CN105102408B - Novel triphenylene derivative compound and organic light-emitting element using same - Google Patents

Novel triphenylene derivative compound and organic light-emitting element using same Download PDF

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CN105102408B
CN105102408B CN201480018568.4A CN201480018568A CN105102408B CN 105102408 B CN105102408 B CN 105102408B CN 201480018568 A CN201480018568 A CN 201480018568A CN 105102408 B CN105102408 B CN 105102408B
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phenanthrene
substituted
organic illuminating
illuminating element
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CN105102408A (en
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金成勋
安贤哲
金丁善
金贤明
白善中
李殷泳
金永德
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Dongjin Semichem Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
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    • C09K2211/1011—Condensed systems

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract

The present invention relates to a novel triphenylene derivative compound and an organic light-emitting device including the same, and more particularly, to a triphenylene derivative compound having an effect of low driving voltage and excellent light-emitting efficiency and color purity characteristics when applied to an organic light-emitting device.

Description

Novel triphenylene compound and use its organic illuminating element
Technical field
The present invention relates to novel triphenylene compound and its organic illuminating element is used, more specifically, is related to And the triphenylene compound of the organic illuminating element of the excellents such as driving voltage, luminous efficiency and excitation purity can be manufactured And use its organic illuminating element.
Background technology
In recent years, the organic illuminating element that low voltage drive can be carried out using emissive type and the master as flat panel displaying element The liquid crystal display (LCD, liquid crystal display) of stream is compared, and since field angle, contrast etc. are excellent, is not needed to Backlight can carry out light weight and slim manufacture, and also advantageous in terms of power consumption, and color reproduction range is wide, therefore as a new generation Display element and attract attention.
In general, organic illuminating element have comprising cathode (electron injection electrode), anode (hole injecting electrode) and The structure of organic layer between above-mentioned two electrode.At this point, organic layer is in addition to luminescent layer (EML, light emitting layer) It may include hole injection layer (HIL, hole injection layer), hole transmission layer (HTL, hole transport in addition Layer), electron transfer layer (ETL, electron transport layer) or electron injecting layer (EIL, electron Injection layer), consider from the characteristics of luminescence of luminescent layer, can further include electronic barrier layer (EBL, electron Blocking layer) or hole blocking layer (HBL, hole blocking layer).
If the organic illuminating element to such structure applies electric field, hole can be injected from anode and be injected from cathode Electronics, hole and electronics carry out compound (recombination) via hole transmission layer and electron transfer layer in luminescent layer respectively And form luminescent excitons (exitons).The luminescent excitons of formation while ground state (ground states) transition to sending out Light.In order to improve the efficiency of luminance and stability, sometimes to luminescent layer (main body) doping luminescent pigment (dopant).
As the substance used in the luminescent layer of organic illuminating element, it is known to multiple compounds, but using at present In the case of the organic illuminating element for the luminescent substance known, due to high driving voltage, poor efficiency and short life, in functionization Aspect exists a large amount of difficult.Therefore, following effort is carried out always：It is opened by using the substance with the excellent characteristics of luminescence Hair has low voltage drive, high efficiency and the organic illuminating element of long-life.
Invention content
Technical task
In order to solve the problems, such as conventional art as described above, the object of the present invention is to provide can improve organic light emission The triphenylene compound of the characteristics such as driving voltage, luminous efficiency, the excitation purity of element and include above-mentioned benzophenanthrene derive The organic illuminating element of compounds.
The method to solve the problem
To achieve these goals, the present invention provides the triphenylene compound represented by following chemical formula 1：
[chemical formula 1]
In above-mentioned chemical formula 1,
R1To R14It is each independently selected from the alkyl, substituted or non-substituted by substituted or non-substituted carbon atom number 1 to 20 The cycloalkyl of carbon atom number 3 to 20, substituted or non-substituted carbon atom number 3 to 20 Heterocyclylalkyl, substituted or non-substituted The aryl of carbon atom number 6 to 40, the heteroaryl of substituted or non-substituted carbon atom number 3 to 40, substituted or non-substituted carbon atom The alkoxy of number 1 to 30, the aryloxy group of substituted or non-substituted carbon atom number 6 to 30, substituted or non-substituted carbon atom number 1 to 30 alkyl amino, the cycloalkyl amino of substituted or non-substituted carbon atom number 3 to 20, substituted or non-substituted carbon atom number 3 Arylamino, the substituted or non-substituted carbon atom of heterocyclalkylamino, substituted or non-substituted carbon atom number 6 to 30 to 20 The heteroaryl amino of number 6 to 30, the aryl alkyl amino of substituted or non-substituted carbon atom number 6 to 30, substituted or non-substituted carbon The aIkylsilyl groups of atomicity 1 to 30, the arylsilyl groups of substituted or non-substituted carbon atom number 6 to 30, substitution or non- The group that substituted alkenyl, substituted or non-substituted alkynyl, cyano, halogen, deuterium and hydrogen forms.
In addition, the present invention provides the organic illuminating element for including above-mentioned triphenylene compound.
Invention effect
The organic illuminating element using novel triphenylene compound of the present invention has driving voltage, luminous efficiency With the effect of the excellents such as excitation purity.
Description of the drawings
Fig. 1 is the sectional view for the structure for representing organic illuminating element according to an embodiment of the invention.
Specific embodiment
Hereinafter, the present invention is described in detail.
