CN104370964A - Electron type phosphorus-oxygen derivative and electrophosphorescence luminescent device - Google Patents
Electron type phosphorus-oxygen derivative and electrophosphorescence luminescent device Download PDFInfo
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Abstract
The present invention discloses an electron type phosphorus-oxygen derivative and an electrophosphorescence luminescent device, wherein the electron type phosphorus-oxygen derivative adopts the triphenyl phosphorus oxygen group as the core, and the three benzene rings of the triphenyl phosphorus oxygen group are conjugated with different electron transport groups (R1, R2 and R3) through bonds so as to effectively solve the carrier balance, such that the electron type green light phosphorescence main body material with characteristics of high triplet state, high electron mobility and high thermal stability is obtained. In addition, the electrophosphorescence luminescent device selects the electron type phosphorus-oxygen derivative as the transmitting layer or the luminescence layer material of the components, such that the electrophosphorescence luminescent device has characteristics of high brightness, high efficiency and low roll-off.
Description
Technical field
The invention belongs to field of photoelectric technology, particularly a kind of electron type phosphorus oxygen derivative and electro-phosphorescent luminescent device.
Background technology
1987, Deng Qingyun professor and Vanslyke adopted ultrathin membrane technology nesa coating to make anode, and AlQ3 makes luminescent layer, triaryl amine makes hole transmission layer, and negative electrode made by Mg/Ag alloy, has made double-deck organic electroluminescence device (Appl.Phys.Lett., 1987,52,913).
Nineteen ninety, the OLED (Nature.1990,347,539) that it is luminescent layer that the people such as Burroughes have found with conjugated polymer PPV, has from then on started the upsurge of OLED research in worldwide.
Due to the impact of spin restriction, what we saw in daily life mostly is fluorescence phenomenon; Initial OLED technical study mainly concentrates on fluorescent device direction; But according to spin quantum statistical theory, the maximum internal quantum efficiency of fluorescence electroluminescent device only has 25%, and electrophosphorescence device, then can reach 100%.Therefore in 1999, (the Appl.Phys.Let. such as Forrest and Thompson, 1999,75,4.) by green glow phosphor material Ir (ppy) 3 with the doped in concentrations profiled of 6wt% at 4,4 '-N, in the material of main part of N '-two carbazoles-biphenyl (CBP), obtain the maximum external quantum efficiency of green glow OLED (EQE) and reach 8%, after breaching the theoretical limit of electrochromic fluorescent devices, people create phosphorescent light-emitting materials and show great attention to; Electromechanical phosphorescent material is the focus of research always since then.
And for organic semiconductor material, its electron transfer rate is slower than hole transport speed doubly a lot, and the Phosphorescent electron transport material therefore developing high electron mobility has vital effect for the efficiency and reduction device efficiency roll-off improving phosphorescence light emitting device.
Given this, the object of the present invention is to provide a kind of novel organic semiconductor material, phosphorescence host and electron transport material can be used as simultaneously, and electro-phosphorescent luminescent device, be intended to the problem solving the low electronic mobility of organic semiconductor material traditional in prior art, and the technical problem that triplet energy level is high, carrier transport is mated and second-order transition temperature is high can not be realized simultaneously.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of electron type phosphorus oxygen derivative and electro-phosphorescent luminescent device; This electron type phosphorus oxygen derivative can be used as phosphorescence host and electron transport material simultaneously, has the advantages that electronic mobility is high, triplet energy level is high, carrier transport is mated and second-order transition temperature is high.
For solving the problems of the technologies described above, on the one hand, the invention provides a kind of electron type phosphorus oxygen derivative, for phosphorescence host and electron transport material, the general structure of described electron type phosphorus oxygen derivative is as follows:
Wherein, the R in described general structure
1, R
2and R
3all be selected from the one in following heterocyclic substituent: benzoglyoxaline, phenanthro-imidazoles, azepine carbazole, quinoline, quinoline or thiadiazoles.
Further, described R
1, R
2and R
3it is the electron transporting groups that three kinds of structures are identical; Or, described R
1, R
2and R
3in, the electron transporting groups that at least existence two kinds is different.
