Organic compound and application thereof, and organic electroluminescent device containing organic compound

Abstract

The invention provides an organic compound and application thereof, and an organic electroluminescent device comprising the organic compound, the organic compound has a structure as shown in formula I. Through the design of a specific condensed ring mother nucleus structure, the organic compound keeps narrow emission spectrum and high luminous efficiency of a multi-resonance material, and the luminous efficiency of the multi-resonance material is improved. The purposes of adjusting light color and reducing the triplet state energy level of molecules are achieved, the inherent properties of delayed fluorescence with high triplet state energy level and long service life of a multiple resonance structure are improved, and efficiency roll-off and service life attenuation caused by relatively slow reverse intersystem crossing rate are inhibited. The organic compound has excellent electroluminescent performance and narrow spectrum characteristic, is good in stability, is used for an organic electroluminescent device, can be used as a fluorescent doping material of a luminescent layer, inhibits reverse intersystem crossing, and reduces the concentration of triplet excitons with long service life of a system, so that the service life roll-off of the device is improved, the luminous efficiency of the device is improved, and the service life of the device is prolonged. And device life is prolonged.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to an organic compound and application thereof, and an organic electroluminescent device containing the organic 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, platinum complexes, etc. Due to their generally low abundance, they are very expensive among many OLED materials. Therefore, reducing the amount of phosphorescent materials is 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 the research focus in this field. Summary of the invention

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

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

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

[0008]

[0009] In Formula I, the chemical bonds represented by a, b, c, d, e, f, g, i, j, and k represent condensable bonds.

[0010] In Formula I, at least one of the chemical bonds represented by a, b, c, d, and e is fused to the structure represented by Formula a, at least one of the chemical bonds represented by f and g is fused to the structure represented by Formula b, and at least one of the chemical bonds represented by i, j, and k is fused to the structure represented by Formula b.

[0011]

[0012] In formula a and formula b, the dotted line represents a fused bond.

[0013] In formula a, X is selected from O, S, CR 11 R 12 NR 13 or SiR 14 R 15 Any one of .

[0014] R 11 , R 12 , R 13 , R 14 , R 15 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 C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; the R 11 and R 12 are not connected or connected to form a ring through chemical bonds, the R 14 and R 15 They are not connected or connected to form a ring through chemical bonds.

[0015] In formula a, Y1, Y2, Y3, and Y4 are each independently selected from CR 5 or N; multiple (e.g. 2, 3, 4) CR 5 R 5 are the same or different groups.

[0016] In formula b, X1, X2, X3, and X4 are each independently selected from CR 6 or N; multiple (e.g. 2, 3, 4) CR 6 R 6 are the same or different groups.

[0017] In Formula I, Y 11 , Y 12 , Y 13 Each independently selected from CR 7 or N; multiple (e.g. 2, 3) CR 7 R 7 are the same or different groups.

[0018] In Formula I, R 1 , R 2 , R 3 , R 4 Each independently represents no substitution, monosubstitution to the maximum allowed substitution.

[0019] R 1 For example, when R 1 When it is hydrogen, it represents no substitution; R 1 The maximum permissible substitution is disubstitution; when R 1 When disubstituted, the two R 1 R 2 , R 3 , R 4 The same applies to the statements of , for the sake of brevity, I will not go into details one by one.

[0020] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7R 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 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 Each is independently not connected to the adjacent ring structure or connected to form a ring through a chemical bond.

[0021] 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-C30 arylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or a combination of at least two thereof; adjacent R's are not connected or are connected to form a ring by chemical bonds; the R' is not connected to adjacent ring structures or is connected to form a ring by chemical bonds.

[0022] In the present invention, "R' is not connected to the adjacent ring structure" means that R' is only connected to the C atom by a single bond; "R' is connected to the adjacent ring structure by a chemical bond to form a ring" means that R' is connected to the C atom by a chemical bond and is also connected to the adjacent ring by a chemical bond, thereby forming a fused ring structure. When the same description is involved below, they all have the same meaning and will not be repeated one by one.

[0023] 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.

[0024] The organic compound provided by the present invention has a molecular structure shown in formula I, and a six-membered ring (preferably a benzene ring) shown in formula b and a condensed ring structure (preferably a benzo five-membered ring) shown in formula a are fused on the carbazole boron nitrogen multiple resonance structure to form a specific condensed ring mother core structure, and a partially conjugated property is introduced in the multiple resonance structure. While adjusting the light color of the organic compound to green light or yellow light, the triplet energy level of the molecule can be effectively reduced, the singlet and triplet energy level difference is increased, the thermally activated delayed fluorescence property of the molecule is weakened or eliminated, and the efficiency roll-off and life decay caused by the high triplet energy level and slow reverse intersystem crossing of the multiple resonance thermally activated delayed fluorescence material are improved. Based on the special design of the aforementioned molecular structure, the conjugated property of the molecule is enhanced, so that the organic compound can achieve the purpose of light color adjustment and reducing the triplet energy level of the molecule while maintaining the narrow emission spectrum and high luminous efficiency of the multiple resonance material, and weaken or eliminate the property of the thermally activated delayed fluorescence of the molecule, and then suppress the efficiency roll-off and life decay caused by the slow reverse intersystem crossing rate. The organic compound has excellent electroluminescent performance and narrow spectrum characteristics, a narrow half-peak width of the emission spectrum and good stability. It is used in organic electroluminescent devices and can be used as a fluorescent doping material for the light-emitting layer to effectively improve the device's life roll-off, enhance the device's luminous efficiency, and extend the device's life.

