CN115141186A - Compound, organic electroluminescent device and display device - Google Patents

Compound, organic electroluminescent device and display device Download PDF

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CN115141186A
CN115141186A CN202110350653.2A CN202110350653A CN115141186A CN 115141186 A CN115141186 A CN 115141186A CN 202110350653 A CN202110350653 A CN 202110350653A CN 115141186 A CN115141186 A CN 115141186A
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compound
carbon atoms
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organic electroluminescent
electroluminescent device
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CN115141186B (en
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陆金波
丁言苏
王占奇
郭林林
李志强
刘小龙
董青山
徐俏俏
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Beijing Xinyihua Material Technology Co ltd
Fuyang Sineva Material Technology Co Ltd
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Fuyang Sineva Material Technology Co Ltd
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Abstract

The application relates to the field of electroluminescence, and discloses a compound, an organic electroluminescent device and a display device. The structural formula of the compound is shown as the formula (I):

Description

Compound, organic electroluminescent device and display device
Technical Field
The application relates to the field of electroluminescence, in particular to a compound, an organic electroluminescent device and a display device.
Background
Currently, organic electroluminescent (OLED) display technology has been applied in the fields of smart phones, tablet computers, and the like, and further will be expanded to large-size application fields such as televisions. In the development process of the last 30 years, various OLED materials with excellent performance are developed, and the commercialization process of the OLED is accelerated by different designs of the device structure and optimization of the device life, efficiency and other properties, so that the OLED is widely applied in the fields of display and illumination.
However, since there is a great gap between the external quantum efficiency and the internal quantum efficiency of the OLED, the development of the OLED is greatly restricted, and one of the most important factors is that the efficiency of the device still does not reach a desired level. This is because most of light is confined inside the light emitting device due to mode loss of the substrate, loss of surface plasmon, and waveguide effect, thereby reducing the light emitting efficiency of the device. Improving the light emitting efficiency of the device, and using light extraction materials is one of the effective methods. The light extraction Layer (CPL) can adjust the light extraction direction and the light extraction efficiency by reducing the surface plasma effect of the metal electrode, and can effectively improve the light extraction efficiency of the device, thereby improving the luminous efficiency of the device. At present, the light extraction material is of a single type and has an unsatisfactory effect, and developing a more effective light extraction material is one of the more serious challenges facing OLED workers.
In addition, the selection of the materials of the light-emitting layer and other organic functional layers also has a great influence on the current efficiency and driving voltage of the device, and functional layer materials with higher performance are still being explored.
Therefore, in order to meet the higher requirements of people for OLED devices, the development of more various and higher-performance OLED materials is urgently needed in the art.
Disclosure of Invention
The application discloses a carbazole compound, and an organic electroluminescent device and a display device comprising the carbazole compound.
In order to achieve the purpose, the application provides the following technical scheme:
a compound has a structural formula shown as a formula (I),
Figure BDA0003002291180000021
wherein m and n are selected from 0 or 1;
Ar 1 each A is independently selected from substituted or unsubstituted arylene groups containing 6 to 24 carbon atoms;
Ar 2 selected from the group consisting of formula (II) wherein the carbon atom Sp2 hybridizes with and can participate in the attachment is attached to A or N, X is selected from O, S;
Ar 3 selected from formula (II) or a substituted or unsubstituted aryl group containing 6 to 24 carbon atoms, wherein any one of Sp2 is hybridized and the carbon atom which can participate in the attachment is attached to N;
R 01 selected from substituted or unsubstituted alkyl groups containing 1 to 6 carbon atoms or substituted or unsubstituted aryl groups containing 6 to 13 carbon atoms;
R 011 ～R 017 each independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group containing from 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group containing from 6 to 13 carbon atoms;
Ar 1 、Ar 2 、Ar 3 and the hydrogen in A can be independently replaced by R, and R is selected from deuterium, F, CN, alkyl containing 1-20 carbon atoms, alkoxy containing 1-20 carbon atoms and alkyl containing 6-40 carbon atomsAn aromatic group;
one or more hydrogen atoms on the aromatic ring in formula (I) may be replaced by deuterium, fluorine or cyano.