Further, described R
1for a kind of in following electron transporting groups:
Described R
2for a kind of in following electron transporting groups:
Further, described R
3for a kind of in following electron transporting groups:
Another aspect, the invention provides a kind of electro-phosphorescent luminescent device, based on above-mentioned electron type phosphorus oxygen derivative, described electro-phosphorescent luminescent device is made up of some layers of organic materials, and the transport layer in described electro-phosphorescent luminescent device and/or emitting layer material integral part comprise described electron type phosphorus oxygen derivative.
A kind of electron type phosphorus oxygen derivative provided by the invention, by the electron transporting groups (R that binding on three phenyl ring of triphenyl phosphorus oxygen groups is different
1, R
2and R
3), in order to the transmission of equilbrium carrier, thus obtain the electron type green glow phosphorescent light body material that a class has high triplet, high electron mobility and high thermal stability.Simultaneously, electron type phosphorus oxygen derivative provided by the invention is used as phosphorescence host and electron transport material, and electro-phosphorescent luminescent device, the problem solving the low electronic mobility of organic semiconductor material traditional in prior art can be realized, and can realize solving the technical problem that triplet energy level is high, carrier transport is mated and second-order transition temperature is high simultaneously.
Accompanying drawing explanation
In order to be illustrated more clearly in the embodiment of the present invention or technical scheme of the prior art, be briefly described to the accompanying drawing used required in embodiment below, apparently, accompanying drawing in the following describes is only some embodiments of the present invention, for those of ordinary skill in the art, under the prerequisite not paying creative work, other accompanying drawing can also be obtained according to these accompanying drawings.
The structural representation of the electro-phosphorescent luminescent device that Fig. 1 provides for the embodiment of the present invention; And
The Ultraluminescence of the pNBIPO that Fig. 2 provides for the embodiment of the present invention and phosphorescence spectrum figure; And
The Ultraluminescence of the pPBIPO that Fig. 3 provides for the embodiment of the present invention and phosphorescence spectrum figure; And
The Ultraluminescence of the mNBIPO that Fig. 4 provides for the embodiment of the present invention and phosphorescence spectrum figure; And
The Ultraluminescence of the mPBIPO that Fig. 5 provides for the embodiment of the present invention and phosphorescence spectrum figure; And
The electroluminescent curve of the electroluminescent device prepared as green glow phosphorescent light body material by pNBIPO that Fig. 6 provides for the embodiment of the present invention; And
The CVB curve of the electroluminescent device prepared as green glow phosphorescent light body material by pNBIPO that Fig. 7 provides for the embodiment of the present invention; And
Current efficiency-the brightness curve of the electroluminescent device prepared as green glow phosphorescent light body material by pNBIPO that Fig. 8 provides for the embodiment of the present invention; And
External quantum efficiency-the brightness curve of the electroluminescent device prepared as green glow phosphorescent light body material by pNBIPO that Fig. 9 provides for the embodiment of the present invention.
Embodiment
Below in conjunction with the accompanying drawing in the embodiment of the present invention, be clearly and completely described the technical scheme in the embodiment of the present invention, obviously, described embodiment is only the present invention's part embodiment, instead of whole embodiments.Based on the embodiment in the present invention, the every other embodiment that those of ordinary skill in the art obtain, all belongs to the scope of protection of the invention.
Embodiment one
The embodiment of the present invention one provides a kind of electron type phosphorus oxygen derivative, and for phosphorescence host and electron transport material, the general structure of described electron type phosphorus oxygen derivative is as follows:
Wherein, the R in this electron type phosphorus oxygen derivant structure general formula
1, R
2and R
3all be selected from the one in following heterocyclic substituent: H, benzoglyoxaline, phenanthro-imidazoles, azepine carbazole, quinoline, quinoline or thiadiazoles.Specifically, the electron type phosphorus oxygen derivative that the embodiment of the present invention one provides, wherein, this electron type phosphorus oxygen derivative with triphenyl phosphorus oxygen groups for core, by the electron transporting groups (R that binding on three phenyl ring of triphenyl phosphorus oxygen groups is different
1, R
2and R
3), efficiently solve carrier balance, thus obtain the electron type green glow phosphorescent light body material that a class has high triplet, high electron mobility and high thermal stability.Further, the electron type phosphorus oxygen derivative embodiment of the present invention one provided is used as phosphorescence host and electron transport material, and electro-phosphorescent luminescent device, the problem solving the low electronic mobility of organic semiconductor material traditional in prior art can be realized, and the technical problem that triplet energy level is high, carrier transport is mated and second-order transition temperature is high can not be realized simultaneously.
