Compound and application thereof, and organic electroluminescent device containing compound

Abstract

The invention provides a compound and application thereof, and an organic electroluminescent device comprising the compound, the compound has a structure as shown in formula I. Through the design and mutual compounding of a specific fused ring mother nucleus structure and a specific anthracene substituent RX, the compound maintains a narrow emission spectrum and high luminous efficiency, and has a wide application prospect. According to the present invention, the purposes of triplet state energy level reduction and light color adjustment are achieved, such that the compound has excellent electroluminescent performance and narrow-spectrum luminescence characteristic, can be used for the organic electroluminescent device, can be adopted as the fluorescence doping material of the luminescent layer, can effectively improve the efficiency roll-off of the device, can improve the luminescent efficiency of the device, can prolong the service life of the device, and can be used for the organic electroluminescent device. And the device is endowed with higher color purity.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to a compound and application thereof, and an organic electroluminescent device containing the compound. Background Art

[0002] In recent years, electroluminescent devices based on organic materials (such as organic light-emitting diodes, OLEDs) have become increasingly popular. Compared with electroluminescent devices based on inorganic materials, the inherent flexibility of organic materials makes them very suitable for manufacturing flexible, thin and light 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.

[0003] With the rapid development of information technology, display technology faces higher requirements, such as meeting the color gamut standard BT-2020 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. Especially in the current commercial OLED materials, green light luminescent materials mainly use phosphorescent materials with wide half-width and strong shoulder peaks at long wavelengths. It is difficult to meet the needs of high efficiency and excellent color purity at the same time. In recent years, scientists have developed thermally activated delayed fluorescent materials (TADF) that have both 100% theoretical exciton utilization and narrow emission spectra. Using them as OLED luminescent materials is expected to meet the high color purity requirements of BT-2020 and ensure high efficiency. However, this type of material has severe efficiency roll-off at high brightness and a short device life, which is 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 TADF materials or phosphorescent materials to narrow-spectrum fluorescent materials through energy transfer, thereby achieving a theoretical 100% exciton utilization rate and obtaining a narrow emission spectrum, which 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 and platinum. Due to their low abundance, 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 in achieving the above expectations and is also a problem that needs to be solved urgently in this field. Summary of the invention

[0005] In view of the deficiencies in the prior art, the object of the present invention is to provide a compound and its application, and an organic electroluminescent device containing the same. Through the design of the compound structure, the compound has narrow spectral characteristics and excellent electroluminescent performance. It is used in organic electroluminescent devices and can be used as a doping material for the light-emitting layer, which can effectively improve the device life and luminous efficiency, and improve the color purity.

[0006] To achieve this object, the present invention adopts the following technical solutions:

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

[0008]

[0009] In formula I, Y is selected from O, S, Se, NAr 1 , CR 1 R 2 or SiR 3 R 4 Any one of .

[0010] Ar 1 Any one selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; Ar 1 It is not connected to the adjacent ring structure or is connected to form a ring through chemical bonds.

[0011] In the present invention, "Ar 1 "Not connected to the adjacent ring structure" means that Ar 1 Only connected to the N atom by a single bond; "Ar 1 The adjacent ring structure is connected to form a ring by chemical bonds. 1 In addition to being chemically bonded to the N atom, it is also chemically bonded to adjacent rings (e.g. Y 4 The rings where the two rings are located are connected by chemical bonds to form a fused ring structure. When the same descriptions are mentioned below, they all have the same meanings and will not be repeated one by one.

[0012] R 1 , R 2 , R 3 , R 4 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 C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; the R 1 With R 2 are not connected or connected to form a ring through chemical bonds, the R3 With R 4 They are not connected to each other or are connected to form a ring through chemical bonds.

[0013] In Formula I, X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 Each independently selected from CR A1 or N; multiple (e.g. 2, 3, 4, 5, 6, 7, 8, 9) CR A1 R A1 are the same or different groups.

[0014] 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) CR A2 R A2 are the same or different groups.

[0015] In Formula I, Z 1 , Z 2 , Z 3 Each independently selected from CR A3 or N; multiple (e.g. 2, 3) CR A3 R A3 are the same or different groups.

[0016] In Formula I, the X 4 With X 5 are not connected or connected to form a ring through chemical bonds, the X 9 With Z 1 There is no connection between them.

[0017] 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 alkylamino, substituted or unsubstituted C1-C20 alkylsilyl, cyano, nitro, 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-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.

[0018] 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 Cy1, and the ring Cy1 is selected from any one of a substituted or unsubstituted C6-C60 aromatic ring and a substituted or unsubstituted C5-C60 heteroaromatic ring; the ring Cy1 and the ring shown in formula I are fused with each other.

[0019] It should be noted that “any two adjacent R A1 "Does not include X 4 and X 5 In the present invention, "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.

[0020] The R A1 , R A2 , R A3 In the above, the other groups except those forming the ring Cy1 are independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds.

[0021] Ar 1 , R 1 , R 2 , R 3 , R 4 , R A1 , R A2 , R A3The substituents substituted in the ring Cy1 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 C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R'substituted C6 -Any one of C30 arylsilyl, 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 substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring by chemical bonds.

[0022] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or with multiple substituents. When there are multiple (at least 2) substituents, they may be the same or different substituents. When the same expressions are mentioned below, they have the same meaning. Unless otherwise specified, the selection range of substituents is as shown above and will not be repeated.

[0023] The R A1 , R A2 , R A3 At least one of the groups is R X , and / or, the Ar 1 , R 1 , R 2 , R 3 , R 4 At least one of the groups is R X .

[0024] It should be noted that in the compounds of the present invention, the fused ring structure is connected to at least one group R X , the R X Can be connected to X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , Y 1 , Y 2 , Y 3 , Y 4 , Z 1 , Z 2 , Z3 The C where it is located can also be connected to Y(NAr 1 , CR 1 R 2 、SiR 3 R 4 )superior.

[0025] The R X It has the structure shown in formula a:

[0026]

[0027] In formula a, Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q 10 Each independently selected from C, CR 11 or N, and one of them is C, and the C is R X connection site.

[0028] R 11 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 C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C6-C30 aryloxy, unsubstituted or R'substituted C6-C30 arylamino, unsubstituted or R'substituted C6-C30 arylsilyl, unsubstituted or R'substituted C6-C60 aryl, and unsubstituted or R'substituted C3-C60 heteroaryl; the R 11 Not all hydrogen.

[0029] 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.

[0030] In the present invention, the "unsubstituted or R'substituted" group may be substituted with one substituent R' or with multiple substituents R'. When there are multiple (at least 2) substituents R', they may be the same or different substituents. When the same expressions are mentioned below, they have the same meaning. Unless otherwise specified, the selection range of R' is as shown above and will not be repeated.

[0031] The molecular structure of the compound provided by the present invention is shown in Formula I, wherein the mother core structure includes a boron nitrogen multiple resonance (BNMR) structure and has good thermally activated delayed fluorescence (TADF) characteristics; at the same time, an anthracene substituent R with a low triplet energy level is introduced into the boron nitrogen multiple resonance structure. X , due to the anthracene substituent R X The HOMO energy level of the anthracene substituent R is lower than the HOMO energy level of the BN MR TADF material it replaces, but higher than its HOMO-1 energy level. X The LUMO energy level of the BN MRTADF material is higher than that of the material it replaces. The BN MR obtained can maintain the lowest singlet transition as the transition from HOMO to LUMO of the BN MR core structure, and the lowest triplet transition occurs in the anthracene substituent R X Therefore, the compound not only maintains the narrow spectrum and high efficiency advantages of BN MR materials, but also reduces the triplet energy level, eliminates the delayed fluorescence property of the long life of the parent core of the BN MR material, and thus improves the efficiency roll-off and life attenuation caused by the high triplet energy level and slow reverse intersystem crossing of the BN MR material. X The mutual complexation of the groups plays a role in reducing the triplet energy level and adjusting the light color, so that the compound has excellent electroluminescent properties and narrow spectral characteristics. 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.

[0032] It should be noted that, in order to facilitate explanation, the possible effects of each group / feature are described separately in the present invention, but this does not mean that these groups / features act in isolation. In fact, the essential reason for obtaining good performance is the optimized combination of the entire molecular structure, which is the result of the synergistic effect of each group, rather than the effect of a single group / feature.

[0033] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the objectives and beneficial effects of the present invention can be better achieved and realized.

[0034] In the present invention, the halogen may be fluorine, chlorine, bromine or iodine. The following descriptions involving the same have the same meaning.

