Organic electroluminescent material composition and application thereof
By optimizing the structure of organic electroluminescent material compositions, the problem of carrier accumulation in OLED devices was solved, improving luminous efficiency and lifetime, reducing driving voltage, and achieving higher internal quantum efficiency.
Patent Information
- Application Number
- CN202511241700.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-09-01
- Publication Date
- 2025-11-18
AI Technical Summary
In existing OLED devices, charge carriers accumulate at the interface, resulting in low luminous efficiency, internal quantum efficiency failing to reach 100%, high driving voltage, and short lifetime.
Organic electroluminescent material compositions employing specific structures, including first and second luminescent materials, achieve synergistic effects by optimizing their structural combination to improve device performance.
This improved the luminous efficiency and lifetime of OLED devices, reduced the driving voltage, and achieved higher internal quantum efficiency.
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Figure CN120965689A_ABST
Abstract
Description
Technical Field
[0001] This invention relates to the field of luminescent materials, and more specifically to an organic electroluminescent material composition and its application in organic electroluminescent devices. Background Technology
[0002] Organic light-emitting diode (OLED) devices emit light in two forms: fluorescence and phosphorescence. Fluorescence is emitted using the energy of singlet excitons, while phosphorescence is emitted using the energy of both singlet and triplet excitons. Because the ratio of singlet to triplet excitons is fixed at 1:3, theoretically, the internal quantum efficiency of fluorescent devices using only singlet excitons is at most 25%, while the internal quantum efficiency of phosphorescent devices can reach 100%.
[0003] To fabricate OLED devices with lower driving voltages, better luminous efficiency, and longer lifetimes, and to continuously improve OLED device performance, innovation in OLED device structure and fabrication processes is necessary, along with ongoing research and innovation in functionalized organic materials used in OLED devices. Based on this, the OLED field has been committed to developing new organic electroluminescent materials to achieve devices with low driving voltages, high luminous efficiency, and superior lifetimes. In recent years, researchers in this field have made continuous attempts and explorations to improve luminous efficiency and stability, with many seeking new materials to enhance device performance. While these efforts have yielded some improvements, the problem of excessive carrier accumulation at the interface and relatively low luminous efficiency remain.
[0004] Therefore, there is an urgent need in this field to develop organic electroluminescent devices with higher performance. Further development of organic electroluminescent materials that can provide better photoelectric performance, especially the host material of the light-emitting layer, is the direction that the industry is constantly striving to break through. Summary of the Invention
[0005] The purpose of this invention is to provide an organic electroluminescent material composition as the main material for organic electroluminescent devices, thereby preparing organic electroluminescent devices with higher luminous efficiency.
[0006] To achieve the above objectives, the present invention adopts the following technical solution:
[0007] In a first aspect, the present invention provides an organic electroluminescent material composition comprising a combination of a first luminescent material and a second luminescent material, wherein the first luminescent material has a structure as shown in Formula I:
[0008]
[0009] In formula I, R I1 RI2 Each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
[0010] a is any integer from 0 to 5;
[0011] Ar1, Ar2, Ar3, and Ar4 are each independently selected from any one of substituted or unsubstituted C6-C60 aryl groups or substituted or unsubstituted C3-C60 heteroaryl groups;
[0012] The second luminescent material has a structure as shown in Formula II:
[0013]
[0014] In Equation II, b is selected from any integer from 1 to 4;
[0015] A is selected from any one of methyl, deuterated methyl, trifluoromethyl, fluorine atom, and cyano group;
[0016] L is selected from any one of single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene;
[0017] Ar5 and Ar6 are each independently selected from any one of substituted or unsubstituted C6-C60 aryl groups and substituted or unsubstituted C3-C60 heteroaryl groups;
[0018] R I1 R I2 The substituents in Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, and L are each independently selected from deuterium, halogen, cyano, nitro, hydroxyl, ester, amino, C1-C30 alkyl, C1-C30 alkoxy, C1-C30 alkylsilyl, C1-C30 alkylamino, C3-C30 cycloalkyl, C2-C30 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aryloxy, C3-C60 heteroaryloxy, C6-C60 arylthio, C3-C60 heteroarylthio, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C60 arylsilyl, and C3-C60 heteroarylsilyl; R I1 R I2 In Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, and L, the substituents are either independently not connected to adjacent groups or are linked to form a ring through chemical bonds.
[0019] In this invention, 'a' represents the substituent R. I2 The number of R's, 'a' can be 0, 1, 2, 3, 4, or 5; when a is greater than or equal to 2, there are more (e.g., 2, 3, 4, or 5) R's. I2 These can be the same or different groups.
[0020] In this invention, b represents the number of substituents A, and b can be 1, 2, 3 or 4; when b is greater than or equal to 2, the multiple (e.g. 2, 3 or 4) A are the same or different groups.
[0021] In this invention, when L is selected as a single bond, it means that the N atom in the fused ring is directly connected to the triazine via a single bond.
[0022] In this invention, "each substituent is independently not connected to an adjacent group" means that the substituent is only connected to the C atom via a single bond; "each substituent is independently connected to an adjacent group via a chemical bond to form a ring" means that the substituent, in addition to being connected to the C atom via a chemical bond, is also connected to an adjacent group via a chemical bond, thereby forming a fused ring structure. The same descriptions will have the same meaning in the following text and will not be repeated individually.
[0023] In this invention, the "substituted or unsubstituted" group can replace one substituent or multiple substituents. When there are multiple substituents (at least two), they can be the same or different substituents. The same expression used below has the same meaning.
[0024] It should be noted that, for ease of explanation, the possible effects of each group / feature have been described separately in this invention, but this does not mean that these groups / features act in isolation. In fact, the essential reason for obtaining good performance is the optimized combination of the entire molecular structure, the result of the synergistic effect between various groups, rather than the effect of a single group / feature.
[0025] The following are preferred embodiments of the present invention, but are not intended to limit the embodiments provided by the present invention. The objectives and beneficial effects of the present invention can be better achieved and realized through the following preferred embodiments.
[0026] As a preferred embodiment, the first luminescent material has any one or a combination of at least two of the structures shown in any of Formulas I-1 to I-8:
[0027]
[0028] In equations I-1 to I-8, R I1 R I2 Ar1, Ar2, Ar3, and Ar4 have the same limited range as Equation I.
[0029] As a preferred implementation scheme, R I1 Selected from any one of substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryl groups and substituted or unsubstituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl groups.
[0030] The R I1 The substituents in the middle are each independently selected from deuterium, halogens (e.g., F, Cl, Br, I), cyano, amino, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, and C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, or a combination of at least two of them.
[0031] Preferably, the R I1 It is selected from any one of substituted or unsubstituted C6-C18 aryl groups and substituted or unsubstituted C3-C18 heteroaryl groups; more preferably, it is selected from any one of the following groups: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, quinolinyl, isoquinolinyl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl.