In the embodiment of the present invention one, R
1, R
2and R
3it can be the electron transporting groups that three kinds of structures are identical; Also can be in three, at least there are two kinds of different electron transporting groups (R
1with R
2identical, or R
1with R
3identical, or R
1, R
2and R
3all identical).
Specifically, R1, R2 and R3 can be any one (not the limiting to) in following electron transporting groups:
It is pointed out that
all the other positions are H;
all the other positions are H.
Specifically can be divided into following four kinds of modes:
1. when
when all the other positions are H, this compound is 4-(1-tolimidazole base)-triphenyl phosphorus oxygen, and referred to as pNBIPO, its molecular structural formula is:
now, this pNBIPO synthesizes by following method:
Step S101: 2-phenyl-4-N-is dissolved in THF (tetrahydrofuran (THF)) to bromophenyl benzoglyoxaline; Preferably, in this step, 2-phenyl-4-N-is 1.0mmol, THF (tetrahydrofuran (THF)) to bromophenyl benzoglyoxaline is 50ml;
Step S102: be cooled to-78 DEG C, adds n-Butyl Lithium, reacts one hour; Preferably, in this step, n-Butyl Lithium is 1.1mmol;
Step S103: add diphenyl phosphorus chloride, is warming up to room temperature reaction 12 hours; Preferably, in this step, diphenyl phosphorus chloride is 1.2mmol;
Step S104; Add methyl alcohol quencher reaction, add 30%H simultaneously
2o
2aqueous solution chlorination obtains 4-(1-tolimidazole base)-triphenyl phosphorus oxygen; Preferably, 30%H in this step
2o
2the aqueous solution is 5ml; Productive rate: 70%; Mass spectrum MS (APCI): calcd for C
31h
23n
2oP:470.5, found, 471.4 (M+1)
+.
2. when
when all the other positions are H, this compound is 4-(2-tolimidazole base)-triphenyl phosphorus oxygen, and referred to as pPBIPO, its molecular structural formula is:
now, this pPBIPO synthesizes by following method:
Step S201: N-phenyl-4-is dissolved in THF (tetrahydrofuran (THF)) to bromophenyl benzoglyoxaline; Preferably, in this step, N-phenyl-4-is 1.0mmol, THF (tetrahydrofuran (THF)) to bromophenyl benzoglyoxaline is 50ml;
Step S202: be cooled to-78 DEG C, adds n-Butyl Lithium, reacts one hour; Preferably, in this step, n-Butyl Lithium is 1.1mmol;
Step S203: add diphenyl phosphorus chloride, is warming up to room temperature reaction 12 hours; Preferably, in this step, diphenyl phosphorus chloride is 1.2mmol;
Step S204; Add methyl alcohol quencher reaction, add 30%H simultaneously
2o
2aqueous solution chlorination obtains 4-(2-tolimidazole base)-triphenyl phosphorus oxygen; Preferably, 30%H in this step
2o
2the aqueous solution is 5ml; Productive rate: 70%; Mass spectrum MS (APCI): calcd for C
31h
23n
2oP:470.5, found, 471.4 (M+1)
+.
3. when
when all the other positions are H, this compound is 3-(1-tolimidazole base)-triphenyl phosphorus oxygen, and referred to as mNBIPO, its molecular structural formula is:
now, this mNBIPO synthesizes by following method:
Step S301: bromophenyl benzoglyoxaline between 2-phenyl-3-is dissolved in THF (tetrahydrofuran (THF)); Preferably, in this step, between 2-phenyl-3-, bromophenyl benzoglyoxaline is 1.0mmol, THF (tetrahydrofuran (THF)) is 50ml;
Step S302: be cooled to-78 DEG C, adds n-Butyl Lithium, reacts one hour; Preferably, in this step, n-Butyl Lithium is 1.1mmol;
Step S303: add diphenyl phosphorus chloride, is warming up to room temperature reaction 12 hours; Preferably, in this step, diphenyl phosphorus chloride is 1.2mmol;
Step S304; Add methyl alcohol quencher reaction, add 30%H simultaneously
2o
2aqueous solution chlorination obtains 3-(1-tolimidazole base)-triphenyl phosphorus oxygen; Preferably, 30%H in this step
2o
2the aqueous solution is 5ml; Productive rate: 70%; Mass spectrum MS (APCI): calcd for C
31h
23n
2oP:470.5, found, 471.4 (M+1)
+.
