Boron-nitrogen-containing fused ring organic compound and use thereof, organic electroluminescent device, display device
By designing organic compounds with boron and nitrogen multiple resonance structure and specific anthracene-containing groups, the problem of existing fluorescent materials being difficult to meet narrow spectrum, high efficiency and long life at the same time, achieving high efficiency, long life and low cost production of OLED devices.
Patent Information
- Application Number
- PCT/CN2024/117221
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-09-03
- Filing Date
- 2024-09-05
- Publication Date
- 2025-03-20
AI Technical Summary
Existing fluorescent materials are difficult to meet the performance requirements of narrow spectrum, high efficiency and long life at the same time, and the high cost of phosphorescent materials limits the widespread application of OLED devices.
An organic compound with a boron-nitrogen multi-resonance structure and a specific anthracene-containing group was designed. By introducing a structure with a low triplet energy level, its HOMO and LUMO energy levels are adjusted, the triplet energy level is reduced and the thermal stability is improved.
Excellent electroluminescent performance, narrow spectral characteristics and thermal stability are achieved, effectively improving the luminescence efficiency and life of the device, improving the color purity and reducing costs.
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Figure CN2024117221_20032025_PF_FP_ABST
Abstract
Description
Boron-nitrogen fused ring organic compounds and their applications, organic electroluminescent devices, and display devices Technical Field
[0001] The present disclosure belongs to the technical field of organic electroluminescent materials, and particularly relates to an organic compound and applications thereof. Background Art
[0002] Electroluminescent devices based on organic materials (such as organic light-emitting diodes, OLEDs) are becoming increasingly popular. Compared with electroluminescent devices based on inorganic materials, the inherent flexibility of organic materials makes them very suitable for manufacturing flexible and thin electroluminescent devices. Beautiful and cool screens, displays and lighting equipment can be designed and produced according to demand, which has incomparable advantages over inorganic materials. At present, screens and displays based on OLEDs have good efficiency and lifespan, but OLED devices with long life, high efficiency and high color purity are still difficult to develop. At the same time, display technology faces higher commercial requirements, such as meeting the BT-2020 color gamut standard for image signals in the 4K and 8K eras. The CIEy of green light is 0.797, which significantly increases the color gamut coverage. At present, the use of luminescent materials with narrow half-width emission spectra is one of the important means to achieve high light color purity. In particular, in currently commercialized OLED materials, green light luminescent materials mainly use phosphorescent materials with wide half-width and strong shoulder peaks at long wavelengths, which makes it difficult to meet the requirements of high efficiency and excellent color purity at the same time.
[0003] In recent years, scientists have developed thermally activated delayed fluorescence (TADF) materials that have both 100% theoretical exciton utilization and a narrow emission spectrum. Using them as OLED light-emitting materials is expected to achieve the high color purity requirements of BT-2020 and ensure high efficiency. However, this type of material has a serious efficiency roll-off at high brightness, and the device life is short, far from meeting the standards for mass production and use. To solve this problem, scientists have proposed a superfluorescence strategy, which is to transfer the excited state energy of the TADF material or phosphorescent material to the narrow spectrum fluorescent material through energy transfer to emit light, thereby achieving a theoretical 100% exciton utilization rate and a narrow emission spectrum, and is expected to obtain OLED devices with good efficiency, long life and high color purity. However, the existing fluorescent materials are difficult to meet the performance requirements of narrow spectrum, high efficiency and life at the same time. In addition, phosphorescent materials are usually based on transition metal elements, such as iridium, platinum, etc., and because their abundance is usually low, phosphorescent materials are very expensive among many OLED materials. Therefore, reducing the amount of phosphorescent materials is very critical to reducing the cost of OLEDs.
[0004] Therefore, developing more types of organic narrow-spectrum luminescent materials with better electroluminescent properties is one of the key issues to achieve the above expectations and is the research focus in this field.
[0005] Summary of the Invention
[0006] In response to the shortcomings of the prior art, the purpose of the present disclosure is to provide an organic compound and its application. Through its special molecular structure, the organic compound has excellent electroluminescent properties, narrow spectral characteristics and thermal stability. It is used in organic electroluminescent devices and is suitable as a doping material for the light-emitting layer. It can effectively improve the luminous efficiency and life of the device and improve the color purity.
[0007] To achieve this goal, the present disclosure adopts the following technical solutions:
[0008] In a first aspect, the present disclosure provides an organic compound having a structure as shown in Formula I:
[0009] In Formula I, X 1 、X 2 、X 3 、X 4 Each independently selected from CR A1 or N; multiple (e.g. 2, 3, 4) CRs A1 R in A1 are the same or different groups.
[0010] In Formula I, Y 1 、Y 2 、Y 3 、Y 4 Each independently selected from CR A2 or N; multiple (e.g. 2, 3, 4) CRs A2 R in A2 are the same or different groups.
[0011] In Formula I, Z 1 、Z 2 、Z 3 Each independently selected from CR A3 or N; multiple (e.g. 2, 3) CRs A3 R in A3 are the same or different groups.
[0012] R A1 、R A2 、R A3Each is independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.
[0013] Any two adjacent R A1 , any two adjacent R A2 , any two adjacent R A3 At least one group of the rings is connected by a chemical bond to form a ring F, wherein the ring F is selected from any one of a substituted or unsubstituted C6-C60 aromatic ring and a substituted or unsubstituted C3-C60 heteroaromatic ring; the ring F and the ring shown in Formula I are fused to each other.
[0014] It should be noted that in this disclosure, “any two adjacent R A1 , any two adjacent R A2 , any two adjacent R A3 " preferably refers to any two adjacent groups located in the same six-membered ring.
[0015] The R A1 、R A2 、R A3 In the above formula (1), the other groups except those forming ring F are each independently not connected to the adjacent ring structure or are connected to form a ring through a chemical bond.
[0016] In formula I, Ar1 and Ar2 are each independently selected from unsubstituted or R B Substituted C6-C60 aryl, unsubstituted or R B Any one of the substituted C3-C60 heteroaryl groups; Ar1 and Ar2 are each independently not connected to the adjacent ring structure or are connected to form a ring through a chemical bond.
[0017] In the present disclosure, “Ar1 is not connected to the adjacent ring structure” means that Ar1 is only connected to the N atom through a single bond; “Ar1 is connected to the adjacent ring structure through a chemical bond to form a ring” means that Ar1 is not only connected to the N atom through a chemical bond, but also to the adjacent ring (e.g., X 4 The ring where Ar2 is located is connected by a chemical bond to form a fused ring structure; the relevant description of Ar2 is similar. When the same description is involved below, it has the same meaning and will not be repeated one by one.
[0018] R B R is independently selected from any one of halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; B Each is independently not connected to the adjacent ring structure or connected to form a ring through a chemical bond.
[0019] R A1 、R A2 、R A3 , Ring F, R B The substituents substituted in the above-mentioned group are each independently selected from halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C6-C30 arylsilyl, unsubstituted or R'substituted C1-C20 alkylamino, cyano , nitro, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl; the substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring by chemical bonds.
[0020] In this disclosure, the term "substituted or unsubstituted" may be substituted with one or more substituents. When there are multiple (at least two) substituents, they may be the same or different. The same expressions used below have the same meaning. Unless otherwise specified, the range of substituents is as described above and will not be repeated here.
[0021] The R A1 、R A2 、R A3 At least one of the groups is R X , and / or, the R BAt least one of the groups is R X .
[0022] It should be noted that in the organic compounds disclosed herein, the fused ring structure is connected to at least one R X , the R X Can be connected to X 1 、X 2 、X 3 、X 4 、Y 1 、Y 2 、Y 3 、Y 4 、Z 1 、Z 2 、Z 3 It can be located on the C atom in Ar1 or Ar2, or it can be connected to the C atom in Ar1 or Ar2 as a substituent in Ar1 or Ar2.
[0023] The R X It has the structure shown in formula a:
[0024] In formula a, —* represents the attachment site of the group.
[0025] In formula a, L is selected from any one of a substituted or unsubstituted C6-C60 arylene group and a substituted or unsubstituted C3-C60 heteroarylene group.
[0026] In formula a, X 11 、X 12 、X 13 、X 18 、X 19 、X 20 Each independently selected from C, CR C1 or N, one of which is C, and the C is connected to L.
[0027] In formula a, X 14 、X 15 、X 16 、X 17 Each independently selected from CR C1 Or any one of N.
[0028] R C1Each is independently selected from any one of hydrogen, halogen, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl.
[0029] The substituents substituted in L are each independently selected from any one of halogen, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl.
[0030] R' is independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or a combination of at least two thereof; adjacent R's are not connected or are connected to form a ring by chemical bonds; the R' is not connected to adjacent ring structures or is connected to form a ring by chemical bonds.
[0031] In this disclosure, the "unsubstituted or R'-substituted" group may be substituted with a single substituent R' or with multiple substituents R'. When there are multiple (at least two) substituents R', they may be the same or different. The same expressions used below have the same meaning. Unless otherwise specified, the range of R' is as described above and will not be repeated here.
[0032] The molecular structure of the organic compound provided by the present disclosure is shown in Formula I, wherein the parent core structure contains a boron nitrogen multiple resonance (BN MR) structure and has good thermally activated delayed fluorescence (TADF) characteristics; in the BN multiple resonance structure, an anthracene group R containing a specific structure with a low triplet energy level is introduced. X , so that the anthracene-containing group R X The HOMO energy level of the anthracene group R is lower than the HOMO energy level of the BN multiple resonance structure it replaces, and higher than the HOMO-1 energy level of the BN multiple resonance structure. X The LUMO energy level of the BN MR TADF material is higher than that of the material it replaces. The BN MR obtained can keep the transition of the lowest singlet state controlled by the mother core of the BN multiple resonance structure, that is, the transition of the lowest singlet state is the transition from the HOMO to the LUMO of the boron nitrogen multiple resonance mother core structure, and the lowest triplet state transition occurs in the anthracene group R X Therefore, the organic compound not only maintains the advantages of narrow spectrum and high efficiency of BN MR materials, but also reduces the triplet energy level, eliminates the long-life delayed fluorescence property of the parent core of BN MR materials, and thus improves the efficiency roll-off and life attenuation caused by the high triplet energy level and slow reverse intersystem crossing of the boron nitrogen multiple resonance material, greatly reducing the transient life of the material in electroluminescence, which is beneficial to improve the life of the device. X The bridging group L introduced in the can adjust the vacuum evaporation temperature of the organic compound, which is beneficial to the improvement of thermal stability. X The mutual combination of the groups plays a role in lowering the triplet energy level and adjusting the light color, so that the organic compound has excellent electroluminescent properties, narrow spectral characteristics and excellent thermal stability. It is used as a fluorescent doping material for the light-emitting layer, which is beneficial to improving the device efficiency roll-off, enhancing the luminous efficiency and extending the device life, and obtaining high color purity.
[0033] It should be noted that, while the potential effects of various groups / features are described separately in this disclosure for ease of explanation, this does not imply that these groups / features function in isolation. In fact, the fundamental reason for achieving good performance is the optimized combination of the entire molecular structure and the result of the synergistic effects of the various groups, rather than the effects of a single group / feature.
[0034] The following are preferred technical solutions of the present disclosure, but are not intended to limit the technical solutions provided by the present disclosure. The following preferred technical solutions can better achieve and realize the objectives and beneficial effects of the present disclosure. It should be emphasized that a preferred implementation is merely an optional embodiment of the present invention, focusing on achieving certain single technical effect indicators in certain situations, and does not mean that it is superior to other embodiments.
[0035] In the present disclosure, the halogen may be fluorine, chlorine, bromine or iodine. The same descriptions below all have the same meanings.
[0036] In this disclosure, unless otherwise specified, the expression of chemical elements includes the concept of isotopes with the same chemical properties. For example, hydrogen (H) includes 1 H (hydrogen), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C. 13 C, etc.
[0037] In the present disclosure, hydrogen at any position on the organic compound of the structure represented by Formula I may be optionally replaced by deuterium.
[0038] In the present disclosure, 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.
[0039] In the present disclosure, the expression of a ring structure crossed by “—” indicates that the connection site is any position on the ring structure that can form a bond.
[0040] In the present disclosure, "——*" and "*" both represent the attachment site of a group.
[0041] In the present disclosure, the expression Ca-Cb represents that the number of carbon atoms in the group is ab. Unless otherwise specified, the number of carbon atoms does not include the number of carbon atoms in the substituent.
[0042] In the present disclosure, “each independently” means that when there are multiple subjects, they may be the same or different.
[0043] In the present disclosure, the C1-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.
