Triphenylene compound, intermediate and organic electroluminescent device

By designing triphenylene compounds as the main material for the OLED light-emitting layer or the electron blocking layer, the problems of low efficiency and short lifespan of OLED devices have been solved, achieving the effects of lower driving voltage, higher current efficiency and longer lifespan.

CN121895277APending Publication Date: 2026-04-21FUYANG SINEVA MATERIAL TECHNOLOGY CO LTD
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Patent Information

Application Number
CN202511726243.8
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2025-11-24
Publication Date
2026-04-21

AI Technical Summary

Technical Problem

The low efficiency and short lifespan of existing OLED devices are mainly due to the insufficient performance of organic electroluminescent materials.

Method used

We designed triphenylene compounds as the main material for the OLED light-emitting layer or the electron blocking layer, and optimized their structure to improve device performance.

Benefits of technology

This achieves lower driving voltage, higher current efficiency, and longer lifespan for OLED devices.

✦ Generated by Eureka AI based on patent content.

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Abstract

The invention provides a triphenylene compound, an intermediate and an organic electroluminescent device, and relates to the technical field of organic electroluminescent materials. According to the invention, the structure of the triphenylene compound is designed, so that the triphenylene compound can be used as a luminescent layer main body material or an electron blocking layer material of the OLED luminescent device, and the OLED luminescent device has relatively low driving voltage, relatively high current efficiency and relatively long service life.
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Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescent materials technology, specifically relating to a triphenylene compound, an intermediate, and an organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are devices fabricated by depositing one or more layers of organic material between two metal electrodes via spin coating or vacuum evaporation. A classic three-layer OLED comprises a hole transport layer, an emissive layer, and an electron transport layer. Holes generated by the anode combine with electrons generated by the cathode via the electron transport layer in the emissive layer to form excitons, which then emit light. OLEDs can be tuned to emit various desired light colors by changing the material of the emissive layer.

[0003] Organic light-emitting diodes (OLEDs), as a novel display technology, possess unique advantages such as self-illumination, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, fast response speed, wide applicable temperature range, low driving voltage, the ability to manufacture flexible, bendable, and transparent display panels, and environmental friendliness. They can be applied to flat panel displays and next-generation lighting, and can also be used as backlights for LCDs.

[0004] Since their invention in the late 1980s, organic light-emitting diodes (OLEDs) have been used in various industries, such as as screens in cameras and mobile phones. However, current OLED devices suffer from low efficiency and short lifespan, limiting their wider application, especially in large-screen displays. Therefore, it is necessary to improve device efficiency. A key factor limiting device efficiency is the performance of the organic light-emitting materials used in OLEDs. Thus, it is essential to develop stable and efficient organic light-emitting materials to improve the current efficiency and lifespan of OLED devices. Summary of the Invention

[0005] To address the shortcomings of existing technologies, the present invention aims to provide a triphenylene oxide compound, an intermediate, and an organic electroluminescent device. By designing the structure of the triphenylene oxide compound, the present invention enables it to serve as the main material for the light-emitting layer or the electron blocking layer material in an OLED light-emitting device, thereby giving the OLED light-emitting device lower driving voltage, higher current efficiency, and longer lifespan.

[0006] To achieve this objective, the present invention adopts the following technical solution:

[0007] In a first aspect, the present invention provides a triphenylene compound having the structure shown in Formula I:

[0008]

[0009] Formula I;

[0010] In Formula I, L is selected from any one of the following: single bond, substituted or unsubstituted C6~C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40) arylene, and substituted or unsubstituted C12~C40 (e.g., C12, C16, C20, C24, C28, C30, C32, C36 or C40) heteroarylene;

[0011] Z is selected from O or S;

[0012] Ar1 is selected from any one of substituted or unsubstituted C6~C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40) aryl, or substituted or unsubstituted C12~C40 (e.g., C12, C16, C20, C24, C28, C30, C32, C36 or C40) heteroaryl;

[0013] The substituents are each independently selected from any one of deuterium, F, cyano, C1-C12 alkyl, C6-C40 aryl, and C12-C40 heteroaryl.

[0014] n is selected from 0 or 1;

[0015] In the compound of Formula I, each hydrogen atom can be independently replaced by a deuterium atom, F, cyano, C1-C12 (e.g., C1, C2, C4, C6, C10 or C12) alkyl, C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40) aryl, or C12-C40 (e.g., C12, C16, C20, C24, C28, C30, C32, C36 or C40) heteroaryl.

[0016] This invention designs the structure of triphenylene compounds so that they can be used as the main material of the light-emitting layer or the electron blocking layer material of OLED light-emitting devices, thereby enabling OLED light-emitting devices to have lower driving voltage, higher current efficiency and longer lifespan.

[0017] In this invention, "D" represents a deuterium atom, and the same applies below.

[0018] In this invention, when the substituted or unsubstituted group contains substituents, the number of substituents can be one or more. For example, the substituted fluorene group can be 9,9-dimethylfluorene group, in which case it can be considered that there are two methyl substituents at the 9-position of the fluorene group. When two or more substituents are simultaneously substituted on the group, these two or more substituents can be the same or different.

[0019] Preferably, the C6-C40 arylene group is selected from any one of phenylene, biphenylene, naphthylene, anthraceneylene, and fluoreneylene.

[0020] Preferably, the C12-C40 heteroaryl group is selected from any one of imidazolyl, dibenzofuranyl, and dibenzothiazolyl.

[0021] Preferably, the C6-C40 aryl group is selected from any one of phenyl, biphenyl, naphthyl, and fluorenyl.

[0022] Preferably, the C12-C40 heteroaryl group is selected from any one of dibenzofuranyl, dibenzothiazolyl, and carbazoleyl.

[0023] In this invention, C1-C12 alkyl groups include C1-C12 straight-chain or branched alkyl groups and C3-C12 cycloalkyl groups. Preferably, the C1-C12 alkyl groups are selected from any one of methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, pentyl, cyclohexyl, octyl, adamantyl, undecyl, or dodecyl; preferably, the C1-C12 alkyl groups are selected from any one of methyl, ethyl, propyl, n-butyl, tert-butyl, pentyl, or cyclohexyl.

[0024] Preferably, the substituents are each independently selected from any one of deuterium, phenyl, and naphthyl.

[0025] Preferably, the hydrogen atoms in the compound of formula I can be independently replaced by deuterium atoms, phenyl groups, or naphthyl groups.

[0026] Preferably, the triphenylene compounds have the structures shown in Formulas I-1 to I-4:

[0027] ;

[0028] In Equations I-1 to I-2, Z and L have the same defined range as in Equation I;

[0029] In Equations I-3 to I-4, Z, L, and Ar1 have the same defined range as in Equation I;

[0030] In the compounds of Formula I-1 to Formula I-4, the hydrogen atoms can be independently replaced by deuterium atoms, F, cyano, C1 to C12 (e.g., C1, C2, C4, C6, C10 or C12) alkyl, C6 to C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40) aryl or C12 to C40 (e.g., C12, C16, C20, C24, C28, C30, C32, C36 or C40) heteroaryl.

[0031] Preferably, the triphenylene compound is selected from any one of the following substituted or unsubstituted compounds:

[0032] ;

[0033] The substitution refers to the fact that each hydrogen atom in the above compound can be independently replaced by a deuterium atom.

[0034] Preferably, the triphenylene compound is selected from any one of the following substituted or unsubstituted compounds:

[0035] , , , , , , , , , , ;

[0036] The substitution refers to the fact that each hydrogen atom in the above compound can be independently replaced by a deuterium atom.

[0037] It should be noted that the present invention does not impose any special restrictions on the synthesis method of the triphenylene compounds shown in Formula I, and commonly used synthesis methods in the art are applicable.

[0038] In a second aspect, the present invention provides an intermediate comprising the following compounds:

[0039] ;

[0040] The intermediate is used to prepare triphenylene compounds as described in the first aspect.

[0041] Thirdly, the present invention provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode, the organic thin film layer comprising triphenylene compounds as described in the first aspect.

[0042] Preferably, the organic thin film layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes the triphenylene compounds.

[0043] Preferably, the light-emitting layer further includes a dopant material. The present invention does not impose any special limitations on the specific selection of the dopant material; commonly used dopant materials in the art are applicable. Preferably, the dopant material includes compounds having the structure shown in Formula II and / or compounds having the structure shown in Formula III:

[0044]

[0045] Mode Formula III;

[0046] Mode in Ar 21 Ar 22 Each is independently selected from any one of substituted or unsubstituted C6~C20 (e.g., C6, C8, C10, C12, C16 or C20) aryl, substituted or unsubstituted C3~C20 (e.g., C3, C6, C8, C10, C12, C16 or C20) heteroaryl;

[0047] R 21 R 22 R 23 Each is independently selected from hydrogen, C1-C12 (e.g., C1, C2, C4, C6, C8, C10 or C12) straight-chain or branched alkyl groups, and C6-C12 (e.g., C6, C8, C10 or C12) cycloalkyl groups;

[0048] Ar 21 Ar 22 In this context, each of the substituents is independently selected from C1-C5 straight-chain or branched alkyl groups (e.g., methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl) or C6-C12 aryl groups (e.g., phenyl, diphenyl, naphthyl).

[0049] In Formula III, Ar 31 Ar 32 Ar 33 Ar 34 Each is independently selected from any one of substituted or unsubstituted C6~C22 (e.g., C6, C8, C10, C16, C18 or C22) aryl, substituted or unsubstituted C12~C40 (e.g., C12, C18, C20, C24, C30, C36 or C40) heteroaryl;

[0050] R 31 Selected from any one of phenyl, naphthyl, or biphenyl;

[0051] a is selected from 0 or 1;

[0052] Ar 31Ar 32 Ar 33 Ar 34 In this context, each of the substituents is independently selected from C1-C5 straight-chain or branched alkyl groups (e.g., methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl) or C6-C12 (e.g., C6, C8, C10, or C12) aryl groups.

[0053] Preferably, the Ar 21 Ar 22 Each independently selected , , , , , , , , , , , , , , , , Any of the following, with dashed lines representing connection points.

[0054] Preferably, the R 21 R 22 R 23 Each is independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl, or adamantyl.

[0055] Preferably, the Ar 31 Ar 32 Ar 33 Ar 34 Each independently selected , , , , , , , , , Any one or at least two of the above, with dashed lines indicating connection sites.

[0056] Preferably, the compound of formula II is selected from any one of the following compounds:

[0057] .

[0058] Preferably, the compound of formula III is selected from any one of the following compounds:

[0059] .

[0060] Preferably, when the light-emitting layer comprises a host material and a dopant material, the volume percentage of the benzene-anthracene compound in the light-emitting layer is 60% to 99.9% (e.g., 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 98%, 99.9%), and the volume percentage of the dopant material is 0.1% to 40% (e.g., 0.1%, 2%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%).

[0061] Preferably, the organic thin film layer includes an electron blocking layer, which includes the triphenylene compounds.

[0062] Fourthly, the present invention provides a display device comprising the organic electroluminescent device as described in the third aspect.

[0063] Compared with the prior art, the present invention has the following beneficial effects:

[0064] This invention designs the structure of triphenylene compounds and uses them as the main material for the light-emitting layer or the electron blocking layer material of OLED devices, thereby enabling OLED devices to have lower driving voltage, higher current efficiency and longer lifespan. Detailed Implementation

[0065] To facilitate understanding of the present invention, the following embodiments are provided. Those skilled in the art should understand that these embodiments are merely illustrative and should not be construed as limiting the scope of the invention.

[0066] Preparation Example 1

[0067] This preparation example provides intermediate P1-2 and its synthesis method, which is as follows:

[0068]

[0069] In a nitrogen atmosphere, 0.01 mol of intermediate P1-0 and 50 mL of tetrahydrofuran were added to a 250 mL three-necked flask. The temperature was then lowered to -78 °C, and 6.3 mL of a hexane solution of butyllithium (containing 0.01 mol of butyllithium) was slowly added. The mixture was kept at -78 °C to -60 °C for 30 min. A mixed solution of trimethyl borate and tetrahydrofuran (obtained by mixing 0.12 mol of trimethyl borate and 10 mL of tetrahydrofuran) was added, and the mixture was slowly heated to room temperature for 2 hours. The mixture was then cooled, and ammonium chloride aqueous solution and ethyl acetate were added for separation. The organic layer was washed with water until neutral, dried with anhydrous magnesium sulfate, and the drying agent was removed. The mixture was then concentrated to dryness, and petroleum ether was added for stirring and washing. After filtration, intermediate P1-2 (1.1 g) was obtained.

[0070] Preparation Example 2

[0071]

[0072] In a three-necked flask, under nitrogen protection, add 0.5 g of intermediate P1-2 and 0.15 g of pinacol ( ), 30 mL of petroleum ether, heated under reflux for 4 hours, cooled to precipitate solid, filtered to obtain intermediate P1-2EA (0.11 g).

[0073] Mass spectrometry analysis of intermediate P1-2EA showed a mass-to-charge ratio (m / z) of 394.17.

[0074] Preparation Example 3

[0075]

[0076] Under nitrogen protection, 80 mL of toluene, 30 mL of ethanol, and 20 mL of water were added sequentially to a three-necked flask. Then, 3.1 g of intermediate P1-2, 2.3 g of p-dibromobenzene, 2.12 g of sodium carbonate, and 0.23 g of tetrakis(triphenylphosphine)palladium were added. The mixture was slowly heated to reflux for 8 h, cooled to room temperature, and water was added to dissolve the organic layer. The organic layer was washed with water and dried with magnesium sulfate. After removing the desiccant, the mixture was concentrated to dryness and crystallized with toluene to obtain 2.9 g of intermediate P1-1.

[0077] The obtained intermediate P1-1 was subjected to mass spectrometry, and the mass-to-charge ratio (m / z) was measured to be 422.03.

[0078] Preparation Examples 4-5

[0079] Preparation Examples 4-5 provide an intermediate and its synthesis method, respectively. The synthesis method is the same as that of intermediate P1-1 provided in Preparation Example 1. The mass spectra of the prepared intermediates were tested, as detailed in Table 1 below.

[0080] Table 1

[0081]

[0082] Synthesis Example 1

[0083] This synthetic example provides compound P1 and its synthetic method, which is as follows:

[0084]

[0085] Compound P1 was prepared by referring to the synthesis method of intermediate P1-1.

[0086] The obtained compound P1 was analyzed by mass spectrometry, and the mass-to-charge ratio (m / z) was found to be 570.20.

[0087] Synthesis Examples 2-3

[0088] Synthesis Examples 2 and 3 respectively provide a triphenylene compound and its synthesis method. The synthesis method of the triphenylene compound is the same as that of compound P1 provided in Synthesis Example 1. The mass spectra of the prepared triphenylene compounds were tested, as detailed in Table 2 below.

[0089] Table 2

[0090]

[0091] Synthesis Example 4

[0092] This synthetic example provides compound EB1 and its synthetic method, which is as follows:

[0093]

[0094] Under nitrogen protection, dry toluene (70 mL), intermediate EBM1 (3.5 g), EBM2 (4.1 g), Pd(dba)2 (bis(dibenzylacetone)palladium, 0.0575 g), a toluene solution of 0.4 g of tri-tert-butylphosphine (containing 0.0002 mol of tri-tert-butylphosphine), and sodium tert-butoxide (1.44 g) were added to a three-necked flask. The mixture was heated to reflux and reacted for 12 h. After cooling to room temperature, water was added to dissolve the mixture. The organic layer was then washed with water until neutral, dried with magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, and crystallized with toluene to obtain compound EB1 (3.8 g).

[0095] Mass spectrometry analysis of compound EB1 showed a mass-to-charge ratio (m / z) of 661.24.

[0096] Synthesis Examples 5-7

[0097] Synthesis Examples 5-7 provide a triphenylene compound and its synthesis method, respectively. The synthesis method of the triphenylene compound is the same as that of compound EB1 provided in Synthesis Example 4. The mass spectra of the prepared triphenylene compounds were tested, as detailed in Table 3 below.

[0098] Table 3

[0099]

[0100]

[0101] Other compounds for which specific synthetic steps are not listed can be prepared using common knowledge in the field, combined with the above synthetic examples.

[0102] The specific structures of the compounds used in Application Examples 1-6 and Comparative Application Examples 1-2 are shown below: , , , , , , , , , , , , , .

[0103] Application Example 1

[0104] This application example provides an organic electroluminescent device with the following structure: ITO / HTL (80nm) / BH:BD-2 (5%) (30nm) / TPBI (30nm) / Al (150nm);

[0105] The fabrication method of the above-mentioned organic electroluminescent device is as follows:

[0106] Each layer of material was placed inside a vacuum chamber, and the vacuum was evacuated to 1×10⁻⁶. -5 ~1×10 -6 Pa is sequentially vacuum-deposited onto the cleaned ITO substrate. BH:BD-2 (5%) (30nm) refers to a light-emitting layer composed of BH and BD-2 in a volume ratio of 95:5, with a thickness of 30nm. The light-emitting layer is formed by co-evaporation of BH:BD-2.

[0107] BH is the main material for blue light emission. In this application example, BH is compound P1.

[0108] In the device provided in this application example, HTL (80nm) is the hole transport layer and TPBI (30nm) is the electron transport layer.

[0109] Application Examples 2-6

[0110] Application Examples 2-6 provide an organic electroluminescent device, which differs from Application Example 1 only in that the BH material is different (as shown in Table 4 below), while the other preparation steps are the same as in Application Example 1.

[0111] Compare and contrast examples 1 and 2

[0112] Comparative Application Examples 1 and 2 provide an organic electroluminescent device, which differs from Application Example 1 only in the BH material (as shown in Table 4 below), while the other preparation steps are the same as in Application Example 1.

[0113] The test items include the brightness, driving voltage, current efficiency, and LT80 of the organic electroluminescent device; where LT80 refers to maintaining the device's initial brightness of 1000 cd / m². 2 With the current density remaining constant, the device efficiency drops to the initial luminance of 1000 cd / m². 2 The time required to achieve 80% of the corresponding efficiency. The drive voltage, current efficiency, and LT80 are all relative values ​​(based on Application Example 1).

[0114] The specific test results are shown in Table 4 below:

[0115] Table 4

[0116]

[0117] As can be seen from the above, this invention designs the structure of triphenylene compounds and uses them as the main material of the light-emitting layer of OLED devices, thereby enabling OLED devices to have lower driving voltage, higher current efficiency and longer lifespan.

[0118] The specific structures of some of the compounds used in Application Examples 7-11 and Comparative Application Examples 3-4 are as follows:

[0119] , , , , , , , , , , .

[0120] Application Example 7

[0121] This application example provides a red organic electroluminescent device, the structure of which is as follows:

[0122] ITO / HT-3 (80nm) / Electron blocking layer (10nm) / CBP:PRD-1[5%] (35nm) / ETL-1 (25 nm) / LiF (0.5nm) / Al (150 nm).

[0123] The method for fabricating the red organic electroluminescent device is as follows:

[0124] The material was placed inside a vacuum chamber, and the vacuum was evacuated to 1×10⁻⁶. -5 ~1×10 -6 Pa, the above materials are sequentially vacuum-deposited onto the cleaned ITO substrate to prepare OLED devices.

[0125] Among them, HT-3 (80nm) is the hole transport layer, and HT-3 is the hole transport material; the electron blocking layer material is compound EB1; CBP:PRD-1[5%] (35nm) is the light-emitting layer, and CBP:PRD-1[5%] means that the volume ratio of the main material CBP to the dye PRD-1 in the light-emitting layer is 95:5; ETL-1 (25 nm) is the electron transport layer; and LiF is the electron injection material.

[0126] Application Examples 8-11

[0127] Application Examples 8-11 provide a red organic electroluminescent device, which differs from Application Example 7 only in that the material of the electron blocking layer is replaced with other compounds (see Table 5 below). The other preparation steps and conditions are the same as those in Application Example 7.

[0128] Compare and contrast examples 3-4

[0129] Comparative Application Examples 3-4 provide an organic electroluminescent device, which differs from Application Example 7 only in that the material of the electron blocking layer is replaced with other compounds (see Table 5 below). The other preparation steps and conditions are the same as in Application Example 7.

[0130] Performance testing

[0131] The luminance, driving voltage, current efficiency, and LT95 of the organic electroluminescent devices provided above were tested. The current efficiency was measured at a luminance of 1000 cd / m². 2 The corresponding value, LT95, refers to maintaining an initial device current density of 10 mA / cm². 2 The time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density, while remaining constant, is given. The drive voltage, current efficiency, and LT95 are relative values ​​(based on Application Example 7). Specific test results are shown in Table 3 below:

[0132] Table 5

[0133] Electron blocking layer material <![CDATA[Brightness / (cd / m 2 )]]> Drive voltage Current efficiency LT95 Application Example 7 EB1 1000 1 1 1 Application Example 8 EB2 1000 1.05 0.96 1.09 Application Example 9 EB3 1000 0.96 0.98 0.91 Application Example 10 EB4 1000 0.87 1.03 1.03 Application Example 11 EB5 1000 0.82 0.95 0.98 Comparative Application Example 3 DEB1 1000 1.09 0.80 0.81 Comparative Application Example 4 DEB2 1000 1.23 0.73 0.62

[0134] The present invention has been illustrated with the above embodiments to describe the detailed process flow of the present invention. However, 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 improvements to the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A triphenylene derivative compound, characterized in that, The triphenylene compounds have the structure shown in Formula I: Formula I; In Formula I, L is selected from any one of single bond, substituted or unsubstituted C6~C40 arylene, or substituted or unsubstituted C12~C40 heteroarylene; Z is selected from O or S; Ar1 is selected from any one of substituted or unsubstituted C6~C40 aryl groups and substituted or unsubstituted C12~C40 heteroaryl groups; The substituents are each independently selected from any one of deuterium, F, cyano, C1-C12 alkyl, C6-C40 aryl, and C12-C40 heteroaryl. n is selected from 0 or 1; In the compound of formula I, each hydrogen atom can be independently replaced by a deuterium atom, F, cyano, C1~C12 alkyl, C6~C40 aryl, or C12~C40 heteroaryl.

2. The triphenylene derivative compound according to claim 1, characterized in that, The C6~C40 arylene groups are selected from any one of phenylene, biphenylene, naphthylene, anthraceneylene, and fluoreneylene. The C12~C40 heteroaryl group is selected from any one of carbazolyl, dibenzofuranyl, and dibenzothiazolyl; The C6~C40 aryl group is selected from any one of phenyl, biphenyl, naphthyl, and fluorenyl. The C12~C40 heteroaryl group is selected from any one of dibenzofuranyl, dibenzothiazolyl, and carbazoleyl; The C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, pentyl, cyclohexyl, octyl, adamantyl, undecyl, or dodecyl; preferably, the C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, tert-butyl, pentyl, or cyclohexyl. The substituents are each independently selected from any one of deuterium, phenyl, and naphthyl groups; In the compound of formula I, each hydrogen atom can be independently replaced by a deuterium atom, a phenyl group, or a naphthyl group.

3. The triphenylene derivative compound according to claim 1, characterized in that, The triphenylene compounds are selected from any one of the following compounds, whether substituted or unsubstituted: ; The substitution refers to the fact that each hydrogen atom in the above compound can be independently replaced by a deuterium atom.

4. The triphenylene derivative compound according to claim 1, characterized in that, The triphenylene compounds are selected from any one of the following compounds, whether substituted or unsubstituted: 、 、 、 、 、 、 、 、 、 、 ; The substitution refers to the fact that each hydrogen atom in the above compound can be independently replaced by a deuterium atom.

5. An intermediate, characterized in that, The intermediate includes the following compounds: ; The intermediate is used to prepare the triphenylene compounds as described in any one of claims 1 to 4.

6. 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, wherein the organic thin film layer includes triphenylene compounds as described in any one of claims 1 to 4.

7. The organic electroluminescent device according to claim 6, characterized in that, The organic thin film layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes the triphenylene compounds.

8. The organic electroluminescent device according to claim 7, characterized in that, The light-emitting layer further includes a doping material, which comprises a compound having a structure as shown in Formula II and / or a compound having a structure as shown in Formula III: Mode ; Formula III; Mode in Ar 21 Ar 22 Each is independently selected from any one of substituted or unsubstituted C6-C20 aryl groups or substituted or unsubstituted C3-C20 heteroaryl groups; R 21 R 22 R 23 Each is independently selected from any one of hydrogen, C1-C12 straight-chain or branched alkyl, and C6-C12 cycloalkyl; Ar 21 Ar 22 In this context, each of the substituents is independently selected from C1-C5 straight-chain or branched alkyl groups or C6-C12 aryl groups; In Formula III, Ar 31 Ar 32 Ar 33 Ar 34 Each is independently selected from any one of substituted or unsubstituted C6-C22 aryl groups or substituted or unsubstituted C12-C40 heteroaryl groups; 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 In this context, each of the substituents is independently selected from C1-C5 straight-chain or branched alkyl groups or C6-C12 aryl groups; Preferably, the Ar 21 Ar 22 Each independently selected , , , , , , , , , , , , , , , , Any of the following, with dashed lines representing connection points; Preferably, the R 21 R 22 R 23 Each is independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl, or adamantyl; Preferably, the Ar 31 Ar 32 Ar 33 Ar 34 Each independently selected , , , , , , , , , Any one or at least two of the above, with dashed lines indicating connection sites.

9. The organic electroluminescent device according to claim 8, characterized in that, The compound of formula II is selected from any one of the following compounds: ; Preferably, the compound of formula III is selected from any one of the following compounds: 。 10. The organic electroluminescent device according to claim 6, characterized in that, The organic thin film layer includes an electron blocking layer, which includes the triphenylene compounds.

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Patent Citations

  • a PHARMACEUTICAL DOSAGE FORM ADAPTED FOR ORAL ADMINISTRATION, COMPRISING DARIFENACIN, OR ONE OF ITS PHARMACEUTICALLY ACCEPTABLE SALTS, AND A PROCEDURE FOR PRODUCING IT.

    AR005231A1