CN104513661A - Organic luminescence material and applications thereof - Google Patents
Organic luminescence material and applications thereof Download PDFInfo
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- CN104513661A CN104513661A CN201310460233.5A CN201310460233A CN104513661A CN 104513661 A CN104513661 A CN 104513661A CN 201310460233 A CN201310460233 A CN 201310460233A CN 104513661 A CN104513661 A CN 104513661A
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- VKGFLWDJQIVXSN-UHFFFAOYSA-N c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c1c2[s]c(cccc3)c3c2ccc1)c(cc1)ccc1-c1c2[s]c(cccc3)c3c2ccc1 Chemical compound c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c1c2[s]c(cccc3)c3c2ccc1)c(cc1)ccc1-c1c2[s]c(cccc3)c3c2ccc1 VKGFLWDJQIVXSN-UHFFFAOYSA-N 0.000 description 2
- PUIGAFXFSIGZHY-UHFFFAOYSA-N c1c(-c2ccccc2)[s]c(-c(cc2)ccc2N(c2ccccc2)c(cc2)ccc2-c(cc2)ccc2N(c2ccccc2)c(cc2)ccc2-c2ccc(-c3ccccc3)[s]2)c1 Chemical compound c1c(-c2ccccc2)[s]c(-c(cc2)ccc2N(c2ccccc2)c(cc2)ccc2-c(cc2)ccc2N(c2ccccc2)c(cc2)ccc2-c2ccc(-c3ccccc3)[s]2)c1 PUIGAFXFSIGZHY-UHFFFAOYSA-N 0.000 description 2
- XANHMTXPZQQSMK-UHFFFAOYSA-N Brc(cc1)cc2c1[nH]c1c2c(cccc2)c2c2c1c1ccccc1cc2 Chemical compound Brc(cc1)cc2c1[nH]c1c2c(cccc2)c2c2c1c1ccccc1cc2 XANHMTXPZQQSMK-UHFFFAOYSA-N 0.000 description 1
- XUFUINIYNCMTNL-UHFFFAOYSA-N [O-][N+](c(c(-c1cc2c(cccc3)c3ccc2c2ccccc12)c1)ccc1Br)=O Chemical compound [O-][N+](c(c(-c1cc2c(cccc3)c3ccc2c2ccccc12)c1)ccc1Br)=O XUFUINIYNCMTNL-UHFFFAOYSA-N 0.000 description 1
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Abstract
The present invention relates to an organic luminescence material represented by a formula (I), wherein Ar1-Ar9 are independently selected from H, C6-C30 substituted or unsubstituted aromatic hydrocarbon, C6-C30 substituted or unsubstituted fused ring aromatic hydrocarbon, C6-C30 substituted or unsubstituted fused heterocycle, or five-membered/six-membered heterocycle or substituted heterocycle, C6-C30 substituted or unsubstituted triphenylamine or aryl ether, and C1-C12 substituted or unsubstituted aliphatic alkyl, and Ar1-Ar8 are not simultaneously H. The present invention further provides applications of the compounds in organic electroluminescent devices, especially applications of the compounds as hole injection materials, hole transport layer materials, fluorescence host materials or light emitting materials in OLED devices. The formula (I) is defined in the instruction.
Description
Technical field
The present invention relates to a kind of novel organic luminescent material, particularly relate to a kind of for the compound of organic electroluminescence device and the application in organic electroluminescence device.
background technology
Display of organic electroluminescence (hereinafter referred to as OLED) has, composition wide, lightweight from main light emission, low-voltage direct-current driving, all solidstate, visual angle and a series of advantage such as technique is simple, compared with liquid-crystal display, display of organic electroluminescence does not need backlight, visual angle is large, power is low, and its response speed can reach 1000 times of liquid-crystal display, and its manufacturing cost is but lower than the liquid-crystal display of equal resolving power, therefore, organic electroluminescence device has broad application prospects.