[0044] The C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.
[0045] The C2-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.
[0046] The C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.
[0047] The C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.
[0048] The C6-C60 can all 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.
[0049] The 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.
[0050] The C5-C60 can all be 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.
[0051] In the present disclosure, the C1-C20 straight chain or branched chain alkyl group, preferably a C1-C16 straight chain or branched chain alkyl group, further preferably a C1-C10 straight chain or branched chain alkyl group, illustratively includes but is not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, 2-methylbutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, neohexyl, 2-ethylhexyl, n-octyl, n-heptyl, n-nonyl, n-decyl, etc.
[0052] Specific examples of the C1-C20 alkoxy group include monovalent groups obtained by connecting the above-mentioned linear or branched alkyl groups to O.
[0053] A specific example of the C1-C20 alkylsilyl group is a monovalent group in which at least one hydrogen in -SiH3 is replaced by the above-mentioned straight-chain or branched alkyl group; a specific example of the C1-C20 alkylamino group is a monovalent group in which at least one hydrogen in -NH2 is replaced by the above-mentioned straight-chain or branched alkyl group.
[0054] The C3-C20 cycloalkyl group, preferably a C3-C10 cycloalkyl group, includes a monocyclic alkyl group or a polycyclic alkyl group. A monocyclic alkyl group refers to an alkyl group containing a single cyclic structure, and a polycyclic alkyl group refers to a structure composed of two or more cycloalkyl groups sharing one or more ring carbon atoms. Examples thereof include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl groups.
[0055] The C2-C20 alkenyl group, preferably a C2-C10 alkenyl group, contains at least one C=C, and illustratively includes but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.
[0056] In the present disclosure, the C6-C60 aryl group, preferably a C6-C30 aryl group, further preferably a C6-C20 aryl group, includes a monocyclic aryl group and a condensed ring aryl group; the monocyclic aryl group means that the group contains at least one phenyl group, and when it contains at least two phenyl groups, the phenyl groups are connected by a single bond, illustratively including but not limited to: phenyl, biphenyl, terphenyl, quaterphenyl, etc.; the condensed ring aryl group means that the group contains at least two aromatic rings, and the aromatic rings share a The groups in which two adjacent carbon atoms are fused to each other include, but are not limited to, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives (9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirobifluorenyl, benzofluorenyl, etc.), fluoranthenyl, triphenylene, pyrenyl, perylene, It should be noted that monocyclic aromatic groups and condensed aromatic groups connected by a single bond also fall within the scope of aromatic groups, such as phenylnaphthyl, naphthylphenyl, naphthylnaphthyl, phenylnaphthylphenyl, etc.
[0057] The C3-C60 heteroaryl group, preferably a C6-C30 heteroaryl group, further preferably a C3-C20 heteroaryl group, includes a monocyclic heteroaryl group or a condensed ring heteroaryl group. The monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains a heteroaryl group and other groups (such as aryl, heteroaryl, etc.), the heteroaryl group and the other group are connected by a single bond, illustratively including but not limited to: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, bipyridyl, phenylpyridyl, pyridylphenyl, etc. The fused ring heteroaryl group refers to a group containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring) in the molecule, and the two share two adjacent atoms fused to each other, including but not limited to: quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, isobenzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl and its derivatives (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, azacarbazolyl, etc.), acridinyl, phenothiazinyl, phenoxazinyl, hydroacridinyl, etc. It should be noted that heteroaryl and heteroaryl groups connected by a single bond, and aryl and heteroaryl groups connected by a single bond also fall within the scope of heteroaryl groups, such as phenylpyridinyl, phenylpyrimidinyl, diphenylpyridinyl, diphenylpyrimidinyl, etc.
[0058] In the present disclosure, the C6-C30 aryloxy group is a monovalent group formed by connecting the above-mentioned aryl groups with O, and the C3-C30 heteroaryloxy group is a monovalent group formed by connecting the above-mentioned heteroaryl groups with O.
[0059] In the present disclosure, specific examples of the C6-C30 arylamino group are monovalent groups in which at least one hydrogen in -NH2 is replaced by the above-mentioned aryl group, including but not limited to phenylamino, methylphenylamino, naphthylamino, anthrylamino, phenanthrenylamino, biphenylamino, etc. Specific examples of the C3-C30 heteroarylamino group are monovalent groups in which at least one hydrogen in -NH2 is replaced by the above-mentioned heteroaryl group, including but not limited to pyridylamino, pyrimidinylamino, dibenzofuranylamino, etc.
[0060] A specific example of the C6-C30 arylsilyl group is a monovalent group in which at least one hydrogen in -SiH3 is replaced by the above-mentioned aryl group.
[0061] Preferably, Ar1 is Thus, the organic compound has a structure as shown in Formula IA:
[0062] Among them, X 5 、X 6 、X 7 、X8 、X 9 Each independently selected from CR A4 or N; multiple (e.g. 2, 3, 4, 5) CRs A4 R in A4 are the same or different groups.
[0063] R A4 With R A1 Same range, R A4 Each is independently not connected to the adjacent ring structure or connected to form a ring through a chemical bond.
[0064] More preferably, the X 9 CR A4 , X 9 R in A4 The adjacent ring structures are connected to form a ring through a single bond.
[0065] Preferably, the organic compound has a structure as shown in Formula II:
[0066] In Formula II, X 1 、X 2 、X 3 、Y 1 、Y 2 、Y 3 、Y 4 、Z 1 、Z 2 、Z 3 , Ar2 have the same defined ranges as in formula I.
[0067] In Formula II, X 5 、X 6 、X 7 、X 8 Each independently selected from CR A4 or N; multiple (e.g. 2, 3, 4) CRs A4 R in A4 are the same or different groups.
[0068] R A4Each is independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; two adjacent R A4 They are not connected or connected to form a ring through chemical bonds; R A4 Each is independently not connected to the adjacent ring structure or connected to form a ring through a chemical bond.
[0069] The hydrogen at any position on the organic compound of the structure represented by formula II may be optionally replaced by deuterium.
[0070] Preferably, any two adjacent R A1 , any two adjacent R A2 , any two adjacent R A3 , any two adjacent R A4 At least one group of them is connected by a chemical bond to form a ring F, and the ring F has a structure as shown in formula b:
[0071] In formula b, the dotted line represents a fused bond.
[0072] In formula b, Q1, Q2, Q3, and Q4 are each independently selected from CR D1 or N; multiple (e.g. 2, 3, 4) CRs D1 R in D1 are the same or different groups.
[0073] R D1R is independently selected from any one of hydrogen, halogen, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; R D1 Each is independently not connected to the adjacent ring structure or connected to form a ring through a chemical bond.
[0074] In formula b, M1 and M2 are each independently selected from a single bond, O, S, Se, NAr m1 , CR m1 R m2 or SiR m3 R m4 any one of M1 and M2; at most one of M1 and M2 is a single bond. When one of M1 and M2 is a single bond, the ring F shown in formula b can be understood as a structure in which a six-membered ring (e.g., a benzene ring) is fused with a five-membered ring (e.g., a pyrrole ring, a furan ring, a thiophene ring, or a cyclopentadiene structure); when neither M1 nor M2 is a single bond, the ring F shown in formula b can be understood as a structure in which two six-membered rings are fused.
[0075] Ar m1 Any one selected from an unsubstituted or R'-substituted C6-C60 aryl group and an unsubstituted or R'-substituted C3-C60 heteroaryl group.
[0076] R m1 、R m2 、R m3 、R m4 Each is independently selected from any one of hydrogen, halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, unsubstituted or R'substituted C6-C60 aryl, and unsubstituted or R'substituted C3-C60 heteroaryl; the R m1 With R m2 are not connected or are connected to form a ring through chemical bonds; the R m3 With R m42 They are not connected or connected to form a ring through chemical bonds.
[0077] Preferably, the M1 is selected from O, S, NAr m1 or CR m1 R m2 Any one of: said M2 is a single bond, thus, said ring F is
[0078] Preferably, any two adjacent R A1 , any two adjacent R A2 , any two adjacent R A3 , any two adjacent R A4 Up to four groups in are connected by chemical bonds to form ring F;
[0079] Preferably, any two adjacent R A1 , any two adjacent R A4 A group of R is connected by a chemical bond to form a ring F; and / or, any two adjacent R A2 One group of them is connected by chemical bonds to form ring F;
[0080] Preferably, any two adjacent R A1 , any two adjacent R A2 , any two adjacent R A3 , any two adjacent R A4 A group of them is connected by chemical bonds to form ring F.
[0081] Preferably, the organic compound has a structure as shown in any one of Formula III-1 to Formula III-14:
[0082] Wherein, M1 is selected from O, S, NAr m1 or CR m1 R m2 Any one of .
[0083] Q1, Q2, Q3, Q4, Ar m1 、R m1 、R m2 Having the same limited range as in formula b;
[0084] X 1 、X 2 、X 3 、X 5 、X 6 、X 7 、X 8 、Y 1 、Y 2 、Y 3 、Y 4 、Z 1 、Z2 、Z 3 , Ar2 have the same defined ranges as in Formula II.
[0085] It should be noted that hydrogen at any position on the organic compound having a structure represented by any one of Formulas III-1 to III-14 may be optionally replaced by deuterium.
[0086] Preferably, the organic compound has a structure as shown in any one of Formula III-1, Formula III-2, Formula III-3, Formula III-4, Formula III-7, Formula III-12, Formula III-13, and Formula III-14, and further preferably has a structure as shown in any one of Formula III-1, Formula III-2, and Formula III-3.
[0087] Preferably, Ar2 is ——* represents the connection site of the group, Y 5 、Y 6 、Y 7 、Y 8 、Y 9 Each independently selected from CR A5 or N; R A5 With R A1 Same range, R A5 Each is independently not connected to the adjacent ring structure or connected to form a ring through a chemical bond.
[0088] Preferably, the organic compound has a structure as shown in Formula IB:
[0089] More preferably, the Y 9 CR A5 , Y 9 R in A5 It is not connected to the adjacent ring structure or is connected to form a ring through a single bond.
[0090] Preferably, the organic compound has a structure as shown in any one of Formula IV-1 to Formula IV-14:
[0091] Wherein, a dotted line represents a single bond or no connection. It is understood that in the structures shown in Formulas IV-1 to IV-9, and IV-14, the single bond indicated by the dotted line may or may not exist; when a dotted line represents a single bond, it means that the rings are connected to form a ring through a single bond; when a dotted line represents no connection, that is, the chemical bond indicated by the dotted line does not exist. When the same description is mentioned below, it has the same meaning and will not be repeated one by one.
[0092] X 1 、X 2 、X 3、X 5 、X 6 、X 7 、X 8 、M1、Q1、Q2、Q3、Q4、Y 1 、Y 2 、Y 3 、Z 1 、Z 2 、Z 3 , Ar2 has the same limited range as above.
[0093] Y 5 、Y 6 、Y 7 、Y 8 Each independently selected from CR A5 or N; multiple (e.g. 2, 3, 4, 5) CRs A5 R in A5 are the same or different groups.
[0094] R A5 Each is independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; two adjacent R A5 They are not connected or connected to form a ring through chemical bonds; R A5 Each is independently not connected to the adjacent ring structure or connected to form a ring through a chemical bond.
[0095] It should be noted that hydrogen at any position on the organic compound having a structure represented by any one of Formulas IV-1 to IV-14 may be optionally replaced by deuterium.
[0096] Preferably, the organic compound has a structure as shown in any one of Formula IV-1, Formula IV-2, Formula IV-3, Formula IV-4, Formula IV-7, Formula IV-12, Formula IV-13, and Formula IV-14, and further preferably has a structure as shown in any one of Formula IV-1, Formula IV-2, and Formula IV-3.
[0097] In this disclosure, X 1 、X 2 、X 3、X 6 、X 7 、X 8 、X 9 、Y 1 、Y 2 、Y 3 、Y 4 、Y 5 、Y 6 、Y 7 、Y 8 、Y 9 、Z 1 、Z 2 、Z 3 can be combined with the group R of the structure shown in formula a X Connected by carbon-carbon single bonds.
[0098] Preferably, the X 5 、X 6 、X 7 、Y 2 、Y 3 、Y 5 、Y 6 、Y 7 、Y 8 、Y 9 、Z 1 、Z 2 、Z 3 At least one of them is CR X , further preferably said X 6 、X 7 、Y 2 、Y 3 、Y 6 、Y 8 、Y 9 、Z 2 At least one of them is CR X .
[0099] Preferably, the Y 2 、Y 3 、Y 6 、Y 8 、Y 9 and Z 2 At least one of them is CR X .