[0035] In the present invention, the expression of chemical elements, unless otherwise specified, 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) includes12 C. 13 C, etc.

[0036] In the present invention, unless otherwise specified, the heteroatom of the heteroaryl group is selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0037] In the present invention, the expression of a ring structure crossed by “—” indicates that the connection site is at any position on the ring structure that can form a bond.

[0038] In the present invention, "-*" and "*" both represent the connection site of a group.

[0039] In the present invention, the expression of Ca-Cb means 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.

[0040] In the present invention, “each independently” means that when there are multiple subjects, they may be the same as or different from each other.

[0041] In the present invention, the C6-C60 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.

[0042] 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.

[0043] 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 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.

[0049] In the present invention, the C6-C60 aryl group, preferably a C6-C30 aryl group, and more preferably a C6-C20 aryl group, includes a monocyclic aryl group and a condensed 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, and exemplary examples include but are not limited to: phenyl, biphenyl, terphenyl, quaterphenyl, etc.; the condensed aryl group means that the group contains at least two aromatic rings, and the aromatic rings share two The group in which adjacent carbon atoms are fused to each other includes, but is 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 the monocyclic aromatic groups and condensed aromatic groups connected by a single bond also belong to the scope of aromatic groups, such as phenylnaphthyl, naphthylphenyl, naphthylnaphthyl, phenylnaphthylphenyl, etc.

[0050] The C3-C60 heteroaryl, preferably C6-C30 heteroaryl, further preferably C3-C20 heteroaryl, includes a monocyclic heteroaryl or a condensed ring heteroaryl. The monocyclic heteroaryl means that the molecule contains at least one heteroaryl. When the molecule contains a heteroaryl and other groups (such as aryl, heteroaryl, etc.), the heteroaryl and other groups are connected by a single bond, exemplarily including but not limited to: pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, bipyridyl, phenylpyridyl, pyridylphenyl, etc. The fused ring heteroaryl group means a group containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring) in the molecule, and the two groups 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, indolcarbazolyl, azacarbazolyl, etc.), acridinyl, phenothiazinyl, phenoxazinyl, hydroacridinyl, etc. It should be noted that heteroaryl and heteroaryl connected by a single bond, aryl and heteroaryl connected by a single bond also belong to the scope of heteroaryl, such as phenylpyridyl, phenylpyrimidinyl, diphenylpyridinyl, diphenylpyrimidinyl, etc.

[0051] In the present invention, the C6-C30 aryloxy group is a monovalent group formed by connecting the above-mentioned aryl groups and O, and the C3-C30 heteroaryloxy group is a monovalent group formed by connecting the above-mentioned heteroaryl groups and O.

[0052] In the present invention, a specific example of the C6-C30 arylamino group is a monovalent group in which at least one hydrogen in -NH2 is replaced by the above aryl group, including but not limited to phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrenylamino, biphenylamino, etc. A specific example of the C3-C30 heteroarylamino group is a monovalent group in which at least one hydrogen in -NH2 is replaced by the above heteroaryl group, including but not limited to pyridylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0053] 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.

[0054] The C1-C20 straight chain or branched alkyl group, preferably a C1-C16 straight chain or branched alkyl group, and further preferably a C1-C10 straight chain or branched 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.

[0055] Specific examples of the C1-C20 alkoxy group include monovalent groups obtained by connecting the above-mentioned linear or branched alkyl groups to O.

[0056] 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.

[0057] The C3-C20 cycloalkyl, preferably C3-C10 cycloalkyl, includes monocycloalkyl or polycycloalkyl. Monocycloalkyl refers to an alkyl group containing a single cyclic structure, and polycycloalkyl refers to a structure composed of two or more cycloalkyl groups sharing one or more carbon atoms on the ring; exemplary examples include but are not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0058] The C2-C20 alkenyl, preferably C2-C10 alkenyl, contains at least one C=C, illustratively including but not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl and the like.

[0059] Preferably, the X 4 With X 5 The compounds are connected to form a ring through a chemical bond Y', and the compound has a structure as shown in Formula II:

[0060]

[0061] In Formula II, Y, X 1 , X 2 , X 3 , X 6 , X 7 , X 8 , X 9 , Y 1 , Y 2 , Y 3 , Y 4 , Z 1 , Z 2 , Z 3 has the same definition as in Formula I.

[0062] In formula II, the Y' is selected from a single bond, O, S, Se, NAr 2 , CR 5 R 6 or SiR 7 R 8Any one of the above, more preferably a single bond. Wherein, when Y' is selected from a single bond, it represents that the ring where Y' is located is a five-membered ring (the ring where Y' and N are located is a pyrrole ring).

[0063] Ar 2 Any one selected from a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group.

[0064] R 5 , R 6 , R 7 , R 8 are 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 alkylsilyl, cyano, nitro, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; said R 5 With R 6 are not connected or connected to form a ring through chemical bonds, the R 7 With R 8 They are not connected or connected to form a ring through chemical bonds.

[0065] Ar 2 , R 5 , R 6 , R 7 , R 8 The substituents substituted in the above-mentioned substitution 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 C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R'substituted C6-C The substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring by chemical bonds.

[0066] Preferably, Y is NAr 1 .

[0067] Preferably, the X 4 With X 5 They are connected to form a ring by single bonds.

[0068] Preferably, the compound has a structure as shown in Formula III:

[0069]

[0070] In Formula III, X 1 , X 2 , X 3 , X 6 , X 7 , X 8 , X 9 , Y 1 , Y 2 , Y 3 , Y 4 , Z 1 , Z 2 , Z 3 ,Ar 1 The same limitations as above apply.

[0071] Preferably, any two adjacent R A1 Any two adjacent R A2 Any two adjacent R A3 At least one group of them is connected by chemical bonds to form a ring Cy1, and the ring Cy1 has a structure as shown in formula b:

[0072]

[0073] In formula b, the dotted line represents a fused bond.

[0074] In formula b, X 11 , X 12 , X 13 , X 14 Each independently selected from CR B1 or N; multiple (e.g. 2, 3, 4) CR B1 R B1 are the same or different groups.

[0075] In formula b, M1 and M2 are each independently selected from a single bond, O, S, NAr 3 or CR M1 R M2 any one of; at most one of M1 and M2 is a single bond. Wherein, when one of M1 and M2 is a single bond, the ring Cy1 shown in formula b can be understood as a structure in which a six-membered ring (such as a benzene ring) and a five-membered ring (such as a pyrrole ring, a furan ring, a thiophene ring, a cyclopentadiene structure) are fused; when neither M1 nor M2 is a single bond, the ring Cy1 shown in formula b can be understood as a structure in which two six-membered rings are fused.

[0076] Ar3 Any one selected from an unsubstituted or R'-substituted C6-C60 aryl group and an unsubstituted or R'-substituted C3-C60 heteroaryl group.

[0077] R B1 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 C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R'-substituted C6-C30 arylsilyl, 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 B1 Each is independently not connected to the adjacent ring structure or connected to form a ring through a chemical bond.

[0078] 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 C6-C60 aryl, and unsubstituted or R'substituted C3-C60 heteroaryl; the R M1 With R M2 They are not connected to each other or are connected to form a ring through chemical bonds.

[0079] Preferably, the M1 is selected from O, S, NAr 3 or CR M1 R M2 Any one of: wherein M2 is a single bond, and thus, the ring Cy1 is

[0080] Preferably, any two adjacent R A1 Any two adjacent R A2 Any two adjacent R A3 At most four groups in are connected by chemical bonds to form a ring Cy1.

[0081] Preferably, any two adjacent R A1 A group of them are connected by chemical bonds to form a ring Cy1; and / or any two adjacent R A2A group of them are connected by chemical bonds to form a ring Cy1.

[0082] Preferably, any two adjacent R A1 Any two adjacent R A2 Any two adjacent R A3 A group of them are connected by chemical bonds to form a ring Cy1.

[0083] Preferably, the compound has a structure as shown in any one of Formulas IV-1 to IV-13, and further preferably has a structure as shown in any one of Formulas IV-1 to IV-3:

[0084]

[0085]

[0086]

[0087] Wherein, M1 is selected from O, S, NAr 3 or CR M1 R M2 Any one of .

[0088] X 11 , X 12 , X 13 , X 14 ,Ar 3 , R B1 , R M1 , R M2 Has the same definition as in formula b.

[0089] X 1 , X 2 , X 3 , X 6 , X 7 , X 8 , X 9 , Y 1 , Y 2 , Y 3 , Y 4 , Z 1 , Z 2 , Z 3 ,Ar 1 The same limitations as above apply.