[0025] 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.

[0026] 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.

[0027] In the present invention, the halogen may be fluorine, chlorine, bromine or iodine. The following descriptions involving the same have the same meaning.

[0028] 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) includes 12 C. 13 C, etc.

[0029] 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.

[0030] 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.

[0031] In the present invention, "-*" and "*" both represent the connection site of a group.

[0032] 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.

[0033] In the present invention, “each independently” means that when there are multiple subjects, they may be the same as or different from each other.

[0034] In the present invention, C1-C20 may be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0035] 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.

[0036] The C6-C60 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.

[0037] 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.

[0038] The C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0039] The C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0040] In the present invention, 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.

[0041] Specific examples of the C1-C20 alkoxy group include monovalent groups obtained by connecting the above-mentioned linear or branched alkyl groups to O.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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 adjacent aromatic rings. The carbon atoms of the groups are mutually fused, including, but 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.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] Preferably, in Formula I, it is fused to the structure represented by Formula a through one of the chemical bonds represented by a, b, c, d, and e.

[0051] Preferably, in Formula I, it is fused to the structure represented by Formula a via one of the chemical bonds represented by a and b, and more preferably, it is fused to the structure represented by Formula a via the chemical bond represented by b.

[0052] Preferably, in Formula I, it is fused to the structure shown in Formula b through one of the chemical bonds represented by f and g, and is fused to the structure shown in Formula b through one of the chemical bonds represented by i, j, and k.

[0053] Preferably, in Formula I, it is fused to the structure shown in Formula b through the chemical bond shown in f, and is fused to the structure shown in Formula b through one of the chemical bonds shown in i, j, and k.

[0054] Preferably, one of the chemical bonds represented by i and j is fused to the structure represented by formula b.

[0055] Further preferably, in Formula I, it is fused to the structure shown in Formula b via the chemical bond shown in f, and is fused to the structure shown in Formula b via the chemical bond shown in i.

[0056] Preferably, the organic compound has a structure as shown in any one of Formulas II-1 to II-3, wherein one of the chemical bonds shown in i, j, and k is fused with the structure shown in Formula b:

[0057]

[0058]

[0059] Wherein, X1, X2, X3, and X4 have the same defined ranges as in formula b; X, Y1, Y2, Y3, and Y4 have the same defined ranges as in formula a; Y 11 , Y 12 , Y 13 , R 1 , R 2 , R 3 , R 4 has the same definition as in Formula I.

[0060] Preferably, the organic compound has a structure as shown in any one of Formulas III-1 to III-24, and further preferably has a structure as shown in any one of Formulas III-1 to III-3:

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070] Wherein, X, Y1, Y2, Y3, and Y4 have the same defined ranges as in formula a.

[0071] Y 11 , Y 12 , Y 13 , R 1 , R 2 , R 3 , R 4 has the same definition as in Formula I.

[0072] X1, X2, X3, and X4 have the same defined ranges as in formula b.

[0073] X1', X2', X3', X4' are each independently selected from CR 6 or N; multiple (e.g. 2, 3, 4, 5, 6, 7, 8) CR 6 R 6 are the same or different groups.

[0074] R 6 Has the same definition as in formula b.

[0075] Preferably, at most one (0 or 1) of Y1, Y2, Y3 and Y4 is N.

[0076] Preferably, Y1, Y2, Y3, and Y4 are each independently CR 5 .

[0077] Preferably, the R 5Each is independently selected from any one of hydrogen, halogen, 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, cyano, unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, unsubstituted or R'-substituted C3-C20 heteroaryl (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.), and is more preferably hydrogen.

[0078] Preferably, Y1, Y2, Y3 and Y4 are all CH.

[0079] Preferably, at most one (0 or 1) of X1, X2, X3 and X4 is N; and / or at most one (0 or 1) of X1', X2', X3' and X4' is N.

[0080] Preferably, X1, X2, X3, X4, X1', X2', X3', X4' are each independently CR 6 .

[0081] Preferably, the R 6 Each is independently selected from any one of hydrogen, halogen, 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, cyano, unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, unsubstituted or R'-substituted C3-C20 heteroaryl (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.), and is more preferably hydrogen.

[0082] Preferably, X1, X2, X3, X4, X1', X2', X3' and X4' are all CH.

[0083] Preferably, the Y 11 , Y 12 and Y 13 There is at most 1 (0 or 1) in N.

[0084] Preferably, the Y 11 , Y 12 , Y 13 Each independently is CR 7 .

[0085] Preferably, the Y 11 , Y 12 and Y 13 The number of CH in is 1-3, for example, 1, 2 or 3.

[0086] Preferably, the Y 11 and Y 13 is CH, the Y 12 CR 7 ; or, said Y 12 is CH, the Y 11 and Y 13 At least one of them is CR 7 .

[0087] Preferably, the Y 11 and Y 13 is CH, the Y 12 CR 7 .

