CN101274916B - Multifunctional bipolar carrier transmission material and application thereof - Google Patents
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- CN101274916B CN101274916B CN2008100475927A CN200810047592A CN101274916B CN 101274916 B CN101274916 B CN 101274916B CN 2008100475927 A CN2008100475927 A CN 2008100475927A CN 200810047592 A CN200810047592 A CN 200810047592A CN 101274916 B CN101274916 B CN 101274916B
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- 239000000463 material Substances 0.000 title claims abstract description 39
- 230000005540 biological transmission Effects 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 230000005525 hole transport Effects 0.000 claims abstract description 9
- 125000006617 triphenylamine group Chemical group 0.000 claims abstract description 5
- 239000011521 glass Substances 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 7
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 5
- 230000004888 barrier function Effects 0.000 claims description 4
- 238000010030 laminating Methods 0.000 claims 6
- 239000002019 doping agent Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 4
- -1 triphenyl amines compound Chemical class 0.000 abstract description 2
- 241001025261 Neoraja caerulea Species 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 34
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 12
- 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 9
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 7
- 238000005401 electroluminescence Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- TWWQCBRELPOMER-UHFFFAOYSA-N [4-(n-phenylanilino)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 TWWQCBRELPOMER-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- FRYDBJOVRRDXQW-UHFFFAOYSA-N 2,5-bis(2-bromophenyl)-1,3,4-oxadiazole Chemical compound BrC1=CC=CC=C1C1=NN=C(C=2C(=CC=CC=2)Br)O1 FRYDBJOVRRDXQW-UHFFFAOYSA-N 0.000 description 1
- HGPVZVIPOXMTJD-UHFFFAOYSA-N 2,5-bis(4-bromophenyl)-1,3,4-oxadiazole Chemical compound C1=CC(Br)=CC=C1C1=NN=C(C=2C=CC(Br)=CC=2)O1 HGPVZVIPOXMTJD-UHFFFAOYSA-N 0.000 description 1
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000007777 multifunctional material Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
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Abstract
The invention discloses a compound which contains a triphenylamine unit with hole transport function and an oxdiazole unit with electronic transport function, the structure general formula is as the lower right, wherein Ar is a triphenyl amines compound with hole transport function. The synthesizing method of the multifunction compound of the invention is simple in operation and applicable for wide use. As transmission material of bipolar carrier, the compound of the invention can be applied to making an electroluminescent device in a blue-ray electrofluor optic device, has the advantages of the electroluminescent performance of high efficiency and high brightness and can be widely used in the organic electroluminescent field.
Description
Technical Field
The invention relates to the field of organic electroluminescent materials, in particular to a blue luminescent material with bipolar carrier transmission performance and application thereof in the field of electroluminescence.
Background
Organic electroluminescence has attracted great attention since the first report by kodak company c.w.tang et al in 1987 that a two-layer device structure using Alq3 as a light-emitting material was prepared by a vacuum evaporation method.
Organic electroluminescence can be classified into fluorescence and phosphorescence electroluminescence. According to the theory of spin quantum statistics, the probability ratio of formation of singlet excitons to triplet excitons is 1: 3, i.e. singlet excitons represent only 25% of the "electron-hole pairs". Thus, the fluorescence from radiative transitions of singlet excitons can account for only 25% of the total input energy, while the electroluminescence of phosphorescent materials can utilize the energy of all excitons and thus have a greater advantage.
Forrest and Thompson et al [ M a Baldo, S Lamansky, p.e. burroos, M EThompson, s.r. Forrest. appl Phys Let, 1999, 75, 4, 1999.]Mixing the green phosphorescent material Ir (ppy)3The organic light emitting diode is doped in a main body material of 4, 4 '-N, N' -dicarbazole-biphenyl (CBP) at a concentration of 6 wt%, a hole blocking layer material 2, 9-dimethyl 4, 7-diphenyl-1, 10-phenanthroline (BCP) is introduced, the maximum external quantum efficiency of the obtained green light OLED reaches 8%, the power efficiency reaches 31 lumens per watt (lm/W), and the organic light emitting diode greatly exceeds an electroluminescent luminescent device, so that people can immediately pay attention to heavy metal complex luminescent materials.
Red light iridium complexes (piq) were reported in 2003 by Y T Tao et al (Y. -j.su, h. -l.huang, c. -l.li, c. -h.chien, Y. -t.tao, p. -t.chou, s.datta, r. -s.liu, adv.mater, 2003, 15, 884)2Ir (acac) is doped in the main body CBP to prepare the device, the maximum external quantum efficiency of which reaches 9.71 percent, and the current efficiency and the power efficiency when the external quantum efficiency is 9.21 percent are respectively 8.22 candela per ampere (cd/A) and 2.34 lm/W.