[0090] Preferably, the compound has a structure as shown in any one of Formula IV-1, Formula IV-2, Formula IV-3, Formula IV-4, Formula IV-5, Formula IV-12, and Formula IV-13, and further preferably has a structure as shown in any one of Formula IV-1 to Formula IV-3.

[0091] Preferably, the Ar 1 for -* represents the attachment site of the group, Y 5 , Y 6 , Y 7 , Y 8 , Y 9 Each independently selected from CR C1 or N; Ar 1 Y 5 With the Y in the compound 4 Not connected or connected to form a ring through chemical bonds.

[0092] Preferably, the compound has a structure as shown in any one of Formula V-1 to Formula V-13:

[0093]

[0094]

[0095]

[0096] Wherein, the dashed line represents a single bond or no connection.

[0097] It can be understood that in the structures shown in Formula V-1 to Formula V-9, the single bond shown by the dotted line may or may not exist; when the dotted line represents a single bond, it means that the rings are connected to form a ring (forming a carbazole-like structure) by a single bond; when the dotted line represents no connection, that is, the chemical bond shown by the dotted line does not exist. When the same description is involved below, it has the same meaning and will not be repeated one by one.

[0098] X 1 , X 2 , X 3 , X 6 , X 7 , X 8 , X 9 , Y 1 , Y 2 , Y 3 , Y 4 , Z 1 , Z 2 , Z 3 , M1, X 11 , X 12 , X 13 , X 14 The same limitations as above apply.

[0099] Y 5 , Y 6 , Y 7 , Y 8 , Y 9 Each independently selected from CRC1 or N; multiple (e.g. 2, 3, 4, 5) CR C1 R C1 are the same or different groups.

[0100] R C1 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 C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R'-substituted C6-C30 arylsilyl, 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 C1 Each is independently not connected to the adjacent ring structure or connected to form a ring through a chemical bond.

[0101] In the present invention, 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.

[0102] Preferably, the X 6 , X 7 , X 8 , 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, X 7 , X 8 , Y 2 , Y 3 , Y 5 , Y 7 , Y 9 , Z 2 At least one of them is CR X .

[0103] Preferably, the Y 2 , Y 3 , Y 5 , Y 7 , Y 9 and Z 2 At least one of them is CR X .

[0104] Preferably, the X 1 , X 2 , X 3 At most one (0 or 1) of X is N; and / or, the X 6 , X 7 , X 8 and X 9 There is at most 1 (0 or 1) in N.

[0105] Preferably, the X 1 , X 2 , X 3 , X 6 , X 7 , X 8 , X 9 Each independently is CR A1 .

[0106] Preferably, the R A1Each 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.

[0107] Preferably, the R A1 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.

[0108] Preferably, the X 1 , X 2 , X 3 , X 6 , X 7 , X 8 and X 9 All are CH.

[0109] Preferably, the X 11 , X 12 , X 13 and X 14 There is at most 1 (0 or 1) in N.

[0110] Preferably, the X 11 , X 12 , X 13 , X 14 Each independently is CR B1 .

[0111] Preferably, the RB1 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, and unsubstituted or R'-substituted C3-C20 heteroaryl (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.), and is more preferably hydrogen.

[0112] Preferably, the X 11 , X 12 , X 13 and X 14 All are CH.

[0113] Preferably, the Y 1 , Y 2 , Y 3 and Y 4 There is at most 1 (0 or 1) in N.

[0114] Preferably, the Y 1 , Y 2 , Y 3 , Y 4 Each independently is CR A2 .

[0115] Preferably, the Y 1 , Y 2 , Y 3 , Y 4 The number of CHs in the MAC is 1-4, for example, the number of CHs can be 1, 2, 3 or 4.

[0116] Preferably, the Y 1 and Y 4 is CH, the Y 2 , Y 3 Each independently is CR A2 .

[0117] 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, and more preferably hydrogen, substituted or unsubstituted substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight 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.) 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, and 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.

[0118] Preferably, R A2 The substituted substituents are each independently selected from any one of 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 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroaryl, and further preferably any one of fluorine, cyano, methyl, perfluoromethyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-amyl, phenyl, and carbazolyl.

[0119] Preferably, the Y 5 , Y 6 , Y 7 , Y 8 and Y9 There is at most 1 (0 or 1) in N.

[0120] Preferably, the Y 5 , Y 6 , Y 7 , Y 8 , Y 9 Each independently is CR C1 .

[0121] Preferably, the Y 5 , Y 6 , Y 7 , Y 8 , Y 9 The number of CHs in the WO 2009 / 05084 ... is 2-5, for example, the number of CHs can be 2, 3, 4 or 5.

[0122] Preferably, when the dashed line in Formula V-1 to Formula V-9 represents absence, the Y 5 , Y 7 , Y 9 One of them is CR C1 Or, when the dotted line in Formula V-1 to Formula V-9 represents a single bond, the Y 7 , Y 8 One of them is CR C1 .

[0123] Preferably, in Formula V-10 to Formula V-13, the Y 5 , Y 7 , Y 9 One of them is CR C1 .

[0124] Preferably, the R C1Each 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 C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C6-C30 arylamino, unsubstituted or R'substituted C6-C60 aryl, and unsubstituted or R'substituted C3-C60 heteroaryl, and is further preferably 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 C2-C10 (e.g. C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, unsubstituted or R'substituted C1-C10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) arylamino, 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 (e.g., C3, C4, The invention further preferably comprises any one of the following heteroaryl groups (such as C5, C6, C9, C10, C12, C14, C15, C16 or C18), and more preferably any one of hydrogen, unsubstituted or R'-substituted following groups: C1-C6 straight chain or branched alkyl, trimethylsilyl, diphenylamino, phenyl, naphthyl, anthracenyl, biphenyl, terphenyl, pyridyl, phenylnaphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, fluorenyl.

[0125] Preferably, R C1 The R' in the above-mentioned is independently selected from any one or a combination of at least two of 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, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroaryl, and is further preferably any one of fluorine, cyano, methyl, perfluoromethyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-amyl, phenyl, and carbazolyl.

[0126] Preferably, the Z 1 , Z 2 and Z3 There is at most 1 (0 or 1) in N.

[0127] Preferably, the Z 1 , Z 2 , Z 3 Each independently is CR A3 .

[0128] Preferably, the Z 1 , Z 2 and Z 3 The number of CH in the mixture is 2-3.

[0129] Preferably, the Z 1 and Z 3 for CH, the Z 2 Selected from CR A3 .

[0130] 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 C6-C60 aryl, and is further preferably hydrogen, substituted or unsubstituted C1-C10 (for example, C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, and substituted or unsubstituted C6-C20 (for example, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, and is further preferably hydrogen, substituted or unsubstituted any one of the following groups: C1-C6 straight or branched alkyl, phenyl, naphthyl, anthracenyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, and fluorenyl.

[0131] Preferably, R A3The substituents substituted in the above-mentioned are each independently selected from halogen, cyano, 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 C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, 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 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) 18, etc.) heteroaryl, unsubstituted or R'-substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) aryloxy, unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) arylamino, unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) arylsilyl.

[0132] Preferably, the Y 2 , Y 3 , Y 6 , Y 7 , Y 8 , Z 2 At least one of them is CR X , the R X That is, a group of the structure shown in formula a; further preferably, the Y 2 , Y 3 , Y 6 , Y 7 , Y 8 and Z 2 Any one of them is CR X .

[0133] Preferably, the Z 2 CR X .

[0134] Preferably, the compound has a structure as shown in any one of Formula VI-1 to Formula VI-10:

[0135]

[0136] Wherein, M1 is selected from O, S, NAr 3 or CR M1 R M2Any one of .

[0137] Ar 3 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.

[0138] 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 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.

[0139] Preferably, the R M1 , R M2 Each is 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 C6-C20 (e.g. C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, and any one of hydrogen, methyl and phenyl is further preferred.

[0140] R A2 , R A3 , R C1 Each independently represents no substitution, monosubstitution to the maximum allowed substitution.

[0141] Among them, R A2 Indicates no substitution (R A2 is hydrogen), monosubstituted, disubstituted or trisubstituted, etc.; when R A2 When it indicates di- or tri-substitution, multiple R A2 are the same or different groups; R A3 , R C1 The statement is the same, and for the sake of brevity, I will not repeat it.