[0088] Preferably, the R 7 Each is independently selected from any one of hydrogen, halogen, cyano, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, 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, halogen, cyano, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C6-C30 arylamino, unsubstituted or R'substituted C6-C60 aryl, and unsubstituted or R'substituted C3-C60 heteroaryl. C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl, unsubstituted or R'-substituted C3-C10 cycloalkyl (e.g., C4, C5, C6, C7, C8, C9, etc.), unsubstituted or R'-substituted C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22 any one of an unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl group, and an unsubstituted or R'-substituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl group, more preferably Further preferred are hydrogen, unsubstituted or R'-substituted groups: C1-C6 straight or branched alkyl, diphenylamino, phenyl, naphthyl, biphenyl, terphenyl, pyridyl, pyrimidyl, phenylpyridyl, phenylpyrimidyl, diphenylpyridyl, diphenylpyrimidyl, phenylnaphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, fluorenyl, and dimethylfluorenyl.

[0089] Preferably, the R' is independently selected from any one or a combination of at least two of halogen, cyano, C1-C20 straight or branched alkyl, C2-C20 alkenyl, C6-C30 aryl, and C3-C30 heteroaryl, and more preferably halogen, cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, C Any one of C6-C20 (for example, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, C3-C20 (for example, C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl or a combination of at least two thereof, and any one of fluorine, cyano, methyl, perfluoromethyl, isopropyl, isobutyl (2-methylpropyl), tert-butyl, tert-amyl, phenyl and carbazolyl is further preferred.

[0090] Preferably, the R' is not connected to the adjacent ring structure or is connected to form a ring Cy through a chemical bond.

[0091] Preferably, the ring Cy is 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 Cy.

[0092] Preferably, the organic compound has a structure as shown in any one of Formula IV-1 to Formula IV-24:

[0093]

[0094]

[0095]

[0096]

[0097] Among them, R 7 represents no substitution, mono-substitution to the maximum permissible substitution. 7 Indicates no substitution (R 7 is hydrogen), monosubstituted, disubstituted or trisubstituted; when R 7 When it indicates di- or tri-substitution, multiple R 7are the same or different groups. 7 It represents unsubstituted, monosubstituted or disubstituted.

[0098] X and R 7 The same species definitions as in Formula I are present.

[0099] Preferably, X is selected from O, S, CR 11 R 12 NR 13 Any one of the above, preferably CR 11 R 12 or NR 13 Any one of the above, preferably NR 13 .

[0100] Preferably, the R 13 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 C6-C30 aryl, unsubstituted or R'-substituted C3-C30 heteroaryl, further preferably any one of C1-C10 (e.g. C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, C6-C20 aryl (e.g. C6, C9, C10, C12, C14, C15, C16 or C18, etc.), further preferably phenyl.

[0101] Preferably, the R 7 It represents no substitution (hydrogen) or monosubstitution.

[0102] Preferably, the R 7 Indicates single substitution.

[0103] Preferably, the R 7any one selected from hydrogen, cyano, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C6-C30 arylamino, unsubstituted or R'substituted C6-C60 aryl, unsubstituted or R'substituted C3-C60 heteroaryl, 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.) any one of an unsubstituted or R'-substituted C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26 or C28, 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., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl.

[0104] Preferably, the R 7 Any one of the following groups selected from hydrogen, unsubstituted or R'substituted: C1-C5 straight or branched alkyl, C6-C10 cycloalkyl, -* represents the attachment site of the group.

[0105] Z is selected from O, S, CR 21 R 22 or NR 23 Any of the following:

[0106] R 21 , R 22 , R 23 Each is independently selected from any one or a combination of at least two of a C1-C20 straight or branched alkyl group, a C3-C20 cycloalkyl group, a C2-C20 alkenyl group, a C6-C30 aryl group, and a C3-C30 heteroaryl group; 21 and R 22 Not connected or connected to form a ring through chemical bonds.

[0107] Preferably, the R 21 , R 22 , R 23Each is independently selected from any one of C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight chain or branched alkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, further preferably any one of C1-C6 straight chain or branched alkyl, phenyl, naphthyl, biphenyl, further preferably methyl or phenyl.

[0108] Preferably, the R' is independently selected from any one or a combination of at least two of halogen, cyano, C1-C20 straight or branched alkyl, C2-C20 alkenyl, C6-C30 aryl, C3-C30 heteroaryl; adjacent R' are not connected or are connected to form a ring through chemical bonds; the R' is not connected to the adjacent ring structure or is connected to form a ring through chemical bonds.

[0109] Preferably, each of the R's is independently selected from halogen, cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, C2-C10 (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.) 1-C5 straight or branched alkyl, C6-C20 aryl, C3-C20 heteroaryl or any combination of at least two thereof; preferably fluorine, cyano, C1-C5 straight or branched alkyl, C6-C20 aryl, C3-C20 heteroaryl or any combination of at least two thereof; further preferably fluorine, cyano, methyl, perfluoromethyl, ethyl, Any one or a combination of at least two of the following; -* represents the connection site of the group.

[0110] Preferably, the R 7 are each independently selected from hydrogen, methyl,

[0111]

[0112] Any of the above, -* represents the attachment site of the group.

[0113] Preferably, the organic compound has a structure shown in any one of the following M001-M472:

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139] In a second aspect, the present invention provides a use of the organic compound as described in the first aspect, wherein the organic compound is applied to an organic electronic device.

[0140] 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.

[0141] Preferably, the organic compound is applied to an organic electroluminescent device.

[0142] Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device.

