CN101747373A - Carbazole compound, organic electroluminescence device containing carbazole compound and preparation method thereof - Google Patents
Carbazole compound, organic electroluminescence device containing carbazole compound and preparation method thereof Download PDFInfo
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Abstract
The invention provides a carbazole compound which is at least provided with phosphorylase and a bridging unit with pi-conjugate character; the invention further provides an organic electroluminescence device, comprising a substrate, a first electrode layer is arranged on the substrate, at least one or multiple the organic electroluminescence layers are arranged on the first electrode layer, and a second electrode layer is arranged on the organic electroluminescence layer; the organic electroluminescence layer contains carbazole compound with phosphorus oxide group; the invention further provides a preparation method of the organic electroluminescence device, comprising the following steps: the first electrode is formed on the substrate, at least one or multiple the organic electroluminescence layers are formed on the first electrode, and the e organic electroluminescence layer comprises the carbazole compound with phosphorus oxide group in the technical proposal, and the second electrode is formed on the organic electroluminescence layer; in the invention, the phosphorus oxide group is led in the carbazole compound, so as to lead the carbazole compound to have twin pole carrier transportation capacity.
Description
Technical field
The present invention relates to technical field of organic electroluminescence, relate in particular to a kind of carbazole compound, contain organic electroluminescence device of carbazole compound and preparation method thereof.
Background technology
Organic electroluminescence device is a kind of selfluminous element, and when electric charge was injected between electron injection electrode (first electrode) and the hole injecting electrode (second electrode), electronics and hole were in conjunction with also annihilation subsequently, thereby the generation light.Organic electroluminescence device has characteristics such as voltage is low, brightness is high, the visual angle is wide, response is fast, thermal adaptability is good, is widely used in electronic product indicating meters such as digital camera, mobile phone, MP3.
Electroluminescent organic material is generally singlet fluorescence dye or triplet state phosphorescent coloring, but such material has stronger concentration quenching effect, can reduce the luminous efficiency of luminescent layer, causes the organic electroluminescence device performance lower.Therefore, existing organic electroluminescence device adopts the Subjective and Objective structure mostly, and soon luminescent materials such as fluorescence dye or phosphorescent coloring are entrained in certain proportion and use in the material of main part with good carrier transport ability, to improve device performance.Prior art discloses the multiple material as material of main part, as (M.A.Baldo, S.Lamansky, P.E.Burroes such as Forrest in 1999 and Thompson, M.E.Thompson, S.R.Forrest., Appl.Phys.Lett., 1999,75,4.) with 4,4 '-N, N '-two carbazole biphenyl (CBP) is material of main part, green phosphorescent dye Ir (ppy)
3For dopant material prepares green organic electrofluorescence device, its maximum power efficiency reaches 31lm/W; Forrest (R.J.Holmes, S.R.Forrest, Y.-J.Tung in 2003, R.C.Kwong, J.J.Brown, S.Garon, M.E.Thompson, Appl.Phys.Lett., 2003,82,2422.) with N, N-two carbazyls-3,5-substituted benzene (mCP) are that material of main part, blue light complex of iridium FIrpic are that dopant material prepares the blue-ray organic electroluminescent device, and its maximum power efficiency reaches 8.9 ± 0.9ml/W.In addition, 4,4 ', 4 " N, N ', N " three carbazole triphenylamines (TCTA) also are the material of main parts of using always.
But, existing carbazoles material of main part is all based on hole transport, cause electronics and hole concentration imbalance in the luminescent layer, thereby cause the poor performance of device, efficient low, especially the device of the own efficient of doping blue emitting material on the low side preparation in this type of carbazoles material of main part, maximum power efficiency is lower than 15ml/W, and high-high brightness is lower than 10000cd/m
2
Summary of the invention
In view of this, the technical problem to be solved in the present invention is to provide a kind of carbazole compound, contains organic electroluminescence device of carbazole compound and preparation method thereof, improves the efficient of organic electroluminescence device.
The invention provides a kind of formula (I) compound:
Wherein, Ar
1And Ar
2Be selected from any one structure of following (1)-(59) respectively:
π-Bridge1, π-Bridge2 and π-Bridge3 are the bridging unit with pi-conjugated feature, respectively choosing
Ar
3Be selected from any one structure of following A-G:
R
1Be C
1-8Alkyl.
Preferably, described compound has formula (I-a) structure:
Preferably, described compound has formula (I-b) structure:
Preferably, described compound has formula (I-c) structure:
The present invention also provides a kind of organic electroluminescence device, comprising:
Substrate;
First electrode layer is arranged on substrate;
On described first electrode layer, has one or more layers organic electro luminescent layer at least;
On described organic electro luminescent layer, the second electrode lay is arranged;
Described organic electro luminescent layer comprises the described carbazole compound that contains phosphorus-oxygen groups of technique scheme.
Preferably, described organic electro luminescent layer comprises material of main part and the singlet fluorescence dye or the triplet state phosphorescent coloring that are entrained in the described material of main part, and described material of main part is the described carbazole compound that contains phosphorus-oxygen groups of technique scheme.
