)、634.23(47.9％)、635.23(11.6％)、635.22(5.1％)、636.22(2.2％)、634.22(1.9％)、636.23(1.9％)
The synthesis of compound 22
Carry out except replacing 5-3 with 6-2, except reaction, synthesizing with the method identical with compound 20.
m/z：689.20(100.0％)、690.20(51.7％)、691.20(13.5％)、691.19(9.1％)、692.20(4.9％)、692.21(2.0％)、693.20(1.1％)、690.19(1.1％)
The synthesis of compound 23
In round-bottomed flask, by 3g5-2, bromobenzene (bromobenzene) 2.7g, t-BuONa (sodium tert-butoxide) 2.1g, Pd 2(dba) 3(three (dibenzalacetone) two palladium) 1.0g, (t-Bu) 3p (tri-butyl phosphine) 1.4ml has carried out return stirring after dissolving in toluene 100ml.Confirm to react with TLC (thin layerchromatography, tlc) and finish reaction after adding water.Utilized by organic layer EA (ethanol) to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 6-phenyl-6H-cumarone also [2,3-b] indoles (6-phenyl-6H-benzofuro [2,3-b] indole) 2.9g (productive rate is 71%).
In round-bottomed flask, by 6-phenyl-6H-cumarone also [2,3-b] indoles (6-phenyl-6H-benzofuro [2,3-b] indole) 2.9g, N-bromosuccinimide (N-Bromosuccinimide) 5.5g stirred 6 hours after dissolving in MC (methylene dichloride) 80ml at normal temperatures.Reaction is finished after confirming reaction with TLC (thin layer chromatography, tlc).MC (methylene dichloride) is utilized by organic layer to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain 2, the bromo-6-phenyl of 9-bis--6H-cumarone also [2,3-b] indoles (2,9-dibromo-6-phenyl-6H-benzofuro [2,3-b] indole) 2.9g (productive rate is 65%).
By above-mentioned 2, the bromo-6-phenyl of 9-bis--6H-cumarone also [2,3-b] indoles (2,9-dibromo-6-phenyl-6H-benzofuro [2,3-b] indole) 2.9g, pentanoic (diphenylamine) 2.4g, t-BuONa (sodium tert-butoxide) 0.9g, Pd 2(dba) 3(three (dibenzalacetone) two palladium) 0.5g, (t-Bu) 3p (tri-butyl phosphine) 1.1ml has carried out return stirring after dissolving in toluene 100ml.Confirm to react with TLC (thin layer chromatography, tlc) and finish reaction after adding water.Utilized by organic layer EA (ethanol) to carry out extracting and after filtration under diminished pressure, obtain 2.8g compound 23 (productive rate is 70%).
m/z：617.25(100.0％)、618.25(48.0％)、619.25(11.8％)、620.26(1.7％)、618.24(1.1％)
The synthesis of compound 24
Carry out except replacing 5-2 with 6-2, except reaction, synthesizing with the method identical with compound 23.
m/z：633.22(100.0％)、634.23(47.9％)、635.23(11.6％)、635.22(5.1％)、636.22(2.2％)、634.22(1.9％)、636.23(1.9％)
The synthesis of compound 25
In round-bottomed flask, by bromo-to 5.0g1-2,1-4-iodobenzene (1-bromo-4-Iodobenzene) 9.89g, t-BuONa (sodium tert-butoxide) 2.5g, Pd 2(dba) 3(three (dibenzalacetone) two palladium) 0.6g, (t-Bu) 3p (tri-butyl phosphine) 1.5ml stirs after dissolving in toluene 100ml at 80 DEG C.Confirm to react with TLC (thin layer chromatography, tlc) and finish reaction after adding water.Utilized by organic layer EA (ethanol) to carry out extracting and after filtration under diminished pressure, carry out post purification and obtain the bromo-6-of 9-(4-bromophenyl)-6H-cumarone also [2,3-b] indoles (9-bromo-6-(4-bromophenyl)-6H-benzofuro [2,3-b] indole) 2.8g (productive rate is 37%).
