CN103333158A - N-phenylcarbazole derivative and application thereof to electrophosphorescent device - Google Patents
N-phenylcarbazole derivative and application thereof to electrophosphorescent device Download PDFInfo
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- CN103333158A CN103333158A CN2013103138288A CN201310313828A CN103333158A CN 103333158 A CN103333158 A CN 103333158A CN 2013103138288 A CN2013103138288 A CN 2013103138288A CN 201310313828 A CN201310313828 A CN 201310313828A CN 103333158 A CN103333158 A CN 103333158A
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Abstract
The invention discloses the N- phenyl carbazole derivative with formula and its applications in electro phosphorescent device:
Wherein, A is not comprising any group, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, pyridine/pyrazine base; R1, R2 are hydrogen, diphenylphosphine oxygroup, cyano, 3- pyridyl group, 4- pyridyl group, 2- dibenzothiophenes/furyl, 4- dibenzothiophenes/furyl. N- phenyl carbazole derivative of the invention, effectively reduce the conjugation degree of material of main part, increase compound molecular weight, the doublet energy level and glass transition temperature for making material have all obtained a degree of raising, its polarity can be adjusted by push/pull electron group, compared with common phosphorescent light body material, phosphorescent OLED device performance has obtained effective raising, can be widely applied to field of organic electroluminescence.
Description
Technical field
The invention belongs to photoelectric material and applied technical field, relating to the N-phenyl carbazole is basic structural unit, connects with the derivative of modifying different characteristic electron groups and as the application of blue phosphorescent material of main part in organic electro phosphorescent device by position between the carbazole phenyl ring.
Background technology
Organic electroluminescent is a kind of selfluminous element, by between pair of electrodes, clipping luminescent layer and applying voltage, be compounded to form the molecule exciton from negative electrode (first electrode) injected electrons and anode (second electrode) injected holes at luminescence center, and this molecule exciton releases energy when getting back to ground state luminous.Organic electroluminescence device has characteristics such as voltage is low, brightness is high, the visual angle is wide, response is fast, thermal adaptability is good, is widely used in electronic product indicating meters such as televisor, mobile phone, MP3.
Electroluminescent organic material generally is divided into singlet fluorescence dye and two wires attitude phosphorescent coloring, but such material has stronger concentration quenching effect, can reduce the luminous efficiency of luminescent layer, causes the organic luminescent device performance lower.Therefore, adopt the Subjective and Objective structure in the present organic electroluminescence device mostly, soon fluorescence dye or phosphorescent coloring in main substance, to avoid burying in oblivion of concentration quenching and doublet-doublet, improve device performance with certain doped in concentrations profiled.Nowadays, prior art discloses the multiple material as material of main part.(M.A.Baldo such as Forrest in 1999 and Thompson, S.Lamansky, P.E.Burroes, M.E.Thompson, S.R.Forrest.Appl.Phys.Lett., 1999,75,4) with green phosphorescent material Ir (ppy) 3 with the doped in concentrations profiled of 6wt% 4,4 '-N, in the material of main part of N '-two carbazoles-biphenyl (CBP), the maximum external quantum efficiency of the green glow OLED of acquisition reaches 10%.But the double excited energy of CBP has only 2.56eV, if the blue phosphorescent material that mixes and to have high doublet excitation energy, energy can take place return phenomenon to main body, makes the external quantum efficiency of device drop to 5.7%.In order further to improve the efficient of blue phosphorescent device, must use the material of main part of high doublet energy, so Forrest(Holmes in 2003, R.J.Forrest, S.R.Tung, Y.-J.Kwong, R.C.and Brown, J.J.Garon, S.Thompson, M.E., Appl Phys Let, 2003,82,2422) develop and N, N '-two carbazyl-3,5-substituted benzene (mCP), this material are that the conjugated system with CBP dwindles, the doublet energy rises to 2.9eV, and external quantum efficiency is promoted to 7.8%.But the second-order transition temperature of mCP is lower, and the stability of material own is not high, has hindered its widespread use.
Summary of the invention
In view of this, the object of the present invention is to provide a class to have the blue phosphorescent material of main part N-phenyl carbazole derivative of high doublet energy and second-order transition temperature, and comprise the good stability, luminous intensity height of described material of main part, the organic electro phosphorescent device that current efficiency is high.
For achieving the above object, the invention provides following technical scheme:
N-phenyl carbazole derivative of the present invention has the structure shown in the following formula I:
Wherein, A is not for comprising any group, replacement or unsubstituted phenylene, replacement or unsubstituted biphenylene, pyridine/pyrazine base;
R
1Be hydrogen, diphenylphosphine oxygen base, cyano group, 3-pyridyl, 4-pyridyl, 2-dibenzothiophene/furyl, 4-dibenzothiophene/furyl;
R
2Be hydrogen, diphenylphosphine oxygen base, cyano group, 3-pyridyl, 4-pyridyl, 2-dibenzothiophene/furyl, 4-dibenzothiophene/furyl.
In the technique scheme, when A when not comprising any group, described derivative has the structure of formula (I-A), called after BCz.
In the technique scheme, when A was replacement or unsubstituted phenylene, described derivative had the structure of formula (I-B), called after PBCz.
Wherein, X is hydrogen, halogen, diphenylphosphine oxygen base, cyano group, 3-pyridyl, 4-pyridyl, 2-dibenzothiophene/furyl, 4-dibenzothiophene/furyl.
In the technique scheme, when A for replacing or when not replacing biphenylene, described derivative has the structure of formula (I-C), called after BPBCz.