Preferably, the doping ratio of described singlet fluorescence dye or triplet state phosphorescent coloring is 0-30wt%.
The present invention also provides a kind of preparation method of organic electroluminescence device, comprising:
On substrate, form first electrode;
Form one or more layers organic electro luminescent layer at least on described first electrode, described organic electro luminescent layer comprises the described carbazole compound that contains phosphorus-oxygen groups of technique scheme;
On organic electro luminescent layer, form second electrode.
Preferably, described organic electro luminescent layer comprises material of main part and the singlet fluorescence dye or the triplet state fluorescence dye that are entrained in the described material of main part, and described material of main part is the described carbazole compound that contains phosphorus-oxygen groups of technique scheme.
Preferably, the doping ratio of described singlet fluorescence dye or triplet state phosphorescent coloring is 0-30wt%.
Compared with prior art, the present invention has introduced phosphorus-oxygen groups in carbazole compound, phosphorus-oxygen groups is an electron acceptor(EA) class group, can improve the electron transport ability of carbazole compound, make the carbazole compound that contains phosphorus-oxygen groups have the bipolar carrier transmittability, i.e. good electron transmittability and cavity transmission ability.Contain the material of main part of the carbazole compound of phosphorus-oxygen groups as organic electroluminescence device, the concentration in electronics and hole in can the balance luminescent layer, thereby improve the performance and the efficient of device, especially can improve the performance and the efficient of blue-ray organic electroluminescent device.Experiment shows, is that the maximum luminous efficiency of the organic electroluminescence device of dopant material preparation can reach 35.0cd/A with the carbazole compound that contains phosphorus-oxygen groups provided by the invention as material of main part, blue light phosphorescent coloring FIrpic, maximum power efficiency can reach 31.4ml/W, and high-high brightness can reach 35100cd/m
2
Description of drawings
The structural representation of the organic electroluminescence device that Fig. 1 provides for the embodiment of the invention;
Luminous efficiency-current density the graphic representation of the organic electroluminescence device that Fig. 2 provides for the embodiment of the invention;
Current density-voltage-brightness curve the figure of the organic electroluminescence device that Fig. 3 provides for the embodiment of the invention;
The electroluminescent spectrum of the organic electroluminescence device that Fig. 4 provides for the embodiment of the invention.
Embodiment
The invention provides a kind of carbazole compound that contains phosphorus-oxygen groups, have formula (I) structure:
Wherein, Ar1 and Ar2 are aromatic substituent, are selected from phenyl ring respectively, contain pyridine ring, naphthalene nucleus or nitrogenous naphthalene nucleus; π-Bridge1 is the bridging unit with conjugate character, and being selected from effective conjugate length respectively is the condensed ring or the aromatic ring system of 1 aromatic ring, 2 aromatic rings or 3 aromatic nucleus.
According to the present invention, the described carbazole compound that contains phosphorus-oxygen groups has following feature: (π's phosphorus-oxygen groups-Bridge) links to each other with bridging that link to each other with carbazyl, that have a pi-conjugated feature unit at least; Phosphorus-oxygen groups and a π-Bridge (π-when Bridge1) linking to each other, two other group Ar that links to each other with phosphorus-oxygen groups
1, Ar
2Be respectively phenyl ring, contain pyridine ring, aromatic substituent such as naphthalene nucleus or nitrogenous naphthalene nucleus or the bridging unit (π-Bridge), be selected from any one structure of above-mentioned (1)-(59) respectively, the Ar that link to each other with carbazyl, have pi-conjugated feature
1And Ar
2Can be identical, also can be different; π-Bridge1, π-Bridge2 and π-Bridge3 are the bridging unit with pi-conjugated feature, its effective conjugate length is 1 aromatic ring, 2 aromatic rings or 3 aromatic rings, π-Bridge1, π-Bridge2 and π-Bridge3 can be identical, also can be different, be selected from any one structure of above-mentioned (101)-(156).
According to the present invention, the described carbazole compound that contains phosphorus-oxygen groups includes but not limited to the compound that following table is listed:
According to the present invention, work as Ar
1And Ar
2When being preferably phenyl ring and π-Bridge1 and being preferably xenyl, compound has formula (I-a) structure, called after CzBPO:
The present invention does not have particular restriction to the preparation method of CzBPO, preferably includes following steps:
With 4,4 '-'-dibromobiphenyl, carbazole are raw material, are catalyzer with salt of wormwood and CuI, with 1,3-dimethyl-2-imidazolidone (DMI) is a reaction medium, is protection gas with the argon gas, and reaction obtains N-(4 '-bromo biphenyl base)-N-carbazole under 100 ℃-250 ℃ condition;
With N-(4 '-bromo biphenyl base)-N-carbazole and diphenyl phosphorus chloride (Ph
2PCl) be raw material, (THF) is reaction medium with tetrahydrofuran (THF), is initiator with n-BuLi, reacts at ambient temperature, with the reaction product H that obtains
2O
2Oxidation obtains product.