[0142] R A2 , R A3R 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 alkylsilyl, 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 Each is independently not connected to the adjacent ring structure or connected to form a ring through a chemical bond.

[0143] R C1 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 C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R'-substituted C6-C30 arylsilyl, 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 C1 Each is independently not connected to the adjacent ring structure or connected to form a ring through a chemical bond.

[0144] The R A2 , R A3 and R C1 At least one of the groups is R X .

[0145] Preferably, the R C1 For the group R X .

[0146] Preferably, the R X It has the structure shown in formula c:

[0147]

[0148] In formula c, -* represents the attachment site of the group;

[0149] In formula c, R 11 represents monosubstitution to the maximum allowed substitution; specifically, R 11represents mono-, di-, tri-, tetra-, penta-, hexa-, etc. substitutions; when R 11 When multiple substitutions are indicated, multiple R 11 are the same or different groups.

[0150] R 11 Each is independently selected from any one of 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 aryloxy, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl.

[0151] Preferably, the R 11 The number of substitutions is 1-9, for example, 1, 2, 3, 4, 5, 6, 7, 8 or 9, more preferably 1-3.

[0152] Preferably, the R 11 The attachment site is at least one of position 2, position 3, position 6, position 7, position 9, and position 10 in formula c, and more preferably position 9 or position 10.

[0153] Preferably, the R 11 Each is independently selected from any one of 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, and is further preferably any one of 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.

[0154] Preferably, the R X It has the structure shown in formula d:

[0155]

[0156] In formula d, R 21Any one selected from 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 aryloxy, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl.

[0157] In formula d, R 22 , R 23 Each independently represents no substitution, mono-substitution to the maximum permissible substitution; specifically, R 22 Indicates no substitution (R 22 is hydrogen), monosubstituted, disubstituted, trisubstituted, tetrasubstituted; when R 22 When multiple substitutions are indicated, multiple R 22 are the same or different groups; R 23 Similarly, no further description is given. 22 , R 23 Preferably it means unsubstituted or monosubstituted.

[0158] R 22 , R 23 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 C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl, and is further preferably any one of hydrogen, C1-C5 straight or branched alkyl, unsubstituted or R'-substituted C6-C20 aryl, and unsubstituted or R'-substituted C3-C20 heteroaryl.

[0159] Preferably, the R 21selected from unsubstituted or R'-substituted C1-C5 (e.g., C2, C3, C4, etc.) straight or branched alkyl, unsubstituted or R'-substituted C3-C6 (e.g., C4, C5, C6, etc.) alkylsilyl, unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) arylsilyl, unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) aryloxy, unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) The present invention further preferably comprises any one of an unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) arylamino, an unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, and an unsubstituted or R'-substituted C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl. Further preferably, any one of an unsubstituted or R'-substituted C1-C5 straight or branched alkyl, an unsubstituted or R'-substituted C3-C6 alkylsilyl, an unsubstituted or R'-substituted C6-C20 arylsilyl, and an unsubstituted or R'-substituted C6-C20 aryl.

[0160] Preferably, the R 21 selected from 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, unsubstituted or R'substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy, unsubstituted or R'substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, unsubstituted or R'substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) any one of the following groups which are unsubstituted or R'substituted: C1-C6 straight or branched alkyl, phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, fluorenyl, pyridyl, carbazolyl, triphenylsilyl, diphenylamino, phenoxy, C1-C6 straight or branched alkoxy.

[0161] Preferably, R 21 The R' in the formula (a) 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, C any one or a combination of at least two of a C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18 (e.g., C4, C5, C6, C7, C8, C9, etc.) heteroaryl, a C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl, and more preferably any one of fluorine, cyano, methyl, perfluoromethyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-amyl, phenyl and trimethylsilyl.

[0162] Preferably, the R 21 Any one selected from the following groups:

[0163] -* represents the attachment site of the group.

[0164] Preferably, the R 21 Any one selected from the following groups:

[0165]

[0166] Preferably, the R A2 are each independently 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.) alkane any one of a silyl group, a substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) arylamino group, a substituted or unsubstituted C6-C12 (e.g., C6, C9, C10, C12, etc.) aryl group, a substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroaryl group, and more preferably hydrogen, RX , any one of the following substituted or unsubstituted groups: C1-C6 straight chain or branched alkyl, trimethylsilyl, diphenylamino, phenyl, naphthyl, biphenyl, terphenyl, pyridyl, phenylnaphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, fluorenyl.

[0167] Preferably, R A2 The substituted substituents are each independently selected from any one of 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 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroaryl, and further preferably any one of fluorine, cyano, methyl, perfluoromethyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-amyl, phenyl, and carbazolyl.

[0168] Preferably, R A2 The 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., 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 Cy2.

[0169] Preferably, the R A3 are each independently selected from hydrogen, R X , substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight chain or branched alkyl, substituted or unsubstituted C6-C12 (e.g., C6, C9, C10, C12, etc.) aryl, more preferably hydrogen, R X , any one of the following substituted or unsubstituted groups: C1-C6 straight chain or branched alkyl, phenyl, naphthyl, biphenyl.

[0170] Preferably, R A3The substituted substituents are each independently selected from any one of 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 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroaryl, and further preferably any one of fluorine, cyano, methyl, perfluoromethyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-amyl, phenyl, and carbazolyl.

[0171] Preferably, the R C1 are each independently selected from hydrogen, R X , unsubstituted or R'substituted C1-C10 straight or branched alkyl, unsubstituted or R'substituted C3-C10 cycloalkyl, unsubstituted or R'substituted C2-C10 alkenyl, unsubstituted or R'substituted C1-C10 alkylsilyl, unsubstituted or R'substituted C6-C20 arylamino, unsubstituted or R'substituted C6-C12 aryl, unsubstituted or R'substituted C3-C20 heteroaryl, and more preferably hydrogen, R X , any one of the following groups which are unsubstituted or R'-substituted: C1-C6 straight or branched alkyl, trimethylsilyl, diphenylamino, phenyl, naphthyl, biphenyl, terphenyl, pyridyl, phenylnaphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, fluorenyl.

[0172] Preferably, R C1 The R' in the above-mentioned is independently selected from any one or a combination of at least two of 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, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroaryl, and is further preferably any one of fluorine, cyano, methyl, perfluoromethyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-amyl, phenyl, and carbazolyl.

[0173] Preferably, R C1The R' in the ring is not connected to the adjacent ring structure or is connected to form a ring Cy3 by a chemical bond; the ring Cy3 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 is further preferably The dashed line represents the fusion site of ring Cy3.

[0174] Preferably, the R A2 , R C1 are each independently selected from hydrogen, R X , methyl, ethyl,

[0175] Any one of .

[0176] Preferably, the R A3 Selected from hydrogen, R X , methyl, ethyl, Any one of .

[0177] Preferably, the compound has a structure shown in any one of the following M001-M365:

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200] In a second aspect, the present invention provides a use of the compound as described in the first aspect, wherein the compound is used in an organic electronic device.

[0201] 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.

[0202] Preferably, the compound is used in an organic electroluminescent device.

[0203] Preferably, the compound is used as a light-emitting layer material in an organic electroluminescent device.

[0204] Preferably, the compound is used as a dye (also known as "doping material", "dopant", "guest material") of the light-emitting layer in an organic electroluminescent device.

[0205] In a third aspect, the present invention 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 compound as described in the first aspect.

[0206] Preferably, the organic layer comprises at least one compound having a structure shown by M001-M365.

[0207] Preferably, the organic layer includes a light-emitting layer, and the light-emitting layer includes at least one compound as described in the first aspect, and further preferably includes a compound with a structure shown as M001-M365.

[0208] Preferably, the light-emitting layer comprises a host material and a doping material (also known as a "dopant", "dye", or "guest material"), and the doping material comprises at least one compound as described in the first aspect.

[0209] Preferably, the compound provided by the present invention is used as a fluorescent doping material (fluorescent dye) of a light-emitting layer.

[0210] 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%, etc., and more preferably 0.3-3%.

[0211] Preferably, the host material includes any one of a P-type host material, an N-type host material, and a single-molecule exciplex host material, or a combination of at least two of them.

[0212] Preferably, the light-emitting layer further comprises a sensitizer.

[0213] 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.

[0214] 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.

[0215] Preferably, the energy of the lowest triplet state (T1) of the sensitizer is ≥ the energy of the lowest singlet state (S1) of the compound of the present invention.

[0216] Preferably, the maximum emission wavelength of the sensitizer is less than the maximum emission wavelength of the compound of the present invention.

[0217] 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.

