CN1793280A - Cyclic metallic platinum compounding agent electrofluor scence material containing triaryl amine functional redical - Google Patents
Cyclic metallic platinum compounding agent electrofluor scence material containing triaryl amine functional redical Download PDFInfo
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Abstract
The invention relates to ring metal platinum complexes electro phosphorescence material containing tri-fragrant amine function group. Its manufacturing includes the following steps: linkage of pyridine heterocyclic compound and tri-fragrant amine to form CN bi-tooth ligand; further reacting with platinum ion and OO anion auxiliary ligand to gain the new type single ring metal platinum complexes electro phosphorescence material. The invention mixes ring metal platinum complexes with PFO and PVK to form polymer electro phosphorescence device. It can adjudge electronic structure, hole-injection, and transmission performance to renovate electroluminescence of the device. The invention can be applied to organic electroluminescence field, especially used to manufacture high performance organic electroluminescence device.
Description
Technical field
The present invention relates to a kind of organic electromechanical phosphorescent material, particularly a kind of Cyclometalated platinum complexes electromechanical phosphorescent material that contains three arylamine functional groups.
Background technology
The Forrest group reported first of Princeton university in 1998 octaethyl puff quinoline is closed platinum (II) title complex (PtOEt) be entrained in oxine and close aluminium (Alq
3) in, having obtained internal quantum efficiency is 23%, external quantum efficiency is 4% electro phosphorescent device (M.A.Baldo, D.F.O ' Brien, Y.You, et al.Nature, 1998,395,151), caused the very big interest of people immediately to electromechanical phosphorescent material and device thereof.Subsequently, organic iridium (Ir) (Appl.Phys.Lett.2001,78,1622.Adv.Funct.Mater.2005,15,1451), platinum (Pt) (Appl.Phys.Lett.2005,86,153505, Adv.Funct.Mater.2005,15,223), osmium (Os) (Chem.Mater.2005,17,3532), ruthenium (Ru) (Adv.Mater.2005,17,1059) research of title complex electromechanical phosphorescent material has obtained development rapidly.
Because the relative ring metal iridium complex of organic Cyclometalated platinum complexes has long phosphorescent lifetime (30～50 μ s), its structure is a two dimensional structure, therefore it is generally acknowledged that organic Cyclometalated platinum complexes is easy to generate the phosphorescence cancellation, and luminous efficiency is difficult to improve.The Sotoyama group of Fujitsu in 2005 has designed the N^C^N tridentate ligand, obtained (OPh) (Appl.Phys.Lett.2005 of novel Cyclometalated platinum complexes Pt (dpt), 86,153505), the external quantum efficiency of its adulterated organic molecule electro phosphorescent device has reached 16.5%; The Chi group of Taiwan National Tsing Hua University has designed the N^N bidentate ligand, has obtained Cyclometalated platinum complexes Pt (iqdz)
2(Adv.Funct.Mater.2005,15,223), the external quantum efficiency of its adulterated organic molecule electro phosphorescent device has also reached 14.9%.This shows: the Cyclometalated platinum complexes by the design novel texture, can reduce the phosphorescence cancellation of Cyclometalated platinum complexes effectively, and improve luminous efficiency.
The kind of existing Cyclometalated platinum complexes electromechanical phosphorescent material seldom, the Cyclometalated platinum complexes electromechanical phosphorescent material of high-luminous-efficiency still less, therefore, provide the Cyclometalated platinum complexes electromechanical phosphorescent material of multiple class very important, particularly the exploitation based on the Cyclometalated platinum complexes electromechanical phosphorescent material of the high-efficiency polymer electro phosphorescent device of Cyclometalated platinum complexes just seems even more important.
Summary of the invention
At above-mentioned situation, the electromechanical phosphorescent material that the purpose of this invention is to provide a kind of novel Cyclometalated platinum complexes that contains three arylamine functional groups, this material has nonplanar structure and good current carrier injection, composite performance and good luminescent properties, thereby realizes efficiently luminous based on the electrostrictive polymer phosphorescent device of Cyclometalated platinum complexes.