Wherein, X
1, X
2Be hydrogen, halogen, diphenylphosphine oxygen base, cyano group, 3-pyridyl, 4-pyridyl, 2-dibenzothiophene/furyl, 4-dibenzothiophene/furyl, X
1, X
2Can be the same or different.
In the technique scheme, when A was pyridyl, described derivative had formula (I-D) or structure (I-E), respectively called after 35PydBCz and 26PydBCz.
In the technique scheme, when A was pyrazinyl, described derivative had the structure of formula (I-F), called after PyzBCz.
The present invention also provides a kind of organic electro phosphorescent device that comprises described N-phenyl carbazole derivative host material, comprise glass, be attached to Conducting Glass layer on glass, the hole injection layer that closes with the Conducting Glass laminating, hole transmission layer with the hole injection layer applying, luminescent layer with the hole transmission layer applying, hole blocking layer with the luminescent layer applying, electron transfer layer with the hole blocking layer applying, cathode layer with the electron transfer layer applying, described luminescent layer is made up of material of main part and dopant material, described material of main part is the derivative of the described structure of formula (1), and described dopant material is the complex of iridium with cyclic metal complexes.
Preferably, described complex of iridium is Ir (ppy) 3, the Ir (ppy) 2 (acac) of green light or the FIrpic of blue light-emitting.
Further, the doping ratio of Ir (ppy) 3 is 9wt%.
Further, the doping ratio of Ir (ppy) 2 (acac) is 8wt%.
Further, the doping ratio of FIrpic is 15wt%.
Material of main part of the present invention is applied in the organic electro phosphorescent device, can obtain electroluminescent properties efficiently.The present invention is the organic electro phosphorescent device of object preparation with FIrpic, and maximum luminous efficiency can reach every ampere of 44.0 Kan Tela, and maximum power efficiency reaches every watt of 40.1 lumen, is that performance is best in the similar device.Be the blue light object with FIrpic simultaneously, PO-01 is the organic electro phosphorescent device of gold-tinted object, and maximum luminous efficiency can reach every ampere of 56.5 Kan Tela, and maximum power efficiency reaches every watt of 54.0 lumen.
The present invention is structural unit with the N-phenyl carbazole, by the connection and the group of modifying different characteristic electrons of position between phenyl on the carbazole ring, obtain N-phenyl carbazole derivative, dwindle the conjugation degree of material of main part effectively, increase the compound effective molecular weight, make the doublet energy level of material and second-order transition temperature all obtain raising to a certain degree.In addition the polarity of N-phenyl carbazole derivative can by push away/drawing electron group adjusted, and compares with phosphorescent light body material commonly used, the phosphorescent OLED device performance has obtained effective raising, can be widely used in the organic electroluminescent field.
Description of drawings
In order to be illustrated more clearly in the technical scheme in the embodiment of the invention, the accompanying drawing of required use is done to introduce simply in will describing embodiment below, apparently, accompanying drawing relevant of the present invention in describing below only is some embodiments of the present invention, for those of ordinary skills, under the prerequisite of not paying creative work, can also obtain other accompanying drawing according to these accompanying drawings.
Fig. 1 is the uv-visible absorption spectra figure of the material of main part of the embodiment of the invention 1 preparation;
Fig. 2 is the photoluminescence figure of the material of main part of the embodiment of the invention 1 preparation;
Fig. 3 is electroluminescent device structural representation of the present invention;
Fig. 4 is the emmission spectrum figure of electroluminescent device of the present invention.
Embodiment
Below in conjunction with the accompanying drawing in the embodiment of the invention, the technical scheme in the embodiment of the invention is described in detail, obviously, described embodiment only is the present invention's part embodiment, rather than whole embodiment.Based on the embodiment among the present invention, the every other embodiment that those of ordinary skills obtain under the prerequisite of not making creative work belongs to the scope of protection of the invention.
Step 1: 4.00 gram 3,6-dibromo carbazoles and 3.20 gram N-phenyl carbazole-3-boric acid are added in 50 ml flasks, add catalyst P d (PPh
3)
4650 milligrams, 42 milliliters of tetrahydrofuran (THF)s, 2M K
2CO
314 milliliters of solution, argon shield refluxed 24 hours, cooling back dichloromethane extraction; organic layer is spin-dried for after with anhydrous sodium sulfate drying, with methylene dichloride/sherwood oil=1:5(volume ratio) cross post, be spin-dried for 4.70 gram 6-bromo-N; N-phenylbenzene-3,3 '-duplex carbazole, productive rate 83.7%.
Step 2: with 4.0 gram 6-bromo-N, N-phenylbenzene-3,3 '-duplex carbazole and 4.0 gram cuprous cyanides add in 50 ml flasks; add N; 30 milliliters of dinethylformamides, argon shield refluxed 24 hours, cooling back dichloromethane extraction; organic layer is spin-dried for after with anhydrous sodium sulfate drying; with methylene dichloride/sherwood oil=1:5(volume ratio) cross post, be spin-dried for 2.91 gram 6-cyano group-N, N-phenylbenzene-3; 3 '-duplex carbazole (BCzCN), productive rate 80.5%.
Step 1: 4.00 gram 3-bromine carbazoles and 3.20 gram N-phenyl carbazole-3-boric acid are added in 50 ml flasks, add catalyst P d (PPh
3)
4650 milligrams, 42 milliliters of tetrahydrofuran (THF)s, 2M K
2CO
314 milliliters of solution, argon shield refluxed 24 hours, cooling back dichloromethane extraction; organic layer is spin-dried for after with anhydrous sodium sulfate drying, with methylene dichloride/sherwood oil=1:5(volume ratio) cross post, be spin-dried for 5.33 gram N; N-phenylbenzene-3,3 '-duplex carbazole, productive rate 88.6%.