By bromo-for above-mentioned 9-6-(4-bromophenyl)-6H-cumarone also [2,3-b] indoles (9-bromo-6-(4-bromophenyl)-6H-benzofuro [2,3-b] indole) 2.8g, pentanoic (diphenylamine) 3.6g, t-BuONa (sodium tert-butoxide) 1.5g, Pd 2(dba) 3(three (dibenzalacetone) two palladium) 0.7g, (t-Bu) 3p (tri-butyl phosphine) 2.0ml has carried out return stirring after dissolving in toluene 100ml.Confirm to react with TLC (thin layer chromatography, tlc) and finish reaction after adding water.Utilized by organic layer EA (ethanol) to carry out extracting and after filtration under diminished pressure, obtain 3.7g compound 25 (productive rate is 62%).
m/z：617.25(100.0％)、618.25(48.0％)、619.25(11.8％)、620.26(1.7％)、618.24(1.1％)
The synthesis of compound 26
Carry out except replacing 1-2 with 3-2, except reaction, synthesizing with the method identical with compound 25.
m/z：633.22(100.0％)、634.23(47.9％)、635.23(11.6％)、635.22(5.1％)、636.22(2.2％)、634.22(1.9％)、636.23(1.9％)
The manufacture of organic illuminating element
Organic illuminating element has been manufactured according to structure described in Fig. 1.Organic illuminating element is stacked with the order from the bottom up for anode (hole injecting electrode 11)/hole injection layer 12/ hole transmission layer 13/ luminescent layer 14/ electron transfer layer 15/ negative electrode (electron injection electrode 16).
The hole injection layer 12 of following embodiment and comparative example, hole transmission layer 13, luminescent layer 14, electron transfer layer 15 employ following material.
Embodiment 1
Utilize distilled water ultrasonic cleaning to be coated with thickness to be the glass substrate of indium tin oxide (ITO) film.After distilled water cleaning terminates, Virahol, acetone, methyl alcohol equal solvent is utilized to carry out ultrasonic cleaning and have carried out drying, be delivered to plasma cleaner afterwards and utilize oxygen plasma to carry out cleaning in 5 minutes to aforesaid substrate, utilizing thermovacuum evaporator (thermal evaporator) to make thickness and be in portion on an ito substrate afterwards compound 1 film and as hole injection layer and hole transmission layer.Then, be 5% carry out adulterating and made thickness and be as above-mentioned luminescent layer with MADN (2-methyl-9,10-two (naphthalene-2-base) anthracenes): BD01 (1,6-bis-(N, N diphenyl amino) pyrene) film.Then, the thickness made as electron transfer layer is alq 3after (three (oxine) aluminium) film, making thickness is liF film and thickness be aluminium (Al) film and in glove box seal (Encapsulation) this element, made organic illuminating element thus.
Embodiment 2 to embodiment 17
Prepare organic illuminating element in the same manner as in Example 1, wherein, used compound 2 to compound 17 respectively at hole injection layer and hole transport layer and replace compound 1, made organic illuminating element thus.
Embodiment 18
Utilize distilled water ultrasonic cleaning to be coated with thickness to be the glass substrate of indium tin oxide (ITO) film.After distilled water cleaning terminates, Virahol, acetone, methyl alcohol equal solvent is utilized to carry out ultrasonic cleaning and have carried out drying, be delivered to plasma cleaner afterwards and utilize oxygen plasma to carry out cleaning in 5 minutes to aforesaid substrate, utilizing thermovacuum evaporator (thermal evaporator) thickness that portion has made as hole injection layer to be on an ito substrate afterwards 2-TNATA (4,4', 4 "-three [2-naphthylphenyl amino] triphenylamine) film and as the thickness of hole transport layer be the film of above-mentioned synthesized compound 18.Then, as luminescent layer with CBP (4,4'-two (N-carbazole)-1,1'-biphenyl): Ir (ppy) 3be 7% carry out adulterating and made thickness and be film.Then, the thickness made as electron transfer layer is tPBi (1,3,5-tri-(1-phenyl-1H-benzimidazolyl-2 radicals-Ji) benzene) film after, make thickness be liF film and thickness be aluminium (Al) film and in glove box seal (Encapsulation) this element, made organic illuminating element thus.
Embodiment 19 to embodiment 26
Prepare organic illuminating element with the method identical with above-described embodiment 18, wherein, used compound 19 to compound 26 respectively at hole transport layer and replace compound 18, having made organic illuminating element thus.