The restructuring of what the generation of organic electroluminescent was leaned on the is current carrier (electronics and hole) transmitted in organic electroluminescence material, as everyone knows, the electroconductibility of organic materials is very poor, with inorganic semiconductor unlike, do not have being with of continuity in organic semiconductor, the transmission of current carrier is commonly used jump theory to describe, namely under the driving of an electric field, electronics is being excited or is being injected in the lumo energy of molecule, via jumping to the lumo energy of another molecule to reach the object of transferring charge.In order to organic electroluminescence device can be made to reach breakthrough in application aspect, the difficulty of organic materials charge injection and transmittability difference must be overcome.Scientists is by the adjustment of device architecture, such as increase the number of device organic material layer, and make different organic layers play the part of different roles, the functional materials such as had helps electronics to inject from negative electrode and hole from anode, some materials help the transmission of electric charge, some materials then play the effect of block electrons and hole transport, certainly in organic electroluminescent, the luminescent material of most important shades of colour also will reach the object matched with adjacent functional material, the result of excellent in efficiency life-span long organic electroluminescence device normally optimization collocation of device architecture and various organic materials, this functionalization material just designing and developing various structure for chemists provides great opportunities and challenges.
The hole always used in organic electroluminescent device is injected and transport material is generally derivative of tri-arylamine group (such as bright dipping patent: publication number CN1152607C, publication date 2004,6,2), its general constructional feature is, as injecting material, in a molecule, its tertiary aromatic amine structure unit is at least more than three, and separate with a phenyl ring between two N, see formula 1; As transport material, in a molecule, its tertiary aromatic amine structure unit is generally two, and separates with biphenyl between two N, and in this kind of material, typical example is NPB, and its structure is shown in formula 2.
In recent years, the research of this kind of material has had some new progresses, introduce one or more thienyl in the molecule, or introduce one or more benzothienyl, see formula 3 and formula 4(bright dipping patent: publication number CN101506191A, publication date 2009,8,12), result is the Hole injection capacity considerably increasing material; As transport material, when the tertiary aromatic amine structure unit carbazole of in material or diphenylene-oxide being replaced, the transmittability of material all has a more substantial increase.See formula 5 and formula 6(bright dipping patent: publication number CN102334210A, the applying date 2012,1,25; Publication number: WO 2010/114017A1, publication date 2010,10,7).
summary of the invention
The object of the present invention is to provide a class novel organic luminescent material, such luminous organic material may be used for ORGANIC ELECTROLUMINESCENCE DISPLAYS field.
For this reason, the technical scheme that the present invention takes is:
A kind of luminous organic material, has structure as shown in the formula (I):
Wherein:
Ar
1-A
9independently be selected from H, the substituted or unsubstituted aromatic hydrocarbon group of C6-C30, the substituted or unsubstituted condensed-nuclei aromatics group of C6-C30, the substituted or unsubstituted fused heterocycle group of C6-C30, or five yuan, hexa-atomic heterocycle or substituted heterocycle, the substituted or unsubstituted triaryl amine group of C6-C30, or aryl oxide group, one in the substituted or unsubstituted aliphatic alkyl group of C1-C12 is H when Ar1-Ar8 is different.
Further, described Ar5, Ar6, Ar7, Ar8, Ar9 are H simultaneously.
Further, described Ar4 is selected from phenyl, substituted-phenyl, xenyl, naphthyl, anthryl, phenanthryl, perylene base, pyrenyl.
Further, described Ar1, Ar2, Ar3 are separately selected from phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, Qu Ji, benzo phenanthryl, substituted-phenyl, substituted naphthyl, replacement pyrenyl, replace and bend base, replace anthryl, carbazyl, triphenylenyl, substituted carbazole base, dibenzothiophene base, substituted diphenylamine thiophthene base, dibenzofuran group, substituted diphenylamine furyl, triarylamine, replacement triarylamine.
In order to more clearly demonstrate content of the present invention, lower mask body describes the preferred structure of the compound that the present invention relates to:
The invention provides a kind of luminous organic material, be applied in organic electroluminescence device.
Further, described luminous organic material can be used as hole-injecting material, hole mobile material or material of main part in organic electroluminescence device.
Present invention also offers a kind of organic electroluminescence device, comprise substrate, and form anode layer, organic luminescence function layer and cathode layer on the substrate successively;
Described organic luminescence function layer comprises hole transmission layer, organic luminous layer and electron transfer layer;
The substrate material of described hole transmission layer contains described luminous organic material.