Step 2: with 4.00 gram N, N-phenylbenzene-3,3 '-duplex carbazole and 30 milliliters of N, dinethylformamide adds in 50 ml flasks, and ice bath is cooled to about 0 ℃, adds 4.00 grams 1 in batches, 3-two bromo-5, the 5-dimethyl hydantion keeps temperature to react 8 hours below 5 ℃.Reaction mixture is poured in the water, used dichloromethane extraction, washing, saturated common salt washing, with being spin-dried for behind the anhydrous sodium sulfate drying, with methylene dichloride/sherwood oil=1:5(volume ratio) cross post, be spin-dried for 4.25 grams, 6,6 '-two bromo-N, N-phenylbenzene-3,3 '-duplex carbazole, productive rate 67.3%.
Step 3: with 4.0 grams, 6,6 '-two bromo-N, N-phenylbenzene-3; 3 '-duplex carbazole and 4.0 gram cuprous cyanides add in 50 ml flasks, add N, 30 milliliters of dinethylformamides; argon shield refluxed 24 hours, and cooling back dichloromethane extraction, organic layer are spin-dried for after with anhydrous sodium sulfate drying; with methylene dichloride/sherwood oil=1:5(volume ratio) the mistake post; be spin-dried for 1.84 the gram 6,6 '-dicyano-N, N-phenylbenzene-3; 3 '-duplex carbazole (BCzDCN), productive rate 55.3%.
Step 1: 4.00 gram 1,3-dibromobenzenes and 3.20 gram N-phenyl carbazole-3-boric acid are added in 50 ml flasks, add catalyst P d (PPh
3)
4650 milligrams, 42 milliliters of tetrahydrofuran (THF)s, 2M K
2CO
314 milliliters of solution, argon shield refluxed 24 hours, cooling back dichloromethane extraction; organic layer is spin-dried for after with anhydrous sodium sulfate drying, with methylene dichloride/sherwood oil=1:5(volume ratio) cross post, be spin-dried for 7.44 grams 1; 3-two (N-phenyl carbazole-3-yl) benzene, productive rate 78.3%.
Step 2: with 4.00 gram 1,3-two (N-phenyl carbazole-3-yl) benzene and 30 milliliters of N, dinethylformamide adds in 50 ml flasks, ice bath is cooled to about 0 ℃, adds 4.00 grams, 1,3-, two bromo-5 in batches, the 5-dimethyl hydantion keeps temperature to react 8 hours below 0 ℃.Reaction mixture is poured in the water, use dichloromethane extraction, washing, the saturated common salt washing, with being spin-dried for behind the anhydrous sodium sulfate drying, with methylene dichloride/sherwood oil=1:5(volume ratio) cross post, be spin-dried for 2.84 gram 3-bromo-N-phenyl-6-[3-(N-phenyl carbazole-3-yl) phenyl] carbazole, productive rate 62.3%.
Step 3: with 4.0 gram 3-bromo-N-phenyl-6-[3-(N-phenyl carbazole-3-yl) phenyl] carbazole and 4.0 gram cuprous cyanides add in 50 ml flasks; add N; 30 milliliters of dinethylformamides; argon shield refluxed 24 hours; cooling back dichloromethane extraction; organic layer is spin-dried for after with anhydrous sodium sulfate drying; with methylene dichloride/sherwood oil=1:5(volume ratio) the mistake post; be spin-dried for 2.28 gram 3-cyano group-N-phenyl-6-[3-(N-phenyl carbazole-3-yl) phenyl] carbazole (PBCzCN), productive rate 62.3%.
Step 1: be same as embodiment 3 step 1.
Step 2: be same as embodiment 3 step 2.
Step 3: with 4.00 gram 3-bromo-N-phenyl-6-[3-(N-phenyl carbazole-3-yl) phenyl] carbazole and 3.20 gram dibenzothiophene-4-boric acid add in 50 ml flasks, add catalyst P d (PPh
3)
4650 milligrams, 42 milliliters of tetrahydrofuran (THF)s, 2M K
2CO
314 milliliters of solution; argon shield refluxed 24 hours; cooling back dichloromethane extraction; organic layer is spin-dried for after with anhydrous sodium sulfate drying; with methylene dichloride/sherwood oil=1:5(volume ratio) the mistake post; be spin-dried for 3.63 gram 3-(4-dibenzothiophene bases)-N-phenyl-6-[3-(N-phenyl carbazole-3-yl) phenyl] carbazole (PBCzDBT4), productive rate 78.2%.
Step 1: bromo-iodobenzene between 4.00 grams and 3.20 gram 3-bromobenzene boric acid are added in 50 ml flasks, add catalyst P d (PPh
3)
4650 milligrams, 42 milliliters of tetrahydrofuran (THF)s, 2M K
2CO
314 milliliters of solution, argon shield refluxed 24 hours, and cooling back dichloromethane extraction, organic layer are spin-dried for after with anhydrous sodium sulfate drying, with methylene dichloride/sherwood oil=1:5(volume ratio) cross post, be spin-dried for to such an extent that 3.85 restrain 3,3 '-'-dibromobiphenyl, productive rate 87.9%.