For achieving the above object, the present invention is a raw material with commercially available 2-(4-nitrophenyl) pyridine, obtain 2-(4-aminophenyl) pyridine compounds A by reduction reaction, the Ullmann reaction that compd A and iodo aromatic hydrocarbons improve, obtain the triarylamine compounds B that pyridyl replaces, compd B and potassium chloroplatinite generation chlorine bridging and go bridging reaction obtain containing the monocycle metal platinum complex electromechanical phosphorescent material C of triarylamine, and its molecular structure is:
In the formula: R
1Be alkyl, hydrogen atom, R
2Be methyl, phenyl.
In order to obtain high efficiency electrostrictive polymer phosphorescent device, the monocycle metal platinum complex electromechanical phosphorescent material C that this class is novel is as the dopant material of electrostrictive polymer phosphorescent device, and constitute the luminescent layer of electrostrictive polymer phosphorescent device with polymer main body material, its further step is:
The dopant material that constitutes electrostrictive polymer phosphorescent device luminescent layer is Cyclometalated platinum complexes C, and its doping weight concentration is 1%～8%.The polymer main body material that constitutes the electro phosphorescent device luminescent layer is a conjugated 9, and the 9-dihexyl gathers fluorenes (PFO) and 2-(4-tert-butyl-phenyl)-5-biphenyl-1,3, the blend of 4-oxadiazole ring metal (PBD); Or unconjugated polyvinyl carbazole (PVK) and 2-(4-tert-butyl-phenyl)-5-biphenyl-1,3, the blend of 4-oxadiazole ring metal (PBD), 2-(4-tert-butyl-phenyl)-5-biphenyl-1 wherein, 3, the weight concentration of 4-oxadiazole ring metal (PBD) is 30% in PFO, is 20% in PVK.
The present invention adopts pyridine-heterocyclic compound by covalent linkage and three arylamine bondings, obtain the C^N bidentate ligand of a class nonplanar structure, further with platinum ion and the reaction of O^O negatively charged ion assistant ligand, obtain the novel monocycle metal platinum complex electromechanical phosphorescent material C of a class, it has solved the deficiency of existing Cyclometalated platinum complexes electromechanical phosphorescent material kind rareness.The Cyclometalated platinum complexes electromechanical phosphorescent material that contains triarylamine provided by the invention is the luminescent material that a class has good hole transport performance, its nonplanar structure and good current carrier injection, composite performance and good luminescent properties can be realized efficiently luminous based on the electrostrictive polymer phosphorescent device of Cyclometalated platinum complexes.
The present invention is with Cyclometalated platinum complexes C and conjugated 9, the 9-dihexyl gathers fluorenes (PFO) and 2-(4-tert-butyl-phenyl)-5-biphenyl-1,3,4-oxadiazole ring metal (PBD) blend, inclusive NAND conjugated polyvinyl carbazole (PVK) and 2-(4-tert-butyl-phenyl)-5-biphenyl-1,3,4-oxadiazole ring metal (PBD) blend, making is based on the electrostrictive polymer phosphorescent device of Cyclometalated platinum complexes, and device is 7.0mA/cm in current density
2Current drives under, luminosity is 1130cd/m
2, maximum luminous efficiency has reached 10.6%.
The present invention is by introducing three arylamine functional groups in material, can regulate the on-plane surface electronic structure and the hole of material easily injects and transmission performance, thereby refreshed the electroluminescent properties of such Cyclometalated platinum complexes in the electrostrictive polymer phosphorescent device, to satisfy people to many kinds of electromechanical phosphorescent material demands of applications.The present invention can be widely used in the organic electroluminescent field, especially for preparation high performance electroluminescent organic device.
Below in conjunction with drawings and Examples the present invention is further described.
Description of drawings
Fig. 1 is [N, N-two (4-tert-butyl-phenyl)-4-(2 '-pyridyl) aniline-C of the present invention
3, N
1] (phenyl phenacyl ketone) close the uv-visible absorption spectra figure of platinum (II) [(BuPhNPPy) Pt (DBM)] solid film.
Fig. 2 is the fluorescence emission spectrogram of (BuPhNPPy) of the present invention Pt (DBM) solid film.
Fig. 3 is [N, N-phenylbenzene-4-(2 '-pyridyl) aniline-C of the present invention
3, N
1] (phenyl phenacyl ketone) close the uv-visible absorption spectra figure of platinum (II) [(PhNPPy) Pt (DBM)] solid film.
Fig. 4 is the fluorescence emission spectrogram of (PhNPPy) of the present invention Pt (DBM) solid film.