Present invention also offers a kind of organic electroluminescence device, comprise substrate, and form anode layer, organic luminescence function layer and cathode layer on the substrate successively;
Described organic luminescence function layer comprises hole transmission layer, organic luminous layer and electron transfer layer;
The substrate material of described organic luminous layer contains described luminous organic material.
For convenience of description, in the application's subsequent content, the hole mobile material of indication is the substrate material of hole transmission layer, and material of main part is the substrate material of organic luminous layer.
Compared with prior art, tool of the present invention has the following advantages:
In the present invention, we have proposed a kind of novel material, is with at parent nucleus
upper key connects a series of compounds that a carbazole is general formula, this novel material is not only fitted collaborative agent material but also is made hole mobile material, when parent nucleus connecting condensed-nuclei aromatics, such material is suitable as light emitting host material, be applied on device, can improve a lot to luminous efficiency, device lifetime is longer.When parent nucleus being connected with triaryl amine or fused heterocycle aromatic hydrocarbons, such as carbazole group, dibenzothiophene group, diphenylene-oxide group etc., such material is suitable as hole mobile material.In red device as hole mobile material application better, the use of material of the present invention, what reduce device opens bright voltage to this novel material, improves the luminous efficiency of device, adds the work-ing life of device.
(2) preparation is simple for the compounds of this invention, and these compounds have good thermostability, high hole mobility, with the electroluminescent device that this material makes, the bright voltage that opens of device reduces greatly, luminous efficiency increases, and significantly increases the work-ing life of device simultaneously, can be used as the material of main part of hole mobile material or organic luminous layer in organic electroluminescence device.
Accompanying drawing explanation
In order to make content of the present invention more easily be understood, with Gaussian03B3LYP/6-31G(d in the present invention) method tries to achieve the highest occupied molecular orbital(HOMO) (HOMO) of compound, lowest unoccupied molecular orbital (LUMO) and triplet (T1) respectively.
Fig. 1 is the highest occupied molecular orbital(HOMO) of compound 9 in the embodiment of the present invention 10, and HOMO energy level is-5.040ev, triplet T1=1.7362ev;
Fig. 2 is the lowest unoccupied molecular orbital of compound 9 in the embodiment of the present invention 10, and lumo energy is-1.542ev.
Embodiment
Basic raw material used in the present invention, 6-bromine
2,4-bis-bromo nitrobenzene, 2,5-bis-bromo nitrobenzene, and bromo carbazole derivative, bromo diphenylene-oxide, bromo dibenzothiophene, bromo
derivative, bromo triphenylene, bromo pyrene, bromo anthracene derivant etc., can buy in each large industrial chemicals market at home, above-mentioned each bromo condensed-nuclei aromatics can synthesize its boric acid derivatives with usual laboratory methods.
Embodiment 1
Preparation embodiment for intermediate of the present invention:
Main intermediate
the synthesis of-6-boric acid
By the 6-bromine of 6.12g
(molecular weight 306,0.02mol) is dissolved in the THF of 100ml drying, and-80 DEG C drip normal-butyl reason 10ml(2.5M, 0.025mol), stir 15min, then drip triisopropyl boric acid ester 16ml.Hydrolysis, regulate pH to separate out white boric acid derivatives 5.5g to neutral, productive rate is close to 100%.
Embodiment 2
The synthesis of compound 1,
(1) the first step
1000 milliliters of a bite bottles, join magnetic agitation, add
-6-boric acid 5.5g(molecular weight 272,0.02mol), 2,4-bis-bromo nitrobenzene 5.84g(molecular weight 278,0.021mol), Pd (PPh3) 4 usage quantity 1.5g(molecular weight 1154,0.0013mol), sodium carbonate 150ml(2M), toluene 150ml, ethanol 150ml.After argon replaces, backflow, with TLC monitoring reaction, react completely after 3 hours, cooling, separated basic unit, evaporate to dryness, the ethyl acetate/petroleum ether with 1/10 carries out post separation, obtains, 7.82g product, molecular weight 427, productive rate 91.5%.