Step 2: with 4.00 grams 3,3 '-'-dibromobiphenyl and 3.20 gram N-phenyl carbazole-3-boric acid add in 50 ml flasks, add catalyst P d (PPh
3)
4650 milligrams, 42 milliliters of tetrahydrofuran (THF)s, 2M K
2CO
314 milliliters of solution; argon shield refluxed 24 hours; cooling back dichloromethane extraction; organic layer is spin-dried for after with anhydrous sodium sulfate drying; with methylene dichloride/sherwood oil=1:5(volume ratio) the mistake post; be spin-dried for 6.41 the gram 3,3 '-two (N-phenyl carbazole-3-yl) biphenyl (BPBCz), productive rate 78.6%.
Step 1: be same as embodiment 4 step 1.
Step 2: be same as embodiment 4 step 2.
Step 3: be same as embodiment 2 step 2, just with raw material N, N-phenylbenzene-3,3 '-duplex carbazole changes 3 into, 3 '-two (N-phenyl carbazole-3-yl) biphenyl, be spin-dried for 3.25 gram off-white color solid product 3-bromo-N-phenyl-6[3 '-(N-phenyl carbazole-3-yl) biphenyl 3-yls] carbazole, productive rate 72.7%.
Step 4: be same as embodiment 2 step 3, just with raw material 6,6 '-two bromo-N, N-phenylbenzene-3,3 '-duplex carbazole changes 3 into, 3 '-two (N-phenyl carbazole-3-yl) biphenyl, be spin-dried for 2.17 gram off-white color solid product 3-cyano group-N-phenyl-6[3 '-(N-phenyl carbazole-3-yl) biphenyl 3-yls] carbazole (BPBCzCN), productive rate 58.6%.
Step 1: be same as embodiment 3 step 1, just with raw material 1, the 3-dibromobenzene changes 3,5-dibromo pyridine into, gets off-white color solid product 1,3-two (N-phenyl carbazole-3-yl) pyridine.
Step 2: be same as embodiment 3 step 2, just with raw material 1,3-two (N-phenyl carbazole-3-yl) benzene changes 3,5-two (N-phenyl carbazole-3-yl) pyridine into, gets off-white color solid product 3-bromo-N-phenyl-6-[5-(N-phenyl carbazole-3-yl) pyridin-3-yl] carbazole.
Step 3: with 4.00 gram 3-bromo-N-phenyl-6-[5-(N-phenyl carbazole-3-yl) pyridin-3-yls] carbazole and 3.20 gram pyridine-3-boric acid add in 50 ml flasks, add catalyst P d (PPh
3)
4650 milligrams, 42 milliliters of tetrahydrofuran (THF)s, 2M K
2CO
314 milliliters of solution; argon shield refluxed 24 hours; cooling back dichloromethane extraction; organic layer is spin-dried for after with anhydrous sodium sulfate drying; with methylene dichloride/sherwood oil=1:5(volume ratio) the mistake post; be spin-dried for 3.80 gram N-phenyl-3-[5-(N-phenyl carbazole-3-yls) pyridin-3-yl]-the 6-(pyridin-3-yl) carbazole (PBCz3Py), productive rate 95.3%.
Be the Application Example of The compounds of this invention below:
The preferred implementation of fabricate devices:
As shown in Figure 3, the typical structure of OLED device is: substrate 1/ anode/hole injection layer (HIL) 2/ hole transmission layer (HTL) 3/ electronic barrier layer (EBL) 4/ organic luminous layer (EML) 5/ hole blocking layer (HBL) 6/ electron transfer layer (ETL) 7/ electron injecting layer (EIL) 8/ negative electrode 9.
Substrate adopts the ITO transparent conducting glass substrate, and hole injection layer can adopt molybdic oxide (MoO
3) or 2,3,6,7,10,11-, six cyano group-1,4,5,8,9,12-six azepine triphenylenes (HAT-CN), hole transmission layer can adopt NPB, CBP or TAPC, and electron transfer layer can adopt TPBi, Bphen or TmPyPB, device architecture can also can be multi-luminescent layer for the single-shot photosphere, and every layer luminous can also can be many doped structures for single doped structure.Glow color is not limit, can be as red, yellow, blue, green, white etc., and phosphorescent coloring is selected FIrpic, Ir (ppy) 3, Ir (ppy) 2 (acac), PO-01, Ir (piq), Ir (MDQ) 2 (acac) etc. for use.Negative electrode can adopt metal and composition thereof structure, as Mg:Al, Li:Al etc., also can be electron injecting layer/metal-layer structure, as the common cathode construction of LiF/Al, Liq/Al, wherein electron injecting layer can be simple substance, compound or the mixture etc. of basic metal, alkaline-earth metal, transition metal.Selected in the present invention cathode material is Liq/Al.
Adopt compd B CzCN of the present invention as OLED device main body material, FIrpic is the blue phosphorescent dyestuff, device architecture is: and ITO/HAT-CN (10nm)/TAPC (45nm)/BCzCN:FIrpic (19nm, 8vol%doping)/TmPyPB (40nm)/Liq (2nm)/Al (120nm).
The device preparation process is as follows: with ITO transparent conducting glass substrate supersound process in commercial clean-out system, in deionized water, wash, clean repeatedly three times with deionized water, acetone, ethanol, under the environment of cleaning, be baked to and go out moisture fully, with ultraviolet lamp and ozonize ITO conductive glass.The ITO conductive glass of handling is placed in the vacuum chamber, be evacuated to 3.0 * 10
-4～4.0 * 10
-4Pa, vacuum evaporation HAT-CN is as hole injection layer (HIL) on the ITO conductive glass, and evaporation speed is
Coating film thickness is 10nm; Vacuum evaporation TAPC is as hole transmission layer (HTL) and electronic barrier layer (EBL) on hole injection layer, and evaporation speed is
Coating film thickness is 45nm; Adopting the processing method of double source evaporation then, is material of main part with The compounds of this invention BCzCN, adopts FIrpic as first organic luminous layer (EML) of dyestuff, and control evaporation speed is
Coating film thickness is 20nm, and the doping content of FIrpic is 8%.Vacuum evaporation one deck TmPyPB is as hole blocking layer (HBL) and the electron transfer layer (ETL) of device on organic luminous layer, and evaporation speed is
Coating film thickness is 40nm; Vacuum evaporation Liq and Al layer are as device cathodes on electron transfer layer, and thickness is 120nm.
