CN104725298A - Carbazole compounds, synthesis and application thereof in OLEDs (organic light emitting diodes) - Google Patents
Carbazole compounds, synthesis and application thereof in OLEDs (organic light emitting diodes) Download PDFInfo
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- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 19
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 18
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title claims abstract description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims abstract description 47
- 239000000463 material Substances 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 12
- -1 carbazole compound Chemical class 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 230000005540 biological transmission Effects 0.000 claims abstract description 10
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 229910000510 noble metal Inorganic materials 0.000 claims abstract description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 32
- 238000004440 column chromatography Methods 0.000 claims description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- 235000015320 potassium carbonate Nutrition 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000002347 injection Methods 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 3
- GDHXJNRAJRCGMX-UHFFFAOYSA-N 2-fluorobenzonitrile Chemical compound FC1=CC=CC=C1C#N GDHXJNRAJRCGMX-UHFFFAOYSA-N 0.000 claims description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims description 2
- YERGTYJYQCLVDM-UHFFFAOYSA-N iridium(3+);2-(4-methylphenyl)pyridine Chemical compound [Ir+3].C1=CC(C)=CC=C1C1=CC=CC=N1.C1=CC(C)=CC=C1C1=CC=CC=N1.C1=CC(C)=CC=C1C1=CC=CC=N1 YERGTYJYQCLVDM-UHFFFAOYSA-N 0.000 claims description 2
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 239000012312 sodium hydride Substances 0.000 claims description 2
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims 4
- 239000002019 doping agent Substances 0.000 claims 2
- DWFDQVMFSLLMPE-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanone Chemical compound FC1=CC=CC=C1C(=O)C1=CC=CC=C1 DWFDQVMFSLLMPE-UHFFFAOYSA-N 0.000 claims 1
- 230000005525 hole transport Effects 0.000 claims 1
- 238000010030 laminating Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 abstract 3
- 150000001716 carbazoles Chemical class 0.000 abstract 2
- 230000002194 synthesizing effect Effects 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 30
- 238000010992 reflux Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000000967 suction filtration Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 238000005401 electroluminescence Methods 0.000 description 5
- KTPHYLJFAZNALV-UHFFFAOYSA-N 2,3,4-trifluorobenzonitrile Chemical compound FC1=CC=C(C#N)C(F)=C1F KTPHYLJFAZNALV-UHFFFAOYSA-N 0.000 description 2
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 2
- 229920000144 PEDOT:PSS Polymers 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- LKFIWRPOVFNPKR-UHFFFAOYSA-N (2-fluorophenyl)-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CC=C1F LKFIWRPOVFNPKR-UHFFFAOYSA-N 0.000 description 1
- DLKNOGQOOZFICZ-UHFFFAOYSA-N 2,4,5-trifluorobenzonitrile Chemical compound FC1=CC(F)=C(C#N)C=C1F DLKNOGQOOZFICZ-UHFFFAOYSA-N 0.000 description 1
- HTKFGTCCOJIUIK-UHFFFAOYSA-N 2,4,6-trifluorobenzonitrile Chemical compound FC1=CC(F)=C(C#N)C(F)=C1 HTKFGTCCOJIUIK-UHFFFAOYSA-N 0.000 description 1
- LJFDXXUKKMEQKE-UHFFFAOYSA-N 2,4-difluorobenzonitrile Chemical compound FC1=CC=C(C#N)C(F)=C1 LJFDXXUKKMEQKE-UHFFFAOYSA-N 0.000 description 1
- LSQARZALBDFYQZ-UHFFFAOYSA-N 4,4'-difluorobenzophenone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 LSQARZALBDFYQZ-UHFFFAOYSA-N 0.000 description 1
- 108091006149 Electron carriers Proteins 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Indole Compounds (AREA)
Abstract
Carbazole compounds, synthesis and application thereof in OLEDs (organic electroluminescent devices), a method for synthesizing carbazole compounds by a one-step method, which has the advantages of cheap and easily-obtained raw materials, no need of adding a noble metal catalyst, simple and convenient operation, mild reaction conditions, low production cost, high yield and convenience for commercialization, is developed, and relates to the field of organic electroluminescent materials, in particular to a method for synthesizing a material with bipolar carrier transmission performance by a one-step method and an organic electroluminescent device prepared by the carbazole compound serving as an electrophosphorescent main body. The material with bipolar carrier transmission performance contains a carbazole unit with hole transmission performance and a benzonitrile or benzophenone unit with electron transmission performance, namely n-CzCN and n-CzCO compounds.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, be specifically related to a class carbazole compound, synthesis and the application in OLEDs thereof.
