CN103641830B - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDF

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CN103641830B
CN103641830B CN201310559945.2A CN201310559945A CN103641830B CN 103641830 B CN103641830 B CN 103641830B CN 201310559945 A CN201310559945 A CN 201310559945A CN 103641830 B CN103641830 B CN 103641830B
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organic electroluminescent
compound
organic
electroluminescent device
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CN103641830A (en
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金侈植
赵英俊
权赫柱
金奉玉
金圣珉
尹胜洙
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Rohm and Haas Electronic Materials Korea Ltd
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Abstract

Disclosed are a novel organic electroluminescent compound and an organic electroluminescent device comprising the same. When used as host material of organic electroluminescent material of an OLED device, the disclosed organic electroluminescent compound exhibits high luminous efficiency and excellent life property of the material as compared to conventional host material. Therefore, it can be used to manufacture OLEDs having very good operation life.

Description

New organic electroluminescent compounds and the organic electroluminescent using the compound Equipment
Present patent application is that international application no is PCT/KR2010/001647, and international filing date is March 17 in 2010 Day, it is entitled " new organic electroluminescent compounds and to make into the Application No. 201080022499.6 of National Phase in China With the organic electroluminescent device of the compound " application for a patent for invention divisional application.
Technical field
The present invention relates to the organic electroluminescent compounds of novelty and the organic electroluminescent device comprising the compound. It is more particularly related to be used as the novel organic electroluminescent compounds of electroluminescent material, and use them As matrix（host）Organic electroluminescent device.
Background technology
Determine OLED（Organic electroluminescent LED）Luminous efficiency most important factor be electroluminescent material class Type.Although up to the present fluorescent material has been widely used as electroluminescent material, from the point of view of electroluminescent mechanism, exploitation Phosphor material is that luminous efficiency is improved in theory one of up to 4 times best method.
Up to the present, iridium（III）Complex compound is a kind of well-known phosphor material, including（acac）Ir（btp）2、 Ir（ppy）3And Firpic, respectively as red, green and blue phosphor materials.Specifically, many phosphor materials are current Jing is studied in Japan, Europe and the U.S..
As the host material of phosphorescent light-emitting materials, be up to the present most widely known by the people be the carbazoles of 4,4'-N, N'- bis-- Biphenyl（biphenyl）（CBP）, and it is known using hole blocking layer（Such as BCP and BAlq）With efficient OLED. Pioneer Electronic Corp.（Japan）It has been reported that using two（2- methyl -8- quinolinol roots（quinolinato））（P-phenyl phenol root （phenolato））Aluminium（III）（BAlq）High performance OLED of the derivative as matrix.
Although from from the point of view of luminosity with advantage, they have low glass transition to material of the prior art Temperature and excessively poor heat endurance, so these materials are often during gas-phase deposition under high temperature and vacuum Change.In OLED, power efficiency=(π/voltage) × current efficiency is defined.Therefore, power efficiency is inversely proportional to voltage, And power efficiency should be higher obtaining relatively low OLED power consumptions.In practice, using electrophosphorescence material OLED shows its current efficiency（cd/A）It is more considerably higher than the OLED using fluorescence EL materials.But, using conventional material example Such as in the case of host materials of the BAlq and CBP as phosphor material, in power efficiency（lm/w）The no obvious advantage of aspect, This is because compare that there is higher operating voltage using the OLED of fluorescent material.And, the OLED can not obtain setting for satisfaction The standby life-span.
Accordingly, it would be desirable to develop stability and the further improved host material of performance.
The content of the invention
The description of inventive technique problem
The present inventor makes great efforts to overcome problem of the conventional art, so as to invent the electroluminescent compounds of novelty To realize the organic electroluminescent device with excellent luminous efficiency and the equipment life being obviously prolonged.
It is therefore an object of the present invention to overcome the problems referred to above and the organic electroluminescent compounds for including skeleton are provided, with Compare conventional substrate material and obtain higher luminous efficiency, the equipment life of raising and suitable chromaticity coordinates.