Fig. 5 is the electroluminescent spectrum figure of (BuPhNPPy) of the present invention Pt (DBM)-PVK-PBD polymer device.
Fig. 6 is the electroluminescent spectrum figure of (PhNPPy) of the present invention Pt (DBM)-PVK-PBD polymer device.
Fig. 7 is the electroluminescent spectrum figure of (PhNPPy) of the present invention Pt (DBM)-PFO-PBD polymer device.
Fig. 8 is the external quantum efficiency and the current density graphic representation of (PhNPPy) of the present invention Pt (DBM)-PFO-PBD polymer device.
Fig. 9 is the brightness and the voltage curve of (PhNPPy) of the present invention Pt (DBM)-PFO-PBD polymer device.
Figure 10 is the current density curve and the voltage curve of (PhNPPy) of the present invention Pt (DBM)-PFO-PBD polymer device.
Embodiment
Synthesizing of 2-(4-aminophenyl) pyridine
In the 100mL there-necked flask, add 4.0g (20mmol) 2-(4-nitrophenyl) pyridine and 40mL ethanol, be heated to 50 ℃, add 0.2g 5%Pd-C, within 40min, add 4mL 80% hydrazine hydrate and 0.2g 5%Pd-C, back flow reaction 4hr more successively.After boiling off most of ethanol, add 15mL water, separate out white solid, suction filtration washes with water, and vacuum-drying gets white crystal 3.4g, productive rate 98.8%.Fusing point (m.p) .96～97 ℃ ([9] 97～98 ℃ of literature values).Infrared spectra (IR) (KBr, cm
-1): 3452,3306 (N-H), 3190 (Ar-NH2 resultant peaks), 1631,1606,1522,1470 (aromatic ring frames), 836 (1, the 4-disubstituted benzenes).Nucleus magnetic hydrogen spectrum (1HNMR) (400MHz, CDCl
3) δ ppm:8.62 (d, 1H), 7.83 (d, 2H), 7.70～7.61 (m, 2H), 7.14～7.09 (t, 1H), 6.76 (d, 2H), 3.81 (s, 2H).
Embodiment 2
N, N-two (4-tert-butyl-phenyl)-4-(2 '-pyridyl) aniline (BuPhNPPy) synthetic
1.0g (5.9mmol) 2-(4-aminophenyl) pyridine, 3.8g (14.6mmol) 4-tertiary butyl iodobenzene, 6.6g Anhydrous potassium carbonate, 1.5g activated copper powder, 0.4g dibenzo-18-hat-6 and 20mL orthodichlorobenzene are joined in the 100mL there-necked flask; under nitrogen protection; reflux 21hr, cooling, suction filtration; orthodichlorobenzene is reclaimed in underpressure distillation; residuum is a stationary phase with 200～300 order silica gel, and methylene dichloride is an eluent, through column chromatography for separation; obtain the 1.2g white solid, yield is 46.8%.m.p.228～230℃。1HNMR(400MHz，CDCl
3)δppm：8.54(d，1H)，7.85(d，2H)，7.64～7.70(m，2H)，7.28(d，4H)，7.04～7.17(m，7H)，1.32(s，18H)。
Embodiment 3
N, N-phenylbenzene-4-(2 '-pyridyl) aniline (PhNPPy) synthetic
1.5g (8.9mmol) 2-(4-aminophenyl) pyridine, 2.5mL (21.9mmol) iodobenzene, 9.9g (71.7mmol) Anhydrous potassium carbonate, 2.3g activated copper powder, 0.6g dibenzo-18-hat-6 and 30mL orthodichlorobenzene are joined in the 100mL there-necked flask; under nitrogen protection; reflux 24hr; cooling; suction filtration; orthodichlorobenzene is reclaimed in underpressure distillation; residuum is a stationary phase with 200～300 order silica gel; methylene dichloride is an eluent; through column chromatography for separation; obtain the 1.5g white solid, yield is 51.7%.m.p.178～179℃。1HNMR(400MHz，CDCl
3)δppm：8.73～8.62(d，1H)，7.88～7.86(d，2H)，7.73～7.65(m，2H)，7.29～7.25(t，4H)，7.18～7.05(m，7H)，7.06～7.02(t，2H)。
Embodiment 4
[N, N-two (4-tert-butyl-phenyl)-4-(2 '-pyridyl) aniline-C
3, N
1] (phenyl phenacyl ketone) close the synthetic of platinum (II) [(BuPhNPPy) Pt (DBM)]
In the 50mL there-necked flask; add the 20mL ethylene glycol monoethyl ether; 7mL water; 0.6027g (1.39mmol) N, N-two (4-tert-butyl-phenyl)-4--(2 '-pyridyl) aniline and 0.2883g (0.69mmol) potassium chloroplatinite are under the nitrogen protection; be warming up to 80 ℃; magnetic agitation reaction 34hr, 12hr is left standstill in cooling, produces yellow-green precipitate.Suction filtration, solid are used cold ethylene glycol monoethyl ether (3mL * 3) and sherwood oil (2mL * 3) washing successively, and vacuum-drying gets 0.49g two [N, N-two (4-tert-butyl-phenyl)-4-(2 '-pyridyl) aniline-C
3, N
1] (μ-dichloro) close platinum (II) yellow-green colour solid, m.p.213～215 ℃.
