CN107573328B - Indenoimidazole compound, material containing same and organic electroluminescent device - Google Patents
Indenoimidazole compound, material containing same and organic electroluminescent device Download PDFInfo
- Publication number
- CN107573328B CN107573328B CN201710851663.8A CN201710851663A CN107573328B CN 107573328 B CN107573328 B CN 107573328B CN 201710851663 A CN201710851663 A CN 201710851663A CN 107573328 B CN107573328 B CN 107573328B
- Authority
- CN
- China
- Prior art keywords
- organic electroluminescent
- compound
- indenoimidazole
- electroluminescent device
- radical
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses an indenoimidazole compound, which has a structural formula shown as a formula I:
the invention also discloses a material containing the indenoimidazole compound and an organic electroluminescent device containing the indenoimidazole compound. The indenoimidazole compound provided by the invention has excellent carrier transmission capability, and an organic electroluminescent device prepared by using the material can obviously reduce the starting voltage and improve the luminous efficiency and brightness; the indenoimidazole compound has better film-forming property, and the material synthesis and purification method is simple and suitable for large-scale production, and is ideal as the electronic transmission material of the organic electroluminescent deviceAnd (4) selecting.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent materials. And more particularly to indenoimidazole derivatives, materials and organic electroluminescent devices comprising the same.
Background
Organic electroluminescence (abbreviated as OLED) and related research firstly discovered the electroluminescence phenomenon of organic compound single crystal anthracene in pope et al as early as 1963. Kodak company of the United states of 1987 made an amorphous film device by evaporating small organic molecules, and reduced the driving voltage to within 20V. The device has the advantages of ultra-light weight, full curing, self luminescence, high brightness, wide viewing angle, high response speed, low driving voltage, low power consumption, bright color, high contrast, simple process, good temperature characteristic, soft display and the like, and can be widely applied to flat panel displays and surface light sources, so the device is widely researched, developed and used.
Through the development of twenty years, the organic EL material has comprehensively realized red, blue and green luminescence, and the application field has also been expanded from small molecules to the fields of high molecules, metal complexes and the like. In recent years, organic electroluminescent display technologies have become mature, and some products have entered the market, but in the course of industrialization, many problems still need to be solved, especially for various organic materials used for manufacturing devices, there are many problems that are still unsolved, such as carrier injection and transport performance, electroluminescent performance of materials, service life, color purity, matching between various materials and between various electrodes, and the like. Especially, the light emitting device has not yet achieved practical requirements in terms of luminous efficiency and service life, which greatly limits the development of OLED technology. The metal complex phosphorescent material utilizing triplet state luminescence has high luminescence efficiency, and green and red materials of the metal complex have already met the use requirements, but the blue materials of the metal complex cannot meet the use requirements due to the special electronic structure characteristics of the metal complex.
Through the development of twenty years, the organic EL material has comprehensively realized red, blue and green luminescence, and the application field has also been expanded from small molecules to the fields of high molecules, metal complexes and the like. In recent years, organic electroluminescent display technologies have become mature, and some products have entered the market, but in the course of industrialization, many problems still need to be solved, especially for various organic materials used for manufacturing devices, there are many problems that are still unsolved, such as carrier injection and transport performance, electroluminescent performance of materials, service life, color purity, matching between various materials and between various electrodes, and the like.
Therefore, it is desirable to provide an indenoimidazole compound that improves electron mobility, lowers driving voltage, and improves device brightness and efficiency, and at least one of the above problems is solved.
Disclosure of Invention
One object of the present invention is to provide an indenoimidazole compound.
It is another object of the present invention to provide a material comprising an indenoimidazole compound.
A third object of the present invention is to provide an organic electroluminescent device.
In order to achieve the first purpose, the invention adopts the following technical scheme:
an indenoimidazole compound, the structural formula of which is shown in formula I:
wherein R is1、R2、R3、R4Each independently represents hydrogen, deuterium hydrogen, a compound containing C1～C8Linear or branched alkyl of (C)1～C8Linear or branched alkoxy, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Aromatic vinyl, substituted or unsubstituted C6-C60Condensed ring aromatic radicals, substituted or notSubstituted C6-C60Arylamino, substituted or unsubstituted C6-C60Nitrogen atom-containing condensed ring aryl group, substituted or unsubstituted C6-C60Condensed ring aromatic group containing sulfur or oxygen atom, substituted or unsubstituted C6-C60Condensed ring aromatic group containing phosphorus or silicon or boron atom, and substituted or unsubstituted C2-C60Any one of heterocyclic aryl;
Ar1、Ar2each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted carbazolyl group, and a substituted or unsubstituted C2-C60Any one of heterocyclic aryl;
n represents an integer of 1 to 5.
