CN103483364A - Bis-benzothiophene borane luminescent material and preparation method thereof - Google Patents
Bis-benzothiophene borane luminescent material and preparation method thereof Download PDFInfo
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Abstract
The invention belongs to the field of luminescent materials, and particularly relates to a bis-benzothiophene borane luminescent material and a preparation method thereof. The luminescent material structurally contains bis-benzothiophene and two diphenyl boranes, and has the following advantages: (1) the luminescent material is a novel multipurpose luminescent material which can be used as an electronic transmission layer material and a luminescent layer material; and since the molecular structure contains S, B and other heteroatoms, the electron mobility is high in the material, and thus, the luminescent material is hopeful to basically solve the core problem of restriction to luminescence efficiency of devices.
Description
Technical field
The invention belongs to the luminescent material technical field, be specifically related to a kind of pair of thionaphthene borine luminescent material and preparation method thereof.
Background technology
The research work of organic electroluminescent started from for 20 discipline sixties, but until the people such as Deng Qingyun of Kodak in 1987 adopt multi-layer film structure, just obtained first the Organic Light Emitting Diode (OLED) of high-quantum efficiency, high-luminous-efficiency, high brightness and low driving voltage, this breakthrough makes OLED become the focus of luminescent device research.With traditional luminous and technique of display, compare, OLED has the advantages such as driving voltage is low, volume is little, lightweight, material category is abundant, and easily realizes the preparation of big area preparation, wet method preparation and flexible device.In recent years, the develop rapidly of OLED technology, calendar year 2001, Sony is succeeded in developing 13 inches Full-color OLED indicating meters, has proved that OLED can show for large flat; 2002, SANYO GS company combined with Kodak and has released the digital camera that adopts active driving OLED to show, indicates that the industrialization of OLED has stepped again solid step forward; 2013, Sony corporation of Japan was released the OLED colour television set of 37 inches, took the lead in realizing that OLED is in middle large size, particularly at the application breakthrough of TV domain.
The present invention to two thionaphthenes, is a kind of novel organic luminescent material by the grafting of phenylbenzene borine, and its advantage is as follows: (1) is a kind of multiduty luminescent material, can be as the electric transmission layer material, and also can be as the luminescent layer materials'use.(2) owing to containing the heteroatomss such as S and B in molecular structure, the mobility of electronics in material is high, fundamentally solves the key problem of restriction device luminous efficiency.
Summary of the invention
The object of the invention is to propose a kind of pair of thionaphthene borine luminescent material and preparation method thereof.
Two thionaphthene borine luminescent materials that the present invention proposes, structurally contain two thionaphthenes, and two phenylbenzene borines, and the molecular formula of material is C
38h
26b
2s
2, chemical structural formula is as follows:
The name of this compound is called: two (phenylbenzene the boryl)-thionaphthenes of 2,7-are [3,2-b] [1] thionaphthene also
English name is: 2,7-di (diphenylborane)-Benzothieno[3,2-b] [1] benzothiophene.
The invention allows for the preparation method of this luminescent material, concrete steps are as follows: under nitrogen protection, add 2 in three-necked bottle; 7-dibromobenzene thiophthene also [3; 2-b] [1] thionaphthene, bromine phenylbenzene borine, lithium alkylide, palladium compound catalyzer, cyclodextrin and tetrahydrofuran (THF), be cooled to-78～-8 ℃ of reactions 2～6 hours, after reaction finishes; add water; remove solvent under reduced pressure, resistates extracts by ethyl acetate, concentrated; crude product is purified by the vacuum-sublimation method, obtains the target luminescent material.Wherein lithium alkylide used is n-Butyl Lithium, tert-butyl lithium, n-pentyl lithium a kind of; Wherein palladium compound catalyzer used is a kind of of Palladous chloride, palladium, oxalic acid palladium; Wherein bromine phenylbenzene borine, lithium alkylide, palladium compound catalyzer, cyclodextrin and 2,7-dibromobenzene thiophthene also the consumption mol ratio of [3,2-b] [1] thionaphthene be respectively 2.0～2.1,3.0～3.4,0.01～0.02,0.3～0.4.
The accompanying drawing explanation
Fig. 1 is two thionaphthene borine luminescent material structure formulas.
Embodiment
The invention is further illustrated by the following examples
Embodiment 1
Under nitrogen protection, add 2 in the 500mL three-necked bottle, 7-dibromobenzene thiophthene also [3, 2-b] [1] thionaphthene 0.01mol, bromine phenylbenzene borine 0.02mol, the n-Butyl Lithium pentane solution 30mL of 1M, Palladous chloride 0.1mmol, cyclodextrin 3mmol and tetrahydrofuran (THF) 150mL, be cooled to-78 ℃ of reactions 2 hours, after reaction finishes, add water 100mL, remove solvent under reduced pressure, resistates extracts with ethyl acetate 300mL, concentrated, crude product is purified by the vacuum-sublimation method, obtain luminescent material 2, 7-dibromobenzene thiophthene also [3, 2-b] [1] thionaphthene, yield: 38%, fusing point: > 300 ℃, ultimate analysis: C, 80.33, H, 4.64, B, 3.81, S, 11.22, calculated value C, 80.30, H, 4.61, B, 3.80, S, 11.28, mass spectrometric measurement: m/z:568 (100.0%).