It is a further object to provide having high efficiency and long-life organic electroluminescent device, it is used should Organic electroluminescent compounds are used as electroluminescent material.
The method of solve problem
Specifically, the present invention relates to use chemical formula（1）-（5）One of represent organic electroluminescent compounds and bag Include the organic electroluminescent device of the compound.Conventional substrate material is compared due to the organic electroluminescent compounds of the present invention to carry For more preferable luminous efficiency and excellent life performance, therefore the OLED with excellent working life can be obtained.
[chemical formula 1]
[chemical formula 2]
[chemical formula 3]
[chemical formula 4]
[chemical formula 5]
Wherein,
X and Y is independently selected from N (Ar1), O and S, wherein Ar1Can be mutually different, and ought have two or more Ar1During group, Ar1It is represented by Ar1Or Ar2；
Z1To Z8Independently selected from C (Ar3) and N, wherein Ar3Can be mutually different, and adjacent Ar3Group can be connected together Form ring；
Ar1And Ar2Independently selected from (Cl-C60) alkyl, (C3-C60) cycloalkyl, comprising one or more selected from N, O, S, The heteroatomic 5- or 6- circle heterocycles alkyl of Si and P, (C7-C60) bicyclic alkyl, adamantyl, (C2-C60) thiazolinyl, (C2- C60) alkynyl, (C6-C60) aryl and (C3-C60) heteroaryl；
Ar3Independently selected from hydrogen, (Cl-C60) alkyl, halogen, cyano group, (C3-C60) cycloalkyl, comprising one or more Selected from the heteroatomic 5- or 6- circle heterocycles alkyl of N, O, S, Si and P, (C7-C60) bicyclic alkyl, adamantyl, (C2-C60) Thiazolinyl, (C2-C60) alkynyl, (C6-C60) aryl, (Cl-C60) alkoxyl, (C6-C60) aryloxy group, (C3-C60) heteroaryl, (C6-C60) arylthio, (Cl-C60) alkylthio group, single-or two (Cl-C30) alkylaminos, single-or two (C6-C30) fragrant aminos, three (Cl-C30) aIkylsilyl groups, two (Cl-C30) alkyl (C6-C30) arylsilyl groups, three (C6-C30) arylsilyls Base, single-or two (C6-C30) arylboranyls, single-or two (Cl-C60) boron alkyl alkyl, nitro and hydroxyl；And
Ar1To Ar3Alkyl, cycloalkyl, Heterocyclylalkyl, bicyclic alkyl, adamantyl, thiazolinyl, alkynyl, aryl, alcoxyl Base, aryloxy group, heteroaryl, arylthio, alkylthio group, alkylamino, fragrant amino, trialkylsilkl, di alkylaryl monosilane Base, diarye silyl, arylboranyl or boron alkyl alkyl can further by one or more substituents being selected from the group Replace：(Cl-C60) alkyl, halogen, cyano group, (C3-C60) cycloalkyl, comprising one or more selected from the miscellaneous of N, O, S, Si and P 5- the or 6- circle heterocycles alkyl of atom, (C7-C60) bicyclic alkyl, adamantyl, (C2-C60) thiazolinyl, (C2-C60) alkynyl, (C6-C60) aryl, (Cl-C60) alkoxyl, (C6-C60) aryloxy group, P (=O) RaRb[RaAnd RbIndependently represent (Cl-C60) Alkyl or (C6-C60) aryl] replace (C6-C60) aryl, (C3-C60) heteroaryl, (C6-C60) aryl replace (C3- C60) heteroaryl, (Cl-C60) alkyl-substituted (C3-C60) heteroaryl, (C6-C60) aryl (Cl-C60) alkyl, (C6-C60) Arylthio, (Cl-C60) alkylthio group, single-or two (Cl-C30) alkylaminos, single-or two (C6-C30) fragrant aminos, three (Cl-C30) AIkylsilyl groups, two (Cl-C30) alkyl (C6-C30) arylsilyl groups, three (C6-C30) arylsilyl groups, single-or Two (C6-C30) arylboranyls, single-or two (Cl-C60) boron alkyl alkyl, nitro and hydroxyl, not including such situation：X All it is N (Ar with Y1) and Z1To Z8All it is C (Ar3)。
Substituent including " (Cl-C60) alkyl " part as herein described can include 1-60 carbon atom, and 1-20 carbon is former Son or 1-10 carbon atom.6-60 carbon atom can be included including the substituent of " (C6-C60) aryl " part, 6-20 carbon is former Son or 6-12 carbon atom.3-60 carbon atom, 4-20 carbon can be included including the substituent of " (C3-C60) heteroaryl " part Atom or 4-12 carbon atom.3-60 carbon atom can be included including the substituent of " (C3-C60) cycloalkyl " part, 3-20 is individual Carbon atom or 3-7 carbon atom.2-60 carbon atom, 2- can be included including the substituent of " (C2-C60) alkenyl or alkynyl " part 20 carbon atoms or 2-10 carbon atom.
