CN104513246A - Anthra bicarbazole derivative and applications thereof - Google Patents
Anthra bicarbazole derivative and applications thereof Download PDFInfo
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- CN104513246A CN104513246A CN201310459869.8A CN201310459869A CN104513246A CN 104513246 A CN104513246 A CN 104513246A CN 201310459869 A CN201310459869 A CN 201310459869A CN 104513246 A CN104513246 A CN 104513246A
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- Prior art keywords
- benzo
- carbazole
- substituted
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- organic
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- 239000000463 material Substances 0.000 claims abstract description 75
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
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- 238000005401 electroluminescence Methods 0.000 claims description 34
- 239000000758 substrate Substances 0.000 claims description 20
- 230000005540 biological transmission Effects 0.000 claims description 15
- 150000001716 carbazoles Chemical class 0.000 claims description 14
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 8
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- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 8
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- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 5
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- 125000001725 pyrenyl group Chemical group 0.000 claims description 5
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- QZPFOTHQLGQYCL-UHFFFAOYSA-N c(cc1)ccc1-[n]1c2cc(-c3cccc4c3c-3cc5c4c4ccccc4[n]5-c4ccccc4)c4c-3cccc4c2c2c1cccc2 Chemical compound c(cc1)ccc1-[n]1c2cc(-c3cccc4c3c-3cc5c4c4ccccc4[n]5-c4ccccc4)c4c-3cccc4c2c2c1cccc2 QZPFOTHQLGQYCL-UHFFFAOYSA-N 0.000 description 1
- FPCIBOSWYAYHKZ-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)cc(c(c2c3)c(cccc4-5)c4c3-c3c4c-5cc([n](c(c5c6)ccc6-c6ccccc6)-c6ccccc6)c5c4ccc3)c1[n]2-c1ccccc1 Chemical compound c(cc1)ccc1-c(cc1)cc(c(c2c3)c(cccc4-5)c4c3-c3c4c-5cc([n](c(c5c6)ccc6-c6ccccc6)-c6ccccc6)c5c4ccc3)c1[n]2-c1ccccc1 FPCIBOSWYAYHKZ-UHFFFAOYSA-N 0.000 description 1
- WFPLCKFJZYFAKL-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)cc(c(c2c3)c(cccc4-5)c4c3-c3cccc4c3c-5cc3c4c4cc(-c5ccccc5)ccc4[n]3-c3cc4ccccc4cc3)c1[n]2-c1cc(cccc2)c2cc1 Chemical compound c(cc1)ccc1-c(cc1)cc(c(c2c3)c(cccc4-5)c4c3-c3cccc4c3c-5cc3c4c4cc(-c5ccccc5)ccc4[n]3-c3cc4ccccc4cc3)c1[n]2-c1cc(cccc2)c2cc1 WFPLCKFJZYFAKL-UHFFFAOYSA-N 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 230000009191 jumping Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002979 perylenes Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 230000004304 visual acuity Effects 0.000 description 1
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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Abstract
The present invention relates to a class of benzo[c]benzo[3,4]carbazole carbazole derivatives represented by a formula (I), wherein Ar1-Ar8 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 compound, 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: WO2010/114017A1, publication date 2010,10,7).
summary of the invention
The object of the present invention is to provide a class novel cpd, i.e. the two carbazole derivative of anthra, this compounds may be used for ORGANIC ELECTROLUMINESCENCE DISPLAYS field.
For this reason, the technical scheme that the present invention takes is:
The two carbazole derivative of a kind of anthra, has structure as shown in the formula (I):
Wherein:
Ar
1-Ar
12independently be selected from the substituted or non-substituted aromatic hydrocarbon group of H, C6 ~ C30, the condensed-nuclei aromatics group of the substituted or non-substituted of C6 ~ C30, the substituted or non-substituted of C6 ~ C30 fused heterocycle group, five yuan, hexa-atomic heterocycle or substituted heterocycle, triarylamine group, aryl oxide group base group, C1 ~ C12 substituted or non-substituted aliphatic alkyl group in one.
Described condensed-nuclei aromatics group is naphthyl, substituted naphthyl, anthryl, replacement anthryl, phenanthryl, replacement phenanthryl, benzo naphthyl, replacement benzo naphthyl, benzo phenanthryl, replacement benzo phenanthryl, pyrenyl, replacement pyrenyl, Qu Ji, triphenylenyl, benzo phenanthryl.
Described fused heterocycle group is carbazyl, substituted carbazole base, dibenzo thiophene base, substituted diphenylamine thienyl, dibenzofuran group, substituted diphenylamine furyl.
Described Ar
6and Ar
12independently be selected from phenyl, substituted-phenyl, naphthyl, substituted naphthyl, xenyl, carbazyl, substituted carbazole base, dibenzo thiophene base, substituted diphenylamine thienyl, dibenzofuran group, substituted diphenylamine one in furyl.