Further, ar 1 、Ar 3 And A is selected from one or more of benzene, biphenyl, naphthalene, phenanthrene, anthracene, fluorene, triphenylene, fluoranthene, pyrene, perylene, spirofluorene, indenofluorene or hydrogenated benzanthracene.
Further, the structure of the compound is:
Figure BDA0003002291180000022
further, the compound comprises one of formula P-1 to formula P-186:
Figure BDA0003002291180000031
Figure BDA0003002291180000041
Figure BDA0003002291180000051
Figure BDA0003002291180000061
Figure BDA0003002291180000071
Figure BDA0003002291180000081
Figure BDA0003002291180000091
Figure BDA0003002291180000101
the compounds represented by the formulae P-94 to P-186 are compounds obtained by replacing O in the formulae P-1 to P-93 with S, respectively.
An organic electroluminescent device comprising a compound as described herein.
Further, the material of the hole transport layer or the hole injection layer of the organic electroluminescent device is the compound of the application.
Further, the host material of the light-emitting layer of the organic electroluminescent device is the compound.
A display device includes the organic electroluminescent device provided by the application.
By adopting the technical scheme of the application, the beneficial effects are as follows:
the compound shown in the formula (I) is a novel compound, and can be used for organic electroluminescent devices and used as HTL, EBL and Host materials. In addition, the OLED device prepared by using the compound material shown in the formula (I) has low driving voltage and high luminous efficiency.
Detailed Description
The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the embodiments of the present application, and it is obvious that the described embodiments are only a part of the embodiments of the present application, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present application.
It should be noted that: in the present application, all embodiments and preferred methods mentioned herein can be combined with each other to form new solutions, if not specifically stated. In the present application, all the technical features mentioned herein as well as preferred features may be combined with each other to form new technical solutions, if not specifically stated. In the present application, percentages (%) or parts refer to percent by weight or parts by weight relative to the composition, unless otherwise specified. In the present application, the components referred to or the preferred components thereof may be combined with each other to form new embodiments, if not specifically stated. In this application, unless otherwise stated, the numerical range "a-b" represents a shorthand representation of any combination of real numbers between a and b, where a and b are both real numbers. For example, a numerical range of "6 to 22" indicates that all real numbers between "6 to 22" have been listed herein, and "6 to 22" is only an abbreviated representation of the combination of these numbers. The "ranges" disclosed herein may be in the form of lower limits and upper limits, and may be one or more lower limits and one or more upper limits, respectively. In the present application, unless otherwise indicated, the individual reactions or process steps may or may not be performed in sequence. Preferably, the reaction processes herein are carried out sequentially.
Unless otherwise defined, technical and scientific terms used herein have the same meaning as is familiar to those skilled in the art. In addition, any methods or materials similar or equivalent to those described herein can also be used in the present application.
Synthesis example 1 Synthesis of P-1
The synthetic route of compound P-1 is as follows:
Figure BDA0003002291180000111
a 500 ml three-necked flask, protected by nitrogen, charged with 200 ml of dried toluene, 4.87 g (0.01 mol) of the compound represented by M-1, 3.55 g of 3-bromobenzo [ kl ] xanthene, 0.0575 g (0.0001 mol) of Pd (dba) 2 (palladium bis-dibenzylideneacetone), 0.4 g (0.0002 mol) of a toluene solution containing 10% tri-tert-butylphosphine, 1.44 g (0.015 mol) of sodium tert-butoxide, heated to reflux for 6 hours, cooled, added with water for liquid separation, washed with water of the organic layer to neutrality, dried with magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, separated by silica gel column chromatography, petroleum ether: ethyl acetate =8:2 (volume ratio) to obtain 5.16 g of the compound represented by P-1.