[0100] Preferably, the X 1 、X 2 、X 3 At most one (0 or 1) is N; and / or, the X 5 、X 6 、X 7 、X 8 There is at most one (0 or 1) in N.
[0101] Preferably, the X 1 、X 2 、X 3 Each independently CR A1 ; and / or, said X 5 、X 6 、X 7 、X 8 Each independently CR A4 .
[0102] Preferably, the R A1 、R A4 Each is independently selected from hydrogen, fluorine, cyano, substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C5-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C3-C10 alkylsilyl, substituted or unsubstituted C2-C10 alkylamino, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, any one of substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl, further preferably hydrogen, cyano, substituted or unsubstituted C1-C5 straight or branched alkyl, substituted or unsubstituted C3-C10 alkylsilyl, substituted or unsubstituted C6-C20 arylamino, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C3-C20 heteroaryl; any hydrogen in the foregoing groups may be optionally substituted by deuterium.
[0103] Preferably, the R A1 、R A4 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, cyano, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, substituted or unsubstituted C3-C20 heteroaryl (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.), and is more preferably hydrogen.
[0104] Preferably, the X 1 、X 2 and X 3 are CH; and / or, the X 5 、X 6 、X 7and X 8 All are CH.
[0105] Preferably, at most one (0 or 1) among Q1, Q2, Q3, and Q4 is N.
[0106] Preferably, Q1, Q2, Q3, and Q4 are each independently CR D1 .
[0107] Preferably, the R D1 Each is independently selected from any one of hydrogen, unsubstituted or R'-substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, unsubstituted or R'-substituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, unsubstituted or R'-substituted C3-C20 heteroaryl (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.), and any hydrogen in the foregoing groups may be optionally replaced by deuterium; further preferably, hydrogen.
[0108] Preferably, Q1, Q2, Q3 and Q4 are all CH.
[0109] Preferably, the Y 1 、Y 2 and Y 3 At most one (0 or 1) is N; and / or, the Y 5 、Y 6 、Y 7 and Y 8 There is at most one (0 or 1) in N.
[0110] Preferably, the Y 1 、Y 2 、Y 3 Each independently CR A2 .
[0111] Preferably, the Y 1 、Y 2 and Y 3 The number of CHs in the SEQ ID NO: 1 is 1-3, for example, the number of CHs can be 1, 2 or 3.
[0112] Preferably, the Y 1 is CH, the Y 2 、Y 3 Each independently CR A2 .
[0113] Preferably, the R A2Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C30 aryloxy, further preferably hydrogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C30 aryloxy C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) arylamino, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) aryl, substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroaryl, substituted or unsubstituted C6-C20 (e.g., C 6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryloxy, further preferably hydrogen, substituted or unsubstituted any one of the following groups: C1-C6 straight or branched alkyl, trimethylsilyl, diphenylamino, phenyl, naphthyl, anthracenyl, biphenyl, terphenyl, pyridyl, phenylnaphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, fluorenyl, phenoxy; any hydrogen in the foregoing groups may be optionally substituted by deuterium.
[0114] Preferably, the Y 5 、Y 6 、Y 7 、Y 8 Each independently selected from CR A5 .
[0115] Preferably, the Y 5 、Y 6 、Y 7 、Y 8 The number of CHs in the SEQ ID NO: 1 is 2-4, for example, the number of CHs can be 2, 3 or 4.
[0116] Preferably, when the dotted line in Formula IV-1 to Formula IV-9 and Formula IV-14 does not exist, the Y 6 、Y8 One of them is CR A5 Or, when the dotted line in formula IV-1 to IV-9 or IV-14 represents a single bond, the Y 6 、Y 7 One of them is CR A5 .
[0117] Preferably, in any one of Formula IV-10 to Formula IV-13, the Y 6 、Y 8 、Y 9 One of them is CR A5 .
[0118] Preferably, the R A5 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, more preferably hydrogen, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl Silo, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) arylamino, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) 8, etc.), further preferably hydrogen, substituted or unsubstituted any one of the following groups: C1-C6 straight or branched alkyl, trimethylsilyl, diphenylamino, phenyl, naphthyl, anthracenyl, biphenyl, terphenyl, pyridyl, phenylnaphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, fluorenyl; any hydrogen in the foregoing groups may be optionally substituted by deuterium; any hydrogen in the foregoing groups may be optionally substituted by deuterium.
[0119] Preferably, R A2 、R A5The substituents substituted in the above-mentioned are each independently selected from halogen, cyano, unsubstituted or halogenated C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl, C2-C20 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, C6-C20 (e.g., C6, C9, C10, Any one of C12, C14, C15, C16 or C18 (e.g., C12, C14, C15, C16 or C18, etc.) aryl, C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, further preferably any one of fluorine, cyano, methyl, perfluoromethyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-amyl, phenyl, carbazolyl, trimethylsilyl; any hydrogen in the foregoing groups may be optionally replaced by deuterium.
[0120] Preferably, the Z 1 、Z 2 and Z 3 There is at most one (0 or 1) in N.
[0121] Preferably, the Z 1 、Z 2 、Z 3 Each independently CR A3 .
[0122] Preferably, the Z 1 、Z 2 and Z 3 The number of CH in the mixture is 2-3.
[0123] Preferably, the Z 1 and Z 3 is CH, the Z 2 CR A3 .
[0124] Preferably, the R A3Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C60 heteroaryl, more preferably hydrogen, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, substituted or Any one of the unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl groups, further preferably hydrogen, any one of the following substituted or unsubstituted groups: C1-C6 straight or branched chain alkyl, phenyl, naphthyl, anthracenyl, biphenyl, terphenyl, pyridyl, phenylnaphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, fluorenyl.
[0125] Preferably, the Y 2 、Y 3 、Y 5 、Y 6 、Y 7 、Y 8 and Z 2 At least one of them is CR X , the R X That is, a group having the structure shown in formula a; further preferably, the Y 2 、Y 3 、Y 5 、Y 6 、Y 7 、Y 8 and Z 2 Any one of them is CR X , further preferably, the Z 2 CR X .
[0126] Preferably, the organic compound has a structure as shown in any one of Formula V-1, Formula V-2, Formula V-3, Formula V-4, Formula V-5, Formula V-6, and Formula V-7:
[0127] Wherein, a dotted line represents a single bond or no connection. When a dotted line represents a single bond, it means that the rings are connected by a single bond to form a ring; when a dotted line represents no connection, the chemical bond shown by the dotted line does not exist.
[0128] M1 is selected from O, S, NAr m1 or CR m1 R m2 Any one of .
[0129] Ar m Any one selected from unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl, preferably unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, more preferably phenyl.
[0130] R m1 、R m2 Each is independently selected from any one of hydrogen, halogen, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; the R m1 With R m2 They are not connected or connected to form a ring through chemical bonds.
[0131] Preferably, the R m1 、R m2 Each is independently selected from hydrogen, unsubstituted or R'-substituted C1-C10 (for example, C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, unsubstituted or R'-substituted C6-C20 (for example, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, and further preferably any one of hydrogen, methyl, and phenyl; any hydrogen in the aforementioned groups may be optionally replaced by deuterium.
[0132] R A2 、R A3 、R A5 Each independently represents no substitution, monosubstitution to the maximum allowed substitution.
[0133] Among them, R A2 Indicates no substitution (R A2 is hydrogen), monosubstituted, disubstituted or trisubstituted, etc.; when R A2 When it represents di- or tri-substitution, multiple R A2 are the same or different groups; R A3 、R A5 The same applies to the expression of , and for the sake of brevity, I will not elaborate on it.
[0134] R A2 、R A3 、R A5 R is each independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; A2 、R A3 、R A5 Each is independently not connected to the adjacent ring structure or connected to form a ring through a chemical bond.
[0135] The R A2 、R A3 and R A5 At least one of the groups is R X .
[0136] It should be noted that hydrogen at any position on the organic compound having a structure represented by any one of Formulas V-1 to V-7 may be optionally replaced by deuterium.
[0137] Preferably, the R A3 is the group R X .
[0138] Preferably, the R A2 Selected from hydrogen, R X, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12 , C14, C15, C16 or C18, etc.) arylamino, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryloxy, further preferably hydrogen, R X , any one of the following groups, substituted or unsubstituted: C1-C6 straight or branched alkyl, trimethylsilyl, diphenylamino, phenyl, naphthyl, biphenyl, terphenyl, pyridyl, phenylnaphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, fluorenyl, phenoxy; any hydrogen in the foregoing groups may be optionally replaced by deuterium.
[0139] Preferably, R A2 The substituents substituted in the above-mentioned are each independently selected from halogen, cyano, unsubstituted or halogenated C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl, C2-C20 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, C6-C20 (e.g., C6, C9, C10, Any one of C12, C14, C15, C16 or C18 (e.g., C12, C14, C15, C16 or C18, etc.) aryl, C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, further preferably any one of fluorine, cyano, methyl, perfluoromethyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-amyl, phenyl, carbazolyl, trimethylsilyl; any hydrogen in the foregoing groups may be optionally replaced by deuterium.
[0140] Preferably, R A2The substituted substituents are not connected to the adjacent ring structure or are connected by chemical bonds to form a ring Cy1; the ring Cy1 is selected from any one of a substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) alicyclic ring, a substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aromatic ring, and a substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaromatic ring, and more preferably The dashed line represents the fusion site of ring Cy1; any hydrogen in the preceding structure may optionally be replaced by deuterium.
[0141] Preferably, the R A3 Selected from hydrogen, R X , substituted or unsubstituted C1-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl, substituted or unsubstituted C6-C20 (such as C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, further preferably hydrogen, R X , any one of the following groups, substituted or unsubstituted: C1-C6 straight or branched alkyl, phenyl, naphthyl, biphenyl; any hydrogen in the foregoing groups may be optionally replaced by deuterium.
[0142] Preferably, R A3 The substituents substituted in the above-mentioned are each independently selected from halogen, cyano, unsubstituted or halogenated C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, C2-C20 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, C3-C20 (for example, C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, further preferably any one of fluorine, cyano, methyl, perfluoromethyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-amyl, phenyl, and carbazolyl; any hydrogen in the foregoing groups may be optionally replaced by deuterium.
[0143] Preferably, the R A5 Selected from hydrogen, R X, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) arylamino, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, more preferably hydrogen, R X , any one of the following groups, substituted or unsubstituted: C1-C6 straight chain or branched alkyl, trimethylsilyl, diphenylamino, phenyl, naphthyl, biphenyl, terphenyl, pyridyl, phenylnaphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, fluorenyl; any hydrogen in the foregoing groups may be optionally replaced by deuterium.
[0144] Preferably, R A5 The substituents substituted in the above-mentioned are each independently selected from halogen, cyano, unsubstituted or halogenated C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl, C2-C20 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, C6-C20 (e.g., C6, C9, C10, Any one of C12, C14, C15, C16 or C18 (e.g., C12, C14, C15, C16 or C18, etc.) aryl, C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, further preferably any one of fluorine, cyano, methyl, perfluoromethyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-amyl, phenyl, carbazolyl, trimethylsilyl; any hydrogen in the foregoing groups may be optionally replaced by deuterium.
[0145] Preferably, R A5The substituted substituents are not connected to the adjacent ring structure or are connected by chemical bonds to form a ring Cy2; the ring Cy2 is selected from any one of a substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) alicyclic ring, a substituted or unsubstituted C6-C20 (e.g., C9, C10, C12, C14, C15, C16, C18, etc.) aromatic ring, a substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaromatic ring, and more preferably The dashed line represents the fusion site of ring Cy2; any hydrogen in the preceding structure may optionally be replaced by deuterium.
[0146] Preferably, the R A2 、R A5 are each independently selected from hydrogen, deuterium, R X , methyl, ethyl, Any one of; any hydrogen in the aforementioned groups may be optionally replaced by deuterium.
[0147] Preferably, the R A3 Selected from hydrogen, deuterium, R X , methyl, deuterated methyl, ethyl, Any one of; any hydrogen in the aforementioned groups may be optionally replaced by deuterium.
[0148] Preferably, the R X Having the structure shown in formula c:
[0149] In formula c, --* represents the attachment site of the group;
[0150] In formula c, R C1 represents no substitution, monosubstitution to the maximum allowed substitution; specifically, R C1 Indicates no substitution (R C1 is hydrogen), monosubstituted, disubstituted, trisubstituted, tetrasubstituted, pentasubstituted, hexasubstituted, etc.; when R C1 When multiple substitutions are indicated, multiple R C1 are the same or different groups.
[0151] L, R C1 Has the same defined range as in formula a.