The vacuum vapour deposition of take is made the device that structure is ITO/NPB (100nm)/bis-thionaphthene borine luminescent material (60nm)/Alq3 (100nm)/Mg:Ag, the device green light, and luminous efficiency is 4.8cd/A.
Embodiment 2
Under nitrogen protection, add 2 in the 500mL three-necked bottle, 7-dibromobenzene thiophthene also [3, 2-b] [1] thionaphthene 0.01mol, bromine phenylbenzene borine 0.021mol, the tert-butyl lithium pentane solution 34mL of 1M, palladium 0.2mmol, cyclodextrin 4mmol and tetrahydrofuran (THF) 150mL, be cooled to-8 ℃ of reactions 6 hours, after reaction finishes, add water 100mL, remove solvent under reduced pressure, resistates extracts with ethyl acetate 300mL, concentrated, crude product is purified by the vacuum-sublimation method, obtain luminescent material 2, 7-dibromobenzene thiophthene also [3, 2-b] [1] thionaphthene, yield: 26%, fusing point: > 300 ℃, ultimate analysis: C, 80.33, H, 4.64, B, 3.81, S, 11.22, calculated value C, 80.30, H, 4.61, B, 3.80, S, 11.28, mass spectrometric measurement: m/z:568 (100.0%).
The vacuum vapour deposition of take is made the device that structure is ITO/NPB (100nm)/Alq3 (100nm)/couple thionaphthene borine luminescent material (60nm)/Mg:Ag, the device green light, and luminous efficiency is 5.4cd/A.
Embodiment 3
Under nitrogen protection, add 2 in the 500mL three-necked bottle, 7-dibromobenzene thiophthene also [3, 2-b] [1] thionaphthene 0.01mol, bromine phenylbenzene borine 0.021mol, the n-pentyl lithium pentane solution 32mL of 1M, oxalic acid palladium 0.15mmol, cyclodextrin 3.5mmol and tetrahydrofuran (THF) 150mL, be cooled to-78 ℃ of reactions 6 hours, after reaction finishes, add water 100mL, remove solvent under reduced pressure, resistates extracts with ethyl acetate 300mL, concentrated, crude product is purified by the vacuum-sublimation method, obtain luminescent material 2, 7-dibromobenzene thiophthene also [3, 2-b] [1] thionaphthene, yield: 46%, fusing point: > 300 ℃, ultimate analysis: C, 80.33, H, 4.64, B, 3.81, S, 11.22, calculated value C, 80.30, H, 4.61, B, 3.80, S, 11.28, mass spectrometric measurement: m/z:568 (100.0%).
The vacuum vapour deposition of take is made the device that structure is ITO/NPB (100nm)/couple thionaphthene borine luminescent material (160nm)/Mg:Ag, the device green light, and luminous efficiency is 5.3cd/A.
Embodiment 4
Under nitrogen protection, add 2 in the 500mL three-necked bottle, 7-dibromobenzene thiophthene also [3, 2-b] [1] thionaphthene 0.01mol, bromine phenylbenzene borine 0.02mol, the n-Butyl Lithium pentane solution 34mL of 1M, oxalic acid palladium 0.2mmol, cyclodextrin 3mmol and tetrahydrofuran (THF) 150mL, be cooled to-48 ℃ of reactions 4 hours, after reaction finishes, add water 100mL, remove solvent under reduced pressure, resistates extracts with ethyl acetate 300mL, concentrated, crude product is purified by the vacuum-sublimation method, obtain luminescent material 2, 7-dibromobenzene thiophthene also [3, 2-b] [1] thionaphthene, yield: 57%, fusing point: > 300 ℃, ultimate analysis: C, 80.33, H, 4.64, B, 3.81, S, 11.22, calculated value C, 80.30, H, 4.61, B, 3.80, S, 11.28, mass spectrometric measurement: m/z:568 (100.0%).
The vacuum vapour deposition of take is made the device that structure is ITO/NPB (100nm)/couple thionaphthene borine luminescent material (160nm)/Mg:Ag, the device green light, and luminous efficiency is 5.3cd/A.
Embodiment 5
Under nitrogen protection, add 2 in the 500mL three-necked bottle, 7-dibromobenzene thiophthene also [3, 2-b] [1] thionaphthene 0.01mol, bromine phenylbenzene borine 0.02mol, the n-Butyl Lithium pentane solution 34mL of 1M, palladium 0.25mmol, cyclodextrin 3.5mmol and tetrahydrofuran (THF) 150mL, be cooled to-15 ℃ of reactions 3 hours, after reaction finishes, add water 100mL, remove solvent under reduced pressure, resistates extracts with ethyl acetate 300mL, concentrated, crude product is purified by the vacuum-sublimation method, obtain luminescent material 2, 7-dibromobenzene thiophthene also [3, 2-b] [1] thionaphthene, yield: 41%, fusing point: > 300 ℃, ultimate analysis: C, 80.33, H, 4.64, B, 3.81, S, 11.22, calculated value C, 80.30, H, 4.61, B, 3.80, S, 11.28, mass spectrometric measurement: m/z:568 (100.0%).