Preferably, said substituted or unsubstituted C2-C60The cyclic structure of the heterocyclic aryl group contains N, O, S atoms.
Preferably, said R is1、R2、R3、R4、Ar1、Ar2In the group, the C2-C60Each of the heterocyclic aryl groups of (a) is independently selected from one or more of the following structures II-1 to II-15:
wherein Z is1、Z2、Z3Each independently represents hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a carboxylate thereof, a sulfonic group or a sulfonate thereof, a phosphoric group or a phosphate thereof, C1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, C1-C60Alkoxy radical, C3-C60Cycloalkyl radical, C3-C60Cycloalkenyl radical, C6-C60Aryl radicals containing at least one-F, -CN or C1-C10C of alkyl6-C60Aryl, substituted or unsubstituted C6-C60Aryloxy, substituted or unsubstituted C6-C60An arylthioether group, or a substituted or unsubstituted C2-C60A heterocyclic aryl group;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
T1represents oxygen or sulfur;
Preferably, Ar is1Structures comprising, but not limited to, the following III-1 to III-16:
wherein Z is11And Z12Each independently represents hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a carboxylate thereof, a sulfonic group or a sulfonate thereof, a phosphoric group or a phosphate thereof, C1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, C1-C60Alkoxy radical, C3-C60Cycloalkyl radical, C3-C60Cycloalkenyl radical, C6-C60Aryl radicals containing at least one-F, -CN or C1-C10C of alkyl6-C60Aryl, substituted or unsubstituted C6-C60Aryloxy, substituted or unsubstituted C6-C60An arylthioether group, or a substituted or unsubstituted C2-C60A heterocyclic aryl group;
Z13represents substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Aryloxy, substituted or unsubstituted C6-C60An arylthioether group, or a substituted or unsubstituted C2-C60A heterocyclic aryl group;
y1 represents an integer of 1 to 4; y2 represents an integer of 1 to 6; y3 represents an integer of 1 to 3; y4 represents an integer of 1 to 5.
Preferably, the indenoimidazole compound with the structural formula I is specifically any one of the following compounds CJH-P01 to CJH-P84, but is not limited to the following structures:
to achieve the second object, the present invention also provides a material, the raw material of which comprises one or more of the above indenoimidazole compounds.
Preferably, the material is an organic electroluminescent material. The material comprising the compound of the present invention has the ability of carrier transport.
In order to achieve the third object, the invention also provides an organic electroluminescent device, and the material of the organic electroluminescent device comprises one or more of the indenoimidazole compounds. The organic electroluminescent device can be a top-emitting light device and a bottom-emitting light device. The structure and the preparation method of the organic electroluminescent device are not limited in the invention. The organic electroluminescent device prepared by the compound can reduce the starting voltage and improve the luminous efficiency and brightness.
Preferably, the organic electroluminescent device comprises a substrate, an anode layer disposed on the substrate, a hole transport layer disposed on the anode layer, an organic light emitting layer disposed on the hole transport layer, an electron transport layer disposed on the organic light emitting layer, and a cathode layer disposed on the electron transport layer.
Preferably, the material of at least one of the hole transport layer, the organic light emitting layer and the electron transport layer in the organic electroluminescent device comprises one or more of the indenoimidazole compounds. The invention does not limit the materials of other layers in the organic electroluminescent device.
Preferably, the substrate is made of glass or a flexible substrate.
Preferably, the material of the anode layer is an inorganic material or an organic conductive polymer; wherein the inorganic material is indium tin oxide, zinc oxide, tin zinc oxide, gold, silver or copper; the organic conductive polymer is selected from at least one of polythiophene, sodium polyvinyl benzene sulfonate and polyaniline.
Preferably, the material of the hole transport layer further includes, but is not limited to, one or more of the following compounds:
preferably, the material of the organic light emitting layer further includes, but is not limited to, one or more of the following compounds:
preferably, the material of the organic light emitting layer further includes a dopant material including red, green and blue dopant materials.
Preferably, the blue doping material includes, but is not limited to, one or more of the following compounds:
preferably, the red doping material includes, but is not limited to, one or more of the following compounds:
preferably, the green doping material includes, but is not limited to, one or more of the following compounds:
preferably, the material of the electron transport layer further includes, but is not limited to, one or more of the following compounds:
preferably, the material of the cathode layer is selected from any one or an alloy consisting of any two of the following elements or fluorides of the following elements: lithium, magnesium, silver, calcium, strontium, aluminum, indium, copper, gold, and silver.