[0152] Preferably, the R C1 Indicates monosubstitution up to the maximum allowed substitution.
[0153] Preferably, the R C1 The number of substitutions is 1-9, for example, 1, 2, 3, 4, 5, 6, 7, 8 or 9, more preferably 1-3.
[0154] Preferably, the R C1 The connection site is at least one of position 2, position 3, position 6, position 7, position 9, and position 10 in formula c, preferably position 9 or position 10.
[0155] Preferably, the R X Having the structure shown in formula d, or, said R X It has the structure shown in formula e:
[0156] In formula d and formula e, R 11 Any one selected from hydrogen, halogen, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl.
[0157] In formula d and formula e, R 12 、R 13 Each independently represents no substitution, monosubstitution to the maximum allowed substitution; specifically, R 12 Indicates no substitution (R 12 is hydrogen), monosubstituted, disubstituted, trisubstituted, tetrasubstituted; when R 12 When multiple substitutions are indicated, multiple R 12 are the same or different groups; R 13 Similarly, no further details will be given. 12 、R 13 Preferably it means unsubstituted or monosubstituted.
[0158] R 12 、R 13are each independently selected from hydrogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 Any one of a cycloalkyl group, an unsubstituted or R'-substituted C1-C20 alkoxy group, an unsubstituted or R'-substituted C1-C20 alkylsilyl group, an unsubstituted or R'-substituted C6-C30 arylsilyl group, an unsubstituted or R'-substituted C1-C20 alkylamino group, an unsubstituted or R'-substituted C6-C30 arylamino group, an unsubstituted or R'-substituted C6-C30 aryloxy group, an unsubstituted or R'-substituted C6-C60 aryl group, or an unsubstituted or R'-substituted C3-C60 heteroaryl group, is further preferably hydrogen, any one of a C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl group, or a C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) aryl group, is further preferably hydrogen.
[0159] In formula e, R 14 Any one selected from hydrogen, halogen, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl.
[0160] It should be noted that the R X Any hydrogen in may optionally be replaced by deuterium.
[0161] Preferably, the R X The structure is Or, the R X The structure is
[0162] Preferably, the R 11selected from hydrogen, unsubstituted or R'-substituted C1-C10 straight or branched alkyl, unsubstituted or R'-substituted C3-C10 cycloalkyl, unsubstituted or R'-substituted C3-C10 alkylsilyl, unsubstituted or R'-substituted C6-C20 aryloxy, unsubstituted or R'-substituted C6-C20 arylamino, unsubstituted or R'-substituted C6-C20 arylsilyl, unsubstituted or R'-substituted C6-C20 aryl, unsubstituted or R'-substituted Any one of the R'-substituted C3-C20 heteroaryl groups, further preferably any one of the unsubstituted or R'-substituted C1-C5 straight or branched alkyl groups, unsubstituted or R'-substituted C3-C6 alkylsilyl groups, unsubstituted or R'-substituted C6-C20 arylsilyl groups, unsubstituted or R'-substituted C6-C20 aryl groups, and unsubstituted or R'-substituted C3-C20 heteroaryl groups; any hydrogen in the aforementioned groups may be optionally replaced by deuterium.
[0163] Preferably, the R 14 any one selected from hydrogen, unsubstituted or R'-substituted C1-C10 straight or branched alkyl, unsubstituted or R'-substituted C3-C10 cycloalkyl, unsubstituted or R'-substituted C3-C10 alkylsilyl, unsubstituted or R'-substituted C6-C20 aryloxy, unsubstituted or R'-substituted C6-C20 arylamino, unsubstituted or R'-substituted C6-C20 arylsilyl, unsubstituted or R'-substituted C6-C20 aryl, unsubstituted or R'-substituted C3-C20 heteroaryl, further preferably unsubstituted or R'-substituted C1-C5 straight or branched alkyl, unsubstituted or R'-substituted C3-C6 alkylsilyl, unsubstituted or R'-substituted C6-C20 arylsilyl, unsubstituted or R'-substituted C6-C20 aryl, unsubstituted or R'-substituted C3-C20 heteroaryl Preferably, the present invention further comprises any one of hydrogen, unsubstituted or R'-substituted C1-C10 (for example, C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, unsubstituted or R'-substituted C6-C20 (for example, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, and any one of unsubstituted or R'-substituted C3-C20 heteroaryl. Preferably, the present invention further comprises any one of unsubstituted or R'-substituted C1-C6 straight or branched alkyl, phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, fluorenyl, pyridyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl. Any hydrogen in the foregoing groups may be optionally substituted by deuterium.
[0164] Preferably, R 14The R' in each of the above is independently selected from halogen, cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, C2-C20 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, C3-C20 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, C1-C10 (for example, C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl or a combination of at least two thereof, and further preferably any one of fluorine, cyano, methyl, perfluoromethyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-amyl, phenyl, trimethylsilyl; any hydrogen in the foregoing groups may optionally be replaced by deuterium.
[0165] Preferably, L is selected from any one of the following groups:
[0166] Wherein, ——* represents the attachment site of the group.
[0167] Y 11 、Y 12 、Y 13 、Y 14 、Y 15 、Y 16 、Y 17 、Y 18 、Y 19 Each independently selected from CR 21 or any one of N; multiple (for example, 2, 3, 4; for example, 2, 3, 4, 5, 6, 7, 8, 9) CR 21 R in 21 are the same or different groups.
[0168] M3 are each independently selected from O, S, NAr m2 or CR m5 R m6 Any one of .
[0169] Ar m2 Any one selected from unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl, preferably unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, further preferably phenyl; any hydrogen in the aforementioned groups may be optionally replaced by deuterium.
[0170] R21 、R m5 、R m6 R is independently selected from any one of hydrogen, halogen, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; R 21 Each independently is not connected to the adjacent ring structure or is connected to form a ring through a chemical bond; the R m3 With R m4 They are not connected to each other or are connected to form a ring through chemical bonds; any hydrogen in the aforementioned groups may be optionally replaced by deuterium.
[0171] Preferably, R m3 、R m4 Each is independently selected from hydrogen, unsubstituted or R'-substituted C1-C10 (for example, C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, unsubstituted or R'-substituted C6-C20 (for example, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, and further preferably any one of hydrogen, methyl, and phenyl; any hydrogen in the aforementioned groups may be optionally replaced by deuterium.
[0172] Preferably, said L is selected from Any one of Any one of .
[0173] Preferably, the Y 11 、Y 12 、Y 13 and Y 14 At most 2 (0, 1 or 2) of them are N.
[0174] Preferably, the Y 11 、Y 12 、Y 13 and Y 14 There is at most one (0 or 1) in N.
[0175] Preferably, the Y 15 、Y 16、Y 17 and Y 18 At most 2 (0, 1 or 2) of them are N.
[0176] Preferably, the Y 16 、Y 17 、Y 18 and Y 19 At most 2 (0, 1 or 2) of them are N.
[0177] Preferably, the Y 11 、Y 12 、Y 13 、Y 14 、Y 15 、Y 16 Each independently CR 21 .
[0178] Preferably, the R 21 each independently selected from hydrogen, unsubstituted or R'substituted C1-C10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, unsubstituted or R'substituted C3-C10 (e.g. C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, unsubstituted or R'substituted C6-C20 (e.g. C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, unsubstituted or R'-substituted C3-C20 (for example, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, further preferably hydrogen, unsubstituted or R'-substituted any one of the following groups: C1-C6 straight chain or branched alkyl, phenyl, naphthyl, biphenyl, pyridyl; any hydrogen in the aforementioned groups can be optionally replaced by deuterium.
[0179] Preferably, the R 21 Each is independently selected from any one of hydrogen, methyl, ethyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-pentyl, phenyl, methylphenyl, ethylphenyl, isopropylphenyl, isobutylphenyl (2-methylpropylphenyl), tert-butylphenyl, and tert-pentylphenyl; any hydrogen in the foregoing groups may be optionally substituted by deuterium.
[0180] Preferably, L is selected from any one of the following groups:
[0181] ——* represents the attachment site of a group, and any hydrogen in the aforementioned group may be optionally replaced by deuterium.
[0182] Preferably, L is selected from any one of the following groups: Further preferred is any one of the following groups: Further preferred is any one of the following groups:
[0183] Preferably, the R 11 Any one selected from hydrogen, unsubstituted or R'-substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, unsubstituted or R'-substituted C3-C20 heteroaryl; further preferably any one of the following groups that are unsubstituted or R'-substituted: C1-C6 straight or branched alkyl, phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, fluorenyl, pyridyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl; any hydrogen in the foregoing groups may optionally be substituted by deuterium.
[0184] Preferably, R 11 The R' in each of the above is independently selected from halogen, cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, C2-C20 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, C3-C20 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, C1-C10 (for example, C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl or a combination of at least two thereof, and further preferably any one of fluorine, cyano, methyl, perfluoromethyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-amyl, phenyl, trimethylsilyl; any hydrogen in the foregoing groups may optionally be replaced by deuterium.
[0185] Preferably, the R 11 Any one selected from the following groups: methyl, -* represents the attachment site of a group; any hydrogen in the aforementioned group may be optionally replaced by deuterium.
[0186] Preferably, the R 11Any one selected from the following groups: Further preferred is any one of the following groups: Further preferred is any one of the following groups:
[0187] Preferably, the organic compound has a structure shown in any one of the following M001-M832:
[0188] In the above structure, Ph represents a phenyl group.
[0189] In a second aspect, the present disclosure provides a use of the organic compound according to the first aspect, wherein the organic compound is used in an organic electronic device.
[0190] 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, and an organic electroluminescent device is further preferred.
[0191] Preferably, the organic compound is used in an organic electroluminescent device.
[0192] Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device.
[0193] Preferably, all organic compounds are used as dyes (also known as "dopant materials", "dopants", "guest materials") of the light-emitting layer in organic electroluminescent devices.
[0194] In a third aspect, the present disclosure provides an organic electroluminescent device, comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode; the organic layer comprises at least one organic compound as described in the first aspect.
[0195] Preferably, the organic layer includes at least one organic compound having a structure shown as M001-M832.
[0196] Preferably, the organic layer includes a light-emitting layer, and the light-emitting layer includes at least one organic compound as described in the first aspect, and further preferably includes at least one organic compound with a structure shown as M001-M832.
[0197] Preferably, the light-emitting layer includes a host material and a doping material (also known as "dopant", "dye", "guest material"), and the doping material includes at least one organic compound as described in the first aspect.
[0198] Preferably, the organic compound provided in the present disclosure is used as a fluorescent doping material of a light-emitting layer.
[0199] Preferably, the mass percentage of the doping material in the light-emitting layer is 0.1-10%, for example, it can be 0.2%, 0.5%, 0.8%, 1%, 1.5%, 2%, 2.5%, 3%, 4%, 5%, 6%, 7%, 8% or 9%, and more preferably 0.3-3%.
[0200] Preferably, the host material includes any one of a P-type host material, an N-type host material, and a unimolecular exciplex host material, or a combination of at least two of them.
[0201] Preferably, the light-emitting layer further comprises a sensitizer.
[0202] Preferably, the sensitizer includes any one of a thermally activated delayed fluorescent material and a phosphorescent luminescent material, or a combination of at least two of them.
[0203] Preferably, the energy of the lowest triplet state (T1) of the sensitizer is ≥ the energy of the lowest singlet state (S1) of the organic compound disclosed herein.
[0204] Preferably, the maximum emission wavelength of the sensitizer is less than the maximum emission wavelength of the organic compound disclosed herein.
[0205] Preferably, the mass percentage of the sensitizer in the light-emitting layer is 0.1-40%, for example, it can be 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 15%, 20%, 25%, 30% or 35%, etc.
[0206] Preferably, the sensitizer includes a phosphorescent material, and the mass percentage of the phosphorescent material in the light-emitting layer is 0.1-10%.
[0207] Preferably, the sensitizer is a thermally activated delayed fluorescent material, and the mass percentage of the thermally activated delayed fluorescent material in the light-emitting layer is 1-40%.
[0208] Preferably, the organic layer further includes a hole transport region and an electron transport region.
[0209] Preferably, the hole transport region includes any one of a hole injection layer, a hole transport layer, and an electron blocking layer, or a combination of at least two of them.
[0210] Preferably, the electron transport region includes any one of an electron injection layer, an electron transport layer, and a hole blocking layer, or a combination of at least two of them.
[0211] In a preferred embodiment, the organic electroluminescent device (OLED device) includes a first electrode, a second electrode, and an organic layer located between the electrodes. The organic layer can be divided into multiple regions, such as a hole transport region, a light-emitting layer, and an electron transport region. The light-emitting layer comprises at least one organic compound as described in the first aspect, and more preferably comprises at least one organic compound having structures M001-M832.