[0143] Preferably, all organic compounds are used as dyes (also known as "doping materials", "dopants", "guest materials") of the light-emitting layer in organic electroluminescent devices.

[0144] 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 organic compound as described in the first aspect.

[0145] Preferably, the organic layer comprises at least one organic compound having a structure shown in M001-M472.

[0146] Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one organic compound as described in the first aspect, preferably comprises at least one organic compound with a structure shown as M001-M472.

[0147] Preferably, the light-emitting layer comprises a host material and a doping material (also known as "dopant", "dye", "guest material"), and the doping material comprises at least one organic compound as described in the first aspect.

[0148] Preferably, the organic compound provided by the present invention is used as a fluorescent doping material for a light-emitting layer.

[0149] 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%.

[0150] 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.

[0151] Preferably, the light-emitting layer further comprises a sensitizer.

[0152] 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.

[0153] Preferably, the maximum emission wavelength of the sensitizer is less than the maximum emission wavelength of the organic compound of the present invention.

[0154] 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.

[0155] Preferably, the sensitizer comprises a phosphorescent material, and the mass percentage of the phosphorescent material in the light-emitting layer is 0.1-10%.

[0156] 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%.

[0157] Preferably, the organic layer further includes a hole transport region and an electron transport region.

[0158] 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.

[0159] 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.

[0160] In a preferred technical solution, the organic electroluminescent device (OLED device) comprises a first electrode, a second electrode, and an organic layer 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 organic compound as described in the first aspect, and further preferably comprises at least one organic compound having a structure shown in M001-M472.

[0161] 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 organic compound as described in the first aspect, and further preferably comprises at least one organic compound having a structure shown in M001-M472.

[0162] 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.

[0163] 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.

[0164] 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.

[0165] 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.

[0166] 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.

[0167]

[0168]

[0169]

[0170] 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.

[0171]

[0172] 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.

[0173] 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.

[0174]

[0175]

[0176]

[0177]

[0178] 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.

[0179]

[0180]

[0181]

[0182] Where D is deuterium.

[0183] 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.

[0184] 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.

[0185]

[0186]

[0187]

[0188] 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.

[0189] 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.

[0190] 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.

[0191] 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).

[0192] 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.

[0193]

[0194]

[0195]

[0196]

[0197] 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.

[0198] 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.

[0199] In a fourth aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the third aspect.

[0200] Preferably, the display device includes a display screen or a display panel.

[0201] The present invention also provides an electronic device, which includes the above-mentioned display device.

[0202] Compared with the prior art, the present invention has the following beneficial effects:

[0203] In the organic compound provided by the present invention, by designing a specific fused ring mother core structure, while maintaining the narrow emission spectrum and high luminous efficiency of the multiple resonance material, the purpose of light color regulation and reducing the triplet energy level of the molecule is achieved, the high triplet energy level inherent in the multiple resonance structure and the long-life delayed fluorescence properties are improved, and the efficiency roll-off and life decay caused by the slow reverse intersystem crossing rate are suppressed. The organic compound has excellent electroluminescent performance and narrow spectrum characteristics, the half-peak width of the emission spectrum is narrow, and the stability is good. It is used in organic electroluminescent devices, and can be used as a fluorescent doping material for the light-emitting layer, suppressing reverse intersystem crossing, and reducing the concentration of the triplet excitons with a long life of the system, thereby effectively improving the life roll-off of the device, improving the luminous efficiency of the device, and extending the device life. DETAILED DESCRIPTION

[0204] 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.

[0205] The organic 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.

[0206] In a specific embodiment, the organic compound can be prepared by the following synthetic route 1:

[0207]

[0208] Among them, Y 11 , Y 12 , Y 13 , R 1 , R 2 , R 3 , R 4 , a, b, c, d, e, f, g, i, j, and k have the same limited range as that of formula I; Hal1 is independently selected from I, Br or Cl; the order of nucleophilic reaction I and nucleophilic reaction II can be adjusted according to the synthesis situation, that is, nucleophilic reaction I can be carried out first and then nucleophilic reaction II, or nucleophilic reaction II can be carried out first and then nucleophilic reaction I.

[0209] In a specific embodiment, the organic compound can be prepared by the following synthetic route 2:

[0210]

[0211] Among them, Y 11 , Y 12 , Y13 , R 1 , R 2 , R 3 , R 4 , a, b, c, d, e, f, g, i, j, k have the same limited range as Formula I; Hal1 and Hal2 are independently selected from I, Br or Cl; in this case, the substituent R7 in Formula I is an aryl or heteroaryl group, and R7 is obtained by coupling reaction I with Hal2. The order of coupling reaction I and the final cyclization reaction can be adjusted according to the synthesis situation. When the cyclization reaction is performed first, the atomic number of Hal2 is required to be less than or equal to Hal1. The order of nucleophilic reaction I and nucleophilic reaction II can be adjusted according to the synthesis situation, that is, nucleophilic reaction I can be performed first, then nucleophilic reaction II, or nucleophilic reaction II can be performed first, then nucleophilic reaction I. When the substituent R7 is not hydrogen, coupling reaction I is the substituent represented by Hal2 and R7.

[0212] The specific preparation method of the organic compound of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the preparation method of the present invention is not limited to these synthesis examples.

[0213] It should be noted that the organic 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 organic 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.

