CN106810569B - Carboline trisubstituted derivative and application thereof - Google Patents
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Abstract
The invention discloses a carboline trisubstituted derivative and application thereof, wherein the structural general formula is as follows:
in the formula, X1、X2Can be independently selected from C, N, and only one is N atom; r is selected from any one of a hydrogen atom, a halogen atom, an alkyl group, a substituted alkyl group, a cyano group, an amino group, a substituted silyl group, a phenyl group, a naphthyl group, a substituted or unsubstituted aryl group, a biaryl group, a condensed ring aryl group, a substituted or unsubstituted nitrogen atom-containing heterocyclic aryl group and a benzoheterocyclic aryl group; the compound can be applied to a transmission layer material and a luminescent layer material in an organic electroluminescent device. The invention can be used as an electron or hole transport material and can also be used as a luminophor, and the luminophor can be independently used as a luminescent layer or used as a host doped dye to emit light or form an exciplex with other materials to emit light; when the invention is used for the organic electroluminescent body, the triplet state energy is high, and the transmission capability of electrons and holes of the main material is balanced, so that the efficiency of the luminescent device is high.
Description
Technical Field
The invention relates to the technical field of carboline derivatives, in particular to a carboline tri-substituted derivative and application thereof.
Background
Due to the continuous development of the display industry, the requirements on flat panel display products are higher and higher, and the current display technologies mainly include three types: plasma displays, field emission displays, and organic electroluminescent displays (OLEDs). Among them, the organic electroluminescent diode is considered as a new application technology of the next generation of flat panel display because it has excellent characteristics of self-luminescence, no need of backlight, high contrast, thin thickness, wide viewing angle, fast reaction speed, applicability to flexible panels, wide temperature range, simple structure and process, etc.
In 1987, C.W. Tang et al of KODAK company in USA adopted evaporation technology, ITO was used as anode, NPB (75 nm) was used as hole transport layer to evaporate on ITO glass, then Alq3 (60 nm) was evaporated to be used as electron transport layer and luminescent layer, finally magnesium and aluminum with low work function were evaporated to be used as cathode, and a double-layer structure device with sandwich structure was made, under about 5V voltage, high-brightness green light was observed, the brightness reached 1000cd/m2, the current efficiency reached 3cd/A, and the external quantum efficiency reached 1%. The breakthrough work has the significance of milestones, creates a new era of organic photoelectric research, and points out the direction of organic electroluminescence research.
In 1990, polymer electroluminescent devices (PLEDs) were fabricated by spin coating of poly-p-phenylene vinylene (PPV) as a conjugated polymer material.
In 1994, the Kido research group of mountain university in Japan made white light OLED devices for the first time, and opened the door of white light OLED research, so that the organic electroluminescent device can be used for illumination. The application field of the OLED is developed again.
In 1998, Forrest research group at Princeton university in America adopts a host-guest doping method to dope a high-efficiency luminescent organic phosphorescent material into a host material, so that singlet excitons and triplet excitons emit light simultaneously, and a high-efficiency phosphorescent OLED is obtained, thereby breaking through the limitation of 25% of the maximum internal quantum efficiency of organic electroluminescence and realizing that the internal quantum efficiency reaches 100%. This work has opened up a new field of organic electroluminescence, phosphorescent OLEDs, and has greatly driven the development of organic electroluminescence.
In 2004, Liao et al, Kodak, USA, and Kido group, Japan mountain university, produced OLEDs using a stacked (Tandem) device structure, the device efficiency reached 136.3cd/A, and the device lifetime was extended.
In 2013, Jun Yeob Lee in Korea synthesizes an alpha-carboline derivative by introducing an alpha-carboline group, and the alpha-carboline derivative is used as a host material to obtain a blue phosphorescent device with external quantum efficiency of 30%, which is one of OLED devices with the highest external quantum efficiency so far.
The light emission mechanism of an OLED is generally considered to be that electrons injected from a cathode and holes injected from an anode are recombined in an organic substance under the drive of an external voltage, and energy is transferred to an organic light emitting molecule, electric energy is converted into an internal energy of the molecule, which is excited to transition from a ground state to an excited state, and when the excited molecule returns to the ground state from the excited state, radiation transition occurs to generate a light emission phenomenon. The light emitting process of the OLED can be divided into four parts, which are: injecting carriers; the transmission of carriers; recombination, in which holes and electrons meet in the light-emitting layer to recombine; excitons are generated and release energy through radiative and non-radiative processes.