[0032] Optionally, the R I1 The substituents in the middle are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, amino, C1-C6 alkyl, C4-C8 cycloalkyl, C6-C18 aryl, and C3-C18 heteroaryl; more preferably selected from any one or a combination of at least two of deuterium, halogen, cyano, amino, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, pyridyl, indolyl, benzofuranyl, dibenzofuranyl, benzothiophene, and dibenzothiophene.
[0033] Specifically, the substituents after the two combinations can include, for example, deuterated alkyl groups formed by combining alkyl and deuterium (e.g., deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, etc.); haloalkyl groups formed by combining halogen and alkyl groups (e.g., trifluoromethyl, etc.); and deuterated aryl groups formed by combining aryl and deuterium (e.g., deuterated phenyl). Deuterated naphthyl (etc.); alkyl-substituted aryl groups (e.g., tert-butylphenyl, etc.) or aryl-substituted alkyl groups (e.g., phenyl-substituted tert-butyl, etc.) formed by combinations of alkyl and aryl groups, etc. When the same description is used below, it has the same meaning and will not be repeated individually.
[0034] More preferably, the R I1 It is selected from any one of phenyl, deuterated phenyl, biphenyl, terphenyl, naphthyl, deuterated naphthyl, anthraceneyl, and phenanthrene.
[0035] As a preferred implementation scheme, R I2 Each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, substituted or unsubstituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl.
[0036] Optionally, the R I2 The substituents in the middle are each independently selected from deuterium, halogens (e.g., F, Cl, Br, I), cyano, amino, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, and C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, or a combination of at least two of them.
[0037] Preferably, the R I2Each group is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C4-C8 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl; more preferably selected from hydrogen, deuterium, halogen, cyano, or any one of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, quinolinyl, isoquinolinyl, furanyl, benzofuranyl, dibenzofuranyl, thiophene, benzothiophene, dibenzothiophene.
[0038] Optionally, the R I2 The substituents in the middle are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, amino, C1-C6 alkyl, C4-C8 cycloalkyl, C6-C18 aryl, and C3-C18 heteroaryl; more preferably selected from any one or a combination of at least two of deuterium, halogen, cyano, amino, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, pyridyl, indolyl, benzofuranyl, dibenzofuranyl, benzothiophene, and dibenzothiophene.
[0039] More preferably, the R I2 Each is independently selected from any one of hydrogen, deuterium, methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, deuterated tert-butyl, tert-pentyl, neopentyl, phenyl, deuterated phenyl, biphenyl, naphthyl, and deuterated naphthyl; for example, selected from any one of hydrogen, deuterium, phenyl, deuterated phenyl, naphthyl, and deuterated naphthyl.
[0040] Preferably, a is selected from 0, 1, or 5.
[0041] Preferably, when a is selected from 5, the R I2 Selected from hydrogen or deuterium.
[0042] As a preferred embodiment, Ar1, Ar2, Ar3, and Ar4 are each independently selected from any one of substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryl groups and substituted or unsubstituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl groups.
[0043] Optionally, the substituents in Ar1, Ar2, Ar3, and Ar4 are each independently selected from deuterium, halogens (e.g., F, Cl, Br, I), cyano, amino, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, and C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C2... Any one or a combination of at least two of the following: aryl (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28); heteroaryl (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28); and arylamino (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28).
[0044] Preferably, Ar1, Ar2, Ar3, and Ar4 are each independently selected from any of the following groups, whether substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, binaphthyl, phenanthryl, anthracene, triphenylene, pyrene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, pyridyl, quinolinyl, isoquinolinyl, furanyl, benzofuranyl, dibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, and N-phenylcarbazoyl.
[0045] Optionally, the substituents in Ar1, Ar2, Ar3, and Ar4 are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, amino, C1-C6 alkyl, C4-C8 cycloalkyl, C6-C18 aryl, C3-C18 heteroaryl, and C6-C18 arylamino; more preferably, they are selected from any one or a combination of at least two of deuterium, halogen, cyano, amino, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, pyridyl, indolyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, carbazole, and diphenylamino.
[0046] More preferably, Ar1, Ar2, Ar3, and Ar4 are each independently selected from any of the following groups, where * represents the linkage site of the group:
[0047]
[0048] As a preferred embodiment, the first luminescent material is selected from any one or a combination of at least two of the following compounds A1-A141:
[0049]
[0050]
[0051]
[0052]
[0053]
[0054]
[0055]
[0056]
[0057]
[0058]
[0059] As a preferred embodiment, the second luminescent material has a structure as shown in Formula II-1 and / or Formula II-2:
[0060]
[0061] In Equations II-1 and II-2, Ar5, Ar6, A, and L have the same range of limitation as in Equation II.
[0062] As a preferred embodiment, Ar5 and Ar6 are each independently selected from any one of substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryl groups and substituted or unsubstituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl groups.
[0063] Optionally, the substituents in Ar5 and Ar6 are each independently selected from deuterium, halogens (e.g., F, Cl, Br, I), cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, and C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, or a combination of at least two of these.
[0064] Preferably, Ar5 and Ar6 are each independently selected from any of the following groups, whether substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, binaphthyl, phenanthryl, anthraceneyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, dibenzofuranyl, dibenzothiopheneyl.
[0065] Optionally, the substituents in Ar5 and Ar6 are each independently selected from any one or a combination of at least two of the following: deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, and naphthyl.
[0066] More preferably, Ar5 and Ar6 are each independently selected from any of the following groups: Indicates the linkage site of the functional group:
[0067]
[0068]
[0069] As a preferred embodiment, L is selected from any one of single-bonded, substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) arylene, and substituted or unsubstituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) heteroarylene.
[0070] Optionally, the substituents in L are each independently selected from deuterium, halogens (e.g., F, Cl, Br, I), cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, and C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, or a combination of at least two of these.
[0071] Preferably, L is selected from a single bond or any of the following groups, where * indicates the linkage site of the group:
[0072]
[0073] As a preferred embodiment, the second luminescent material is selected from any one or a combination of at least two of the following compounds B1-B177:
[0074]
[0075]
[0076]
[0077]
[0078]
[0079]
[0080]
[0081]
[0082]
[0083] As a preferred embodiment, the first luminescent material includes any one of the compounds with the structure shown in any one of Formula I-1, Formula I-2, Formula I-3, Formula I-4, Formula I-5, Formula I-6, Formula I-7, and Formula I-8, and is more preferably any one of compounds A1-A141.
[0084] As a preferred embodiment, the second luminescent material comprises any one of the compounds with the structure shown in any one of Formula II-1 and Formula II-2, and is more preferably any one of compounds B1-B177.
[0085] As a preferred embodiment, the mass ratio of the first luminescent material to the second luminescent material is 1:(0.01-99); for example, it can be 1:0.05, 1:0.1, 1:0.3, 1:0.5, 1:0.7, 1:1, 1:1.5, 1:2, 1:2.5, 1:3, 1:3.5, 1:4, 1:4.5, 1:5, 1:5.5, 1:6, 1:6.5, 1:7, 1:7.5, 1:8, 1:8.5, 1:9, 1:9.5, 1:10, 1:15, 1:20, 1:30, 1:40, 1:50, 1:60, 1:70, 1:80, 1:90 or any value between them.