Described product is carried out nuclear magnetic resonance spectroscopy, and its proton nmr spectra proves the described product CzBPO for having formula (I-a) structure really.
According to the present invention, work as Ar
1Be preferably phenyl ring and Ar
2When being preferably above-mentioned (57) described structure and π-Bridge1 and π-Bridge2 and being preferably above-mentioned (101) described structure, compound has formula (I-b) structure, called after DCzPO:
The present invention does not have particular restriction to the preparation method of DCzPO, preferably includes following steps:
With paradibromobenzene and phenyl phosphorus dichloride is raw material, is catalyzer with magnesium and iodine, reacts under 0 ℃-100 ℃ condition; With reaction product H
2O
2Oxidation obtains two (4-bromophenyl) phenylphosphine oxides;
With two (4-bromophenyl) phenylphosphine oxides and carbazole is raw material, with t-BuONa, Pd
2(dba)
3And H (t-Bu)
3PBF
4Be catalyzer, reaction obtains product under 50 ℃-200 ℃ condition.
Described product is carried out nuclear magnetic resonance spectroscopy, and its proton nmr spectra proves the described product DCzPO for having formula (I-b) structure really.
According to the present invention, work as Ar
1Be preferably above-mentioned (57) described structure and Ar
2When being preferably above-mentioned (58) described structure and π-Bridge1, π-Bridge2 and π-Bridge3 and being preferably above-mentioned (101) described structure, compound has formula (I-c) structure, called after TCzPO:
The present invention does not have particular restriction to the preparation method of TCzPO, preferably includes following steps:
With paradibromobenzene and phosphorus trichloride is raw material, is that catalyzer reacts under 0 ℃-100 ℃ condition with magnesium and iodine; With reaction product H
2O
2Oxidation obtains three (4-bromophenyl) phenylphosphine oxide;
With three (4-bromophenyl) phenylphosphine oxides and carbazole is raw material, with t-BuONa, Pd
2(dba)
3And H (t-Bu)
3PBF
4Be catalyzer, under 50 ℃-200 ℃ condition, react, obtain product.
Described product is carried out nuclear magnetic resonance spectroscopy, and its proton nmr spectra proves the described product TCzPO for having formula (I-c) structure really.
Compared with prior art, the present invention has introduced phosphorus-oxygen groups in carbazole compound, phosphorus-oxygen groups is an electron acceptor(EA) class group, can improve the electron transport ability of carbazole compound, therefore, the carbazole compound that contains phosphorus-oxygen groups provided by the invention has the bipolar carrier transmittability, i.e. good electron transmittability and cavity transmission ability
The present invention also provides a kind of organic electroluminescence device, comprising:
Substrate;
First electrode layer is arranged on substrate;
On described first electrode layer, has one or more layers organic electro luminescent layer at least;
On described organic electro luminescent layer, the second electrode lay is arranged;
Described organic electro luminescent layer comprises the described carbazole compound that contains phosphorus-oxygen groups of technique scheme.
The present invention does not have particular requirement to described substrate, is preferably glass or plastics, and the thickness of described substrate is preferably 0.3mm-0.7mm.According to the present invention, described first electrode is an anode, for being easy to the material that the hole is injected, is preferably conducting metal or conducting metal oxide, includes but not limited to nickel, platinum, gold, indium tin oxide (ITO) and indium-zinc oxide (IZO).According to the present invention, described organic electro luminescent layer (EML) comprises the carbazole compound that contains phosphorus-oxygen groups that technique scheme is described, have formula (I) structure, be preferably described by technique scheme, as to have formula (I) the structure carbazole compound that contains phosphorus-oxygen groups as material of main part, singlet fluorescence dye or triplet state phosphorescent coloring are formed as dopant material.According to the present invention, in the described luminescent layer, the doping ratio of described singlet fluorescence dye or triplet state phosphorescent coloring is preferably 0-30wt%, and more preferably 1%-20% most preferably is 5%-10%.According to the present invention, the thickness of described luminescent layer is preferably
According to the present invention, described second electrode is a negative electrode, is preferably the metal of low work content, includes but not limited to calcium, barium, aluminium, magnesium and silver.
