CN109081791A - A kind of organic semiconducting materials and luminescent device - Google Patents

A kind of organic semiconducting materials and luminescent device Download PDF

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CN109081791A
CN109081791A CN201810879374.3A CN201810879374A CN109081791A CN 109081791 A CN109081791 A CN 109081791A CN 201810879374 A CN201810879374 A CN 201810879374A CN 109081791 A CN109081791 A CN 109081791A
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organic semiconductor
semiconductor material
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黄达
曹辰辉
孙晓媛
马腾达
陈少海
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ACC Acoustic Technologies Shenzhen Co Ltd
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Abstract

The invention belongs to electroluminescent material technical field, a kind of organic semiconducting materials and luminescent device are disclosed.Organic semiconducting materials provided by the present invention include at least one host material and at least one dopant material, and host material has structure shown in logical formula (I), dopant material has structure shown in logical formula (II) or logical formula (III).With luminescent device prepared by semiconductor material of the invention, open that bright voltage is remarkably decreased, luminous efficiency significantly improves.Semiconductor material of the invention is significant for the efficiency raising of navy blue phosphorescent devices, is also to be expected for the application in sky blue phosphorescent devices, green phosphorescent device and red phosphorescent device according to the principle of energy transmission.

Description

Organic semiconductor material and light-emitting device
Technical Field
The invention belongs to the technical field of electroluminescent materials, and particularly relates to an organic semiconductor material and a light-emitting device.
Background
Organic materials are utilized to prepare various functional devices, and particularly photoelectric response functional devices such as common organic electroluminescent devices, organic solar cell devices, organic field effect transistor devices and organic photosensitive sensor devices are increasingly paid more attention by people.
An organic electroluminescent device is a device technology for realizing electric light emission by introducing one or more layers of organic films into a cathode and an anode, can realize ultrathin, flexible and transparent performances, and is improved year by year in the application of flat panel display and lighting industries.
The organic electroluminescent device structure in the industry can be realized by different technologies in order to realize high-efficiency and long-life luminescence. An organic electroluminescent device structure comprises at least an anode, a cathode and an organic layer. The organic layer may be further divided into a light emitting layer for emission spectrum and a functional layer for auxiliary light emission. For the light emitting layer of the emission spectrum, one way is to improve the efficiency and lifetime by doping with host and guest. The host material receives energy and transmits the energy to the object, and the object material emits corresponding spectrum after receiving the energy. Different host and guest materials can realize different colors of luminescence. CBP is an example of a common green host material, and ir (ppy)3 and AlQ3 are examples of a common green guest material.
The number of layers and functions of the functional layer for assisting light emission are not limited as long as the functional layer can assist light emission and improve various properties. One functional layer is a hole transport layer that functions as a hole transport; one functional layer is an electron transport layer that serves as an electron transport. The hole transport layer may have both a hole injection function and the electron transport layer may have both an electron injection function.
It is well known in the art that a single structure of an organic semiconductor is doped, and the change in the electrical properties of the doped organic semiconductor is significant, such as when the light-emitting layer is in a doped form. When a doped semiconductor is applied to a light emitting device as a light emitting layer, the doped organic semiconductor is referred to as a host material and the doped material is referred to as a guest material. When a doped semiconductor is applied as a functional layer to a light emitting device, the doped organic semiconductor is referred to as a host material. When the host material plays a role in hole transport, the corresponding doped material is called a P-type doped material, and when the host material plays a role in electron transport, the corresponding doped material is called an n-type doped material. When the functional layers of the light emitting device are prepared by doping, the device is referred to as a PIN device. The chemical review (chem. rev.2007,107,1233-1271) explains PIN in detail.
The doping material is a compound having good electron donor properties or a compound having good acceptor properties. Here, the term compound refers to small organic molecules bonded through covalent bonds between atoms, polymers bonded through covalent bonds, complexes having a metal coordinate bond, and organometallic salts.
Since the work function of ITO has a large energy level difference with a hole transport material, the energy barrier for hole injection is high. In a hole transport layer formed by a single semiconductor, a P-type doping material is introduced, and the importance degree is higher and higher. Like the light-emitting layer, when the functional layer adopts a doped structure, the matching property is important.