Adopt compd B CzCN of the present invention as OLED device main body material, Ir (ppy) 2 (acac) is green phosphorescent dye, and device architecture is: ITO/CBP:MoO
3(35nm, 6vol%doping)/CBP (15nm)/BCzCN:Ir (ppy) 2 (acac) (15nm, 8vol%doping)/TmPyPB (65nm)/Liq (2nm)/Al (120nm).
The device preparation process is as follows: with ITO transparent conducting glass substrate supersound process in commercial clean-out system, in deionized water, wash, clean repeatedly three times with deionized water, acetone, ethanol, under the environment of cleaning, be baked to and go out moisture fully, with ultraviolet lamp and ozonize ITO conductive glass.The ITO conductive glass of handling is placed in the vacuum chamber, be evacuated to 30 * 10
-4～40 * 10
-4Pa is with processing method vacuum evaporation CBP doping MoO on the ITO conductive glass of double source evaporation
3Layer is as hole injection layer (HIL) and hole transmission layer (HTL), and evaporation speed is
Coating film thickness is 35nm, MoO
3Doping content be 15%; Vacuum evaporation CBP is as electronic barrier layer (EBL) on hole transmission layer, and evaporation speed is
Coating film thickness is 15nm; Adopting the processing method of double source evaporation then, is material of main part with The compounds of this invention BCzCN, adopts Ir (ppy) 2 (acac) as the organic luminous layer (EML) of dyestuff, and control evaporation speed is
Coating film thickness is 15nm, and the doping content of Ir (ppy) 2 (acac) is 8%; Vacuum evaporation one deck TmPyPB is as hole blocking layer (HBL) and the electron transfer layer (ETL) of device on organic luminous layer, and evaporation speed is
Coating film thickness is 65nm; Vacuum evaporation Liq and Al layer are as device cathodes on electron transfer layer, and thickness is 120nm.
Embodiment 10
Adopt compd B CzCN of the present invention as OLED device main body material, FIrpic is the blue phosphorescent dyestuff, PO-01 is the yellow phosphorescence dyestuff, device architecture is: ITO/HAT-CN (10nm)/TAPC (45nm)/BCzCN:FIrpic (19nm, 8vol%doping)/and BCzCN:PO-01 (1nm, 6vol%doping)/TmPyP B (40nm)/Liq (2nm)/Al (120nm).
The device preparation process is as follows: with ITO transparent conducting glass substrate supersound process in commercial clean-out system, in deionized water, wash, clean repeatedly three times with deionized water, acetone, ethanol, under the environment of cleaning, be baked to and go out moisture fully, with ultraviolet lamp and ozonize ITO conductive glass.The ITO conductive glass of handling is placed in the vacuum chamber, be evacuated to 3.0 * 10
-4～4.0 * 10
-4Pa, vacuum evaporation HAT-CN is as hole injection layer (HIL) on the ITO conductive glass, and evaporation speed is
Coating film thickness is 10nm; Vacuum evaporation TAPC is as hole transmission layer (HTL) and electronic barrier layer (EBL) on hole injection layer, and evaporation speed is
Coating film thickness is 45nm; Adopting the processing method of double source evaporation then, is material of main part with The compounds of this invention BCzCN, adopts FIrpic as first organic luminous layer (EML) of dyestuff, and control evaporation speed is
Coating film thickness is 20nm, and the doping content of FIrpic is 8%; And then be material of main part with The compounds of this invention BCzCN equally, adopt PO-01 as second organic luminous layer (EML) of dyestuff, control evaporation speed is
Coating film thickness is 1nm, and the doping content of PO-01 is 6%; Vacuum evaporation one deck TmPyPB is as hole blocking layer (HBL) and the electron transfer layer (ETL) of device on second organic luminous layer, and evaporation speed is
Coating film thickness is 40nm; Vacuum evaporation Liq and Al layer are as device cathodes on electron transfer layer, and thickness is 120nm.
Embodiment 11
Adopt compd B PBCz of the present invention as OLED device main body material, FIrpic is the blue phosphorescent dyestuff, device architecture is: and ITO/HAT-CN (10nm)/TAPC (45nm)/BPBCz:FIrpic (20nm, 8vol%doping)/TmPyPB (40nm)/Liq (2nm)/Al (120nm).
The device preparation process is as follows: with ITO transparent conducting glass substrate supersound process in commercial clean-out system, in deionized water, wash, clean repeatedly three times with deionized water, acetone, ethanol, under the environment of cleaning, be baked to and go out moisture fully, with ultraviolet lamp and ozonize ITO conductive glass.The ITO conductive glass of handling is placed in the vacuum chamber, be evacuated to 3.0 * 10
-4～4.0 * 10
-4Pa, vacuum evaporation HAT-CN is as hole injection layer (HIL) on the ITO conductive glass, and evaporation speed is
Coating film thickness is 10nm; Vacuum evaporation TAPC is as hole transmission layer (HTL) and electronic barrier layer (EBL) on hole injection layer, and evaporation speed is
Coating film thickness is 45nm; Adopting the processing method of double source evaporation then, is material of main part with The compounds of this invention BPBCz, adopts FIrpic as the organic luminous layer (EML) of dyestuff, and control evaporation speed is
Coating film thickness is 20nm, and the doping content of FIrpic is 8%; Vacuum evaporation one deck TmPyPB is as hole blocking layer (HBL) and the electron transfer layer (ETL) of device on organic luminous layer, and evaporation speed is
Coating film thickness is 40nm; Vacuum evaporation Liq and Al layer are as device cathodes on electron transfer layer, and thickness is 120nm.