The vacuum vapour deposition of take is made the device that structure is ITO/NPB (100nm)/couple thionaphthene borine luminescent material (160nm)/Mg:Ag, the device green light, and luminous efficiency is 5.3cd/A.
Claims (5)
1. two thionaphthene borine luminescent materials and preparation method thereof, is characterized in that this material structurally contains two thionaphthenes, and two phenylbenzene borines, and the molecular formula of material is C
38h
26b
2s
2, chemical structural formula is as follows:
The name of this compound is called: two (phenylbenzene the boryl)-thionaphthenes of 2,7-are [3,2-b] [1] thionaphthene also
English name is: 2,7-di (diphenylborane)-Benzothieno[3,2-b] [1] benzothiophene.
2. the preparation method of a luminescent material as claimed in claim 1; it is characterized in that: under nitrogen protection; add 2 in three-necked bottle; 7-dibromobenzene thiophthene also [3; 2-b] [1] thionaphthene, bromine phenylbenzene borine, lithium alkylide, palladium compound catalyzer, cyclodextrin and tetrahydrofuran (THF); be cooled to-78～-8 ℃ of reactions 2～6 hours; after reaction finishes; add water; remove solvent under reduced pressure, resistates extracts by ethyl acetate, concentrated; crude product is purified by the vacuum-sublimation method, obtains the target luminescent material.
3. the preparation method of luminescent material according to claim 2, is characterized in that lithium alkylide used is n-Butyl Lithium, tert-butyl lithium, n-pentyl lithium a kind of.
4. the preparation method of luminescent material according to claim 2, is characterized in that palladium compound catalyzer used is a kind of of Palladous chloride, palladium, oxalic acid palladium.
5. the preparation method of luminescent material according to claim 2, it is characterized in that bromine phenylbenzene borine, lithium alkylide, palladium compound catalyzer, cyclodextrin and 2,7-dibromobenzene thiophthene also [3,2-b] the consumption mol ratio of [1] thionaphthene is respectively 2.0～2.1,3.0～3.4,0.01～0.02,0.3～0.4.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107474827A (en) * | 2017-08-11 | 2017-12-15 | 太仓碧奇新材料研发有限公司 | The preparation method of composite construction tribo-luminescence film |
| CN107507921A (en) * | 2017-09-29 | 2017-12-22 | 江苏三月光电科技有限公司 | A kind of boracic organic electroluminescence device and preparation method thereof |
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| CN1554127A (en) * | 2000-12-22 | 2004-12-08 | �����л��뵼������˾ | Use of boron and aluminium compounds in electronic components |
| CN1997650A (en) * | 2004-03-10 | 2007-07-11 | 独立行政法人科学技术振兴机构 | Chalcogen-containing fused-ring polycyclic organic material and process for producing the same |
| CN102007131A (en) * | 2008-04-17 | 2011-04-06 | 株式会社理光 | [1]benzothieno[3,2-b][1]benzothiophene compound and method for producing the same, and organic electronic device using the same |
| CN102827196A (en) * | 2012-09-12 | 2012-12-19 | 山西大学 | Boron-containing indole (3, 2-b) carbazole derivative and preparion method and application thereof |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1554127A (en) * | 2000-12-22 | 2004-12-08 | �����л��뵼������˾ | Use of boron and aluminium compounds in electronic components |
| CN1997650A (en) * | 2004-03-10 | 2007-07-11 | 独立行政法人科学技术振兴机构 | Chalcogen-containing fused-ring polycyclic organic material and process for producing the same |
| CN102007131A (en) * | 2008-04-17 | 2011-04-06 | 株式会社理光 | [1]benzothieno[3,2-b][1]benzothiophene compound and method for producing the same, and organic electronic device using the same |
| CN102827196A (en) * | 2012-09-12 | 2012-12-19 | 山西大学 | Boron-containing indole (3, 2-b) carbazole derivative and preparion method and application thereof |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107474827A (en) * | 2017-08-11 | 2017-12-15 | 太仓碧奇新材料研发有限公司 | The preparation method of composite construction tribo-luminescence film |
| CN107507921A (en) * | 2017-09-29 | 2017-12-22 | 江苏三月光电科技有限公司 | A kind of boracic organic electroluminescence device and preparation method thereof |
| WO2019062685A1 (en) * | 2017-09-29 | 2019-04-04 | 江苏三月光电科技有限公司 | Boron-containing organic light-emitting device and fabrication method therefor |
| CN107507921B (en) * | 2017-09-29 | 2019-05-14 | 江苏三月光电科技有限公司 | A kind of boracic organic electroluminescence device and preparation method thereof |
| US11778894B2 (en) | 2017-09-29 | 2023-10-03 | Jiangsu Sunera Technology Co., Ltd. | Boron-containing organic light-emitting diode device and preparation method thereof |
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