(2) second step
50 milliliters of a bite bottles, join magnetic agitation, add the final product 7.82g(molecular weight 427,0.0183mol of the first step), triphenylphosphine 5.76g(molecular weight 262,0.022mol), orthodichlorobenzene 150ml.Mixture is heated to 175 DEG C, stirs, by TCL board monitoring reaction process, reacts and complete for 15 hours.Cooling, solvent evaporation in vacuo, washing, dry, with pillar layer separation, ethyl acetate and petroleum ether mixtures drip washing, obtain target molecule 6.5g, molecular weight 395, productive rate 89.6%.
(3) the 3rd steps
500 milliliters of a bite bottles, join magnetic agitation, add second step final product 6.5g(molecular weight 395,0.0164mol), to methiodide benzene 5.45g(molecular weight 218,0.025mol), cuprous iodide 1.0g(molecular weight 190,0.00526mol), salt of wormwood 8.3g(138,0.06mol), DMPU solvent 100ml.Mixture is heated to 175 DEG C, stirs, by TCL board monitoring reaction process, reacts and complete for 13 hours.Cooling, in impouring water, leaches, and dry, with pillar layer separation, ethyl acetate and petroleum ether mixtures drip washing, obtain target molecule 6.88g, molecular weight 487, productive rate 86.1%.
(4) the 4th steps
1000 milliliters of a bite bottles, join magnetic agitation, add above-mentioned 3rd step final product 6.88g(molecular weight 487,0.0141mol), triphenylamine-4-boric acid 4.74g(molecular weight 289,0.0164mol), Pd (PPh3) 4 usage quantity 1.50g(molecular weight 1154,0.0013mol), aqueous sodium carbonate 130ml(2M), toluene 130ml, ethanol 130ml.After argon replaces, backflow, with TLC monitoring reaction, reacts completely after 4 hours, cooling, and product solid major part is separated out, and filters, and purifies (also can purify with post separation method if desired), obtain 6.73g product, molecular weight 636, productive rate 75% with recrystallization method.
Embodiment 3
The synthesis of compound 2
Synthesis step is same as the four-step reaction in embodiment 2, just will change into iodobenzene to methiodide benzene in the 3rd step, in the 4th step, triphenylamine-4-boric acid is changed into 4-(N-phenyl-(1-naphthyl) amino) phenylo boric acid, obtain compound 2.
Embodiment 4
The synthesis of compound 3
Synthesis step is same as the four-step reaction in embodiment 2, will change as 2-iodine naphthalene to methiodide benzene in the 3rd step; 4th step, changes into N-phenyl carbazole-3-boric acid, obtains compound 3 by triphenylamine-4-boric acid.
Embodiment 5
The synthesis of compound 4
Synthesis step is same as the four-step reaction in embodiment 2, will change as 2-iodine naphthalene to methiodide benzene in the 3rd step; 4th step, changes into 6,9-phenylbenzene carbazole-3-boric acid, obtains compound 4 by triphenylamine-4-boric acid.
Embodiment 6
The synthesis of compound 5
Synthesis step is divided into four steps, and first three walks the front three-step reaction be same as in embodiment 2, will change as 2-iodine naphthalene to methiodide benzene in the 3rd step; And four-step reaction is same as the three-step reaction in embodiment 2, just 4-(carbazole-9-base will be changed into methiodide benzene) iodobenzene, obtain compound 5.
Embodiment 7
The synthesis of compound 6
Synthesis step is divided into four steps, and first three walks the front three-step reaction be same as in embodiment 2, will change as 2-iodine naphthalene to methiodide benzene in the 3rd step; And four-step reaction is same as the three-step reaction in embodiment 2, just will changes into 3-phenyl carbazole to methiodide benzene, obtain compound 6.
Embodiment 8
The synthesis of compound 7
Synthesis step is same as the four-step reaction in embodiment 2, will change as 2-iodine naphthalene to methiodide benzene in the 3rd step; 4th step, changes into 8-phenyl dibenzothiophene-2-boric acid, obtains compound 7 by triphenylamine-4-boric acid.
Embodiment 9
The synthesis of compound 8
Synthesis step is same as the four-step reaction in embodiment 2, just will change as 2-iodine naphthalene to methiodide benzene in the 3rd step; 4th step, changes into 8-phenyl diphenylene-oxide-2-boric acid, obtains compound 8 by triphenylamine-4-boric acid.