Performing mass spectrum detection on the compound shown as the P-1, and determining that the molecular m/z is as follows: 702.
the compound shown as P-1 is subjected to nuclear magnetic detection, and the data are analyzed as follows:
1H-NMR (Bruker, switzerland, avance II 400MHz NMR spectrometer, CDCl 3). Delta.8.22-8.16 (m, 2H), delta.8.06 (m, 1H), delta.7.96 (m, 1H), delta.7.86 (m, 1H), delta.7.74 (m, 2H), delta.7.72 (d, 1H), delta.7.66-7.30 (m, 20H), delta.7.28-7.13 (m, 5H), delta.6.41 (m, 1H).
Synthesis example 2 Synthesis of P-25
Figure BDA0003002291180000121
Synthesis method the synthesis of P-1 in example 1 was followed except that the compound represented by M-1 was changed to the compound represented by M-2 to give the compound P-25.
Performing mass spectrum detection on the compound shown as the P-25, and determining that the m/z of the molecule is as follows: 626.
synthesis example 3 Synthesis of P-46
Figure BDA0003002291180000122
Synthesis method the synthesis of P-1 in example 1 was followed except that the compound represented by M-1 was changed to the compound represented by M-3 to give the compound represented by P-46.
Performing mass spectrum detection on the compound shown as the P-46, and determining that the m/z of the molecule is as follows: 644.
synthesis example 4 Synthesis of P-49
Figure BDA0003002291180000131
Synthesis method with reference to the synthesis of P-1 in example 1, except that the compound represented by M-1 was changed to the compound represented by M-4, and 3-bromobenzo [ kl ] xanthene was 2.2 times (mass ratio) the compound represented by M-4, the reaction time was 16 hours, and the compound represented by P-49 was obtained.
Performing mass spectrum detection on the compound shown as the P-49, and determining that the molecular m/z is as follows: 766.
synthesis example 5 Synthesis of P-70
(1) Synthesis of intermediate M-703
Figure BDA0003002291180000132
Adding 50 ml of DMF (dimethyl formamide), 2.97 g (0.01 mol) of 8-bromobenzo [ kl ] xanthene into a 250 ml three-neck flask, controlling the temperature to be 20-25 ℃, adding 2.25 g (0.01 mol) of N-iodosuccinimide (NIS) in batches while stirring, controlling the temperature to be 20-25 ℃ for reaction for 2 hours, heating to be 40-45 ℃ for reaction for 1 hour, heating to be 60 ℃ for reaction for 1 hour, cooling, adding water and dichloromethane for liquid separation, washing an organic layer with water, separating by silica gel column chromatography, eluting with petroleum ether to obtain 1.8 g of a compound shown in M-703.
Mass spectrometric detection of the compound of formula M-3, with the largest two peaks at 422, 424, determined the product molecular formula: c 16 H 8 BrIO。
The compound shown as the formula M-703 is subjected to nuclear magnetic detection, and the data are analyzed as follows: 1H-NMR (Bruker, switzerland, avance II 400MHz NMR spectrometer, CDCl 3), delta 8.51 (m, 1H), delta 7.88 (m, 1H), delta 7.82 (m, 2H), delta 7.68 (m, 1H), delta 7.62 (d, 1H), delta 7.44 (d, 1H), delta 7.10 (m, 1H).
(2) Synthesis of intermediate M-704
Figure BDA0003002291180000141
A 250 ml three-neck flask is filled with toluene, ethanol and water in an amount of 60 ml and 20 ml under the protection of nitrogen, then 4.23 g (0.01 mol) of the compound shown in M-703, 1.22 g (0.01 mol) of phenylboronic acid, 2.12 g (0.02 mol) of sodium carbonate and 0.115 g (0.0001 mol) of palladium tetratriphenylphosphine are added, the temperature is slowly raised to 60 ℃ for reaction for 8 hours, the temperature is reduced, water is added for liquid separation, an organic layer is washed with water, magnesium sulfate and a small amount of 200-300-mesh silica gel are added for drying, after the magnesium sulfate and the silica gel are filtered and removed, the solvent is removed under reduced pressure, and the obtained solid is recrystallized for 2 times by using a mixed solvent of chlorobenzene and methanol to obtain 3.1 g of the compound shown in M-704.