The present invention provides the triphenylene compound represented by following chemical formula 1：
[chemical formula 1]
In above-mentioned chemical formula 1,
R1To R14It is each independently selected from the alkyl, substituted or non-substituted by substituted or non-substituted carbon atom number 1 to 20 The cycloalkyl of carbon atom number 3 to 20, substituted or non-substituted carbon atom number 3 to 20 Heterocyclylalkyl, substituted or non-substituted The aryl of carbon atom number 6 to 40, the heteroaryl of substituted or non-substituted carbon atom number 3 to 40, substituted or non-substituted carbon atom The alkoxy of number 1 to 30, the aryloxy group of substituted or non-substituted carbon atom number 6 to 30, substituted or non-substituted carbon atom number 1 to 30 alkyl amino, the cycloalkyl amino of substituted or non-substituted carbon atom number 3 to 20, substituted or non-substituted carbon atom number 3 Arylamino, the substituted or non-substituted carbon atom of heterocyclalkylamino, substituted or non-substituted carbon atom number 6 to 30 to 20 The heteroaryl amino of number 6 to 30, the aryl alkyl amino of substituted or non-substituted carbon atom number 6 to 30, substituted or non-substituted carbon The aIkylsilyl groups of atomicity 1 to 30, the arylsilyl groups of substituted or non-substituted carbon atom number 6 to 30, substitution or non- The group that substituted alkenyl, substituted or non-substituted alkynyl, cyano, halogen, deuterium and hydrogen forms.
The specific example of substituent group, that is, alkyl used in the present invention, can enumerate methyl, ethyl, propyl, isobutyl Base, sec-butyl, tertiary butyl, amyl, isopentyl, hexyl, heptyl, octyl group, octadecyl, trichloromethyl, trifluoromethyl etc., it is above-mentioned More than one hydrogen atom in alkyl can be by D-atom, halogen atom, hydroxyl, nitro, cyano, trifluoromethyl, silicyl (this When, referred to as " aIkylsilyl groups "), substituted or non-substituted amino (- NH2 ,-NH (R) ,-N (R') (R "), wherein, R, R' and R " is each independently the alkyl (at this point, be known as " alkyl amino ") of carbon atom number 1 to 24), amidino groups, diazanyl, hydrazone group, carboxyl, Sulfonic group, phosphate, the alkyl of carbon atom number 1 to 24, the halogenated alkyl of carbon atom number 1 to 24, carbon atom number 2 to 24 alkene Base, the alkynyl of carbon atom number 2 to 24, the miscellaneous alkyl of carbon atom number 1 to 24, the aryl of carbon atom number 5 to 24, carbon atom number 6 to The heteroaryl alkyl substitution of 24 aryl alkyl, the heteroaryl of carbon atom number 3 to 24 or carbon atom number 3 to 24.
As the substituent group used in the compound of the present invention the i.e. specific example of alkoxy, methoxyl group, second can be enumerated Oxygroup, propoxyl group, isobutoxy, sec-butoxy, amoxy, isoamoxy, hexyloxy etc., they can be by the feelings with abovementioned alkyl The same substituent group substitution of condition.
As the substituent group used in the compound of the present invention the i.e. specific example of aryl, phenyl, 2- methyl can be enumerated Phenyl, 3- aminomethyl phenyls, 4- aminomethyl phenyls, 4- ethylphenyls, adjacent xenyl, xenyl, to xenyl, 4- methyl biphenyls Base, 4- ethyl biphenyls base, ortho-terphenyl base, meta-terphenyl base, para-terpheny base, 1- naphthalenes, 2- naphthalenes, 1- methyl naphthalene, 2- The aromatic groups such as methyl naphthalene, anthryl, phenanthryl, pyrenyl, fluorenyl, tetrahydro naphthyl, they can be by the situation with abovementioned alkyl Same substituent group substitution.
As the substituent group used in the compound of the present invention the i.e. specific example of heteroaryl, there are pyridyl group, pyrimidine radicals, three Piperazine base, indyl, quinolyl, pyrrolidinyl, piperidyl, morpholinyl, piperazinyl, carbazyl,Oxazolyl,Di azoly, benzoOxazolyl, thiazolyl, thiadiazolyl group, benzothiazolyl, triazolyl, imidazole radicals, benzimidazolyl etc., one in above-mentioned heteroaryl A above hydrogen atom can be replaced by the substituent group identical with the situation of abovementioned alkyl.
As the substituent group used in the compound of the present invention the i.e. specific example of alkenyl, have to acetamido benzene sodium antimonate (stibenyl), styryl etc. is connected with the alkenyl of aryl；As the specific example of cycloalkyl, there are cyclopenta, cyclohexyl etc., But not limited to this.
The substituent group used in the compound of the present invention i.e. arylamino can enumerate diphenyl amino, phenyl napthyl ammonia Base, phenylbiphenylyl amino, naphthalene xenyl amino, dinaphthyl amino, dibiphenylyl amino, two anthryl amino, 3- methyl-benzene Base amino, 4- methyl-naphthyl-amino, 2- Methvl-biphenyls amino, 9- methyl-anthryl amino, xylyl amino, phenyl first Phenyl amino, triphenylamino phenyl amino, phenylbiphenylyl aminophenyiamino, naphthylphenyl aminophenyl xenyl amino Deng, but not limited to this.
In the present invention, term " substituted or non-substituted " is meant, is chosen free cyano, halogen, hydroxyl, nitro, alkane Base, cycloalkyl, Heterocyclylalkyl, aralkyl, alkoxy, alkyl amino, arylamino, heteroaryl amino, aryl alkyl amino, alkyl One or more of group that silicyl, arylsilyl groups, aryloxy group, aryl, heteroaryl, germanium, phosphorus, boron, hydrogen and deuterium form takes It is substituted or non-substituted for base.
Specifically, the above-mentioned triphenylene compound of the present invention is preferably selected from the group represented by following chemical formula, But not limited to this.
In addition, the above-mentioned triphenylene compound of the present invention can be manufactured by the manufacturing method that following schematic diagrames are recorded.
[schematic diagram]
In addition, the present invention provides the organic illuminating element for including above-mentioned triphenylene compound.
In addition, the organic illuminating element of the present invention is characterized in that, between the anode and cathode, comprising selected from by shining The group that layer, hole injection layer, hole transmission layer, hole blocking layer, electron transfer layer, electron injecting layer and electronic barrier layer form In more than one layer, and above-mentioned triphenylene compound is contained in layer more than at least one of above-mentioned layer.