Preferably, a hole injection layer is further arranged between the anode layer and the hole transport layer in the organic electroluminescent device.
Preferably, the material of the hole injection layer includes, but is not limited to, one or more of the following compounds:
preferably, the hole injection layer has a thickness of 30-50nm, preferably 40 nm.
Preferably, the thickness of the hole transport layer is 5-15nm, preferably 10 nm.
Preferably, the thickness of the organic light emitting layer is 10 to 100nm, preferably 40 nm.
Preferably, the thickness of the electron transport layer is 10-30nm, preferably 50 nm.
Preferably, the thickness of the cathode layer is 90-110nm, preferably 100 nm.
The invention also provides application of the indenoimidazole compound, including application in preparing organic electroluminescent materials and application in preparing organic electroluminescent devices.
The invention has the following beneficial effects:
the compound shown in the formula I has the carrier transmission capacity, and an organic electroluminescent device prepared by using the compound can reduce the starting voltage and improve the luminous efficiency and brightness. The series of compounds have good film-forming properties, and the compounds have the characteristics that the synthesis and purification methods are simple and suitable for large-scale production, and the like, and are ideal choices as electronic transmission materials of organic electroluminescent devices. The application of the compound as a light-emitting material or as a host material or a hole transport material or an electron transport material or a hole blocking material in a light-emitting layer is also within the scope of protection.
Drawings
The following describes embodiments of the present invention in further detail with reference to the accompanying drawings.
FIG. 1 shows a flow diagram of a process for the preparation of a compound of formula I according to the invention;
FIG. 2 shows a schematic structural diagram of an OLED device in example 6 of the present invention, wherein 1-substrate, 2-anode layer, 3-hole injection layer, 4-hole transport layer, 5 organic light emitting layer, 6-electron transport layer, 7-cathode layer;
FIG. 3 shows the compound of formula CJH-P16 in example 1 of the invention1H-NMR spectrum;
FIG. 4 shows the compound of formula CJH-P16 in example 1 of the invention13A C-NMR spectrum;
FIG. 5 shows the visible-ultraviolet absorption spectrum of compound formula CJH-P16 in example 1 of the invention;
FIG. 6 shows a fluorescence spectrum of the compound of formula CJH-P16 in example 1 of the invention;
FIG. 7 shows the compound of formula CJH-P23 in example 1 of the invention1H-NMR spectrum;
FIG. 8 shows a fluorescence spectrum of the compound of formula CJH-P23 in example 1 of the invention.
Detailed Description
In order to more clearly illustrate the invention, the invention is further described below with reference to preferred embodiments and the accompanying drawings. Similar parts in the figures are denoted by the same reference numerals. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
In the description of the present invention, "a plurality" means two or more unless otherwise specified; the terms "upper", "lower", and the like, indicate orientations or positional relationships based on the orientations or positional relationships shown in the drawings, and are only for convenience in describing the present invention and simplifying the description, but do not indicate or imply that the referred devices or elements must have a specific orientation, be constructed and operated in a specific orientation, and thus, should not be construed as limiting the present invention.
In the present invention, the preparation methods are all conventional methods unless otherwise specified. The starting materials used are, unless otherwise specified, available from published commercial sources, and the percentages are, unless otherwise specified, percentages by mass.
Example 1
The structural formula of the compound CJH-P16 is shown as follows:
the preparation route is as follows:
the first step is as follows: preparation of intermediate int
15g (54.5mmol) of 4-bromo-N-phenylbenzamidine Int-1, 9.4g (45.5mmol) of chalcone, 1.5g of anhydrous ferric chloride, 1.2g of iodine, 80ml of dichlorobenzene, oxygen introduction, heating to 110 ℃, stirring for reaction for 8 hours, cooling to room temperature, pouring the reaction solution into 800ml of petroleum ether, filtering, washing a filter cake with petroleum ether, and recrystallizing with ethanol to obtain 16g of yellow solid Int-2 with a yield of 75%.
The second step is that: preparation of intermediate int. -3
15g (31.3mmol) of intermediate int-2 is dissolved in 150ml of anhydrous tetrahydrofuran, 46.9mmol of phenylmagnesium bromide solution in tetrahydrofuran is added dropwise under the protection of nitrogen, the mixture is stirred and reacted for 8 hours at room temperature, the temperature is increased and the reflux reaction is carried out for 1 hour, the mixture is cooled to room temperature, 50ml of saturated aqueous ammonium chloride solution is added dropwise, the mixture is extracted by ethyl acetate, the organic phase is dried and filtered, and the filtrate is concentrated under reduced pressure to dryness, so that 16.7g of black oily substance int-3 is obtained, and the yield is 96%.