In a conventional OLED device, the injection/transport speed of holes is usually several orders of magnitude faster than that of electrons, and the number of holes in the exciton conforming region in the OLED device is significantly larger than that of electrons, so that all electron-hole pairs cannot be fully utilized, and the efficiency and the service life of the device are reduced. Generally, the electron injection/transmission capability of the electron transport layer is improved, so that the luminous efficiency and the service life of the device can be effectively improved. The carboline is one of aza carbazole functional groups, so that the carboline group has better electron transport capability when having hole transport capability, and the introduction of the carboline group can reduce the LUMO orbital energy level of the material, thereby being more beneficial to the injection of electrons.
Disclosure of Invention
In order to solve the problems in the prior art, the invention aims to provide a carboline tri-substituted derivative of an injection/transport layer material and a luminescent layer material for an organic electroluminescent device, which balances the transport capability of electrons and holes in the material by introducing carboline groups. The compound of the invention can form a good amorphous film and has quite good stability of heat, light and the like.
In order to achieve the purpose, the invention adopts the technical scheme that:
the carboline trisubstituted derivative has glass transition temperature of 50-250 deg.c, and the core group in the material structure is carboline group with molecular structure as shown
）：
In the formula X1、X2Can be independently selected from C, N, and only one is N atom; r is selected from any one of a hydrogen atom, a halogen atom, an alkyl group, a substituted alkyl group, a cyano group, an amino group, a substituted silyl group, a phenyl group, a naphthyl group, a substituted or unsubstituted aryl group, a biaryl group, a condensed ring aryl group, a substituted or unsubstituted nitrogen atom-containing heterocyclic aryl group and a benzoheterocyclic aryl group;
the compound can be applied to a transmission layer material and a luminescent layer material in an organic electroluminescent device. Wherein Ar is1Preferred structural formulas are as follows, but are not limited to:
wherein when R is1Preferably selected from hydrogen atoms, wherein the preferred specific material structural formula is as follows:
by adopting the technical scheme, compared with the prior art, the carboline tri-substituted derivative has the beneficial effects that:
1. the carboline tri-substituted derivative can be used as an electron or hole transport material and also can be used as a luminous body, and the luminous body independently becomes a luminous layer or is used as a main body doped dye to emit light or forms an exciplex with other materials to generate light;
2. when the carboline tri-substituted derivative is used for an organic electroluminescent body, the triplet state energy is high, the transmission capability of electrons and holes of the main material is balanced, and the efficiency of a luminescent device is high.
Drawings
FIG. 1 is a graph showing an ultraviolet absorption spectrum of B-4;
FIG. 2 is a graph showing the electroluminescence spectrum of a light-emitting layer doped with Firpic B-4;
FIG. 3 is a graph of luminance-voltage-current density for a device with B-4 doped Firpic as the light emitting layer.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the accompanying drawings and specific examples. It should be understood that the description is intended to be exemplary only, and is not intended to limit the scope of the present invention. Moreover, in the following description, descriptions of well-known structures and techniques are omitted so as to not unnecessarily obscure the concepts of the present invention.
The first embodiment is as follows: preparation of Compound A1
6 g of alpha-carboline, 8.5 g of 1,3, 5-tribromobenzene, 14 g of potassium carbonate, 0.7 g of cuprous iodide, 120 ml of N, N-dimethylformamide and reflux reaction for 24 hours under the protection of nitrogen. After the reaction is finished, suction filtration is carried out, the filtrate is extracted by ethyl acetate, washed by saturated saline, dried, concentrated and subjected to column chromatography, 4.5 g of solid is obtained, and the yield is 67%. Mass spectrum, theoretical value m/e, 576.2; found 576.1.
The second embodiment: preparation of Compound A7
6 g of delta-carboline, 8.5 g of 2,4, 6-tribromopyridine, 14 g of potassium carbonate, 0.7 g of cuprous iodide and 120 ml of N, N-dimethylformamide are refluxed for 24 hours under the protection of nitrogen. After the reaction is finished, suction filtration is carried out, the filtrate is extracted by ethyl acetate, washed by saturated saline, dried, concentrated and subjected to column chromatography, and solid 5.8 g is obtained, and the yield is 85%. Mass spectrum, theoretical value m/e, 577.6; found 577.5.