Shining between above-mentioned anode and cathode is preferably contained in particular according to the triphenylene compound of the present invention Layer.
In addition, the layer between anode and cathode can be using the mode that is deposited or solwution method (solution process) come shape Into.
In addition, it the method can be widely used in the display element comprising above-mentioned organic illuminating element, display device and monochrome Or white illumination element etc..
In addition, the manufacturing method of above-mentioned organic illuminating element according to the present invention is described in more detail, content is such as Under.
Organic illuminating element according to the present invention may include that hole is injected between anode (anode) and cathode (cathod) Layer (HIL), hole transmission layer (HTL), luminescent layer (EML), electron transfer layer (ETL), electron injecting layer (EIL) etc. more than one Organic thin film layer.
First, on substrate top, vapor deposition has anode (anode) the electrode substance of high work function and forms anode.This When, the substrate used in conventional organic illuminating element can be used in aforesaid substrate, particularly preferably using mechanical strength, thermostabilization Property, the transparency, surface smoothness, handling easiness and the excellent organic substrate or transparent plastic substrate of water proofing property.In addition, conduct Anode electrode substance, the tin indium oxide (ITO) that can be used transparent and electrically conductive excellent, indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO) etc..Above-mentioned anode electrode can be deposited with substance using conventional anode forming method, it is specific and Speech, can be deposited using vapour deposition method or sputtering method.
Later, on above-mentioned anode electrode top, using vacuum vapour deposition, spin-coating method, casting method, LB (Langmuir- Blodgett (Lang Gemiaoer-Blodget)) method the methods of formed hole injection layer (HIL) substance, but from be easy to get uniformly Film quality and be not likely to produce pin hole etc. consideration, formed preferably by vacuum vapour deposition.Utilizing above-mentioned vacuum vapour deposition shape In the case of hole injection layer, evaporation condition is according to the compound of material as hole injection layer, target hole injection layer Structure and thermal characteristics etc. and it is different, but in general it is preferred that suitably selected in following range：50-500 DEG C of vapor deposition temperature Degree, 10-8-10-3The vacuum degree of torr,Evaporation rate,- 5 μm of film thickness.
Well known substance can be used in above-mentioned hole injection layer substance, by way of example, can inject following substance as hole Layer substance：The phthalocyanine compounds such as the copper phthalocyanine described in U.S. Patent No. 4,356,429 are used as star burst (star burst Type) TCTA (4,4', 4 "-three (N- carbazyls) triphenylamine) of amine derivative class, m-MTDATA ((the 3- first of 4,4', 4 "-three Base phenyl amino) triphenylamine), m-MTDAPB (4,4', 4 "-three (3- MethYlphenylaminos) phenoxy group benzene, advanced material (Advanced Material), 6, p677 (1994)), HI-406 (N1, N1'- (biphenyl -4,4'- diyls) bis- (N1- (naphthalene -1- Base)-N4, N4- diphenyl benzene -1,4- diamines) etc..
Then, on above-mentioned hole injection layer top, using shape the methods of vacuum vapour deposition, spin-coating method, casting method, LB methods Into hole transmission layer (HTL) substance, but from the aspect of being easy to get uniform film quality and being not likely to produce pin hole, preferably by true Empty vapour deposition method is formed.In the case where forming hole transmission layer using above-mentioned vacuum vapour deposition, evaporation condition is according to using Compound and it is different, but in general it is preferred that selected under equal condition and range when with forming hole injection layer.
In addition, above-mentioned hole transmission layer substance is not particularly limited, the chemical combination represented by the chemical formula 1 of the present invention can be used Object is arbitrarily selected from known substance conventional used in hole transmission layer and is used.Specifically, in addition to the present invention's Other than compound represented by chemical formula 1, the carbazoles such as N- phenyl carbazoles, polyvinylcarbazole can be used in above-mentioned hole transmission layer substance Derivative；N, N'- bis- (3- aminomethyl phenyls)-N, N'- diphenyl-[1,1- xenyls] -4,4'- diamines (TPD), N.N'- bis- (naphthalene -1- bases)-N,N' diphenyl benzidine (α-NPD) etc. has conventional amine derivative of aromatic condensation ring etc..
Later, it on above-mentioned hole transmission layer top, is formed using the methods of vacuum vapour deposition, spin-coating method, casting method, LB methods Luminescent layer (EML) substance, but from the aspect of being easy to get uniform film quality and being not likely to produce pin hole, preferably by vacuum evaporation Method is formed.In the case where forming luminescent layer using above-mentioned vacuum vapour deposition, evaporation condition is different according to the compound used, But it in general it is preferred that is selected under condition and range almost the same when with forming hole injection layer.In addition, above-mentioned luminescent layer material Material can be used alone the present invention chemical formula 1 represented by compound or as main body.
Compound represented by above-mentioned chemical formula 1 or two or more mixtures are being used as light emitting host and dopant In the case of, phosphorescence or fluorescent dopants and main body are can be used simultaneously to form luminescent layer.At this point, as fluorescent dopants, can make With IDE102, IDE105 or the BD142 for being purchased from light extraction company (Idemitsu companies)；It, can will be green as phosphorescent dopant Phosphorescent dopant Ir (ppy) 3 (three (2- phenylpyridines) close iridium, fac-tris (2-phenylpyridine) iridium), blue (bis- (4,6- difluorophenyl pyridinato-N, C2') pyridinecarboxylics close iridium, iridium (III) bis [(4,6- to phosphorescent dopant FIrpic Di-fluorophenyl)-pyridinato-N, C2'] picolinate), the red phosphorescent dopant RD61 of UDC companies etc. into The common vacuum evaporation (doping) of row.The doping concentration of dopant is not particularly limited, but relative to 100 parts by weight of main body, doping The concentration of object is preferably 0.01-15 parts by weight.