[0218] Preferably, the sensitizer comprises a phosphorescent material, and the mass percentage of the phosphorescent material in the light-emitting layer is 0.1-10%.

[0219] 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%.

[0220] Preferably, the organic layer further includes a hole transport region and an electron transport region.

[0221] 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.

[0222] 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.

[0223] In a preferred technical solution, the organic electroluminescent device (OLED device) comprises a first electrode and a second electrode, and an organic layer located between the electrodes. The organic layer can be divided into multiple regions, for example, a hole transport region, a light-emitting layer, and an electron transport region; the light-emitting layer comprises at least one compound as described in the first aspect, and further preferably comprises at least one compound having a structure shown in M001-M365.

[0224] In a preferred technical solution, the organic electroluminescent device comprises a first electrode, a plurality of light-emitting functional layers (organic layers) and a second electrode arranged in sequence; the organic layer comprises 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, and the hole injection layer is in contact with the first electrode (anode). The organic layer (preferably the light-emitting layer) comprises at least one compound as described in the first aspect, and further preferably comprises at least one compound of the structure shown in M001-M365.

[0225] In a preferred technical solution, a substrate can be used below the first electrode or above the second electrode. The substrate is glass or polymer material with excellent mechanical strength, thermal stability, water resistance and transparency. In addition, a thin film transistor (TFT) can also be provided on the substrate used as a display.

[0226] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material 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 is used as a cathode, a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and any combination thereof can be used.

[0227] 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, and a combination thereof.

[0228] 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 a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one layer of 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.

[0229] 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 in HT-1 to HT-51 below; or any combination thereof.

[0230]

[0231]

[0232]

[0233] 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 compounds of HT-1 to HT-51 above, or one or more compounds of HI-1 to HI-3 below; or one or more compounds of HT-1 to HT-51 can be doped with one or more compounds of HI-1 to HI-3 below.

[0234]

[0235] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra and a host material (Host). The light-emitting layer can be a monochrome light-emitting layer that emits a single color such as red, green, and blue. A plurality of monochrome light-emitting layers of different colors can be arranged in a plane according to a pixel pattern, or they can be stacked together to form a 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.

[0236] In one aspect of the present invention, 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.

[0237]

[0238]

[0239]

[0240]

[0241] In one aspect of the present invention, the light-emitting layer adopts phosphorescence-sensitized fluorescent electroluminescence technology. The sensitizer phosphorescent material can be selected from, but not limited to, one or more combinations of GPD-1 to GPD-47 listed below.

[0242]

[0243]

[0244]

[0245] Where D is deuterium.

[0246] In one aspect of the present invention, the light-emitting layer adopts the technology of thermally activated sensitized fluorescence luminescence. 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.

[0247] In one aspect of the present invention, 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.

[0248]

[0249]

[0250]

[0251] In one aspect of the present invention, the light-emitting layer adopts the technology of combining phosphorescence sensitized luminescence and thermally activated sensitized fluorescence luminescence. 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.

[0252] In one aspect of the present invention, the light-emitting layer adopts a technology combining phosphorescence sensitized luminescence and thermally activated sensitized fluorescence luminescence. The light-emitting layer sensitizer includes both phosphorescent materials and thermally activated delayed fluorescence materials. The phosphorescent materials can be selected from, but not limited to, the GPD-1 to GPD-47 listed above, and the thermally activated delayed fluorescence materials can be selected from, but not limited to, the TDE1-TDE37 listed above.

[0253] In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be, but 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.

[0254] The OLED organic layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region may also be a multi-layer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0255] In one aspect of the present invention, the electron transport layer material can be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0256]

[0257]

[0258]

[0259]

[0260] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may be, but not limited to, one or more compounds of ET-1 to ET-73, or one or more compounds of PH-1 to PH-46; or a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-46.

[0261] The device may also 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.

[0262] In a fourth aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the third aspect.

[0263] Preferably, the display device includes a display screen or a display panel.

[0264] The present invention also provides an electronic device, which includes the above-mentioned display device.

[0265] Compared with the prior art, the present invention has the following beneficial effects:

[0266] In the compounds provided by the present invention, a specific fused ring core structure and a specific anthracene substituent R X The design and mutual compounding enable it to achieve the purpose of reducing the triplet energy level and adjusting the light color while maintaining a narrow emission spectrum and high luminous efficiency, so that the compound has excellent electroluminescent performance and narrow spectrum luminescent characteristics. It is used in organic electroluminescent devices and can be used as a fluorescent doping material for the light-emitting layer, which can effectively improve the efficiency roll-off of the device, improve the luminous efficiency of the device, extend the life of the device, and give the device higher color purity. DETAILED DESCRIPTION

[0267] The technical solution of the present invention is further described below by specific implementation methods. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0268] The compound represented by formula I of the present invention 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.

[0269] In one embodiment, the compound has a structure as shown in Formula III, wherein Z 2 CR X, the compound can be prepared by the following synthetic route:

[0270]

[0271] Among them, X 1 , X 2 , X 3 , X 6 , X 7 , X 8 , X 9 , Y 1 , Y 2 , Y 3 , Y 4 , Z 1 , Z 3 ,Ar 1 It has the same limited range as formula III; when Hal3 is F, Hal1 and Hal2 are each independently selected from any one of I, Br or Cl, wherein the atomic number of Hal1 is greater than or equal to the atomic number of 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, then nucleophilic reaction II, or nucleophilic reaction II can be carried out first, then nucleophilic reaction I. When Hal3 is I or Br, Hal1 and Hal2 are each independently selected from any one of Br or Cl, wherein the atomic number of Hal3 is greater than the atomic number of Hal1 and Hal2; at this time, the order of nucleophilic reaction I and coupling reaction I can be adjusted according to the synthesis situation, that is, nucleophilic reaction I can be carried out first, then coupling reaction I, or coupling reaction I can be carried out first, then nucleophilic reaction I. n-BuLi represents n-butyllithium, and t-BuLi represents tert-butyllithium.

[0272] The specific preparation method of the compound of the present invention will be described in detail below using a plurality of synthesis examples as examples, but the preparation method of the present invention is not limited to these synthesis examples.

[0273] It should be noted that obtaining the compound is not limited to the synthesis method and raw materials used in the present invention, and those skilled in the art may also select other methods or routes to obtain the compound proposed in the present invention. The compounds of the synthesis method not mentioned in the present invention are raw materials obtained from commercial channels, or are prepared by these raw materials according to known methods.

[0274] The analysis and detection of the intermediates and target products in the following synthetic examples of the present invention uses a high-resolution mass spectrometer and adopts matrix-assisted laser desorption ionization (MALDI) technology.

[0275] Synthesis Example 1: Synthesis of Compound M003

[0276] (1) Synthesis of intermediate M003-1

[0277]

[0278] Weigh 1,4-dibromo-2,6-difluorobenzene (6.0 g, 1.0 eq), 3,6-diphenylcarbazole (3.52 g, 0.5 eq), cesium carbonate (7.19 g, 1.0 eq) and place in a 500 mL three-necked round-bottom flask, add 80 mL N,N-dimethylformamide (DMF), and heat to 40 ° C for 24 h under nitrogen atmosphere. The reaction progress was monitored by thin layer chromatography (TLC) during the reaction. After the reaction was completed, the reaction system was allowed to stand and cool, and a large amount of water was added to the reaction system under stirring to precipitate solids, which were filtered and the filter cake was washed with water and ethanol. After the filter cake was dried, dichloromethane was added to dissolve the silica gel load, and silica gel column chromatography was performed to obtain the intermediate M003-1.

[0279] (2) Synthesis of intermediate M003-2

[0280]

[0281] Weigh M003-1 (6.2 g, 1.0 eq), 5-phenyl-5,8-dihydroindole [2,3-C] carbazole (3.72 g, 1.03 eq), cesium carbonate (8.84 g, 2.5 eq) and place in a 500 mL three-necked round-bottom flask, add 100 mL DMF, and heat to 100 ° C under nitrogen atmosphere for 16 h. The reaction progress was monitored by thin layer chromatography during the reaction. After the reaction was completed, the reaction system was allowed to stand and cool, and a large amount of water was added to the reaction system under stirring to precipitate solids, which were filtered and washed with water and ethanol. After the filter cake was dried, dichloromethane was added to dissolve the silica gel load, and silica gel column chromatography was performed to obtain the intermediate M003-2.