The term " alkyl " of the present invention includes straight or branched saturation univalence hydrocarbyl or its combination, and they can only by carbon atom With hydrogen atom composition.Term " alkoxyl " represents-O- alkyl, and wherein alkyl is as defined above.
Term " aryl " described herein represents and the organic group obtained after a hydrogen atom is removed by aromatic hydrocarbon.Aryl includes single Ring or carbocyclic fused ring system, each ring of aryl is suitably comprising 4-7, preferred 5-6 annular atom.May also comprise two or more aryl By the structure of chemical bonds.Specific example includes phenyl, naphthyl, xenyl（biphenyl）, anthryl, indenyl, fluorenyl, phenanthrene Base（phenanthryl）, benzo [9,10] phenanthryl（triphenylenyl）, pyrenyl,Base（perylenyl）、Base （chrysenyl）, aphthacene base（naphthacenyl）, fluoranthene base（fluoranthenyl）Deng, but not limited to this.
Term " heteroaryl " as herein described is represented in aromatic rings skeletal atom comprising the 1-4 hetero atom selected from N, O and S And remaining aromatic rings skeletal atom is the aryl of carbon atom.The heteroaryl can be 5- or 6- unit monocycles heteroaryl or with The polyheteroaromatic that individual or multiple phenyl ring are condensed, and can be fractional saturation.May also comprise with one or more by changing Learn the structure of bonded heteroaryl.The heteroaryl may include divalent aryl, and its hetero atom is aoxidized or quaternized formation N- oxygen Compound, quaternary ammonium salt etc..Specific example include bicyclic heteroaryl for example furyl, thienyl, pyrrole radicals, imidazole radicals, pyrazolyl, It is thiazolyl, thiadiazolyl group, isothiazolyl, differentOxazolyl,Oxazolyl,Di azoly, triazine radical, tetrazine base, triazolyl, tetrazolium Base, furazanyl（furazanyl）, pyridine radicals, pyrazinyl, pyrimidine radicals, pyridazinyl；Polyheteroaromatic such as benzofuranyl, benzene Bithiophene base, isobenzofuran-base, benzimidazolyl, benzothiazolyl, benzisothia oxazolyl, benzisoxaOxazolyl, benzo Oxazolyl, isoindolyl, indyl, indazolyl, diazosulfide base, quinolyl, isoquinolyl, cinnolines base（cinnolinyl）、 Quinazolyl, quinolizine base（quinolizinyl）, quinoxalinyl（quinoxalinyl）, carbazyl, phenanthridinyl （phenanthridinyl）, benzodioxole group（benzodioxolyl）；And its corresponding N- oxides（For example Pyridyl N-oxide, quinolyl N- oxides）；And its quaternary ammonium salt, but it is not limited to this.
The example of the organic electroluminescent compounds of the present invention can be the compound that one of following chemical formula is represented：
Wherein：Ar1And Ar2Such as chemical formula（1）-（5）Defined in.
In addition, the example of the organic electroluminescent compounds of the present invention can be the chemical combination that one of following chemical formula is represented Thing：
Wherein：Ar1And Ar2Such as chemical formula（1）-（5）Defined in.