The third step: preparation of intermediate int. -4
Dissolving the intermediate int. -3 prepared in the previous step in 100mL of acetic acid and 5mL of concentrated hydrochloric acid, heating, refluxing and stirring for reaction for 12 hours, cooling to room temperature, concentrating under reduced pressure to dryness, separating and purifying by using a silica gel column, and recrystallizing by using ethanol to obtain 11g of white solid int. -4 with the yield of 68%.
The fourth step: preparation of compound CJH-P16
5g (9.2mmol) of intermediate int. -4, 3.2g (11.1mmol) of 9-phenyl-9H-carbazole-3-boronic acid, 2g (18.5mmol) of sodium carbonate and 5mg of Pd (PPh)3)4Adding 40mL of toluene, 10mL of ethanol and 5mL of water into the catalyst, heating, refluxing, stirring and reacting for 12 hours, cooling to room temperature, extracting with ethyl acetate, drying the organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, separating and purifying by using a silica gel column, performing heat-returning reflux by using ethanol, and filtering while hot to obtain 5.5g of yellow solid CJH-P16 with the yield of 84%. HRMS: C52H35N3, Standard molecular weight 701.283, test results 702.289, Nuclear magnetism1HNMR and13the CNMR is shown in FIG. 3 and FIG. 4, and the visible-ultraviolet absorption spectrum and the fluorescence spectrum are shown in FIG. 5 and FIG. 6.
Referring to the synthesis method of example 1, the following compounds were prepared, namely, the method steps were the same as example 1, except that different compounds were used according to the desired products instead of 9-phenyl-9H-carbazole-3-boronic acid in the fourth step of example 1 according to actual needs, and the mass amounts of the compounds were changed according to molar amounts, as shown in table 1:
table 1 mass spectrometry results and carrier mobilities of different compounds
Example 2
The structural formula of the compound CJH-P48 is shown as follows:
the preparation route is as follows:
the first step is as follows: preparation of intermediate int. -5
Synthetic procedure the phenylmagnesium bromide from the second step of example 1 was replaced with methylmagnesium iodide with reference to the second step of example 1 to give the intermediate int. -5 as a black oil in 88% yield.
The second step is that: preparation of intermediate int. -6
Synthetic procedure the intermediate int. -3 of the third step of example 1 was replaced with the intermediate int. -5 with reference to the third step of example 1, giving the intermediate int. -6 as a black oil in 58% yield.
The third step: preparation of product CJH-P48
5g (10.4mmol) of intermediate int. -6, 4g (12.5mmol) of (4- (1-phenyl-1H-benzo [ d ])]Mixing imidazole-2-phenyl) boric acid and 2.2g (20.8mmol) of sodium carbonate, adding 54mg of Pd (PPh3)4 catalyst and 40mL of toluene, adding 20mL of ethanol and 20mL of water, heating, refluxing and stirring for reaction for 12 hours under the protection of nitrogen, cooling to room temperature, extracting with ethyl acetate, drying an organic phase with anhydrous sodium sulfate, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain 6.2g of yellow solid CJH-P48, yield 89%. HRMS: C48H34N4, Standard molecular weight 666.278, test results 667.283,1HNMR (δ, CDCl 3): 8.33 to 8.36(1H, m); 7.74-7.84 (5H, m); 7.19-7.64 (25H, m); 2.26(3H, s). Carrier mobility: 6.5X 10-5cm2/VS。
Referring to the synthesis method of example 2, the following compounds were prepared, namely, the method steps were the same as example 2, except that different compounds were used according to actual needs in place of (4- (1-phenyl-1H-benzo [ d ] imidazole-2-phenyl) boronic acid in the third step of example 2 according to the desired products, and the mass amounts of the compounds were changed according to molar amounts, as shown in table 2:
table 2 mass spectrometry results and carrier mobilities for different compounds
| Serial number | Compound numbering | Mass spectrometry test results | Carrier mobility (cm)2/VS) |
| 54 | CJH-P50 | 729.302 | 4.4×10-5 |
| 55 | CJH-P52 | 675.249 | 5.4×10-5 |
| 56 | CJH-P54 | 696.273 | 4.7×10-5 |
| 57 | CJH-P56 | 694.290 | 7.2×10-5 |
Example 3
The structural formula of the compound CJH-P60 is shown as follows:
the preparation route is as follows:
the first step is as follows: preparation of intermediate int. -8
Synthetic procedure referring to the first step of example 1, the chalcone of the first step of example 1 was replaced with intermediate int. -7 to give intermediate int. -8 as a yellow solid in 56% yield.