[0086] Preferably, the mass ratio of the first luminescent material to the second luminescent material is 1:(0.1-9), more preferably 1:(0.4-2.5), even more preferably 1:(0.6-1.5), and even more preferably 1:(0.9-1.1).
[0087] In a second aspect, the present invention provides an application of the organic electroluminescent material composition as described in the first aspect, wherein the organic electroluminescent material composition is applied to an organic electronic device.
[0088] Preferably, the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin-film transistor, an organic field-effect transistor, an organic thin-film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner, or electronic paper.
[0089] Preferably, the organic electroluminescent material composition is used in an organic electroluminescent device.
[0090] Preferably, the organic electroluminescent material composition is used as a light-emitting layer material in an organic electroluminescent device.
[0091] Preferably, the organic electroluminescent material composition serves as the host material of the light-emitting layer in an organic electroluminescent device.
[0092] Of course, the application of the organic electroluminescent material composition is not limited to the main material of the light-emitting layer. In some technical solutions, it can also be used as a hole blocking material, an electron blocking material, etc.; preferably, it is used as the main material of the light-emitting layer.
[0093] More preferably, the organic electroluminescent material composition serves as the red light host material of the light-emitting layer in an organic electroluminescent device.
[0094] As a preferred embodiment, a combination of at least one of the first luminescent materials A1 to A141 and at least one of the second luminescent materials B1 to B177 of the first aspect of the present invention can be used in the organic electroluminescent device as described in the second aspect.
[0095] Thirdly, the present invention provides a light-emitting layer for an organic electroluminescent device, comprising a host material and a dopant (also known as a dye, luminescent dye, guest material, etc.), wherein the host material comprises the organic electroluminescent material composition as described in the first aspect.
[0096] In a preferred embodiment, the dopant is at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant is not particularly limited, but is preferably a metallized complex compound selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably a neighboring metallized complex compound selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably a neighboring iridium metallized complex compound.
[0097] As a preferred embodiment, the dopant has a structure as shown in Formula III:
[0098]
[0099] In Equation III, P is selected from the structure shown in Equation P1 or Equation P2:
[0100]
[0101] Where m is selected from 1, 2, or 3;
[0102] R 100 To R 107 R 201 To R 207 R 301 To R 308 Each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; the adjacent R 100 To R 107 They are not connected to each other or are linked in a ring by chemical bonds; adjacent R 201 To R 207 They are not connected to each other or are linked in a ring by chemical bonds; adjacent R 301 To R 308 They are either not connected to each other or linked together by chemical bonds to form a ring;
[0103] The R 100 To R 107 R 201 To R 207 R 301 To R 308 The substituents in the middle are each independently selected from deuterium, halogen, cyano,
[0104] The group consisting of any one or at least two of the following: nitro, hydroxyl, ester, amino, C1-C30 alkyl, C1-C30 alkoxy, C1-C30 alkylsilyl, C1-C30 alkylamino, C3-C30 cycloalkyl, C2-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylthio, C3-C30 heteroarylthio, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 arylsilyl, and C3-C30 heteroarylsilyl.
[0105] Preferably, the R 100 To R 107 R 201 To R 207 R 301 To R 308 Each is independently selected from hydrogen, deuterium, halogen (e.g., F, Cl, Br, I), cyano, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, substituted or unsubstituted C3-C10 (e.g.,
[0106] Any one of the following: cycloalkyl groups (C4, C5, C6, C7, C8, C9, etc.), substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryl groups, and substituted or unsubstituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl groups.
[0107] Optionally, the R 100 To R 107 R 201 To R 207 R 301 To R 308The substituents in the middle are each independently selected from deuterium, halogens (e.g., F, Cl, Br, I), cyano, amino, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, and C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, or a combination of at least two of them.
[0108] Preferably, R 100 R 101 R 102 R 103 R 104 R 105 R 106 R 107 Each of the following groups is independently selected from hydrogen, deuterium, halogen, or substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, cyclopentyl, cyclohexyl, phenyl.
[0109] Optionally, the R 100 R 101 R 102 R 103 R 104 R 105 R 106 R 107 The substituents in the middle are each independently selected from any one of deuterium, halogen, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, and deuterated phenyl.
[0110] Preferably, the adjacent R 100 R 101 R 102 R 103 The rings are either not connected to each other or are connected by chemical bonds to form a pyridine ring on the parent nucleus to form a ring Cy1, wherein the ring Cy1 is selected from any of the following ring structures, substituted or unsubstituted: quinoline ring, isoquinoline ring, benzofuranopyridine ring, benzothiophenopyridine ring, indenepyridine ring, benzofuranoquinoline ring, benzothiophenoquinoline ring, and indenequinoline ring.
[0111] Preferably, the adjacent R 104 R 105 R 106 R 107 The rings are either not connected to each other or are connected by chemical bonds to form a ring Cy2 with the benzene ring on the parent nucleus, wherein the ring Cy2 is selected from any of the following ring structures, substituted or unsubstituted: naphthalene ring, fluorene ring, dibenzothiophene ring, dibenzofuran ring, indenepyridine ring, benzofuran-pyridine ring, benzothiophene-pyridine ring.
[0112] Optionally, the substituents in the ring Cy1 and ring Cy2 are each independently selected from any one of deuterium, halogen, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, and deuterated phenyl.
[0113] Preferably, R 201 R 202 R 203 R 204 R 205 R 206 R 207 Each of the following groups is independently selected from hydrogen, deuterium, halogen, or substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, cyclopentyl, cyclohexyl, phenyl.
[0114] Optionally, the R 201 R 202 R 203 R 204 R 205 R 206 R 207 The substituents in the middle are each independently selected from any one of deuterium, halogen, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, and deuterated phenyl.
[0115] Preferably, R 301 R 302 R 303 R 304 R 305 R 306 R 307 R 308Each of the following groups is independently selected from hydrogen, deuterium, halogen, or substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, cyclopentyl, cyclohexyl, phenyl.
[0116] Optionally, the R 301 R 302 R 303 R 304 R 305 R 306 R 307 R 308 The substituents in the middle are each independently selected from any one of deuterium, halogen, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, and deuterated phenyl.
[0117] Preferably, the adjacent R 301 R 302 R 303 R 304 The rings are either not connected to each other or are connected by chemical bonds to form a ring Cy3 with the benzene ring on the parent nucleus, wherein the ring Cy3 is selected from any of the following ring structures, substituted or unsubstituted: naphthalene ring, fluorene ring, dibenzothiophene ring, dibenzofuran ring, indenepyridine ring, benzofuran-pyridine ring, benzothiophene-pyridine ring.