In addition, in the case where phosphorescent dopant is used for luminescent layer simultaneously, triplet excitons or hole are expanded in order to prevent The phenomenon that being dissipated to electron transfer layer (HTL) adds preferably by vacuum vapour deposition or spin-coating method and hole inhibition material is laminated (HBL).At this point, workable hole inhibiting substances are not particularly limited, it can be from the known object for having been used as hole inhibition material It arbitrarily selects and uses in matter.For example, it can enumerateOxadiazole derivative or triazole derivative, phenanthroline derivative or day Hole described in this Unexamined Patent 11-329734 (A1) inhibits material etc., and as representative, Balq, phenanthroline can be used (phenanthrolines) based compound (such as：UDC company BCP) etc..
On luminescent layer top as formed above, electron transfer layer (ETL) material can be formed, at this point, above-mentioned electron transfer layer It is formed using the methods of vacuum vapour deposition, spin-coating method or casting method, is particularly preferably formed using vacuum vapour deposition.
Above-mentioned electron transport layer materials, which have the function of to stablize, to be transmitted by electron injection electrode (cathode) injected electrons, Type is not particularly limited, for example, quinoline can be used, three (8- quinoline) aluminium (Alq3) especially can be used.In addition, in electricity The substance i.e. electron injecting layer (EIL) for having the function of that electronics is made easily to be injected from cathode can be laminated in sub- transport layer top, as Electron injecting layer substance, using LiF, NaCl, CsF, Li2O, the substances such as BaO.
In addition, the evaporation condition of above-mentioned electron transfer layer (ETL) is different according to used compound, but it is general and It is selected under speech, preferably condition and range almost the same when with forming hole injection layer.
Later, on above-mentioned electron transfer layer top, electron injecting layer (EIL) substance can be formed, utilizes vacuum evaporation at this time Conventional electron injecting layer substance is formed on the methods of method, spin-coating method, casting method above-mentioned electron transfer layer, particularly preferably using true Empty vapour deposition method is formed.
Finally, on electron injecting layer top, using forming cathode formation metal the methods of vacuum vapour deposition or sputtering method, So as to as cathode (cathode).Wherein, as cathode formation metal, can be used the metal with low work function, alloy, Conductive compound and their mixture.As specific example, have lithium (Li), magnesium (Mg), aluminium (Al), aluminium-lithium (Al-Li), Calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) etc..In addition, top emitting light-emitting component in order to obtain, it is possible to use utilize The infiltration type cathode of ITO, IZO.
The organic illuminating element of the present invention is not only with anode (anode), hole injection layer (HIL), hole transmission layer (HTL), luminescent layer (EML), electron transfer layer (ETL), electron injecting layer (EIL), cathode (cathode) structure organic light emission Element can be the structure of the organic illuminating element with various structures, as needed, can also be further formed one layer or 2 layers Middle layer.
As above the thickness of organic thin film layer formed according to the present invention can degree as needed be adjusted, preferably 10-1,000nm, more preferably 20-150nm.
Hereinafter, in order to help to understand the present invention, the preferred synthesis example and embodiment of the compound of the present invention are provided, but Following synthesis examples and embodiment only illustrate the present invention, and the scope of the present invention is not limited to following synthesis examples and embodiment.
[synthesis example]
Synthesis example 1-1. synthesizes the chloro- 3,4- dihydros -2- formaldehyde of 1-
Under stream of nitrogen gas, to reactor input dimethylformamide (DMF) 8.4g (114.9mmol), METHYLENE CHLORIDE (MC)40ml.Reaction temperature is cooled to 0-5 DEG C, phosphorus oxychloride (POCl is then slowly added dropwise3) 14g (91.3mmol), and It is stirred 2 hours under room temperature.Reaction temperature is cooled to 0-5 DEG C again, then slowly puts into the α-four for being dissolved in METHYLENE CHLORIDE 50ml Hydrogen naphthalenone (α-tetralone) 8.76g (59.9mmol) solution.After input, stir 16 hours at normal temperatures.It will react molten Liquid pours into ice-cold sodium carbonate (Na2CO3) aqueous solution (satd) 200ml, and additional input METHYLENE CHLORIDE 200ml.Stirring is straight always It is no longer generated to gas.After extraction, water layer is extracted again with METHYLENE CHLORIDE 250ml.With magnesium sulfate (MgSO4) dry organic Layer, then filtering and concentrating obtain chloro- 3,4- dihydros -2- formaldehyde (1-chloro-3, the 4-dihydro-2- of red liquid 1- Carbaldehyde) 10.5g (54.7mmol, 91.3%).
MS(EI)(m/z)：[M+]192
Synthesis example 1-2. synthesizes 1- phenyl -3,4- dihydro -2- formaldehyde
Under stream of nitrogen gas, to chloro- 3, the 4- dihydros -2- formaldehyde 920mg (4.78mmol) of reactor input 1-, phenylboric acid (phenylbronic acid) 640mg (5.26mmol), tetrabutylammonium bromide (tetrabutyl ammonium bromide) 1.54g (4.78mmol), acid chloride (II) (Pd (OAc)2) 21.5mg (0.096mmol), potassium carbonate (K2CO3) aqueous solution, then It is stirred 3 hours at 45 DEG C.If reaction terminates, it is cooled to room temperature, then puts into water, carries out layer separation.It is put into water layer Then ethyl acetate is extracted again.With magnesium sulfate (MgSO4) dry organic layer, then filtering and concentrating and carry out silicagel column Separation obtains yellow solid 1- phenyl -3,4- dihydro -2- formaldehyde (1-phenyl-3,4-dihydro-2-carbaldehyde) 1.0g (4.42mmol, 89.4%).