Comparative example 1
Except by NPB (N, N'-phenylbenzene-N, N'-bis-(1-naphthyl)-1,1'-biphenyl-4,4'-diamines) as outside the hole injection layer of above-described embodiment 1 and hole transport layer, made element in the same way.
Comparative example 2
Except by outside the hole transport layer of NPB (N, N'-phenylbenzene-N, N'-bis-(1-naphthyl)-1,1'-biphenyl-4,4'-diamines) as above-described embodiment 18, make element in the same way.
The performance evaluation of organic illuminating element
Keithley 2400 source measuring unit (Keithley 2400source measurement unit) is utilized to apply voltage and inject electronics and hole, and brightness when utilizing Konica Minolta (Konica Minolta) spectroradio luminance meter (CS-2000) and determine light outgoing, thus measure the performance that executed alive current density and brightness be have rated to the organic illuminating element of embodiment and comparative example under atmospheric conditions, the results are shown in table 1 and table 2.
Table 1
Table 2
As above, shown in table 1 and table 2, can confirm that its physical property of embodiments of the invention 1 to embodiment 26 is all better than comparative example 1 and comparative example 2 in all respects.
Industrial utilizability
The compound of chemical formula 1 of the present invention is owing to comprising structure and the arylamine of indoles (indole) and furans (furan) institute closed loop (ring closing), thus there is the characteristic easily transmitting electric charge, and there is high triplet energy and high glass-transition temperature, therefore, it is possible to effectively as be suitable for all colours such as redness, green, blueness, white fluorescence and phosphorescence element, hole-injection characteristics and the excellent hole-injecting material of hole transport property and/or hole mobile material.
In addition, if use the compound of above-mentioned chemical formula 1 at hole injection layer or hole transmission layer, then low driving voltage, high-level efficiency, reduce power consumption and the organic illuminating element of long life can be made.

Claims (7)

1. an organic compound, it represents with following chemical formula 1:
In above-mentioned formula,
X is O, S, Se or Te;
L 1to L 3be hydrogen independently of one another; Heavy hydrogen; Tritium; or substituted or unsubstituted C 6-C 60aryl, C 4-C 60heteroaryl, C 6-C 30arylidene, C 4-C 30heteroarylidene or C 6-C 60condensation polycyclic base;
N is the integer of 0 to 2 independently of one another, wherein, and L 1to L 3in at least one its n be more than 1 and comprise
Above-mentioned Ar 1and Ar 2be hydrogen independently of one another; Heavy hydrogen; Tritium or substituted or unsubstituted C 6-C 60aryl, C 4-C 60heteroaryl or C 6-C 60condensation polycyclic base, Ar 1and Ar 2ring can be formed.
2. organic compound according to claim 1, is characterized in that,
The compound of above-mentioned chemical formula 1 is selected from the group be made up of the compound represented with following chemical formula 2 to chemical formula 8:
X is O, S, Se or Te;
L 4to L 6be substituted or unsubstituted C independently of one another 6-C 60aryl, C 4-C 60heteroaryl, C 6-C 30arylidene, C 4-C 30heteroarylidene or C 6-C 60condensation polycyclic base;
N is the integer of 0 to 2 independently of one another, wherein, and L 4to L 6in at least one its n be more than 1;
Ar 1to Ar 7be hydrogen independently of one another; Heavy hydrogen; Tritium or substituted or unsubstituted C 6-C 60aryl, C 4-C 60heteroaryl or C 6-C 60condensation polycyclic base, adjacent Ar can form ring each other.
3. organic compound according to claim 1, is characterized in that,
The compound of above-mentioned chemical formula 1 is selected from the group be made up of following each structural formula:
4. an organic illuminating element, it is at anode (anode), negative electrode (cathode) and the compound between two electrodes containing claim 1 or two or more mixtures.
5. organic illuminating element according to claim 4, is characterized in that,
There is the structure that anode, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode stack gradually.
6. organic illuminating element according to claim 5, is characterized in that,
Above-mentioned hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer have the thickness of 10 to 1,000nm respectively.
7. organic illuminating element according to claim 4, is characterized in that,
Above-mentioned hole injection layer or hole transmission layer contain compound described in claim 1.
CN201380066353.5A 2012-12-28 2013-12-27 Novel organic compound and organic light emitting device containing same Pending CN104870424A (en)

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