CN103201273A - Novel compounds for organic electronic material and organic electroluminescent device using the same - Google Patents

Novel compounds for organic electronic material and organic electroluminescent device using the same Download PDF

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CN103201273A
CN103201273A CN2011800499936A CN201180049993A CN103201273A CN 103201273 A CN103201273 A CN 103201273A CN 2011800499936 A CN2011800499936 A CN 2011800499936A CN 201180049993 A CN201180049993 A CN 201180049993A CN 103201273 A CN103201273 A CN 103201273A
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alkyl
aryl
compound
organic
heteroaryl
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黄守振
安熙春
李美爱
尹石根
金奉玉
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Rohm and Haas Electronic Materials Korea Ltd
Rohm and Haas Electronic Materials LLC
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Abstract

Provided are novel compounds for organic electronic material and an organic electroluminescent device using the same. Because the compounds for organic electronic material according to the present invention are highly efficient at transporting electrons, crystallization is prevented when manufacturing a device and current properties of the device are improved due to favorably formed layers. Accordingly, OLED devices having improved power efficiency as well as reduced operating voltage can be manufactured. Chemical formula 1.

Description

Be used for the new compound of organic electronic material and the organic electroluminescence device that uses this compound
Invention field
The present invention relates to for the new compound of organic electronic material and the organic electroluminescence device that uses this compound.
Technical background
In display device, electroluminescent (EL) device is preferred, because they provide contrast gradient and the quick speed of response of wide visual angle, excellence as the self-emission display device.Eastman Kodak Co (Eastman Kodak) has at first developed a kind of organic EL device in 1987, this device uses low molecular weight aromatic diamines and aluminum complex as the material [Appl.Phys.Lett.51,913,1987] that forms electroluminescence layer.
In organic EL device, when electric charge was applied to the organic layer that is formed between electron injection electrode (negative electrode) and the hole injecting electrode (anode), electronics and hole pairing also produced exciton.It is luminous to utilize electroluminescent (phosphorescence or fluorescence) by the state at the exciton inactivation.Organic EL device is with the voltage of about 10V and about 100～10,000cd/m 2High brightness come polarized light-emitting.The feature of organic EL device is by fluorescent material is simply selected, and is luminous in blueness arrives red spectral range.The advantage of organic EL device is, it can form at flexible transparent base material (for example plastics), can compare operation under the low voltage (10V or lower) of plasma display panel or inorganic EL indicating meter, consume power still less and excellent color is provided.
In organic EL device, determine that the most important factor of its performance (comprising luminous efficiency and working life) is electroluminescent material.Ask for something to electroluminescent material comprises the anti-decomposability in high solid-state electroluminescent quantum yield, high electronics and hole migration, the vacuum deposition process, ability and the stability of formation uniform thin film.
Electroluminescent organic material generally is divided into macromolecular material and low molecular material.Consider that from the molecular structure aspect low molecular material comprises metal complexes and metal-free complete electroluminescent organic material.This electroluminescent material comprises the title complex of chelating, as three (oxine) aluminum complex, and coumarin derivatives, the tetraphenylbutadiene derivative, two (styryl arylidene) derivative Yi are Ji the oxadiazole derivative.According to these materials, it is reported to obtain visible-range luminous from the blueness to the redness.
Adopted three kinds of electroluminescent materials (red, green and blue) to realize all colour organic luminous diode (OLED) indicating meter.Important problem is that development has high-level efficiency and long-life redness, green and blue electroluminescent material, thereby promotes the mass permanence of organic electroluminescent (EL) device.Consider that from function aspects the EL material is divided into substrate material and dopant material.Usually known, the device architecture with the most excellent EL performance can be made by the EL layer of the preparation of doping doping agent in matrix.At present, exploitation has high-level efficiency and long-life organic EL device becomes urgent target, waits until the required EL performance of large size OLED display pannel in considering, urgent especially is that the material that conventional EL material has a lot of EL performances is compared in exploitation.
From this viewpoint, the exploitation substrate material is in the sixty-four dollar question that needs to solve.The required character of substrate material (as solid-state solvent and energy transmission person) is high purity and suitable molecular weight, can carry out vacuum vapor deposition.In addition, second-order transition temperature and heat decomposition temperature should be enough high, to guarantee thermostability.In addition, described substrate material should have high electrochemical stability, so that the long life-span to be provided.Be easy to form amorphous thin film, it has high viscosity for other adjacent materials, but does not have the interlayer migration.
When using doping techniques to make organic EL device, can not realize that energy transfers to the doping agent of excited state with 100% ratio from substrate molecule, substrate material and doping agent all can be luminous.Especially, under the situation of emitting red light device, because substrate material sends the light of the visibility wavelength region higher than doping agent, so purity of color is because substrate material dim luminous and variation.If practice this technology, then require to increase luminescent lifetime and improve weather resistance.