Example three: preparation of Compound B4
a) Synthesizing N- (3-bromophenyl) -delta-carboline: 2g of delta-Carboline, 8.5 g of m-dibromobenzene, 14 g of potassium carbonate, 0.7 g of cuprous iodide, 50 ml of N, N-dimethylformamide and reflux reaction for 24 hours under the protection of nitrogen. After the reaction, the reaction solution was filtered, and the filtrate was extracted with ethyl acetate, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 2.0 g of a solid with a yield of 54%. Mass spectrum, theoretical value m/e, 323.2; found 323.2.1H-NMR(500MHz,CDCl3): 8.62(1H), 8.44(1H), 7.74-7.68(2H), 7.62 (1H), 7.56-7.44(4H), 7.39(1H),7.33(1H)。
b) Synthesis of 3- (δ -carbolinyl) -phenylboronic acid pinacol ester: 5 g of N- (3-bromophenyl) -delta-carboline, 5 g of diboronic acid ester, 5 g of potassium acetate and 0.3 g of PdCl2(PPh3)2150 ml of 1, 4-dioxane is added into the three-neck flask, and the mixture is refluxed and stirred for 24 hours under the protection of nitrogen. After the reaction, the reaction mixture was extracted with ethyl acetate, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 4.2 g of a solid with a yield of 75%. Mass spectrum, theoretical value m/e, 370.2; found 370.2.1H-NMR(500MHz,CDC3): 8.61(1H), 8.45(1H), 7.97(1H), 7.93(1H), 7.67(1H), 7.62(2H), 7.51(1H), 7.43(1H), 7.37(1H), 7.32(1H), 1.36(12H)。
c) Refluxing and stirring 2g of 3- (delta-carbolinyl) -phenylboronic acid pinacol ester, 0.4g of 1,3, 5-tribromobenzene, 1.5 g of potassium carbonate, 30ml of distilled water, 70ml of toluene, 10ml of ethanol, 0.1g of palladium acetate and 0.4g of triphenylphosphine under the protection of nitrogen for 24 hours. After the reaction, extraction was performed with dichloromethane, washing with saturated brine, drying, concentration, and column chromatography to obtain b41.0 g as a solid with a yield of 70%. Mass spectrum, theoretical value m/e, 804.3; found 804.2.
Example four: preparation of Compound B8
a) Synthesis of N- (4-bromophenyl) -delta-carboline: the delta-carboline and the 1, 4-dibromobenzene are used as raw materials, and the synthesis method is the same as that of the N- (3-bromophenyl) -delta-carboline. Mass spectrum, theoretical value m/e, 323.2; found 323.1.
b) Synthesis of 4- (δ -carbolinyl) -phenylboronic acid pinacol ester: the synthesis method of the compound is the same as that of 3- (delta-carboline) -phenylboronic acid pinacol ester by taking N- (4-bromophenyl) -delta-carboline as a raw material. Mass spectrum, theoretical value m/e, 370.2; found 370.2.
c) Synthesis of B8: the synthesis method is the same as B4 by taking 4- (delta-carbolinyl) -phenyl boronic acid pinacol ester and 2,4, 6-trichlorooxazine as raw materials. Mass spectrum, theoretical value m/e, 807.3; found 807.3.
Example five: preparation of Compound B10
The synthesis method is the same as B4 by using 3- (delta-carbolinyl) -phenyl boronic acid pinacol ester and 2,4, 6-trichlorooxazine as raw materials. Mass spectrum, theoretical value m/e, 807.3; found 807.2.
Example six: preparation of Compound B16
Synthesis of B16: the synthesis method is the same as B4 by using 3- (delta-carbolinyl) -phenyl boronic acid pinacol ester and tri (4-bromophenyl) amine as raw materials. Mass spectrum, theoretical value m/e, 971.3; found 971.2.
Example seven: preparation of Compound B33
a) Synthesis of 3- (α -carbolinyl) -phenylboronic acid pinacol ester: the synthesis method of the alpha-carboline is the same as that of 3- (delta-carboline) -phenylboronic acid pinacol ester by taking the alpha-carboline as a raw material. Mass spectrum, theoretical value m/e, 370.2; found 370.1.
b) Synthesis of B33: the synthesis method is the same as B4 by using 3- (alpha-carbolinyl) -phenylboronic acid pinacol ester as a raw material. Mass spectrum, theoretical value m/e, 1091.4; the measured value. 1091.2
Example eight: preparation of Compound B34
Synthesis of compound B34: the synthesis method is the same as B4 by using 3- (delta-carbolinyl) -phenyl boronic acid pinacol ester as a raw material. Mass spectrum, theoretical value m/e, 1091.4; found 1091.3.