Technical background
The advantages such as organic electroluminescence device (OLEDs) is a kind of selfluminous element, has voltage low, and visual angle is wide, fast response time, thermal adaptability are good are the technique of display of a new generation.The principle of organic electroluminescence device, under electric field action, hole and electronics inject, respectively by hole injection layer, hole transmission layer and electron injecting layer, electron transfer layer from anode and negative electrode respectively, be compounded to form exciton at luminescent layer, exciton attenuation is luminous.
Improving one of organic electroluminescence device efficiency and the key in life-span is hole carrier and electron carrier density balance in device luminescent layer.Because the mobility of most of hole mobile material is far away higher than electron transport material, so the scarcity of electronic material is the important factor of restriction electroluminescent device development at present, also particularly important to this research.In order to obtain high-level efficiency and long-life device, electron transport layer materials must meet following requirement: good electron injection, good hole barrier, higher electronic mobility, high triplet.
Material containing carbazole has good cavity transmission ability usually, in OLEDs research, be widely used as overall material.Two carbazole material CBP is the material of main part used the earliest in OLED, and its triplet is 2.6eV, may be used for the doping of green glow and ruddiness phosphor material.Cyano group [K.Masui, H.Nakanotani, C.Adachi.Organic Electronics, 2013, 14, 2721-2726.Y.J.Cho, K.S.Yook, J.Y.Lee, Adv.Mater.2014, 26, 4050-4055.] and carbonyl [S.Y.Lee, T.Yasuda, Y.S.Yang, Q.Zhang, and C.Adachi, Angew.Chem.Int.Ed.2014, 53, 6402-6406] unit has good electron transport ability, by the cyanophenyl containing cyano group and carbonyl, benzophenone unit is connected in the mode of C-N key with carbazole, obtain a series of material of main part with bipolar transmission performance.But traditional C-N connects the severe reaction conditions needed, need expensive noble metal catalyst, the cost of the reaction of increase.
Summary of the invention
A kind of method synthesis that is efficient, cheap, the one-step synthesis with huge commercial value is the object of the present invention is to provide to have the material of bipolar transmission performance and adopt this material as the high performance electrophosphorescenoleds device of luminescent layer material of main part, this materials application, in electro phosphorescent device, can obtain efficient electroluminescent properties.
Carbazole compound synthesis of the present invention, comprise the steps: carbazole, fluoro benzonitrile or fluorobenzene ketone compound, alkali, add in organic solvent, back flow reaction 5-12h under nitrogen atmosphere, then ethyl alcohol recrystallization or column chromatography for separation purify after obtain described compound.
Described organic solvent is the one in methyl-sulphoxide or DMF.
Described alkali is described alkali is salt of wormwood, cesium carbonate, sodium hydroxide, potassium hydroxide, potassium tert.-butoxide, in sodium tert-butoxide or sodium hydride any one.
Described carbazole and the mol ratio of trifluorobenzonitrile are 3.3: 1, and the mol ratio of carbazole and difluorobenzonilyile and this benzophenone of difluoro thereof is 2.2: 1.Above-mentioned carbazole compound is as the material of main part of the luminescent layer of organic electroluminescence device.