At present, known CBP is the substrate material that is widely used as phosphor material most.Reported the efficient OLED that uses the hole blocking layer that comprises BCP, BAlq etc.Pioneer Electronic Corp. (Japan) etc. has reported and has used the BAlq derivative as the high-performance OLED of matrix.
Figure DEST_PATH_GDA00003186253600021
Although these materials provide good electroluminescence characters, they have some defectives, and as degrading when the vacuum high-temperature deposition process, this is because they have the thermostability of low second-order transition temperature and difference.Because the power efficiency of OLED is determined by (π/voltage) * current efficiency, so power efficiency and voltage are inversely proportional to.Need high power efficiency to reduce the watt consumption of OLED.In fact, use the OLED of phosphor material to provide than the much better current efficiency (cd/A) of OLED of using fluorescent material.But, when current material when for example BAlq, CBP etc. are as the matrix of phosphor material, to compare and use the OLED of fluorescent material not having clear superiority aspect the power efficiency (lm/W), this is because driving voltage is higher.In addition, the OLED device does not have gratifying working life.Therefore, need more stable, the more high performance substrate material of exploitation.
Summary of the invention
Technical problem
Therefore, the purpose of this invention is to provide for the relative current material with the device working life of luminous efficiency and be improved and have the compound of organic electronic material of the excellent skeleton (backbone) of suitable chromaticity coordinates, to address the above problem.Another object of the present invention provides the high efficiency organic electroluminescence device with long service live, and it uses and is used for the compound of dynamo-electric electronic material being arranged as electroluminescent material.
Technical scheme
A kind of compound of the organic electronic material of representing for following Chemical formula 1 and the organic electroluminescence device that uses this compound are provided.Because the compound for organic electronic material of the present invention has superior luminous efficiency and good life properties, it can be used for making the OLED device, and this device has very superior working life and because the low power consumption that improved power efficiency causes.
Chemical formula 1
Figure DEST_PATH_GDA00003186253600031
Wherein:
L 1And L 2Represent singly-bound, (C3-C30) ring alkylidene group, (C6-C30) arylidene or (C3-C30) heteroarylidene independently;
X 1And X 2Represent CR independently 6Or N, except X 1And X 2All be CR 6Situation;
R 1To R 6Represent hydrogen independently, deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano group, (C3-C30) cycloalkyl, 5-unit to 7-unit Heterocyclylalkyl, (C2-C30) thiazolinyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxyl group, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C6-C30) arylthio, list or two (C1-C30) alkylamino, list or two (C6-C30) arylamino, three (C1-C30) alkyl silyl, two (C1-C30) alkyl (C6-C30) aryl silyl, three (C6-C30) aryl silyl, nitro or hydroxyl; And
L 1And L 2Ring alkylidene group, arylidene and heteroarylidene, and R 1To R 6Alkyl, cycloalkyl, Heterocyclylalkyl, thiazolinyl, alkynyl, aryl, heteroaryl also can further be replaced by one or more substituting groups independently, and described substituting group is selected from: deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano group, (C3-C30) cycloalkyl, 5-unit to 7-unit Heterocyclylalkyl, (C2-C30) thiazolinyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxyl group, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C6-C30) arylthio, list or two (C1-C30) alkylamino, list or two (C6-C30) arylamino, three (C1-C30) alkyl silyl, two (C1-C30) alkyl (C6-C30) aryl silyl, three (C6-C30) aryl silyl, nitro and hydroxyl;
Described heteroarylidene, Heterocyclylalkyl and heteroaryl comprise one or more B of being selected from, N, O, S, P (=O), the heteroatoms of Si and P;
Except *-L 1-R 1It is the situation of hydrogen.