The compound shown in M-704 is subjected to mass spectrum detection, the maximum two peaks are 372 and 374, and the molecular formula of the product is determined as follows: c 22 H 13 BrO。
(3) Synthesis of Compound P-70
Figure BDA0003002291180000142
Synthesis method referring to the synthesis of P-1 in example 1, except that 3-bromobenzo [ kl ] xanthene therein was replaced with a compound represented by M-704, a compound represented by P-70 was obtained.
Performing mass spectrum detection on the compound shown as the P-70, and determining that the m/z of the molecule is as follows: 778.
synthesis example 6 Synthesis of P-73
(1) Synthesis of intermediate M-708
Figure BDA0003002291180000143
A 250 ml three-neck bottle is filled with nitrogen, 50 ml of DMF,4.23 g (0.01 mol) of the compound shown as the formula M-703, 0.1 g of cuprous iodide and 1.16 g (0.02 mol) of KF are added, the mixture is heated to reflux reaction for 24 hours, the temperature is reduced to room temperature, water and dichloromethane are added for separating liquid, an organic layer is washed to be neutral, magnesium sulfate is dried and filtered, the organic layer is concentrated to be dry, silica gel column chromatography separation is carried out, petroleum ether is eluted, and 1.6 g of the compound shown as M-708 is obtained.
Performing mass spectrum detection on the compound shown in M-708, wherein the maximum two peaks are 314 and 316, and the molecular formula of the product is determined as follows: c 16 H 8 BrFO。
(2) Synthesis of Compound P-73
Figure BDA0003002291180000151
Synthesis method referring to the synthesis of the compound P-1 in example 1, except that 3-bromobenzo [ kl ] xanthene therein was replaced by the compound shown as M-708, the compound P-73 was obtained.
Performing mass spectrum detection on the compound shown as P-73, and determining that the molecular m/z is as follows: 720.
synthesis example 7 Synthesis of P-74
(1) Synthesis of intermediate M-709
Figure BDA0003002291180000152
A 250 ml three-neck flask is added with nitrogen protection, 50 ml DMF,4.23 g (0.01 mol) of the compound shown as the formula M-703, 0.1 g of cuprous iodide and 1.79 g (0.02 mol) of CuCN are added, the mixture is heated to reflux reaction for 24 hours, the temperature is reduced to room temperature, water and dichloromethane are added for separating liquid, an organic layer is washed to be neutral, magnesium sulfate is dried and filtered, the organic layer is concentrated to be dry, silica gel column chromatography separation is carried out, petroleum ether is eluted, and 1.9 g of the compound shown as M-709 is obtained.
Performing mass spectrum detection on the compound shown in M-709, wherein the maximum two peaks are 321 and 323, and the molecular formula of the product is determined as follows: c 17 H 8 BrNO。
(2) Synthesis of Compound P-74
Figure BDA0003002291180000161
Synthesis method referring to the synthesis of the compound P-1 in example 1, except that 3-bromobenzo [ kl ] xanthene therein was replaced with the compound shown in M-709 to give the compound P-74.
Performing mass spectrum detection on the compound shown as the P-74, and determining that the molecular m/z is as follows: 727.
synthesis example 8 Synthesis of P-84
(1) Synthesis of intermediate M-7010
Figure BDA0003002291180000162
A 250 ml three-neck flask, under the protection of nitrogen, adding 30 ml of DMF,2.97 g (0.01 mol) of 8-bromobenzo [ kl ] xanthene, 0.5 g of cuprous iodide and 1.16 g (0.02 mol) of KF, heating to reflux for reaction for 24 hours, cooling to room temperature, adding water and dichloromethane for liquid separation, washing an organic layer to neutrality, drying with magnesium sulfate, filtering out the magnesium sulfate, concentrating the organic layer to dryness, separating by silica gel column chromatography, and eluting with petroleum ether to obtain 0.9 g of the compound represented by M-7010.