[0282] (3) Synthesis of intermediate M003-3

[0283]

[0284] Weigh M003-2 (8.0 g, 1.0 eq) and place it in a 500 mL three-necked round-bottom flask, add 80 mL of anhydrous xylene, and under a nitrogen atmosphere, cool it to below -30 ° C through a liquid nitrogen-ethanol mixed solution, slowly add 2.5 M n-butyl lithium solution (7.2 mL, 2.0 eq), slowly return the temperature of the reaction system to room temperature, and heat it at 60 ° C for 2 hours. Cool it to below -30 ° C through a liquid nitrogen-ethanol mixed solution again, add boron tribromide (2.2 mL, 2.5 eq), slowly return the temperature of the reaction system to room temperature, and heat it at 60 ° C for 1 hour. Cool it to below -0 ° C through a liquid nitrogen-ethanol mixed solution again, add N, N-diisopropylethylamine (6.0 mL, 4.0 eq), slowly return the temperature of the reaction system to room temperature, and heat it at 100 ° C for 5 hours. After the reaction is completed, the mixture is allowed to stand and cool, and most of the xylene is removed by distillation under reduced pressure. The residual mixture is subjected to silica gel column chromatography to obtain a crude product, and the crude product is further subjected to column chromatography and recrystallization to obtain M003-3.

[0285] (4) Synthesis of Compound M003

[0286]

[0287] Weigh M003-3 (1.5 g, 1.0 eq), (10-phenylanthracene-9-yl)boric acid (0.83 g, 1.5 eq), tetrakistriphenylphosphine palladium Pd(PPh3)4 (0.11 g, 0.05 eq), potassium carbonate (0.64 g, 2.5 eq) and place in a 500 mL three-necked round-bottom flask, add 20 mL 1,4-dioxane and 5 mL water, and heat to reflux under nitrogen atmosphere. The reaction progress was monitored by thin layer chromatography during the reaction. After the reaction was completed, it was allowed to stand and cool, and most of the solvent was removed by rotary evaporation under reduced pressure. Dichloromethane was added to dissolve, washed three times with water, and the organic phase was dried over anhydrous sodium sulfate and then loaded on silica gel, and the target compound M003 was obtained by silica gel column chromatography. The target molecular mass detected by high-resolution mass spectrometry was 985.3577 (theoretical value: 985.36).

[0288] Synthesis Example 2: Synthesis of Compound M004

[0289] The synthesis of compound M004 is similar to that of M003, except that 3,6-diphenylcarbazole is replaced with an equimolar equivalent of 3,6-di-tert-butylcarbazole, and the other raw materials, synthesis steps and processes are the same to obtain compound M004. The target molecular mass detected by high-resolution mass spectrometry is 945.294 (theoretical value: 945.43).

[0290] Synthesis Example 3: Synthesis of Compound M054

[0291] The synthesis of compound M004 is similar to that of M004, except that (10-phenylanthracene-9-yl)boronic acid is replaced by an equimolar equivalent of 10-(2-(3,5-di-tert-butylphenyl))phenylanthracene-9-boronic acid, and the other raw materials, synthesis steps and processes are the same to obtain compound M054. High-resolution mass spectrometry detected the target molecular mass: 1133.546 (theoretical value: 1133.58).

[0292] Theoretical calculation:

[0293] In the present invention, the theoretical calculation of the compound is completed by Gaussian 16 program, and the ground state structure of the molecule is optimized by 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 are optimized by TD-B3LYP / 6-31G* method, and the excitation energies in the ground state and excited state configurations correspond to the absorption (λabs, nm) and emission spectra (λem, nm) of the molecule, respectively (toluene is used as solvent, PCM solvent model); ΔE ST is the energy level 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.

[0294] The structures of the comparative compounds Ref-1, Ref-2, Ref-3, and Ref-4 are as follows:

[0295]

[0296] Table 1

[0297]

[0298] It can be seen from Table 1 that compared with Ref-1 emitting blue-green light, the compound provided by the present invention is a more suitable green light emitting material;

[0299] 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 condensed ring containing the boron atom, while the LUMO energy level is distributed on the substituted anthracene, showing the property of intramolecular charge transfer, and it is impossible to obtain a luminescent material with a narrow half-peak width and high fluorescence quantum efficiency;

[0300] Ref-3 increases the conjugated nature of the molecule by fusing the benzene rings, and the corresponding LUMO energy level and triplet energy level are both reduced, and the light color is red-shifted, which also leads to spectrum broadening. At the same time, the connection site of the substituent anthracene here is carbon No. 2, and there is no substitution on the 9th and 10th carbon atoms, while the 9th and 10th positions of anthracene are relatively active and easily oxidized or reduced. Therefore, when Ref-3 is used for electroluminescent materials, its stability is poor. In the compound provided by the present invention, the 9th and 10th positions of the substituent anthracene are both substituted, which significantly enhances its stability under electroluminescence.

[0301] Compared with Ref-4, the T1 energy level of the compound provided by the present invention is significantly reduced after the anthracene substituent is introduced, and ΔE ST The energy level of the compound provided by the present invention is significantly increased. Compared with the slower reverse intersystem crossing and long delayed fluorescence lifetime of the Ref-4 type multi-resonance materials, the lower T1 energy level of the compound provided by the present invention can inhibit the occurrence of this process, thereby improving the efficiency roll-off and lifetime decay in the device. In summary, the compound provided by the present invention not only maintains the narrow spectrum and high efficiency properties of the multi-resonance materials, but also reduces the T1 energy level of the molecule by introducing anthracene groups. It is used as a green light emitting material in an electroluminescent device, which is beneficial to improve the efficiency roll-off and lifetime decay in the device.

[0302] The compound of the present invention is used in a light-emitting device and can be used as a doping material for a light-emitting layer. The compound prepared in the above embodiment of the present invention is tested for fluorescence emission spectrum using a Hitachi F-4600 fluorescence spectrophotometer in a toluene solution. The test concentration is 10 -5 mol / L, S1 and T1 are calculated from the maximum emission wavelengths of the fluorescence spectrum and phosphorescence spectrum tested at 77K, respectively. The test results are shown in Table 2:

[0303] Table 2

[0304] Compound λem(nm) FWHM(nm) <![CDATA[S1(eV)]]> <![CDATA[T1(eV)]]> Ref-1 496 30 2.50 / Ref-4 512 21 2.41 2.17 M003 524 22 2.35 / M004 516 22 2.40 /

[0305] As can be seen from Table 2, compared with Ref-1, the compounds M003 and M004 provided by the present invention are more suitable green light emitting materials, and their narrow half-peak width is conducive to obtaining better color purity and higher efficiency in the device. Compared with Ref-4, which has a higher T1 energy level, the T1 energy levels of the compounds M003 and M004 provided by the present invention were not detected under the test conditions, indicating that the T1 energy levels of this type of compounds fall on the anthracene group, and the T1 energy is significantly reduced, ΔE ST The efficiency roll-off and lifetime decay caused by long-lived high-energy excited triplet states are significantly increased.

[0306] Device Embodiment

[0307] 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) which are stacked in sequence. The preparation method of the organic electroluminescent device is as follows:

[0308] (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;

[0309] (2) Place the glass substrate with the anode in a vacuum chamber and evacuate the chamber to a vacuum of 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 film thickness of 10 nm;

[0310] (3) vacuum evaporating compound HT-4 on the hole injection layer as a hole transport layer, with a total evaporation film thickness of 60 nm;

[0311] (4) vacuum evaporating compound HT-40 on the hole transport layer as an electron blocking layer, with a total film thickness of 5 nm;

[0312] (5) vacuum evaporating a light-emitting layer on the electron blocking layer, wherein the light-emitting layer includes a main material, a sensitizer and a doping material (fluorescent dye), and the doping ratio is adjusted by adjusting the evaporation rate of each material by using a multi-source co-evaporation method, and the total evaporation film thickness is 40 nm;

[0313] Wherein, when phosphorescence sensitized luminescence technology is adopted, the ratio of the main material, the phosphorescence sensitizer, and the 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 GPD1 or GPD-28, and the doping material is the compound provided by the present invention;

[0314] (6) vacuum evaporating compound ET-23 on the light-emitting layer as a hole blocking layer, with a total film thickness of 5 nm;

[0315] (7) vacuum evaporating 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 evaporation film thickness of 25 nm;

[0316] (8) Vacuum evaporation of LiF on the electron transport layer as an electron injection layer with a thickness of 1 nm;

[0317] (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.

[0318] The device examples in the following specific embodiments of the present invention all adopt the aforementioned hierarchical structure, materials and preparation methods, and the only difference is the light-emitting layer.