In the present invention, " alkyl ", " alkoxyl group " and other substituting groups that comprises " alkyl " part comprise straight chain and side chain type.In the present invention, " cycloalkyl " comprises the polynuclear hydrocarbon ring, for example is with or without substituent adamantyl or is with or without substituent (C7-C30) bicyclic alkyl and monocyclic hydrocarbon ring.In the present invention, " aryl " represent by remove the organic group that a hydrogen atom obtains from aromatic hydrocarbon, can comprise 4-unit to 7-unit, specifically be monocycle or the condensed ring of 5-unit or 6-unit, comprise by singly linked a plurality of aryl.Their object lesson comprises, but be not limited to, phenyl, naphthyl, xenyl (biphenyl), anthryl, indenyl, fluorenyl, phenanthryl (phenanthryl), benzo [9,10] phenanthryl (triphenylenyl), pyrenyl, perylene base (perylenyl), Qu Ji (chrysenyl), naphthacenyl (naphthacenyl), fluoranthene base (fluoranthenyl) etc.Described naphthyl comprises 1-naphthyl and 2-naphthyl, and described anthryl comprises 1-anthryl, 2-anthryl and 9-anthryl, and described fluorenyl comprises 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.In the present invention, " heteroaryl " refer to contain 1-4 be selected from B, N, O, S, P (=O), the heteroatoms of Si and P is the aromatic yl group of carbon atom as aromatic ring backbone atoms and remaining aromatic ring backbone atoms, for example with the 5-unit of one or more phenyl ring condensations or 6-unit's bicyclic heteroaryl and polyheteroaromatic, it can be fractional saturation.In addition, described heteroaryl comprises by singly linked and surpasses a heteroaryl.Heteroaryl comprises the divalent aryl group, and wherein the heteroatoms in the ring can be oxidized or quaternized, to form for example N-oxide compound or quaternary ammonium salt.Their object lesson comprises bicyclic heteroaryl for example furyl, thienyl, pyrryl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl group, isothiazolyl, isoxazolyl, oxazolyl, oxadiazole base, triazinyl, tetrazine base, triazolyl, tetrazyl, furazan base (furazanyl), pyridyl, pyrazinyl, pyrimidyl, pyridazinyl etc.; Polyheteroaromatic is benzofuryl (benzofuranyl) for example, benzothienyl, isobenzofuran-base, benzimidazolyl-, benzothiazolyl, the benzisothiazole base, benzoisoxazole base benzoxazolyl, pseudoindoyl, indyl, indazolyl, the diazosulfide base, quinolyl, isoquinolyl, cinnolines base (cinnolinyl), quinazolyl, quinoxalinyl (quinoxalinyl), carbazyl, phenanthridinyl (phenanthridinyl), benzo dioxolyl (benzodioxolyl) etc.; And N-oxide compound (for example pyridyl N-oxide compound, quinolyl N-oxide compound etc.); And quaternary ammonium salt etc., but be not limited to this.
Among the present invention, " (C1-C30) alkyl " comprises (C1-C20) alkyl, more specifically is (C1-C10) alkyl, and " (C6-C30) aryl " comprise (C6-C20) aryl, more specifically is (C6-C12) aryl.Similarly, " (C3-C30) heteroaryl " comprises (C3-C20) heteroaryl, more specifically is (C3-C12) heteroaryl, and " (C3-C30) cycloalkyl " comprise (C3-C20) cycloalkyl, more specifically is (C3-C7) cycloalkyl.Similarly, " (C2-C30) alkenyl or alkynyl " comprises (C2-C20) alkenyl or alkynyl, more specifically is (C2-C10) alkenyl or alkynyl.
In addition, the compound for organic electronic material of the present invention can be represented with following Chemical formula 2 or 3.
Chemical formula 2
Figure DEST_PATH_GDA00003186253600051
Chemical formula 3
Figure DEST_PATH_GDA00003186253600061
Wherein,
L 1And L 2Represent singly-bound, (C3-C30) ring alkylidene group, (C6-C30) arylidene or (C3-C30) heteroarylidene independently; R 1Be (C6-C30) aryl or (C3-C30) heteroaryl; R 2To R 6Definition as the definition in the Chemical formula 1; L 1And L 2Ring alkylidene group, arylidene and heteroarylidene, and R 1Aryl and heteroaryl also can further be replaced by one or more substituting groups independently, described substituting group is selected from: deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano group, (C3-C30) cycloalkyl, 5-unit to 7-unit Heterocyclylalkyl, (C2-C30) thiazolinyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxyl group, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C6-C30) arylthio, list or two (C1-C30) alkylamino, list or two (C6-C30) arylamino, three (C1-C30) alkyl silyl, two (C1-C30) alkyl (C6-C30) aryl silyl, three (C6-C30) aryl silyl, nitro and hydroxyl.
R 1Heteroaryl can be selected from following structure:
Figure DEST_PATH_GDA00003186253600062
Wherein,
Y is NR 13, O or S; Z is NR 13, CR 14R 15, O or S; R 11To R 15Be hydrogen independently, deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano group, (C3-C30) cycloalkyl, 5-unit to 7-unit Heterocyclylalkyl, (C2-C30) thiazolinyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxyl group, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C6-C30) arylthio, list or two (C1-C30) alkylamino, list or two (C6-C30) arylamino, three (C1-C30) alkyl silyl, two (C1-C30) alkyl (C6-C30) aryl silyl, three (C6-C30) aryl silyl, nitro or hydroxyl; A is monocyclic aromatic rings or many cyclophanes ring or monocycle hetero-aromatic ring or encircles hetero-aromatic ring more.
Particularly, R 1 Be selected from following structure:
Figure DEST_PATH_GDA00003186253600071
R 2, R 3, R 4, R 5And R 6Be hydrogen independently;
L 1Be singly-bound or be selected from following structure:
Figure DEST_PATH_GDA00003186253600072
And
L 2Be singly-bound, phenylene or cyclohexylene.