Embodiment 12
Adopt compd B PBCz of the present invention as OLED device main body material, FIrpic is the blue phosphorescent dyestuff, PO-01 is the yellow phosphorescence dyestuff, device architecture is: ITO/HAT-CN (10nm)/TAPC (45nm)/BPBCz:FIrpic (19nm, 8vol%doping)/and BPBCz:PO-01 (1nm, 6vol%doping)/TmPyPB (40nm)/Liq (2nm)/Al (120nm).
The device preparation process is as follows: with ITO transparent conducting glass substrate supersound process in commercial clean-out system, in deionized water, wash, clean repeatedly three times with deionized water, acetone, ethanol, under the environment of cleaning, be baked to and go out moisture fully, with ultraviolet lamp and ozonize ITO conductive glass.The ITO conductive glass of handling is placed in the vacuum chamber, be evacuated to 3.0 * 10
-4～4.0 * 10
-4Pa, vacuum evaporation HAT-CN is as hole injection layer (HIL) on the ITO conductive glass, and evaporation speed is
Coating film thickness is 10nm; Vacuum evaporation TAPC is as hole transmission layer (HTL) and electronic barrier layer (EBL) on hole injection layer, and evaporation speed is
Coating film thickness is 45nm; Adopting the processing method of double source evaporation then, is material of main part with The compounds of this invention BPBCz, adopts FIrpic as first organic luminous layer (EML) of dyestuff, and control evaporation speed is
Coating film thickness is 20nm, and the doping content of FIrpic is 8%; And then be material of main part with The compounds of this invention BPBCz equally, adopt PO-01 as second organic luminous layer (EML) of dyestuff, control evaporation speed is
Coating film thickness is 1nm, and the doping content of PO-01 is 6%; Vacuum evaporation one deck TmPyPB is as hole blocking layer (HBL) and the electron transfer layer (ETL) of device on second organic luminous layer, and evaporation speed is
Coating film thickness is 40nm; Vacuum evaporation Liq and Al layer are as device cathodes on electron transfer layer, and thickness is 120nm.
Embodiment 13
Adopt compound 35PydCz of the present invention as OLED device main body material, FIrpic is the blue phosphorescent dyestuff, device architecture is: and ITO/HAT-CN (10nm)/TAPC (45nm)/35PydCz:FIrpic (20nm, 8vol%doping)/TmPyPB (40nm)/Liq (2nm)/Al (120nm).
The device preparation process is as follows: with ITO transparent conducting glass substrate supersound process in commercial clean-out system, in deionized water, wash, clean repeatedly three times with deionized water, acetone, ethanol, under the environment of cleaning, be baked to and go out moisture fully, with ultraviolet lamp and ozonize ITO conductive glass.The ITO conductive glass of handling is placed in the vacuum chamber, be evacuated to 3.0 * 10
-4～4.0 * 10
-4Pa, vacuum evaporation HAT-CN is as hole injection layer (HIL) on the ITO conductive glass, and evaporation speed is
Coating film thickness is 10nm; Vacuum evaporation TAPC is as hole transmission layer (HTL) and electronic barrier layer (EBL) on hole injection layer, and evaporation speed is
Coating film thickness is 45nm; Adopting the processing method of double source evaporation then, is material of main part with The compounds of this invention 35PydCz, adopts FIrpic as the organic luminous layer (EML) of dyestuff, and control evaporation speed is
Coating film thickness is 20nm, and the doping content of FIrpic is 8%; Vacuum evaporation one deck TmPyPB is as hole blocking layer (HBL) and the electron transfer layer (ETL) of device on organic luminous layer, and evaporation speed is
Coating film thickness is 40nm; Vacuum evaporation Liq and Al layer are as device cathodes on electron transfer layer, and thickness is 120nm.
Embodiment 14
Adopt compound 26PydCz of the present invention as OLED device hole, electron transport material and material of main part, Ir (ppy) 2 (acac) is green phosphorescent dye, the OLED device of preparation individual layer, and device architecture is: ITO/MoO
3(5nm)/and 26PydCz (45nm)/26PydCz:Ir (ppy) 2 (acac) (30nm, 8vol%doping)/26P ydCz (25nm)/Liq (2nm)/Al (120nm).
The device preparation process is as follows: with ITO transparent conducting glass substrate supersound process in commercial clean-out system, in deionized water, wash, clean repeatedly three times with deionized water, acetone, ethanol, under the environment of cleaning, be baked to and go out moisture fully, with ultraviolet lamp and ozonize ITO conductive glass.The ITO conductive glass of handling is placed in the vacuum chamber, be evacuated to 3.0 * 10
-4～4.0 * 10
-4Pa, vacuum evaporation MoO on the ITO conductive glass
3As hole injection layer (HIL), evaporation speed is
Coating film thickness is 5nm; Vacuum evaporation 26PydCz is as hole transmission layer (HTL) on hole injection layer, and evaporation speed is
Coating film thickness is 45nm; Adopting the processing method of double source evaporation then, is material of main part with The compounds of this invention 26PydCz, adopts Ir (ppy) 2 (acac) as the organic luminous layer (EML) of dyestuff, and control evaporation speed is
Coating film thickness is 30nm, and the doping content of Ir (ppy) 2 (acac) is 8%; Vacuum evaporation one deck 26PydCz is as the electron transfer layer (ETL) of device on organic luminous layer, and evaporation speed is
Coating film thickness is 25nm; Vacuum evaporation Liq and Al layer are as device cathodes on electron transfer layer, and thickness is 120nm.