[0118] Preferably, the adjacent R 305 R 306 R 307 R 308 The rings are either not connected to each other or are connected by chemical bonds to form a pyridine ring on the parent nucleus to form a cyclic Cy4, wherein the cyclic Cy4 is selected from any of the following substituted or unsubstituted ring structures: quinoline ring, isoquinoline ring, benzofuranopyridine ring, benzothiophenopyridine ring, indenepyridine ring, benzofuranoquinoline ring, benzothiophenoquinoline ring, and indenequinoline ring.
[0119] Optionally, the substituents in the cyclic Cy3 and cyclic Cy4 are each independently selected from any one of deuterium, halogen, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, and deuterated phenyl.
[0120] As a preferred embodiment, the dopant is selected from one or more of the following structures, but is not limited thereto:
[0121]
[0122]
[0123] As a preferred embodiment, the dopant comprises 1%-20% by mass of 100% of the organic electroluminescent material composition, for example, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19% or any value between them, preferably 1%-10%, more preferably 2%-8%.
[0124] Fourthly, the present invention provides an organic electroluminescent device, the organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, the organic layer comprising the organic electroluminescent material composition as described in the first aspect.
[0125] Preferably, the organic layer includes a light-emitting layer, which comprises an organic electroluminescent material composition as described in the first aspect.
[0126] Preferably, the thickness of the light-emitting layer is 10-60nm, for example, it can be 12nm, 15nm, 18nm, 20nm, 22nm, 25nm, 28nm, 30nm, 32nm, 35nm, 38nm, 40nm, 42nm, 45nm, 48nm, 50nm, 52nm, 55nm, 58nm or any value between them, and more preferably 20-50nm.
[0127] Preferably, based on the mass of the organic electroluminescent material composition as 100%, the mass percentage of the first luminescent material to the second luminescent material is 1%:99% to 99%:1% (for example, it can be 2%:98%, 3%:97%, 4%:96%, 5%:95%, 10%:90%, 20%:80%, 30%:70%, 40%:60%, 45%:55%, 50%:50%, 55%:45%, 60%:40%, 70%:30%, 80%:20%, 90%:10%, 95%:5%, 98%:2%, or any value between them), preferably 10%:90% to 90%:10%, more preferably 30%:70% to 70%:30%, and even more preferably in the range of 40%:60% to 60%:40%.
[0128] Preferably, the organic layer further includes a hole transport region and an electron transport region.
[0129] Preferably, the hole transport region includes any one or a combination of at least two of the following: a hole injection layer, a hole transport layer, and an electron blocking layer. The hole transport region may also include a hole auxiliary layer.
[0130] Preferably, the electron transport region includes any one or a combination of at least two of the following: an electron injection layer, an electron transport layer, and a hole blocking layer. The electron transport region may also include an electron buffer layer.
[0131] In a preferred embodiment, the organic electroluminescent device includes a first electrode and a second electrode, and an organic layer located between the electrodes. The organic layer may be further divided into multiple regions, such as a hole transport region, a light-emitting layer (which may also include a light-emitting auxiliary layer), and an electron transport region; the light-emitting layer comprises the organic electroluminescent material composition as described in the first aspect.
[0132] In a preferred embodiment, the organic electroluminescent device includes a first electrode (anode), an organic layer, and a second electrode (cathode) sequentially disposed therefrom; the organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer sequentially disposed therefrom, wherein the hole injection layer is in contact with the first electrode. The organic layer (preferably the light-emitting layer) comprises the organic electroluminescent material composition as described in the first aspect.
[0133] In a preferred embodiment, the light-emitting layer is a layer that emits light, and can be a single layer or a multilayer consisting of two or more layers stacked together. Simultaneously, the light-emitting layer can comprise multiple host materials, including the organic electroluminescent material composition, wherein the organic electroluminescent material composition can be contained simultaneously in one light-emitting layer or separately in different light-emitting layers.
[0134] As a preferred embodiment, at least one of the following is selected from amine-based compounds: hole injection material, hole transport material, hole assist material, luminescent material (which may also include luminescent assist material), and electron blocking material.
[0135] As a preferred embodiment, at least one of the electron transport material, electron injection material, electron buffer material, and hole blocking material is selected from azazine-based compounds.
[0136] As a preferred embodiment, each layer of the organic electroluminescent device of the present invention can be obtained using dry film formation methods, such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film formation methods, such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating and flow coating methods.
[0137] When a solvent is used in a wet film formation method, a thin film can be formed by dissolving or diffusing the materials forming the layers into any suitable solvent (such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent can be any solvent in which the materials forming the layers can be dissolved or diffused and in which there are no problems with film-forming capability.
[0138] As a preferred embodiment, the first luminescent material represented by Formula I and the second luminescent material represented by Formula II can be film-formed using the methods listed above, typically by co-evaporation or hybrid evaporation. Co-evaporation is a hybrid deposition method in which two or more materials are placed in respective individual crucible sources and current is simultaneously applied to two chambers to evaporate the materials. Hybrid evaporation is a hybrid deposition method in which two or more materials are mixed in a crucible source before evaporation and current is applied to a chamber to evaporate the materials.
[0139] Fifthly, the present invention provides a display device or lighting device, including the organic electroluminescent device as described in the fourth aspect.
[0140] This invention can provide a display system or lighting system by incorporating a variety of host materials. Furthermore, it is possible to produce display devices or lighting devices using the organic electroluminescent device of this invention.
[0141] In some implementations, the display device is a display device for smartphones, tablets, laptops, PCs, TVs, or automobiles.
[0142] In some implementations, the lighting device is an outdoor or indoor lighting device.
[0143] The present invention has the following beneficial effects: the organic electroluminescent material composition provided by the present invention can be used to prepare organic electroluminescent devices with higher luminous efficiency. Furthermore, organic electroluminescent devices comprising the organic electroluminescent material composition provided by the present invention also have advantages in terms of lifetime characteristics. Detailed Implementation
[0144] The invention will now be described in detail. However, the following description is intended to explain the invention and is not intended to limit the scope of the invention in any way.
[0145] definition
[0146] In the present invention, the term "organic electroluminescent material" means a material that can be used in an organic electroluminescent device and can contain at least one compound. If necessary, the organic electroluminescent material can be included in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole assisting material, a light emission assisting material, an electron blocking material, a light emitting material (including a host material and a dopant), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, and the like.
[0147] In the present invention, the term "multiple organic electroluminescent materials" means an organic electroluminescent material that is a combination of at least two compounds and can be included in any layer constituting the organic electroluminescent device. It can mean both the material before being included in the organic electroluminescent device (e.g., before vapor deposition) and the material after being included in the organic electroluminescent device (e.g., after vapor deposition). For example, the multiple organic electroluminescent materials can be a combination of at least two compounds, and the at least two compounds can be included in at least one of the hole injection layer, the hole transport layer, the hole assisting layer, the light emission assisting layer, the electron blocking layer, the light emitting layer, the electron buffer layer, the hole blocking layer, the electron transport layer, and the electron injection layer. At least two compounds can be included in the same layer or different layers by methods used in the art (e.g., they can be co-evaporated or co-evaporated, or can be evaporated separately).