Compared with prior art, the compound containing carbazole and cyanophenyl and benzophenone unit of the present invention, is connected cyanophenyl or benzophenone unit unit in the mode of C-N with carbazole unit, and traditional method formation carbonnitrogen bond all needs to add expensive noble metal catalyst.Be applied in organic electroluminescence device using this type of carbazole compound as the material of main part of luminescent layer, its device performance has greatly improved space.
Accompanying drawing explanation
Fig. 1 is carbazole compound synthetic route and structural formula of compound for this reason.
Embodiment
In order to understand the present invention better, illustrate technical scheme of the present invention below by specific embodiment.
Embodiment (1): the synthesis of 2,3-CzCN
2,3-difluorobenzonilyile (0.36g, 2.6mmol), salt of wormwood (2.23g, 16.1mmol), carbazole (0.95g, 5.7mmol), DMSO 8ml, 150 DEG C of reflux 12h.Be cooled to room temperature to pour in 200ml water and separate out a large amount of solid and stir 0.5h, suction filtration obtains white solid, and column chromatography is purified to obtain white solid, yield 95%.
1H NMR(300MHz，CDCl
3)：δppm 8.06(d，2H，J＝7.5Hz)，7.84(t，1H，J＝7.8Hz)，7.74(d，4H，J＝7.2)，7.07-7.01(m，12H)。
Embodiment (2): the synthesis of 2,4-CzCN
2,4 difluorobenzene nitrile (0.36g, 2.6mmol), salt of wormwood (2.23g, 16.1mmol), carbazole (0.95g, 5.7mmol), DMSO 8ml, 150 DEG C of reflux 12h.Be cooled to room temperature to pour in 200ml water and separate out a large amount of solid and stir 0.5h, suction filtration obtains white solid, and column chromatography is purified to obtain white solid, yield 84%.
1H NMR(300MHz，CDCl
3)：δppm 8.19-8.13(m，5H)，7.92(d，2H，J＝5.4Hz)，7.57(d，2H，J＝5.1Hz)，7.50-7.44(m，4H)，7.38-7.33(m，6H)。
Embodiment (3): the synthesis of 2,5-CzCN
2,5-difluorobenzonilyile (0.36g, 2.6mmol), salt of wormwood (2.23g, 16.1mmol), carbazole (0.95g, 5.7mmol), DMSO 8ml, 150 DEG C of reflux 12h.Be cooled to room temperature to pour in 200ml water and separate out a large amount of solid and stir 0.5h, suction filtration obtains white solid, and column chromatography is purified to obtain white solid, yield 92%;
1h NMR (300MHz, CDCl
3): δ ppm 8.20 (t, 5H, J=5.7Hz), 8.10-8.06 (m, 1H), 7.87 (d, 1H, J=8.7Hz), 7.58-7.36 (m, 12H).
Embodiment (4): the synthesis of 2,6-CzCN
2,6-difluorobenzonilyile (0.36g, 2.6mmol), salt of wormwood (2.23g, 16.1mmol), carbazole (0.95g, 5.7mmol), DMSO 8ml, 150 DEG C of reflux 12h.Be cooled to room temperature to pour in 200ml water and separate out a large amount of solid and stir 0.5h, suction filtration obtains white solid, and column chromatography is purified to obtain white solid, yield 85%;
1h NMR (300MHz, CDCl
3): δ ppm 8.17 (d, 4H, J=4.5Hz), 8.02 (t, 1H, J=4.8Hz), 7.78 (d, 2H, J=4.8Hz), 7.50 (t, 4H, J=4.5Hz), 7.38-7.36 (m, 8H).