[0319] Device Examples 1-8

[0320] An organic electroluminescent device, wherein the light-emitting layer adopts phosphorescence sensitization luminescence technology, the ratio of the main material, the phosphorescence sensitizer, and the 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-28, and the doping materials are the compounds provided by the present invention, as shown in Table 3.

[0321] Comparative Example 1-2

[0322] An organic electroluminescent device, the light-emitting layer adopts phosphorescence sensitized light-emitting technology, and the only difference between the device embodiment 1 is that the doping material M003 is replaced by Ref-3 and Ref-4.

[0323] Device Examples 9-13

[0324] An organic electroluminescent device, wherein the light-emitting layer adopts phosphorescence sensitization luminescence technology, the ratio of the main material, the phosphorescence sensitizer, and the 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-1, and the doping materials are the compounds provided by the present invention, as shown in Table 4.

[0325] Comparative Examples 3-4

[0326] An organic electroluminescent device, the light-emitting layer adopts phosphorescence sensitized light-emitting technology, and the only difference between the device embodiment 9 is that the doping material M207 is replaced by Ref-1 and Ref-2.

[0327] Device performance test:

[0328] (1) Use a digital source meter and a PR650 spectroradiometer to measure the driving voltage, luminescence 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 2 The voltage at this time is the driving voltage, and the external quantum efficiency (EQE, %) is measured at the same time;

[0329] The life test of LT95 is as follows: Use a luminance meter at 10000cd / m 2 At the same brightness, the current is kept constant and the brightness of the organic electroluminescent device is measured to drop to 9500cd / m 2 The time in h.

[0330] The test value of the LT95 lifetime of device embodiment 1 is recorded as 1.00, and the LT95 lifetimes of device embodiments 2-8 and comparative examples 1-2 are all ratios of their respective test values ​​to the test value of device embodiment 1 (relative lifetime); the test value of the LT95 lifetime of device embodiment 9 is recorded as 1.00, and the LT95 lifetimes of device embodiments 10-13 and comparative examples 3-4 are all ratios of their respective test values ​​to the test value of device embodiment 9 (relative lifetime).

[0331] The test results are shown in Table 3 and Table 4:

[0332] Table 3

[0333]

[0334]

[0335] Table 4

[0336] Part Number Doping materials Driving voltage(V) EQE(%) LT95 Device Example 9 M207 4.1 14.00 1.00 Device Example 10 M001 4.0 14.10 1.03 Device Example 11 M004 4.0 14.50 1.09 Device Example 12 M252 4.1 14.30 0.94 Device Example 13 M266 4.0 13.80 0.96 Comparative Example 3 Ref-1 4.2 12.60 0.75 Comparative Example 4 Ref-2 4.3 8.50 0.42

[0337] Combined with the performance data of Table 3, it can be seen that the compounds of the present invention are used as fluorescent doping materials and are suitable for phosphorescence sensitized luminescence technology. Compared with Ref-3, the life of the devices prepared by the compounds of the present invention are improved, which can be mainly attributed to the better stability of the material under electroluminescence after the 9-position or 10-position substitution of anthracene. Compared with Ref-4, the devices prepared by the compounds of the present invention have a longer life, which can be mainly attributed to the fact that after the introduction of 9-phenylanthracene, the T1 energy level of the molecule can be significantly reduced, improving the device attenuation caused by the triplet excitons with longer life and higher energy in the device due to the multi-resonance material.

[0338] In Table 4, the emission wavelength of Ref-1 is blue-shifted compared with the compound of the present invention, so when Ref-1 is sensitized with GPD-1, the energy transfer is incomplete, resulting in reduced device efficiency. Since the LUMO energy level of Ref-2 is deep in the 9-phenylanthracene structure, the molecule exhibits intramolecular charge transfer properties, and thus the device exhibits a wide emission spectrum and low device efficiency.

[0339] The above results show that the novel compound of the present invention is used in organic electroluminescent devices, has narrow green light emission, significantly increases the device life, improves the luminous efficiency, and is a fluorescent dopant for the light-emitting layer with good performance.

[0340] The applicant declares that the present invention uses the above-mentioned embodiments to illustrate the compounds of the present invention and their applications, and the organic electroluminescent devices containing the compounds of the present invention, but the present invention is not limited to the above-mentioned embodiments, that is, it does not mean that the present invention must rely on the above-mentioned embodiments to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A compound, characterized in that The compound has a structure as shown in Formula I: Wherein, Y is selected from O, S, Se, NAr 1 , CR 1 R 2 or SiR 3 R 4 Any of the following: Ar 1 Any one selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; Ar 1 Not connected to adjacent ring structures or connected to form a ring through chemical bonds; R 1 , R 2 , R 3 , R 4 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 C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; the R 1 With R 2 are not connected or connected to form a ring through chemical bonds, the R 3 With R 4 They are not connected to each other or connected to form a ring through chemical bonds; X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 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; The X 4 With X 5 are not connected or connected to form a ring through chemical bonds, the X 9 With Z 1 There is no connection between them; 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 alkylamino, substituted or unsubstituted C1-C20 alkylsilyl, cyano, nitro, 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-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 Cy1, wherein the ring Cy1 is selected from any one of a substituted or unsubstituted C6-C60 aromatic ring and a substituted or unsubstituted C5-C60 heteroaromatic ring; The R A1 , R A2 , R A3 In the above, the other groups except those forming the ring Cy1 are independently not connected to the adjacent ring structure or are connected to form a ring through chemical bonds; Ar 1 , R 1 , R 2 , R 3 , R 4 , R A1 , R A2 , R A3 The substituents substituted in the ring Cy1 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 C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R'substituted C6 -C30 arylsilyl, 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 them is a group R X , and / or, the Ar 1 , R 1 , R 2 , R 3 , R 4 At least one of them is a group R X ; The R X It has the structure shown in formula a: Among them, Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q 10 Each independently selected from C, CR 11 or N, and one of them is C, and the C is R X The attachment site of R 11 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 C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C6-C30 aryloxy, unsubstituted or R'substituted C6-C30 arylamino, unsubstituted or R'substituted C6-C30 arylsilyl, unsubstituted or R'substituted C6-C60 aryl, and unsubstituted or R'substituted C3-C60 heteroaryl; the R 11 Not all hydrogen; 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 compound according to claim 1, characterized in that The X 4 With X 5 The compounds are connected to form a ring through a chemical bond Y', and the compound has a structure as shown in Formula II: Among them, Y, X 1 , X 2 , X 3 , X 6 , X 7 , X 8 , X 9 , Y 1 , Y 2 , Y 3 , Y 4 , Z 1 , Z 2 , Z 3 Having the same definition as in Formula I; The Y' is selected from a single bond, O, S, Se, NAr 2 , CR 5 R 6 or SiR 7 R 8 Any of the following: Ar 2 Any one selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group; R 5 , R 6 , R 7 , R 8 are 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 alkylsilyl, cyano, nitro, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; said R 5 With R 6 are not connected or connected to form a ring through chemical bonds, the R 7 With R 8 They are not connected to each other or connected to form a ring through chemical bonds; Ar 2 , R 5 , R 6 , R 7 , R 8 The substituents substituted in the above-mentioned substitution 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 C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R'substituted C6-C The substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring by chemical bonds.

3. The compound according to claim 2, characterized in that The Y is NAr 1 ; Preferably, the X 4 With X 5 They are connected to form a ring by single bonds; Preferably, the compound has a structure as shown in Formula III: Among them, X 1 , X 2 , X 3 , X 6 , X 7 , X 8 , X 9 , Y 1 , Y 2 , Y 3 , Y 4 , Z 1 , Z 2 , Z 3 ,Ar 1 The scope of the invention is the same as that of claim 1.

4. The compound according to claim 1, characterized in that Any two adjacent R A1 Any two adjacent R A2 Any two adjacent R A3 At least one group of them is connected by chemical bonds to form a ring Cy1, and the ring Cy1 has a structure as shown in formula b: Among them, the dotted lines represent fused bonds; X 11 , X 12 , X 13 , X 14 Each independently selected from CR B1 or N; M1 and M2 are each independently selected from a single bond, O, S, NAr 3 or CR M1 R M2 Any one of; at most one of M1 and M2 is a single bond; Ar 3 Any one selected from unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; R B1 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 C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R'-substituted C6-C30 arylsilyl, 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 B1 Each independently is not connected to the adjacent ring structure or is connected to form a ring through a chemical bond; 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 C6-C60 aryl, and unsubstituted or R'substituted C3-C60 heteroaryl; the R M1 With R M2 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 3 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 At most four groups in are connected by chemical bonds to form a ring Cy1; Preferably, any two adjacent R A1 A group of them are connected by chemical bonds to form a ring Cy1; and / or any two adjacent R A2 One group of them is connected by chemical bonds to form a ring Cy1; Preferably, any two adjacent R A1 Any two adjacent R A2 Any two adjacent R A3 A group of them are connected by chemical bonds to form a ring Cy1.