[0148] In the present invention, the term "multiple host materials" means an organic electroluminescent material that is a combination of at least two host materials. It can mean both the material before being included in the organic electroluminescent device (e.g., before vapor deposition) and the material after being included in the organic electroluminescent device (e.g., after vapor deposition). The multiple host materials of the present invention can be included in any light emitting layer constituting the organic electroluminescent device. At least two compounds included in the multiple host materials can be included in one light emitting layer simultaneously, or can be included in different light emitting layers separately. If at least two host materials are included in one layer, for example, they can be co-evaporated to form a layer, or can be co-evaporated simultaneously separately to form a layer.
[0149] In the present invention, the halogens can each be fluorine, chlorine, bromine or iodine.
[0150] In the present invention, for the expression of chemical elements, unless otherwise specified, the concept of isotopes with the same chemical properties is included. For example, hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C, 13 C, etc.
[0151] In this invention, unless otherwise specified, the heteroatom of the heteroaryl group is selected from N, O, S, P, B, Si, or Se, preferably N, O, or S. The heteroatom of the heterocycloalkyl group is selected from N, O, S, P, B, Si, or Se, preferably N, O, or S.
[0152] In this invention, the way the ring structure is represented by "—" indicates that the connection point is located at any position on the ring structure where bonding can occur.
[0153] In this invention, Both "*" and "" indicate the linking site of a functional group.
[0154] In this invention, "each independently" means that when there are multiple subjects, they can be the same or different from each other.
[0155] In this invention, the expression Ca-Cb represents that the group has ab carbon atoms. Unless otherwise specified, the number of carbon atoms does not include the number of carbon atoms of the substituents.
[0156] In this invention, C1-C30 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, or C29, etc.
[0157] In this invention, C3-C30 can all be C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28 or C29, etc.
[0158] In this invention, C2-C30 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28 or C29, etc.
[0159] In this invention, C6-C60 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, or C58, etc.
[0160] In this invention, C3-C60 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, or C58, etc.
[0161] In this invention, unless otherwise specified, the C6-C60 aryl (C6-C60 aromatic ring), preferably C6-C30 aryl (C6-C30 aromatic ring), includes monocyclic aryl and fused-ring aryl; the monocyclic aryl means that the group contains at least one phenyl group, and when it contains at least two phenyl groups, the phenyl groups are linked by single bonds, exemplarily including but not limited to: phenyl, biphenyl, terphenyl, tetraphenyl, etc.; the fused-ring aryl means that the group contains at least two rings (and at least one ring is an aromatic ring), and the rings share two adjacent carbon atoms. Mutually fused groups, exemplary including but not limited to: naphthyl, anthraceneyl, phenanthryl, indene, fluorenyl and their derivatives (9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9-dinaphthylfluorenyl, spirodifluorenyl, benzo[a]fluorenyl (benzo[A]fluorenyl, benzo[B]fluorenyl, benzo[C]fluorenyl), fluoranyl, triphenylene, pyrene, perylene, Aryl, tetraphenyl, acenaphthenyl, benzo[a]acenaphthenyl, etc. It should be noted that monocyclic aryl and fused-ring aryl groups linked by single bonds also fall under the category of aryl groups, such as phenylnaphthyl, naphthylphenyl, and binaphthyl.
[0162] In this invention, unless otherwise specified, the C3-C60 heteroaryl group (C3-C60 heteroaryl ring), preferably the C3-C30 heteroaryl group (C3-C30 heteroaryl ring), includes monocyclic heteroaryl groups or fused-ring heteroaryl groups. A monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, etc.), the heteroaryl group and other groups are connected by a single bond, exemplarily including but not limited to: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiophene, pyrroleyl, bipyridinyl, phenylpyridinyl, pyridylphenyl, etc. The term "fused-ring heteroaryl" refers to a molecule containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring), wherein the two share two adjacent atoms fused together in a group. Examples include, but are not limited to: quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, isobenzothiopheneyl, indolyl, dibenzofuranyl, benzonaphthofuranyl (benzo[B]naphtho[2,3-D]furanyl, benzo[B]naphtho[1,2-D) Furanyl, benzo[B]naphtho[2,1-D]furanyl), dibenzothiophene, benzo[B]naphtho[2,3-D]thiophene (benzo[B]naphtho[1,2-D]thiophene, benzo[B]naphtho[2,1-D]thiophene), carbazole and its derivatives (N-phenylcarbazole, N-naphthylcarbazole, benzocarbazole, dibenzocarbazole, indolecarbazole, azacarbazole, etc.), acridineyl, phenothiazinyl, phenotoxazinyl, hydrogenated acridineyl, etc.
[0163] In this invention, a specific example of the C6-C60 arylene can be a divalent group obtained by removing one hydrogen atom from the above-mentioned aryl examples; a specific example of the C3-C60 heteroarylene can be a divalent group obtained by removing one hydrogen atom from the above-mentioned heteroaryl examples.
[0164] In this invention, a specific example of the C6-C60 arylamino group (preferably C6-C30 arylamino group) is a monovalent group obtained by substituting at least one hydrogen atom in -NH2 with the aforementioned aryl group. A specific example of the C3-C60 heteroarylamino group (preferably C3-C30 heteroarylamino group) is a monovalent group obtained by substituting at least one hydrogen atom in -NH2 with the aforementioned heteroaryl group.
[0165] In this invention, the C6-C60 aryloxy group (preferably C6-C30 aryloxy group) is a monovalent group formed by attaching an aryl group to an oxygen group, as exemplified above. The C3-C60 heteroaryloxy group (preferably C3-C30 heteroaryloxy group) is a monovalent group formed by attaching an heteroaryl group to an oxygen group, as exemplified above. The C6-C60 arylthio group (preferably C6-C30 arylthio group) is a monovalent group formed by attaching an aryl group to an oxygen group, as exemplified above. The C3-C60 heteroarylthio group (preferably C3-C30 heteroarylthio group) is a monovalent group formed by attaching an heteroaryl group to an oxygen group, as exemplified above.
[0166] In this invention, a specific example of the C6-C60 arylsilyl group (preferably C6-C30 arylsilyl group) is a monovalent group obtained by replacing at least one hydrogen in -SiH3 with the above-mentioned aryl group, and a specific example of the C3-C60 heteroarylsilyl group (preferably C3-C30 heteroarylsilyl group) is a monovalent group obtained by replacing at least one hydrogen in -SiH3 with the above-mentioned heteroaryl group.
[0167] In this invention, the C1-C30 alkyl group, preferably C1-C16 alkyl group, and more preferably C1-C10 alkyl group, includes straight-chain alkyl or branched-chain alkyl groups, and exemplary includes, but is not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, etc.
[0168] In this invention, specific examples of the C1-C30 alkoxy group can be exemplified by the monovalent group obtained by attaching the aforementioned alkyl group to O. Specific examples of the C1-C30 alkylsilyl group are monovalent groups obtained by replacing at least one hydrogen atom in -SiH3 with the aforementioned alkyl group; specific examples of the C1-C30 alkylamino group are monovalent groups obtained by replacing at least one hydrogen atom in -NH2 with the aforementioned alkyl group.