Performing mass spectrum detection on the compound shown in M-7010, and determining that the molecular M/z is as follows: 236.
(2) Synthesis of intermediate M-7011
Figure BDA0003002291180000163
Adding 80 ml of DMF (dimethyl formamide), 2.36 g (0.01 mol) of 8-fluorobenzo [ kl ] xanthene shown as M-7010 into a 250 ml three-necked bottle, controlling the temperature to be 20-25 ℃, adding 1.78 g (0.01 mol) of N-bromosuccinimide (NBS) in batches under stirring, controlling the temperature to be 20-25 ℃, reacting for 6 hours, adding water and dichloromethane for separating, washing an organic layer with water, separating by silica gel column chromatography, and eluting by petroleum ether to obtain 1.6 g of a compound shown as M-7011.
The compound shown in the formula M-7011 is subjected to mass spectrum detection, the maximum two peaks are 314 and 316, and the molecular formula of the product is determined as follows: c 16 H 8 BrFO。
The compound shown as the formula M-7011 is subjected to nuclear magnetic detection, and the data are analyzed as follows: 1H-NMR (Bruker, switzerland, avance II 400MHz NMR spectrometer, CDCl 3), delta 8.49 (m, 1H), delta 7.71 (m, 2H), delta 7.68 (m, 1H), delta 7.65 (m, 1H), delta 7.46 (d, 1H), delta 7.24 (m, 1H), delta 7.20 (m, 1H).
(3) Synthesis of Compound A-84
Figure BDA0003002291180000171
Synthesis method referring to the synthesis of the compound P-1 in example 1, except that 3-bromobenzo [ kl ] xanthene therein was changed to a compound represented by M-7011, compound P-84 was obtained.
Performing mass spectrum detection on the compound shown as the P-84, and determining that the m/z of the molecule is as follows: 720.
the synthesis of products not shown in the above synthesis examples can be achieved by conventional methods using methods known in the art.
Device embodiment:
the specific structures of several materials used in this application are as follows:
Figure BDA0003002291180000172
Figure BDA0003002291180000181
device example 1
The compound of the present application was selected as a hole transport material in an organic electroluminescent device in the examples, and D-1 was selected as a hole transport material in an organic electroluminescent device in the comparative examples.
The organic electroluminescent device has the following structure: ITO/HIL02 (100 nm)/hole transport material (40 nm)/EM 1 (30 nm)/TPBI (30 nm)/LiF (0.5 nm)/Al (150 nm).
The preparation process of the organic electroluminescent device is as follows:
carrying out ultrasonic treatment on the glass substrate coated with the ITO transparent conductive layer (serving as an anode) in a cleaning agent, then washing the glass substrate in deionized water, ultrasonically removing oil in a mixed solvent of acetone and ethanol, baking the glass substrate in a clean environment until the water is completely removed, cleaning the glass substrate by using ultraviolet light and ozone, and bombarding the surface by using low-energy cation beams to improve the surface property and improve the binding capacity with a hole injection layer;
placing the glass substrate in a vacuum chamber, and vacuumizing to 1 × 10 -5 ～9×10 -3 Pa, performing vacuum evaporation on the anode to obtain HIL02 as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 100nm;
respectively carrying out vacuum evaporation on the compound and D-1 on the hole injection layer to serve as hole transport layers, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 40nm;
vacuum evaporating and plating EM1 on the hole transport layer to serve as an organic light emitting layer of the device, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 30nm;
vacuum evaporating TPBI on the organic light-emitting layer to be used as an electron transport layer of the organic electroluminescent device; the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30nm;
and (3) evaporating 0.5nm LiF and 150nm Al on the electron transport layer in vacuum to be used as an electron injection layer and a cathode.