The host-guest structure is mostly adopted in the prior phosphorescent electroluminescent device, namely, a phosphorescent emission substance is doped in the host substance at a certain concentration so as to avoid concentration quenching and triplet-triplet annihilation and improve the phosphorescent emission efficiency.
In the currently reported tricolor phosphorescent materials, only green light emission has achieved commercial requirements in terms of efficiency and color purity, while the red phosphorescent material has contradiction between color purity and efficiency. Currently, 4 '-N, N' -dicarbazole-biphenyl (CBP) is most reported as a host material for red phosphorescence, but CBP is easily crystallized by itself and is not well matched with the energy level of an adjacent hole transport layer in a device, thereby causing degradation of device performance. Therefore, the development of a red phosphorescent host material with good thermal stability and a proper energy level is significant. For blue phosphorescent materials, the reported y-values of the color coordinates are generally greater than the standards established by the international commission on illumination (CIE) (less than 0.2). Therefore, the development of blue fluorescent electroluminescent materials with high performance and good color purity is still one of the current research hotspots.
The bipolar carrier transport material has both electron and hole transport properties, can balance the injection and transport of carriers in a device, and simplify the structure of the device, thereby receiving wide attention. In recent years, host materials for bipolar carrier transport have also been reported. For example, Lee et al (Lee, Jiun-Haw; Tsai, Hsin-Hun; Leung, Man-Kit; Yang, Chih-Chiang; Chao, Chun-Chieh. applied Physics Letters, 2007, 90, 243501), prepared by mixing Ir (ppy)32, 2' -bis- [ 5-phenyl-2- (1, 3, 4) -oxadiazolyl doped with oxadiazole host material with bipolar transport at a concentration of 9 wt%]In biphenyl, the current efficiency of the device is 1000 Kantra per square meter (cd/m) at luminance2) It is 24cd/A, slightly smaller than CBP-based devices. Lai et al (Mei-Yi Lai, Chih-HsinChen, Wei-Sheng Huang, Jiann T.Lin, Tung-Huei Ke, Li-Yin Chen, Ming-HanTsai, Chung-Chih Wu.Angew.chem.int.Ed.2008, 47, 581) report bipolar carrier transport materials based on triphenylamine and benzimidazole. As the luminescent layer of the undoped blue fluorescent device, the maximum current efficiency of 2.8cd/A is obtained, and as the single-layer device prepared by the main material of orange phosphorescence, the maximum external quantum efficiency is 7.8%. The bipolar carrier transport materials reported so far are all used as hosts of green and orange phosphorescence, and no report is found yet as a host of red phosphorescence.
According to the invention, the triphenylamine unit with the hole transmission performance and the oxadiazole unit with the electron transmission performance are connected in different modes, so that the compound with the bipolar carrier transmission performance is prepared. The blue light emitting material is used as the light emitting layer material of an electroluminescent device, and the maximum current efficiency of the prepared blue light emitting device reaches 4cd/A, which is reported at presentThe performance of the fluorescent device is very outstanding. In addition, they were used as red phosphorescent materials (piq)2The emission peak value of the prepared red light device is located at 630nm, the maximum current efficiency reaches 11.3cd/A, the maximum power efficiency is 8.21m/W, and the maximum external quantum efficiency is 14.2%, which is far higher than that of a device taking CBP as a main body, and the red light device is one of the best single light-emitting layer devices so far.
Meanwhile, the compound can be used for high-efficiency blue luminescence and can also be used as a main body of high-efficiency red phosphorescence, and a single-luminescent-layer and single-doped white electroluminescent device is prepared.
Disclosure of Invention
The invention aims to provide a compound with bipolar carrier transmission performance and application thereof, and the compound has better performance and effect when being used as a luminescent layer material to prepare an electroluminescent device.
The compound with bipolar carrier transmission performance described in the invention contains triphenylamine unit with hole transmission performance and oxadiazole unit with electron transmission performance, and the structural general formula is as follows:
in the formula,
namely Ar is 4-triphenylamine phenyl, 2-triphenylamine phenyl or 3-triphenylamine phenyl.
The electroluminescent device comprises glass, a conductive glass substrate layer attached to the glass, and a conductive glass substrate layer adhered to the conductive glass substrate layerThe hole injection layer that closes, the hole transport layer that laminates with the hole injection layer, the luminescent layer that laminates with the hole transport layer, the hole barrier layer that laminates with the luminescent layer, the electron transport layer that laminates with the hole barrier layer, the cathode layer that laminates with the electron transport layer. Wherein the luminescent layer of the fluorescent device is composed of the material described in the formula (1), the luminescent layer of the red phosphorescent device and the luminescent layer of the white light device take the compound described in the formula (1) as a host material, and the doping material is common iridium complex with a ring metal ligand, such as Ir (piq) emitting red light2(acac)。
The bipolar carrier transmission material is applied to a blue light electroluminescent fluorescent optical device, and can obtain the maximum current efficiency of 4 cd/A. The invention takes Ir (piq)2(acac) is a red electrophosphorescent device prepared by taking the guest as a target, the color coordinate CIE is (0.68, 0.32), and the maximum brightness reaches 24416 (cd/m)2) The maximum luminous efficiency can reach 11.3cd/A, the maximum power efficiency can reach 8.2lm/W, the maximum external quantum efficiency can reach 14.2 percent, and the red phosphor device is one of the best performances in the red phosphor device with the same color purity. The color coordinate of the prepared simple white light device at the driving voltage of 11V is (0.37, 0.31), and the maximum current efficiency is 7.9 cd/A.
