An anthracene compound, an organic electroluminescent device and a display device
By designing the optimized anthracene compounds as the luminescent layer material for OLED devices, the problems of low efficiency and short service life of existing OLED devices are solved, and lower driving voltage, higher current efficiency and longer service life are achieved.
Patent Information
- Application Number
- CN202210646463.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2022-06-08
- Publication Date
- 2025-06-10
- Estimated Expiration
- 2042-06-08
AI Technical Summary
The low efficiency and short service life of existing OLED devices restrict their wider application, especially on large-screen displays.
An anthracene compound was designed, by optimizing its structure, using ortho- or para-linked substituents, and at least one benzene ring substituent is attached to the anthracene substituent as the luminescent layer material for organic electroluminescent devices.
The lower driving voltage, higher current efficiency and longer service life of organic electroluminescent devices are achieved.
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Figure BDA0003684278890000031 
Figure BDA0003684278890000041
Abstract
Description
Technical Field
[0001] The present invention belongs to the technical field of electroluminescence, and particularly relates to an anthracene compound, an organic electroluminescent device, and a display device. Background Art
[0002] Organic electroluminescence refers to the phenomenon that organic materials are excited by current and electric field to emit light under the action of an electric field. The organic light-emitting diode (OLED) is a new generation of display technology that utilizes this phenomenon for display. Since the first excellent-performance organic electroluminescent device was fabricated by Tang C.W. and Vanslyke S.A. of Kodak Company in the United States in 1987, organic electroluminescent display has attracted great interest due to its advantages.
[0003] An organic electroluminescent device (OLED) is a device prepared by depositing an organic material between two metal electrodes by spin coating or vacuum evaporation. A classic three-layer organic electroluminescent device includes a hole transport layer, a light-emitting layer, and an electron transport layer. The holes generated from the anode combine with the electrons generated from the cathode in the light-emitting layer through the hole transport layer and the electron transport layer to form excitons, and then emit light. The organic electroluminescent device can emit various required lights by changing the material of the light-emitting layer as needed.
[0004] As a new type of display technology, the organic electroluminescent device has unique advantages such as self-luminescence, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, fast response speed, wide applicable temperature range, low driving voltage, flexible and bendable and transparent display panels can be fabricated, and environmental friendliness. It can be applied to flat panel displays and new generation lighting, and can also be used as the backlight of LCDs.
[0005] Since its invention in the late 1980s of the 20th century, organic electroluminescent devices have been industrially applied, such as being used as the screens of cameras and mobile phones, etc. However, the current OLED devices are restricted from wider applications due to factors such as low efficiency and short service life, especially for large-screen displays. Therefore, it is necessary to improve the efficiency of the devices. An important factor restricting this is the performance of the organic electroluminescent materials in the organic electroluminescent devices. In addition, when the OLED device operates under applied voltage, Joule heat is generated, making the organic materials prone to crystallization, which affects the life and efficiency of the device. Therefore, it is also necessary to develop stable and efficient organic electroluminescent materials to improve the current efficiency and service life of the OLED device. Summary of the Invention
[0006] Aiming at the deficiencies of the prior art, the purpose of the present invention is to provide an anthracene compound, an organic electroluminescent device and a display device. In the present invention, through the design of the structural formula of the anthracene compound and using this anthracene compound as the host material of the light-emitting layer, the organic electroluminescent device has a lower driving voltage, a higher current efficiency and a longer lifespan.
[0007] To achieve this purpose, the present invention adopts the following technical solutions:
[0008] In the first aspect, the present invention provides an anthracene compound, and the anthracene compound has a structure shown in formula BH-A or formula BH-B:
[0009]
[0010] Among them, in the anthracene compounds shown in formula BH-A and formula BH-B, Ar 101 each independently selects any one of a substituted or unsubstituted C6-C40 aryl group and a substituted or unsubstituted C12-C20 heteroaryl group;
[0011] In the anthracene compounds shown in formula BH-A and formula BH-B, Ar 102 each independently selects any one of -H, a substituted or unsubstituted C6-C40 aryl group and a substituted or unsubstituted C12-C20 heteroaryl group;
[0012] In the anthracene compounds shown in formula BH-A and formula BH-B, X each independently selects O or S;
[0013] In the anthracene compounds shown in formula BH-A and formula BH-B, m each independently selects 0 or 1;
[0014] Ar 101 and Ar 102 the substituents in the above-mentioned substitution each independently select at least one of -D, -F, -CN, a C1-C10 alkyl group, a C1-C6 alkoxy group or a C6-C15 aryl group;
[0015] The hydrogen atoms in the anthracene compounds shown in formula BH-A and formula BH-B can each independently be substituted by at least one of -D, -F, -CN, a C1-C6 alkoxy group or a C6-C15 aryl group.
[0016] In the present invention, through the design of the structural formula of the anthracene compound, and further through the design of the connection position of the substituent in the anthracene compound or the anthracene substituent and the heteroatom-containing substituent ( 101 where the dashed line represents the connection site of the group, the same hereinafter), making it through ortho-connection (i.e., the heteroatom-containing substituent is ) or para-connection (i.e., the heteroatom-containing substituent is ) or para-connection (i.e., the heteroatom-containing substituent is ), and at least one benzene ring substituent is connected to the other side of the anthracene substituent at the same time, and an anthracene compound with excellent performance is prepared. Using this anthracene compound as the light-emitting layer material of the organic electroluminescent device, the prepared organic electroluminescent device has a lower driving voltage, a higher current efficiency, and a longer lifespan.
[0017] In the present invention, through the design of the structure of the compound of the present invention, the material has good charge mobility, improving the voltage and efficiency of the device; at the same time, the material has strong amorphous properties, making the OLED device using this material have a good lifespan.
[0018] In the present invention, in the anthracene compounds represented by formula BH-A and formula BH-B, Ar 101 each independently selected from substituted or unsubstituted C6-C40 (such as C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) aryl, substituted or unsubstituted C12-C20 (such as C12, C14, C16, C18 or C20, etc.) heteroaryl.
[0019] In the anthracene compounds represented by formula BH-A and formula BH-B, Ar 102 each independently selected from -H, substituted or unsubstituted C6-C40 (such as C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) aryl, substituted or unsubstituted C12-C20 (such as C12, C14, C16, C18 or C20, etc.) heteroaryl.
[0020] Ar 101 and Ar 102 the substituents in are each independently selected from at least one of -D (deuterium atom), -F, -CN, C1-C10 alkyl (such as methyl, ethyl, propyl, tert-butyl, cyclopentyl, cyclohexyl or adamantyl, etc.), C1-C6 alkoxy (such as methoxy, ethoxy or propoxy, etc.) or C6-C15 aryl (such as phenyl, naphthyl, etc.).
[0021] The hydrogen atoms in the anthracene compounds represented by formula BH-A and formula BH-B can each independently be substituted by at least one of -D, -F, -CN, C1-C6 alkoxy (such as methoxy, ethoxy or propoxy, etc.) or C6-C15 aryl (such as phenyl, naphthyl, etc.).
[0022] The following are the preferred technical solutions of the present invention, but do not limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the objectives and beneficial effects of the present invention can be better achieved and realized.
[0023] As a preferred technical solution of the present invention, the aryl group of C6-C40 is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, perylenyl, spirofluorene, triphenylene, fluoranthenyl, hydrobenzanthryl, indeno[1,2-b]fluorene, benzo[ghi]fluorene, dibenzo[ghi]fluorene, naphtho[2,1-b]fluorene or benzo[naphtho[2,1-b]fluorene.
[0024] Preferably, the heteroaryl group of C12-C20 is selected from any one of dibenzofuranyl, dibenzothiophenyl, benzodibenzofuranyl, benzodibenzothiophenyl, dinaphthofuranyl or dinaphthothiophenyl.
[0025] As a preferred technical solution of the present invention, the Ar 101 is selected from any one of phenylene, di(biphenyl)ylene, 9,9-dimethylfluorenylene, dibenzothiophenylene or dibenzofuranylene, and preferably phenylene or di(biphenyl)ylene.
[0026] Preferably, the Ar 102 is selected from any one of a hydrogen atom, a deuterium atom, phenyl, naphthyl, biphenyl, dibenzothiophenyl, dibenzofuranyl, benzodibenzothiophenyl or benzodibenzofuranyl.
[0027] As a preferred technical solution of the present invention, the anthracene compound is selected from any one of the following compounds:
[0028]
[0029]
[0030]
[0031]
[0032]
[0033]
[0034]
[0035] Among them, X is selected from O or S.
[0036] It should be noted that in the present invention, there is no special limitation on the preparation method of the anthracene compounds represented by Formula BH-A or Formula BH-B. Exemplarily, it includes but is not limited to: it can be prepared by a coupling reaction to form a new carbon-carbon bond.
[0037] Preferably, the anthracene compound is selected from any one of the following compounds:
[0038]
[0039] In a second aspect, the present invention provides an electromechanical light-emitting device. The organic electroluminescent device includes an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode;
[0040] The material of the organic thin film layer includes the anthracene compound as described in the first aspect.
[0041] Preferably, the organic thin film layer includes a light-emitting layer, and the material of the light-emitting layer includes the anthracene compound as described in the first aspect.
[0042] As a preferred technical solution of the present invention, the material of the light-emitting layer further includes a compound having a structure represented by Formula II and / or a compound having a structure represented by Formula III:
[0043]
[0044] wherein, Ar 21 、Ar 22 each independently selected from a substituted or unsubstituted C6-C20 (such as C6, C8, C10, C12, C16 or C20, etc.) aryl group, a substituted or unsubstituted C3-C20 (such as C3, C6, C8, C10, C12, C16 or C20, etc.) heteroaryl group;
[0045] R 21 、R 22 and R 23 each independently selected from hydrogen, a C1-C12 (such as C1, C2, C4, C6, C8, C10 or C12, etc.) straight-chain or branched-chain alkyl group, a C6-C12 (such as C6, C8, C10 or C12, etc.) cycloalkyl group;
[0046] Ar 21 、Ar 22 the substituents in the substituted ones are each independently selected from a C1-C5 straight-chain or branched-chain alkyl group (such as methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, etc.) or a C6-C12 aryl group (such as phenyl, biphenyl, naphthyl, etc.);
[0047] Ar31 、Ar 32 、Ar 33 and Ar 34 are each independently selected from any one of substituted or unsubstituted C6-C22 (such as C6, C8, C10, C16, C18 or C22, etc.) aryl groups and substituted or unsubstituted C12-C40 (such as C12, C18, C20, C24, C30, C36 or C40, etc.) heteroaryl groups;
[0048] R 31 is selected from any one of phenyl, naphthyl or biphenyl;
[0049] a is selected from 0 or 1;
[0050] Ar 31 、Ar 32 、Ar 33 、Ar 34 The substituents in the above-mentioned substitution are each independently selected from C1-C5 straight-chain or branched-chain alkyl groups (such as methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, etc.) or C6-C12 (such as C6, C8, C10 or C12, etc.) aryl groups.
[0051] As a preferred technical solution of the present invention, the said Ar 21 、Ar 22 are each independently selected from any one of them.
[0052] Preferably, the said R 21 、R 22 and R 23 are each independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl or adamantyl.
[0053] Preferably, the said Ar 31 、Ar 32 、Ar 33 and Ar 34 are each independently selected from any one of them or a combination of at least two of them.
[0054] As a preferred technical solution of the present invention, the compound having the structure shown in Formula II is selected from any one of the following compounds:
[0055]
[0056]
[0057] As a preferred technical solution of the present invention, the compound having the structure shown in Formula III is selected from any one of the following compounds:
[0058]
[0059]
[0060] In a third aspect, the present invention provides a display device, and the display device includes the organic electroluminescent device as described in the second aspect.
[0061] Compared with the prior art, the present invention has the following beneficial effects:
[0062] In the present invention, through the design of the structure of anthracene compounds, and further through the design of the connection position of the Ar 101 substituent or anthracene substituent and the heteroatom-containing substituent in the anthracene compound, so that it is connected by ortho-linkage or para-linkage, and at least one benzene ring substituent is connected to the anthracene substituent, a kind of anthracene compound with excellent performance is prepared. Using this anthracene compound as the light-emitting layer material of the organic electroluminescent device, the prepared organic electroluminescent device has a lower driving voltage, a higher current efficiency and a longer lifespan. Specific Embodiments
[0063] To facilitate the understanding of the present invention, the following examples are listed. Those skilled in the art should understand that the examples are only for helping to understand the present invention and should not be regarded as specific limitations on the present invention.
[0064] Synthesis Example 1
[0065] This synthesis example provides a compound 3, and its preparation method is as follows:
[0066]
[0067] Under the protection of nitrogen, 100 mL of toluene, 60 mL of ethanol and 30 mL of water are successively added to a 500 mL three-necked flask, and then 3.33 g (0.01 mol) of 9-bromo-10-phenylanthracene, 2.86 g (0.01 mol) of tribenzo[1,12-bcd]furan-3-boronic acid, 2.12 g (0.02 mol) of sodium carbonate and 0.23 g (0.0002 mol) of tetrakis(triphenylphosphine)palladium are added thereto. The temperature is slowly raised to 100 °C and reacted for 12 h, then cooled to room temperature, water is added for liquid separation, the organic layer is washed with water, dried with magnesium sulfate, the desiccant is removed, concentrated to dryness, and subjected to silica gel column chromatography separation, eluted with petroleum ether:ethyl acetate = 20:1 (volume ratio) to obtain 4.1 g of compound 3.
[0068] The obtained compound 3 was detected by mass spectrometry, and the measured mass-to-charge ratio (m / z) was 494.17.
[0069] Elemental analysis was performed on the obtained compound 3. Theoretical values: C, 92.28%; H, 4.48%; O, 3.23%; Measured values: C, 92.29%; H, 4.46%.
[0070] Synthesis Example 2
[0071] This synthesis example provides a compound 19S, and its preparation method is as follows:
[0072]
[0073] The preparation method of compound 19S refers to the preparation method of compound 3 in Synthesis Example 1, with the only difference being that tribenzo[1,12-bcd]furan-3-boronic acid is replaced with an equimolar amount of Replace 9-bromo-10-phenylanthracene therein with Other conditions are the same as those in Synthesis Example 1.
[0074] The obtained compound 19S was detected by mass spectrometry, and the measured mass-to-charge ratio (m / z) was 586.18.
[0075] Synthesis Examples 3 - 12
[0076] Synthesis Examples 3 - 12 respectively provide the following compounds (see Table 1 for details). Their preparation methods refer to the preparation method of compound 3 in Synthesis Example 1, with the only difference being that 9-bromo-10-(2-naphthyl)anthracene is replaced with an equimolar amount of other bromides (see Table 1 for details), and other conditions are the same as those in Synthesis Example 1.
[0077] The obtained compounds in Synthesis Examples 3 - 12 were detected by mass spectrometry, and their mass-to-charge ratios (m / z) are shown in Table 1.
[0078] Table 1
[0079]
[0080]
[0081]
[0082]
[0083] Synthesis Example 13
[0084] This synthesis example provides a compound 25, and its preparation method is as follows:
[0085]
[0086] The preparation method of Compound 25 refers to the preparation method of Compound 3 in the examples, except that tribenzo[1,12-bcd]furan-3-boronic acid therein is replaced with an equimolar amount of tribenzo[1,12-bcd]furan-1-boronic acid, and 9-bromo-10-phenylanthracene therein is replaced with an equimolar amount of 9-bromo-10-biphenylanthracene, and other conditions are the same as those in Synthesis Example 1.
[0087] Compound 25 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 570.20.
[0088] Synthesis Examples 14 - 15
[0089] Synthesis Examples 14 - 15 respectively provide the following compounds (see Table 2 for details). The preparation method refers to the preparation method of Compound 25 in Synthesis Example 13, with the difference that 9-bromo-10-biphenylanthracene is replaced with an equimolar amount of other bromides (see Table 2 for details), and other conditions are the same as those in Synthesis Example 1.
[0090] The compounds obtained in Synthesis Examples 14 - 15 were subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) is shown in Table 2 for details.
[0091] Table 2
[0092]
[0093]
[0094] For compounds with other unlisted synthesis methods, they can be synthesized with reference to the above examples and combined with common general knowledge in the art, and the present invention will not list them one by one.
[0095] The specific structures of the materials used in the following device examples are as follows:
[0096]
[0097]
[0098] Device Example 1
[0099] This device example provides an organic electroluminescent device, using Compound 3 provided in Synthesis Example 1 as the host material of the light-emitting layer;
[0100] The structure of the organic electroluminescent device is: ITO / HIL02(100nm) / HT(40nm) / Light-emitting layer(30nm): BD - 13% / TPBI(30nm) / LiF(0.5nm) / Al(150nm).
[0101] The preparation process of the organic electroluminescent device is as follows:
[0102] The glass substrate coated with an ITO transparent conductive layer (as the anode) is ultrasonically treated in a cleaning agent, then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol, baked in a clean environment until completely dehydrated, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam on the surface to improve the surface properties and enhance the bonding ability with the hole injection layer;
[0103] Place the above-mentioned glass substrate in a vacuum chamber, evacuate to 1×10 -5 ~9×10 -4 Pa, and vacuum deposit HIL02 as the hole injection layer on the anode at a deposition rate of 0.01 nm / s, and the deposited film thickness is 100 nm;
[0104] Vacuum deposit HT as the hole transport layer on the hole injection layer at a deposition rate of 0.01 nm / s, and the deposited film thickness is 40 nm;
[0105] Vacuum deposit the light-emitting layer above the hole transport layer at a deposition rate of 0.01 nm / s, and the total deposited film thickness is 30 nm. The host materials of the light-emitting layer are the compound of the present invention and the comparative material respectively, and the doping material is BD-1. 3% refers to the doping ratio of the doping material, that is, the volume ratio of the host material of the light-emitting layer to the doping material is 97:3;
[0106] Vacuum deposit TPBI as the electron transport layer of the organic light-emitting device above the organic light-emitting layer; the deposition rate is 0.01 nm / s, and the total deposited film thickness is 30 nm;
[0107] Vacuum deposit 0.5 nm of LiF and 150 nm of Al as the electron injection layer and the cathode on the electron transport layer to obtain the organic light-emitting device.
[0108] Device Example 2-10
[0109] This device example provides an organic light-emitting device, which is different from Device Example 1 only in that the host material of the light-emitting layer is different (see Table 3 below), and other conditions are the same as those in Device Example 1.
[0110] Device Comparative Example 1-3
[0111] This device comparative example provides an organic light-emitting device, which is different from Device Example 1 only in that the host of the light-emitting layer is different (see Table 3 below), and other conditions are the same as those in Device Example 1.
[0112] Performance Test
[0113] Test method: Use the OLED-1000 multi-channel accelerated aging life and optical color performance analysis system produced by Hangzhou Yuanfang to test the driving voltage, current efficiency, and life LT90 of the OLED device provided above; among them, LT90 refers to the time required for the current density to remain unchanged while maintaining the initial brightness of 2000 nit and the brightness to drop to 90% of the original brightness.
[0114] The performance test results of the organic electroluminescent devices provided by the above device examples and device comparative examples are shown in Table 3 below:
[0115] Table 3
[0116]
[0117]
[0118] As can be seen from the content of Table 3, through the design of the structure of the anthracene compound, the present invention makes one side of the anthracene substituent adjacent or para to the heteroatom in the heteroatom-containing substituent, and the other side of the anthracene substituent is connected to a benzene ring. The prepared anthracene compound has excellent performance. Using this anthracene compound as the host material of the light-emitting layer, the prepared organic electroluminescent device has a lower driving voltage, a higher current efficiency, and a longer service life.
[0119] Device Example 11
[0120] This device example provides an organic electroluminescent device, using the compound 4 provided in Synthesis Example 3 as the host material of the light-emitting layer and BD-2 as the doping material of the light-emitting layer;
[0121] The structure of the organic electroluminescent device is: ITO / HIL02(100nm) / HT(40nm) Light-emitting layer(30nm): BD-2 3% / TPBI(30nm) / LiF(0.5nm) / Al(150nm).
[0122] The preparation process of the organic electroluminescent device is as follows:
[0123] The glass substrate coated with the ITO transparent conductive layer (as the anode) is ultrasonically treated in a cleaning agent, then rinsed in deionized water, then ultrasonically degreased in a mixed solvent of acetone and ethanol, and then baked in a clean environment until completely dehydrated, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam on the surface to improve the surface properties and enhance the bonding ability with the hole injection layer;
[0124] Place the above glass substrate in a vacuum chamber and evacuate to 1×10 -5 ~9×10 -4Pa, HIL02 was vacuum-evaporated on the anode as the hole injection layer at a deposition rate of 0.01 nm / s, and the deposited film thickness was 100 nm;
[0125] HT was vacuum-evaporated on the hole injection layer as the hole transport layer at a deposition rate of 0.01 nm / s, and the deposited film thickness was 40 nm;
[0126] The light-emitting layer was vacuum-evaporated on the hole transport layer at a deposition rate of 0.01 nm / s, and the total deposited film thickness was 30 nm. The main material of the light-emitting layer was compound 4, and the doping material was BD-2. 3% refers to the doping ratio of the doping material, that is, the volume ratio of the main material to the doping material in the light-emitting layer is 97:3;
[0127] TPBI was vacuum-evaporated on the organic light-emitting layer as the electron transport layer of the organic light-emitting device at a deposition rate of 0.01 nm / s, and the total deposited film thickness was 30 nm;
[0128] 0.5 nm of LiF and 150 nm of Al were vacuum-evaporated on the electron transport layer as the electron injection layer and the cathode to obtain the organic light-emitting device.
[0129] Device Example 12 - 13
[0130] This device example provides an organic light-emitting device, which is only different from Device Example 1 in that the doping material of the light-emitting layer is different (see Table 4 below), and other conditions are the same as those in Device Example 1.
[0131] Performance Test
[0132] Test method: Use the OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang to test the driving voltage, current efficiency, and life LT90 of the above-provided OLED device; among them, LT90 refers to the time required for the current density to remain unchanged while maintaining the initial brightness of 2000 nit and the brightness to drop to 90% of the original brightness.
[0133] The performance test results of the organic light-emitting devices provided by the above device examples and device comparative examples are shown in Table 4 below:
[0134] Table 4
[0135]
[0136] It can be seen from the content of Table 4 that the anthracene compounds provided by the present invention can be used in combination with a variety of doping materials, and the prepared organic light-emitting devices have a lower driving voltage, a higher current efficiency, and a longer service life. Especially when combined with BD-3, the effect is particularly excellent.
[0137] In summary, in the present invention, through the design of the structure of anthracene compounds, and further through the design of the connection position of the Ar 101 substituent or anthracene substituent and the heteroatom-containing substituent in the anthracene compound, so that they are connected through ortho-connection or para-connection, and at least one benzene ring substituent is connected to the anthracene substituent, an anthracene compound with excellent performance is prepared. Using this anthracene compound as the light-emitting layer material of an organic electroluminescent device, the prepared organic electroluminescent device has a lower driving voltage, a higher current efficiency, and a longer lifespan.
[0138] The applicant declares that the present invention uses the above embodiments to illustrate the detailed process flow of the present invention, but the present invention is not limited to the above detailed process flow, that is, it does not mean that the present invention must rely on the above detailed process flow to be implemented. Those skilled in the art should understand that any improvement to the present invention, the equivalent substitution of each raw material of the product of the present invention, the addition of auxiliary components, the selection of specific methods, etc., all fall within the protection scope and the disclosure scope of the present invention.
Claims
1. An anthracene compound, characterized in that, the anthracene compound includes the following compounds:
2. An organic electroluminescent device, characterized in that, the organic electroluminescent device includes an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode; the material of the organic thin film layer includes the anthracene compound as described in claim 1.
3. The organic electroluminescent device according to claim 2, characterized in that, the organic thin film layer includes a light-emitting layer, and the material of the light-emitting layer includes the anthracene compound as described in claim 1.
4. The organic electroluminescent device according to claim 3, characterized in that, the material of the light-emitting layer further includes a compound having the structure shown in Formula II and / or a compound having the structure shown in Formula III: Among them, Ar 21 and Ar 22 are each independently selected from any one of substituted or unsubstituted C6-C20 aryl groups and substituted or unsubstituted C3-C20 heteroaryl groups; R 21 , R 22 and R 23 are each independently selected from any one of hydrogen, C1-C12 straight-chain or branched-chain alkyl, and C6-C12 cycloalkyl; Ar 21 、Ar 22 The substituents described in 21 and 22 are each independently selected from C1-C5 straight-chain or branched-chain alkyl groups or C6-C12 aryl groups; Ar 31 、 Ar 32 、 Ar 33 and Ar 34 each independently selected from any one of substituted or unsubstituted C6-C22 aryl, substituted or unsubstituted C12-C40 heteroaryl; R 31 Selected from any one of phenyl, naphthyl or biphenyl; a is selected from 0 or 1; Ar 31 、Ar 32 、Ar 33 、Ar 34 The substituents in each of the above-mentioned substitutions are independently selected from C1-C5 straight-chain or branched-chain alkyl groups or C6-C12 aryl groups.
5. The organic electroluminescent device according to claim 4, characterized in that, The said Ar 21 、Ar 22 are each independently selected from Any one of 6. The organic electroluminescent device according to claim 4, characterized in that, The R 21 , R 22 and R 23 are each independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl or adamantyl.
7. The organic electroluminescent device according to claim 4, characterized in that, Ar 31 、Ar 32 、Ar 33 and Ar 34 each independently selected from any one of 8. The organic electroluminescent device according to claim 4, characterized in that, the compound having the structure shown in Formula II is selected from any one of the following compounds:
9. A display device, characterized in that, the display device includes the organic electroluminescent device according to any one of claims 2-8.
Citation Information
Patent Citations
APPARATUS AND METHOD FOR FORMING A PART OF A CONTAINER AND FORMED CONTAINER, AND FORMING MANDREL USING SUCH APPARATUS.
AR005031A1
Multiple host materials, composition comprising same, and organic electroluminescent device comprising same
CN114447242A
Anthracene compound, organic electroluminescent device and display device
CN114853703A