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 the two carbazole derivative of a kind of described anthra, be applied 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, it is characterized in that:
The substrate material of described hole transmission layer contains the two carbazole derivative of described anthra.
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, it is characterized in that:
The substrate material of described organic luminous layer contains the two carbazole derivative of described anthra.
For convenience of description, in the application's subsequent content, " 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:
(1) in the present invention, we have proposed the two this novel material of carbazole derivative of anthra, the two carbazole derivative of anthra is not only fitted collaborative agent material but also is made hole mobile material, and in red device as hole mobile material application better, the use of material of the present invention, what reduce device opens bright voltage, 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 7 in the embodiment of the present invention 8, and HOMO energy level is-4.792ev, triplet T1=1.5176ev;
Fig. 2 is the lowest unoccupied molecular orbital of compound 7 in the embodiment of the present invention 8, and lumo energy is-1.903ev;
Fig. 3 be in the embodiment of the present invention 8 compound 7 through Gaussian03B3LYP/6-31G(d) method optimize after each atom and the three-dimensional distribution map of group;
Fig. 4 is the highest occupied molecular orbital(HOMO) of the embodiment of the present invention 9 compound 8, and HOMO energy level is-4.790ev, triplet T1=1.5198ev;
Fig. 5 is the lowest unoccupied molecular orbital of the embodiment of the present invention 9 compound 8, and lumo energy is-1.902ev.
Embodiment
Basic raw material used in the present invention, 3-Xiu perylene, 3,9-bis-Xiu perylene, 2-bromo nitrobenzene, 2,4-bis-bromo nitrobenzene, 2,5-bis-bromo nitrobenzene, and bromo carbazole derivative, bromo diphenylene-oxide, bromo dibenzothiophene, bromo Chrysene, bromo triphenylene, bromo pyrene etc., can buy in each large industrial chemicals market at home.This laboratory oneself synthesis of 5-bromine benzophenanthrene system.
Embodiment 1
The preparation embodiment of intermediate of the present invention:
The diborated synthesis of main Zhong Jian Ti perylene-3,9-,
Be dissolved in the THF of 100ml drying by 3, the 9-bis-Xiu perylenes (molecular weight 410,0.02mol) of 8.2g ,-80 DEG C drip normal-butyl reason 20ml(2.5M, 0.05mol), stir 15min, then drip triisopropyl boric acid ester 40ml.Hydrolysis, regulate pH to separate out white boric acid derivatives 6.8g 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, Jia Ru perylene-3-boric acid 6.8g(molecular weight 340,0.02mol), 2,4-bis-bromo nitrobenzene 11.12g(molecular weight 278,0.04mol), Pd (PPh3) 4 usage quantity 2.5g(molecular weight 1154,0.002166mol), 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 11.6g product, molecular weight 652, productive rate 89%.
(2) second step
150 milliliters of a bite bottles, join magnetic agitation, add the final product 11.6g(molecular weight 652,0.0178mol of the first step), triphenylphosphine 21g(molecular weight 262,0.08mol), orthodichlorobenzene 100ml.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 9.01g, molecular weight 588, productive rate 86%.
(3) the 3rd steps
150 milliliters of a bite bottles, join magnetic agitation, add second step final product 9.01g(molecular weight 588,0.0153mol), 2-naphthalene iodide 8.2g(molecular weight 204,0.04mol), cuprous iodide 0.8g(molecular weight 190,0.0042mol), salt of wormwood 14.0g(138,0.10mol), DMPU solvent 120ml.Mixture is heated to 175 DEG C, stirs, by TCL board monitoring reaction process, reacts and complete for 10 hours.Cooling, in impouring water, leaches, and dry, with pillar layer separation, ethyl acetate and petroleum ether mixtures drip washing, obtain target molecule 9.97g, molecular weight 740, productive rate 88%
(4) the 4th steps
1000 milliliters of a bite bottles, join magnetic agitation, add above-mentioned 3rd step final product 9.97g(molecular weight 740,0.0135mol), phenylo boric acid 3.7g(molecular weight 122,0.03mol), Pd (PPh3) 4 usage quantity 2.5g(molecular weight 1154,0.00217mol), sodium carbonate 140ml(2M), toluene 140ml, ethanol 140ml.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 8.82g product, molecular weight 734, productive rate 89% with recrystallization method.