In order to improve device performance and efficient, between described first electrode and described luminescent layer, preferably include hole transmission layer (HTL).The present invention does not have particular restriction to the material of hole transmission layer, be preferably N, N '-two (3-aminomethyl phenyl)-N, N '-phenylbenzene-1,1 '-phenylbenzene-4,4 '-diamines (TPD) or N, N '-two (1-naphthyl)-N, N '-phenylbenzene-1,1 '-phenylbenzene-4,4 '-diamines (NPB), the thickness of described hole transmission layer is preferably
According to the present invention, between described first electrode and described hole transmission layer, preferably include hole injection layer (HIL).Hole injection layer can reduce the contact resistance between first electrode and the hole transmission layer, increases the injectability in hole.The present invention does not have particular restriction to the material of hole injection layer, be preferably poly-(3, the 4-Ethylenedioxy Thiophene) (PEDOT), poly styrene sulfonate (PSS) or molybdic oxide, the thickness of described hole injection layer is preferably
According to the present invention, between described luminescent layer and described second electrode, preferably include electron transfer layer (ETL), the present invention does not have particular restriction to the material of electron transfer layer, is preferably 8-hydroxyquinoline aluminum (Alq
3), 2-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-1,3,4-oxadiazole (PBD), 1,3,5-three (2-N-phenyl benzimidazolyl-) benzene (TPBI) or 3-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-4-(4-ethylphenyl)-1,2,4-triazole (TAZ), the thickness of described electron transfer layer is preferably
According to the present invention, between described luminescent layer and electron transfer layer, preferably include hole blocking layer (HBL), described hole blocking layer can prevent that exciton or hole migration are in electron transfer layer.The present invention does not have particular restriction to the material of hole blocking layer, be preferably 2,9-dimethyl-4,7-phenylbenzene-1,10-phenanthroline (BCP), 4,7-phenylbenzene-1,10-phenanthroline (BPhen), 1,3,5-three (2-N-phenyl benzimidazolyl-) benzene (TPBI) or 3-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-4-(4-ethylphenyl)-1,2,4-triazole (TAZ), the thickness of described hole blocking layer is preferably
According to the present invention, between the described electron transfer layer and second electrode, preferably include electron injecting layer (EIL), the present invention does not have particular restriction to the material of electron injecting layer, is preferably LiF, NaCl, NaOH, CsF, Cs
2CO
3, Ca (acac)
3, the thickness of described electron injecting layer is preferably
Below in conjunction with accompanying drawing the organic electroluminescence device that the embodiment of the invention provides is described, referring to Fig. 1, the structural representation of the organic electroluminescence device that Fig. 1 provides for the embodiment of the invention, as seen from the figure, described organic electroluminescence device is connected to form successively by substrate (101), first electrode (102), HIL (103), HTL (104), EML (105), HBL (106), ETL (107), EIL (108) and second electrode (109).
The present invention also provides a kind of preparation method of organic electroluminescence device, comprising:
On substrate, form first electrode;
Form one or more layers organic electro luminescent layer at least on described first electrode, described organic electro luminescent layer contains the described carbazole compound that contains phosphorus-oxygen groups of technique scheme;
On organic electro luminescent layer, form second electrode.
According to the present invention, at first on substrate, form first electrode, the present invention does not have particular restriction to described formation method, is preferably method well known to those skilled in the art.The present invention does not have particular requirement to described substrate, is preferably glass or plastics, and the thickness of described substrate is preferably 0.3mm-0.7mm.According to the present invention, described first electrode is an anode, for being easy to the material that the hole is injected, is preferably conducting metal or conducting metal oxide, includes but not limited to nickel, platinum, gold, indium tin oxide (ITO) and indium-zinc oxide (IZO).
According to the present invention, on first electrode, be formed with organic electroluminescent layer.The present invention does not have particular restriction to the formation method, is preferably method well known to those skilled in the art, includes but not limited to methods such as vacuum codeposition.According to the present invention, described organic electro luminescent layer (EML) comprises the carbazole compound that contains phosphorus-oxygen groups that technique scheme is described, have formula (I) structure, be preferably described by technique scheme, as to have formula (I) the structure carbazole compound that contains phosphorus-oxygen groups as material of main part, singlet fluorescence dye or triplet state phosphorescent coloring are formed as dopant material.According to the present invention, in the described luminescent layer, the doping ratio of described singlet fluorescence dye or triplet state phosphorescent coloring is preferably 0-30wt%, and more preferably 1%-20% most preferably is 5%-10%.According to the present invention, the thickness of described luminescent layer is preferably
According to the present invention, before forming luminescent layer, preferred cleaning has the substrate of first electrode, and the substrate after cleaning is carried out ultraviolet ray, ozone or Cement Composite Treated by Plasma.
According to the present invention, on organic electro luminescent layer, form second electrode, the present invention does not have particular restriction to the formation method, is preferably method well known to those skilled in the art, includes but not limited to deposition.Described second electrode is a negative electrode, is preferably the metal of low work content, includes but not limited to calcium, barium, aluminium, magnesium and silver.