More particularly, the compound for organic electronic material of the present invention can be enumerated as following compound, but following compound, but they do not limit the present invention:
Figure DEST_PATH_GDA00003186253600081
Figure DEST_PATH_GDA00003186253600101
Compound for organic electronic material of the present invention prepares by following proposal 1, but is not limited thereto, and can use adjacent known organic synthesis to prepare.
Scheme 1
Wherein,
The L of Chemical formula 1 1, L 2, X 1, X 2And R 1To R 5Define as Chemical formula 1, and X is halogen.
A kind of organic electroluminescence device is provided, and it comprises first electrode; Second electrode; And one or more layers organic layer between described first electrode of insertion and second electrode, wherein said organic layer comprises one or more compounds for organic electronic material that Chemical formula 1 is represented.Organic layer comprises electroluminescence layer, and the compound that wherein is used for the organic electronic material of Chemical formula 1 is used as substrate material.
When the compound that is used for organic electronic material of Chemical formula 1 when electroluminescence layer is used as matrix, comprised one or more phosphorescent dopants.The phosphorescent dopants that is used for organic electroluminescence device of the present invention is not particularly limited, but can be selected from the compound of chemical formula 4 expressions:
Chemical formula 4
M 1L 101L 102L 103
Wherein,
M 1Be the metal that is selected from the periodic table of elements the 7th family, the 8th family, the 9th family, the 10th family, the 11st family, the 13rd family, the 14th family, the 15th family and the 16th family, ligand L 101, L 102, and L 103Be independently selected from following structure:
Figure DEST_PATH_GDA00003186253600111
Wherein, R 201To R 203Represent that independently hydrogen, deuterium, halogen replacement or unsubstituted (C1-C30) alkyl, (C1-C30) alkyl replace or unsubstituted (C6-C30) aryl or halogen;
R 204To R 219Represent hydrogen independently, deuterium, replace or unsubstituted (C1-C30) alkyl, replace or unsubstituted (C1-C30) alkoxyl group, replace or unsubstituted (C3-C30) cycloalkyl, replace or unsubstituted (C2-C30) thiazolinyl, replace or unsubstituted (C6-C30) aryl, replace or unsubstituted list-(C1-C30) alkylamino or replacement or unsubstituted two-(C1-C30) alkylaminos, replace or unsubstituted list-(C6-C30) arylamino or replacement or unsubstituted two-(C6-C30) arylaminos, SF5, replace or unsubstituted three (C1-C30) alkyl silyl, replace or unsubstituted two (C1-C30) alkyl (C6-C30) aryl silyl, replace or unsubstituted three (C6-C30) aryl silyl, cyano group or halogen;
R 220To R 223Represent independently that hydrogen, deuterium, halogen replace or unsubstituted (C1-C30) alkyl or (C1-C30) alkyl replace or unsubstituted (C6-C30) aryl;
R 224And R 225Represent hydrogen, deuterium, replacement or unsubstituted (C1-C30) alkyl, replacement or unsubstituted (C6-C30) aryl or halogen, perhaps R independently 224And R 225Be connected to form alicyclic ring or monocycle or many cyclophanes ring by (C3-C12) alkylidene group that is with or without condensed ring or (C3-C12) alkenylene that is with or without condensed ring;
R 226Expression replaces or unsubstituted (C1-C30) alkyl, replacement or unsubstituted (C6-C30) aryl, replacement or unsubstituted (C5-C30) heteroaryl or halogen;
R 227To R 229Represent hydrogen, deuterium, replacement or unsubstituted (C1-C30) alkyl, replacement or unsubstituted (C6-C30) aryl or halogen independently; And
Q is
Figure DEST_PATH_GDA00003186253600121
Perhaps
Figure DEST_PATH_GDA00003186253600122
R wherein 231To R 242Represent hydrogen, deuterium independently, be with or without (C1-C30) alkyl, (C1-C30) alkoxyl group, halogen, replacement or unsubstituted (C6-C30) aryl, cyano group or replacement or unsubstituted (C5-C30) cycloalkyl of halogenic substituent, perhaps each in them can be connected to adjacent substituting group by alkylidene group or alkenylene and form volution or condensed ring, perhaps can be connected to R by alkylidene group or alkenylene 207Or R 208Form saturated or unsaturated condensed ring.
The phosphorescent dopants compound of chemical formula 4 is by the exemplary expression of following compound, but is not limited thereto.
Figure DEST_PATH_GDA00003186253600131
Figure DEST_PATH_GDA00003186253600141
In organic electronic devices of the present invention, except being used for the compound of organic electronic material that Chemical formula 1 is represented, described organic layer can comprise simultaneously that also one or more are selected from the compound of aromatic amine compound and styryl aromatic amine compound.The example of described aromatic amine compound or styryl aromatic amine compound is referring to korean patent application 10-2008-0123276,10-2008-0107606 or 10-2008-0118428 number, but is not limited thereto.