The luminance, driving voltage, and current efficiency of the prepared organic electroluminescent device were measured.
The organic electroluminescent device properties are shown in table 1 below. And testing by using an OLED-1000 multichannel accelerated aging life and light color performance analysis system produced in Hangzhou distance.
TABLE 1
Hole transport material Required luminance cd/m 2 Drive voltage V Current efficiency cd/A
D-1 1000 5.77 1.77
P-1 1000 5.56 1.87
P-25 1000 5.55 1.89
P-49 1000 5.49 1.97
P-70 1000 5.01 1.91
P-73 1000 5.12 1.98
P-74 1000 5.06 2.01
P-84 1000 5.03 2.08
P-75 1000 5.28 1.98
P-68 1000 4.89 2.11
P-169 1000 4.69 2.02
As can be seen from the data in Table 1, the organic electroluminescent device prepared using the compound of the present application has a reduced driving voltage and an increased efficiency as compared to the compound D-1. The current efficiency of the organic electroluminescent device prepared by the compound can reach more than 1.8cd/A, some can reach more than 1.9cd/A, and the driving voltage can be reduced to be less than 5.6V, and some can reach less than 5.2V; particularly, the driving voltage of the device corresponding to the compounds P-68 to P-169 can be reduced to be below 5.3V, the current efficiency can reach more than 1.9cd/A, and the improvement effect is more obvious.
Device example 2
In the examples, the compound of the present application was used as a red host material in an organic electroluminescent device, and in the comparative examples, D-1 was used as a red host material in an organic electroluminescent device.
The structure of the organic electroluminescent device is as follows: ITO/NPB (20 nm)/Red host material (35 nm): ir (piq) 3[10% ]/TPBI (10 nm)/Alq 3 (15 nm)/LiF (0.5 nm)/Al (150 nm). Wherein "Ir (piq) 3," 10% "" means the doping ratio of the red dye, i.e., the weight part ratio of the red host material to Ir (piq) 3 is 100.
The preparation process of the organic electroluminescent device is as follows: the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
the above-mentioned belt is putPlacing the glass substrate with anode in a vacuum chamber, and vacuumizing to 1 × 10 -5 ～9×10 -3 Pa, vacuum evaporating a hole transport layer NPB on the anode layer film, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 20nm;
vacuum evaporating a red light main material and a dye Ir (piq) 3 on the hole transport layer to be used as a light emitting layer of the organic electroluminescent device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 35nm;
sequentially vacuum evaporating an electron transport layer TPBI and an electron transport layer Alq3 on the light-emitting layer, wherein the evaporation rates are both 0.1nm/s, and the evaporation film thicknesses are respectively 10nm and 15nm;
and (3) evaporating LiF with the thickness of 0.5nm and Al with the thickness of 150nm on the electron transport layer in vacuum to be used as an electron injection layer and a cathode.
All organic electroluminescent devices are prepared by the method, the difference is only in the selection of red light main body materials, and the specific details are shown in the following table 2.
And (3) performance testing:
the brightness, the driving voltage and the current efficiency of the prepared organic electroluminescent device are measured by using a Hangzhou remote production OLED-1000 multichannel accelerated aging life and photochromic performance analysis system test, and the test results are shown in the following table.
TABLE 2
Red light host material Required luminance cd/m 2 Drive voltage V Current efficiency cd/A
D-1 1000 4.67 38.88
P-1 1000 4.60 39.21
P-25 1000 4.59 41.01
P-49 1000 4.63 42.21
P-70 1000 3.86 51.66
P-73 1000 3.88 53.77
P-74 1000 3.65 52.69
P-84 1000 3.72 55.11
P-75 1000 3.66 51.89
As can be seen from the above table, compared with the comparative compound, the compound provided by the present application as the red host material of the organic electroluminescent device can improve the luminous efficiency and reduce the driving voltage, especially the effect of P-70 to P-84 is more prominent.