4. when
when all the other positions are H, this compound is 3-(2-tolimidazole base)-triphenyl phosphorus oxygen, and referred to as mPBIPO, its molecular structural formula is:
now, this mPBIPO synthesizes by following method:
Step S401: bromophenyl benzoglyoxaline between N-phenyl-3-is dissolved in THF (tetrahydrofuran (THF)); Preferably, in this step, between N-phenyl-3-, bromophenyl benzoglyoxaline is 1.0mmol, THF (tetrahydrofuran (THF)) is 50ml;
Step S402: be cooled to-78 DEG C, adds n-Butyl Lithium, reacts one hour; Preferably, in this step, n-Butyl Lithium is 1.1mmol;
Step S403: add diphenyl phosphorus chloride, is warming up to room temperature reaction 12 hours; Preferably, in this step, diphenyl phosphorus chloride is 1.2mmol;
Step S404; Add methyl alcohol quencher reaction, add 30%H simultaneously
2o
2aqueous solution chlorination obtains 3-(2-tolimidazole base)-triphenyl phosphorus oxygen; Preferably, 30%H in this step
2o
2the aqueous solution is 5ml; Productive rate: 70%; Mass spectrum MS (APCI): calcd for C
31h
23n
2oP:470.5, found, 471.4 (M+1)
+.
Need to further illustrate, based on electron transporting groups (R
1, R
2and R
3) combined transformation, the optional one in following listed derivative (1a-13c) of the electron type phosphorus oxygen derivative that the embodiment of the present invention one provides:
Embodiment two
Based on the electron type phosphorus oxygen derivative that the embodiment of the present invention one provides, the embodiment of the present invention two provides a kind of electro-phosphorescent luminescent device, this electro-phosphorescent luminescent device is made up of some layers of organic materials, wherein, the transport layer in electro-phosphorescent luminescent device or emitting layer material integral part comprise the electron type phosphorus oxygen derivative that the embodiment of the present invention one provides.
Specifically, four kinds of compound 4-(1-tolimidazole the base)-triphenyl phosphorus oxygen embodiment of the present invention one provided, 4-(2-tolimidazole base)-triphenyl phosphorus oxygen, 3-(1-tolimidazole base)-triphenyl phosphorus oxygen, 3-(2-tolimidazole base)-triphenyl phosphorus oxygen (can consult Ultraluminescence and the phosphorescence spectrum figure of kind of the compound of four shown in Fig. 2-5), prepare electro-phosphorescent luminescent device as green phosphorescent material of main part; This device configuration schematic diagram can consult Fig. 1; Wherein, ITO is as transparent conductive anode, molybdic oxide is as hole injection layer, NPB is hole transmission layer, TCTA is exciton barrier layer, and Ir (ppy) 3 that adulterated by phosphorescent light body material is as luminescent layer, and TmPyPB is as electron transfer layer, LiF is as electron injecting layer, and Al is as negative electrode; The preparation of each electroluminescent device (device 1, device 2, device 3 and device 4) can consult following table:
Prepare electro-phosphorescent luminescent device for each green phosphorescent material of main part, concrete preparation process can be consulted as follows:
(1) when 4-(1-tolimidazole base)-triphenyl phosphorus oxygen prepares electro-phosphorescent luminescent device as green phosphorescent material of main part; First ito glass in succession in clean-out system and deionized water with ultrasonic cleaning 30 minutes; Then vacuum-drying 2 hours (105 DEG C), then CFx plasma treatment ito glass being put into plasma reactor carries out 1 minute, be sent in vacuum chamber and prepare organic membrane and metal electrode; 4-(1-tolimidazole base)-triphenyl phosphorus oxygen (pNBIPO) is prepared into electro-phosphorescent luminescent device as green phosphorescent material of main part by the method eventually through vacuum evaporation; This electro-phosphorescent luminescent device structure is: ITO/MoO
3(10nm)/NPB (70nm)/TCTA (5nm)/pNBIPO-Ir (ppy)
3(20nm)/TmPyPB (40nm)/LiF (1nm)/Al.