[0214] The analysis and detection of the intermediates and target products in the following synthetic examples of the present invention were performed using a high-resolution mass spectrometer.

[0215] Synthesis Example 1: Synthesis of Organic Compound M093

[0216] (1) Synthesis of intermediate M093-1

[0217]

[0218] Weigh 1-bromo-2,6-difluorobenzene (5.0 g, 1.0 eq), 7H-dibenzocarbazole (3.46 g, 0.5 eq), cesium carbonate (8.44 g, 1.0 eq) and place in a 500 mL three-necked round-bottom flask, add 80 mL N, N-dimethylformamide, and heat to 40 ° C under nitrogen atmosphere for 12 h. The reaction progress was monitored by thin layer chromatography (TLC). After the reaction was completed, it was allowed to stand and cool, and the reaction system was added to a large amount of water under stirring, and the solid was precipitated, 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 the target compound M093-1 was obtained by silica gel column chromatography.

[0219] (2) Synthesis of intermediate M093-2

[0220]

[0221] Weigh M093-1 (5.5 g, 1.0 eq), 5-phenyl-5,8-dihydroindole [2,3-C] carbazole (4.28 g, 1.03 eq), cesium carbonate (10.17 g, 2.5 eq) and place in a 500 mL three-necked round-bottom flask, add 100 mL N, N-dimethylformamide, 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, it was allowed to stand and cool, and the reaction system was added to a large amount of water under stirring, and the solid was precipitated, 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 the target compound M093-2 was obtained by silica gel column chromatography.

[0222] (3) Synthesis of target product M093

[0223]

[0224] Weigh M093-2 (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 (10.6 mL, 2.5 eq), slowly return the temperature of the reaction system to room temperature, and heat it at 60 ° C for 2 h. Cool it to below -30 ° C through a liquid nitrogen-ethanol mixed solution again, add boron tribromide (3.0 mL, 3.0 eq), slowly return the temperature of the reaction system to room temperature, and heat it at 60 ° C for 1 h. Cool it to below -0 ° C through a liquid nitrogen-ethanol mixed solution again, add N, N-diisopropylethylamine (7.9 mL, 4.5 eq), slowly return the temperature of the reaction system to room temperature, and heat it at 120 ° C for 10 h. After the reaction was completed, the mixture was allowed to stand and cool, and most of the xylene was removed by vacuum distillation. The residual mixture was chromatographed on a silica gel column to obtain a crude product, which was then chromatographed and recrystallized to obtain the target compound M093. The target molecular mass detected by high-resolution mass spectrometry was 681.236 (theoretical value: 681.24).

[0225] Synthesis Example 2: Synthesis of Organic Compound M096

[0226] (1) Synthesis of intermediate M096-1

[0227]

[0228] Weigh 1-bromo-4-chloro-3,5-difluorobenzene (5.0 g, 1.0 eq), 7H-dibenzocarbazole (2.94 g, 0.5 eq), cesium carbonate (7.16 g, 1.0 eq) and place in a 500 mL three-necked round-bottom flask, add 80 ml of N,N-dimethylformamide, and heat to 40 ° C under nitrogen atmosphere for 12 h. 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 the reaction system was added to a large amount of water under stirring. The solid was precipitated, 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 the target compound M096-1 was obtained by silica gel column chromatography.

[0229] (2) Synthesis of intermediate M096-2

[0230]

[0231] Weigh M096-1 (5.0 g, 1.0 eq), 5-phenyl-5,8-dihydroindole [2,3-C] carbazole (3.61 g, 1.03 eq), cesium carbonate (8.58 g, 2.5 eq) and place in a 500 mL three-necked round-bottom flask, add 100 mL N, N-dimethylformamide, 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, it was allowed to stand and cool, and the reaction system was added to a large amount of water under stirring, and the solid was precipitated, 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 the target compound M096-2 was obtained by silica gel column chromatography.

[0232] (3) Synthesis of intermediate M096-3

[0233]

[0234] Weigh M096-2 (7.0 g, 1.0 eq), 3,5-di-tert-butylphenylboronic acid (2.50 g, 1.2 eq), tetrakistriphenylphosphine palladium Pd(PPh3)4 (0.31 g, 0.03 eq), potassium carbonate (3.07 g, 2.5 eq) and place in a 500 mL three-necked round-bottom flask, add 80 mL 1,4-dioxane and 20 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 loaded on silica gel, and the target compound M096-3 was obtained by silica gel column chromatography.

[0235] (4) Synthesis of target product M096

[0236]

[0237] Weigh M096-3 (7.5 g, 1.0 eq) and place it in a 500 mL three-necked round-bottom flask, add 75 mL of anhydrous xylene, and under a nitrogen atmosphere, cool it to below -30 ° C through a liquid nitrogen-ethanol mixed solution, then slowly add 1.6 M tert-butyl lithium solution (13.1 mL, 2.5 eq), slowly return the temperature of the reaction system to room temperature, and heat it at 60 ° C for 2 h. Cool it to below -30 ° C through a liquid nitrogen-ethanol mixed solution again, add boron tribromide (2.4 mL, 3.0 eq), slowly return the temperature of the reaction system to room temperature, and heat it at 60 ° C for 1 h. Cool it to below -0 ° C through a liquid nitrogen-ethanol mixed solution again, add N, N-diisopropylethylamine (6.3 mL, 4.5 eq), slowly return the temperature of the reaction system to room temperature, and heat it at 120 ° C for 10 h. After the reaction was completed, the mixture was allowed to stand and cool, and most of the xylene was removed by vacuum distillation. The residual mixture was chromatographed on a silica gel column to obtain a crude product, which was then chromatographed and recrystallized to obtain the target compound M096. The target molecular mass detected by high-resolution mass spectrometry was 869.384 (theoretical value: 869.39).