The second step is that: preparation of intermediate int. -9
Synthetic procedure the second step of example 1 was referenced, replacing the phenylmagnesium bromide of the second step of example 1 with methylmagnesium iodide and the intermediate int. -2 of the second step of example 1 with intermediate int. -8 to give intermediate int. -9 as a black oil in 87% yield.
The third step: preparation of intermediate int. -10
Dissolving the intermediate int. -9 prepared in the previous step in acetic acid, slowly dropwise adding into concentrated sulfuric acid cooled to 0 ℃, stirring for reaction for 1 hour, heating to room temperature, stirring for reaction for 12 hours, pouring the reaction solution into ice water, filtering, washing a filter cake with water, separating and purifying by using a silica gel column, and recrystallizing by using ethanol to obtain white solid int. -10 with the yield of 86%.
The fourth step: preparation of compound CJH-P60
5g (12mmol) of intermediate int. -10, 5.3g (14.5mmol) of int. -11, i.e. (4- (9-phenyl-9H-pyrido [3,4-b ])]Indol-1-yl) phenyl) boronic acid and 2.54g (24mmol) of sodium carbonate are mixed, 54mg of Pd (PPh3)4 catalyst and 40mL of toluene are added, 20mL of ethanol and 20mL of water are added, the mixture is heated under reflux and stirred for reaction for 12 hours under the protection of nitrogen, the mixture is cooled to room temperature and extracted by ethyl acetate, an organic phase is dried by anhydrous sodium sulfate and filtered, and a filtrate is concentrated under reduced pressure and dried and is separated and purified by a silica gel column, so that 6.2g of yellow solid CJH-P60 is obtained, and the yield is 79%. HRMS: c47H34N4Standard molecular weight 654.278, test result 655.282,1HNMR (δ, CDCl 3): 8.53 to 8.63(2H, m); 8.23-8.05 (5H, m); 7.28-7.82 (21H, m); 1.42(6H, s). Carrier mobility: 4.8X 10-5cm2/VS。
Referring to the synthesis procedure of example 3, the following compounds were prepared, namely the procedure was the same as in example 3 except that different compounds were used according to actual needs instead of (4- (9-phenyl-9H-pyrido [3,4-b ] indol-1-yl) phenyl) boronic acid in the fourth step of example 3 according to the desired products, and the mass amounts of the compounds were changed according to molar amounts, and the results are shown in table 3:
table 3 mass spectrometry results and carrier mobilities of different compounds
Example 4
The structural formula of the compound CJH-P67 is shown as follows:
the preparation route is as follows:
5g (8.1mmol) of intermediate int. -12, 1.35g (8mmol) of int. -13, namely diphenylamine, and 1.2g (12mmol) of sodium tert-butoxide are mixed, 73mg (0.08mmol) of Pd2(dba)3 catalyst and 80mL of toluene are added, 0.2mL of 10% tri-tert-butylphosphine toluene solution is added under the protection of nitrogen, the mixture is heated to 90 ℃ and stirred for reaction for 16 hours, the mixture is cooled to room temperature, 80mL of water is added, an organic phase is separated, an aqueous phase is extracted by ethyl acetate, the organic phase is dried by anhydrous sodium sulfate and filtered, filtrate is concentrated under reduced pressure to dryness, and is separated and purified by a silica gel column to obtain 3.7g of yellow solid with the yield of 66%. HRMS: c52H37N3Standard molecular weight 703.299, test result 704.302,1HNMR (δ, CDCl 3): 7.72 to 7.74(2H, m); 7.44-7.54 (8H, m); 7.27 to 7.39(13H, m); 7.11-7.20 (12H, m); 7.02 to 7.06(2H, m). Carrier mobility: 8.4X 10-5cm2/VS。
Example 5
The structural formula of the compound CJH-P70 is shown as follows:
the preparation method specifically comprises the following steps:
5g (8.1mmol) of intermediate int. -12, 2.9g (8mmol) of intermediate int. -13 and 1.2g (12mmol) of sodium tert-butoxide are mixed, 73mg (0.08mmol) of Pd2(dba)3 catalyst and 80mL of toluene are added, 0.2mL of 10% tri-tert-butylphosphine toluene solution is added under nitrogen protection, the mixture is heated to 90 ℃ and stirred for reaction for 16 hours, the mixture is cooled to room temperature, 80mL of water is added, the organic phase is separated, the aqueous phase is extracted with ethyl acetate, the organic phase is dried with anhydrous sodium sulfate and filtered, the filtrate is concentrated under reduced pressure and dried, and is separated and purified by a silica gel column, so that 6.2g of yellow solid is obtained with the yield of 86%. HRMS: c67H49N3Standard molecular weight 895.393, test result 896.398,1HNMR (δ, CDCl 3): 7.63 to 7.69(3H, m); 7.57-7.60 (3H, m); 7.47-7.51 (4H, m); 7.24-7.44 (14H, m); 7.12-7.20 (19H, m); 1.41(6H, s). Carrier mobility: 6.4X 10-5cm2/VS。
Referring to the synthesis procedure of example 5, the following compounds were prepared, i.e., the procedure was the same as example 5, except that int. -13 in example 5 was replaced with different compounds according to actual needs depending on the desired products, and the mass amounts of the compounds were changed according to molar amounts, and the results are shown in table 4:
table 4 mass spectrometry results and carrier mobilities for different compounds
| Serial number | Compound numbering | Mass spectrometry test results | Carrier mobility (cm)2/VS) |
| 68 | CJH-P68 | 804.332 | 6.5×10-5 |
| 69 | CJH-P69 | 856.363 | 5.3×10-5 |
| 70 | CJH-P71 | 936.425 | 5.1×10-5 |
| 71 | CJH-P72 | 869.360 | 5.4×10-5 |
| 72 | CJH-P73 | 919.375 | 4.7×10-5 |
| 73 | CJH-P74 | 871.374 | 4.8×10-5 |
| 74 | CJH-P75 | 921.389 | 3.7×10-5 |
| 75 | CJH-P76 | 942.378 | 5.5×10-5 |
| 76 | CJH-P77 | 744.342 | 4.0×10-5 |
| 77 | CJH-P81 | 793.326 | 7.8×10-5 |
Example 6
An organic electroluminescent device, which is a bottom emission light device, and has a structure shown in fig. 2, includes a substrate 1, an anode layer 2 disposed on the substrate 1, a hole injection layer 3 disposed on the anode layer 2, a hole transport layer 4 disposed on the hole injection layer 3, an organic light emitting layer 5 disposed on the hole transport layer 4, an electron transport layer 6 disposed on the organic light emitting layer 5, and a cathode layer 7 disposed on the electron transport layer 6, and is prepared by the following steps:
1) carrying out ultrasonic treatment on the glass substrate coated with the ITO conductive layer in a cleaning agent for 30 minutes, washing the glass substrate in deionized water, carrying out ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baking the glass substrate in a clean environment until the glass substrate is completely dried, irradiating the glass substrate for 10 minutes by using an ultraviolet light cleaning machine, and bombarding the surface by using low-energy cation beams;
2) placing the processed ITO glass substrate in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, evaporating a compound 2-TNATA serving as a hole injection layer on the anode layer film at the evaporation rate of 0.1nm/s and at the evaporation film thickness of 40 nm;
3) continuously evaporating NPB on the hole injection layer to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
4) continuously evaporating and plating ADN as a main material and DPVBi as a doping material on the hole transport layer, wherein the mass ratio of ADN to DPVBi is 98:2, the film thickness of the organic light-emitting layer obtained by evaporation is 40nm as an organic light-emitting layer of the device, and the evaporation rate is 0.1 nm/s;
5) continuously evaporating a layer of the compound (formula I) as a main body material and LiQ as a doping material on the organic light-emitting layer, wherein the mass ratio of the compound (formula I) to the LiQ is 90:10, the compound (formula I) is used as an electron transport layer of a device, the evaporation rate is 0.1nm/s, and the evaporation film thickness is 50 nm;
6) and sequentially evaporating a magnesium/silver alloy layer on the electron transport layer to serve as a cathode layer of the device, wherein the evaporation rate of the magnesium/silver alloy layer is 2.0-3.0 nm/s, the evaporation film thickness is 100nm, and the mass ratio of magnesium to silver is 1: and 9, obtaining the OLED device provided by the invention.