With 0.4349g (0.328mmol) two [N, N-two (4-tert-butyl-phenyl)-4-(2 '-pyridyl) aniline-C
3, N
1] (μ-dichloro) close platinum (II), 0.2225g (1.0mmol) diphenylpropane-1,3-dione(DPPO), 0.3550gNa
2CO
3With the 18mL ethylene glycol monoethyl ether, join in the 50mL there-necked flask, under the nitrogen protection, be warming up to 100 ℃, magnetic agitation, reaction 34hr, cool to room temperature.Suction filtration, residue spent glycol list ether washing (6mL * 3), washings and filtrate merge, and the reclaim under reduced pressure ethylene glycol monoethyl ether gets the brownish black solid.Solid is stationary phase with silica gel, and toluene is eluent, and through column chromatography for separation, rotary evaporation is removed toluene, with ethanol and methylene dichloride recrystallization, obtains the yellow tiltedly square crystal of 0.24g, and the total recoverys of two steps reaction are 41.2%, m.p.233～235 ℃.1HNMR(400MHz，CDCl
3)δppm：8.65(d，1H)，8.03(d，1H)，7.87～7.85(d，1H)，7.83～7.66(m，3H)，7.49～7.22(m，8H)，7.20～6.73(m，10H)，5.30(s，1H)，1.30(s，18H)。
(BuPhNPPy) uv-visible absorption spectra of Pt (DBM) solid film is seen Fig. 1, and maximal ultraviolet-visible absorbance wavelength is 358nm, and at 443nm one little absorption peak is arranged.The fluorescence emission spectrum of solid film is seen Fig. 2, and maximum emission wavelength is 546nm, and at 574nm one acromion is arranged, the jaundice green light.
Embodiment 5
[N, N-phenylbenzene-4-(2 '-pyridyl) aniline-C
3, N
1] (phenyl phenacyl ketone) close the synthetic of platinum (II) [(PhNPPy) Pt (DBM)]
In the 50mL there-necked flask; add 0.4866g (1.51mmol) N; N-phenylbenzene-4-(2 '-pyridyl) aniline, 0.3133g (0.76mmol) potassium chloroplatinite, 18mL ethylene glycol monoethyl ether and 6mL water; under the nitrogen protection; be warming up to 80 ℃; magnetic agitation reaction 32hr, 12hr is left standstill in cooling, produces the yellow-green colour solid precipitation.Suction filtration, solid are used cold ethylene glycol monoethyl ether (3mL * 3) and sherwood oil (2mL * 3) washing successively, and vacuum-drying gets 0.16g two [N, N-phenylbenzene-4-(2 '-pyridyl) aniline-C
3, N
1] (μ-dichloro) close platinum (II) yellow-green colour solid, m.p. is not less than 300 ℃.