(2) when 4-(2-tolimidazole base)-triphenyl phosphorus oxygen prepares electro-phosphorescent luminescent device as green phosphorescent material of main part; First ito glass in succession in clean-out system and deionized water with ultrasonic cleaning 30 minutes, then vacuum-drying 2 hours (105 DEG C), again ito glass is put into the CFx plasma treatment that plasma reactor carries out 1 minute, be sent in vacuum chamber and prepare organic membrane and metal electrode; 4-(2-tolimidazole base)-triphenyl phosphorus oxygen (pPBIPO) is prepared into electro-phosphorescent luminescent device as green phosphorescent material of main part by the method finally by vacuum evaporation; This electro-phosphorescent luminescent device structure is: ITO/MoO
3(10nm)/NPB (70nm)/TCTA (5nm)/pPBIPO-Ir (ppy)
3(20nm)/TmPyPB (40nm)/LiF (1nm)/Al.
(3) when 3-(1-tolimidazole base)-triphenyl phosphorus oxygen prepares electro-phosphorescent luminescent device as green phosphorescent material of main part; First ito glass in succession in clean-out system and deionized water with ultrasonic cleaning 30 minutes, then vacuum-drying 2 hours (105 DEG C), again ito glass is put into the CFx plasma treatment that plasma reactor carries out 1 minute, be sent in vacuum chamber and prepare organic membrane and metal electrode; 3-(1-tolimidazole base)-triphenyl phosphorus oxygen (mNBIPO) is prepared into electro-phosphorescent luminescent device as green phosphorescent material of main part by the method finally by vacuum evaporation; This electro-phosphorescent luminescent device structure is: ITO/MoO
3(10nm)/NPB (70nm)/TCTA (5nm)/mPBIPO-Ir (ppy)
3(20nm)/TmPyPB (40nm)/LiF (1nm)/Al.
(4) when 3-(2-tolimidazole base)-triphenyl phosphorus oxygen prepares electro-phosphorescent luminescent device as green phosphorescent material of main part; First ito glass in succession in clean-out system and deionized water with ultrasonic cleaning 30 minutes, then vacuum-drying 2 hours (105 DEG C), again ito glass is put into the CFx plasma treatment that plasma reactor carries out 1 minute, be sent in vacuum chamber and prepare organic membrane and metal electrode; 3-(2-tolimidazole base)-triphenyl phosphorus oxygen (mPBIPO) is prepared into electro-phosphorescent luminescent device as green phosphorescent material of main part by the method finally by vacuum evaporation; This electro-phosphorescent luminescent device structure is: ITO/MoO
3(10nm)/NPB (70nm)/TCTA (5nm)/mPBIPO-Ir (ppy)
3(20nm)/TmPyPB (40nm)/LiF (1nm)/Al.
Refer to Fig. 2,6-9 (for pNBIPO); A kind of electron type phosphorus oxygen derivative provided by the invention, by this electron type phosphorus oxygen derivative is used as luminescent material, as host emitter or electron transfer layer, can be widely used in field of organic electroluminescence; Specifically, this electron type phosphorus oxygen derivative with triphenyl phosphorus oxygen groups for core, by the electron transporting groups (R that binding on three phenyl ring of triphenyl phosphorus oxygen groups is different
1, R
2and R
3), efficiently solve carrier balance, thus obtain the electron type green glow phosphorescent light body material that a class has high triplet, high electron mobility and high thermal stability.Meanwhile, electro-phosphorescent luminescent device is by selecting electron type phosphorus oxygen derivative as the transport layer of its integral part or emitting layer material, and brightness is high, efficiency is high and low feature of roll-offing to have made it possess.