Selecting the compound (formula I) in the step 5) as CJH-P15 according to the same procedure as above to obtain OLED-1 provided by the present invention;
selecting the compound (formula I) in the step 5) as CJH-P20 according to the same procedure as above to obtain OLED-2 provided by the present invention;
selecting the compound (formula I) in the step 5) as CJH-P29 according to the same procedure as above to obtain OLED-3 provided by the present invention;
selecting the compound (formula I) in the step 5) as CJH-P48 according to the same procedure as above to obtain OLED-4 provided by the present invention;
selecting the compound (formula I) in the step 5) as CJH-P60 according to the same procedure as above to obtain OLED-5 provided by the present invention;
replacing the compound (formula I) in step 5) with Alq3 according to the same procedure as above to obtain a comparative device OLED-6;
the results of the performance tests of the obtained devices OLED-1 to OLED-6 are shown in Table 5.
TABLE 5 measurement results of OLED-1 to OLED-6
From the above, the device prepared by the organic material of the present invention has low lighting voltage, under the same current density, the brightness and efficiency are obviously higher than those of Alq3 as an electron transport layer, and the half-life period of the device is greatly prolonged.
It should be understood that the above-mentioned embodiments of the present invention are only examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention, and it will be obvious to those skilled in the art that other variations or modifications may be made on the basis of the above description, and all embodiments may not be exhaustive, and all obvious variations or modifications may be included within the scope of the present invention.
Claims (15)
1. An indenoimidazole compound is characterized in that the structural formula is shown as a formula I:
wherein R is1、R2、R3、R4Each independently represents hydrogen, deuterium hydrogen, a compound containing C1～C8Linear or branched alkyl of (C)1～C8Linear or branched alkoxy of (C)6-C60Aryl radical, C6-C60Aromatic vinyl radical, C6-C60Condensed ring aromatic group, C6-C60Arylamine group, C6-C60Condensed ring aromatic group containing nitrogen atom, C6-C60Condensed ring aromatic groups containing sulfur or oxygen atoms, C6-C60A condensed ring aromatic group containing phosphorus or silicon or boron atom, and C2-C60One of heterocyclic aryl;
Ar1、Ar2each independently represents phenyl, naphthyl, fluorenyl, spirofluorenyl, anthracenyl and C2-C60One of heterocyclic aryl;
n represents an integer of 1 to 5.
2. The indenoimidazole compound of claim 1, wherein C is2-C60The heterocyclic aryl is selected from pyridyl, pyrimidyl, quinolyl and carbazolyl.
3. The indenoimidazole compound of claim 1, wherein R is1、R2、R3、R4、Ar1、Ar2In the group, the C2-C60Each of the heterocyclic aryl groups of (a) is independently selected from one or more of the following structures II-1 to II-15:
wherein Z is1、Z2、Z3Each independently represents hydrogen, deuterium hydrogen, halogen atom, nitrile group, C1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, C1-C60Alkoxy radical, C3-C60Cycloalkyl radical, C3-C60Cycloalkenyl radical, C6-C60Aryl radicals containing at least one-F, -CN or C1-C10C of alkyl6-C60Aryl radical, C6-C60Aryloxy radical, C6-C60An arylsulfonyl group, and C2-C60One of heterocyclic aryl;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
T1represents oxygen or sulfur;
4. The indenoimidazole compound of claim 3, wherein the indenoimidazole compound having the structural formula I has the structural formula specifically represented by formula CJH-P01 to formula CJH-P84:
5. a material, characterized in that the raw material of the material comprises one or more of the indenoimidazole compounds as claimed in any one of claims 1 to 4; the material is an organic electroluminescent material.
6. An organic electroluminescent device, characterized in that the material of the organic electroluminescent device comprises one or more of the indenoimidazole compounds as claimed in any one of claims 1 to 4.
7. The organic electroluminescent device according to claim 6, wherein the material of at least one of the hole transport layer, the organic light-emitting layer and the electron transport layer in the organic electroluminescent device comprises one or more of the indenoimidazole compounds.
8. An organic electroluminescent device according to claim 6 or 7, wherein the hole injection layer has a thickness of 30 to 50 nm; the thickness of the hole transport layer is 5-15 nm; the thickness of the organic light-emitting layer is 10-100 nm; the thickness of the electron transmission layer is 10-30 nm; the thickness of the cathode layer is 90-110 nm.
9. An organic electroluminescent device according to claim 6 or 7, wherein the hole injection layer has a thickness of 40 nm.
10. An organic electroluminescent device according to claim 6 or 7, wherein the hole transport layer is 10nm thick.
11. An organic electroluminescent device according to claim 6 or 7, wherein the organic light-emitting layer is 40nm thick.