[0238] Theoretical calculation:

[0239] In the present invention, the theoretical calculation of the organic compound is completed by Gaussian16 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 structure of the lowest singlet excited state of the molecule is optimized by TD-B3LYP / 6-31G* method, and the excitation energy in the ground state and excited state configurations corresponds to the absorption (λ abs , nm) and emission spectra (λ em , nm) (considering toluene as solvent, PCM solvent model). ΔE S-T is the energy level difference between the first excited singlet state and the first excited triplet state in the ground state. The results are shown in Tables 1 and 2.

[0240] The structures of the comparative compounds Ref-1 and Ref-2 are as follows:

[0241]

[0242] Table 1

[0243] Compound HOMO(eV) LUMO(eV) <![CDATA[ΔE S-T (eV)]]> Ref-1 -5.08 -1.92 0.30 M173 -5.11 -1.95 0.44

[0244] As can be seen from Table 1, compared with Ref-1, the organic compound M173 provided by the present invention increases the molecular conjugation by adding a benzene ring fusion, which is manifested as the decrease of HOMO and LUMO energy levels and the single triplet energy level difference ΔE S-TIt increases, indicating that the fusion of double benzene rings further increases the molecular conjugation, thereby effectively reducing the triplet energy level of the molecule. Therefore, the fusion of double benzene rings has more advantages than the fusion of single benzene rings in reducing the triplet energy level of the molecule and the feasibility of synthesis.

[0245] Table 2

[0246]

[0247] As can be seen from Table 2, for Ref-2, four fused benzene ring structures are introduced into its structure, although the emission wavelength is red-shifted to yellow light and ΔE S-T Increase, but multiple fused benzene ring structures also cause the vibration relaxation of molecules in the excited state to intensify, and then the enhancement of the emission spectrum shoulder peak, which is unfavorable for the color purity of the material luminescence, and, calculated, the HOMO energy level of Ref-2 is distributed on two naphthalene rings of 7H-dibenzocarbazole, and the boron-containing fused ring structure of the center cannot resonate with two naphthalene rings through nitrogen atoms, so that intramolecular charge transfer occurs, showing a larger Stokes chemical shift and half-peak width broadening. And the compound provided by the present invention increases the fusion of benzo pentacyclic rings by reducing the fusion number of benzene rings, reaches the purpose of adjusting the light color and reducing the triplet energy level, and weakens the vibration relaxation of the molecule caused by the fused benzene ring in the excited state, and the structure of the benzo pentacyclic ring and carbazole introduced can be well involved in the resonance structure, which is conducive to the narrowing of the spectrum and the reduction of shoulder peak, thereby showing better color purity and efficiency in the device.

[0248] Device Embodiment

[0249] 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:

[0250] (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;

[0251] (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;

[0252] (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;

[0253] (4) vacuum evaporating compound HT-40 on the hole transport layer as an electron blocking layer, with a total film thickness of 5 nm;

[0254] (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;

[0255] 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 material is the organic compound provided by the present invention;

[0256] (6) vacuum evaporating compound ET-23 on the light-emitting layer as a hole blocking layer, with a total evaporation film thickness of 5 nm;

[0257] (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 film thickness of 25 nm;

[0258] (8) Vacuum evaporation of LiF on the electron transport layer as an electron injection layer with a thickness of 1 nm;

[0259] (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.

[0260] 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.

[0261] Device Examples 1-12

[0262] 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 material is the organic compound provided by the present invention as shown in Table 3 and Table 4.

[0263] Comparative Example 1-2

[0264] 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 is replaced by Ref-1 and Ref-2.

[0265] Device performance test:

[0266] At the same brightness, the driving voltage, device life and external quantum efficiency of each organic electroluminescent device were measured using a digital source meter and a brightness meter. Specifically, the voltage was increased at a rate of 0.1 V per second, and the current density of the organic electroluminescent device was measured when it reached 10 mA / cm 2 The voltage at this time is the driving voltage, and the luminance and external quantum efficiency (EQE, %) are measured at the same time; the life test of LT95 is as follows: use a brightness 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 is in h; in Table 2, the test value of the LT95 life of Comparative Example 1 is recorded as 1.00, and the LT95 lifespans of device embodiments 1-6 are all ratios of their respective test values ​​to the test value of Comparative Example 1 (relative life); in Table 4, the test value of the LT95 life of Comparative Example 2 is recorded as 1.00, and the LT95 lifespans of device embodiments 7-12 are all ratios of their respective test values ​​to the test value of Comparative Example 2 (relative life).