[0212] In a preferred technical solution, the organic electroluminescent device includes a first electrode, multiple light-emitting functional layers (organic layers), and a second electrode arranged in sequence; the organic layers include 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 arranged in sequence, with the hole injection layer in contact with the first electrode (anode). The organic layer (preferably the light-emitting layer) comprises at least one organic compound as described in the first aspect, and further preferably comprises at least one organic compound having structures M001-M832.
[0213] In a preferred embodiment, a substrate can be used below the first electrode or above the second electrode. The substrate is made of glass or a polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. Furthermore, the substrate used for the display can also be provided with thin-film transistors (TFTs).
[0214] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode serves as an anode, transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), and any combination thereof can be used. When the first electrode serves as a cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) can be used, as well as any combination thereof.
[0215] The organic layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic layer can be an organic small molecule, an organic macromolecule or a polymer, or a combination thereof.
[0216] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including single-layer hole transport layers containing only one compound and single-layer hole transport layers containing multiple compounds. The hole transport region can also be a multilayer structure comprising at least one of the following: a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.
[0217] The material of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, wherein the aromatic amine derivatives include the compounds shown below as HT-1 to HT-51; or any combination thereof.
[0218] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can use one or more of the compounds HT-1 to HT-51 described above, or one or more of the compounds HI-1 to HI-3 described below. Alternatively, one or more of the compounds HT-1 to HT-51 can be doped with one or more of the compounds HI-1 to HI-3 described below.
[0219] The light-emitting layer includes a luminescent dye (i.e., dopant) that can emit light of different wavelengths and a host material (host). The light-emitting layer can be a single-color light-emitting layer that emits a single color, such as red, green, or blue. Multiple single-color light-emitting layers of different colors can be arranged in a planar pattern according to a pixel pattern, or they can be stacked together to form a multi-color light-emitting layer. When light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single-color light-emitting layer that can simultaneously emit different colors, such as red, green, and blue.
[0220] In one aspect of the present disclosure, the light-emitting layer adopts phosphorescence-sensitized fluorescent electroluminescence technology, and the main material of the light-emitting layer is selected from, but not limited to, one or more combinations of PH-1 to PH-85.
[0221] In one aspect of the present disclosure, the light-emitting layer adopts phosphorescence-sensitized fluorescent electroluminescence technology, and the sensitizer phosphorescent material can be selected from, but not limited to, one or more combinations of GPD-1 to GPD-47 listed below.
[0222] ,; where D is deuterium.
[0223] In one aspect of the present disclosure, the light-emitting layer adopts the technology of thermally activated sensitized fluorescence luminescence, and the main material of the light-emitting layer is selected from, but not limited to, one or more combinations of the above-mentioned PH-1 to PH-85.
[0224] In one aspect of the present disclosure, the light-emitting layer adopts the technology of thermally activated sensitized fluorescence luminescence. The light-emitting layer sensitizer, that is, the thermally activated delayed fluorescent material, can be selected from, but not limited to, one or more combinations of TDE1-TDE37 listed below.
[0225] In one aspect of the present disclosure, the light-emitting layer adopts a combination of phosphorescence-sensitized luminescence and thermally activated sensitized fluorescence luminescence technology. The main material of the light-emitting layer is selected from, but not limited to, one or more combinations of the above PH-1 to PH-85.
[0226] In one aspect of the present disclosure, the light-emitting layer utilizes a combination of phosphorescence-sensitized luminescence and thermally activated sensitized fluorescence. The sensitizer for the light-emitting layer includes both a phosphorescent material and a thermally activated delayed fluorescent material. The phosphorescent material can be selected from, but is not limited to, the aforementioned GPD-1 to GPD-47. The thermally activated delayed fluorescent material can be selected from, but is not limited to, the aforementioned TDE1 to TDE37.
[0227] In one aspect of the present disclosure, an electron blocking layer (EBL) is positioned between the hole transport layer and the light-emitting layer. The EBL may be composed of, but is not limited to, one or more of the compounds HT-1 to HT-51 described above, or one or more of the compounds PH-47 to PH-77 described above; or a mixture of, but not limited to, one or more of the compounds HT-1 to HT-51 and one or more of the compounds PH-47 to PH-77.
[0228] The OLED organic layer may also include an electron transport region (ETR) between the light-emitting layer and the cathode. This ETR can be a single-layer ETL, including those containing only one compound and those containing multiple compounds. The ETR can also be a multilayer structure comprising at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).
[0229] In one aspect of the present disclosure, the electron transport layer material may be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.
[0230] In one aspect of the present disclosure, a hole-blocking layer (HBL) is positioned between the electron-transporting layer and the light-emitting layer. The hole-blocking layer may be composed of, but is not limited to, one or more of the compounds ET-1 to ET-73 described above, or one or more of the compounds PH-1 to PH-46, or a mixture of, but not limited to, one or more of the compounds ET-1 to ET-73 and one or more of the compounds PH-1 to PH-46.
[0231] The device may further include an electron injection layer located between the electron transport layer and the cathode. The electron injection layer material includes, but is not limited to, one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, and Yb.
[0232] In a fourth aspect, the present disclosure provides a display device, comprising the organic electroluminescent device as described in the third aspect.
[0233] Preferably, the display device includes a display screen or a display panel.
[0234] The present disclosure also provides an electronic device, which includes the aforementioned display device.
[0235] Compared with the prior art, the present disclosure has the following beneficial effects:
[0236] In the organic compound provided by the present disclosure, the boron-nitrogen multiple resonance core structure and the specific anthracene-containing group R X The design and combination of the two organic compounds achieve the goal of adjusting light color and reducing triplet energy levels while maintaining the narrow emission spectrum and high luminous efficiency of the multi-resonance material. The organic compound has excellent electroluminescent properties, narrow spectral characteristics, and thermal stability. When used in organic electroluminescent devices, it can be used as a fluorescent dopant material for the light-emitting layer, effectively improving the device's life attenuation and efficiency roll-off, improving the device's luminous efficiency, extending the device's life, and making the device have higher color purity. DETAILED DESCRIPTION
[0237] The technical solution of the present disclosure is further described below through specific implementation methods. Those skilled in the art should understand that the embodiments are only used to help understand the present disclosure and should not be regarded as specific limitations of the present disclosure.
[0238] The organic compound represented by Formula I of the present disclosure can be synthesized by organic synthesis methods known in the art. An exemplary synthesis route is given below, but those skilled in the art can also obtain it by other methods known in the art.
[0239] In one embodiment, the organic compound has a structure as shown in Formula II, wherein Z2 CR X , the compound can be prepared by the following synthetic route:
[0240] Among them, X 1 、X 2 、X 3 、X 5 、X 6 、X 7 、X 8 、Y 1 、Y 2 、Y 3 、Y 4 , Z 1 , Z 3 , Ar2 has the same limited range as formula II, R X It has the structure shown in formula a; Hal1 is selected from any one of I, Br, or Cl, Hal2 is selected from any one of Br or Cl; Hal3 is selected from any one of F, Br, or I; wherein, when Hal3 is F, the atomic number of Hal1 is greater than or equal to Hal2, and when Hal3 is not F, the atomic number of Hal3 is greater than the atomic numbers of Hal1 and Hal2. The order of nucleophilic reaction I and nucleophilic reaction II (or coupling reaction I) can be adjusted according to the synthesis situation, that is, nucleophilic reaction I can be carried out first, followed by nucleophilic reaction II (or coupling reaction I), or nucleophilic reaction II (or coupling reaction I) can be carried out first, followed by nucleophilic reaction I. n-BuLi represents n-butyllithium, and t-BuLi represents tert-butyllithium.
[0241] The specific preparation methods of the compounds disclosed herein will be described in detail below using a number of synthesis examples as examples, but the preparation methods disclosed herein are not limited to these synthesis examples. It should be noted that obtaining the compounds is not limited to the synthesis methods and raw materials used in this disclosure, and those skilled in the art may also choose other methods or routes to obtain the compounds proposed in this disclosure. The compounds of the synthesis methods not mentioned in this disclosure are all raw materials obtained from commercial channels, or are prepared in-house using these raw materials according to known methods.
[0242] The analysis and detection of the intermediates and target products in the following synthetic examples of the present disclosure were performed using a high-resolution mass spectrometer and matrix-assisted laser desorption ionization (MALDI) technology.
[0243] Synthesis Example 1: Synthesis of Organic Compound M064
[0244] (1) Synthesis of intermediate M064-1
[0245] 1,4-Dibromo-2,6-difluorobenzene (6.0 g, 1.0 eq), 3,6-diphenylcarbazole (3.52 g, 0.5 eq), and cesium carbonate (7.19 g, 1.0 eq) were weighed and placed in a 500 mL three-necked round-bottom flask. 80 mL of N,N-dimethylformamide (DMF) was added and the mixture was heated at 40°C under a nitrogen atmosphere for 24 h. The reaction progress was monitored by thin-layer chromatography (TLC). After the reaction was completed, the mixture was allowed to cool. With stirring, the reaction system was added to a large amount of water. The precipitated solid was filtered, and the filter cake was washed with water and ethanol. After drying, the filter cake was dissolved in dichloromethane and loaded with silica gel. The intermediate M064-1 was obtained by silica gel column chromatography.
[0246] (2) Synthesis of intermediate M064-2
[0247] M064-1 (6.2 g, 1.0 eq), 5-phenyl-5,11-dihydroindole[3,2-B]carbazole (3.72 g, 1.03 eq), and cesium carbonate (8.84 g, 2.5 eq) were weighed and placed in a 500 mL three-necked round-bottom flask. 100 mL of DMF was added and the mixture was heated at 100°C under a nitrogen atmosphere for 16 h. The reaction progress was monitored by thin-layer chromatography. After the reaction was completed, the mixture was allowed to cool. With stirring, the reaction system was added to a large amount of water. The precipitated solid was filtered, and the filter cake was washed with water and ethanol. After drying, the filter cake was dissolved in dichloromethane and loaded with silica gel. The intermediate M064-2 was obtained by silica gel column chromatography.
[0248] (3) Synthesis of intermediate M064-3
[0249] M064-2 (7.5 g, 1.0 eq) was weighed and placed in a 500 mL three-necked round-bottom flask. 80 mL of anhydrous xylene was added. Under a nitrogen atmosphere, the reaction mixture was cooled to below -30°C using a liquid nitrogen-ethanol mixture. A 2.5 M n-butyllithium solution (4.4 mL, 1.3 eq) was then slowly added. The reaction system was slowly returned to room temperature and heated at 60°C for 2 h. The reaction mixture was cooled again to below -30°C using a liquid nitrogen-ethanol mixture. Boron tribromide (2.0 mL, 2.5 eq) was added. The reaction system was slowly returned to room temperature and heated at 60°C for 1 h. The reaction mixture was cooled again to below -0°C using a liquid nitrogen-ethanol mixture. N,N-diisopropylethylamine (5.6 mL, 4.0 eq) was added. The reaction system was slowly returned to room temperature and heated at 100°C for 5 h. After the reaction was completed, the mixture was allowed to stand and cool, and most of the xylene was removed by distillation under reduced pressure. The residual mixture was purified by silica gel column chromatography to obtain a crude product, which was further purified by column chromatography and recrystallization to obtain M064-3.
[0250] (4) Synthesis of target compound M064
[0251] M064-3 (1.3 g, 1.0 eq), (2-(10-tert-butyl-9-anthryl)phenyl)-boronic acid pinacol ester (1.05 g, 1.5 eq), tetrakistriphenylphosphine palladium Pd(PPh3)4 (0.09 g, 0.05 eq), and potassium carbonate (0.55 g, 2.5 eq) were weighed and placed in a 500 mL three-necked round-bottom flask. 20 mL of 1,4-dioxane and 5 mL of water were added, and the mixture was heated to reflux under a nitrogen atmosphere. The reaction progress was monitored by thin-layer chromatography. After the reaction was completed, the mixture was allowed to cool and most of the solvent was removed by rotary evaporation under reduced pressure. Dichloromethane was then added to dissolve the mixture, and the mixture was washed three times with water. The organic phase was dried over anhydrous sodium sulfate and loaded onto silica gel. The target compound M064 was obtained by silica gel column chromatography. The target molecular mass was determined by high-resolution mass spectrometry: 1041.284 (theoretical value: 1041.43).