In order to improve device performance and efficient, before forming luminescent layer, preferably on described first electrode, form hole transmission layer (HTL), the present invention does not have particular restriction to described formation method, is preferably vacuum moulding machine.The present invention does not have particular restriction to the material of hole transmission layer, be preferably N, N '-two (3-aminomethyl phenyl)-N, N '-phenylbenzene-1,1 '-phenylbenzene-4,4 '-diamines (TPD) or N, N '-two (1-naphthyl)-N, N '-phenylbenzene-1,1 '-phenylbenzene-4,4 '-diamines (NPB), the thickness of described hole transmission layer is preferably
According to the present invention, before forming hole transmission layer, preferably on first electrode, form hole injection layer (HIL), hole injection layer can reduce the contact resistance between first electrode and the hole transmission layer, increases the injectability in hole.The present invention does not have particular restriction to described formation method, is preferably vacuum moulding machine or vacuum evaporation.Can the present invention the material of hole injection layer not be had particular restriction, be preferably poly-(3, the 4-Ethylenedioxy Thiophene) (PEDOT), poly styrene sulfonate (PSS) or molybdic oxide, the thickness of described hole injection layer is preferably
According to the present invention, before forming described second electrode, preferably on luminescent layer, form electron transfer layer (ETL), the present invention does not have particular restriction to described formation method, is preferably vacuum moulding machine.The present invention does not have particular restriction to the material of electron transfer layer, is preferably 8-hydroxyquinoline aluminum (Alq
3), 2-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-1,3,4-oxadiazole (PBD), 1,3,5-three (2-N-phenyl benzimidazolyl-) benzene (TPBI) or 3-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-4-(4-ethylphenyl)-1,2,4-triazole (TAZ), the thickness of described electron transfer layer is preferably
According to the present invention, between the formation electron transfer layer, preferably on luminescent layer, form hole blocking layer (HBL), described hole blocking layer can prevent that exciton or hole migration are in electron transfer layer.The present invention does not have particular restriction to described formation method, is preferably vacuum moulding machine.The present invention does not have particular restriction to the material of hole blocking layer, be preferably 2,9-dimethyl-4,7-phenylbenzene-1,10-phenanthroline (BCP), 4,7-phenylbenzene-1,10-phenanthroline (BPhen), 1,3,5-three (2-N-phenyl benzimidazolyl-) benzene (TPBI) or 3-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-4-(4-ethylphenyl)-1,2,4-triazole (TAZ), the thickness of described hole blocking layer is preferably
According to the present invention, after forming described electron transfer layer, form before second electrode, be preferably included in and form electron injecting layer (EIL) on the electron transfer layer, the present invention does not have particular restriction to described formation method, is preferably vacuum moulding machine.The present invention does not have particular restriction to the material of electron injecting layer, is preferably LiF, NaCl, NaOH, CsF, Cs
2CO
3, Ca (acac)
3, the thickness of described electron injecting layer is preferably
The preparation method of the organic electroluminescence device that the embodiment of the invention is provided below in conjunction with accompanying drawing is described, referring to Fig. 1, the structural representation of the organic electroluminescence device that Fig. 1 provides for the embodiment of the invention, its preparation method may further comprise the steps: form first electrode (102) at substrate (101); Clean described sinking to the bottom with Virahol, acetone and other organic solvent then; Go up the HIL (103) that forms the molybdic oxide material by the mode of vacuum evaporation at first electrode (102); On HIL, form HTL (104) in vacuum-deposited mode; Mode with the vacuum codeposition on HTL forms EML (105), on EML, form HBL (106) with vacuum-deposited method, on HBL, form ETL (107) with vacuum-deposited method, on ETL, form EIL (108), on EIL, form second electrode (109) at last, obtain organic electroluminescence device as shown in Figure 1.
Compared with prior art, the present invention adopts and contains the material of main part of the carbazole compound of phosphorus-oxygen groups as organic electroluminescence device, because phosphorus-oxygen groups is an electron acceptor(EA) class group, can improve the electron transport ability of carbazole compound, therefore, the carbazole compound that contains phosphorus-oxygen groups provided by the invention has the bipolar carrier transmittability, be good electron transmittability and cavity transmission ability, the concentration in electronics and hole in can the balance luminescent layer, thereby improve the performance and the efficient of device, especially can improve the performance and the efficient of blue-ray organic electroluminescent device.Experiment shows, is that the maximum luminous efficiency of the organic electroluminescence device of dopant material preparation reaches 35.0cd/A with the carbazole compound that contains phosphorus-oxygen groups provided by the invention as material of main part, blue light phosphorescent coloring FIrpic, maximum power efficiency reaches 31.4ml/W, and high-high brightness reaches 35100cd/m
2
In order further to understand the present invention, carbazole compound provided by the invention, the organic electroluminescence device and preparation method thereof that contains carbazole compound are described below in conjunction with embodiment.
In reaction flask, add 75mmol (23g) 4,4 '-'-dibromobiphenyl, 50mmol (8.3g) carbazole, 100mmol (14g) salt of wormwood, 10mmol (2.0g) CuI and 10mL1,3-dimethyl-2-imidazolidone (DMI) under argon shield, is heated to 190 ℃ of reactions 20 hours; After the cooling, reaction mixture is dissolved with methylene dichloride, wash three times, use anhydrous sodium sulfate drying, filter then, concentrate, silicagel column obtains 7.9gN-after separating (4 '-bromo biphenyl base)-the N-carbazole, productive rate 40.2% through phenetic analysis, confirms that this product is N-(4 '-bromo biphenyl base)-N-carbazole.