The specific example of the organic electroluminescent compounds of the present invention can be the compound that one of following chemical formula is represented：
Wherein：Ar1And Ar2Such as chemical formula（1）-（5）Defined in.
More specifically, Ar1And Ar2Independently represent what one of phenyl, 1- naphthyls or 2- naphthyls or following chemical formula were represented Substituent, but their not limited to this.
Present invention provides a kind of organic electroluminescent device, it is by first electrode, second electrode and inserts described the At least one of which organic layer between one electrode and second electrode；Wherein described organic layer includes one or more chemical formula（1）- （5）One of represent organic electroluminescent compounds.
The organic electroluminescent device of the present invention is characterized in that organic layer includes electroluminescence layer, and the electroluminescence layer includes One or more chemical formula（1）-（5）One of the compound that represents as electroluminescent matrix and the doping of one or more phosphorescence Agent.The dopant does not have concrete restriction.
The organic electroluminescent device of the present invention may also include one or more selected from aromatic amine compound and styryl virtue The compound of amines, and one or more chemical formula（1）-（5）One of represent organic electroluminescent compounds.
In the organic electroluminescent device of the present invention, the organic layer may also include one or more selected from period of element The races of Biao 1, the 2nd race, period 4 and period 5 transition metal, the metal of lanthanide series metal and D- transition elements or its complexing Thing, and one or more chemical formula（1）-（5）One of represent organic electroluminescent compounds.The organic layer may include electricity Electroluminescent layer and charge generation layer.
In addition to above-mentioned organic electroluminescent compounds, the organic electroluminescent device may also comprise one or more layers The organic electro luminescent layer of blue light-emitting, green glow or ruddiness, to form the organic electroluminescent device for emitting white light.
The advantageous effects of invention
The organic electroluminescent compounds of the present invention are used as to be shown during the host material of the electroluminescent organic material of OLED Go out the material and there is excellent luminous efficiency and good life performance, so can be manufactured with very good berth by the compound The OLED in life-span.
Embodiments of the present invention
Also the present invention is further described by referring to preparation example and embodiment, to illustrate the representational Organic Electricity of the present invention The luminescent properties of electro luminescent compounds, its preparation method and electroluminescence device, but be to provide these embodiments and be only used for more Embodiments of the present invention are understood well, rather than for limiting the scope of the present invention by any way.
Preparation example
Preparation example 1：Prepare compound (A)
Prepare compound (A-1)
Bromo- 2- nitrobenzene (30g, 148.5mmol), 1- naphthalene boronic acids（1-naphtaleneboronic acid）(30.6g, 178.2mmol),Pd(PPh3)4(5.14g,4.45mmol),2M K2CO3The aqueous solution (297.01mmol), toluene (500mL) and The mixture of ethanol (200mL) is stirred 4 hours in counterflow condition.Mixture is cooled to after room temperature, distilled water is added thereto to. Gained mixture is extracted with ethyl acetate, and extract is dried with magnesium sulfate, and vacuum distillation.Compound is obtained by post purifying (A-1)(31g,124.3mmol,84.03%)。
Prepare compound (A-2)
Compound（A-1）It is little that the mixture of (31g, 124.3mmol) and triethyl phosphite (300mL) is refluxed 10 When.Mixture is cooled to after room temperature, organic solvent is fallen in vacuum distillation.It is added thereto to distilled water, and the mixture second Acetoacetic ester is extracted.Extract is dried with magnesium sulfate, and vacuum distillation.By post purifying obtain compound (A-2) (18g, 82.84mmol,66.81%)。
Prepare compound (A-3)
Compound (A-2) (18g, 82.84mmol), l, 5- diphenyl -3- chloropyridines (26.4g, 99.41mmol), Pd (OAc)2(1.85g,8.28mmol),P(t-bu)3(8.17ml, 16.5mmol, in dimethylbenzene 50%), NaOt-bu (23.8g, 248.5mmol) it is refluxed 12 hours with the mixture of toluene (500mL).The mixture is cooled to after room temperature, thereto Distilled water, and the mixture is added to be extracted with ethyl acetate.Extract is dried with magnesium sulfate, and vacuum distillation.It is pure by post Change obtain compound (A-3) (19g, 42.54mmol, 51.36%).