In addition, in organic electroluminescence device of the present invention, except being used for the compound of organic electronic material that Chemical formula 1 is represented, described organic layer can comprise that also one or more are selected from metal or the complex compound of the organo-metallic of the periodic table of elements the 1st family, the 2nd family, period 4 and period 5 transition metal, lanthanide series metal and d-transition element.Described organic layer can comprise electroluminescence layer and charge generation layer.
In addition, except being used for the compound of organic electronic material that described Chemical formula 1 is represented, described organic layer also can comprise the organic electro luminescent layer of one or more emission blue light, green glow or ruddiness simultaneously, to realize the organic electroluminescence device of emission white light.The example of the compound of blue light-emitting, green glow or ruddiness can be korean patent application 10-2008-0123276,10-2008-0107606 or 10-2008-0118428 number described compound, but is not limited thereto.
In organic electroluminescence device of the present invention, the layer (hereinafter referred to as " upper layer ") that is selected from chalcogenide layer, metal halide and metal oxide layer can be arranged on the internal surface of one or two electrode in the electrode pair.More particularly, the metal chalcogenide of silicon or aluminium (comprising oxide compound) layer can place on the anode surface of electroluminescent medium layer, and metal halide or metal oxide layer can place on the cathode surface of described electroluminescent medium layer.Thereby obtain job stability.For example, chalkogenide can be SiO x(1≤x≤2), AlO x(1≤x≤1.5), SiON, SiAlON etc.For example, metal halide can be LiF, MgF 2, CaF 2, rare earth metal fluorochemical etc.For example, metal oxide can be Cs 2O, Li 2O, MgO, SrO, BaO, CaO etc.
In organic electroluminescence device of the present invention, the mixing zone of electric transmission compound and reductibility doping agent also preferably is set, perhaps the mixing zone of hole transport compound and oxidisability doping agent at least one surface of prepared electrode pair.In this case, because the electric transmission compound is reduced into negatively charged ion, thereby promotes electronics from the mixing zone injection and be transferred to electroluminescent medium.In addition, because the oxidized formation positively charged ion of hole transport compound, thereby promote the hole from the mixing zone injection and be transferred to electroluminescent medium.Preferred oxidisability doping agent comprises various Lewis acids and acceptor compound.Preferred reductibility doping agent comprises basic metal, alkali metal compound, alkaline-earth metal, rare earth metal and composition thereof.In addition, the electroluminescent device that emits white light with two-layer or more multi-layered electroluminescence layer can use the reductibility dopant layer to prepare as charge generation layer.
Useful effect of the present invention
Have good illumination efficiency and excellent life properties because be used for the compound of organic electronic material of the present invention, it can be used for making the OLED device with very excellent working life.
Embodiments of the present invention
The present invention has further described and has been used for the compound of organic electronic material of the present invention, the luminosity for preparing the method for this compound and use the device of this compound.But, below these embodiment only be for illustrative purposes, rather than in order to limit the scope of the invention.
[preparation example 1] preparation compound 4
Figure DEST_PATH_GDA00003186253600161
The preparation of compound 1-1
The 1-bromo-2-oil of mirbane that mixes 10g (49.5mmol), the 1-naphthalene boronic acids of 10.2g (59.3mmol), the toluene of 200mL, the ethanol of 50mL and the water of 50mL add the Pd (PPh of 2.9g (2.5mmol) then 3) 4And the salt of wormwood of 20.5g (148.3mmol).This mixture stirred 5 hours at 120 ℃, was cooled to room temperature then, stopped this reaction with the 40mL aqueous ammonium chloride solution afterwards.Mixture with 500mL EA extraction obtains cleans with 100mL distilled water then.The anhydrous MgSO of the organic layer that obtains 4Drying, reduced pressure treatment is used silica dioxide gel column chromatography purifying then, thereby is obtained compound 1-1 (10g, 81%) to remove organic solvent.
The preparation of compound 1-2
The compound 1-1 of 10g (40.1mmol) is dissolved in 1 of 100mL, in the 2-dichlorobenzene, then to the triethoxy phosphine that wherein adds 100mL.This reaction mixture stirred 20 hours at 150 ℃, was cooled to room temperature then, used vacuum distilling to remove solvent, and namely 1,2-dichlorobenzene and triethoxy phosphine.With the remaining organic materials of 300mL EA extraction, clean with 40mL distilled water then.The anhydrous MgSO of the organic layer that obtains 4Drying, reduced pressure treatment is used silica dioxide gel column chromatography purifying then, thereby is obtained compound 1-2 (7g, 80%) to remove organic solvent.