MS(EI)(m/z)：[M+]234
Synthesis example 1-3. synthesizes 3- acetenyl -4- phenyl -1.2- dialins
Under stream of nitrogen gas, diisopropylamine (diisopropylamine) 753ul (5.37mmol) is put into reactor, so Postcooling is to 0 DEG C.N-BuLi (n-butyllithium) solution 3.2ml (5.1mmol, 1.6M hexane solution) is slowly added dropwise Afterwards, LDA solution is synthesized by stirring 10 minutes.After reaction temperature is cooled to -78 DEG C, (trimethyl silyl is slowly added dropwise Base) diazomethane ((trimethylsilyl) diazomethane) solution 2.5ml (5.0mmol, 2M hexane solution).Identical At a temperature of stir 30 minutes, be then slowly added dropwise and 1- phenyl -3,4- dihydro -2- formaldehyde 1.0g (4.27mmol) be dissolved in tetrahydrochysene furan It mutters the solution of (THF) 5ml.Be to slowly warm up to room temperature, then stir 3 hours and reaction was completed, and put into water come terminate reaction.It will Reaction solution carries out layer separation, then carries out 2 extractions to water layer with ethyl acetate.With magnesium sulfate (MgSO4) drying organic layer, Then filtering and concentrating and utilization developing solvent n-hexane:Ethyl acetate (95:5) silica gel post separation is carried out, obtains water white transparency liquid Body 3- acetenyls -4- phenyl -1.2- dihydronaphthalene (3-ethynyl-4-phenyl-1,2-dihydronaphthalene) 778mg (3.38mmol, 79.1%).
MS(EI)(m/z)：[M+]230
Synthesis example 1-4. synthesis 5,6- dihydros-benzo [c] is luxuriant and rich with fragrance
Under stream of nitrogen gas, to reactor input 3- acetenyl -4- phenyl -1,2- dihydronaphthalene 528mg (2.3mmol), chlorine Change platinum (II) (PtCl2) 26.6mg (0.1mmol), toluene 10ml, then stirred 24 hours at 80 DEG C.If reaction terminates, Solvent is then removed by vacuum distillation, then carries out silica gel post separation using developing solvent n-hexane, obtains white solid 5,6- Dihydro-benzo [c] phenanthrene (5,6-dihydro-benzo [c] phenanthrene) 380.1mg (1.65mmol, 72.1%).
MS(EI)(m/z)：[M+]230
The bromo- 5,6- dihydros of synthesis example 1-5. synthesis 8--benzo [c] is luxuriant and rich with fragrance
Under stream of nitrogen gas, 5,6- dihydros-benzo [c] phenanthrene 10g (43.4mmol), METHYLENE CHLORIDE are put into reactor 100ml.Reaction temperature is cooled to 0 DEG C, is then slowly added dropwise bromine (Br2) 7.63g (47.7mmol) is diluted in METHYLENE CHLORIDE The solution of 76ml.After reaction temperature is warming up to room temperature, stir 6 hours.To reactor input sodium thiosulfate (N2S2O3) water-soluble After liquid, layer separation is carried out, then water layer is extracted with METHYLENE CHLORIDE.With magnesium sulfate (MgSO4) dry organic layer, then mistake Filter is concentrated and is recrystallized using METHYLENE CHLORIDE and methanol, obtains bromo- 5, the 6- dihydros of yellow solid 8--benzo [c] phenanthrene (8- Bromo-5,6-dihydro-benzo [c] phenanthrene) 11.3g (36.6mmol, 84.2%).
MS(EI)(m/z)：[M+]308
Synthesis example 1-6. synthesis chemical formulas (6)
Under stream of nitrogen gas, to bromo- 5, the 6- dihydros of reactor input 8--benzo [c] phenanthrene 1.0g (3.2mmol), 10- phenyl Anthracene -9- ylboronic acids (10-phenylanthracen-9-yl boronic acid) 1.1g (3.9mmol), tetrakis triphenylphosphine palladium (0)(Pd(PPh3)4) 0.19g (0.16mmol), potassium carbonate (K2CO3) 1.3g (9.1mmol), toluene 10ml, tetrahydrofuran (THF) 10ml, Purified Water 2ml, then carry out reflux cooling.If reaction terminate, be cooled to room temperature, and to reaction solution into Row layer separation.2 extractions are carried out to water layer with ethyl acetate.With magnesium sulfate (MgSO4) dry organic layer, then filtering and concentrating is simultaneously Utilize developing solvent n-hexane:Ethyl acetate (90:10) progress silica gel post separation, acquisition white solid 8- (10'- phenylanthracenes- 9'- yls) -5,6- dihydros-benzo [c] phenanthrene (8- (10'-phenylanthracen-9'-yl) -5,6-dihydro-benzo [c] Phenanthrene) 1.2g (2.5mmol, 77.2%).
MS(EI)(m/z)：[M+]482
Synthesis example 2. synthesizes chemical formula (31)
It is synthesized using the method identical with synthesis example 1-6, obtains white solid 8- (10'- naphthyl anthracene -9'- bases) -5, 6- dihydros-benzo [c] phenanthrene (8- (10'-naphthyl-anthracen-9'-yl) -5,6-dihydro-benzo [c] Phenanthrene) 1.1g (2.1mmol, 69.1%).
MS(EI)(m/z)：[M+]532
Synthesis example 3. synthesizes chemical formula (32)
It is synthesized to obtain white solid 8- (10'- (2 "-naphthalene) anthracenes -9'- using the method identical with synthesis example 1-6 Base) -5,6- dihydros-benzo [c] phenanthrene (8- (10'- (2 "-naphthryl)-anthracen-9'-yl) -5,6-dihydro- Benzo [c] phenanthrene) 1.3g (2.4mmol, 75.2%).
MS(EI)(m/z)：[M+]532
Synthesis example 4. synthesizes chemical formula (33)
It is synthesized using the method identical with synthesis example 1-6, obtains white solid 8- (10'- (9 "-phenanthryl) anthracenes -9'- Base) -5,6- dihydros-benzo [c] phenanthrene (8- (10'- (9 "-phenanthryl) anthracen-9'-yl) -5,6-dihydro- Benzo [c] phenanthrene) 1.2g (2.0mmol, 62.7%).