Embodiment 10
The synthesis of compound 9
Synthesis step is same as the four-step reaction in embodiment 2, just will change as 2-iodine naphthalene to methiodide benzene in the 3rd step; 4th step, changes into 10-(2-naphthyl by triphenylamine-4-boric acid) anthracene-9-boric acid, obtain compound 9.
Embodiment 11
The synthesis of compound 10
Synthesis step is same as the four-step reaction in embodiment 2, just will change as 2-iodine naphthalene to methiodide benzene in the 3rd step; 4th step, changes into pyrene-1-boric acid by triphenylamine-4-boric acid, obtains compound 10.
Embodiment 12
The synthesis of compound 11
Synthesis step is same as the four-step reaction in embodiment 2, just will change as 2-iodine naphthalene to methiodide benzene in the 3rd step; 4th step, changes into triphenylene-2-boric acid by triphenylamine-4-boric acid, obtains compound 11.
Embodiment 13
The synthesis of compound 12
Synthesis step is same as the four-step reaction in embodiment 2, just will change as 2-iodine naphthalene to methiodide benzene in the 3rd step; 4th step, changes into-6-boric acid in the wrong by triphenylamine-4-boric acid, obtains compound 12.
Embodiment 14
The synthesis of compound 13
Synthesis step is same as the four-step reaction in embodiment 2, just in the first step, 2,4-bis-bromo nitrobenzene is changed into 2,5-bis-bromo nitrobenzene; To change as 2-iodine naphthalene to methiodide benzene in the 3rd step; 4th step, changes into 4-(N-phenyl-N(1-naphthyl by triphenylamine-4-boric acid) amino) phenylo boric acid, obtain compound 13.
Embodiment 15
The synthesis of compound 14
Synthesis step is same as the four-step reaction in embodiment 2, just in the first step, 2,4-bis-bromo nitrobenzene is changed into 2,5-bis-bromo nitrobenzene; To change as 2-iodine naphthalene to methiodide benzene in the 3rd step; 4th step, changes into dibenzothiophene-4-boric acid by triphenylamine-4-boric acid, obtains compound 14.
Embodiment 16
The synthesis of compound 15
Synthesis step is same as the four-step reaction in embodiment 2, just in the first step, 2,4-bis-bromo nitrobenzene is changed into 2,5-bis-bromo nitrobenzene; To change as 2-iodine naphthalene to methiodide benzene in the 3rd step; 4th step, changes into 8-phenyl dibenzothiophene-2-boric acid, obtains compound 15 by triphenylamine-4-boric acid.
Embodiment 17
The synthesis of compound 16
Synthesis step is same as the four-step reaction in embodiment 2, just in the first step, 2,4-bis-bromo nitrobenzene is changed into 2,5-bis-bromo nitrobenzene; To change as 2-iodine naphthalene to methiodide benzene in the 3rd step; In the 4th step, triphenylamine-4-boric acid is changed into 8-phenyl diphenylene-oxide-2-boric acid, obtain compound 16.
Embodiment 18
The synthesis of compound 17
Synthesis step is same as the four-step reaction in embodiment 2, just in the first step, 2,4-bis-bromo nitrobenzene is changed into 2,5-bis-bromo nitrobenzene; To change as 2-iodine naphthalene to methiodide benzene in the 3rd step; In the 4th step, triphenylamine-4-boric acid is changed into 10-(2-naphthyl) anthracene-9-boric acid, obtain compound 17.
Embodiment 19
The synthesis of compound 18
Synthesis step is same as the four-step reaction in embodiment 2, just in the first step, 2,4-bis-bromo nitrobenzene is changed into 2,5-bis-bromo nitrobenzene; To change as 2-iodine naphthalene to methiodide benzene in the 3rd step; In the 4th step, triphenylamine-4-boric acid is changed into 4-(10-(2-naphthyl) anthracene-9-base) phenylo boric acid, obtain compound 18.
Embodiment 20
The synthesis of compound 19
Synthesis step is same as the four-step reaction in embodiment 2, just in the first step, 2,4-bis-bromo nitrobenzene is changed into 2,5-bis-bromo nitrobenzene; To change as 2-iodine naphthalene to methiodide benzene in the 3rd step; In the 4th step, triphenylamine-4-boric acid is changed into pyrene-1-boric acid, obtain compound 19.