[0169] In this invention, the C3-C30 cycloalkyl group, preferably C3-C10 cycloalkyl group, includes monocycloalkyl or polycycloalkyl groups. Monocycloalkyl refers to an alkyl group containing a single ring structure, while polycycloalkyl refers to a structure formed by two or more cycloalkyl groups sharing one or more carbon atoms on a ring. Exemplary examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.
[0170] In this invention, specific examples of the C2-C30 heterocyclic alkyl group can be exemplified by groups formed by replacing at least one C atom in the aforementioned cycloalkyl group with a heteroatom (e.g., N, O, S, etc.), including but not limited to: epoxy group, oxetane, tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyrroleyl, tetrahydropyranyl, piperidinyl, piperazineyl, dioxaneyl, morpholinyl, etc.
[0171] In this invention, the C2-C30 alkenyl group, preferably C2-C10 alkenyl group, contains at least one C=C, and includes, but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.
[0172] In this invention, "combination" means that one or more members of the applicable list are combined to form an arrangement known or chemically stable that can be conceived by a person skilled in the art from the applicable list. For example, combinations of alkyl and deuterium to form partially or fully deuterated alkyl groups (e.g., deuterated methyl, deuterated ethyl, deuterated tert-butyl, etc.); combinations of halogen and alkyl groups to form partially or fully haloalkyl groups (e.g., trifluoromethyl, etc.); or combinations of halogen, alkyl, and aryl groups to form haloarylalkyl groups, etc.
[0173] The technical solution of the present invention will be further described below. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be considered as specific limitations thereof.
[0174] The first luminescent material represented by Formula I and the second luminescent material represented by Formula II according to the present invention can be prepared by synthesis methods known to those skilled in the art, requiring only the replacement of the corresponding raw materials. For example, reference can be made to the disclosures in prior art such as CN111718341B, CN114292261B, and CN110337432B, but the invention is not limited thereto.
[0175] For example, the synthesis route of the second luminescent material represented by Formula II is exemplified as follows:
[0176] The definitions of A, b, L, Ar5, and Ar6 are the same as those in Formula II, and X is Cl or Br.
[0177] In the above process, the synthesis of intermediates S1 and S2 both follow the conventional Suzuki reaction. The entire synthesis process can be found by referring to...
[0178] CN114292261B and CN110337432B are prepared by a similar method, which only requires replacing the raw materials. The details will not be elaborated here. Alternatively, those skilled in the art can also prepare them using other methods in the prior art.
[0179] The luminous efficiency characteristics of the organic electroluminescent device according to the present invention will be explained below. However, the following embodiments only describe the characteristics of the organic electroluminescent device according to the present invention in detail, and the present invention is not limited to the following embodiments.
[0180] The specific preparation process is as follows:
[0181] The structure of the organic electroluminescent device of the present invention is as follows: ITO / HI (10nm) / HT01 (60nm) / EB (5nm) / first luminescent material: second luminescent material: D-17 (48%:48%:4%) (40nm) / HB (10nm) / ET01:LiQ (1:1) (30nm) / LiQ (1nm) / Al.
[0182] The molecular structures of each functional layer material are as follows:
[0183]
[0184] Example 1:
[0185] (1) The glass substrate coated with ITO transparent conductive layer was ultrasonically treated in commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in acetone:ethanol mixed solvent (1:1, v / v), baked in a clean environment until the moisture was completely removed, cleaned with ultraviolet light and ozone, and bombarded with low-energy cation beam.
[0186] (2) Place the glass substrate with the anode into a vacuum chamber and evacuate it to 1×10⁻⁶. -5 ~9×10 -3 Pa, compound HI was vacuum-deposited on the above-mentioned anolyte film as a hole injection layer at a deposition rate of 0.1 nm / s and a total film thickness of 10 nm; then compound HT01 was vacuum-deposited as a hole transport layer at a deposition rate of 0.1 nm / s and a total film thickness of 60 nm; then compound EB was vacuum-deposited as an electron blocking layer at a deposition rate of 0.1 nm / s and a total film thickness of 5 nm.
[0187] (3) An electron blocking layer (EML) is vacuum-deposited on top of the electron blocking layer as a light-emitting layer. The EML consists of a mixture of a first light-emitting material A1, a second light-emitting material B1, and a dopant D-17. The mass percentages of A1, B1, and D-17 are 48%:48%:4%. The first and second light-emitting materials are co-evaporated to form the light-emitting layer. The evaporation rate is 0.1 nm / s, and the total film thickness is 40 nm. Then, compound HB is vacuum-deposited as a hole blocking layer. The evaporation rate is 0.1 nm / s, and the total film thickness is 10 nm.
[0188] (4) A mixture of compound ET01:LiQ (1:1, w / w) was vacuum-deposited on top of the hole blocking layer as an electron transport layer. The deposition rate was 0.1 nm / s and the total film thickness was 30 nm.
[0189] (5) A 1 nm thick LiQ layer was sequentially vacuum-deposited on the electron transport layer as an electron injection layer, and a 150 nm thick Al layer was deposited as a cathode. After encapsulation, the organic electroluminescent device of Example 1 was obtained.
[0190] Examples 2-14, Comparative Examples 1-3:
[0191] An organic electroluminescent device, which differs from Example 1 only in that the organic electroluminescent material composition (the main material of the light-emitting layer) is replaced with the compound in Table 1. The other structures, materials and preparation methods of the device are the same as those in Example 1. In Table 1, "mass percentage" represents the mass ratio of the first light-emitting material to the second light-emitting material, and "--" indicates that the compound was not added or the mass percentage does not exist.
[0192] The second luminescent material in the comparative example is shown below:
[0193]
[0194] Performance testing:
[0195] At the same brightness of 5000 cd / m 2 The voltage (V) and luminous efficacy (cd / A) of the organic electroluminescent device were tested using a digital source meter and a luminance meter. The test values of voltage and luminous efficacy of Comparative Example 1 were recorded as 1.00. The voltage and luminous efficacy of other embodiments and comparative examples are the ratios of their respective test values to the test values of Comparative Example 1 (i.e., relative voltage and relative luminous efficacy). The test results are shown in Table 1.