Drawings
FIG. 1 is a schematic diagram of an electroluminescent device of the present invention;
fig. 2 emission spectrum of an electroluminescent device according to the invention.
Detailed Description
The invention is further illustrated by the following specific examples, which are intended to facilitate a better understanding of the contents of the invention, but which are not intended to limit the scope of the invention in any way.
The starting materials used in this embodiment are known compounds, are commercially available, or may be synthesized by methods known in the art.
Example 1
Preparation of 2, 5-bis (4-4' -triphenylaminophenyl) -1, 3, 4-oxadiazole (abbreviated as Host1)
0.38 g of 2, 5-bis- (4-bromophenyl) -1, 3, 4-oxadiazole and 0.6 g of triphenylamine-4-boronic acid, a little of tetrakistriphenylphosphine palladium, 1.06 g of sodium carbonate, 10 ml of tetrahydrofuran and 2 ml of water are added into a 50 ml flask, refluxed for 24 hours under the protection of argon, cooled, extracted with dichloromethane, and the organic phase is dried by anhydrous sodium carbonate, filtered and dried by spinning. The mixture is passed through a column with the volume ratio of dichloromethane to petroleum ether being 1: 1 to obtain 0.49 g of product. Pale yellow solid, yield 70%.1H-NMR(CDCl3，300MHz)δ[ppm]：8.18(t，4H)，8.02(d，2H)，7.71(m，6H)，7.53(d，4H)，7.29(m，12H)，7.20(d，4H)，7.06(t，4H)，MS(EA)：m/e 708.6(M+)。
Example 2
Preparation of 2, 5-bis (2-4' -triphenylaminophenyl) -1, 3, 4-oxadiazole (abbreviated as Host2)
0.38 g of 2, 5-bis- (2-bromophenyl) -1, 3, 4-oxadiazole and 0.60 g of triphenylamine-4-boronic acid, a little of tetrakistriphenylphosphine palladium, 0.56 g of potassium hydroxide, 10 ml of tetrahydrofuran and 2 ml of water are added into a 50 ml flask, refluxed for 24 hours under the protection of argon, cooled, extracted with dichloromethane, and the organic phase is dried by anhydrous sodium carbonate, filtered and dried by spinning. The mixture is passed through a column with the volume ratio of dichloromethane to petroleum ether being 1: 1 to obtain 0.60 g of product. White solid, yield 85%. .1H-NMR(CDCl3，300MHz)δ[ppm]7.86(d，2H)，8.27(m 2H)，7.58(t，2H)，7.48(t，4H)，7.16(t，8H)，3.97(d 20H).MS(EA)：m/e 708.2(M+)。
Example 3
Preparation of 2, 5-bis (3-4' -triphenylaminophenyl) -1, 3, 4-oxadiazole (abbreviated as Host3)
2, 5-bis (3-4' -triphenylaminophenyl) -1, 3, 4-oxadiazole was obtained in a similar manner to example 1. The yield was 65%.1H-NMR(CDCl3，300MHz)δ[ppm]8.35(s，2H)，8.09(d，2H)，7.75(d，2H)，7.57(m，6H)，7.28(m，8H)，7.17，(m，12H)，7.06，(t，4H).MS(EA)：m/e 708(M+)
Example 4
Preparation of electrophosphorescent devices
As shown in FIG. 1, the electroluminescent device with the bipolar carrier transport material as the luminescent layer of the invention can comprise a glass and conductive glass (ITO) substrate layer 1, a hole injection layer 2 (molybdenum trioxide MoO)3) A hole transport layer 3(4, 4' -bis (N-phenyl-N-naphthyl) -biphenyl NPB), a light emitting layer 4 (the compound having a bipolar carrier transport property of the present invention or a phosphorescent complex doped with the compound as a host material), a hole blocking layer 5(2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline BCP), an electron transport layer 6 (tris-8-hydroxyquinoline aluminum Alq3), and a cathode layer 7 (lithium fluoride/aluminum).