Embodiment (5): the synthesis of 2,3,4-CzCN
2,3,4-trifluorobenzonitrile (0.28g, 2.2mmol), salt of wormwood (3g, 21.7mmol), carbazole (0.95g, 5.7mmol), DMSO 10ml, 150 DEG C of reflux 12h.Be cooled to room temperature to pour in 200ml water and separate out a large amount of solid and stir 0.5h, suction filtration obtains white solid, and column chromatography is purified to obtain white solid, yield 84%;
1h NMR (300MHz, CDCl
3): δ ppm 8.24 (d, 1H, J=8.1Hz), 8.10 (d, 1H, J=8.4Hz), (7.78-7.70 m, 4H), 7.33-7.20 (m, 4H), 7.07-6.98 (m, 10H), 6.81-6.73 (m, 4H), (6.59 t, 2H, J=7.5Hz).
Embodiment (6): the synthesis of 2,4,5-CzCN
2,4,5-trifluorobenzonitrile (0.28g, 2.2mmol), salt of wormwood (3g, 21.7mmol), carbazole (0.95g, 5.7mmol), DMSO 10ml, 150 DEG C of reflux 12h.Be cooled to room temperature to pour in 200ml water and separate out a large amount of solid and stir 0.5h, suction filtration obtains white solid, and column chromatography is purified to obtain white solid, yield 92%;
1h NMR (300MHz, CDCl
3): δ ppm 8.44 (s, 1H), 8.18 (t, 3H, J=9.6Hz), 7.87-7.77 (m, 4H), 7.54-7.39 (m, 6H), 7.23-7.06 (m, 12H).
Embodiment (7): the synthesis of 2,4,6-CzCN
2,4,6-trifluorobenzonitrile (0.28g, 2.2mmol), salt of wormwood (3g, 21.7mmol), carbazole (0.95g, 5.7mmol), DMSO 100ml, 150 DEG C of reflux 12h.Be cooled to room temperature to pour in 200ml water and separate out a large amount of solid and stir 0.5h, suction filtration obtains white solid, and column chromatography is purified to obtain white solid, yield 88%;
1h NMR (300MHz, CDCl
3): δ ppm 8.20 (d, 4H, J=5.7Hz), 8.13 (d, 2H, J=5.7Hz), 8.07 (s, 2H), 7.67 (d, 2H, J=6Hz), 7.60-7.54 (m, 8H), 7.49-7.36 (m, 8H).
Embodiment (8): the synthesis of 2,4-CzCO
2,4 difluorobenzene ketone (0.59g, 2.7mmol), salt of wormwood (2.23g, 16.1mmol), carbazole (0.99g, 5.9mmol), DMSO 8ml, 150 DEG C of reflux 12h.Be cooled to room temperature to pour in 200ml water and separate out a large amount of solid and stir 0.5h, suction filtration obtains white solid, and column chromatography is purified to obtain faint yellow solid, yield 90%.
1H NMR(300MHz，CDCl
3)：δppm 8.17(d，3H J＝8.1Hz)，7.90(t，2H，J＝8.4Hz)，7.83(d，2H，J＝7.5Hz)，7.66(d，2H，J＝8.1Hz)，7.51-7.32(m，8H)，7.21-7.13(m，4H)，7.02(t，1H，J＝7.4Hz)6.76(t，2H，J＝7.8Hz)。
Embodiment (9): the synthesis of 2,4 '-CzCO
2,4 '-difluorobenzophenone (0.59g, 2.7mmol), salt of wormwood (2.23g, 16.1mmol), carbazole (0.99g, 5.9mmol), DMSO 8ml, 150 DEG C of reflux 12h.Be cooled to room temperature to pour in 200ml water and separate out a large amount of solid and stir 0.5h, suction filtration obtains white solid, and column chromatography is purified to obtain faint yellow solid, yield 88%.
1H NMR(300MHz，CDCl
3)：δppm 8.10(t，3H，J＝8.1Hz)，7.92(t，3H，J＝9.9Hz)，7.77(t，2H，J＝7.8Hz)，7.50-7.29(m，12H)，6.94(t，4H，J＝7.1Hz)。
Embodiment (10): the synthesis of 4,4 '-CzCN
4,4 '-difluorobenzophenone (0.59g, 2.7mmol), salt of wormwood (2.23g, 16.1mmol), carbazole (0.99g, 5.9mmol), DMSO 8ml, 150 DEG C of reflux 12h.Be cooled to room temperature to pour in 200ml water and separate out a large amount of solid and stir 0.5h, suction filtration obtains white solid, and column chromatography is purified to obtain yellow solid, yield 84%.