Example nine: preparation of Compound C2
a) Synthesis of N- (5-bromopyridin-2-yl) - δ -carboline: the synthesis method of the delta-carboline and the 2, 5-dibromopyridine are the same as the synthesis method of the N- (3-bromophenyl) -delta-carboline. Mass spectrum, theoretical value m/e, 323.0, 325.0; found 323.1, 325.1.
b) Synthesis of 2- (delta-carbolinyl) -5-pyridylboronic acid pinacol ester: the synthesis method of the compound is the same as that of the 3- (delta-carbolinyl) -phenylboronic acid pinacol ester by taking N- (5-bromopyridine-2-yl) -delta-carboline as a raw material. Mass spectrum, theoretical value m/e, 371.2; found 371.1.
c) Synthesis of C2: the synthesis method is the same as B4 by taking 2- (delta-carbolinyl) -5-pyridylboronic acid pinacol ester and 1,3, 5-tribromobenzene as raw materials. Mass spectrum, theoretical value m/e, 807.3; found 807.2.
Example ten: preparation of Compound C3
a) Synthesizing N- (6-bromopyridine-2-yl) -alpha-carboline: the synthesis method of the alpha-carboline and the 2, 6-dibromopyridine are the same as the synthesis method of the N- (3-bromophenyl) -delta-carboline. Mass spectrum with theoretical values of m/e, 323.0 and 325.0; found 323.1, 325.0.
b) Synthesis of C3: the synthesis method is the same as C2 with N- (6-bromopyridine-2-yl) -alpha-carboline and phenyl-1, 3, 5-triboric acid as raw materials. Mass spectrum, theoretical value m/e, 807.3; found 807.2.
Example eleven: preparation of Compound C8
Synthesis of compound C8: the synthesis method is the same as that of C2 by taking 2- (delta-carbolinyl) -4-pyridylboronic acid pinacol ester and 1,3, 5-tribromobenzene as raw materials. Mass spectrum, theoretical value m/e, 807.3; found 807.4.
Example twelve: preparation of Compound C9
Synthesis of compound C9: 3- (alpha-carbolinyl) -5-pyridylboronic acid pinacol ester and 1,3, 5-tribromobenzene are used as raw materials, and the synthesis method is the same as that of C2. Mass spectrum, theoretical value m/e, 807.3; found 807.3.
Example thirteen: preparation of Compound C17
Synthesis of compound C17: the synthesis method is the same as C2 with 2- (alpha-carbolinyl) -3-pyrazinylboronic acid pinacol ester and 1,3, 5-tribromobenzene as raw materials. Mass spectrum, theoretical value m/e, 810.2; found 810.1.
Example fourteen: preparation of Compound C39
Synthesis of compound C39: the synthesis method is the same as B34 by using 2- (alpha-carbolinyl) -6-pyrazinyl boronic acid pinacol ester as a raw material. Mass spectrum, theoretical value m/e, 1094.4; found 1094.3.
Example fifteen: preparation of Compound C40
Synthesis of compound C40: the synthesis method is the same as C39 by using 2- (delta-carbolinyl) -6-pyrazinyl boronic acid pinacol ester as a raw material. Mass spectrum, theoretical value m/e, 1094.4; found 1094.4.
The synthesized material is used as a host material to dope a blue phosphorescent material Firpic, so that the electroluminescent device is prepared. First, 5nm molybdenum trioxide (MoO) was deposited on the surface of the ITO-coated glass3) Evaporating 40nm of N, N '-di (1-naphthyl) -N, N' -diphenyl-1, 1 '-diphenyl-4, 4' -diamine (NPB) as a hole transport layer, evaporating 5nm of tris (4-carbazolylphenyl) amine (TCTA) as an electron blocking layer, doping the synthesized material as a main body with about 8% Firpic to form a 25nm light emitting layer, and finally sequentially evaporating an electron transport layer (Bphen, 40 nm), an interface layer (LiF, 1 nm) and a cathode (Al, 80 nm).