The preparation of compound 1-3
The compound 1-2 of 20g (92mmol) and the 1-bromo-4-iodobenzene of 43.5g (184mmol) are dissolved in 500mL toluene, the diaminoethanes of CuI, the 6.2mL (92mmol) of adding 8.8g (46mmol) and the K of 58.7g (276mmol) 3PO 4, refluxed then 30 hours.This reaction mixture is cooled to room temperature, uses the aqueous hydrochloric acid termination reaction of 50mL2.0M afterwards, with 1L EA extraction gained mixture, cleans with 200mL distilled water then.The anhydrous MgSO of the organic layer that obtains 4Drying, reduced pressure treatment is used silica dioxide gel column chromatography purifying then, thereby is obtained compound 1-3 (19g, 56%) to remove organic solvent.
The preparation of compound 1-4
The compound 1-3 of 19g (51mmol) is dissolved among the 250mL THF, is cooled to-78 ℃ then, afterwards under-78 ℃ to wherein adding 24.5mL n-BuLi(2.5M, in the hexane).This mixture stirred 1 hour at-78 ℃, added 8.5mL B (OMe) 3, stirred 2 hours, use 100mL aqueous ammonium chloride solution termination reaction then.Subsequently, the mixture with 500mL EA extraction obtains cleans with 100mL distilled water then.The anhydrous MgSO of the organic layer that obtains 4Drying, reduced pressure treatment to be removing organic solvent, recrystallization, thus obtain compound 1-4 (14g, 81%).
The preparation of compound 2-1
The fluoranthene of 50g (247mmol) is dissolved in the 1L oil of mirbane, then to the bromine that wherein dropwise adds lentamente with the 12mL (234.7mmol) of 200mL oil of mirbane dilution.Finish after solution dropwise adds, reaction soln at room temperature stirred 20 hours.The saturated chlorinated thio aqueous sodium persulfate solution that adds 500mL in the reaction soln, thereby termination reaction.EA with 3L extracts the mixture that obtains, and cleans with 1L distilled water then.The anhydrous MgSO of the organic layer that obtains 4Drying, reduced pressure treatment use silica dioxide gel to filter to remove organic solvent, recrystallization then, thus obtain compound 2-1 (65g, 94%).
The preparation of compound 2-2
The compound 2-1 of 24.5g (87.1mmol) is dissolved among the 500mL THF, is cooled to-78 ℃, add 45mL n-BuLi(2.5M, in the hexane), stirred then 1 hour.Subsequently, this mixture adds 15mL B (OMe) 3, and stirred 2 hours, with 250mL aqueous ammonium chloride solution termination reaction.Mixture with 1L EA extraction obtains cleans with 200mL distilled water then.The anhydrous MgSO of the organic layer that obtains 4Drying, reduced pressure treatment to be to remove organic solvent, recrystallization then, thus obtain compound 2-2 (14g, 65%).
The preparation of compound 2-3
Mix 2 of 8.1g (40.6mmol), 4-two chloro-quinazolines, the compound 2-2 of 10g (40.6mmol), the toluene of 200mL, the ethanol of 50mL and the water of 50mL add the Pd (PPh of 1.9g (1.64mmol) then 3) 4And the K of 12.9g (122mmol) 2CO 3This mixture stirred 5 hours at 120 ℃, and was cooled to room temperature, stopped this reaction with the 200mL aqueous ammonium chloride solution afterwards.Mixture with 500mL EA extraction obtains cleans with 50mL distilled water then.The anhydrous MgSO of the organic layer that obtains 4Drying, reduced pressure treatment use silica dioxide gel to filter to remove organic solvent, recrystallization then, thus obtain compound 2-3 (10g, 68%).
The preparation of compound 4
5.0g the compound 1-4 of compound 2-3 (13.7mmol) and 5.54g (16.4mmol) mixes with 100mL toluene, 20mL ethanol and 20mL water, afterwards to the Pd (PPh that wherein adds 1.6g (1.4mmol) 3) 4And the K of 5.7g (41.1mmol) 2CO 3This mixture stirred 5 hours at 120 ℃, and was cooled to room temperature, stopped this reaction with the 20mL aqueous ammonium chloride solution afterwards.Mixture with 250mL EA extraction obtains cleans with 30mL distilled water then.The anhydrous MgSO of the organic layer that obtains 4Drying, reduced pressure treatment use silica dioxide gel to filter to remove organic solvent, recrystallization then, thus obtain compound 4 (5.9g, 69%).
MS/FAB:621.22 (experimental value), 621.73 (calculated values)
[embodiment 1] uses the compound for organic electronic material of the present invention to make OLED equipment
Use the compound for organic electronic material of the present invention to make the OLED device.At first, (15 Ω/) (available from SCP company (Samsung-Corning)) carry out ultrasonic cleaning with trieline, acetone, ethanol and distilled water to the transparency electrode ito thin film that is used for OLED successively that will be made by glass, and are stored in the Virahol before use.Then, the ITO substrate is contained in the substrate folder (folder) of vacuum sediment equipment, with 4,4', 4 " three (N, N-(2-naphthyl)-phenyl amino) triphenylamine (2-TNATA) places the cell (cell) of vacuum sediment equipment; exhaust then makes indoor vacuum tightness be up to 10 -6Holder.Then, apply electric current with evaporation 2-TNATA to described cell, thereby deposit thickness is the hole injection layer of 60nm on the ITO substrate.Subsequently, in another cell of vacuum sediment equipment, add N, N-two (Alpha-Naphthyl)-N, N-phenylbenzene-4,4'-diamines (NPB), by applying electric current to described cell with evaporation NPB, thereby at the thick hole transmission layer of described hole injection layer deposition 20nm.In addition, in 10 -6The The compounds of this invention 3 of holder vacuum-sublimation purifying is packed in the cell of vacuum vapor deposition equipment as substrate material, and will be as two of electroluminescent doping agent-(1-phenyl isoquinolin quinoline base) iridium (III) methyl ethyl diketone acid esters ((piq) 2Ir (acac)) packs in another cell.Then, with different two kinds of materials of speed evaporation, like this by the thick electroluminescence layer of vapour deposition 30nm on the hole transmission layer that is entrained in 4 to 20 weight %.Afterwards, deposit three thick (oxine)-aluminium (III) of 20nm (Alq) as electron transfer layer at electroluminescence layer.Then, the thick quinoline of deposition 1-2nm closes lithium (Liq) as behind the electron injecting layer, uses another vacuum sediment equipment to form the thick Al negative electrode of 150 nm, to make OLED.
The every kind of compound that is used for OLED passes through 10 -6Purifying is carried out in vacuum-sublimation under the holder condition.
As a result of, the electric current under 6.5V voltage flows and is 14.0mA/cm 2, emission 1052cd/cm 2Ruddiness.
[embodiment 2]
Use the same procedure of embodiment 1 to make the OLED device, difference is, uses compound 4 as substrate material in electroluminescence layer.
As a result of, the electric current under 7.5V voltage flows and is 14.0mA/cm 2, emission 1060cd/cm 2Ruddiness.
[embodiment 3]
Use the same procedure of embodiment 1 to make the OLED device, difference is, uses compound 14 as substrate material in electroluminescence layer.
As a result of, the electric current under 6.8V voltage flows and is 14.1mA/cm 2, emission 1030cd/cm 2Ruddiness.
[embodiment 4]
Use the same procedure of embodiment 1 to make the OLED device, difference is, uses compound 20 as substrate material in electroluminescence layer.
As a result of, the electric current under 6.4V voltage flows and is 14.2mA/cm 2, emission 1048cd/cm 2Ruddiness.
[comparative example 1]
Prepare the OLED device as embodiment 1 described same procedure, difference is, in electroluminescence layer, use 4,4'-two (carbazole-9-yl) biphenyl (CBP) replaces compound of the present invention as substrate material, uses two (2-methyl-8-quinoline closes (quinolinato)) (right-phenyl-phenol root closes (phenolato)) aluminium (III) (BAlq) as the hole barrier layer.
As a result of, the electric current under 7.5V voltage flows and is 15.3mA/cm 2, emission 1000cd/cm 2Ruddiness.
Compound for organic electronic material of the present invention has excellent characteristic than traditional material.In addition, the electroluminescence characters that uses the compound with the substituent organic electronic material of fluoranthene of the present invention to have excellence as the organic electroluminescence device of substrate material, driving voltage decline 0.7～1.2V, thus improve power efficiency and improved watt consumption.
Though described preferred implementation of the present invention for illustration purposes, it will be understood by those skilled in the art that various improvement, increase and alternative also are possible, do not deviate from the scope and spirit of the present invention that appended claims limits.
Industrial applicability
Because the compound for organic electronic material of the present invention has good illumination efficiency and excellent life properties, it can be used for making the OLED device with very excellent working life.

Claims (10)

1. compound that is used for organic electronic material of representing with following Chemical formula 1:
Chemical formula 1
Figure DEST_PATH_FDA00003186253500011
Wherein:
L 1And L 2Represent singly-bound, (C3-C30) ring alkylidene group, (C6-C30) arylidene or (C3-C30) heteroarylidene independently;
X 1And X 2Represent CR independently 6Or N, except X 1And X 2All be CR 6Situation;
R 1To R 6Represent hydrogen independently, deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano group, (C3-C30) cycloalkyl, 5-unit to 7-unit Heterocyclylalkyl, (C2-C30) thiazolinyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxyl group, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C6-C30) arylthio, list or two (C1-C30) alkylamino, list or two (C6-C30) arylamino, three (C1-C30) alkyl silyl, two (C1-C30) alkyl (C6-C30) aryl silyl, three (C6-C30) aryl silyl, nitro or hydroxyl; And
L 1And L 2Ring alkylidene group, arylidene and heteroarylidene, and R 1To R 6Alkyl, cycloalkyl, Heterocyclylalkyl, thiazolinyl, alkynyl, aryl and heteroaryl also can further be replaced by one or more substituting groups independently, and described substituting group is selected from: deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano group, (C3-C30) cycloalkyl, 5-unit to 7-unit Heterocyclylalkyl, (C2-C30) thiazolinyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxyl group, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C6-C30) arylthio, list or two (C1-C30) alkylamino, list or two (C6-C30) arylamino, three (C1-C30) alkyl silyl, two (C1-C30) alkyl (C6-C30) aryl silyl, three (C6-C30) aryl silyl, nitro and hydroxyl;
Described heteroarylidene, Heterocyclylalkyl and heteroaryl comprise one or more B of being selected from, N, O, S, P (=O), the heteroatoms of Si and P;
Except *-L 1-R 1It is the situation of hydrogen.
2. the compound for organic electronic material as claimed in claim 1 is characterized in that, described compound is represented by following Chemical formula 2 or 3:
Chemical formula 2
Figure DEST_PATH_FDA00003186253500021
Chemical formula 3
Wherein,
L 1And L 2Represent singly-bound, (C3-C30) ring alkylidene group, (C6-C30) arylidene or (C3-C30) heteroarylidene independently; R 1Be (C6-C30) aryl or (C3-C30) heteroaryl; R 2To R 6Definition as the definition in the claim 1; L 1And L 2Ring alkylidene group, arylidene and heteroarylidene, and R 1Aryl and heteroaryl also can further be replaced by one or more substituting groups independently, described substituting group is selected from: deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano group, (C3-C30) cycloalkyl, 5-unit to 7-unit Heterocyclylalkyl, (C2-C30) thiazolinyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxyl group, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C6-C30) arylthio, list or two (C1-C30) alkylamino, list or two (C6-C30) arylamino, three (C1-C30) alkyl silyl, two (C1-C30) alkyl (C6-C30) aryl silyl, three (C6-C30) aryl silyl, nitro and hydroxyl.
3. the compound for organic electronic material as claimed in claim 1 is characterized in that, described R 1Be the heteroaryl that is selected from following structure:
Wherein,
Y is NR 13, O or S; Z is NR 13, CR 14R 15, O or S; R 11To R 15Be hydrogen independently, deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, halogen, cyano group, (C3-C30) cycloalkyl, 5-unit to 7-unit Heterocyclylalkyl, (C2-C30) thiazolinyl, (C2-C30) alkynyl, (C6-C30) aryl, (C1-C30) alkoxyl group, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) aryl (C1-C30) alkyl, (C6-C30) arylthio, list or two (C1-C30) alkylamino, list or two (C6-C30) arylamino, three (C1-C30) alkyl silyl, two (C1-C30) alkyl (C6-C30) aryl silyl, three (C6-C30) aryl silyl, nitro or hydroxyl; A is monocyclic aromatic rings or many cyclophanes ring or monocycle hetero-aromatic ring or encircles hetero-aromatic ring more.
4. the compound for organic electronic material as claimed in claim 1 is characterized in that, described R 1Be selected from following structure:
Figure DEST_PATH_FDA00003186253500032
Figure DEST_PATH_FDA00003186253500041
R 2, R 3, R 4, R 5And R 6Be hydrogen independently;
L 1Be singly-bound or be selected from following structure:
Figure DEST_PATH_FDA00003186253500042
And
L 2Be singly-bound, phenylene or cyclohexylene.
5. the compound for organic electronic material as claimed in claim 1 is characterized in that, described compound is selected from following compound:
Figure DEST_PATH_FDA00003186253500043
Figure DEST_PATH_FDA00003186253500061
6. organic electroluminescence device, it comprises each described compound for organic electronic material among the claim 1-5.
7. organic electroluminescence device as claimed in claim 6 is characterized in that, described device comprises first electrode; Second electrode; And inserting one or more layers organic layer between described first electrode and second electrode, wherein said organic layer comprises one or more compound and one or more phosphorescent dopants of being used for organic electronic material.
8. organic electroluminescence device as claimed in claim 7, it is characterized in that, described organic layer also comprises one or more amine compound that is selected from aromatic amine compound and styryl aromatic amine compound, or one or more are selected from metal or the complex compound of transition metal, lanthanide series metal and d-transition element of organo-metallic, period 4 and period 5 of the 1st family, the 2nd family of the periodic table of elements.
9. organic electroluminescence device as claimed in claim 7 is characterized in that, described organic layer comprises electroluminescence layer and charge generation layer.
10. organic electroluminescence device as claimed in claim 7 is characterized in that, described organic layer also comprises the organic electro luminescent layer of one or more layers red-emitting, green glow or blue light, with the emission white light.
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Application publication date: 20130710