[0267] The test results are shown in Table 3 and Table 4:

[0268] Table 3

[0269] Part Number Doping materials Driving voltage(V) EQE LT95 Device Example 1 M088 4.1 13.5％ 1.84 Device Example 2 M173 4.1 13.9％ 2.28 Device Example 3 M176 4.1 14.2％ 2.35 Device Example 4 M308 4.1 14.5％ 1.50 Device Example 5 M436 4.0 14.2％ 2.10 Device Example 6 M448 3.9 14.9％ 2.24 Comparative Example 1 Ref-1 4.2 13.0％ 1.00

[0270] Table 4

[0271] Part Number Doping materials Driving voltage(V) EQE LT95 Device Example 7 M004 4.0 14.5％ 1.64 Device Example 8 M092 4.1 13.2％ 1.30 Device Example 9 M093 4.0 14.2％ 1.70 Device Example 10 M096 4.0 14.6％ 1.75 Device Example 11 M312 4.0 13.7％ 1.20 Device Example 12 M332 4.0 15.1％ 1.25 Comparative Example 2 Ref-2 4.0 10.2％ 1.00

[0272] Combining the performance data in Table 3 and Table 4, it can be seen that the organic compound provided by the present invention is suitable for phosphorescence sensitized luminescence technology as a narrow-spectrum fluorescent doping material, can effectively improve the luminous efficiency of the device, and prolong the life of the device. It is a fluorescent dopant for the light-emitting layer with good performance.

[0273] As can be seen from the results of Table 3, compared with Ref-1, the organic compound of the present invention is used as a fluorescent doping material, and the luminous efficiency and life of the device prepared are improved, which can be mainly attributed to the introduction of the dibenzocarbazole group in the parent core can significantly reduce the triplet energy level of the molecule, thereby enhancing the stability of the doping material under electroluminescence, which is beneficial to the device life. As can be seen from the results of Table 4, compared with Ref-2, the luminous efficiency of the device prepared by the organic compound of the present invention as a fluorescent doping material is improved, which can be mainly attributed to the introduction of the benzo pentacyclic carbazole group such as indole carbazole in the parent core can significantly inhibit the structural relaxation of the dibenzocarbazole group in the excited state, thereby enhancing the fluorescent quantum efficiency of the material, reducing the half-peak width of the material emission spectrum, and thus improving the luminous efficiency under electroluminescence. At the same time, it can be seen from Table 4 that after the organic compound of the present invention improves the significant intramolecular charge transfer properties of Ref-2, the life of the device prepared as a fluorescent doping material is improved.

[0274] The applicant declares that the present invention uses the above-mentioned embodiments to illustrate the organic compounds and their applications, and the organic electroluminescent devices containing the same, 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. An organic compound, characterized in that The organic compound has a structure as shown in Formula I: Among them, the chemical bonds shown by a, b, c, d, e, f, g, i, j, and k represent bonds that can be fused; In Formula I, at least one of the chemical bonds represented by a, b, c, d, and e is fused to the structure represented by Formula a, at least one of the chemical bonds represented by f and g is fused to the structure represented by Formula b, and at least one of the chemical bonds represented by i, j, and k is fused to the structure represented by Formula b; Dashed lines represent fused bonds; X is selected from O, S, CR 11 R 12 NR 13 or SiR 14 R 15 Any of the following: R 11 , R 12 , R 13 , R 14 , R 15 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 C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; the R 11 and R 12 are not connected or connected to form a ring through chemical bonds, the R 14 and R 15 They are not connected to each other or connected to form a ring through chemical bonds; Y1, Y2, Y3, and Y4 are each independently selected from CR 5 or N; X1, X2, X3, and X4 are each independently selected from CR 6 or N; Y 11 , Y 12 , Y 13 Each independently selected from CR 7 or N; R 1 , R 2 , R 3 , R 4 Each independently represents no substitution, monosubstitution to the maximum allowed substitution; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 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 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 Each independently is not connected to the adjacent ring structure or is connected to form a ring through a chemical bond; 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-C30 arylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or a combination of at least two thereof; adjacent R's are not connected or are connected to form a ring by chemical bonds; the R' is not connected to adjacent ring structures or is connected to form a ring by chemical bonds.

2. The organic compound according to claim 1, characterized in that In Formula I, it is fused to the structure shown in Formula a through one of the chemical bonds shown in a and b; Preferably, in Formula I, the structure represented by Formula a is fused via the chemical bond represented by Formula b.

3. The organic compound according to claim 1, characterized in that In formula I, it is fused to the structure shown in formula b through one of the chemical bonds represented by f and g, and is fused to the structure shown in formula b through one of the chemical bonds represented by i, j, and k; Preferably, in Formula I, it is fused to the structure shown in Formula b through the chemical bond shown in f, and is fused to the structure shown in Formula b through one of the chemical bonds shown in i, j, and k; Further preferably, in Formula I, it is fused to the structure shown in Formula b via the chemical bond shown in f, and is fused to the structure shown in Formula b via the chemical bond shown in i.

4. The organic compound according to claim 1, characterized in that The organic compound has a structure as shown in any one of Formulas II-1 to II-3, wherein one of the chemical bonds shown in i, j, and k is fused with the structure shown in Formula b: Wherein, X1, X2, X3, and X4 have the same limited range as in formula b; X, Y1, Y2, Y3, and Y4 have the same defined ranges as in formula a; Y 11 , Y 12 , Y 13 , R 1 , R 2 , R 3 , R 4 has the same definition as in Formula I.