Patent CN102892859 provides a solution, the matrix material of which is terphenyl aromatic amine.
Patent TW201341347 provides a solution, the matrix material of which is an aromatic amine of the terphenyl type.
Patent TW201540695A provides a solution in which the matrix material is a fluorenyl aromatic amine.
The patents TW201638366A, TWI508342B, TWI423945B, CN101330129B, CN101728485B provide a series of p-type doped materials whose function is uncertain for the specific host material.
However, for high-energy light-emitting systems, in particular deep-blue light-emitting material systems, corresponding auxiliary semiconductor materials which improve the electrical properties are lacking.
Disclosure of Invention
The invention aims to provide a luminescent material capable of obviously improving the efficiency of a device and the device thereof.
In order to solve the above technical problems, embodiments of the present invention provide an organic semiconductor material comprising at least one host material and at least one dopant material,
the matrix material has a structure represented by general formula (I):
wherein,
l is an arylene group;
X1、X2each independently represents O, S or Se;
R1、R2、R3、R4、R5、R6each independently represents hydrogen, deuterium, halogen, alkyl, alkoxy, aryl, heteroaryl or heteroaryloxy;
the doping material has a structure shown in a general formula (II) or a general formula (III):
wherein,
m represents an integer of 1 to 6;
A1、A2、A3、A4、A5each independently represents C (A)x)(Ay) Said A isx、AyRepresents an aryl or heteroaryl group containing at least one electron-withdrawing group of F, CF3、CF2CF3CN, OCN, SCN, NCS or NCO.
Preferably, the sum of the numbers of electron withdrawing groups other than fluorine atoms in the general formula (II) is two or more times the value of (m + 2).
Preferably, m in the general formula (II) is 1.
Preferably, the matrix material has a symmetrical structure as shown in general formula (IV):
wherein,
l is an arylene group;
X1、X2each independently represents O, S or Se;
r', R "each independently represent hydrogen, deuterium, halogen, alkyl, alkoxy, aryl, heteroaryl or heteroaryloxy.
Preferably, L is phenyl, biphenyl, naphthyl, fluorenyl, spirofluorenyl, spirosilafluorenyl, dibenzothienyl, dibenzofuranyl, or carbazolyl.
Preferably, the compound of formula (I) has a structure selected from one of the following:
preferably, the compound of formula (II) has a structure selected from one of the following:
preferably, the compound of formula (III) has a structure selected from one of the following:
embodiments of the present invention also provide a light emitting device having at least one cathode, at least one anode, and at least one organic light emitting layer, and the light emitting layer includes the above-described organic semiconductor material.
Embodiments of the present invention also provide a dopant material having a structure represented by general formula (II) or general formula (III):
wherein,
m represents an integer of 1 to 6;
A1、A2、A3、A4、A5each independently represents C (A)x)(Ay) Said A isx、AyRepresents an aryl or heteroaryl group containing at least one electron-withdrawing group of F, CF3、CF2CF3CN, OCN, SCN, NCS or NCO;
the total number of the electron-withdrawing groups other than fluorine atoms in the general formula (II) is two times or more than two times the number of (m + 2).
Compared with the prior art, the deep blue device adopting the organic semiconductor material has the advantages that the starting voltage is obviously reduced, and the efficiency of a phosphorescent device is obviously improved due to the selection of a proper host material.
[ description of the drawings ]
In order to more clearly illustrate the technical solutions in the embodiments of the present invention, the drawings needed to be used in the description of the embodiments are briefly introduced below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and other drawings can be obtained by those skilled in the art without inventive efforts, wherein:
fig. 1 is a schematic structural view of a light-emitting device in an embodiment of the present invention;
wherein, 11-the first electrode, 12-the hole transport layer, 13-the luminescent layer, 14-the electron transport layer, 15-the second electrode.
Detailed Description
The disclosure may be understood more readily by reference to the following detailed description and the examples included therein. Before the present compounds, devices, and/or methods are disclosed and described, it is to be understood that they are not limited to the particular synthetic methods (otherwise specified), or to the particular reagents (otherwise specified), as such can, of course, vary. It is also to be understood that the terminology used herein is for the purpose of describing particular aspects only and is not intended to be limiting. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing, the exemplary methods and materials are described below.