Electroluminescent devices may be fabricated according to methods known in the art, for example as disclosed in the references (adv. mater.2003, 15, 277). The specific method comprises the following steps: sequentially evaporating MoO on a cleaned conductive glass (ITO) substrate under a high vacuum condition3NPB, light-emitting layer, BCP at 10nm, Alq3 at 30nm, LiF at 1nm and Al at 120 nm. The device shown in figure 1 is made in this way,various specific device structures are as follows:
device 1 (D1):
ITO/MoO3(10nm)/NPB(80nm)/Host1(20nm)/BCP(10nm)/Alq3(30nm)/LiF(1nm)/Al(120nm)
device 2 (D2):
ITO/MoO3(10nm)/NPB(80nm)/Host2(20nm)/BCP(10nm)/Alq3(30nm)/LiF(1nm)/Al(120nm)
device 3 (D3):
ITO/MoO3(10nm)/NPB(80nm)/Hostl：Ir(piq)2(acac)(6wt％，20nm)/BCP(10nm)/Alq3(30nm)/LiF(1nm)/Al(120nm)
device 4 (D4):
ITO/MoO3(10nm)/NPB(80nm)/Host2：Ir(piq)2(acac)(6wt％，20nm)/BCP(10nm)/Alq3(30nm)/LiF(1nm)/Al(120nm)
device 5 (D5):
ITO/MoO3(10nm)/NPB(80nm)/Host3：Ir(piq)2(acac)(6wt％，20nm)/BCP(10nm)/Alq3(30nm)/LiF(1nm)/Al(120nm)
device 6 (D6):
ITO/NPB(40nm)/Host1：Ir(piq)2(acac)(0.1wt％，30nm)/BCP(10nm)/Alq3(30nm)/LiF(1nm)/Al(120nm)
the current-luminance-voltage characteristics of the device were obtained with a Keithley source measurement system (Keithley 2400 source meter, Keithley 2000 Currentmeter) with calibrated silicon photodiodes, the electroluminescence spectra were measured with a SPEX CCD3000 spectrometer, JY, france, all in ambient air.
The device performance data is shown in the following table:
Claims (4)
1. The compound contains triphenylamine units with hole transmission and oxadiazole units with electron transmission, and has the structural general formula:
wherein,
ar is simultaneously
2. Use of the compound of claim 1 as a bipolar carrier transport material.
3. The utility model provides an electroluminescent device, includes glass, the conductive glass substrate layer of attached to on glass, the hole injection layer with the laminating of conductive glass substrate layer, the hole transport layer with the laminating of hole injection layer, the luminescent layer with the laminating of hole transport layer, the hole barrier layer with the laminating of luminescent layer, the electron transport layer with the laminating of hole barrier layer, the cathode layer with the laminating of electron transport layer, its characterized in that: the light-emitting layer contains the compound according to claim 1.
4. An electroluminescent device as claimed in claim 3, characterized in that: the light-emitting layer is composed of a host material and a dopant material, and the host material of the light-emitting layer is the compound according to claim 1.
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| CN101463251B (en) * | 2008-12-31 | 2012-08-01 | 武汉大学 | Electro-phosphorescent main body material with bipolar carrier transmission performance and use thereof |
| US8604689B2 (en) * | 2010-11-11 | 2013-12-10 | Nitto Denko Corporation | Hybrid composite emissive construct and light-emitting devices using the same |
| WO2013039914A1 (en) | 2011-09-12 | 2013-03-21 | Nitto Denko Corporation | Efficient organic light-emitting diodes and fabrication of the same |
| CN103183711B (en) * | 2011-12-28 | 2016-04-20 | 昆山维信诺显示技术有限公司 | A kind of two-triaryl amine replaces phosphine oxygen base Benzophenanthrene compound, intermediate and preparation method and application |
| CN104017564A (en) * | 2013-02-28 | 2014-09-03 | 海洋王照明科技股份有限公司 | Bipolar blue-phosphorescence material, preparation method thereof and organic electroluminescent device |
| CN104119290A (en) * | 2013-04-25 | 2014-10-29 | 海洋王照明科技股份有限公司 | Organic semiconductor material, preparation method thereof and electroluminescent device |
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| CN1546477A (en) * | 2003-12-04 | 2004-11-17 | 复旦大学 | Method for preparing electron transport / hole barrier material and its electro-glow parts |
| WO2004107822A1 (en) * | 2003-05-29 | 2004-12-09 | Nippon Steel Chemical Co., Ltd. | Organic electroluminescent element |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004107822A1 (en) * | 2003-05-29 | 2004-12-09 | Nippon Steel Chemical Co., Ltd. | Organic electroluminescent element |
| CN1546477A (en) * | 2003-12-04 | 2004-11-17 | 复旦大学 | Method for preparing electron transport / hole barrier material and its electro-glow parts |
Non-Patent Citations (3)
| Title |
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| JP特开2004－331587A 2004.11.25 |
| JP特开平5－255664A 1993.10.05 |
| JP特开平8－311051A 1996.11.26 |
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