5. The organic compound according to claim 1, characterized in that The organic compound has a structure as shown in any one of Formula III-1 to Formula III-24: Wherein, X, Y1, Y2, Y3, and Y4 have the same limited ranges as in formula a; X1, X2, X3, and X4 have the same defined ranges as in formula b; Y 11 , Y 12 , Y 13 , R 1 , R 2 , R 3 , R 4 Having the same definition as in Formula I; X1', X2', X3', X4' are each independently selected from CR 6 or N; R 6 Has the same definition as in formula b.

6. The organic compound according to claim 5, characterized in that The Y1, Y2, Y3, and Y4 are each independently CR 5 ; Preferably, Y1, Y2, Y3 and Y4 are all CH; Preferably, X1, X2, X3, X4, X1', X2', X3', X4' are each independently CR 6 ; Preferably, X1, X2, X3, X4, X1', X2', X3' and X4' are all CH; Preferably, the Y 11 , Y 12 , Y 13 Each independently is CR 7 ; Preferably, the Y 11 , Y 12 and Y 13 The number of CH in the medium is 1-3; Preferably, the Y 11 and Y 13 is CH, the Y 12 CR 7 ; or, said Y 12 is CH, the Y 11 and Y 13 At least one of them is CR 7 ; Preferably, the Y 11 and Y 13 is CH, the Y 12 CR 7 ; Preferably, the R 7 Each is independently selected from any one of hydrogen, cyano, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; Preferably, the R' is independently selected from any one or a combination of at least two of halogen, cyano, C1-C20 straight or branched alkyl, C2-C20 alkenyl, C6-C30 aryl, C3-C30 heteroaryl; adjacent R' are not connected or are connected to form a ring through chemical bonds; the R' is not connected to the adjacent ring structure or is connected to form a ring through chemical bonds.

7. The organic compound according to claim 1, characterized in that The organic compound has a structure as shown in any one of Formula IV-1 to Formula IV-24: Among them, R 7 Indicates no substitution, monosubstitution to the maximum allowed substitution; X and R 7 The same species definitions as in Formula I are present.

8. The organic compound according to any one of claims 1 to 7, characterized in that The X is selected from O, S, CR 11 R 12 NR 13 Any of the following: Preferably, X is selected from CR 11 R 12 NR 13 Any one of, more preferably NR 13 ; Preferably, the R 13 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 C6-C30 aryl, and unsubstituted or R'-substituted C3-C30 heteroaryl, more preferably any one of C1-C10 straight or branched alkyl, and C6-C20 aryl, and even more preferably phenyl.

9. The organic compound according to claim 7, characterized in that: The R 7 represents no substitution or single substitution; Preferably, the R 7 represents a single substitution; Preferably, the R 7 Any one selected from hydrogen, cyano, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C6-C30 arylamino, unsubstituted or R'substituted C6-C60 aryl, and unsubstituted or R'substituted C3-C60 heteroaryl, preferably any one selected from hydrogen, unsubstituted or R'substituted C1-C10 straight or branched alkyl, unsubstituted or R'substituted C3-C10 cycloalkyl, unsubstituted or R'substituted C6-C30 arylamino, unsubstituted or R'substituted C6-C20 aryl, and unsubstituted or R'substituted C3-C20 heteroaryl; Preferably, the R 7 Any one of the following groups selected from hydrogen, unsubstituted or R'substituted: C1-C5 straight or branched alkyl, C6-C10 cycloalkyl, -* represents the attachment site of the group; Z is selected from O, S, CR 21 R 22 or NR 23 Any of the following: R 21 , R 22 , R 23 Each is independently selected from any one or a combination of at least two of a C1-C20 straight or branched alkyl group, a C3-C20 cycloalkyl group, a C2-C20 alkenyl group, a C6-C30 aryl group, and a C3-C30 heteroaryl group; 21 and R 22 Not connected or connected into rings by chemical bonds; Preferably, the R's are independently selected from any one or a combination of at least two of halogen, cyano, C1-C10 straight or branched alkyl, C1-C10 cycloalkyl, C2-C10 alkenyl, C6-C20 aryl, and C3-C20 heteroaryl; adjacent R's are not connected or are connected to form a ring through chemical bonds; the R's are not connected to adjacent ring structures or are connected to form a ring through chemical bonds; Preferably, the R' is independently selected from any one or a combination of at least two of halogen, cyano, C1-C5 straight or branched alkyl, C6-C20 aryl, C3-C20 heteroaryl, more preferably fluorine, cyano, C1-C5 straight or branched alkyl, C6-C20 aryl, C3-C20 heteroaryl, more preferably fluorine, cyano, methyl, perfluoromethyl, ethyl, Any one or a combination of at least two of the following; -* represents the connection site of the group.

10. The organic compound according to claim 7, characterized in that: The R 7 are each independently selected from hydrogen, methyl, Any of the above, -* represents the attachment site of the group.

11. The organic compound according to claim 1, characterized in that: The organic compound has a structure shown in any one of the following M001-M472:

12. Use of an organic compound as claimed in any one of claims 1 to 11, characterized in that: The organic compound is applied to organic electronic devices; Preferably, the organic electronic device comprises an organic electroluminescent device; Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device.

13. 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 organic compound according to any one of claims 1 to 11; Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one organic compound according to any one of claims 1 to 11; Preferably, the light-emitting layer comprises a host material and a doping material, and the doping material comprises at least one organic compound as claimed in any one of claims 1 to 11; 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.

14. A display device, characterized in that: The display device comprises the organic electroluminescent device as claimed in claim 13.

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