[0196] Table 1
[0197] Device Number First luminescent material Second luminescent material mass percentage relative voltage relative luminous efficiency Example 1 A1 B1 50%:50% 0.91 1.29 Example 2 A8 B97 50%:50% 0.93 1.20 Example 3 A19 B162 50%:50% 0.91 1.27 Example 4 A48 B108 50%:50% 0.93 1.13 Example 5 A65 B56 50%:50% 0.92 1.09 Example 6 A77 B63 50%:50% 0.93 1.26 Example 7 A94 B86 50%:50% 0.94 1.11 Example 8 A102 B78 50%:50% 0.93 1.17 Example 9 A118 B51 50%:50% 0.95 1.06 Example 10 A126 B27 50%:50% 0.90 1.30 Example 11 A1 B1 40%:60% 0.91 1.25 Example 12 A1 B1 60%:40% 0.89 1.21 Example 13 A94 B86 40%:60% 0.96 1.13 Example 14 A94 B86 60%:40% 0.98 1.09 Comparative Example 1 A1 Ref-1 50%:50% 1.00 1.00 Comparative Example 2 A1 -- -- 1.11 0.78 Comparative Example 3 -- B1 -- 1.07 0.89
[0198] As can be seen from Table 1, the good hole mobility of the first luminescent material matches the good electron mobility of the second luminescent material, thereby achieving a balance of charge carriers. The electroluminescent material composition formed by these materials, when used as the main material in organic electroluminescent devices, can effectively improve the luminous efficiency of the devices, reduce the voltage, and endow the devices with better overall performance.
[0199] Although the present invention has been described in detail above with general descriptions, specific embodiments, and experiments, it is not intended to limit the scope of the invention, as will be obvious to those skilled in the art. Therefore, any modifications or improvements made without departing from the spirit of the invention are within the scope of protection claimed by the present invention.
Claims
1. An organic electroluminescent material composition comprising a combination of a first luminescent material and a second luminescent material, wherein, The first luminescent material has a structure as shown in Formula I: In formula I, R I1 R I2 Each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; a is any integer from 0 to 5; Ar1, Ar2, Ar3, and Ar4 are each independently selected from any one of substituted or unsubstituted C6-C60 aryl groups or substituted or unsubstituted C3-C60 heteroaryl groups; The second luminescent material has a structure as shown in Formula II: In Equation II, b is selected from any integer from 1 to 4; A is selected from any one of methyl, deuterated methyl, trifluoromethyl, fluorine atom, and cyano group; L is selected from any one of single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene; Ar5 and Ar6 are each independently selected from any one of substituted or unsubstituted C6-C60 aryl groups and substituted or unsubstituted C3-C60 heteroaryl groups; R I1 R I2 The substituents in Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, and L are each independently selected from deuterium, halogen, cyano, nitro, hydroxyl, ester, amino, C1-C30 alkyl, C1-C30 alkoxy, C1-C30 alkylsilyl, C1-C30 alkylamino, C3-C30 cycloalkyl, C2-C30 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C6-C60 aryloxy, C3-C60 heteroaryloxy, C6-C60 arylthio, C3-C60 heteroarylthio, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C60 arylsilyl, and C3-C60 heteroarylsilyl; R I1 R I2 In Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, and L, the substituents are either independently not connected to adjacent groups or are linked to form a ring through chemical bonds.
2. The organic electroluminescent material composition according to claim 1, characterized in that, The first luminescent material has any one or a combination of at least two of the structures shown in any of Formulas I-1 to I-8: In equations I-1 to I-8, R I1 R I2 Ar1, Ar2, Ar3, and Ar4 have the same limiting range as Equation I; Preferably, R I1 Selected from any one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups; Preferably, the R I1 The substituents in the middle are each independently selected from any one or a combination of at least two of the following: deuterium, halogen, cyano, amino, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, the R I1 It is selected from any one of substituted or unsubstituted C6-C18 aryl groups and substituted or unsubstituted C3-C18 heteroaryl groups; more preferably, it is selected from any one of the following groups: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, quinolinyl, isoquinolinyl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl; Optionally, the R I1 The substituents in the middle are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, amino, C1-C6 alkyl, C4-C8 cycloalkyl, C6-C18 aryl, and C3-C18 heteroaryl; more preferably selected from any one or a combination of at least two of deuterium, halogen, cyano, amino, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, pyridyl, indolyl, benzofuranyl, dibenzofuranyl, benzothiophene, and dibenzothiophene. More preferably, the R I1 It is selected from any one of phenyl, deuterated phenyl, biphenyl, terphenyl, naphthyl, deuterated naphthyl, anthraceneyl, and phenanthrene; And / or, R I2 Each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; Optionally, the R I2 The substituents in the middle are each independently selected from any one or a combination of at least two of the following: deuterium, halogen, cyano, amino, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, the R I2 Each group is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C4-C8 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl; more preferably selected from hydrogen, deuterium, halogen, cyano, or any one of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, quinolinyl, isoquinolinyl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl; Optionally, the R I2 The substituents in the middle are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, amino, C1-C6 alkyl, C4-C8 cycloalkyl, C6-C18 aryl, and C3-C18 heteroaryl; more preferably selected from any one or a combination of at least two of deuterium, halogen, cyano, amino, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, pyridyl, indolyl, benzofuranyl, dibenzofuranyl, benzothiophene, and dibenzothiophene. More preferably, the R I2 Each is independently selected from any one of hydrogen, deuterium, methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, deuterated tert-butyl, tert-pentyl, neopentyl, phenyl, deuterated phenyl, biphenyl, naphthyl, and deuterated naphthyl; further selected from any one of hydrogen, deuterium, phenyl, deuterated phenyl, naphthyl, and deuterated naphthyl; Preferably, 'a' is selected from 0, 1, or 5; And / or, Ar1, Ar2, Ar3, and Ar4 are each independently selected from any one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups; Optionally, the substituents in Ar1, Ar2, Ar3, and Ar4 are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, amino, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, and C6-C30 arylamino. Preferably, Ar1, Ar2, Ar3, and Ar4 are each independently selected from any of the following groups, whether substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, binaphthyl, phenanthryl, anthracene, triphenylene, pyrene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, pyridyl, quinolinyl, isoquinolinyl, furanyl, benzofuranyl, dibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, N-phenylcarbazoyl; Optionally, the substituents in Ar1, Ar2, Ar3, and Ar4 are each independently selected from deuterium, halogen, cyano, amino, C1-C6 alkyl, C4-C8 cycloalkyl, C6-C18 aryl, C3-C18 heteroaryl, and C6-C18 arylamino, or a combination of at least two of these groups; more preferably, they are selected from deuterium, halogen, cyano, amino, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, pyridyl, indolyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, carbazole, and diphenylamino, or a combination of at least two of these groups. More preferably, Ar1, Ar2, Ar3, and Ar4 are each independently selected from any of the following groups, where * represents the linkage site of the group:
3. The organic electroluminescent material composition according to claim 1 or 2, characterized in that, The first luminescent material is selected from any one or a combination of at least two of the following compounds A1-A141:
4. The organic electroluminescent material composition according to any one of claims 1-3, characterized in that, The second luminescent material has a structure as shown in Formula II-1 and / or Formula II-2: In Equations II-1 and II-2, Ar5, Ar6, A, and L have the same defined range as in Equation II; Preferably, Ar5 and Ar6 are each independently selected from any one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups; Optionally, the substituents in Ar5 and Ar6 are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, Ar5 and Ar6 are each independently selected from any of the following groups, whether substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, binaphthyl, phenanthryl, anthraceneyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, dibenzofuranyl, dibenzothiopheneyl; Optionally, the substituents in Ar5 and Ar6 are each independently selected from any one or a combination of at least two of the following: deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, and naphthyl. More preferably, Ar5 and Ar6 are each independently selected from any of the following groups, -- indicating the linkage site of the group: Preferably, L is selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, and substituted or unsubstituted C3-C30 heteroarylene; Optionally, the substituents in L are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. More preferably, L is selected from a single bond or any of the following groups, where * indicates the linkage site of the group:
5. The organic electroluminescent material composition according to any one of claims 1-4, characterized in that, The second luminescent material is selected from any one or a combination of at least two of the following compounds B1-B177:
6. The organic electroluminescent material composition according to any one of claims 1-5, characterized in that, The first luminescent material includes any one of the compounds with the structure shown in any one of Formula I-1, Formula I-2, Formula I-3, Formula I-4, Formula I-5, Formula I-6, Formula I-7, and Formula I-8, and is more preferably any one of compounds A1-A141; Preferably, the second luminescent material comprises any one of the compounds with the structure shown in any one of Formula II-1 and Formula II-2, and more preferably any one of compounds B1-B177; Preferably, the mass ratio of the first luminescent material to the second luminescent material is 1:(0.01-99); Preferably, the mass ratio of the first luminescent material to the second luminescent material is 1:(0.1-9), more preferably 1:(0.4-2.5), even more preferably 1:(0.6-1.5), and even more preferably 1:(0.9-1.1).