Embodiment 21
The synthesis of compound 20
Synthesis step is same as the four-step reaction in embodiment 2, just the first step just 2,4-bis-bromo nitrobenzenes change into 2,5-bis-bromo nitrobenzene; To change as 2-iodine naphthalene to methiodide benzene in the 3rd step; In the 4th step, triphenylamine-4-boric acid is changed into 12-phenyl and bend-6-boric acid, obtain compound 20.
Embodiment 22
The synthesis of compound 21
Synthesis step is same as the four-step reaction in embodiment 2, just in the first step, 2,4-bis-bromo nitrobenzene is changed into 2,5-bis-bromo nitrobenzene; To change as 2-iodine naphthalene to methiodide benzene in the 3rd step; In the 4th step, triphenylamine-4-boric acid is changed into triphenylene-2-boric acid, obtain compound 21.
Mass spectrometric detection data and the Elemental analysis data of gained compound 1-21 refer to table 1.
Below mass spectrum and the Elemental analysis data of compound 1 to compound 21 of the present invention:
Embodiment 23
The Application Example of each compound of the present invention
Conveniently compare the performance of these hole mobile materials and fluorescent host material, the present invention devises a simple electroluminescence device, hole injection layer material we select HAT, hole mobile material NPB is as comparative material.Organic luminous layer is made up of light emitting host and dopant material, and we use traditional light emitting host material EM1 as comparative material, and EM2 is as luminescent dopant material, and wherein the structure of HAT, NPB, EM1, EM2 is respectively:
In the embodiment of the present invention, the structure of organic electroluminescence device is:
Substrate/anode/hole injection layer (HIL)/hole transmission layer (HTL)/organic luminous layer (EL)/electron transfer layer (ETL)/negative electrode.
Substrate can use the substrate in conventional organic luminescence device, such as: glass or plastics.In organic electroluminescence device of the present invention makes, select glass substrate, ITO makes anode material.
Electron injection material can use the various many arylamine very easily providing electronics, also can use many cyano group class material of extreme electron deficiency, and such molecule usually uses its lowest unoccupied molecular orbital (LUMO) to transmit electronics.The hole-injecting material used in the present invention is HAT.
Hole transmission layer can adopt various tri-arylamine group material.The material of stating in the present invention can be used as hole mobile material in electroluminescence device, compares with traditional hole mobile material NPB.
Emitting layer material has many kinds.The material of stating in the present invention can be used as light emitting host material in electroluminescence device, and luminescent dopant material is EM2.
Electron transport layer materials has many kinds.In order to characterize the material of stating in the present invention, we use common AlQ3 as electron transport material here, and object compares material property in the present invention, do not lie in the excellence pursuing device performance.
Negative electrode can adopt metal and composition thereof structure, as Mg:Ag, Ca:Ag etc., can be also electron injecting layer/metal-layer structure, as common cathode structures such as LiF/Al, Li2O/Al.Cathode material selected in organic electroluminescence device of the present invention makes is LiF/Al.
Embodiment 24
Compound in the present embodiment is as the hole mobile material in organic electroluminescence device, and prepared multiple organic electroluminescence device altogether, its structure is: ITO/HAT(5nm)/hole mobile material (40nm)/EM1:EM2 (30nm)/Alq
3(20nm)/LiF(0.5nm)/Al(150nm);
A contrast organic electroluminescence device, hole mobile material selects NPB, and all the other organic electroluminescence devices select material of the present invention.
In the present embodiment, organic electroluminescence device preparation process is as follows:
Sheet glass supersound process in commercial detergent of ITO transparency conducting layer will be coated with, rinse in deionized water, at acetone: ultrasonic oil removing in alcohol mixed solvent, be baked under clean environment and remove moisture content completely, by UV-light and ozone clean, and with low energy positively charged ion bundle bombarded surface;
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10
-5~ 9 × 10
-3pa, on above-mentioned anode tunic, vacuum evaporation HAT is as hole injection layer, and evaporation rate is 0.1nm/s, and evaporation thickness is 5nm;
Particular compound 1,3,4,6,7,8,11,13,14,15 on hole injection layer again in the present invention of evaporation one deck or NPB are as hole transmission layer, and evaporation rate is 0.1nm/s, and evaporation thickness is 40nm;
Vacuum evaporation luminescent layer EM1 and EM2(ratio 95%:5% on hole transmission layer), evaporation rate is 0.1nm/s, and evaporation total film thickness is 30nm;
On luminescent layer, vacuum evaporation one deck AlQ3 is as electron transport material respectively, and its evaporation rate is 0.1nm/s, and evaporation total film thickness is 20nm;
The upper vacuum evaporation thickness of electron transfer layer (ETL) be the LiF of 0.5nm as electron injecting layer, thickness is the negative electrode of Al layer as device of 150nm.