[0252] Synthesis Example 2: Synthesis of Organic Compound M165
[0253] (1) Synthesis of intermediate M165-1
[0254] 1,4-Dibromo-2,6-difluorobenzene (8.5 g, 1.0 eq), 3,6-di-tert-butylcarbazole (4.37 g, 0.5 eq), and cesium carbonate (10.19 g, 1.0 eq) were weighed and placed in a 500 mL three-necked round-bottom flask. 100 mL of DMF was added and the mixture was heated at 40°C under a nitrogen atmosphere for 24 h. The reaction progress was monitored by thin-layer chromatography. After the reaction was completed, the mixture was allowed to cool. With stirring, the reaction system was added to a large amount of water. The precipitated solid was filtered, and the filter cake was washed with water and ethanol. After drying, the filter cake was dissolved in dichloromethane and loaded onto silica gel. The intermediate M165-1 was obtained by silica gel column chromatography.
[0255] (2) Synthesis of intermediate M165-2
[0256] M165-1 (7.0 g, 1.0 eq), 5-phenyl-5,8-dihydroindole[2,3-C]carbazole (4.51 g, 1.03 eq), and cesium carbonate (10.73 g, 2.5 eq) were weighed and placed in a 500 mL three-necked round-bottom flask. 100 mL of DMF was added and the mixture was heated at 100°C under a nitrogen atmosphere for 16 h. The reaction progress was monitored by thin-layer chromatography. After the reaction was completed, the mixture was allowed to cool. With stirring, the reaction system was added to a large amount of water. The precipitated solid was filtered, and the filter cake was washed with water and ethanol. After drying, the filter cake was dissolved in dichloromethane and loaded with silica gel. The intermediate M165-2 was obtained by silica gel column chromatography.
[0257] (3) Synthesis of intermediate M165-3
[0258] M165-2 (8.0 g, 1.0 eq) was weighed and placed in a 500 mL three-necked round-bottom flask. 80 mL of anhydrous xylene was added. Under a nitrogen atmosphere, the reaction mixture was cooled to below -30°C with a liquid nitrogen-ethanol mixture. A 2.5 M n-butyllithium solution (4.9 mL, 1.3 eq) was then slowly added. The reaction system was slowly returned to room temperature and heated at 60°C for 2 h. The reaction mixture was cooled again with a liquid nitrogen-ethanol mixture to below -30°C. Boron tribromide (2.3 mL, 2.5 eq) was added. The reaction system was slowly returned to room temperature and heated at 60°C for 1 h. The reaction mixture was cooled again with a liquid nitrogen-ethanol mixture to below -0°C. N,N-diisopropylethylamine (6.3 mL, 4.0 eq) was added. The reaction system was slowly returned to room temperature and heated at 100°C for 5 h. After the reaction was completed, the mixture was allowed to stand and cool, and most of the xylene was removed by distillation under reduced pressure. The residual mixture was purified by silica gel column chromatography to obtain a crude product, which was further purified by column chromatography and recrystallization to obtain M165-3.
[0259] (4) Synthesis of target compound M165
[0260] M165-3 (1.4 g, 1.0 eq), (2-(10-phenyl-9-anthryl)phenyl)-boronic acid pinacol ester (1.24 g, 1.5 eq), tetrakistriphenylphosphine palladium (Pd(PPh3)4) (0.10 g, 0.05 eq), and potassium carbonate (0.63 g, 2.5 eq) were placed in a 500 mL three-necked round-bottom flask. 20 mL of 1,4-dioxane and 5 mL of water were added, and the mixture was heated under reflux under a nitrogen atmosphere. The reaction progress was monitored by thin-layer chromatography. After the reaction was allowed to cool, the solvent was removed by rotary evaporation under reduced pressure. The mixture was then dissolved in dichloromethane and washed three times with water. The organic phase was dried over anhydrous sodium sulfate, loaded onto silica gel, and purified by silica gel column chromatography to yield the target compound M165. High-resolution mass spectrometry confirmed the target molecular mass to be 1021.377 (theoretical value: 1021.46).
[0261] Theoretical calculation:
[0262] In this disclosure, the theoretical calculations of organic compounds were performed using Gaussian 16. The ground state structure of the molecule was optimized using B3LYP 6-31G* / SMD to obtain the energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of the molecule in the ground state. The structures of the lowest singlet excited state and the lowest triplet excited state of the molecule were optimized using the TD-B3LYP / 6-31G* method. The excitation energies in the ground state and excited state configurations correspond to the absorption (λ abs , nm) and emission spectra (λ em, nm) (toluene as solvent, PCM solvent model); ΔE ST is the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1) in the ground state. The specific results are shown in Table 1.
[0263] The structures of the comparative compounds Ref-1, Ref-2, Ref-3, Ref-4, and Ref-5 are as follows:
[0264] Table 1
[0265] As can be seen from Table 1, compared with Ref-1, the compounds provided by the present disclosure are more suitable green light emitting materials. For Ref-2, due to the deep LUMO energy level of the 9-phenylanthracene structure, the HOMO energy level of Ref-2 is mainly distributed on the fused ring containing the boron atom, while the LUMO energy level is distributed on the substituted anthracene, showing the nature of intramolecular charge transfer, thereby leading to a broadening of the half-peak width and a decrease in the fluorescence quantum efficiency; Ref-3 and Ref-4 increase the conjugated nature of the molecule by the fusion of the benzene ring, and the corresponding LUMO energy level and triplet energy level are reduced, but the spectrum is also broadened accordingly. At the same time, the connection sites of the substituted anthracene here are carbon atoms 1 and 2, and there is no substitution on the carbon atoms at positions 9 and 10. The 9 and 10 positions of anthracene are relatively active and easily oxidized or reduced. Therefore, when Ref-3 and Ref-4 are used for electroluminescent materials, their stability is poor, which can be further demonstrated in the device data below. The device life of M485 and M467 is significantly lower than that of M165. Therefore, among the compounds disclosed herein, compounds in which both the 9- and 10-positions of the anthracene substituent are substituted are more preferred. Furthermore, theoretical calculations for M617, M663, M753, and M754 indicate that even with changes in the linker L, the compounds disclosed herein still retain the narrow spectrum properties and low T1 energy levels of multi-resonance materials.
[0266] In summary, the compounds provided by the present disclosure not only maintain the narrow spectrum and high efficiency properties of multi-resonance materials, but also reduce the T1 energy level of the molecule by introducing anthracene groups. When used as green light-emitting materials in electroluminescent devices, they are beneficial to improving the efficiency roll-off and life decay in the devices.
[0267] The compounds disclosed herein are used in light-emitting devices and can be used as doping materials for the light-emitting layer. The fluorescence emission spectrum of the compounds prepared in the above embodiments of the present disclosure was tested using a Hitachi F-4600 fluorescence spectrophotometer in a toluene solution at room temperature. The test concentration was 10 -5 mol / L, S1 and T1 are calculated from the wavelengths corresponding to the peaks of the fluorescence emission spectrum and phosphorescence emission spectrum tested at 77K, respectively. The test results are shown in Table 2:
[0268] Table 2
[0269] It can be seen from Table 2 that, compared with Ref-1, the compound provided by the present disclosure is a more suitable green light emitting material, and its narrower half-width is conducive to obtaining better color purity and higher efficiency in the device.
[0270] Table 3
[0271] As can be seen from Table 3, compared with Ref-5, which has a higher T1 energy level, the T1 energy levels of compounds M009, M533, M526, and M663 provided by the present disclosure were not detected under the test conditions, indicating that after the introduction of 9-phenylanthracene or other anthracene derivative groups through the linker L bridge, the T1 energy of this type of compound is significantly reduced, ΔE ST The nanostructured carbonyl group is significantly increased, and as a dopant material for the light-emitting layer of an organic electroluminescent device, it can significantly improve the efficiency roll-off and life decay caused by the long-life high-energy excited triplet state.
[0272] Device Examples
[0273] An organic electroluminescent device comprises an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode (Al) stacked in sequence. The method for preparing the organic electroluminescent device is as follows:
[0274] (1) A glass substrate coated with an ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone / ethanol mixed solvent, baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;
[0275] (2) Place the glass substrate with the anode in a vacuum chamber and evacuate to 1×10 -5 Pa, vacuum evaporating a mixture of HT-4:HI-3 (97 / 3, w / w) on the above anode layer as a hole injection layer with a thickness of 10 nm;
[0276] (3) Vacuum evaporation of compound HT-4 on the hole injection layer as a hole transport layer with a total film thickness of 60 nm;
[0277] (4) Vacuum evaporation of compound HT-40 on the hole transport layer as an electron blocking layer with a total film thickness of 5 nm;
[0278] (5) Vacuum evaporating a light-emitting layer on the electron blocking layer. The light-emitting layer includes a host material, a sensitizer, and a doping material (fluorescent dye). The doping ratio is adjusted by adjusting the evaporation rate of each material using a multi-source co-evaporation method. The total film thickness of the evaporation is 40 nm.
[0279] When phosphorescence sensitized luminescence technology is used, the ratio of the host material, phosphorescence sensitizer, and dopant material is 94.2:5:0.8 (w / w / w), the host material is a PH-61:PH-3 (50 / 50, w / w) mixed host, the phosphorescence sensitizer is GPD-1 or GPD-28, and the dopant material is an organic compound provided by the present disclosure;
[0280] (6) Vacuum-depositing compound ET-23 on the light-emitting layer as a hole-blocking layer with a total film thickness of 5 nm;
[0281] (7) Vacuum evaporation of a mixture of compounds ET-69:ET-57 (50 / 50, w / w) on the hole blocking layer as an electron transport layer with a total film thickness of 25 nm;
[0282] (8) Vacuum-evaporating LiF on the electron transport layer as an electron injection layer with a thickness of 1 nm;
[0283] (9) Vacuum-evaporating an Al layer with a thickness of 150 nm on the electron injection layer as the cathode of the device to obtain the organic electroluminescent device; the total evaporation rate of all organic layers and LiF is controlled at 0.1 nm / s, and the evaporation rate of the metal electrode is controlled at 1 nm / s.
[0284] The device examples in the following specific embodiments of the present disclosure all adopt the aforementioned hierarchical structure, materials, and preparation methods, with the only difference being the light-emitting layer.
[0285] Device Examples 1-15
[0286] An organic electroluminescent device, wherein the light-emitting layer adopts phosphorescence-sensitized luminescence technology, the ratio of the main material, phosphorescence sensitizer, and dopant material is 94.2:5:0.8 (w / w / w), the main material is a PH-61:PH-3 (50 / 50, w / w) mixed main body, the phosphorescence sensitizer is GPD-28, and the dopant materials are organic compounds provided by the present disclosure, as shown in Table 4.
[0287] Comparative Example 1-2
[0288] An organic electroluminescent device, wherein the light-emitting layer adopts phosphorescence sensitized light-emitting technology, and the only difference between the device embodiment 1 is that the doping material M002 is replaced by Ref-1 or Ref-5.
[0289] Device Examples 16-23
[0290] An organic electroluminescent device, wherein the light-emitting layer adopts phosphorescence-sensitized luminescence technology, the ratio of the main material, phosphorescence sensitizer, and dopant material is 94.2:5:0.8 (w / w / w), the main material is a PH-61:PH-3 (50 / 50, w / w) mixed main body, the phosphorescence sensitizer is GPD-1, and the dopant materials are organic compounds provided by the present disclosure, as shown in Table 5.
[0291] Comparative Examples 3-5
[0292] An organic electroluminescent device, the light-emitting layer adopts phosphorescence sensitized luminescence technology, and the only difference between it and device embodiment 11 is that the doping material M344 is replaced by Ref-2, Ref-3, and Ref-4.
[0293] Device Example 24
[0294] An organic electroluminescent device, the light-emitting layer adopts phosphorescence-sensitized luminescence technology, the ratio of the main material, phosphorescence sensitizer, and dopant material is 94.2:5:0.8 (w / w / w), the main material is a PH-61:PH-3 (50 / 50, w / w) mixed main body, the phosphorescence sensitizer is GPD-50, and the dopant material is the organic compound M553 provided by the present disclosure.
[0295] Comparative Example 6
[0296] An organic electroluminescent device, the light-emitting layer adopts phosphorescence-sensitized luminescence technology. The only difference between it and device embodiment 24 is that the light-emitting layer is not doped with the organic compound provided by the present disclosure, the ratio of the main material and the phosphorescence sensitizer is 90:10 (w / w), the main material is a PH-61:PH-3 (50 / 50, w / w) mixed main body, and the phosphorescent material is GPD-50.