MS(EI)(m/z)：[M+]582
Synthesis example 5. synthesizes chemical formula (46)
It is synthesized using the method identical with synthesis example 1-6, acquisition white solid 8- (4'- (10 "-phenylanthracene -9 " - Base) phenyl) -5,6- dihydros-benzo [c] phenanthrene (8- (4'- (10 "-phenylanthracen-9 "-yl) phenyl) -5,6- Dihydro-benzo [c] phenanthrene) 1.2g (2.2mmol, 66.1%).
MS(EI)(m/z)：[M+]559
Synthesis example 6. synthesizes chemical formula (51)
It is synthesized using the method identical with synthesis example 1-6, acquisition white solid 8- (3'- (10 "-phenylanthracene -9 " - Base) phenyl) -5,6- dihydros-benzo [c] phenanthrene (8- (3'- (10 "-phenyl-anthracen-9 "-yl) phenyl) -5,6- Dihydro-benzo [c] phenanthrene) 1.0g (1.7mmol, 53.7%).
MS(EI)(m/z)：[M+]559
Synthesis example 7. synthesizes chemical formula (1)
It replaces bromo- 5, the 6- dihydrobenzos [c] of 8- luxuriant and rich with fragrance using chloro- 5,6- dihydrobenzos [c] phenanthrene of 4-, in addition to this, utilizes The method identical with synthesis example 1-6 is synthesized, and obtains chartreuse solid 4- (10- phenylanthracene -9- bases) -5,6- dihydros-benzene And [c] phenanthrene (4- (10-phenylanthracen-9-yl) -5,6-dihydrobenzo [c] phenanthrene) 0.8g (1.7mmol, 33.7%).
MS(EI)(m/z)：[M+]483
Synthesis example 8. synthesizes chemical formula (8)
It replaces bromo- 5, the 6- dihydrobenzos [c] of 8- luxuriant and rich with fragrance using bromo- 5,6- dihydrobenzos [c] phenanthrene of 10-, in addition to this, utilizes The method identical with synthesis example 1-6 is synthesized, and obtains shallow white solid 10- (10- phenylanthracene -9- bases) -5,6- dihydros-benzo [c] phenanthrene (10- (10-phenylanthracen-9-yl) -5,6-dihydrobenzo [c] phenanthrene) 1.5g (3.1mmol, 57.4%).
MS(EI)(m/z)：[M+]483
Synthesis example 9. synthesizes chemical formula (12)
It replaces bromo- 5, the 6- dihydrobenzos [c] of 8- luxuriant and rich with fragrance using bromo- 5,6- dihydrobenzos [c] phenanthrene of 10-, in addition to this, utilizes The method identical with synthesis example 1-6 is synthesized, and obtains chartreuse solid 3- (10- (2- naphthalenes)-anthracene -9- bases) -5,6- bis- Hydrogen-benzo [c] phenanthrene (3- (10- (2-naphthyl)-anthracen-9-yl) -5,6-dihydrobenzo [c] Phenanthrene) 1.1g (2.1mmol, 43.8%).
MS(EI)(m/z)：[M+]533
Synthesis example 10. synthesizes chemical formula (165)
It replaces bromo- 5, the 6- dihydrobenzos [c] of 8- luxuriant and rich with fragrance using iodo- 5,6- dihydrobenzos [c] phenanthrene of 5-, in addition to this, utilizes The method identical with synthesis example 1-6 is synthesized, and obtains chartreuse solid 7- (10- (2- naphthalenes)-anthracene -9- bases) -5,6- bis- Hydrogen-benzo [c] phenanthrene (7- (10- (2-naphthyl)-anthracen-9-yl) -5,6-dihydrobenzo [c] Phenanthrene) 0.9g (1.7mmol, 71.7%).
MS(EI)(m/z)：[M+]533
Synthesis example 11. synthesizes chemical formula (191)
It replaces bromo- 5, the 6- dihydrobenzos [c] of 8- luxuriant and rich with fragrance using bromo- 5,6- dihydrobenzos [c] phenanthrene of 2-, in addition to this, utilizes The method identical with synthesis example 1-6 is synthesized, and obtains chartreuse solid 2- (10- (2- naphthalenes)-anthracene -9- bases) -5,6- bis- Hydrogen-benzo [c] phenanthrene (2- (10- (2-naphthyl)-anthracen-9-yl) -5,6-dihydrobenzo [c] Phenanthrene) 1.0g (1.9mmol, 54.3%).
MS(EI)(m/z)：[M+]533
Synthesis example 12. synthesizes chemical formula (18)
Under stream of nitrogen gas, (7,8- dihydrobenzos [c] phenanthrene -3- bases)-boric acid 3.00g is put into reactor (10.9mmol), 9,10- dibromoanthracenes 1.5g (4.6mmol), tetrakis triphenylphosphine palladium (0) (Pd (PPh3)4)0.21g (0.2mmol), potassium carbonate (K2CO3) 3.8g (27.4mmol), toluene 60ml, tetrahydrofuran (THF) 60ml, Purified Water 12ml, so Carry out returned cold but afterwards.If reaction terminates, it is cooled to room temperature, and layer separation is carried out to reaction solution.With ethyl acetate pair Water layer carries out 2 extractions.With magnesium sulfate (MgSO4) dry organic layer, then filtering and concentrating and utilize developing solvent n-hexane:Second Acetoacetic ester (60:10) progress silica gel post separation, acquisition white solid 9, bis- (5,6- dihydrobenzos [c] phenanthrene -3- bases) anthracenes of 10- (9, 10-bis- (5,6-dihydrobenzo [c] phenanthren-3-yl) anthracene) 1.2g (1.9mmol, 41.5%).
MS(EI)(m/z)：[M+]635
Synthesis example 13. synthesizes chemical formula (183)
(7,8- dihydros-benzo [c] phenanthrene -6- bases) boric acid is used to replace (7,8- dihydrobenzos [c] phenanthrene -3- bases) boric acid, In addition to this, it is synthesized using the method identical with synthesis example 11, obtains white solid 9, bis- (7, the 8- dihydrobenzos of 10- [c]-phenanthrene -5- bases) anthracene (9,10-bis (7,8-dihydrobenzo [c] phenanthren-5-yl)-anthracene) 0.9g (1.4mmol, 31.1%).