Organic electroluminescence device performance sees the following form:
| Compound number | Require brightness cd/m 2 | Voltage V | Current efficiency cd/A |
| NPB | 5000.00 | 6.8 | 25.1 |
[0143]
| 1 | 5000.00 | 6.3 | 27.0 |
| 3 | 5000.00 | 6.5 | 27.2 |
| 4 | 5000.00 | 6.0 | 26.8 |
| 6 | 5000.00 | 6.1 | 28.1 |
| 7 | 5000.00 | 6.4 | 28.3 |
| 8 | 5000.00 | 6.2 | 28.1 |
| 11 | 5000.00 | 6.3 | 28.0 |
| 13 | 5000.00 | 6.6 | 27.9 |
| 14 | 5000.00 | 6.3 | 27.3 |
| 15 | 5000.00 | 6.2 | 27.6 |
Embodiment 25
Compound in the present embodiment is as the hole mobile material in organic electroluminescence device, prepare multiple organic electroluminescence device altogether, its structure is: ITO/HAT(40nm)/NPB(40nm)/light emitting host material: EM2 (85%:15%, 30nm)/Alq3(20nm)/LiF(0.5nm)/Al(150nm);
A contrast organic electroluminescence device, light emitting host material selection EM1, all the other organic electroluminescence devices select material of the present invention.
In the present embodiment, organic electroluminescence device preparation process is as follows:
Sheet glass supersound process in commercial detergent of ITO transparency conducting layer will be coated with, rinse in deionized water, at acetone: ultrasonic oil removing in alcohol mixed solvent, be baked under clean environment and remove moisture content completely, by UV-light and ozone clean, and with low energy positively charged ion bundle bombarded surface;
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10
-5~ 9 × 10
-3pa, on above-mentioned anode tunic, vacuum evaporation HAT is as hole injection layer, and evaporation rate is 0.1nm/s, and evaporation thickness is 40nm;
On hole injection layer, evaporation one deck NPB is as hole transmission layer again, and evaporation rate is 0.1nm/s, and evaporation thickness is 40nm;
Compound 1,9,11,12,17,18,19,20 on hole transmission layer in the present invention of vacuum evaporation luminescent layer or EM1, doping evaporation EM2(ratio 85%:15%), evaporation rate is 0.1nm/s, and evaporation total film thickness is 30nm;
On luminescent layer, vacuum evaporation one deck AlQ3 is as electron transport material respectively, and its evaporation rate is 0.1nm/s, and evaporation total film thickness is 20nm;
The upper vacuum evaporation thickness of electron transfer layer (ETL) be the LiF of 0.5nm as electron injecting layer, thickness is the negative electrode of Al layer as device of 150nm.
Luminescent device performance sees the following form:
| Compound number | Require brightness cd/m2 | Voltage V | Current efficiency cd/A |
| EM1 | 5000.00 | 6.8 | 25.1 |
| 1 | 5000.00 | 6.3 | 26.9 |
| 9 | 5000.00 | 6.4 | 27.3 |
| 11 | 5000.00 | 6.3 | 27.7 |
| 12 | 5000.00 | 6.6 | 26.7 |
| 17 | 5000.00 | 6.2 | 28.1 |
| 18 | 5000.00 | 6.1 | 28.3 |
| 19 | 5000.00 | 6.5 | 28.5 |
| 20 | 5000.00 | 6.0 | 28.0 |
Above result shows, novel organic luminescent material of the present invention is used for organic electroluminescence device, can effectively reduce landing voltage, and improving current efficiency, is hole mobile material of good performance and light emitting host material.
Although describe the present invention in conjunction with the embodiments, the present invention is not limited to above-described embodiment, should be appreciated that, under the guiding of the present invention's design, those skilled in the art can carry out various amendment and improvement, and claims summarise scope of the present invention.