Prepare compound (A-4)
To compound（A-3）(19g, 42.54mmol) is dissolved in DMF（200mL）Solution in add NBS (8.33g, 46.80mmol).After room temperature is placed 10 hours, organic solvent is fallen in vacuum distillation.It is added thereto to distilled water, and the mixing Thing is extracted with ethyl acetate.Extract is dried with magnesium sulfate, and vacuum distillation.By post purifying obtain compound (A-4) (20g, 38.06mmol,89.47%)。
Prepare compound (A-5)
In -78 DEG C to being dissolved in THF（200mL）Compound（A-4）Be slowly added in solution n-buLi (15.22mL, 38.06mmol, 2.5M in hexane）.After stirring 1 hour, trimethylborate is added thereto to.The mixture is slowly warmed up to Room temperature, and stir 12 hours.Distilled water is added thereto to, and the mixture is extracted with ethyl acetate.Extract magnesium sulfate It is dried, and vacuum distillation.By post purifying obtain compound (A-5) (8g, 16.31mmol, 42.86%).
Prepare compound (A-6)
Compound (A-5) (8g, 16.31mmol), bromo- 2- nitrobenzene (3.95g, 19.57mmol), Pd (PPh3)4 (0.56g,0.48mmol),2M K2CO3The mixture of the aqueous solution (16mL, 32.62mmol), toluene (70mL) and ethanol (20mL) It is refluxed.According to synthesis compound（A-1）Identical step obtains compound（A-6）(7g,12.33mmol,75.62%).
Prepare compound (A-7)
Compound (A-6) (7g, 12.33mmol) and triethyl phosphite（100mL）Mixing, and according to synthesis compound （A-2）Identical step obtains compound（A-7）(4g,7.46mmol,58.33%).
Prepare compound (A)
Compound (A-7) (4g, 7.46mmol), iodobenzene (1.25mL, 11.20mmol), copper powder (0.71g, 11.20mmol),K2CO3(3.09g), the mixture backflow of 18- crown-s 6 (0.15g, 0.59mmol) and 1,2- dichloro-benzenes (100mL) Stirring 15 hours.Reactant mixture is cooled to after room temperature, organic solvent is fallen in vacuum distillation.It is added thereto to distilled water, and institute State mixture to be extracted with ethyl acetate.Extract by post purifying obtain compound (A) (3.6g, 5.88mmol, 78.88%).
Preparation example 2：Prepare compound (B)
Prepare compound (B-1)
The bromo- 2,3- dinitro benzenes (20g, 61.36mmol) of l, 4- bis-, 1- naphthalene boronic acids (26g, 153.42mmol), Pd (PPh3)4(3.54g,3.06mmol),2M K2CO3The aqueous solution (90mmol), the mixing of toluene (200mL) and ethanol (100mL) Thing is stirred 10 hours in counterflow condition.The reactant mixture is cooled to after room temperature, distilled water is added thereto to, and it is described mixed Compound is extracted with ethyl acetate.Extract is dried with magnesium sulfate, and vacuum distillation.Compound (B-1) is obtained by post purifying (22g,52.32mmol,85.28%)。
Prepare compound (B-2)
Compound (B-1) (22g, 52.32mmol) and triethyl phosphite (200mL) mix, and in 180 DEG C of stirrings.Root According to synthesis compound（A-2）Identical step obtains compound（B-2）(10g,28.05mmol,53.95%).
Prepare compound (B-3)
Compound (B-2) (10g, 28.05mmol), 2- iodine naphthalenes (7.1g, 28.05mmol), copper powder (2.67g, 42.08mmol),K2CO3(11.63g, 84.17mmol), 18- crown-s 6 (0.59g, 2.24mmol) and 1,2- dichloro-benzenes (100mL) Mixture be refluxed 20 hours in 190 DEG C.After being cooled to room temperature, organic solvent is fallen in vacuum distillation.It is added thereto to distillation Water, and the mixture is extracted with ethyl acetate.Extract is dried with magnesium sulfate, and vacuum distillation.By post purifyingization Compound (B-3) (4g, 8.28mmol, 29.60%).