The following table is a list of OLED device properties:
| main body | Voltage of | Current efficiency | Power efficiency | External quantum efficiency | CIE x/y |
| A1 | 3.9 | 42 | 35 | 19.2% | 0.15/0.35 |
| A7 | 3.4 | 43 | 38 | 19.6% | 0.15/0.35 |
| B4 | 3.6 | 46 | 42 | 21.2% | 0.15/0.35 |
| B8 | 3.1 | 45 | 44 | 21.8% | 0.15/0.35 |
| B10 | 3.0 | 44 | 43 | 21.1% | 0.15/0.35 |
| B16 | 3.5 | 41 | 39 | 19.1% | 0.15/0.35 |
| B34 | 3.6 | 42 | 39 | 19.0% | 0.15/0.35 |
| C2 | 3.2 | 46 | 44 | 22.1% | 0.15/0.35 |
| C3 | 3.4 | 36 | 34 | 16.6% | 0.16/0.36 |
| C8 | 3.3 | 44 | 38 | 20.1% | 0.15/0.35 |
| C10 | 2.9 | 48 | 45 | 22.8% | 0.15/0.35 |
| C17 | 3.5 | 45 | 42 | 21.4% | 0.15/0.35 |
| C39 | 3.5 | 38 | 35 | 17.2% | 0.15/0.35 |
| C40 | 3.5 | 38 | 35 | 17.3% | 0.15/0.35 |
The foregoing detailed description is given by way of example only, to better enable one of ordinary skill in the art to understand the present patent, and is not to be construed as limiting the scope of this patent; any equivalent alterations or modifications made according to the spirit of the disclosure are included in the scope of the present patent.
Claims (6)
1. The carboline trisubstituted derivative is characterized by having a structural general formula as follows:
wherein, X1 and X2 are independently selected from C, N, and only one of X1 and X2 is an N atom; r is selected from any one of hydrogen atoms and cyano groups;
the structural formula of Ar1 in the structural general formula is as follows:
2. the carboline trisubstituted derivative according to claim 1, wherein when R is selected from the group consisting of hydrogen atoms, it has the following specific formula:
3. the use of the carboline trisubstituted derivative according to any one of claims 1 to 2, wherein said carboline trisubstituted derivative is used as an electron or hole transporting material.
4. The use of the carboline trisubstituted derivative according to any one of claims 1 to 2, wherein said carboline trisubstituted derivative is used as a luminophore.
5. The use of the carboline trisubstituted derivative according to claim 4, wherein said carboline trisubstituted derivative emits light alone as a light emitting layer or as a doped dye.
6. The use of the carboline tri-substituted derivative as claimed in claim 4, wherein said carboline tri-substituted derivative is doped to form exciplex luminescence.
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| CN110423214A (en) * | 2018-08-07 | 2019-11-08 | 广东聚华印刷显示技术有限公司 | Electron transport material and preparation method thereof and organic electroluminescence device |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006143845A (en) * | 2004-11-18 | 2006-06-08 | Konica Minolta Holdings Inc | Material for organic electroluminescent element, organic electroluminescent element, lighting equipment and display device |
| JP2006156445A (en) * | 2004-11-25 | 2006-06-15 | Konica Minolta Holdings Inc | Organic electroluminescent element, display device and lighting system |
| CN101414667A (en) * | 2003-04-23 | 2009-04-22 | 柯尼卡美能达控股株式会社 | Organic electroluminescent element and display |
| CN104059090A (en) * | 2014-06-27 | 2014-09-24 | 南京工业大学 | Synthesis method and application of pyridine and carboline derivative |
| CN104813744A (en) * | 2012-11-28 | 2015-07-29 | 柯尼卡美能达株式会社 | Transparent electrode, electronic device, and organic electroluminescence element |
| CN105051014A (en) * | 2013-03-22 | 2015-11-11 | 默克专利有限公司 | Materials for electronic devices |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006080271A (en) * | 2004-09-09 | 2006-03-23 | Konica Minolta Holdings Inc | Organic electroluminescence element, lighting system and display device |
-
2016
- 2016-07-26 CN CN201610591725.1A patent/CN106810569B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101414667A (en) * | 2003-04-23 | 2009-04-22 | 柯尼卡美能达控股株式会社 | Organic electroluminescent element and display |
| JP2006143845A (en) * | 2004-11-18 | 2006-06-08 | Konica Minolta Holdings Inc | Material for organic electroluminescent element, organic electroluminescent element, lighting equipment and display device |
| JP2006156445A (en) * | 2004-11-25 | 2006-06-15 | Konica Minolta Holdings Inc | Organic electroluminescent element, display device and lighting system |
| CN104813744A (en) * | 2012-11-28 | 2015-07-29 | 柯尼卡美能达株式会社 | Transparent electrode, electronic device, and organic electroluminescence element |
| CN105051014A (en) * | 2013-03-22 | 2015-11-11 | 默克专利有限公司 | Materials for electronic devices |
| CN104059090A (en) * | 2014-06-27 | 2014-09-24 | 南京工业大学 | Synthesis method and application of pyridine and carboline derivative |
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