With 0.1367g (0.078mmol) two [N, N-phenylbenzene-4-(2 '-pyridyl) aniline-C
3, N
1] (μ-dichloro) close platinum (II), 83.4mg (0.372mmol) diphenylpropane-1,3-dione(DPPO), 0.1339gNa
2CO
3With the 10mL ethylene glycol monoethyl ether, join in the 50mL there-necked flask, under the nitrogen protection, be warming up to 100 ℃, magnetic agitation, reaction 22hr, cool to room temperature.Suction filtration, residue spent glycol list ether washing (5mL * 3), washings and filtrate merge, and the reclaim under reduced pressure ethylene glycol monoethyl ether gets the brownish black solid.Solid is stationary phase with silica gel, and toluene is eluent, and through column chromatography for separation, rotary evaporation is removed toluene, with ethanol and methylene dichloride recrystallization, obtains 100.4mg yellow fibers shape crystal, and yield is 87.0%, and m.p. is not less than 300 ℃.1HNMR(400MHz，CDCl
3)δppm：8.65(d，1H)，8.03(d，1H)，7.88～7.85(d，2H)，7.67(m，3H)，7.66～7.33(m，4H)，7.31～7.23(m，6H)，7.15～7.04(m，10H)。
(PhNPPy) uv-visible absorption spectra of Pt (DBM) solid film is seen Fig. 3, and its maximal ultraviolet-visible absorbance wavelength is 347nm, and at 413nm one little absorption peak is arranged.The fluorescence emission spectrum of solid film is seen Fig. 4, and its maximum emission wavelength is 539nm, and at 570nm one acromion is arranged, the jaundice green light.
Embodiment 6
The electrostrictive polymer phosphorescent device that contains the Cyclometalated platinum complexes of three arylamine functional groups comprises indium tin oxide target (ITO) conductive glass, cavitation layer, luminescent layer, cathode layer.Luminescent layer is made of polymer main body material and dopant material.As dopant material, make the electrostrictive polymer phosphorescent device with compound (BuPhNPPy) Pt (DBM) of embodiment 4, the structure and the layers of material of device are as follows:
ITO//PEDOT (100nm) // luminescent layer (70nm) //Ba (5nm) //Al (200nm)
The production process of device is as follows: on the ito glass substrate of handling well, poly-second two supports-3 of the 100nm of spin coated successively, 4-dioxy thiophthene (PEDOT) (Bayer Batron P4083) hole injection layer and 70nm luminescent layer, the aluminium (Al) of the barium of evaporation 5nm (Ba) layer and 200nm layer successively then.The light-emitting area of luminescent device is 0.15cm
2Luminescent layer is made up of dopant material [compound of embodiment 4 (BuPhNPPy) Pt (DBM)] and material of main part (PFO and PBD), wherein, the mass percent of dopant material in material of main part is 4%, and the mass ratio of material of main part PFO and PBD is PFO: PBD=80: 30.
(Tencor ALFA-Step500) measures the thickness of hole injection layer, hole transmission layer and luminescent layer with surface profiler.The thickness of Ba and Al and sedimentation velocity are measured with thickness/speed instrument (the STM-100 thickness/speed instrument of Sycon company), and the sedimentation velocity of Ba and Al is respectively 0.05～0.1nm/s and 1～2nm/s.All operations are all carried out in nitrogen glove box.
Electroluminescent spectrum (EL) is measured with the Instaspec4 CCD grating spectrograph of Oriel company; Luminous efficiency is measured with the silicon photoelectric diode of standard; Electroluminescent efficiency is with S80 type totalizing instrument (USLabshere company) and cooperate the UDT3 digital photometer to measure, and LASER Light Source is 325, the He-Cd laser apparatus (US Dmni Chrone company) of 442nm spectral line; Current-voltage (I-V) curve and luminous intensity-voltage (L-V) curve and external quantum efficiency are measured with Keithley source determinator.
(BuPhNPPy) electroluminescent spectrum of Pt (DBM)-PVK-PBD device as shown in Figure 5, maximum emission wavelength is 540nm, and 570 an acromion is arranged, maximum luminousing brightness is 1966cd/m
2, the jaundice green light, chromaticity coordinates is CIE (0.39,0.56), device is 1.9mA/cm in current density
2Current drives under, maximum external quantum efficiency is 3.6%.
Embodiment 7
As dopant material, make the electrostrictive polymer phosphorescent device with compound (PhNPPy) Pt (DBM) of embodiment 5, the structure and the layers of material of luminescent device are as follows:
ITO//PEDOT (100nm) // luminescent layer (70nm) //Ba (5nm) //Al (200nm)
The production process of device and testing method are identical with embodiment 6.But the mass percent of the dopant material of luminescent layer (PhNPPy) Pt (DBM) in material of main part is 2%.