MS(EI)(m/z)：[M+]635
Synthesis example 14. synthesizes chemical formula (200)
(7,8- dihydros-benzo [c] phenanthrene -6- bases) boric acid is used to replace (7,8- dihydrobenzos [c] phenanthrene -3- bases) boric acid, In addition to this, it is synthesized using the method identical with synthesis example 11, obtains white solid 9, bis- (5, the 6- dihydrobenzos of 10- [c]-phenanthrene -2- bases) anthracene (9,10-bis (5,6-dihydrobenzo [c] phenanthren-2-yl)-anthracene) 1.7g (2.7mmol, 58.7%).
MS(EI)(m/z)：[M+]635
Bis- bromo- 5,6- dihydros of synthesis example 15-1. synthesis 3,8--benzo [c] is luxuriant and rich with fragrance
Under stream of nitrogen gas, 5,6- dihydros-benzo [c] phenanthrene 10g (43.4mmol), METHYLENE CHLORIDE are put into reactor 100ml.Reaction temperature is cooled to 0 DEG C, is then slowly added dropwise bromine (Br2) 15.26g (95.4mmol) is diluted in METHYLENE CHLORIDE The solution of 150ml.After reaction temperature is warming up to room temperature, stir 6 hours.To reactor input sodium thiosulfate (N2S2O3) water After solution, layer separation is carried out, then water layer is extracted with METHYLENE CHLORIDE.With magnesium sulfate (MgSO4) drying organic layer, then Filtering and concentrating is simultaneously recrystallized using METHYLENE CHLORIDE and methanol, obtains yellow solid 3, bis- bromo- 5,6- dihydros of 8--benzo [c] Phenanthrene (3,8-dibromo-5,6-dihydro-benzo [c] phenanthrene) 12.0g (31.0mmol, 71.4%).
MS(EI)(m/z)：[M+]388
Synthesis example 15. synthesizes [chemical formula 203]
(7,8- is replaced using (10- (2- naphthalenes) anthracene -9- bases) boric acid and 3,8- bis- bromo- 5,6- dihydros-benzo [c] phenanthrene Dihydrobenzo [c] phenanthrene -3- bases) boric acid and 9,10- dibromoanthracene, in addition to this, are closed using the method identical with synthesis example 11 Into, acquisition chartreuse solid 3, bis- (10- (2- naphthalenes) anthracene -9- bases) -5, the 6- dihydros of 8--benzo [c] phenanthrene (2- (10- (2- Naphthyl) anthracen-9-yl) -5,6-dihydrobenzo [c] phenanthrene) 1.2g (1.4mmol, 40.0%).
MS(EI)(m/z)：[M+]836
Synthesis example 16. synthesizes chemical formula (131)
Under stream of nitrogen gas, 3,8-, bis- bromo- 5,6- dihydros-benzo [c] phenanthrene 10g (25.8mmol), 9H- is put into reactor Carbazole (9H-carbazole) 10.9g (57.3mmol), cupric iodide (CuI) 1.1g (5.7mmol), tripotassium phosphate 24.3g (114.6mmol), 1,2- diaminocyclohexanes 0.7g (5.7mmol), 1,4- bis-Then alkane 100ml is carrying out reflux cooling While stir 36 hours.If reaction terminates, it is filtered, solvent is then removed by decompression.Silicon is carried out to reactant Rubber column gel column detaches, and obtains pistac solid 9,9'- (5,6- dihydrobenzos [c]-phenanthrene -3,8- diyls)-bis- (9H- carbazoles) (9,9'- (5,6-dihydrobenzo [c] phenanthrene-3,8-diyl) bis (9H-carbazole) 3.2g (5.6mmol, 21.9%).
MS(EI)(m/z)：[M+]561
Synthesis example 17. synthesizes chemical formula (134)
It is synthesized using the method identical with synthesis example 15, obtains pistac solid 3,3'- (5,6- dihydros-benzo [c] phenanthrene -3,8- diyls) bis- (9- phenyl -9H- carbazoles) (3,3'- (5,6-dihydrobenzo [c] phenanthrene-3,8- Diyl) bis (9-phenyl-9H-carbazole)) 5.4g (9.5mmol, 36.7%).
MS(EI)(m/z)：[M+]713
Synthesis example 18. synthesizes chemical formula (147)
Under stream of nitrogen gas, 5,6- dihydros-benzo [c] phenanthrene 1g (2.6mmol), diphenylamine 1.1g is put into reactor (6.5mmol), acid chloride (II) 0.03g (0.13mmol), BINAP 0.08g (0.13mmol), sodium tert-butoxide (sodium Tert-butoxide then) 1.0g (10.3mmol), toluene 100ml are stirred 12 hours while reflux cooling is carried out.Such as Fruit reaction terminates, then is filtered, and then removes solvent by decompression.Silica gel post separation is carried out to reactant, is obtained yellowish green (N, N- the diphenyl amino) -5,6- of color solid 3,8- bis- dihydros-benzo [c] phenanthrene (3,8-di (N, N-diphenylamino) -5, 6-dihydro-benzo [c]-phenanthrene) 0.8g (1.4mmol, 55.2%).
MS(EI)(m/z)：[M+]565
Synthesis example 19. synthesizes chemical formula (151)
It is synthesized using the method identical with synthesis example 18, obtains pistac solid 3, ((the 4'- first of N, N- bis- of 8- bis- Phenyl) amino) -5,6- dihydros-benzo [c] phenanthrene (3,8-di (N, N-di (4'-tolyl) amino) -5,6-dihydro-benzo [c] phenanthrene) 0.7g (1.1mmol, 42.7%).