Claims (9)
1. a luminous organic material, is characterized in that, has structure as shown in the formula (I):
Wherein:
Independently be selected from H, the substituted or unsubstituted aromatic hydrocarbon group of C6-C30, the substituted or unsubstituted condensed-nuclei aromatics group of C6-C30, the substituted or unsubstituted fused heterocycle group of C6-C30, or five yuan, hexa-atomic heterocycle or substituted heterocycle, the substituted or unsubstituted triaryl amine group of C6-C30, or aryl oxide group, one in the substituted or unsubstituted aliphatic alkyl group of C1-C12, Ar
1-Ar
8be asynchronously H.
2. luminous organic material according to claim 1, is characterized in that, described Ar
5, Ar
6, Ar
7, Ar
8, Ar
9be H simultaneously.
3. luminous organic material according to claim 1, is characterized in that, described Ar
4be selected from phenyl, substituted-phenyl, xenyl, naphthyl, anthryl, phenanthryl, perylene base, pyrenyl.
4. luminous organic material according to claim 1, is characterized in that, described Ar
1, Ar
2, Ar
3separately be selected from phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, Qu Ji, benzo phenanthryl, substituted-phenyl, substituted naphthyl, replacement pyrenyl, replace and bend base, replace anthryl, carbazyl, triphenylenyl, substituted carbazole base, dibenzothiophene base, substituted diphenylamine thiophthene base, dibenzofuran group, substituted diphenylamine furyl, triarylamine, replacement triarylamine.
5. the luminous organic material according to any one of claim 1-4, is characterized in that, described compound is selected from following structural formula:
6. the luminous organic material according to any one of claim 1-5, is applied in organic electroluminescence.
7. luminous organic material according to claim 6, is characterized in that, described luminous organic material can be used as hole-injecting material, hole mobile material or material of main part.
8. an organic electroluminescence device, comprises substrate, and forms anode layer, organic luminescence function layer and cathode layer on the substrate successively;
Described organic luminescence function layer comprises hole transmission layer, organic luminous layer and electron transfer layer, it is characterized in that:
The substrate material of described hole transmission layer contains the luminous organic material according to any one of claim 1-5.
9. an organic electroluminescence device, comprises substrate, and forms anode layer, organic luminescence function layer and cathode layer on the substrate successively;
Described organic luminescence function layer comprises hole transmission layer, organic luminous layer and electron transfer layer, it is characterized in that:
The substrate material of described organic luminous layer contains the luminous organic material according to any one of claim 1-5.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108084124A (en) * | 2017-11-02 | 2018-05-29 | 中节能万润股份有限公司 | A kind of class new Organic Electro Luminescent Materials in the wrong and preparation method thereof |
| CN111662704A (en) * | 2019-11-18 | 2020-09-15 | 北京理工大学 | Preparation method of novel organic phosphorescent material and application of novel organic phosphorescent material in ink-jet printing ink and writing ink |
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|---|---|---|---|---|
| WO2010114264A2 (en) * | 2009-03-31 | 2010-10-07 | Dow Advanced Display Materials,Ltd. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| US20120097929A1 (en) * | 2010-10-25 | 2012-04-26 | Samsung Mobile Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
| KR20120081539A (en) * | 2011-01-11 | 2012-07-19 | (주)씨에스엘쏠라 | Organic light compound and organic light device using the same |
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| WO2010114264A2 (en) * | 2009-03-31 | 2010-10-07 | Dow Advanced Display Materials,Ltd. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| US20120097929A1 (en) * | 2010-10-25 | 2012-04-26 | Samsung Mobile Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
| KR20120081539A (en) * | 2011-01-11 | 2012-07-19 | (주)씨에스엘쏠라 | Organic light compound and organic light device using the same |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108084124A (en) * | 2017-11-02 | 2018-05-29 | 中节能万润股份有限公司 | A kind of class new Organic Electro Luminescent Materials in the wrong and preparation method thereof |
| CN111662704A (en) * | 2019-11-18 | 2020-09-15 | 北京理工大学 | Preparation method of novel organic phosphorescent material and application of novel organic phosphorescent material in ink-jet printing ink and writing ink |
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