Embodiment 15
Adopt compound 35PydCz of the present invention as OLED device hole, electron transport material and material of main part, FIrpic is the blue light photoinitiator dye, the OLED device of preparation individual layer, and device architecture is: ITO/MoO
3(5nm)/and 35PydCz (45nm)/35PydCz:FIrpic (30nm, 8vol%doping)/35PydCz (25nm)/Liq (2nm)/Al (120nm).
The device preparation process is as follows: with ITO transparent conducting glass substrate supersound process in commercial clean-out system, in deionized water, wash, clean repeatedly three times with deionized water, acetone, ethanol, under the environment of cleaning, be baked to and go out moisture fully, with ultraviolet lamp and ozonize ITO conductive glass.The ITO conductive glass of handling is placed in the vacuum chamber, be evacuated to 3.0 * 10
-4～4.0 * 10
-4Pa, vacuum evaporation MoO on the ITO conductive glass
3As hole injection layer (HIL), evaporation speed is
Coating film thickness is 5nm; Vacuum evaporation 35PydCz is as hole transmission layer (HTL) on hole injection layer, and evaporation speed is
Coating film thickness is 45nm; Adopting the processing method of double source evaporation then, is material of main part with The compounds of this invention 35PydCz, adopts FIrpic as the organic luminous layer (EML) of dyestuff, and control evaporation speed is
Coating film thickness is 30nm, and the doping content of FIrpic is 8%; Vacuum evaporation one deck 35PydCz is as the electron transfer layer (ETL) of device on organic luminous layer, and evaporation speed is
Coating film thickness is 25nm; Vacuum evaporation Liq and Al layer are as device cathodes on electron transfer layer, and thickness is 120nm.
Comparative example 1
Adopt compd B Cz of the present invention as OLED device main body material, FIrpic is the blue phosphorescent dyestuff, device architecture is: and ITO/HAT-CN (10nm)/TAPC (45nm)/BCz:FIrpic (20nm, 8vol%doping)/TmPyPB (40nm)/Liq (2nm)/Al (120nm).
The device preparation process is as follows: with ITO transparent conducting glass substrate supersound process in commercial clean-out system, in deionized water, wash, clean repeatedly three times with deionized water, acetone, ethanol, under the environment of cleaning, be baked to and go out moisture fully, with ultraviolet lamp and ozonize ITO conductive glass.The ITO conductive glass of handling is placed in the vacuum chamber, be evacuated to 3.0 * 10
-4～4.0 * 10
-4Pa, vacuum evaporation HAT-CN is as hole injection layer (HIL) on the ITO conductive glass, and evaporation speed is
Coating film thickness is 10nm; Vacuum evaporation TAPC is as hole transmission layer (HTL) and electronic barrier layer (EBL) on hole injection layer, and evaporation speed is
Coating film thickness is 45nm; Adopting the processing method of double source evaporation then, is material of main part with The compounds of this invention mCP, adopts FIrpic as the organic luminous layer (EML) of dyestuff, and control evaporation speed is
Coating film thickness is 20nm, and the doping content of FIrpic is 8%; Vacuum evaporation one deck TmPyPB is as hole blocking layer (HBL) and the electron transfer layer (ETL) of device on organic luminous layer, and evaporation speed is
Coating film thickness is 40nm; Vacuum evaporation Liq and Al layer are as device cathodes on electron transfer layer, and thickness is 120nm.
Comparative example 2
Adopt Compound P BCz of the present invention as OLED device hole, electron transport material and material of main part, Ir (ppy) 2 (acac) is green phosphorescent dye, the OLED device of preparation individual layer, and device architecture is: ITO/MoO
3(5nm)/and PBCz (45nm)/PBCz:Ir (ppy) 2 (acac) (30nm, 8vol%doping)/PBCz (25nm)/Liq (2nm)/Al (120nm).
The device preparation process is as follows: with ITO transparent conducting glass substrate supersound process in commercial clean-out system, in deionized water, wash, clean repeatedly three times with deionized water, acetone, ethanol, under the environment of cleaning, be baked to and go out moisture fully, with ultraviolet lamp and ozonize ITO conductive glass.The ITO conductive glass of handling is placed in the vacuum chamber, be evacuated to 3.0 * 10
-4～4.0 * 10
-4Pa, vacuum evaporation MoO on the ITO conductive glass
3As hole injection layer (HIL), evaporation speed is
Coating film thickness is 5nm; Vacuum evaporation PBCz is as hole transmission layer (HTL) on hole injection layer, and evaporation speed is
Coating film thickness is 45nm; Adopting the processing method of double source evaporation then, is material of main part with The compounds of this invention PBCz, adopts Ir (ppy) 2 (acac) as the organic luminous layer (EML) of dyestuff, and control evaporation speed is
Coating film thickness is 30nm, and the doping content of Ir (ppy) 2 (acac) is 8%; Vacuum evaporation one deck PBCz is as the electron transfer layer (ETL) of device on organic luminous layer, and evaporation speed is
Coating film thickness is 25nm; Vacuum evaporation Liq and Al layer are as device cathodes on electron transfer layer, and thickness is 120nm.