Embodiment 3
The synthesis of compound 2
Synthesis step is same as the four-step reaction in embodiment 2, and just change into iodobenzene to methiodide benzene in the 3rd step, obtain compound 2, its concrete structure formula is as follows:
Embodiment 4
The synthesis of compound 3
Synthesis step is same as the front three-step reaction in embodiment 2, just in a first step 2,4-bis-bromo nitrobenzene is changed into 2-bromo nitrobenzene; In the 3rd step, iodobenzene is changed into 2-iodine naphthalene, obtain compound 3, its concrete structure formula is as follows:
Embodiment 5
The synthesis of compound 4
Synthesis step is same as the front three-step reaction in embodiment 2, just in a first step 2,4-bis-bromo nitrobenzene is changed into 2-bromo nitrobenzene; In the 3rd step, iodobenzene is changed into 1-iodine naphthalene, obtain compound 4, its concrete structure formula is as follows:
Embodiment 6
The synthesis of compound 5
Synthesis step is same as the front three-step reaction in embodiment 2, and just in a first step 2,4-bis-bromo nitrobenzene is changed into 2-bromo nitrobenzene, obtain compound 5, its concrete structure formula is as follows:
Embodiment 7
The synthesis of compound 6
Synthesis step is same as the front three-step reaction in embodiment 2, just in a first step 2,4-bis-bromo nitrobenzene is changed into 2-bromo nitrobenzene; Change into iodobenzene to methiodide benzene in the 3rd step, obtain compound 6, its concrete structure formula is as follows:
Embodiment 8
The synthesis of compound 7
Synthesis step is same as the four-step reaction in embodiment 2, and just in the 4th step, phenylo boric acid is changed into toluene boric acid, obtains compound 7, and its concrete structure formula is as follows:
Embodiment 9
The synthesis of compound 8
Synthesis step is same as the four-step reaction in embodiment 2, and just change into methiodide benzene in the 3rd step by iodobenzene, in the 4th step, phenylo boric acid is changed into toluene boric acid, obtains compound 8, and its concrete structure formula is as follows:
Embodiment 10
The synthesis of compound 9
Synthesis step is same as the four-step reaction in embodiment 2, and just in a first step 2,4-bis-bromo nitrobenzene is changed into 2,5-bis-bromo nitrobenzene, obtain compound 9, its concrete structure formula is as follows:
Embodiment 11
The synthesis of compound 10
Synthesis step is same as the four-step reaction in embodiment 2, and just in a first step 2,4-bis-bromo nitrobenzene is changed into 2,5-bis-bromo nitrobenzene, change into iodobenzene to methiodide benzene in the 3rd step, obtain compound 10, its concrete structure formula is as follows:
Embodiment 12
The synthesis of compound 11
Synthesis step is same as the four-step reaction in embodiment 2, and just in a first step 2,4-bis-bromo nitrobenzene is changed into 2,5-bis-bromo nitrobenzene, change into phenylo boric acid to toluene boric acid in the 4th step, obtain compound 11, its concrete structure formula is as follows:
Embodiment 13
The synthesis of compound 12
Synthesis step is same as the four-step reaction in embodiment 2, just in a first step 2,4-bis-bromo nitrobenzene is changed into 2,5-bis-bromo nitrobenzene, changes into methiodide benzene in the 3rd step by iodobenzene, changes into toluene boric acid in the 4th step by phenylo boric acid, obtain compound 12, its concrete structure formula is as follows:
Embodiment 14
The synthesis of compound 13
Synthesis step is same as the front three-step reaction in embodiment 2, and just in a first step 2,4-bis-bromo nitrobenzene is changed into 2-bromo nitrobenzene, in the 3rd step, iodobenzene is changed into 4-iodine biphenyl, obtain compound 13, its concrete structure formula is as follows:
Embodiment 15
The synthesis of compound 14
Synthesis step is same as the four-step reaction in embodiment 2, in the 3rd step, iodobenzene is changed into 2-iodine naphthalene, obtains compound 14, and its concrete structure formula is as follows:
Embodiment 16
The synthesis of compound 15
Synthesis step is same as the four-step reaction in embodiment 2, and just in a first step 2,4-bis-bromo nitrobenzene is changed into 2,5-bis-bromo nitrobenzene, in the 3rd step, iodobenzene is changed into 2-iodine naphthalene, obtain compound 15, its concrete structure formula is as follows:
Embodiment 17
The synthesis of compound 16
Synthesis step is same as the front three-step reaction in embodiment 2, and just in a first step 2,4-bis-bromo nitrobenzene is changed into 2-bromo nitrobenzene, in the 3rd step, iodobenzene is changed into 2-iodine diphenylene-oxide, obtain compound 16, its concrete structure formula is as follows:
Embodiment 18
The synthesis of compound 17
Synthesis step is same as the front three-step reaction in embodiment 2, and just in a first step 2,4-bis-bromo nitrobenzene is changed into 2-bromo nitrobenzene, in the 3rd step, iodobenzene is changed into 2-iodine dibenzothiophene, obtain compound 17, its concrete structure formula is as follows:
Mass spectrometric detection data and the Elemental analysis data of gained compound 1-17 refer to table 1.