Prepare compound (B)
DMF is dissolved in including（20mL）NaH (0.49g, 12.43mmol, 60% dispersion liquid in mineral oil) solution Add in reaction vessel and be dissolved in DMF（20mL）Compound（B-3）The solution of (4g, 8.28mmol).After 1 hour, by 2- chloro- 4, 6- diphenyl triazines (2.66g, 9.94mmol) is dissolved in DMF（20mL）Solution be added thereto.After stirring 12 hours, distillation is added Water, and obtained solid filtration under diminished pressure.From ethyl acetate and DMF be recrystallized to give compound (B) (3.5g, 4.90mmol, 59.21%)。
Preparation example 3：Prepare compound (C)
Prepare compound（C-1）
Ethanol is dissolved in 1,2- cyclohexyl diketones (42.52g, 379.26mmol)（1000mL）Solution in be slowly added to 2- Naphthyl hydrazine (20g, 126.42mmol).It is added thereto to acetic acid (0.28mL, 5.05mmol), and heats the mixture to 40 DEG C.2 After hour, the mixture is cooled down, and be added thereto to distilled water.Obtained solid filtration under diminished pressure obtains compound（C-1） (17g,67.37mmol,53.47%)。
Prepare compound (C-2)
To compound（C-1）(17g, 67.37mmol) is dissolved in the solution of acetic acid (100mL) and adds trifluoroacetic acid (10mL).After being stirred at room temperature 2 hours, distilled water is added thereto to.Mixture is neutralized with the NaOH aqueous solution, and uses ethyl acetate Extraction.Extract is dried with magnesium sulfate, and vacuum distillation.By post purifying obtain compound (C-2) (11g, 46.75mmol, 69.39%)。
Prepare compound (C-3)
According to synthesis compound（B-3）Identical step, obtains compound（C-3）(10g,32.11mmol, 68.69%)。
Prepare compound (C-4)
According to synthesis compound（C-1）Identical step, obtains compound（C-4）(12g,29.88mmol, 93.07%)。
Prepare compound (C-5)
According to synthesis compound（C-2）Identical step, obtains compound（C-5）(6g,15.68mmol,52.50%).
Prepare compound (C)
According to synthesis compound（B）Identical step, obtains compound（C）(5g,8.14mmol,51.95%).
Preparation example 4：Prepare compound (D)
Prepare compound (D-2)
According to synthetic example（A-1）Identical step, but use compound（D-1）Obtain compound（D-2）(11g, 38.02mmol,89.22%).
Prepare compound (D-3)
According to synthesis compound（A-2）Identical step obtains compound（D-3）(8g,31.09mmol,81.78%).
Prepare compound (D)
According to synthesis compound（B）Identical step obtains compound（D）(6g,12.30mmol,38.70%).
Preparation example 5：Prepare compound E and F
Prepare compound (E-2)
According to synthesis compound（A-1）Identical step, but use compound（E-1）Obtain compound（E-2）(15g, 51.85mmol,86.51%)。
Prepare compound (E-3)
According to synthesis compound（A-2）Identical step, obtains compound（E-3）(6g,23.31mmol,44.97%).
Prepare compound (E)
According to synthesis compound（B）Identical step, obtains compound（E）(5g,10.25mmol,43.99%).
Prepare compound (F-1）
According to synthesis compound（A-2）Identical step, obtains compound（F-1）(3g,11.65mmol,22.48%).
Prepare compound (F)
According to synthesis compound（B）Identical step, obtains compound（F）(3g,6.15mmol,52.81%).