1H?NMR(300MHz，CDCl
3)[ppm]：δ8.16(d，J＝7.8Hz，2H)，7.78(d，J＝8.7Hz，2H)，7.62-7.66(m，4H)，7.55(d，J＝8.7Hz，2H)，7.40-7.48(m，4H)，7.31(td，J＝7.2，1.5Hz，2H)；
In the exsiccant reaction flask, add 3mmol (1.2g) N-(4 '-bromo biphenyl base)-N-carbazole and 50mL exsiccant tetrahydrofuran (THF) (THF); under argon shield; dry ice acetone bath is cooled to-78 ℃; in reaction flask, add 4.5mmoln-BuLi (1.8mL2.5M hexane solution), react and add 6.75mmol (1.18mL) diphenyl phosphorus chloride (Ph after 1 hour
2PCl), slowly rise to room temperature reaction after 24 hours, slowly add 2mLH
2O
2Stirred 2 hours, described reaction mixture is poured in the water, use dichloromethane extraction, wash three times, use dried over anhydrous sodium carbonate then, filter, concentrate, silicagel column obtains the 1.1g product after separating, productive rate 70.6% through phenetic analysis, confirms that this product is for having formula (I-a) structure C zBPO.
1HNMR(300MHz，DMSO)[ppm]：δ8.28(d，J＝7.8Hz，2H)，8.03(d，J＝8.4Hz，2H)，7.99(dd，J＝8.4，2.4Hz，2H)，7.57-7.79(m，14H)，7.43-7.49(m，4H)，7.32(td，J＝6.9，2.4Hz，2H)。
31P?NMR[ppm]：δ25.07。
Reaction formula is as follows:
Embodiment 2
In the exsiccant reaction flask, add 200mmol (4.8g) magnesium chips and a small amount of iodine; argon shield adds the 10mL dry THF down; slowly drip the THF solution that 150mL contains 200mmol (47.2g) paradibromobenzene, 50 ℃ were reacted 4 hours, added 90mmol (16.1g) phenyl phosphorus dichloride (PhPCl
2), continue reaction 24 hours.Slowly add 20mL H
2O
2Stirred 2 hours, reaction mixture is poured in the water, use dichloromethane extraction, wash three times, use dried over anhydrous sodium carbonate, filter, concentrate, silicagel column obtains two (4-bromophenyl) phenylphosphine oxides of 22.6g, productive rate 57.7% after separating, through phenetic analysis, confirm that this product is two (4-bromophenyl) phenylphosphine oxides really.
1H?NMR(300MHz，CDCl
3)[ppm]：δ7.58-7.68(m，7H)，7.48-7.55(m，6H)。
In the exsiccant reaction flask, add 0.5mmol (0.22g) two (4-bromophenyl) phenylphosphine oxide, 3mmol (0.50g) carbazole, 3mmol (0.29g) t-BuONa, 0.02mmol (9.2mg) Pd
2(dba)
3And 0.01mmol (5.8mg) H (t-Bu)
3PBF
4, under argon shield, add 20mL dry toluene (toluene), 100 ℃ were reacted 12 hours.Reaction mixture is poured in the water, and dichloromethane extraction is washed three times, anhydrous sodium sulfate drying filters, concentrates, silicagel column obtains 0.22gDCzPO, productive rate 71.4% after separating, through phenetic analysis, confirm this product DCzPO for having formula (I-b) structure really.
1HNMR(400MHz，DMSO)[ppm]：δ8.25(d，J＝7.6Hz，4H)，8.03(d，J＝8.4Hz，2H)，8.00(d，J＝8.8Hz，2H)，7.89(d，J＝8.4Hz，4H)，7.83-7.86(m，2H)，7.65-7.72(m，3H)，7.53(d，J＝8.4Hz，4H)，7.43(t，J＝7.2Hz，4H)，7.31(t，J＝7.2Hz，4H)。
31P?NMR[ppm]：δ24.44。
Reaction formula is as follows:
In the exsiccant reaction flask, add 100mmol (2.4g) magnesium chips and a small amount of iodine; argon shield adds the 10mL dry THF down; slowly drip the THF solution that 100mL contains 100mmol (23.6g) paradibromobenzene, 50 ℃ were reacted 4 hours, added 30mmol (4.12g) phosphorus trichloride (PCl
3), continue reaction 24 hours.Slowly add 10mLH
2O
2Stirred 2 hours, and reaction mixture was poured in the water into dichloromethane extraction, wash three times, anhydrous sodium sulfate drying filters, concentrates, silicagel column obtains 8.3g three (4-bromophenyl) oxygen phosphorus after separating, productive rate 56.7% through phenetic analysis, confirms that this product is three (4-bromophenyl) oxygen phosphorus really.
1H?NMR(400MHz，CDCl
3)[ppm]：δ7.62(dd，J＝2.0，8.4Hz，6H)，7.50(d，J＝8.4Hz，3H)，7.48(d，J＝8.4Hz，3H)。
In the exsiccant reaction flask, add 8mmol (4.12g) three (4-bromophenyl) oxygen phosphorus, 36mmol (6.01g) carbazole, 36mmol (3.44g) t-BuONa and 0.18mmol (162mg) Pd
2(dba)
3, under argon shield, add (t-Bu) of 30mL dry toluene (toluene) and 0.35mmol
3P (14.4mL1% hexane solution), 100 ℃ were reacted 12 hours.Reaction mixture is poured in the water, and dichloromethane extraction is washed three times, anhydrous sodium sulfate drying filters, concentrates, silicagel column obtains 0.17gTCzPO, productive rate 67.4% after separating, through phenetic analysis, confirm this product TCzPO for having formula (I-C) structure really.