1H NMR(300MHz，CDCl
3)：δppm 8.43-8.17(m，8H)，7.81(d，4H，J＝8.4Hz)，7.57(d，4H，J＝8.1Hz)，7.47(t，4H，J＝7.5Hz)，7.35(t，4H，J＝7.2Hz)。
The present invention has prepared a series of carbazole compound, respectively as the material of main part of electro phosphorescent device luminescent layer.Green device structure is: ITO/PEDOT:PSS (40nm)/(1)-(10): Ir (mppy)
3(6%, 40nm)/TmPyPB (60nm)/LiF (0.8nm)/Al (80nm).The device architecture of blue light is ITO/PEDOT:PSS (40nm)/(1)-(7): FIrpic (10%, 40nm)/TmPyPB (60nm)/LiF (0.8nm)/Al (80nm).The maximum current efficiency preparing green device with above-mentioned series material reaches 17.58cd/A, blue-light device maximum efficiency reach 9.89cd/A.By the structure of optimised devices, the performance of device still has very large room for promotion.
Claims (9)
1. a class is based on the compound of carbazole and cyanophenyl or benzophenone, and its structural formula is as follows:
2. one kind is synthesized the method for compound as claimed in claim 1, it is characterized in that directly forming carbonnitrogen bond under without the need to the condition of noble metal catalyst, and the universal method of easy, high efficiency condition is gentle such carbazole compound of synthesis, reaction committed step is as follows:
Carbazole, fluoro benzonitrile or fluoro benzophenone, alkali, adds solvent, and nitrogen atmosphere backflow 5-12h, the method separating-purifying of ethyl alcohol recrystallization or column chromatography is directly passed through in aftertreatment.
3. method according to claim 2, is characterized in that: described organic solvent is the one in methyl-sulphoxide or DMF.
4. method according to claim 2, is characterized in that: described alkali is salt of wormwood, cesium carbonate, sodium hydroxide, potassium hydroxide, potassium tert.-butoxide, in sodium tert-butoxide or sodium hydride any one.
5. compound according to claim 1, containing having the carbazole unit of hole transport performance and having the cyanophenyl of electronic transmission performance or the compound of benzophenone unit, as blue light or green glow phosphorescent light body material.
6. a compound as claimed in claim 1 is as the application of bipolar carrier transmission material.
7. the application of electroluminescent device according to claim 6, comprise glass, the Conducting Glass layer be attached on glass, the hole injection layer closed with Conducting Glass laminating, the luminescent layer of fitting with hole injection layer, the electron transfer layer of fitting with luminescent layer, the cathode layer of fitting with electron transfer layer, is characterized in that: described luminescent layer contains compound according to claim 1.
8. electroluminescent device according to claim 7, is characterized in that: luminescent layer is made up of material of main part and dopant material, and the material of main part of luminescent layer is compound as claimed in claim 1.
9. electroluminescent device according to claim 8, is characterized in that: dopant material is FIrpic or Ir (mppy)
3.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201510040719.2A CN104725298A (en) | 2015-01-23 | 2015-01-23 | Carbazole compounds, synthesis and application thereof in OLEDs (organic light emitting diodes) |
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| CN201510040719.2A Pending CN104725298A (en) | 2015-01-23 | 2015-01-23 | Carbazole compounds, synthesis and application thereof in OLEDs (organic light emitting diodes) |
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| CN114075131A (en) * | 2021-01-05 | 2022-02-22 | 吉林奥来德光电材料股份有限公司 | TADF material, preparation method thereof and organic electroluminescent device thereof |
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