7. The application of an organic electroluminescent material composition as described in any one of claims 1-6, preferably, the organic electroluminescent material composition is applied to an organic electronic device; Preferably, the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin-film transistor, an organic field-effect transistor, an organic thin-film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner, or electronic paper; Preferably, the organic electroluminescent material composition is used in an organic electroluminescent device; Preferably, the organic electroluminescent material composition serves as the light-emitting layer material in an organic electroluminescent device; Preferably, the organic electroluminescent material composition serves as the host material of the light-emitting layer in an organic electroluminescent device; More preferably, the organic electroluminescent material composition serves as the red light host material of the light-emitting layer in an organic electroluminescent device.
8. A light-emitting layer of an organic electroluminescent device, comprising a host material and a dopant, wherein the host material comprises an organic electroluminescent material composition as described in any one of claims 1-6; Preferably, the dopant is at least one phosphorescent dopant or fluorescent dopant, preferably a phosphorescent dopant; more preferably a metallization complex compound selected from iridium, osmium, copper and platinum, more preferably an ortho-metallization complex compound selected from iridium, osmium, copper and platinum, and even more preferably an ortho-metallization iridium complex compound; Preferably, the dopant has a structure as shown in Formula III: In Equation III, P is selected from the structure shown in Equation P1 or Equation P2: in, m is selected from 1, 2, or 3; R 100 To R 107 R 201 To R 207 R 301 To R 308 Each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; the adjacent R 100 To R 107 They are not connected to each other or are linked in a ring by chemical bonds; adjacent R 201 To R 207 They are not connected to each other or are linked in a ring by chemical bonds; adjacent R 301 To R 308 They are either not connected to each other or linked together by chemical bonds to form a ring; The R 100 To R 107 R 201 To R 207 R 301 To R 308 The substituents in the middle are each independently selected from any one or a combination of at least two of the following: deuterium, halogen, cyano, nitro, hydroxyl, ester, amino, C1-C30 alkyl, C1-C30 alkoxy, C1-C30 alkylsilyl, C1-C30 alkylamino, C3-C30 cycloalkyl, C2-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylthio, C3-C30 heteroarylthio, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 arylsilyl, and C3-C30 heteroarylsilyl. Preferably, the R 100 To R 107 R 201 To R 207 R 301 To R 308 Each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; Optionally, the R 100 To R 107 R 201 To R 207 R 301 To R 308 The substituents in the middle are each independently selected from any one or a combination of at least two of the following: deuterium, halogen, cyano, amino, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, R 100 R 101 R 102 R 103 R 104 R 105 R 106 R 107 Each of the following groups, independently selected from hydrogen, deuterium, halogen, or substituted or unsubstituted, consists of: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, cyclopentyl, cyclohexyl, and phenyl. Optionally, the R 100 R 101 R 102 R 103 R 104 R 105 R 106 R 107 The substituents in the middle are each independently selected from any one of deuterium, halogen, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, and deuterated phenyl; Preferably, the adjacent R 100 R 101 R 102 R 103 They are either not connected to each other or are linked by chemical bonds to form a ring with the pyridine ring on the parent nucleus. Preferably, the adjacent R 104 R 105 R 106 R 107 They are either not connected to each other or are linked by chemical bonds to form a ring with the benzene ring on the parent nucleus; Preferably, R 201 R 202 R 203 R 204 R 205 R 206 R 207 Each of the following groups, independently selected from hydrogen, deuterium, halogen, or substituted or unsubstituted, consists of: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, cyclopentyl, cyclohexyl, and phenyl. Optionally, the R 201 R 202 R 203 R 204 R 205 R 206 R 207 The substituents in the middle are each independently selected from any one of deuterium, halogen, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, and deuterated phenyl; Preferably, R 301 R 302 R 303 R 304 R 305 R 306 R 307 R 308 Each of the following groups, independently selected from hydrogen, deuterium, halogen, or substituted or unsubstituted, consists of: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, cyclopentyl, cyclohexyl, and phenyl. Optionally, the R 301 R 302 R 303 R 304 R 305 R 306 R 307 R 308 The substituents in the middle are each independently selected from any one of deuterium, halogen, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, phenyl, and deuterated phenyl; Preferably, the adjacent R 301 R 302 R 303 R 304 They are either not connected to each other or are linked by chemical bonds to form a ring with the benzene ring on the parent nucleus; Preferably, the adjacent R 305 R 306 R 307 R 308 They are either not connected to each other or are linked by chemical bonds to form a ring with the pyridine ring on the parent nucleus; Preferably, the dopant is selected from one or more of the following structures: Preferably, based on the mass of the organic electroluminescent material composition as 100%, the mass of the dopant is 1%-20%, more preferably 1%-10%, and more preferably 2%-8%.
9. An organic electroluminescent device, the organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, the organic layer comprising an organic electroluminescent material composition as described in any one of claims 1-7; Preferably, the organic layer includes a light-emitting layer, which comprises an organic electroluminescent material composition as described in any one of claims 1-7; Preferably, the thickness of the light-emitting layer is 10-60 nm, more preferably 20-50 nm; Preferably, the organic layer further includes a hole transport region and an electron transport region; Preferably, the hole transport region includes any one or a combination of at least two of the following: a hole injection layer, a hole transport layer, and an electron blocking layer; Preferably, the electron transport region includes any one or a combination of at least two of the electron injection layer, electron transport layer, and hole blocking layer.
10. A display device or lighting device, comprising the organic electroluminescent device as described in claim 9.
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