(PhNPPy) electroluminescent spectrum of Pt (DBM)-PVK-PBD device as shown in Figure 6, the maximum emission wavelength of device is 535nm, and at 568nm one acromion is arranged, maximum luminousing brightness is 10420cd/m
2, the jaundice green light, chromaticity coordinates is CIE (0.39,0.56), device is 6.8mA/cm in current density
2Current drives under, maximum external quantum efficiency is 7.4%.
Embodiment 8
As dopant material, make the electrostrictive polymer phosphorescent device with compound (PhNPPy) Pt (DBM) of embodiment 5, the structure and the layers of material of luminescent device are as follows:
ITO//PEDOT (70nm) //PVK (40nm) // luminescent layer (70nm) //Ba (5nm) //Al (200nm)
The production process of device and testing method are identical with embodiment 6.But the mass percent of guest materials in material of main part is 4%.The mass ratio of material of main part PFO and PBD is PFO: PBD=80: 20.
(PhNPPy) electroluminescent spectrum of Pt (DBM)-PFO-PBD device as shown in Figure 7, the maximum emission wavelength of device is 539nm, and at 576nm one acromion is arranged, maximum luminousing brightness is 11900cd/m
2, the jaundice green light, chromaticity coordinates is CIE (0.42,0.57).The external quantum efficiency of device and current density curve, brightness and voltage curve, current density and voltage curve are respectively as Fig. 8, shown in 9,10.Device is 7.0mA/cm in current density
2Current drives under, maximum external quantum efficiency is 10.6%, this moment device luminosity be 1130cd/m
2
Embodiment 9
As dopant material, make the electrostrictive polymer phosphorescent device with compound (PhNPPy) Pt (DBM) of embodiment 5, the structure and the layers of material of luminescent device are as follows:
ITO//PEDOT (70nm) //PVK (40nm) // luminescent layer (70nm) //Ba (5nm) ∥ Al (200nm)
The production process of device and testing method are identical with embodiment 6.But the mass percent of dopant material in material of main part is 2%.
The maximum emission wavelength of device is 537nm, and at 573nm one acromion is arranged, and maximum luminousing brightness is 11951cd/m
2, the jaundice green light, chromaticity coordinates is CIE (0.41,0.57), device is 5.3mA/cm in current density
2Current drives under, maximum external quantum efficiency is 10.4%, this moment device luminosity be 851cd/m
2
Embodiment 10
As dopant material, make the electrostrictive polymer phosphorescent device with compound (PhNPPy) Pt (DBM) of embodiment 5, the structure and the layers of material of luminescent device are as follows:
ITO//PEDOT (70nm) //PVK (40nm) // luminescent layer (70nm) //Ba (5nm) //Al (200nm)
The production process of device and testing method are identical with embodiment 6.But the mass percent of dopant material in material of main part is 8%.
The maximum emission wavelength of device is 540nm, and at 573nm one acromion is arranged, and maximum luminousing brightness is 10570cd/m
2, the jaundice green light, chromaticity coordinates is CIE (0.42,0.57), device is 4.2mA/cm in current density
2Current drives under, maximum external quantum efficiency is 7.8%, this moment device luminosity be 505cd/m
2
Below only be preferred embodiment of the present invention, according to above-mentioned design of the present invention, those skilled in the art also can make various modifications and conversion to this.For example, the adjustment of compound, the selection of blend, the change of doping weight concentration and conversion of operational condition or the like.Yet similar this conversion and modification all belong to essence of the present invention.
Claims (6)
1, a kind of Cyclometalated platinum complexes electromechanical phosphorescent material that contains three arylamine functional groups is characterized in that the structure of the Cyclometalated platinum complexes of this electromechanical phosphorescent material is:
In the formula: R
1Be alkyl, hydrogen atom, R
2Be methyl, phenyl.
2, a kind of Cyclometalated platinum complexes electromechanical phosphorescent material that contains three arylamine functional groups according to claim 1, it is characterized in that the dopant material of Cyclometalated platinum complexes electromechanical phosphorescent material as the electrostrictive polymer phosphorescent device, this dopant material and conjugation or non-conjugate high molecular material of main part constitute electrostrictive polymer phosphorescent device luminescent layer.