The device architecture of embodiment 8～15 and comparative example 1～2 sees Table 1:
Table 1 is with the device architecture of the Organic Light Emitting Diode of The compounds of this invention preparation
Electric current-the brightness of device-voltage characteristic is to be finished by the Keithley source measuring system (Keithley2400Sourcemeter, Keithley2000Currentmeter) that has corrected silicon photoelectric diode, electroluminescent spectrum is by the Photo research PR655 of company spectrometer measurement, and all measurements are all finished in atmosphere at room temperature.
The device data of embodiment 8～15 and comparative example 1～2 sees Table 2:
Table 2 is with the device data of the Organic Light Emitting Diode of The compounds of this invention preparation
As can be seen from the above table, adopt the device of The compounds of this invention to obtain result preferably with respect to the phosphorescence luminescent device that generally adopts mCP, CBP material of main part in the industry.Device one emission blue light, maximum current efficient is up to every ampere of 44.0 Kan Tela.Device three emission white light maximum current efficient are one of present this type of material of main part maximums up to every ampere of 62.0 Kan Tela.Device 5 corresponding green glow performances are especially well beyond comparative device.And the second-order transition temperature of all compounds is all more than 100 ℃, much larger than mCP(69 ℃) and CBP(62 ℃), being more suitable for industrialization, can be widely used in the higher OLED large-size screen monitors of brightness requirement are shown and the OLED white-light illuminating.
In sum, the present invention is structural unit with the N-phenyl carbazole, by the connection and the group of modifying different characteristic electrons of position between phenyl on the carbazole ring, obtain N-phenyl carbazole derivative, dwindle the conjugation degree of material of main part effectively, increase the compound effective molecular weight, make the doublet energy level of material and second-order transition temperature all obtain raising to a certain degree.In addition the polarity of N-phenyl carbazole derivative can by push away/drawing electron group adjusted, and compares with phosphorescent light body material commonly used, the phosphorescent OLED device performance has obtained effective raising, can be widely used in the organic electroluminescent field.
To those skilled in the art, obviously the invention is not restricted to the details of above-mentioned one exemplary embodiment, and under the situation that does not deviate from spirit of the present invention or essential characteristic, can realize the present invention with other specific form.Therefore, no matter from which point, all should regard embodiment as exemplary, and be nonrestrictive, scope of the present invention is limited by claims rather than above-mentioned explanation, therefore is intended to include in the present invention dropping on the implication that is equal to important document of claim and all changes in the scope.
In addition, be to be understood that, though this specification sheets is described according to embodiment, but be not that each embodiment only comprises an independently technical scheme, this narrating mode of specification sheets only is for clarity sake, those skilled in the art should make specification sheets as a whole, and the technical scheme among each embodiment also can form other embodiments that it will be appreciated by those skilled in the art that through appropriate combination.
Claims (8)
1. a class N-phenyl carbazole derivative is characterized in that having the structure shown in the formula I:
Wherein, A is not for comprising any group, replacement or unsubstituted phenylene, replacement or unsubstituted biphenylene, pyridine/pyrazine base;
R
1Be hydrogen, diphenylphosphine oxygen base, cyano group, 3-pyridyl, 4-pyridyl, 2-dibenzothiophene/furyl, 4-dibenzothiophene/furyl;
R
2Be hydrogen, diphenylphosphine oxygen base, cyano group, 3-pyridyl, 4-pyridyl, 2-dibenzothiophene/furyl, 4-dibenzothiophene/furyl.
2. N-phenyl carbazole derivative according to claim 1 is characterized in that, A is for replacing or unsubstituted phenylene, and described derivative has the structure of formula (II):
Wherein, X is hydrogen, halogen, diphenylphosphine oxygen base, cyano group, 3-pyridyl, 4-pyridyl, 2-dibenzothiophene/furyl, 4-dibenzothiophene/furyl.
3. N-phenyl carbazole derivative according to claim 1 is characterized in that, A is for replacing or not replacing biphenylene, and described derivative has the structure of formula (III):
Wherein, X
1, X
2Be hydrogen, halogen, diphenylphosphine oxygen base, cyano group, 3-pyridyl, 4-pyridyl, 2-dibenzothiophene/furyl, 4-dibenzothiophene/furyl, X
1, X
2Identical or different.
4. organic electro phosphorescent device, comprise glass, be attached to Conducting Glass layer on glass, the hole injection layer that closes with the Conducting Glass laminating, hole transmission layer with the hole injection layer applying, luminescent layer with the hole transmission layer applying, hole blocking layer with the luminescent layer applying, electron transfer layer with the hole blocking layer applying, cathode layer with the electron transfer layer applying, it is characterized in that: described luminescent layer is made up of material of main part and dopant material, described material of main part is the described N-phenyl carbazole of claim 1 derivative, and described dopant material is the complex of iridium with cyclic metal complexes.
5. organic electro phosphorescent device according to claim 4, it is characterized in that: described complex of iridium is Ir (ppy) 3, the Ir (ppy) 2 (acac) of green light or the FIrpic of blue light-emitting.
6. organic electro phosphorescent device according to claim 5, it is characterized in that: the doping ratio of Ir (ppy) 3 is 9wt%.
7. organic electro phosphorescent device according to claim 5, it is characterized in that: the doping ratio of Ir (ppy) 2 (acac) is 8wt%.
8. organic electro phosphorescent device according to claim 5, it is characterized in that: the doping ratio of FIrpic is 15wt%.
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