Organic semiconductor materials:
in a specific embodiment of the present invention, there is provided an organic semiconductor material comprising at least one host material and at least one dopant material, the host material having a structure represented by general formula (I):
wherein L is an arylene group; x1、X2Each independently represents O, S or Se; r1、R2、R3、R4、R5、R6Each independently represents hydrogen, deuterium, halogen, alkyl, alkoxy, aryl, heteroaryl or heteroaryloxy;
the doping material has a structure shown in a general formula (II) or a general formula (III):
wherein m represents an integer of 1 to 6; a. the1、A2、A3、A4、A5Each independently represents C (A)x)(Ay) Said A isx、AyRepresents an aryl or heteroaryl group containing at least one electron-withdrawing group of F, CF3、CF2CF3CN, OCN, SCN, NCS or NCO.
In some embodiments of the invention, the sum of the number of electron withdrawing groups other than fluorine atoms in formula (II) is two or more times the value of (m + 2).
In some embodiments of the invention, m in formula (II) is 1.
In some embodiments of the invention, the matrix material has a symmetrical structure as shown in formula (IV):
wherein L is an arylene group; x1、X2Each independently represents O, S or Se; r', R "each independently represent hydrogen, deuterium, halogen, alkyl, alkoxy, aryl, heteroaryl or heteroaryloxy.
In some embodiments of the invention, L is phenyl, biphenyl, naphthyl, fluorenyl, spirofluorenyl, spirosilafluorenyl, dibenzothienyl, dibenzofuranyl, or carbazolyl.
In some embodiments of the invention, the compound of formula (I) has a structure selected from one of the following:
in some embodiments of the invention, the compound of formula (II) has a structure selected from one of the following:
in some embodiments of the invention, the compound of formula (III) has a structure selected from one of the following:
embodiments of the present invention also provide a light emitting device having at least one cathode, at least one anode and at least one organic light emitting layer, and the light emitting layer comprises the above-described organic semiconductor material.
Embodiments of the present invention also provide a doped material having a structure represented by formula (II) or formula (III):
wherein m represents an integer of 1 to 6; a. the1、A2、A3、A4、A5Each independently represents C (A)x)(Ay) Said A isx、AyRepresents an aryl or heteroaryl group containing at least one electron-withdrawing group of F, CF3、CF2CF3CN, OCN, SCN, NCS or NCO; the total number of the electron-withdrawing groups other than fluorine atoms in the general formula (II) is two times or more than two times the number of (m + 2).
Preparation of organic semiconductor material:
the method A comprises the following steps: general synthetic route to the general formula (I)
The preparation method of the compound with the dibenzofuran structure comprises the steps of mixing dibenzofuran boric acid and a brominated aromatic compound in tetrahydrofuran, adding sodium carbonate and palladium acetate serving as a catalyst, heating to react for 24 hours, cooling, extracting with dichloromethane, purifying by column chromatography to obtain aryl-substituted dibenzofuran, reacting the obtained aryl-substituted dibenzofuran with liquid bromine in the low-temperature tetrahydrofuran for 12 hours in the presence of butyl lithium, carrying out aftertreatment to obtain a bromine-substituted dibenzofuran compound, reacting the bromine-substituted dibenzofuran compound with corresponding amine in dry toluene for 24 hours under the conditions of palladium acetate, ligand tBu3P and alkali tBuONa, cooling, extracting with dichloromethane, and purifying by column chromatography to obtain the compound shown in the general formula (I).
The method B comprises the following steps: general synthetic methods of general formula (II).
The synthesis method of the general formula (II) can be referred to in U.S. society of chemistry J.Am.chem.Soc.,1976,98, 610-one 611 and patent US 2012223296. More specifically, the following method is exemplified.
207mmol of cyanoacetate was dissolved in 50mL of dimethylformamide, and the solution was added with stirring to a solution of 207mmol of fluoroaromatic compound and 250mmol of potassium carbonate in 370mmol of dimethylformamide and stirred at room temperature for 48 hours. The mixture was then poured into 1L of ice water. Under vigorous stirring, 100mL of concentrated acetic acid was added and the reaction was stirred for 4 hours. Extracted three times with dichloromethane. The combined organic phases are dried over magnesium sulfate and the solvent is removed in vacuo to give the arylcyanoacetic acid esters. The entire quantity of arylcyanoacetate, 4.15mL of concentrated sulfuric acid and 84mL of acetic acid (50%) was heated at reflux for 16 hours. After cooling, the whole was poured into 120mL of ice-water and stirred for 30 minutes. Extracted three times with dichloromethane. The combined organic phases were then washed with 100mL of water and 100mL of saturated sodium carbonate solution. After drying over magnesium sulfate, the solvent is removed by vacuum-pumping to obtain aryl acetonitrile. Lithium hydride (98%) was suspended in 60mL of ethylene glycol dimethyl ether and cooled to 0 ℃. To 60mL of ethylene glycol dimethyl ether was added 152mmol of aryl acetonitrile. Naturally warming to room temperature, stirring at room temperature for 15 minutes, cooling to 0 ℃ again, and slowly adding 40mmol of tetrachlorocyclopropene dropwise. The mixture was then added to 1.2L of ice water and acidified with hydrochloric acid to pH 1. Extracted three times with dichloromethane. The organic phases were combined and washed successively with saturated brine, water, sodium bicarbonate solution and water. Drying with magnesium sulfate, and removing the solvent by vacuumizing to obtain the aryl cyclopropene. Aryl cyclopropene was dissolved in 1.4L of glacial acetic acid, and a mixed solution consisting of 360mL of hydrobromic acid (48%) and 120mL of nitric acid (65%) was added dropwise with stirring. Stirring for 1.5 hours, filtering, washing with water three times, drying in vacuo and finally purifying by gradient sublimation to give the compound of formula (II).
The method C comprises the following steps: general synthetic methods of the general formula (III).
The synthesis method of method C can be referred to in U.S. society of chemistry J.Am.chem.Soc.,1976,98, 610-219, Chem.Commun.2008, 217-219 and U.S. Pat. No. 2012223296. More specifically, the following method is exemplified.
207mmol of cyanoacetate was dissolved in 50mL of dimethylformamide, and the solution was added with stirring to a solution of 207mmol of fluoroaromatic compound and 250mmol of potassium carbonate in 370mmol of dimethylformamide and stirred at room temperature for 48 hours. The mixture was then poured into 1L of ice water. Under vigorous stirring, 100mL of concentrated acetic acid was added and the reaction was stirred for 4 hours. Extracted three times with dichloromethane. The combined organic phases are dried over magnesium sulfate and the solvent is removed in vacuo to give the arylcyanoacetic acid esters. The entire quantity of arylcyanoacetate, 4.15mL of concentrated sulfuric acid and 84mL of acetic acid (50%) was heated at reflux for 16 hours. After cooling, the whole was poured into 120mL of ice-water and stirred for 30 minutes. Extracted three times with dichloromethane. The combined organic phases were then washed with 100mL of water and 100mL of saturated sodium carbonate solution. After drying over magnesium sulfate, the solvent is removed by vacuum-pumping to obtain aryl acetonitrile. Adding 46mmol of aryl acetonitrile into anhydrous 200mL of tetrahydrofuran and 200mL of anhydrous ether solution, cooling to-78 ℃, adding 46mmol of elemental iodine under the protection of nitrogen, then dropwise adding a methanol solution containing 105mmol of sodium methoxide, stirring for 30 minutes, and then adding a mixed solution (volume ratio is 1:3) containing 2mol/L hydrochloric acid solution and methanol. Stirring for 1.5 hours, filtering, washing with water three times, drying in vacuo and finally purifying by gradient sublimation to give the compound of formula (III).
Synthesis example:
example 1 Synthesis of S001
Bromobenzene (10.0mmol), dibenzofuran-4-boronic acid (12.0mmol), palladium acetate (0.3mmol) and sodium carbonate (20.00mmol) were dissolved in 50mL of tetrahydrofuran, reacted at 65 ℃ for 24 hours, cooled, water and dichloromethane were added, and the organic layer was concentrated by column chromatography to give an intermediate (S001-3). S001-3(5mmol), liquid bromine (6mmol) and butyl lithium (5mmol) are dissolved in 30mL tetrahydrofuran, and the intermediate product S001-4 is obtained after reaction for 12h at-78 ℃. Dissolving 2, 6-dibromo spirobifluorene (10mmol) and aniline (20mmol) in 100mL of dry toluene, adding a catalyst of palladium acetate, a ligand tBu3P, an alkali tBuONa, reacting for 12h under the condition of nitrogen, cooling, and extracting with dichloromethane. Then carrying out column chromatography to obtain an intermediate product S001-7. S001-4(5mmol) and S001-7(5mmol) are dissolved in 50mL of dry toluene, palladium acetate, a ligand tBu3P, a base tBuONa are added to react for 12h under the nitrogen condition, dichloromethane is extracted after cooling, and the final product S001(2.6mmol) is obtained after column chromatography, wherein the yield is 52.0%. MS (ESI-TOF): the nucleus ratio M/z was found to be 983.16[ M + ].
Example 2: synthesis of S002
Dissolving 2, 6-dibromo spirobifluorene (10mmol) and 4-aminobiphenyl (20mmol) in 100mL of dry toluene, adding a catalyst of palladium acetate, a ligand tBu3P, an alkali tBuONa, reacting for 12h under the nitrogen condition, cooling, and extracting with dichloromethane. Then carrying out column chromatography to obtain an intermediate product S002-7. Dissolving S001-4(5mmol) and S002-7(5mmol) in 50mL of dry toluene, adding palladium acetate, ligand tBu3P, alkali tBuONa, reacting for 12h under the nitrogen condition, cooling, extracting with dichloromethane, and carrying out column chromatography to obtain the final product S002(2.3mmol), wherein the yield is 46.0%. MS (ESI-TOF) the proton/nuclear ratio M/z was found to be 1135.35[ M + ].
Example 3 Synthesis of S027
Dissolving 2, 7-dibromo-9, 9-dimethylfluorene (10mmol) and aniline (20mmol) in 100mL of dry toluene, adding a catalyst of palladium acetate, a ligand tBu3P, an alkali tBuONa, reacting for 12h under the nitrogen condition, cooling, and extracting with dichloromethane. Then carrying out column chromatography to obtain an intermediate product S027-7. S001-4(5mmol) and S027-7(5mmol) are dissolved in 50mL of dry toluene, palladium acetate, ligand tBu3P, base tBuONa are added to react for 12h under the nitrogen condition, dichloromethane is extracted after cooling, and the final product S027(2.1mmol) is obtained after column chromatography, wherein the yield is 42.0%. MS (ESI-TOF) the proton/nuclear ratio M/z was found to be 861.04[ M + ].
Example 4 Synthesis of S028
Dissolving 2, 7-dibromo-9, 9-dimethylfluorene (10mmol) and 4-aminobiphenyl (20mmol) in 100mL of dry toluene, adding a catalyst of palladium acetate, a ligand tBu3P, an alkali tBuONa, reacting for 12h under the nitrogen condition, cooling, and extracting with dichloromethane. Then carrying out column chromatography to obtain an intermediate product S028-7. S001-4(5mmol) and S028-7(5mmol) are dissolved in 50mL of dry toluene, palladium acetate, ligand tBu3P, alkali tBuONa are added for reaction for 12h under the condition of nitrogen, dichloromethane is extracted after cooling, and the final product S028(2.5mmol) is obtained after column chromatography, wherein the yield is 50.0%. MS (ESI-TOF) the proton/nuclear ratio M/z was found to be 1013.23[ M + ].
Example 5 Synthesis of P-7
Referring to method B, wherein the cyanoacetate is ethyl cyanoacetate and the fluoroaromatic compound is pentacyanobenzene. The molecular ion peak of the mass spectrum of compound P-7 was 756.
Example 6 Synthesis of P-25
Referring to method B, wherein the cyanoacetate is ethyl 4-cyanotetrafluorophenyl acetate and the fluoroaromatic compound is cyanopentafluorobenzene. The molecular ion peak of the mass spectrum of compound P-25 was 1116.
Example 7 Synthesis of P-34
Referring to method C, wherein the cyanoacetate is ethyl cyanoacetate, the fluoroaromatic compound 4-pentacyanophenyl-2, 3,5, 6-tetracyanofluorobenzene. The molecular ion peak of the mass spectrum of the compound P-34 is 832.
Light emitting device and performance evaluation examples
Fig. 1 is a schematic structural diagram of a light emitting device according to the present invention.
The light-emitting device comprises a first electrode 11, a hole transport layer 12, a light-emitting layer 13, an electron transport layer 14 and a second electrode 15 which are sequentially deposited. The hole transport layer 12, the light emitting layer 13, and the electron transport layer 14 are all organic layers, and the first electrode 11 and the second electrode 15 are electrically connected to each other.
The light emitting layer 13 may have only one material, making the light emitting device an undoped device. The light-emitting layer 13 may have two or more materials, making the light-emitting device a doped device. When a doped device is employed, the proportion of the doping material in the light-emitting layer 13 is not limited. When a doped device is used, the doping ratio is not limited, and is generally in the range of 0.1 to 50%, preferably 1 to 20%, and more preferably 2 to 10%.
The hole transport layer 12 is made of a material having a hole transport ability, and there is no specific requirement for the compound structure of the hole transport layer as long as the introduced holes can be transported to the light emitting layer 13, and an aromatic amine organic compound is generally selected as the hole transport layer. The hole transport layer 12 may be one layer or may be a plurality of layers. The hole transport layer or layers 12 may have hole injection properties, electron blocking properties, or exciton blocking properties, respectively or simultaneously. The hole transport layer 12 may be of two or more materials, making the light emitting device a PIN device. When a PIN device is employed, the proportion of doping material in the hole transport layer 12 is not limited. The range is generally 0.1 to 50%, preferably 1 to 20%, more preferably 2 to 10%.
The electron transport layer 14 is made of a material having an electron transport ability, and there is no particular requirement for the compound structure of the electron transport layer as long as it can transport the introduced electrons to the light emitting layer. As the compound structure of the electron transport layer 14, a nitrogen-containing heterocyclic compound, a spiro aromatic compound composed of a hydrocarbon element, or a metal complex may be selected. The electron transport layer 14 may be one layer or may be a plurality of layers. The one or more electron transport layers 14 may have one or more of electron injection properties, hole blocking properties, or exciton blocking properties, respectively or simultaneously. Similarly, the electron transport layer 14 may also be made of two or more materials, such that the light emitting device is a PIN device. When a PIN device is used, the proportion of doping material in the electron transport layer 14 is not limited. The range is generally 0.1 to 50%, preferably 1 to 20%, more preferably 2 to 10%.
In order to schematically demonstrate the excellent characteristics of the compound provided by the present invention as a material for a light emitting device, the light emitting device was designed according to the following structure: anode/first hole transport layer/second hole transport layer/light emitting layer/electron transport layer/cathode. The anode is an ITO electrode, the first hole transport layer contains a host material shown in a general formula (I) and a doping material shown in a general formula (II), the thickness of the first hole transport layer is 10nm, wherein the compound shown in the general formula (II) accounts for 8% of the total weight of the first hole transport layer material, the second hole transport layer is a compound shown in the general formula (I), the thickness of the second hole transport layer is 50nm, the light-emitting layer contains a host material (9,9 ' (2, 2' -dimethylbiphenyl-4, 4 ' -diyl) di (9H) carbazole) and a guest material (di [3, 5-difluoro-2- (2-pyridyl) phenyl ] [2- (2H-tetrazol-5-yl) pyridine ] iridium), the thickness of the light-emitting layer is 20nm, the guest material accounts for 3% of the total weight of the light-emitting layer material, and the electron transport layer is a LiQ-doped electron transport material ((3, h ] acridin-7-yl) phenyl) diphenylphosphine oxide), wherein the weight percentage of LiQ in the whole electron transport layer material is 15%, and the cathode is an Al cathode.
The following table shows the matrix material, dopant material composition and performance data for each device:
No.1 matrix material Doping material Turn-on voltage External quantum efficiency
1 S013 P-7 2.2V 9.4％
2 S007 P-7 2.3V 8.9％
3 S001 P-7 2.5V 8.6％
4 S013 P-25 2.4V 8.8％
5 S013 P-34 2.4V 8.5％
CC-1 H-CC1 P-7 2.6V 6.4％
CC-1 H-CC1 P-CC 2.7V 6.6％
CC-2 H-CC2 P-CC 2.7V 5.8％
The comparative example used the dopant material P-CC of (2E,2 'E) -2,2' - (cyclopropane-1, 2, 3-trienylidene) tris [ 4-cyano-2, 3,5, 6-tetrafluorophenylacetonitrile ], and the host materials of H-CC1 and H-CC 2.
As can be seen from the data in the above table, the light-emitting device of the present invention has a drop in the turn-on voltage of at least 7% and an increase in the light-emitting efficiency of at least 60% as compared to the comparative example. It can be seen that the efficiency improvement of the present invention for deep blue phosphorescent devices is significant. Improvements to sky blue, green, and red phosphorescent devices are also contemplated, based on the principles of energy transfer.
The foregoing is merely a preferred embodiment of the invention and is not intended to limit the invention in any manner. Those skilled in the art can make many possible variations and modifications to the disclosed solution, or modify equivalent embodiments using the teachings set forth above, without departing from the scope of the claimed solution. Therefore, any simple modification, equivalent change and modification made to the above embodiments according to the technical essence of the present invention are still within the protection scope of the technical solution of the present invention, unless the content of the technical solution of the present invention is departed from.

Claims (10)

1. An organic semiconductor material comprising at least one host material and at least one dopant material,
the matrix material has a structure represented by general formula (I):
wherein,
l is an arylene group;
X1、X2each independent earth surfaceO, S or Se;
R1、R2、R3、R4、R5、R6each independently represents hydrogen, deuterium, halogen, alkyl, alkoxy, aryl, aryloxy, heteroaryl or heteroaryloxy;
the doping material has a structure shown in a general formula (II) or a general formula (III):
wherein,
m represents an integer of 1 to 6;
A1、A2、A3、A4、A5each independently represents C (A)x)(Ay) Said A isx、AyRepresents an aryl or heteroaryl group containing at least one electron-withdrawing group of F, CF3、CF2CF3CN, OCN, SCN, NCS or NCO.
2. The organic semiconductor material according to claim 1, wherein the total number of the electron-withdrawing groups other than fluorine atoms in the general formula (II) is two or more times the value of (m + 2).
3. The organic semiconductor material according to claim 1, wherein m in the general formula (II) is 1.
4. The organic semiconductor material of claim 1, wherein the host material has a symmetrical structure as shown in formula (IV):
wherein,
l is an arylene group;
X1、X2each independent earth surfaceO, S or Se;
r 'and R' each independently represent hydrogen, deuterium, halogen, alkyl, alkoxy, aryl, aryloxy, heteroaryl or heteroaryloxy.
5. The organic semiconductor material of claim 1, wherein L is phenyl, biphenyl, naphthyl, fluorenyl, spirofluorenyl, spirosilafluorenyl, dibenzothienyl, dibenzofuranyl, or carbazolyl.
6. The organic semiconductor material according to claim 1, wherein the compound of formula (I) has a structure selected from one of the following:
7. the organic semiconductor material according to claim 1, wherein the compound of formula (II) has a structure selected from one of the following:
8. the organic semiconductor material according to claim 1, wherein the compound of formula (III) has a structure selected from one of the following:
9. a light-emitting device having at least one cathode, at least one anode and at least one organic light-emitting layer, characterized in that the light-emitting layer comprises an organic semiconductor material according to any one of claims 1 to 8.
10. A doped material having a structure according to formula (II) or formula (III):
wherein,
m represents an integer of 1 to 6;
A1、A2、A3、A4、A5each independently represents C (A)x)(Ay) Said A isx、AyMeans comprising at least one suctionAryl or heteroaryl of an electron group of F, CF3、CF2CF3CN, OCN, SCN, NCS or NCO;
the total number of the electron-withdrawing groups other than fluorine atoms in the general formula (II) is two times or more than two times the number of (m + 2).
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