3, a kind of Cyclometalated platinum complexes electromechanical phosphorescent material that contains three arylamine functional groups according to claim 2, it is characterized in that the dopant material of Cyclometalated platinum complexes electromechanical phosphorescent material as the electrostrictive polymer phosphorescent device, its doping weight concentration is 1%～8%.
4, a kind of Cyclometalated platinum complexes electromechanical phosphorescent material that contains three arylamine functional groups according to claim 2, the polymer main body material that it is characterized in that electrostrictive polymer phosphorescent device luminescent layer is a conjugated 9, the 9-dihexyl gathers fluorenes (PFO) and 2-(4-tert-butyl-phenyl)-5-biphenyl-1,3, the blend of 4-oxadiazole ring metal (PBD), or unconjugated polyvinyl carbazole (PVK) and 2-(4-tert-butyl-phenyl)-5-biphenyl-1,3, the blend of 4-oxadiazole ring metal (PBD).
5, a kind of Cyclometalated platinum complexes electromechanical phosphorescent material that contains three arylamine functional groups according to claim 4, it is characterized in that 2-(4-tert-butyl-phenyl)-5-biphenyl-1,3,4-oxadiazole ring metal (PBD) is the electron transport material of electro phosphorescent device luminescent layer, weight concentration when this electron transport material and conjugated 9,9-dihexyl gather fluorenes (PFO) blend is 30%.
6, a kind of Cyclometalated platinum complexes electromechanical phosphorescent material that contains three arylamine functional groups according to claim 4, it is characterized in that 2-(4-tert-butyl-phenyl)-5-biphenyl-1,3,4-oxadiazole ring metal (PBD) is the electron transport material of electro phosphorescent device luminescent layer, and the weight concentration when this electron transport material and unconjugated polyvinyl carbazole (PVK) blend is 20%.
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| CN102372670A (en) * | 2010-08-20 | 2012-03-14 | 清华大学 | Arylamine compounds containing arylpyridine groups and application of arylamine compounds containing arylpyridine group |
| CN103435616B (en) * | 2013-08-12 | 2015-10-07 | 湘潭大学 | A kind of D (A-Ar) ntype compound and application thereof |
| CN105481906A (en) * | 2016-01-22 | 2016-04-13 | 湘潭大学 | Arylamine tetradentate cyclometalated platinum complex near-infrared electroluminescent materials as well as preparation and application thereof |
| CN106008608A (en) * | 2016-05-24 | 2016-10-12 | 湘潭大学 | Asymmetric dual-core cyclometalated platinum (II) complex with D-A-A configuration pi conjugated system and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US7166368B2 (en) * | 2001-11-07 | 2007-01-23 | E. I. Du Pont De Nemours And Company | Electroluminescent platinum compounds and devices made with such compounds |
| EP1566385B1 (en) * | 2002-11-26 | 2009-03-11 | Semiconductor Energy Laboratory Co., Ltd. | Phosphorescent compound and electroluminescent element including the same |
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2005
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102372670A (en) * | 2010-08-20 | 2012-03-14 | 清华大学 | Arylamine compounds containing arylpyridine groups and application of arylamine compounds containing arylpyridine group |
| CN102372670B (en) * | 2010-08-20 | 2014-02-26 | 清华大学 | Arylamine compounds containing arylpyridine groups and application of arylamine compounds containing arylpyridine group |
| CN103435616B (en) * | 2013-08-12 | 2015-10-07 | 湘潭大学 | A kind of D (A-Ar) ntype compound and application thereof |
| CN105481906A (en) * | 2016-01-22 | 2016-04-13 | 湘潭大学 | Arylamine tetradentate cyclometalated platinum complex near-infrared electroluminescent materials as well as preparation and application thereof |
| CN105481906B (en) * | 2016-01-22 | 2018-06-12 | 湘潭大学 | A kind of four ring gear metal platinum complex near-infrared electroluminescent material of arylamine class and its preparation and application |
| CN106008608A (en) * | 2016-05-24 | 2016-10-12 | 湘潭大学 | Asymmetric dual-core cyclometalated platinum (II) complex with D-A-A configuration pi conjugated system and application thereof |
| CN106008608B (en) * | 2016-05-24 | 2019-01-11 | 湘潭大学 | It is a kind of with asymmetric double-nuclear ring metal platinum (II) complex of the pi-conjugated system of D-A-A configuration and its application |
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| CN1322094C (en) | 2007-06-20 |
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