5. The compound according to claim 4, characterized in that The compound has a structure as shown in any one of Formula IV-1 to Formula IV-13: Wherein, M1 is selected from O, S, NAr 3 or CR M1 R M2 Any of the following: X 11 , X 12 , X 13 , X 14 ,Ar 3 , R B1 , R M1 , R M2 Having the same limited range as in formula b; X 1 , X 2 , X 3 , X 6 , X 7 , X 8 , X 9 , Y 1 , Y 2 , Y 3 , Y 4 , Z 1 , Z 2 , Z 3 ,Ar 1 Having the same definition as in claim 1; Preferably, the compound has a structure as shown in any one of Formula IV-1, Formula IV-2, Formula IV-3, Formula IV-7, Formula IV-8, Formula IV-12, and Formula IV-13; Preferably, the compound has a structure as shown in any one of Formula IV-1 to Formula IV-3.

6. The compound according to claim 5, characterized in that The compound has a structure as shown in any one of Formula V-1 to Formula V-13: Among them, the dashed line represents a single bond or no connection; X 1 , X 2 , X 3 , X 6 , X 7 , X 8 , X 9 , Y 1 , Y 2 , Y 3 , Y 4 , Z 1 , Z 2 , Z 3 , M1, X 11 , X 12 , X 13 , X 14 Having the same definition as in claim 5; Y 5 , Y 6 , Y 7 , Y 8 , Y 9 Each independently selected from CR C1 or N; R C1 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 C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R'-substituted C6-C30 arylsilyl, 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 C1 Each independently is not connected to the adjacent ring structure or is connected to form a ring through a chemical bond; Preferably, the 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, V-12, and V-13, and further preferably has a structure as shown in any one of Formula V-1, Formula V-2, and Formula V-3.

7. The compound according to claim 6, characterized in that The X 6 , X 7 , X 8 , 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, X 7 , X 8 , Y 2 , Y 3 , Y 5 , Y 7 , Y 9 , Z 2 At least one of them is CR X ; Preferably, the Y 2 , Y 3 , Y 5 , Y 7 , Y 9 and Z 2 At least one of them is CR X .

8. The compound according to claim 6, characterized in that The X 1 , X 2 , X 3 , X 6 , X 7 , X 8 , X 9 Each independently is CR A1 ; Preferably, the R A1 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 , X 3 , X 6 , X 7 , X 8 and X 9 All are CH; Preferably, the X 11 , X 12 , X 13 , X 14 Each independently is CR B1 ; Preferably, the X 11 , X 12 , X 13 and X 14 All are CH; Preferably, the Y 1 , Y 2 , Y 3 , Y 4 Each independently is CR A2 ; Preferably, the Y 1 , Y 2 , Y 3 , Y 4 The number of CH in the medium is 1-4; Preferably, the Y 1 and Y 4 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, and substituted or unsubstituted C3-C60 heteroaryl; Preferably, the Y 5 , Y 6 , Y 7 , Y 8 , Y 9 Each independently is CR C1 ; Preferably, the Y 5 , Y 6 , Y 7 , Y 8 , Y 9 The number of CH in the medium is 2-5; Preferably, when the dashed line in Formula V-1 to Formula V-9 represents absence, the Y 5 , Y 7 , Y 9 One of them is CR C1 Or, when the dotted line in Formula V-1 to Formula V-9 represents a single bond, the Y 7 , Y 8 One of them is CR C1 ; Preferably, in Formula V-10 to Formula V-13, the Y 5 , Y 7 , Y 9 One of them is CR C1 ; Preferably, the R C1 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 C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C6-C30 arylamino, unsubstituted or R'substituted C6-C60 aryl, and unsubstituted or R'substituted 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 Selected from 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 C6-C60 aryl.

9. The compound according to claim 1, characterized in that The compound has a structure as shown in any one of Formula VI-1 to Formula VI-10: Wherein, M1 is selected from O, S, NAr 3 or CR M1 R M2 Any of the following: Ar 3 Any one selected from unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl; 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 C6-C60 aryl, and unsubstituted or R'substituted C3-C60 heteroaryl; the 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 C1 Each independently represents no substitution, monosubstitution to the maximum allowed substitution; R A2 , R A3 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 alkylsilyl, 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 Each independently is not connected to the adjacent ring structure or is connected to form a ring through a chemical bond; R C1 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 C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R'-substituted C6-C30 arylsilyl, 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 C1 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 C1 At least one of them is a group R X .

10. The compound according to any one of claims 1 to 9, characterized in that The R X It has the structure shown in formula c: Wherein, -* represents the attachment site of the group; R 11 represents mono-substitution to the maximum allowed substitution; R 11 Each is independently selected from any one of an unsubstituted or R'-substituted C1-C20 straight or branched alkyl group, an unsubstituted or R'-substituted C3-C20 cycloalkyl group, an unsubstituted or R'-substituted C2-C20 alkenyl group, an unsubstituted or R'-substituted C1-C20 alkylsilyl group, an unsubstituted or R'-substituted C6-C30 aryloxy group, an unsubstituted or R'-substituted C6-C30 arylamino group, an unsubstituted or R'-substituted C6-C30 arylsilyl group, an unsubstituted or R'-substituted C6-C60 aryl group, and an unsubstituted or R'-substituted C3-C60 heteroaryl group; Preferably, the R 11 The number of substitutions is 1-9, more preferably 1-3; Preferably, the R 11 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 11 Each is independently selected from any one of 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, and is further preferably any one of 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 X It has the structure shown in formula d: Among them, R 21 Any one selected from 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 aryloxy, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C6-C30 arylsilyl, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; R 22 , R 23 Each independently represents no substitution, monosubstitution to the maximum allowed substitution; R 22 , R 23 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 C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C6-C30 aryloxy, unsubstituted or R'substituted C6-C30 arylamino, unsubstituted or R'substituted C6-C30 arylsilyl, unsubstituted or R'substituted C6-C60 aryl, and unsubstituted or R'substituted C3-C60 heteroaryl, and is further preferably any one of hydrogen, C1-C5 straight or branched alkyl, unsubstituted or R'substituted C6-C20 aryl, and unsubstituted or R'substituted C3-C20 heteroaryl; Preferably, the R 21 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 aryloxy, unsubstituted or R'-substituted C6-C20 arylamino, 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, and unsubstituted or R'-substituted C6-C20 aryl; Preferably, the R 21 Any one selected from the following groups: -* represents the attachment site of the group.

11. The compound according to claim 9, characterized in that The R A2 are each independently 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-C12 aryl, substituted or unsubstituted C3-C20 heteroaryl; Preferably, the R A3 are each independently selected from hydrogen, R X , any one of substituted or unsubstituted C1-C10 straight or branched alkyl, and substituted or unsubstituted C6-C12 aryl; Preferably, the R C1 are each independently selected from hydrogen, R X , unsubstituted or R'-substituted C1-C10 straight or branched alkyl, unsubstituted or R'-substituted C3-C10 cycloalkyl, unsubstituted or R'-substituted C2-C10 alkenyl, unsubstituted or R'-substituted C1-C10 alkylsilyl, unsubstituted or R'-substituted C6-C20 arylamino, unsubstituted or R'-substituted C6-C12 aryl, unsubstituted or R'-substituted C3-C20 heteroaryl.

12. The compound according to claim 1, characterized in that The compound has a structure shown in any one of the following M001-M365:

13. Use of a compound according to any one of claims 1 to 12, characterized in that: The compound is used in organic electronic devices; Preferably, the organic electronic device comprises an organic electroluminescent device; Preferably, the compound is used as a light-emitting layer material in an organic electroluminescent device.

14. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises 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 compound according to any one of claims 1 to 12; Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one compound according to any one of claims 1 to 12; Preferably, the light-emitting layer comprises a host material and a doping material, and the doping material comprises at least one compound according to any one of claims 1 to 12; Preferably, the light-emitting layer further comprises a sensitizer; 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.

15. A display device, characterized in that: The display device comprises the organic electroluminescent device according to claim 14.

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