[0297] A top-emitting organic electroluminescent device comprises an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode (Al) stacked in sequence. The method for preparing the organic electroluminescent device is as follows:
[0298] (1) A glass substrate coated with an ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone / ethanol mixed solvent, baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;
[0299] (2) Place the glass substrate with the anode in a vacuum chamber and evacuate to a vacuum of <1×10 -5Pa, on the above anode layer, vacuum thermally evaporated in the order of 10 nm of HT-4:HI-3 (97 / 3, w / w) mixture as a hole injection layer; 120 nm of compound HT-4 as a hole transport layer; and 30 nm of compound HT-40 as an electron blocking layer;
[0300] (3) a 40 nm light-emitting layer was evaporated on the electron blocking layer. The ratio of the host material, phosphorescence sensitizer, and fluorescent dopant material in the light-emitting layer was 94.2:5:0.8 (w / w / w). The host material was a PH-61:PH-3 (50 / 50, w / w) mixed host, the phosphorescence sensitizer was GPD-44, and the dopant material was an organic compound provided by the present disclosure.
[0301] (4) 5 nm of ET-23 was evaporated on the light-emitting layer as a hole-blocking layer; 25 nm of a mixture of compounds ET-69:ET-57 (50 / 50, w / w) was used as an electron-transporting layer; and 1 nm of Yb was used as an electron-injection layer. A 13 nm Ag:Mg (11%) film was used as the cathode, with an evaporation rate of 1 Å / s at an Ag:Mg ratio of 1:0.11. HT-21 was deposited at a rate of 1 Å / s for 60 nm as the light-extraction layer. The evaporation rate of all organic layers and Yb was controlled at 0.1 nm / s.
[0302] Device Example 25
[0303] A top-emitting electroluminescent device, the light-emitting layer adopts phosphorescence-sensitized luminescence technology, the ratio of the main material, phosphorescence sensitizer, and doping material is 94.2:5:0.8 (w / w / w), the main material is a PH-61:PH-3 (50 / 50, w / w) mixed main body, the phosphorescence sensitizer is GPD-50, and the doping material is the organic compound M553 provided in the present disclosure.
[0304] Comparative Example 7
[0305] A top-emitting organic electroluminescent device, the light-emitting layer adopts phosphorescent luminescence technology. The only difference between it and device embodiment 24 is that the light-emitting layer is not doped with the organic compound provided by the present disclosure, the ratio of the main material and the phosphorescent sensitizer is 90:10 (w / w), the main material is PH-61:PH-3 (50 / 50, w / w) mixed main body, and the phosphorescent material is GPD-50.
[0306] Device performance test:
[0307] (1) Use a digital source meter and a PR650 spectroradiometer to measure the driving voltage, luminous spectrum, and external quantum efficiency of each organic electroluminescent device. Specifically, the voltage is increased at a rate of 0.1 V per second, and the current density of the organic electroluminescent device is measured when it reaches 10 mA / cm 2The voltage at this time is the driving voltage, and the external quantum efficiency (EQE,%) is measured at the same time; the life test of LT95 is as follows: use a luminance meter at 10000cd / m 2 Under the same brightness, the current is kept constant and the brightness of the organic electroluminescent device is measured to be reduced to 9500cd / m 2 The time in hours.
[0308] The EQE test value and LT95 life test value of Device Example 1 are recorded as 1.00, and the EQE and LT95 life of Device Examples 2-7 and Comparative Example 1 are the ratios of their respective EQE test values and LT95 life test values to the test value of Device Example 1 (relative EQE, relative life); the EQE test value and LT95 life test value of Device Example 11 are recorded as 1.00, and the EQE and LT95 life of Device Examples 12-13 and Comparative Examples 2-4 are the ratios of their respective EQE test values and LT95 life test values to the test value of Device Example 11 (relative EQE, relative life).
[0309] The test results are shown in Table 4 and Table 5:
[0310] Table 4
[0311] It can be seen from the performance data in Table 4 that the organic compound provided by the present disclosure is used as a fluorescent doping material, which is suitable for phosphorescence sensitized luminescence technology, and the prepared device emits saturated green light. Compared with Ref-1, the organic compound of the present disclosure is fused with indole, and the luminescent wavelength is red-shifted, and the energy transfer between the sensitizer GPD-28 is better, so the device eventually emits a narrow half-peak width green fluorescence from the organic compound described in the present disclosure, while Ref-1 has an incomplete energy transfer with GPD-28 due to the blue light color, and the final device efficiency is reduced. It is worth noting that the device life of the organic compound M465 is lower than that of M125 and M165, which is mainly attributed to the better stability of the material under electroluminescence after both the 9- and 10-position substitutions of anthracene are substituted.
[0312] Table 5
[0313] In Table 5, the organic compounds provided by the present disclosure are used as fluorescent doping materials to prepare devices with higher efficiency and lifespan. Compared to the intramolecular charge transfer properties of Ref-2, the significantly enhanced conjugated properties of Ref-3 and Ref-4, the compounds disclosed herein maintain the narrow emission spectrum and high fluorescence quantum efficiency of multi-resonance molecules, thereby having higher device efficiency. At the same time, the 9- and 10-position substitutions of anthracene in the disclosed compounds are both substituted, which has better stability and exhibits a better device lifespan.
[0314] Table 6
[0315] In Table 6, the light-emitting layer of Device Example 24 utilizes phosphorescence-sensitized fluorescence technology, employing the organic compound M553 provided in this disclosure as a fluorescent dopant. Exciton energy from the host and the phosphorescence sensitizer GPD-50 is transferred to M553, ultimately resulting in emission from the narrow-spectrum fluorescent material M553. Compared to Comparative Example 6, which exhibits a wide spectral half-width and low color purity due to a strong shoulder peak in phosphorescence, Device Example 24 exhibits a narrower emission spectrum and better color purity. Compared to Comparative Example 7, the CIEx of Device Example 25, which emits top-emission light, decreases by 0.0448, while the CIEy increases to 0.0384, demonstrating significant improvement in chromaticity achieved through sensitization technology.
[0316] The above results show that the novel organic compound disclosed in the present invention has narrow green light emission when used in organic electroluminescent devices, significantly increases the device life, and improves the luminous efficiency, and is an excellent fluorescent doping material for the light-emitting layer.
[0317] The applicant declares that while the present disclosure uses the aforementioned embodiments to illustrate the organic compounds and their applications, the present disclosure is not limited to these embodiments, nor does it imply that the present disclosure must rely on these embodiments for implementation. Persons skilled in the art should understand that any improvements to the present disclosure, equivalent substitutions for raw materials in the products of the present disclosure, addition of auxiliary components, and selection of specific methods, etc., fall within the scope of protection and disclosure of the present disclosure.
Claims
1. A boron-nitrogen fused-ring organic compound, characterized in that: The organic compound has a structure as shown in Formula I: Among them, X 1 , X 2 , X 3 , X 4 Each independently selected from CR A1 or N; Y 1 , Y 2 , Y 3 , Y 4 Each independently selected from CR A2 or N; Z 1 , Z 2 , Z 3 Each independently selected from CR A3 or N; R A1 , R A2 , R A3 Each is independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; Any two adjacent R A1 Any two adjacent R A2 Any two adjacent R A3 At least one group of them is connected by a chemical bond to form a ring F, wherein the ring F is selected from any one of a substituted or unsubstituted C6-C60 aromatic ring and a substituted or unsubstituted C3-C60 heteroaromatic ring; The R A1 , R A2 , R A3 In the above, the other groups except those forming ring F are independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds; Ar1 and Ar2 are each independently selected from unsubstituted or R B Substituted C6-C60 aryl, unsubstituted or R B Any one of substituted C3-C60 heteroaryl groups; Ar1 and Ar2 are independently not connected to adjacent ring structures or are connected to form a ring through chemical bonds; R B R is independently selected from any one of halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; B Each independently is not connected to the adjacent ring structure or is connected to form a ring through a chemical bond; R A1 , R A2 , R A3 、Ring F、R B The substituted substituents are each independently selected from halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C6-C30 arylsilyl, unsubstituted or R'substituted C1-C20 alkylamino, cyano , nitro, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl; the substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring by chemical bonds; The R A1 , R A2 , R A3 At least one of the groups is R X , and / or, the R B At least one of the groups is R X ; The R X It has the structure shown in formula a: in, The attachment site of the representative group; L is selected from any one of a substituted or unsubstituted C6-C60 arylene group and a substituted or unsubstituted C3-C60 heteroarylene group; X 11 , X 12 , X 13 , X 18 , X 19 , X 20 Each independently selected from C, CR C1 or N, one of which is C, and the C is connected to L; X 14 , X 15 , X 16 , X 17 Each independently selected from CR C1 or any one of N; R C1 Each is independently selected from any one of hydrogen, halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C6-C30 arylsilyl, unsubstituted or R'substituted C1-C20 alkylamino, cyano, nitro, unsubstituted or R'substituted C6-C30 arylamino, unsubstituted or R'substituted C3-C30 heteroarylamino, unsubstituted or R'substituted C6-C30 aryloxy, unsubstituted or R'substituted C3-C30 heteroaryloxy, unsubstituted or R'substituted C6-C60 aryl, and unsubstituted or R'substituted C3-C60 heteroaryl; The substituents substituted in L are each independently selected from any one of halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C6-C30 arylsilyl, unsubstituted or R'substituted C1-C20 alkylamino, cyano, nitro, unsubstituted or R'substituted C6-C30 arylamino, unsubstituted or R'substituted C3-C30 heteroarylamino, unsubstituted or R'substituted C6-C30 aryloxy, unsubstituted or R'substituted C3-C30 heteroaryloxy, unsubstituted or R'substituted C6-C60 aryl, and unsubstituted or R'substituted C3-C60 heteroaryl; R' is independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl, or a combination of at least two thereof; adjacent R's are not connected or are connected to form a ring by chemical bonds; the R' is not connected to adjacent ring structures or is connected to form a ring by chemical bonds.
2. The organic compound according to claim 1, characterized in that The organic compound has a structure as shown in Formula IA: Among them, the X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , Y 3 , Y 4 , Z 1 , Z 2 , Z 3 , Ar2 has the same defined range as in Formula I; X 5 , X 6 , X 7 , X 8 , X 9 Each independently selected from CR A4 or N; R A4 each independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; two adjacent R A4 They are not connected or connected to form a ring through chemical bonds; R A4 Each independently is not connected to the adjacent ring structure or is connected to form a ring through a chemical bond; Preferably, the organic compound has a structure as shown in Formula II:
3. The organic compound according to claim 2, characterized in that Any two adjacent R A1 Any two adjacent R A2 Any two adjacent R A3 Any two adjacent R A4 At least one group of them is connected by chemical bonds to form a ring F, and the ring F has a structure as shown in formula b: Among them, the dotted lines represent fused bonds; Q1, Q2, Q3, Q4 are each independently selected from CR D1 or N; R D1 R is each independently selected from any one of hydrogen, halogen, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; R D1 Each independently is not connected to the adjacent ring structure or is connected to form a ring through a chemical bond; M1 and M2 are each independently selected from a single bond, O, S, Se, NAr m1 , CR m1 R m2 or SiR m3 R m4 Any one of; at most one of M1 and M2 is a single bond; Ar m1 Any one selected from unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl; R m1 , R m2 , R m3 , R m4 Each is independently selected from any one of hydrogen, halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, unsubstituted or R'substituted C6-C60 aryl, and unsubstituted or R'substituted C3-C60 heteroaryl; the R m1 With R m2 are not connected or connected to form a ring through chemical bonds; the R m3 With R m42 They are not connected to each other or connected to form a ring through chemical bonds; Preferably, the M1 is selected from O, S, NAr m1 or CR m1 R m2 Any one of: wherein M2 is a single bond; Preferably, any two adjacent R A1 Any two adjacent R A2 Any two adjacent R A3 Any two adjacent R A4 At most four groups in are connected by chemical bonds to form ring F; Preferably, any two adjacent R A1 Any two adjacent R A4 A group of R is connected by chemical bonds to form a ring F; and / or any two adjacent R A2 One group of them is connected by chemical bonds to form ring F; Preferably, any two adjacent R A1 Any two adjacent R A2 Any two adjacent R A3 Any two adjacent R A4 A group of them are connected by chemical bonds to form ring F.