MS(EI)(m/z)：[M+]621
Synthesis example 20. synthesizes chemical formula (153)
It is synthesized using the method identical with synthesis example 18, obtains white solid 3, ((the 4'- tertiary butyls of N, N- bis- of 8- bis- Phenyl) amino) -5,6- dihydros-benzo [c] phenanthrene (3,8-di (N, N-di (4'-tert-butylphenyl) amino) -5,6- Dihydro-benzo [c]-phenanthrene) 0.9g (1.2mmol, 45.3%).
MS(EI)(m/z)：[M+]790
Synthesis example 21. synthesizes chemical formula (161)
It is synthesized using the method identical with synthesis example 18, obtains the white solid 3, (N- phenyl-N-2'- naphthalenes of 8- bis- Amino) -5,6- dihydros-benzo [c] phenanthrene (3,8-di (N-phenyl-N-2'-naphthylamino) -5,6-dihydro- Benzo [c] phenanthrene) 0.9g (1.32mmol, 51.1%).
MS(EI)(m/z)：[M+]665
Synthesis example 22. synthesizes chemical formula (163)
It is synthesized using the method identical with synthesis example 18, acquisition pistac solid 3,8- bis- (N- phenyl-N- (9', 9'- dimethyl -2'- fluorenyls) amino) -5,6- dihydros-benzo [c] phenanthrene (3,8-di (N-phenyl-N- (9', 9'-dimethyl- 2'-fluorenyl) amino) -5,6-dihydro-benzo [c]-phenanthrene) 0.9g (1.1mmol, 43.7%).
MS(EI)(m/z)：[M+]797
Synthesis example 23. synthesizes chemical formula (164)
It is synthesized using the method identical with synthesis example 18, obtains pistac the solid 3, (N- phenyl-N- (3'- of 8- bis- Pyridyl group) amino) -5,6- dihydros-benzo [c] phenanthrene (3,8-di (N-phenyl-N- (3'-pyridyl) amino) -5,6- Dihydro-benzo [c]-phenanthrene) 0.4g (0.7mmol, 50.1%).
MS(EI)(m/z)：[M+]567
The manufacture of [embodiment] organic illuminating element according to the present invention
The compound obtained using in above-mentioned synthesis example 1 to 15 uses ADN as the light emitting host substance of luminescent layer (ADN：9,10- bis- (2- naphthalenes)-anthracenes (9,10-di (2-naphthyl)-anthracene)) as host compound is compared, make With BD142 (N6,N12Bis- (3,4- 3,5-dimethylphenyls)-N6,N12- twoBase- 6,12- diamines) compound as luminescent layer Dopant substance, and manufacture organic illuminating element according to conventional methods.
First, it is being formed in glass substrateIt is deposited successively in thick ITO layer (anode)Thick sky Cave implanted layer (hole injection layer substance：HI-406(N1,N1'-(xenyl -4,4'- diyl) bis- (N1(naphthalene -1- bases)-N4,N4- Diphenyl benzene -1,4- diamines)),Thick hole transmission layer (hole transmission layer substance：Bis- (N- (1- naphthalene-n- phenyl)) Benzidine (α-NPB)), in the compound of the present invention doped with BD142 (N6,N12Bis- (3,4- 3,5-dimethylphenyls)-N6,N12- twoBase- 6,12- diamines)The luminescent layer of thickness,Thick electron transfer layer (electron transfer layer substance：ET4(6, 6'- (3,4- bis-Base -1,1- dimethyl -1H- thiophenes cough up -2,5- diyls) two -2,2'-, two pyridines)) andThe LiF of thickness,Thick aluminium cathode manufactures organic illuminating element.
It measures the characteristics of luminescence of the organic illuminating element of above-mentioned manufacture and is shown in table 1 below.
Table 1
[table 1]
As shown in Table 1 above, it is known that embodiment 1 to 15 is compared with comparative example 1, although voltage is similar, current efficiency and Brightness maximum improves 1.5 times, and chromaticity coordinates is also relatively excellent.
In addition, the compound obtained using in above-mentioned synthesis example 18 to 23 is made as the luminescent dopants substance of luminescent layer By the use of the compound of BD142 as dopant substance is compared, ADN (AND are used：9,10- bis- (2- naphthalenes) anthracene) as luminescent layer In addition to this light emitting host, manufactures same as the previously described embodimentsly.
Table 2
[table 2]
As shown in Table 2 above, the driving voltage compared with comparative example of embodiment 18 to 23 is excellent.Show that current efficiency is similar Or relatively low characteristic, by confirming CIEy values it is found that this is as a result, such as caused by being moved to short wavelength regions in chromaticity coordinates Fruit considers conversion efficiency, then can show the maximum characteristic for improving 1.6 times.
According to result, that is, table 1 and 2 of the organic illuminating element of above-described embodiment, the novel benzophenanthrene chemical combination of the present invention is utilized Object can manufacture the organic illuminating element of the excellents such as driving voltage, luminous efficiency and chromaticity coordinates.
Industry utilizability
Organic illuminating element using the novel triphenylene compound of the present invention has driving voltage, luminous efficiency With the effect of the excellents such as excitation purity.

Claims (6)

1. a kind of compound is one kind in the compound represented by following chemical formula：
2. a kind of organic illuminating element, it includes compounds described in claim 1.
3. organic illuminating element according to claim 2, wherein, hole injection layer, sky between the anode and cathode Cave transport layer or luminescent layer include compound described in claim 1.
4. organic illuminating element according to claim 3, wherein, between the anode and cathode, further include choosing Free luminescent layer, hole injection layer, hole transmission layer, electronic barrier layer, electron transfer layer, electron injecting layer, hole blocking layer More than one layer in the group of composition.
5. organic illuminating element according to claim 4, wherein, between the anode and cathode selected from luminescent layer, More than one in hole injection layer, hole transmission layer, electronic barrier layer, electron transfer layer, electron injecting layer, hole blocking layer Layer utilize vacuum evaporation mode or solwution method formation.
6. organic illuminating element according to claim 2, wherein, the organic illuminating element is for display element, display Device element, illumination component.
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