It should be noted last that, above embodiment is only in order to illustrate technical scheme of the present invention and unrestricted, although with reference to example to invention has been detailed description, those of ordinary skill in the art is to be understood that, can modify to technical scheme of the present invention or equivalent replacement, and not departing from the spirit and scope of technical solution of the present invention, it all should be encompassed in the middle of right of the present invention.
Claims (4)
1. an electron type phosphorus oxygen derivative, for phosphorescence host and electron transport material, is characterized in that, the general structure of described electron type phosphorus oxygen derivative is as follows:
Wherein, the R in described general structure
1, R
2and R
3all be selected from the one in following heterocyclic substituent: benzoglyoxaline, phenanthro-imidazoles, azepine carbazole, quinoline, quinoline or thiadiazoles.
2. an electron type phosphorus oxygen derivative, is characterized in that:
Described R
1, R
2and R
3it is the electron transporting groups that three kinds of structures are identical;
Or,
Described R
1, R
2and R
3in, the electron transporting groups that at least existence two kinds is different.
3. an electron type phosphorus oxygen derivative, is characterized in that:
Described R
1for a kind of in following electron transporting groups:
And/or,
Described R
2for a kind of in following electron transporting groups:
And/or,
Described R
3for a kind of in following electron transporting groups:
4. an electro-phosphorescent luminescent device, based on electron type phosphorus oxygen derivative according to claim 1, described electro-phosphorescent luminescent device is made up of some layers of organic materials, it is characterized in that:
Transport layer in described electro-phosphorescent luminescent device and/or emitting layer material integral part comprise described electron type phosphorus oxygen derivative.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104194778A (en) * | 2014-09-25 | 2014-12-10 | 黑龙江大学 | Phosphorus-oxygen group modified N-phenyl-benzimidazole electronic transmission material and synthesis method thereof and preparation method of electrophosphorescence device |
| CN105837630A (en) * | 2016-04-27 | 2016-08-10 | 中国广州分析测试中心 | Decyl imidazole blue-light emission organic light-emitting material and preparation method thereof |
| CN106299155A (en) * | 2016-09-21 | 2017-01-04 | 武汉华星光电技术有限公司 | OLED luminescent device and display device |
| CN106496269A (en) * | 2016-09-21 | 2017-03-15 | 武汉华星光电技术有限公司 | Triphenyl phosphorus oxygen derivative and electro-phosphorescent luminescent device |
| CN113735833A (en) * | 2021-10-11 | 2021-12-03 | 西安瑞联新材料股份有限公司 | Compound with phenanthrocarbazole as core and application thereof |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104194778A (en) * | 2014-09-25 | 2014-12-10 | 黑龙江大学 | Phosphorus-oxygen group modified N-phenyl-benzimidazole electronic transmission material and synthesis method thereof and preparation method of electrophosphorescence device |
| CN104194778B (en) * | 2014-09-25 | 2016-03-30 | 黑龙江大学 | Phosphorus-oxygen groups modifies the preparation method of N-Phenyl-benzoimidazol electron transport material, synthetic method and electro phosphorescent device |
| CN105837630A (en) * | 2016-04-27 | 2016-08-10 | 中国广州分析测试中心 | Decyl imidazole blue-light emission organic light-emitting material and preparation method thereof |
| CN106299155A (en) * | 2016-09-21 | 2017-01-04 | 武汉华星光电技术有限公司 | OLED luminescent device and display device |
| CN106496269A (en) * | 2016-09-21 | 2017-03-15 | 武汉华星光电技术有限公司 | Triphenyl phosphorus oxygen derivative and electro-phosphorescent luminescent device |
| WO2018053937A1 (en) * | 2016-09-21 | 2018-03-29 | 武汉华星光电技术有限公司 | Triphenylphosphine oxide derivative and electrophosphorescent device |
| CN113735833A (en) * | 2021-10-11 | 2021-12-03 | 西安瑞联新材料股份有限公司 | Compound with phenanthrocarbazole as core and application thereof |
| CN113735833B (en) * | 2021-10-11 | 2023-02-10 | 西安瑞联新材料股份有限公司 | Compound with phenanthrocarbazole as core and application thereof |
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