4. The organic compound according to claim 3, characterized in that The organic compound has a structure as shown in any one of Formula III-1 to Formula III-14: Wherein, M1 is selected from O, S, NAr m1 or CR m1 R m2 Any of the following; Q1, Q2, Q3, Q4, Ar m1 , R m1 , R m2 Having the same limited range as in formula b; X 1 , X 2 , X 3 , X 5 , X 6 , X 7 , X 8 , Y 1 , Y 2 , Y 3 , Y 4 , Z 1 , Z 2 , Z 3 , Ar2 has the same defined range as in Formula II; Preferably, the organic compound has a structure as shown in any one of Formula III-1, Formula III-2, Formula III-3, Formula III-4, Formula III-7, Formula III-12, Formula III-13, and Formula III-14, and further preferably has a structure as shown in any one of Formula III-1, Formula III-2, and Formula III-3.
5. The organic compound according to claim 4, characterized in that The organic compound has a structure as shown in any one of Formula IV-1 to Formula IV-14: Among them, the dashed line represents a single bond or no connection; X 1 , X 2 , X 3 , X 5 , X 6 , X 7 , X 8 、M1、Q1、Q2、Q3、Q4、Y 1 , Y 2 , Y 3 , Z 1 , Z 2 , Z 3 , Ar2 has the same definition as in claim 4; Y 5 , Y 6 , Y 7 , Y 8 Each independently selected from CR A5 or N; R A5 each independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; two adjacent R A5 They are not connected or connected to form a ring through chemical bonds; R A5 Each independently is not connected to the adjacent ring structure or is connected to form a ring through a chemical bond; Preferably, the organic compound has a structure as shown in any one of Formula IV-1, Formula IV-2, Formula IV-3, Formula IV-4, Formula IV-7, Formula IV-12, Formula IV-13, and Formula IV-14, and further preferably has a structure as shown in any one of Formula IV-1, Formula IV-2, and Formula IV-3.
6. The organic compound according to claim 5, characterized in that The X 5 , X 6 , X 7 , Y 2 , Y 3 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Z 1 , Z 2 , Z 3 At least one of them is CR X , further preferably, the X 6 , X 7 , Y 2 , Y 3 , Y 6 , Y 8 , Y 9 , Z 2 At least one of them is CR X ; Preferably, the Y 2 , Y 3 , Y 6 , Y 8 , Y 9 and Z 2 At least one of them is CR X .
7. The organic compound according to claim 5, characterized in that The X 1 , X 2 , X 3 Each independently is CR A1 ; and / or, the X 5 , X 6 , X 7 , X 8 Each independently is CR A4 ; Preferably, the R A1 , R A4 Each is independently selected from hydrogen, fluorine, cyano, substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C5-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C3-C10 alkylsilyl, substituted or unsubstituted C2-C10 alkylamino, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6 -C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, further preferably hydrogen, cyano, substituted or unsubstituted C1-C5 straight or branched alkyl, substituted or unsubstituted C3-C10 alkylsilyl, substituted or unsubstituted C6-C20 arylamino, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl; Preferably, the X 1 , X 2 and X 3 are CH; and / or, the X 5 , X 6 , X 7 and X 8 All are CH; Preferably, Q1, Q2, Q3, and Q4 are each independently CR D1 ; Preferably, Q1, Q2, Q3 and Q4 are all CH; Preferably, the Y 1 , Y 2 , Y 3 Each independently is CR A2 ; Preferably, the Y 1 , Y 2 and Y 3 The number of CH in the medium is 1-3; Preferably, the Y 1 is CH, the Y 2 , Y 3 Each independently is CR A2 ; Preferably, the R A2 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, and substituted or unsubstituted C6-C30 aryloxy; Preferably, the Y 5 , Y 6 , Y 7 , Y 8 Each independently selected from CR A5 ; Preferably, the Y 5 , Y 6 , Y 7 , Y 8 The number of CH in the medium is 2-4; Preferably, when the dashed line in Formula IV-1 to Formula IV-9 and Formula IV-14 represents absence, the Y 6 , Y 8 One of them is CR A5 ; Or, when the dotted line in Formula IV-1 to Formula IV-9 and Formula IV-14 represents a single bond, the Y 6 , Y 7 One of them is CR A5 ; Preferably, in any one of Formula IV-10 to Formula IV-13, the Y 6 , Y 8 , Y 9 One of them is CR A5 ; Preferably, the R A5 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; Preferably, the Z 1 , Z 2 , Z 3 Each independently is CR A3 ; Preferably, the Z 1 , Z 2 and Z 3 The number of CH in the medium is 2-3; Preferably, the Z 1 and Z 3 for CH, the Z 2 CR A3 ; Preferably, the R A3 Each is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight or branched alkyl, and substituted or unsubstituted C3-C60 heteroaryl.
8. The organic compound according to claim 1, characterized in that The organic compound has a structure as shown in any one of Formula V-1, Formula V-2, Formula V-3, Formula V-4, Formula V-5, Formula V-6, and Formula V-7: Among them, the dashed line represents a single bond or no connection; M1 is selected from O, S, NAr m1 or CR m1 R m2 Any of the following: Ar m Any one selected from unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl; R m1 , R m2 each independently selected from hydrogen, halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C6-C30 arylsilyl, unsubstituted or R'substituted C1-C20 alkylamino, cyano, nitro, unsubstituted or R'substituted C6-C30 arylamino, unsubstituted or R'substituted C3-C30 heteroarylamino, unsubstituted or R'substituted C6-C30 aryloxy, unsubstituted or R'substituted C3-C30 heteroaryloxy, unsubstituted or R'substituted C6-C60 aryl, unsubstituted or R'substituted C3-C60 Any one of the heteroaryl groups; said R m1 With R m2 They are not connected to each other or connected to form a ring through chemical bonds; R A2 , R A3 , R A5 Each independently represents no substitution, monosubstitution to the maximum allowed substitution; R A2 , R A3 , R A5 R is independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; A2 , R A3 , R A5 Each independently is not connected to the adjacent ring structure or is connected to form a ring through a chemical bond; The R A2 , R A3 and R A5 At least one of them is a group R X .
9. The organic compound according to claim 8, characterized in that The R A2 Selected from hydrogen, R X , any one of substituted or unsubstituted C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C1-C10 alkylsilyl, substituted or unsubstituted C6-C20 arylamino, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, substituted or unsubstituted C6-C20 aryloxy; Preferably, the R A3 Selected from hydrogen, R X , any one of a substituted or unsubstituted C1-C10 straight or branched alkyl group, and a substituted or unsubstituted C6-C20 aryl group; Preferably, the R A5 Selected from hydrogen, R X , any one of substituted or unsubstituted C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C1-C10 alkylsilyl, substituted or unsubstituted C6-C20 arylamino, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C3-C20 heteroaryl.
10. The organic compound according to any one of claims 1 to 9, characterized in that The R X It has the structure shown in formula c: in, The attachment site of the representative group; R C1 Indicates no substitution, monosubstitution to the maximum allowed substitution; L, R C1 Having the same limited range as in formula a; Preferably, the R C1 represents mono-substitution to the maximum allowed substitution; Preferably, the R C1 The number of substitutions is 1-9, more preferably 1-3; Preferably, the R C1 The connection site is at least one of position 2, position 3, position 6, position 7, position 9, and position 10 in formula c, preferably position 9 or position 10; Preferably, the R X Having a structure as shown in formula d, or, said R X It has the structure shown in formula e: Among them, R 11 is selected from hydrogen, halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C6-C30 arylsilyl, unsubstituted or R'substituted C1-C20 alkylamino, cyano, nitro, unsubstituted or R'substituted C6-C30 arylamino, unsubstituted or R'substituted C3-C30 heteroarylamino, unsubstituted or R'substituted C6-C30 Any one of an aryloxy group, an unsubstituted or R'-substituted C3-C30 heteroaryloxy group, an unsubstituted or R'-substituted C6-C60 aryl group, and an unsubstituted or R'-substituted C3-C60 heteroaryl group; R 12 , R 13 Each independently represents no substitution, monosubstitution to the maximum allowed substitution; R 12 , R 13 Each is independently selected from any one of hydrogen, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; R 14 Any one selected from hydrogen, halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C6-C30 arylsilyl, unsubstituted or R'substituted C1-C20 alkylamino, cyano, nitro, unsubstituted or R'substituted C6-C30 arylamino, unsubstituted or R'substituted C3-C30 heteroarylamino, unsubstituted or R'substituted C6-C30 aryloxy, unsubstituted or R'substituted C3-C30 heteroaryloxy, unsubstituted or R'substituted C6-C60 aryl, unsubstituted or R'substituted C3-C60 heteroaryl; Preferably, the R X The structure is Or, the R X The structure is Preferably, the R 11 Any one selected from hydrogen, unsubstituted or R'-substituted C1-C10 straight or branched alkyl, unsubstituted or R'-substituted C3-C10 cycloalkyl, unsubstituted or R'-substituted C3-C10 alkylsilyl, unsubstituted or R'-substituted C6-C20 aryloxy, unsubstituted or R'-substituted C6-C20 arylamino, unsubstituted or R'-substituted C6-C20 arylsilyl, unsubstituted or R'-substituted C6-C20 aryl, and unsubstituted or R'-substituted C3-C20 heteroaryl; further preferably any one selected from unsubstituted or R'-substituted C1-C5 straight or branched alkyl, unsubstituted or R'-substituted C3-C6 alkylsilyl, unsubstituted or R'-substituted C6-C20 arylsilyl, unsubstituted or R'-substituted C6-C20 aryl, and unsubstituted or R'-substituted C3-C20 heteroaryl; Preferably, the R 14 Any one selected from hydrogen, unsubstituted or R'-substituted C1-C10 straight or branched alkyl, unsubstituted or R'-substituted C3-C10 cycloalkyl, unsubstituted or R'-substituted C3-C10 alkylsilyl, unsubstituted or R'-substituted C6-C20 aryloxy, unsubstituted or R'-substituted C6-C20 arylamino, unsubstituted or R'-substituted C6-C20 arylsilyl, unsubstituted or R'-substituted C6-C20 aryl, and unsubstituted or R'-substituted C3-C20 heteroaryl; further preferably any one selected from unsubstituted or R'-substituted C1-C5 straight or branched alkyl, unsubstituted or R'-substituted C3-C6 alkylsilyl, unsubstituted or R'-substituted C6-C20 arylsilyl, unsubstituted or R'-substituted C6-C20 aryl, and unsubstituted or R'-substituted C3-C20 heteroaryl.
11. The organic compound according to any one of claims 1 to 10, characterized in that The L is selected from any one of the following groups: in, The attachment site of the representative group; Y 11 , Y 12 , Y 13 , Y 14 , Y 15 , Y 16 , Y 17 , Y 18 , Y 19 Each independently selected from CR 21 or any one of N; M3 are each independently selected from O, S, NAr m2 or CR m5 R m6 Any of the following: Ar m2 Any one selected from unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl; R 21 , R m5 , R m6 R is each independently selected from any one of hydrogen, halogen, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; R 21 Each independently is not connected to the adjacent ring structure or is connected to form a ring through a chemical bond; the R m5 With R m6 They are not connected to each other or connected to form a ring through chemical bonds; Preferably, L is selected from Any one of Any of the following: Preferably, the Y 11 , Y 12 , Y 13 , Y 14 , Y 15 , Y 16 Each independently is CR 21 ; Preferably, the R 21 Each is independently selected from any one of hydrogen, unsubstituted or R'-substituted C1-C10 straight or branched alkyl, unsubstituted or R'-substituted C3-C10 cycloalkyl, unsubstituted or R'-substituted C6-C20 aryl, and unsubstituted or R'-substituted C3-C20 heteroaryl.
12. The organic compound according to any one of claims 1 to 10, characterized in that The L is selected from any one of the following groups: Represents the attachment site of the group.
13. The organic compound according to claim 10, characterized in that The R 11 Any one selected from the following groups: methyl, Represents the attachment site of the group.
14. The organic compound according to claim 1, characterized in that The organic compound has a structure shown in any one of the following M001-M832:
15. Use of the organic compound according to any one of claims 1 to 14, characterized in that: The organic compound is applied to an organic electronic device; preferably, the organic electronic device comprises an organic electroluminescent device; preferably, the organic compound is used as a light-emitting layer material in the organic electroluminescent device.
16. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a first electrode, a second electrode and at least one organic layer arranged between the first electrode and the second electrode; the organic layer comprises at least one organic compound according to any one of claims 1 to 14; preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one organic compound according to any one of claims 1 to 14; preferably, the light-emitting layer comprises a host material and a doping material, and the doping material comprises at least one organic compound according to any one of claims 1 to 14; preferably, the light-emitting layer further comprises a sensitizer; preferably, the sensitizer comprises any one of a thermally activated delayed fluorescent material and a phosphorescent luminescent material, or a combination of at least two of them.
17. A display device, characterized in that: The display device comprises the organic electroluminescent device according to claim 16.
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