As can be seen from the data in table 2, compared to compound D-1, the compound provided by the present application as a red host material of an organic electroluminescent device can improve the current efficiency of the device and reduce the driving voltage. Specifically, compared with a comparative example, the current efficiency of the organic electroluminescent device prepared by using the compound can reach more than 40cd/A, and the driving voltage can be reduced to be less than 4.6V; particularly, the driving voltage of the device corresponding to the compounds P-70-P-84 can be reduced to be below 3.9V, the current efficiency can be improved to be above 50cd/A, and the improvement effect is more obvious.
It will be apparent to those skilled in the art that various changes and modifications may be made in the embodiments of the present application without departing from the spirit and scope of the application. Thus, if such modifications and variations of the present application fall within the scope of the claims of the present application and their equivalents, the present application is intended to include such modifications and variations as well.

Claims (6)

1. A compound is characterized in that the structural formula of the compound is shown as a formula (I),
Figure FDA0003002291170000011
wherein m and n are selected from 0 or 1;
Ar 1 each A is independently selected from substituted or unsubstituted arylene groups containing 6 to 24 carbon atoms;
Ar 2 selected from formula (II) wherein any one of Sp2 hybridises and the carbon atom that can participate in the attachment is attached to a or N, X is selected from O, S;
Ar 3 selected from formula (II) or a substituted or unsubstituted aryl group containing 6 to 24 carbon atoms, wherein any one of Sp2 is hybridized and the carbon atom which can participate in the attachment is attached to N;
R 01 selected from substituted or unsubstituted alkyl groups containing 1 to 6 carbon atoms or substituted or unsubstituted aryl groups containing 6 to 13 carbon atoms;
R 011 ～R 017 each independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group containing from 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group containing from 6 to 13 carbon atoms;
Ar 1 、Ar 2 、Ar 3 the hydrogen in A can be independently replaced by R, and R is selected from deuterium, F, CN, alkyl containing 1-20 carbon atoms, alkoxy containing 1-20 carbon atoms and aryl containing 6-40 carbon atoms;
one or more hydrogen atoms on the aromatic ring in formula (I) may be replaced by deuterium, fluorine or cyano.
2. The compound of claim 1, wherein Ar is Ar 1 、Ar 3 And A is selected from one or more of benzene, biphenyl, naphthalene, phenanthrene, anthracene, fluorene, triphenylene, fluoranthene, pyrene, perylene, spirofluorene, indenofluorene or hydrogenated benzanthracene.
3. The compound of claim 1, wherein the compound has the structure:
Figure FDA0003002291170000012
4. the compound of claim 1, wherein the compound comprises one of formula P-1 to formula P-186:
Figure FDA0003002291170000021
Figure FDA0003002291170000031
Figure FDA0003002291170000041
Figure FDA0003002291170000051
Figure FDA0003002291170000061
Figure FDA0003002291170000071
Figure FDA0003002291170000081
Figure FDA0003002291170000091
the compounds represented by the formulae P-94 to P-186 are compounds obtained by replacing O in the formulae P-1 to P-93 with S, respectively.
5. An organic electroluminescent device, characterized in that it comprises a compound according to any one of claims 1 to 4.
6. A display apparatus comprising the organic electroluminescent device according to claim 5.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160149141A1 (en) * 2014-11-21 2016-05-26 Samsung Display Co., Ltd. Amine-based compounds and organic light-emitting devices comprising the same
CN108329254A (en) * 2018-02-23 2018-07-27 王美妮 Dihydroanthracene compound, organic electroluminescence device and display device

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160149141A1 (en) * 2014-11-21 2016-05-26 Samsung Display Co., Ltd. Amine-based compounds and organic light-emitting devices comprising the same
CN108329254A (en) * 2018-02-23 2018-07-27 王美妮 Dihydroanthracene compound, organic electroluminescence device and display device

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