12. An organic electroluminescent device according to claim 6 or 7, wherein the electron transport layer is 50nm thick.
13. An organic electroluminescent device according to claim 6 or 7, wherein the cathode layer has a thickness of 100 nm.
14. The use of the indenoimidazole compound as claimed in any one of claims 1 to 4 in the preparation of organic electroluminescent materials.
15. Use of the indenoimidazole compound as claimed in any one of claims 1 to 4 in the preparation of an organic electroluminescent device.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710851663.8A CN107573328B (en) | 2017-09-20 | 2017-09-20 | Indenoimidazole compound, material containing same and organic electroluminescent device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710851663.8A CN107573328B (en) | 2017-09-20 | 2017-09-20 | Indenoimidazole compound, material containing same and organic electroluminescent device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107573328A CN107573328A (en) | 2018-01-12 |
| CN107573328B true CN107573328B (en) | 2020-06-02 |
Family
ID=61032928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710851663.8A Active CN107573328B (en) | 2017-09-20 | 2017-09-20 | Indenoimidazole compound, material containing same and organic electroluminescent device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107573328B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201804511D0 (en) * | 2018-03-21 | 2018-05-02 | Univ Birmingham | Luminescent compounds |
| CN110950864A (en) * | 2019-12-16 | 2020-04-03 | 株洲千金药业股份有限公司 | Preparation method of zolpidem impurity |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104039778A (en) * | 2011-07-21 | 2014-09-10 | 罗门哈斯电子材料韩国有限公司 | 9H-carbazole compounds and electroluminescent devices involving them |
| CN104030988A (en) * | 2014-06-25 | 2014-09-10 | 上海道亦化工科技有限公司 | Benzimidazole-based electron transport compound |
-
2017
- 2017-09-20 CN CN201710851663.8A patent/CN107573328B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104039778A (en) * | 2011-07-21 | 2014-09-10 | 罗门哈斯电子材料韩国有限公司 | 9H-carbazole compounds and electroluminescent devices involving them |
| CN104030988A (en) * | 2014-06-25 | 2014-09-10 | 上海道亦化工科技有限公司 | Benzimidazole-based electron transport compound |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107573328A (en) | 2018-01-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP3750875A2 (en) | Nitrogen-containing compound, organic electroluminescent device and photoelectric conversion device | |
| CN107021926B (en) | Compound containing azaspirofluorene and nitrogen-containing six-membered heterocycle and application of compound in OLED | |
| KR100935356B1 (en) | Green electroluminescent compounds and organic electroluminescent device using the same | |
| CN108586188B (en) | chrysene derivative, material containing chrysene derivative and organic electroluminescent device | |
| CN107021956B (en) | Benzoxazole derivative and application thereof | |
| TWI593684B (en) | The organic electroluminescent material and organic electroluminescence device | |
| CN111574544A (en) | Organic compound containing boron and application thereof in organic electroluminescent device | |
| CN107556310B (en) | Imdazole derivatives, material and organic electroluminescence device comprising the imdazole derivatives | |
| CN111574543A (en) | Organic compound containing boron and application thereof in organic electroluminescent device | |
| CN110229071A (en) | Fluorene derivative organic electroluminescence device | |
| CN104497013B (en) | Azepine carbazoles OLED material and preparation method and application | |
| CN109942637B (en) | Metal complex and organic electroluminescent device | |
| CN113402507B (en) | Triphenylene derivative, light-emitting device material, and light-emitting device | |
| CN109336782B (en) | Fluorene derivative and organic electroluminescent device thereof | |
| CN110294663B (en) | Compound with anthracene as core and application thereof in organic electroluminescent device | |
| CN110818675A (en) | Organic compound and application thereof | |
| CN108623430A (en) | Dinaphthalene derivatives, material and organic electroluminescence device comprising the dinaphthalene derivatives | |
| CN112625042A (en) | Organic electroluminescent material and application thereof | |
| CN111072677A (en) | Organic compound and application thereof | |
| CN110577488A (en) | Compound with carbazole as core and application thereof in organic electroluminescent device | |
| CN110294735B (en) | Compound with anthracene and phenanthrene as core and application of compound in organic electroluminescent device | |
| CN107573328B (en) | Indenoimidazole compound, material containing same and organic electroluminescent device | |
| CN110526905B (en) | Ketone-containing compound and application thereof in organic electroluminescent device | |
| CN110526857A (en) | A kind of luminous organic material and its application for preparing organic electroluminescence device | |
| CN110551132A (en) | ketone-containing compound and application thereof in organic electroluminescent device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |