A compound containing a triazine structure and an organic electroluminescence device
Patent Information
- Application Number
- CN202410561834.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2024-05-08
- Publication Date
- 2026-09-15
- Estimated Expiration
- 2044-05-08
AI Technical Summary
就当前有机电致发光产业的实际需求而言,目前有机电致发光材料的发展还远远不够,远远落后于面板制造企业的要求,因此,亟需一种效率高、稳定性好的有机电致发光器件
[0061] This invention designs a novel class of organic electroluminescent materials, which have the following characteristics:
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Figure CN118420625B_ABST
Abstract
Description
Technical Field
[0001] This invention relates to the field of organic electroluminescence technology, specifically to a compound containing a triazine structure and an organic electroluminescent device. Background Technology
[0002] Organic light emission (OLED) typically refers to the phenomenon of converting electrical energy into light energy using organic materials. OLED devices generally have a structure comprising an anode and a cathode, with an organic layer between them. To improve the efficiency and stability of OLEDs, the organic layer is often formed by a multilayer structure composed of different materials; for example, it can consist of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such an OLED structure, if a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, they form excitons. When these excitons re-enter the ground state, they emit light.
[0003] OLEDs are current-driven organic light-emitting devices that emit light through the injection and recombination of charge carriers. The luminous intensity is directly proportional to the injected current. Under the influence of an electric field, holes generated at the anode and electrons at the cathode move and are injected into the hole transport layer and electron transport layer, respectively, migrating to the emissive layer. When these two electrons meet in the emissive layer, they generate excitons, which excite the light-emitting molecules to ultimately produce visible light.
[0004] OLEDs offer a wide field of view, reaching approximately 170 degrees, while LCDs require light to be blocked during operation, creating natural viewing obstacles at certain angles. OLEDs, being self-emissive, also boast a much wider field of view. Currently, the development of organic electroluminescent materials is far from meeting the actual needs of the organic electroluminescent industry, lagging significantly behind the requirements of panel manufacturers. Therefore, there is an urgent need for a highly efficient and stable organic electroluminescent device. Summary of the Invention
[0005] The purpose of this invention is to provide a compound containing a triazine structure and an organic electroluminescent device, based on the prior art.
[0006] The technical solution of the present invention is as follows:
[0007] A compound containing a triazine structure has the chemical structural formula shown in Formula 1:
[0008]
[0009] in,
[0010] L1-L3 are each independently a single bond or a substituted or unsubstituted C6-C20 aryl group, and the substituent is selected from one or more of deuterium, fluorine, cyano, C6-C30 aryl, C6-C30 deuterated aryl, and C5-C30 heteroaryl.
[0011] Ar1 and Ar2 are substituted or unsubstituted groups of the following: C6-C30 aryl or C5-C30 heteroaryl, wherein the substituent is selected from one or more of deuterium, fluorine, cyano, C1-C10 alkyl, C1-C10 deuterated alkyl, C6-C30 aryl, C6-C30 deuterated aryl, and C5-C30 heteroaryl;
[0012] R1-R3 are each independently hydrogen, deuterium, fluorine, cyano, C1-C10 alkyl, C1-C10 deuterated alkyl, C6-C20 aryl or C6-C20 deuterated aryl.
[0013] o is a positive integer between 0 and 5;
[0014] n and m are positive integers between 0 and 6.
[0015] In a preferred embodiment of the present invention, the compound of the present invention has the structural formula shown in Formula 2 below:
[0016]
[0017] in,
[0018] Ar1 and Ar2 are substituted or unsubstituted groups of the following: aryl (C6-C18) or heteroaryl (C5-C24), wherein the substituent is selected from one or more of deuterium, fluorine, cyano, alkyl (C1-C6), deuterated alkyl (C1-C6), aryl (C6-C18), deuterated aryl (C6-C18), and heteroaryl (C5-C24);
[0019] Preferably, Ar1 and Ar2 are substituted or unsubstituted groups of the following: phenyl, biphenyl, anthryl, dibenzofuranyl, dibenzothiophene, fluorenyl, phenanthryl, benzophenanthrenefuranyl, wherein the substituent is selected from one or more of deuterium, fluorine, cyano, C6-C12 aryl, C6-C12 deuterated aryl, and C5-C20 heteroaryl;
[0020] More preferably, Ar1 and Ar2 are substituted or unsubstituted groups of the following: phenyl, biphenyl, anthryl, dibenzofuranyl, dibenzothiopheneyl or benzophenanthrenefuranyl, wherein the substituent is selected from one or more of deuterium, fluorine, cyano, C6-C12 aryl, and C6-C12 deuterated aryl.
[0021] More preferably, Ar1 and Ar2 are substituted or unsubstituted groups of the following: phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, wherein the substituent is selected from one or more of deuterium, phenyl, and biphenyl.
[0022] In a preferred embodiment, L1 and L2 are independently single-bonded or substituted or unsubstituted phenyl, naphthyl, or biphenyl, and the substituents are selected from one or more of deuterium, fluorine, cyano, C6-C30 aryl, C6-C30 deuterated aryl, and C5-C30 heteroaryl.
[0023] Preferably, L1 and L2 are independently single-bonded or substituted or unsubstituted phenyl, naphthyl, or biphenyl, and their substituents are selected from one or more of deuterium, fluorine, cyano, C6-C30 aryl, and C5-C30 heteroaryl.
[0024] More preferably, L1 and L2 are independently single bonds or substituted or unsubstituted phenyl, naphthyl, or biphenyl groups, and the substituents are selected from one or more of deuterium, fluorine, and cyano groups;
[0025] More preferably, L1 and L2 are independently single bonds or substituted or unsubstituted phenyl or biphenyl groups.
[0026] Furthermore, the compound of the present invention can be any one of the following compounds:
[0027]
[0028]
[0029]
[0030]
[0031]
[0032]
[0033]
[0034]
[0035]
[0036]
[0037]
[0038]
[0039] An organic electroluminescent device includes a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode;
[0040] Further, the organic layer comprises a hole injection layer, a first hole transport layer, a second hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; at least one of the hole injection layer, the first hole transport layer, the second hole transport layer, the light-emitting layer, the hole blocking layer, the electron transport layer, and the electron injection layer contains a compound as described in any one of claims 1-6.
[0041] Furthermore, the light-emitting layer contains the aforementioned compound.
[0042] Furthermore, the light-emitting layer contains a light-emitting host material, which is composed of one or more of the above-mentioned compounds and the following P-Type compounds, as shown below:
[0043]
[0044]
[0045] An electronic display device containing the aforementioned organic electroluminescent device.
[0046] An OLED lighting device containing the aforementioned organic electroluminescent device.
[0047] The room temperature described in this invention is 25±5℃.
[0048] Unless otherwise stated, the following terms used in the claims and description shall have the following meanings.
[0049] Embodiments of various aspects are further illustrated and described below. It should be understood that the description herein is not intended to limit the claims to the specific aspects described. Rather, it is intended to cover substitutions, modifications, and equivalents that may be included within the spirit and scope of this disclosure as defined by the appended claims.
[0050] As used herein, in the terms “deuterated” and “undeuterated,” the term “deuterated” means that at least one hydrogen in the group is recoordinated with deuterium. The term “undeuterated” means that none of the hydrogens in the group are recoordinated with deuterium.
[0051] In this document, "aromatic group," "aryl," or "aromatic group" refers to a group containing one or more aromatic rings, including but not limited to benzene, naphthalene, phenanthrene, fluorene, acenaphthene, pyridine, pyrrole, furan, thiophene, etc. In C6-C30 aromatic groups, C6-C30 means that the group contains 6-30 carbon atoms. In C1-C10 alkyl-substituted C6-C20 aromatic groups, C1-C10 refers to the number of carbon atoms in the substituent, and C6-C20 refers to the number of carbon atoms in the unsubstituent aromatic group. Aromatic groups can be divided into monocyclic aryl and polycyclic aryl groups. Specific aromatic groups in this invention include, but are not limited to, phenyl, biphenyl, terphenyl, anthracene, naphthyl, phenanthrene, fluorenyl, dibenzofuranyl, dibenzothiophene, 9,9-spirodifluorenyl, 9,9-dimethylfluorenyl, or 9,9-diphenylfluorenyl, etc. Aromatic groups can be substituted or unsubstituted.
[0052] As used herein, "cycloalkyl" refers to a monocyclic or fused ring group consisting entirely of carbon atoms (a "fused" ring means that each ring in the system shares an adjacent pair of carbon atoms with other rings in the system), wherein one or more rings are saturated alicyclic rings, generally having 3-20 carbon atoms, preferably 3-12 carbon atoms, and more preferably 3-10 carbon atoms. Cycloalkyl groups can be classified into monocyclic alkyl groups having only one ring and fused alkyl groups having multiple rings. Examples of monocyclic alkyl groups include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, and cycloheptane. Cycloalkyl groups can be substituted or unsubstituted.
[0053] As used herein, "cycloalkenyl" refers to a monocyclic or fused ring group consisting entirely of carbon (a "fused" ring means that each ring in the system shares a pair of adjacent carbon atoms with other rings in the system), wherein one or more rings do not have a fully connected π-electron system and contain at least one alkenyl group, which generally has 3-20 carbon atoms, preferably 3-12 carbon atoms, more preferably 3-10 carbon atoms. Examples of cycloalkenyl groups include, but are not limited to, cyclopentene, cyclohexene, cyclohexadiene, and cycloheptanetriene. The cycloalkenyl group can be substituted or unsubstituted.
[0054] "Deuterated phenyl" refers to a group in which the hydrogen atom attached to the C ring atom on the benzene ring is replaced by deuterium. It can be monosubstituted or polysubstituted, such as monodeuterated phenyl, pentadeuterated phenyl, etc.
[0055] In this article, "o is an integer from 0 to 5" means that n can be 0, 1, 2, 3, 4, or 5 on its own.
[0056] In this article, "n and m are integers from 0 to 6" means that n and m can be 0, 1, 2, 3, 4, 5, or 6 on their own.
[0057] In this article, "heteroaryl" refers to a heteroaryl group obtained by substituting one or more carbon atoms (C) in the structure of an "aryl" group with one or more heteroatoms (such as N, O, or S). A "heteroaryl" is a structural unit consisting of at least one aromatic ring and at least one heteroatom (usually nitrogen, oxygen, sulfur, or silicon), which can exist alone or in combination with other heteroaryl structures or organic groups. The aromatic ring in a heteroaryl structure is typically a benzene ring, thiophene ring, pyrrole ring, etc., while the non-aromatic ring group includes elements such as oxygen, nitrogen, and sulfur. All or part of a heteroaryl group has a fully conjugated π-electron system. The number of carbon ring atoms in a heteroaryl group can be expressed in C6-20 or similar ways. For example, a C3-C30 heteroaryl group means that the number of carbon ring atoms in the heteroaryl group can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, etc., up to 30. Based on the number of carbon ring atoms, heteroaryl groups can be C3-C30, C3-C16, C3-C12, C3-10, C3-C9, C3-C8, C3-C7, C8-C16, etc. Non-limiting examples of heteroaryl groups include, but are not limited to, furanyl, imidazolyl, pyridyl, pteridinyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, quinolinyl, isoquinolinyl, etc.
[0058] Unless otherwise specified in the examples, the procedures should be performed under standard conditions or conditions recommended by the manufacturer. Reagents or instruments whose manufacturers are not specified are all commercially available products.
[0059] The advantages of using the technical solution of this invention are as follows:
[0060] The beneficial effects of this invention are:
[0061] This invention designs a novel class of organic electroluminescent materials, which have the following characteristics:
[0062] 1. The compounds of this invention have excellent thermal and chemical stability, thereby effectively improving the stability and lifespan of the devices.
[0063] 2. The compound of the present invention has strong rigidity, which can effectively reduce non-radiative transitions of molecules and improve the luminous efficiency of the device.
[0064] 3. All compounds in this invention have a certain torque and conjugation degree, and thus possess suitable triplet energy levels, making them more suitable for use as RH. These triplet energy levels can be better matched with RD, which is beneficial for the transfer of energy from RH to RD, thereby improving the luminous efficiency and lifespan of the device.
[0065] 4. Device verification shows that devices prepared using the compounds of this invention all have good luminous efficiency and lifetime. Attached Figure Description
[0066] Figure 1 This is a schematic diagram of the structure of the organic electroluminescent device of the present invention.
[0067] The numbers in the diagram represent: 1-anode, 2-hole injection layer, 3-first hole transport layer, 4-second hole transport layer, 5-light-emitting layer, 6-hole blocking layer, 7-electron transport layer, 8-electron injection layer, and 9-cathode.
[0068] Figure 2 This is an HPLC chromatogram of compound 1 prepared in Example 1 of the present invention.
[0069] Figure 3 The DSC spectrum of compound 1 prepared in Example 1 of this invention is shown below. Figure 3 It can be seen that the Tg value of compound 1 is 131.54℃.
[0070] Figure 4 The TGA spectrum of compound 1 prepared in Example 1 of this invention is shown below. Figure 1 It can be seen that the thermogravimetric temperature Td is 493.00℃. Detailed Implementation
[0071] Embodiments of various aspects are further illustrated and described below. It should be understood that the description herein is not intended to limit the claims to the specific aspects described. Rather, it is intended to cover substitutions, modifications, and equivalents that may be included within the spirit and scope of this disclosure as defined by the appended claims.
[0072] Unless otherwise specified in the examples, the procedures should be performed under standard conditions or conditions recommended by the manufacturer. Reagents or instruments whose manufacturers are not specified are all commercially available products.
[0073] Example 1:
[0074]
[0075] The synthesis method of compound 1 is as follows:
[0076]
[0077]
[0078] Under nitrogen protection, benzocarbazole compound 1-a (29.6 g, 0.1 mol, 1 eq), 2-bromo-3-chloronaphthalene 1-b (24.15 g, 0.1 mol, 1 eq), 400 ml of toluene, sodium tert-butoxide (14.4 g, 0.15 mol, 1.5 eq), Pd2(dba)3 (0.916 g, 0.001 mol, 1% eq), and 10% tri-tert-butylphosphine toluene solution (4 ml, 0.002 mol, 2% eq) were added to the reaction flask. After the addition was complete, the reaction solution was heated to reflux and reacted for 12 h. After cooling, 100 ml of water was added, the mixture was separated, and the organic phase was concentrated to dryness. Column chromatography was performed to obtain approximately 35.8 g of intermediate 1-c, with a yield of 78%.
[0079] Under nitrogen protection, intermediate 1-c (35.8 g, 0.078 mol, 1 eq), 500 ml of DMAC, potassium carbonate (21.52 g, 0.156 mol, 2 eq), palladium acetate (0.88 g, 0.0039 mol, 5% eq), and tricyclohexylphosphine tetrafluoroborate (2.87 g, 0.0078 mol, 10% eq) were added to the reaction flask. After the addition was complete, the temperature was raised to 120 °C and the reaction was carried out for 12 h. After the reaction was completed, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The liquid was separated, the organic phase was concentrated to dryness, and purified by column chromatography, yielding approximately 18.4 g of intermediate 1-d, with a yield of 56.12%.
[0080] Under nitrogen protection, intermediate 1-d (18.4 g, 0.044 mol, 1 eq), o-nitrophenylboronic acid 1-e (7.3 g, 0.044 mol, 1 eq), toluene (200 ml), ethanol (50 ml), potassium carbonate (18.22 g, 0.132 mol, 3 eq), water (50 ml), and tetra-triphenylphosphine palladium (0.51 g, 0.00044 mol, 1% eq) were added to the reaction flask. After the addition was complete, the reaction solution was heated to 85 °C and reacted for 6 h. Water was added to the reaction solution, the mixture was separated, and the organic phase was concentrated to dryness. Column chromatography purified the solution to 14.1 g of intermediate 1-f, with a yield of 69.28%.
[0081] Intermediate 1-f (14.1 g, 0.03 mol, 1 eq) and 300 ml of triethyl phosphite were added to the reaction flask. After the addition was complete, the temperature was raised to 140 °C and the reaction was carried out for 12 h. After the reaction was completed, the reaction solution was concentrated, added to ethanol, cooled and filtered. After drying the filter cake, 10 g of intermediate 1-f was obtained, with a yield of 77.4%.
[0082] Under nitrogen protection, intermediate 1-g (10g, 0.023mol, 1eq), triazine compound 1-h (8.3g, 0.023mol, 1eq) were added to 200ml of toluene, followed by sodium tert-butoxide (3.3g, 0.0345mol, 1.5eq), Pd2(dba)3 (0.21g, 0.00023mol, 1%eq), and a 10% toluene solution of tri-tert-butylphosphine (0.9ml, 0.00046mol, 2%eq). After the addition was complete, the mixture was heated to 110℃ and reacted for 4h. After the reaction was complete, the mixture was cooled, 100ml of water was added, and the mixture was filtered. The toluene in the filter cake was recrystallized to give 9g of product 1, with a yield of 52%.
[0083] The following product compounds were obtained in a similar manner:
[0084] Table 1
[0085]
[0086]
[0087]
[0088]
[0089]
[0090]
[0091]
[0092] The results of the synthesis and identification of the compounds prepared in Table 1 above are shown in Table 2 below:
[0093] Table 2
[0094] 1 m / z = 751.14 (C₅₃H₂₉N₅O = 751.24) 72 m / z = 903.22 (C₆₅H₃₇N₅O = 903.30) 4 m / z = 715.12 (C₅₃H₂₉N₅O = 751.24) 80 m / z = 903.22 (C₆₅H₃₇N₅O = 903.30) 5 m / z = 827.23 (C₅₉H₃₃N₅O = 827.27) 94 m / z = 903.24 (C₆₅H₃₇N₅O = 903.30) 10 m / z = 827.24 (C₅₉H₃₃N₅O = 827.27) 108 m / z = 919.12 (C₆₅H₃₇N₅S = 919.28) 13 m / z = 827.22 (C₅₉H₃₃N₅O = 827.27) 120 m / z = 919.15 (C₆₅H₃₇N₅S = 919.28) 14 m / z = 827.23 (C₅₉H₃₃N₅O = 827.27) 126 m / z = 919.15 (C₆₅H₃₇N₅S = 919.28) 17 m / z = 827.21 (C₅₉H₃₃N₅O = 827.27) 138 m / z = 919.14 (C₆₅H₃₇N₅S = 919.28) 24 m / z = 903.19 (C₆₅H₃₇N₅O = 903.30) 154 m / z = 919.12 (C₆₅H₃₇N₅S = 919.28) 42 m / z = 903.20 (C₆₅H₃₇N₅O = 903.30) 166 m / z = 919.13 (C₆₅H₃₇N₅S = 919.28) 43 m / z = 903.21 (C₆₅H₃₇N₅O = 903.30) 172 m / z = 919.14 (C₆₅H₃₇N₅S = 919.28) 53 m / z = 903.21 (C₆₅H₃₇N₅O = 903.30) 188 m / z = 813.05 (C₅₉H₃₅N₅ = 813.29) 54 m / z = 903.19 (C₆₅H₃₇N₅O = 903.30) 197 m / z = 827.07 (C₅₉H₃₃N₅O = 827.27) 70 m / z = 903.21 (C₆₅H₃₇N₅O = 903.30)
[0095] Material property testing:
[0096] The thermogravimetric temperature Td and glass transition temperature Tg of compounds 1, 4, 5, 10, 13, 14, 24, 42, 43, 53, 54, 70, 72, 80, 94, 108, 120, 126, 138, 154, 166, 172, 188, and 197 of this invention were tested, and the test results are shown in Table 3 below.
[0097] Note: The thermogravimetric temperature Td is the temperature at which 5% weight is lost in a nitrogen atmosphere, measured on a TGAN-1000 thermogravimetric analyzer at a nitrogen flow rate of 10 mL / min. The glass transition temperature Tg is measured by differential scanning calorimetry (DSC, Shinco DSCN-650) at a heating rate of 10 °C / min.
[0098] Table 3:
[0099]
[0100] The data above show that the compounds synthesized in this invention have excellent thermal stability, indicating that compounds conforming to the general structural formula of this invention all have excellent thermal stability and can meet the requirements for use in organic electroluminescent materials.
[0101] Device performance testing:
[0102] Application Example 1:
[0103] ITO was used as the anode substrate material for the reflective layer, and its surface was treated sequentially with water, acetone, and N2 ions.
[0104] A hole injection layer (HIL) is formed by depositing 10 nm of HT-1 doped with 3% wt NDP-9 on top of the ITO anode substrate.
[0105] A first hole transport layer (HTL) is formed by depositing 100 nm of HT-1 above the hole injection layer (HIL);
[0106] RP is vacuum-deposited over the first hole transport layer (HTL) to form a second hole transport layer (RPL) with a thickness of 30 nm;
[0107] Compound 1 and P-10 designed in this invention were co-deposited as red host materials in a mass ratio of 5:5. RD was deposited as a dopant material (the amount of RD was 8% of the total mass of compound 1 and P-10) on the second hole transport layer (RPL) to form a light-emitting layer with a thickness of 30 nm.
[0108] HB-1 was deposited onto the light-emitting layer to obtain a hole blocking layer (HBL) with a thickness of 20 nm;
[0109] ET-1 and LiQ were co-deposited onto the hole blocking layer (HBL) at a mass ratio of 5:5 to obtain an electron transport layer (ETL) with a thickness of 30 nm.
[0110] Magnesium (Mg) and silver (Ag) are mixed in a mass ratio of 9:1 and vapor-deposited onto the electron transport layer (ETL) to form an electron injection layer (EIL) with a thickness of 50 nm.
[0111] Subsequently, silver (Ag) is vapor-deposited onto the electron injection layer to form a cathode with a thickness of 100 nm. A 50 nm thick DNTPD is then deposited on the cathode sealing layer. Furthermore, the cathode surface is sealed with a UV-curable adhesive and a sealing cap containing a desiccant to protect the organic electroluminescent device from the influence of atmospheric oxygen or moisture. Thus, an organic electroluminescent device is prepared.
[0112]
[0113]
[0114] Application Example 2-25
[0115] Compounds 4, 5, 10, 13, 14, 24, 42, 43, 53, 54, 70, 72, 80, 94, 108, 120, 126, 138, 154, 166, 172, 188, and 197 from Examples 2-25 of the present invention were used as the main red light materials, with the other parts being the same as in Application Example 1. Based on this, organic electroluminescent devices of Application Examples 2-25 were fabricated.
[0116] Compare with Example 1-2:
[0117] The difference from Application Example 1 is that D1 in KR1020170116983A and D2 in CN114591328A are used to replace compound 1 as the main material for red light, respectively. Otherwise, they are the same as in Application Example 1.
[0118] The organic electroluminescent device manufactured in the above application example and the organic electroluminescent device manufactured in the comparative example have the characteristic of operating at a current density of 10 mA / cm². 2 The results were measured under the specified conditions and are shown in Table 4.
[0119] Table 4:
[0120]
[0121]
[0122] As shown in Table 4 above, when the compounds of the present invention are applied to organic electroluminescent devices, the luminous efficiency is significantly improved at the same current density, the device start-up voltage is reduced, the power consumption of the device is relatively reduced, and the lifespan of the device is correspondingly improved.
[0123] The organic electroluminescent devices prepared in Comparative Examples 1-2 and Application Examples 1-12 were subjected to luminescence lifetime tests to obtain the luminescence lifetime T97% data (the time for the luminous brightness to decrease to 97% of the initial brightness). The testing equipment was a TEO luminescent device lifetime testing system. The results are shown in Table 5:
[0124] Table 5:
[0125]
[0126]
[0127] As shown in Table 5 above, when the compounds of this invention are applied to organic electroluminescent devices, the service life is significantly improved at the same current density, indicating broad application prospects.
Claims
1. A compound containing a triazine structure, characterized in that, Its chemical structural formula is shown in Formula 2: ; in, Ar1 and Ar2 are substituted or unsubstituted groups of the following: aryl (C6-C18) or heteroaryl (C5-C24), wherein the substituent is selected from one or more of deuterium, fluorine, cyano, alkyl (C1-C6), deuterated alkyl (C1-C6), aryl (C6-C18), deuterated aryl (C6-C18), and heteroaryl (C5-C24); L1 and L2 are independently single bonds or substituted or unsubstituted phenyl, naphthyl, or biphenyl groups, respectively, with substituents selected from one or more of deuterium, fluorine, cyano, C6-C30 aryl, C6-C30 deuterated aryl, and C5-C30 heteroaryl.
2. The compound according to claim 1, characterized in that, Ar1 and Ar2 are substituted or unsubstituted groups of the following: phenyl, biphenyl, anthryl, dibenzofuranyl, dibenzothiophene, fluorenyl, phenanthryl, benzophenanthrenefuranyl, wherein the substituent is selected from one or more of deuterium, fluorine, cyano, C6-C12 aryl, C6-C12 deuterated aryl, and C5-C20 heteroaryl.
3. The compound according to claim 1, characterized in that, L1 and L2 are independently single bonds or substituted or unsubstituted phenyl, naphthyl, or biphenyl groups, with substituents selected from one or more of deuterium, fluorine, and cyano groups.
4. The compound according to claim 1, characterized in that, Ar1 and Ar2 are substituted or unsubstituted groups of the following: phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, wherein the substituent is selected from one or more of deuterium, phenyl, and biphenyl; L1 and L2 are, independently, single-bonded or substituted or unsubstituted phenyl or biphenyl groups.
5. The compound according to claim 1, characterized in that, The compound is any one of the following compounds: 。 6. An organic electroluminescent device, characterized in that, The device includes a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode. The organic layer comprises a hole injection layer, a first hole transport layer, a second hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. At least one of the hole injection layer, the first hole transport layer, the second hole transport layer, the light-emitting layer, the hole blocking layer, the electron transport layer, and the electron injection layer contains a compound as described in any one of claims 1-5.
7. The organic electroluminescent device as described in claim 6, characterized in that, The light-emitting layer contains a light-emitting host material, which is a mixture of one or more of the compounds according to any one of claims 1-5 and the following P-Type compounds, wherein the P-Type compounds are as follows: 。 8. An electronic display device, characterized in that, It contains the organic electroluminescent device as described in claim 6.
9. An OLED lighting device, characterized in that, It contains the organic electroluminescent device as described in claim 6.
Citation Information
Patent Citations
Carbazole derivative and application thereof
CN114591328A
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Hetero-cyclic compound and organic light emitting device using the same
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