Preparation example 6：Prepare compound (G) and（H）
Prepare compound (G-1)
Carbazole (20g, 119.6mmol), iodobenzene (20mL, 179.41mmol), copper (11.4g, 179.41mmol), K2CO3 The mixture of (49g, 358.8mmol), 18- crown-s 6 (2.5g, 9.56mmol) and 1,2- dichloro-benzenes (100mL) is in 190 DEG C of stirrings 12 hours.After being cooled to room temperature, reactant mixture vacuum distillation.It is added thereto to distilled water, and gained mixture acetic acid second Ester is extracted.Extract is dried with magnesium sulfate, and vacuum distillation.By post purifying obtain compound (G-1) (22g, 90.42mmol, 75.60%)。
Prepare compound (G-2)
According to synthesis compound（A-4）Identical step, obtains compound（G-2）(25g,77.59mmol, 85.81%)。
Prepare compound (G-3)
According to synthesis compound（A-5）Identical step, obtains compound（G-3）(11g,38.31mmol, 49.37%)。
Prepare compound (G-4)
According to synthesis compound（A-1）Identical step, obtains compound（G-4）(12g,32.84mmol, 85.72%)。
Prepare compound (G-5)
According to synthesis compound（A-2）Identical step, carries out reaction and obtains compound in 4 hours（G-5）(6g, 17.99mmol,54.80%)。
Prepare compound (G)
According to synthesis compound（B）Identical step, obtains compound（G）(7g,12.39mmol,68.91%).
Prepare compound (H-1)
According to synthesis compound（A-2）Identical step, carries out reaction and obtains compound in 4 hours（H-1）(2g, 5.99mmol,18.26%)。
Prepare compound (H)
According to synthesis compound（B）Identical step, obtains compound（H）(1.7g,3.01mmol,50.26%).
According to preparation example（1）-（6）The step of prepare organic electroluminescent compounds (TA, TB and TC).Have obtained in these The substituent of organic electro luminescent compounds（Ar1And Ar2）And these compounds1H NMR and MS/FAB data are listed in table 1 below In 2.
Table 1
Table 2
[embodiment 1-10] manufactures OLED using the organic electroluminescent compounds of the present invention
Using the electroluminescent compounds manufacture OLED device of the present invention.
First, the transparency electrode ito thin film (15 Ω/) of OLED will be used for by made by glass（It is public purchased from SCP Department）Carry out ultrasonic wave with trichloro ethylene, acetone, ethanol and distilled water successively to clean, and be stored in before the use in isopropanol.
Then, ITO substrates are mounted in the substrate folder of vacuum phase deposition equipment（folder）In, will be by following chemical constitution The 4,4' that formula is represented, 4 "-three (N, N- (2- naphthyls)-phenyl amino) triphenylamines (2-TNATA) are placed in vacuum phase deposition equipment Cell (cell) in, be then vented to house vacuum degree and be up to 10-6Support.Electric current is applied to cell, 2-TNATA is steamed Send out, so as to the hole injection layer of the nano thickness of vapour deposition 60 on ITO substrates.
Then, N, N'- bis- (Alpha-Naphthyl)-N, N'- hexichol are added in another cell of the vacuum phase deposition equipment Base -4,4'- diamines (NPB) applies electric current to cell to evaporate NPB, so as to the nanometer thickness of vapour deposition 20 on hole injection layer The hole transport layer of degree.
The compound of the present invention is added in a cell of vapor deposition apparatus（It is 10-6Through vacuum under support Sublimation purification）（For example, compound TA8-H4-H2）, and by electroluminescent dopant（For example, compound（piq）2Ir（acac）） In adding another cell.Bi-material is doped with different speed evaporations with the concentration of 4-10 mole of %, so as in sky The electroluminescence layer of the nano thickness of vapour deposition 30 in the transport layer of cave.
Then, (Alq) vapour deposition is 20 nano thickness to three (8-hydroxyquinoline) aluminium (III) for following structural formula being represented Electron transport layer, by 8-hydroxyquinoline lithium (lithium quinolate) (Liq) vapour deposition for 1-2 nanometer thickness electronics Implanted layer.Then, using another vacuum phase deposition equipment, the Al negative electrodes of the nanometer thickness of vapour deposition 150 manufacture OLED.
[embodiment 11-20] manufactures OLED using the electroluminescent compounds of the present invention
According to the step manufacture OLED identical with the OLED of embodiment 1-10, but using the compound of the present invention（For example change Compound TA4-H4-H4）Organic iridium complex (the Ir (ppy) represented as host material and following chemical formula3) as electroluminescent Light-emitting dopant.
[comparative example 1 and 2] is using conventional electroluminescent material manufacture OLED
According to the step manufacture OLED identical with the embodiment of the present invention 1 and 11, but vacuum phase deposition equipment is another Two are added in individual cell（2- methyl 8- quinolinol roots) (p-phenyl phenol root) aluminium (III) (BAlq), rather than the electricity of the present invention Electro luminescent compounds, as host material.
In 1000cd/cm2Measurement embodiment 1-10 and embodiment 11-20（They include the organic electroluminescent of the present invention Compound）And comparative example 1 and 2（They include conventional electroluminescent compound）The operating voltage of the OLED of manufacture and power are imitated Rate, in being as a result listed in table 3 and 4.
From table 3 and 4, the organic electroluminescent compounds of present invention exploitation compare conventional material in terms of equipment performance With excellent performance.
Table 3
Table 4
As shown in Table 3, compared with conventional material, the compound of present invention exploitation shows excellent property in terms of luminosity Energy.Compared with the equipment of the comparative example 1 manufactured with conventional material, the equipment of present invention manufacture shows excellent current capability, from And operating voltage is reduced into 1V or more.Compared with the equipment of comparative example 1, they also show that current efficiency performance is at least the former 1.4 times, this is because luminescent properties are improved significantly.
As shown in Table 4, when the compound of present invention exploitation is used as the matrix of green electroluminescent, with setting for comparative example 2 Standby to compare, the equipment shows the much higher work(of at least the former 1.6 times because they have excellent luminescent properties Rate efficiency.Compared with conventional material, excellent luminescent properties are confirmed.Particularly, compared with the equipment of comparative example 1, implement The equipment of example 14 can be in the operating at voltages for reducing 2.7V, and the equipment of embodiment 17 shows that operating voltage is 5.5V, in 1000cd/ m2Power efficiency be 15.9lm/.
Therefore, the equipment for ruddiness or green glow being sent as host material using electroluminescent compounds of the present invention shows excellent Luminescent properties, while reducing operating voltage, so causing the power efficiency of the particularly equipment of green light increases 5.1-7.7lm/ W, is as a result to improve power consumption.

Claims (7)

1. a kind of organic electroluminescent compounds, it is characterised in that the compound is selected from following compounds：
Wherein：Ar1Selected from triazine radical, pyridine radicals, pyrazinyl, benzofuranyl, benzothienyl, isobenzofuran-base, benzo miaow Oxazolyl, benzothiazolyl, benzoOxazolyl, isoindolyl, indyl, indazolyl, quinolyl, isoquinolyl, quinazolyl, quinoline Quinoline base and carbazyl, wherein Ar1Can be replaced by (C6-C60) aryl or (C3-C60) heteroaryl.
2. a kind of organic electroluminescent device, the equipment includes the organic electroluminescent compounds described in claim 1.
3. organic electroluminescent device as claimed in claim 2, it is characterised in that the equipment includes first electrode；Second Electrode；And one or more layers organic layer between the insertion first electrode and second electrode, the organic layer includes a kind of Or the organic electroluminescent compounds described in various claims 1 and one or more phosphorescent dopants.
4. organic electroluminescent device as claimed in claim 3, it is characterised in that the organic layer also includes one or more Selected from aromatic amine compound and the amines of styryl aromatic amine compound.
5. organic electroluminescent device as claimed in claim 3, it is characterised in that the organic layer also includes one or more Selected from the gold of the race of the periodic table of elements the 1st, the 2nd race, period 4 and period 5 transition metal, lanthanide series metal and d- transition elements Category or the complex compound formed by them.
6. organic electroluminescent device as claimed in claim 3, it is characterised in that the organic layer include electroluminescence layer and Charge generation layer.
7. organic electroluminescent device as claimed in claim 3, it is characterised in that the equipment is the organic electroluminescence for emitting white light Equipment, the organic layer includes the organic electro luminescent layer of one or more layers blue light-emitting, ruddiness or green glow simultaneously.
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