1HNMR(300MHz，CDCl
3)：δ8.09(d，J＝7.5Hz，6H)，8.03(dd，J＝10.0，3.2Hz，6H)，7.79(dd，J＝8.5，2.2Hz，6H)，7.49(d，J＝8.2Hz，6H)，7.38(t，J＝8.2Hz，6H)，7.26(t，J＝7.5Hz，6H)。
31P?NMR[ppm]：δ24.21。
Reaction formula is as follows:
Embodiment 4
Prepare organic electroluminescence device according to following steps:
With plastics as substrate; On plastic, form first electrode of indium tin oxide (ITO) material; On first electrode, form molybdic oxide (MoO
3) material, thickness is the hole injection layer of 8nm; On hole injection layer, form N with vacuum-deposited method, N '-two (1-naphthyl)-N, N '-phenylbenzene-1,1 '-phenylbenzene-4,4 '-diamines (NPB) material, thickness is the hole transmission layer of 80nm; Forming thickness with the method for vacuum codeposition on hole transmission layer is the organic electro luminescent layer of 20nm, and described luminescent layer is entrained in by blue light phosphorescent coloring (FIrpic) among the TCzPO of embodiment 3 preparations to be formed, and the doping ratio of FIrpic is 8wt%; On luminescent layer, form 3-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-4-(4-ethylphenyl)-1,2 by vacuum-deposited method, 4-triazole (TAZ) material, thickness is hole blocking layer and the electron transfer layer of 40nm; On electron transfer layer, form the LiF material, thickness is the electron injecting layer of 1nm; Second electrode of depositing Al material on electron injecting layer, thickness is 100nm, obtains having organic EL device of following structure:
ITO/MoO
3(8nm)/NBP(80nm)/TCzPO:FIrpic(20nm)/TAZ(40nm)/LiF(1nm)/A1(100nm)
Described organic EL device is carried out performance test, the result is referring to Fig. 2, Fig. 3 and Fig. 4, luminous efficiency-current density the graphic representation of the organic electroluminescence device that Fig. 2 provides for the embodiment of the invention, the electroluminescent spectrum of the organic electroluminescence device that the current density-voltage-brightness curve figure of the organic electroluminescence device that Fig. 3 provides for the embodiment of the invention, Fig. 4 provide for the embodiment of the invention.As seen from the figure, the maximum luminous efficiency of the organic electroluminescence device that present embodiment provides is 35.0cd/A, and maximum power efficiency is 31.4lm/W, and high-high brightness is 35100cd/m
2
Prepare organic electroluminescence device according to following steps:
With plastics as substrate; On plastic, form first electrode of indium tin oxide (ITO) material; On first electrode, form molybdic oxide (MoO
3) material, thickness is the hole injection layer of 8nm; On hole injection layer, form N with vacuum-deposited method, N '-two (1-naphthyl)-N, N '-phenylbenzene-1,1 '-phenylbenzene-4,4 '-diamines (NPB) material, thickness is the hole transmission layer of 80nm; Forming thickness with the method for vacuum codeposition on hole transmission layer is the organic electro luminescent layer of 20nm, and described luminescent layer is entrained in by blue light phosphorescent coloring (FIrpic) among the CzBPO of embodiment 1 preparation to be formed, and the doping ratio of FIrpic is 8wt%; On luminescent layer, form 3-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-4-(4-ethylphenyl)-1,2 by vacuum-deposited method, 4-triazole (TAZ) material, thickness is hole blocking layer and the electron transfer layer of 40nm; On electron transfer layer, form the LiF material, thickness is the electron injecting layer of 1nm; Second electrode of depositing Al material on electron injecting layer, thickness is 100nm, obtains having organic EL device of following structure:
ITO/MoO
3(8nm)/NBP(80nm)/CzBPO:FIrpic(20nm)/TAZ(40nm)/LiF(1nm)/Al(100nm)
Described organic EL device is carried out performance test, and the result shows that the maximum luminous efficiency of the organic electroluminescence device that present embodiment provides is 9.8cd/A, and maximum power efficiency is 7.61m/W, and high-high brightness is 12400cd/m
2
Embodiment 6
Prepare organic electroluminescence device according to following steps:
With plastics as substrate; On plastic, form first electrode of indium tin oxide (ITO) material; On first electrode, form molybdic oxide (MoO
3) material, thickness is the hole injection layer of 8nm; On hole injection layer, form N with vacuum-deposited method, N '-two (1-naphthyl)-N, N '-phenylbenzene-1,1 '-phenylbenzene-4,4 '-diamines (NPB) material, thickness is the hole transmission layer of 80nm; Forming thickness with the method for vacuum codeposition on hole transmission layer is the organic electro luminescent layer of 20nm, and described luminescent layer is entrained in by blue light phosphorescent coloring (FIrpic) among the DCzPO of embodiment 2 preparations to be formed, and the doping ratio of FIrpic is 8wt%; On luminescent layer, form 3-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-4-(4-ethylphenyl)-1,2 by vacuum-deposited method, 4-triazole (TAZ) material, thickness is hole blocking layer and the electron transfer layer of 40nm; On electron transfer layer, form the LiF material, thickness is the electron injecting layer of 1nm; Second electrode of depositing Al material on electron injecting layer, thickness is 100nm, obtains having organic EL device of following structure:
ITO/MoO
3(8nm)/NBP(80nm)/DCzPO:FIrpic(20nm)/TAZ(40nm)/LiF(1nm)/Al(100nm)
Described organic EL device is carried out performance test, and the result shows that the maximum luminous efficiency of the organic electroluminescence device that present embodiment provides is 33.2cd/A, and maximum power efficiency is 28.9lm/W, and high-high brightness is 33800cd/m
2
Comparative example 1
Prepare organic electroluminescence device according to following steps:
With plastics as substrate; On plastic, form first electrode of indium tin oxide (ITO) material; On first electrode, form molybdic oxide (MoO
3) material, thickness is the hole injection layer of 8nm; On hole injection layer, form N with vacuum-deposited method, N '-two (1-naphthyl)-N, N '-phenylbenzene-1,1 '-phenylbenzene-4,4 '-diamines (NPB) material, thickness is the hole transmission layer of 80nm; Method formation thickness with the vacuum codeposition on hole transmission layer is the organic electro luminescent layer of 20nm, and described luminescent layer is entrained in the TCTA material of main part by blue light phosphorescent coloring (FIrpic) to be formed, and the doping ratio of FIrpic is 8wt%; On luminescent layer, form 3-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-4-(4-ethylphenyl)-1,2 by vacuum-deposited method, 4-triazole (TAZ) material, thickness is hole blocking layer and the electron transfer layer of 40nm; On electron transfer layer, form the LiF material, thickness is the electron injecting layer of 1nm; Second electrode of depositing Al material on electron injecting layer, thickness is 100nm, obtains having organic EL device of following structure:
ITO/MoO
3(8nm)/NBP(80nm)/TCTA:FIrpic(20nm)/TAZ(40nm)/LiF(1nm)/Al(100nm)
Described organic EL device is carried out performance test, and the result shows that the maximum luminous efficiency of the organic electroluminescence device that present embodiment provides is 15.9cd/A, and maximum power efficiency is 13.0lm/W, and high-high brightness is 7200cd/m
2
The explanation of above embodiment just is used for helping to understand method of the present invention and core concept thereof.Should be pointed out that for those skilled in the art, under the prerequisite that does not break away from the principle of the invention, can also carry out some improvement and modification to the present invention, these improvement and modification also fall in the protection domain of claim of the present invention.
Claims (10)
1. a formula (I) compound:
(I)
Wherein, Ar
1And Ar
2Be selected from any one structure of following (1)-(59) respectively:
π-Bridge1, π-Bridge2 and π-Bridge3 are the bridging unit with pi-conjugated feature, are selected from any one structure of following (101)-(156) respectively:
Ar
3Be selected from any one structure of following A-G:
R
1Be C
1-8Alkyl.
2. compound according to claim 1 has formula (I-a) structure:
3. compound according to claim 1 has formula (I-b) structure:
4. compound according to claim 1 has formula (I-c) structure:
5. an organic electroluminescence device is characterized in that, comprising:
Substrate;
First electrode layer is arranged on substrate;
On described first electrode layer, has one or more layers organic electro luminescent layer at least;
On described organic electro luminescent layer, the second electrode lay is arranged;
Described organic electro luminescent layer comprises any described compound of claim 1-4.
6. organic electroluminescence device according to claim 5, it is characterized in that, described organic electro luminescent layer comprises material of main part and the singlet fluorescence dye or the triplet state phosphorescent coloring that are entrained in the described material of main part, and described material of main part is any described compound of claim 1-4.
7. organic electroluminescence device according to claim 6 is characterized in that, the doping ratio of described singlet fluorescence dye or triplet state phosphorescent coloring is 0-30wt%.
8. the preparation method of an organic electroluminescence device is characterized in that, comprising:
On substrate, form first electrode;
Form one or more layers organic electro luminescent layer at least on described first electrode, described organic electro luminescent layer contains any described compound of claim 1-4;
On organic electro luminescent layer, form second electrode.
9. method according to claim 8, it is characterized in that, described organic electro luminescent layer comprises material of main part and the singlet fluorescence dye or the triplet state fluorescence dye that are entrained in the described material of main part, and described material of main part is any described compound of claim 1-4.
10. method according to claim 9 is characterized in that, the doping ratio of described singlet fluorescence dye or triplet state phosphorescent coloring is 0-30wt%.
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