Below mass spectrum and the Elemental analysis data of compound 1 to compound 17 of the present invention:
Embodiment 19
The Application Example of each compound of the present invention
Conveniently compare the performance that these materials are used as hole mobile material 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 hole injecting 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 20
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;
Compound 1,4,6,8,9,16,17 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 is fast
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/m2 | Voltage V | Current efficiency cd/A |
| NPB | 5000.00 | 6.8 | 25.1 |
[0149]
| 1 | 5000.00 | 6.5 | 26.8 |
| 4 | 5000.00 | 6.1 | 27.3 |
| 6 | 5000.00 | 6.4 | 27.5 |
| 8 | 5000.00 | 6.2 | 27.0 |
| 9 | 5000.00 | 6.3 | 26.7 |
| 16 | 5000.00 | 6.4 | 28.2 |
| 17 | 5000.00 | 6.2 | 26.9 |
Embodiment 21
Compound in the present embodiment is as the fluorescent host material in organic electroluminescence device, prepare multiple organic electroluminescence device altogether, its structure is: ITO/HAT(5nm)/NPB(40nm)/light emitting host material: EM2 (95%:5%, 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 5nm;
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 2,3,7,10,12,14,14 on hole transmission layer in the present invention of vacuum evaporation luminescent layer or EM1, doping evaporation EM2(ratio 95%:5%), 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 |
| 2 | 5000.00 | 6.0 | 26.9 |
| 3 | 5000.00 | 6.1 | 27.3 |
| 7 | 5000.00 | 6.5 | 27.5 |
| 10 | 5000.00 | 6.3 | 27.3 |
| 12 | 5000.00 | 6.5 | 27.9 |
| 14 | 5000.00 | 6.2 | 28.0 |
| 15 | 5000.00 | 6.2 | 27.4 |
Above result shows, new organic materials 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. benzo ［ c ］ benzo ［ 3, a 4 ］ carbazole carbazole derivative, is characterized in that having structure as shown in the formula (I):
Wherein:
Ar1-Ar8 is independently selected from the substituted or unsubstituted aromatic hydrocarbon group of H, 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, the one in the substituted or unsubstituted aliphatic alkyl group of C1-C12, Ar
1-Ar
8be asynchronously H.
2. benzo according to claim 1 ［ c ］ benzo ［ 3,4 ］ carbazole carbazole derivative, is characterized in that, described Ar
1, Ar
5be H simultaneously.
3. benzo according to claim 1 ［ c ］ benzo ［ 3,4 ］ carbazole carbazole derivative, is characterized in that, described Ar
2, Ar
3, Ar
6, Ar
7separately be selected from phenyl, naphthyl, anthryl, phenanthryl, perylene base, pyrenyl, Qu Ji, benzo phenanthryl, substituted-phenyl, substituted naphthyl, replacement pyrenyl, replace and bend base, replacement anthryl, carbazyl, dibenzothiophene base, dibenzofuran group, triarylamine.
4. benzo according to claim 1 ［ c ］ benzo ［ 3,4 ］ carbazole carbazole derivative, is characterized in that, described Ar
4, Ar
8independently be selected from phenyl, substituted-phenyl, xenyl, naphthyl, anthryl, phenanthryl, perylene base, dibenzanthracene, pyrenyl, hexichol ether.
5. benzo ［ c ］ benzo ［ 3, the 4 ］ carbazole according to any one of claim 1-4 carbazole derivative, it is characterized in that, described compound is selected from following structural formula:
6. benzo ［ c ］ benzo ［ 3, the 4 ］ carbazole described in an any one of 1-5 carbazole derivative, be applied in organic electroluminescence device.
7. benzo according to claim 6 ［ c ］ benzo ［ 3,4 ］ carbazole carbazole derivative, is characterized in that, described benzo ［ c ］ benzo ［ 3,4 ］ carbazole carbazole derivative 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 benzo ［ c ］ benzo ［ 3,4 ］ carbazole according to any one of claim 1-5 and carbazole derivative.
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 benzo ［ c ］ benzo ［ 3,4 ］ carbazole according to any one of claim 1-5 and carbazole derivative.
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| CN106433614A (en) * | 2015-08-04 | 2017-02-22 | 北京鼎材科技有限公司 | Organic electroluminescent compound, use thereof and organic electroluminescent device |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011081429A2 (en) * | 2009-12-30 | 2011-07-07 | 주식회사 두산 | Organic compound, and organic electroluminescent device using 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 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101430589B1 (en) * | 2011-02-21 | 2014-08-19 | (주)씨에스엘쏠라 | Organic light compound and organic light device using the same |
-
2013
- 2013-09-30 CN CN201310459869.8A patent/CN104513246A/en active Pending
- 2013-09-30 CN CN201710757112.5A patent/CN107722015A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011081429A2 (en) * | 2009-12-30 | 2011-07-07 | 주식회사 두산 | Organic compound, and organic electroluminescent device using 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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