Organic compound, application thereof and organic electroluminescent device

Abstract

The invention provides an organic compound and application thereof and an organic electroluminescent device, the organic compound has a structure as shown in a formula I, a parent nucleus of the organic compound is a fused ring structure containing O and / or S. The organic compound has excellent electron transmission performance and photoelectric property by designing a specific fused ring structure to be connected with a triazine structure; the organic electroluminescent device is especially suitable for being used as a host material of a luminescent layer, can realize an excellent carrier, especially electron transmission effect, enables the energy transfer rate between a host and an object to be faster, reduces TTA and TPQ in the luminescent layer, and increases the utilization rate of excitons, thereby effectively improving the luminescent efficiency of the organic electroluminescent device, reducing the voltage and energy consumption, and improving the luminous efficiency of the organic electroluminescent device. And the device has better comprehensive luminescence performance.

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. Background Art

[0002] In recent years, optoelectronic devices based on organic materials have developed rapidly and become a research hotspot in the field. Examples of organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic photovoltaic cells, organic sensors, etc. Among them, OLEDs have developed particularly rapidly and have achieved commercial success in the field of information display. OLEDs can provide highly saturated red, green, and blue colors. Full-color display devices made of OLEDs do not require additional backlight sources and have the advantages of bright colors, lightness, thinness, and softness.

[0003] The core of OLED devices is a multilayer thin film structure containing a variety of functionalized organic materials. Common functionalized organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, luminescent host materials and luminescent guest materials (dyes), etc. When power is turned on, electrons and holes are injected and transported to the luminescent area respectively and recombine there, thereby generating excitons and emitting light.

[0004] According to the luminescence mechanism, current OLEDs can be divided into fluorescent luminescence, phosphorescent luminescence, thermally excited delayed fluorescence and thermally excited sensitized fluorescence. Common fluorescent luminescent bodies mainly use singlet excitons generated when electrons and holes combine to emit light, and are still widely used in various OLED products. Some metal complexes (such as iridium complexes and platinum complexes) can simultaneously use triplet excitons and singlet excitons to emit light, and are called phosphorescent luminescent bodies. Their energy conversion efficiency can be four times higher than that of traditional fluorescent luminescent bodies. Thermally excited delayed fluorescence (TADF) promotes the transformation of triplet excitons to singlet excitons. Without the use of metal complexes, triplet excitons can still be effectively utilized to achieve higher luminescence efficiency. Thermally excited sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize the luminescent body through energy transfer, which can achieve higher luminescence efficiency.

[0005] Although products using OLED technology have been commercialized, the device's lifespan, efficiency and other performance still need to be continuously improved to meet people's pursuit of high-quality display effects. Therefore, the field is in urgent need of developing more types of higher-performance organic materials, which can be applied to organic electroluminescent devices to make the devices have better luminous effects. Summary of the invention

[0006] 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. Through the design of the compound structure, the organic compound has excellent photoelectric properties and is applied to organic electroluminescent devices, and is particularly suitable as a main material for the light-emitting layer, which can effectively improve the efficiency of the device and reduce voltage and energy consumption.

[0007] To achieve this object, the present invention adopts the following technical solutions:

[0008] In a first aspect, the present invention provides an organic compound having a structure as shown in Formula I:

[0009]

[0010] In Formula I, Ring A is selected from any one of substituted or unsubstituted C6-C60 aromatic rings.

[0011] The substituents substituted in ring A are each independently selected from any one of halogen, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, 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.

[0012] In formula I, Y1 and Y2 are each independently S or O.

[0013] In Formula I, X1, X2, X3, X4, X5, X6, X7, and X8 are each independently selected from CR1, CR A or N, and at least one of X1, X2, X3, X4, X5, X6, X7 and X8 is CR A .

[0014] R1 is independently selected from any one of hydrogen, halogen, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, 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.

[0015] The R1s are each independently not connected to adjacent ring structures or are connected to form a ring through a chemical bond.

[0016] In the present invention, "R1 is not connected to the adjacent ring structure" means that R1 is only connected to the C atom by a single bond; "R1 is connected to the adjacent ring structure by a chemical bond to form a ring" means that R1 is connected to the C atom by a chemical bond and is also connected to the adjacent ring (such as the ring of the parent core of Formula I) by a chemical bond, thereby forming a fused ring structure. When the same description is involved below, it has the same meaning and will not be repeated one by one.

[0017] It should be noted that R1 in a plurality of CR1s of X1 to X8 may be the same or different groups.

[0018] R A It has the structure shown in formula a:

[0019]

[0020] In formula a, -* represents the attachment site of the group.

[0021] In formula a, L is selected from any one of a single bond, an unsubstituted or R'-substituted C6-C60 arylene group, and an unsubstituted or R'-substituted C3-C60 heteroarylene group; when L is a single bond, it represents that the C atom of the triazine ring in formula a is directly connected to the C atom of the parent core in formula I through a single bond.

[0022] In formula a, Ar1 and Ar2 are each independently selected from any one of an unsubstituted or R'-substituted C6-C60 aryl group and an unsubstituted or R'-substituted C3-C60 heteroaryl group.

[0023] R' is independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or a combination of at least two thereof; each of the R's is independently not connected to an adjacent ring structure or is connected to form a ring by a chemical bond.

[0024] In the present invention, the "substituted or unsubstituted" or "unsubstituted or R' substituted" group / ring may be substituted with one substituent or with multiple substituents. When there are multiple substituents (at least 2), 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 the substituted substituent is as shown above, and the definition of R' is as shown above and will not be repeated.

[0025] The organic compound provided by the present invention has a molecular structure shown in Formula I, and its parent core is a condensed ring structure containing O and / or S. By designing a specific condensed ring structure connected to the triazine structure shown in Formula a, the organic compound has excellent electron transport performance and photoelectric properties, and is particularly suitable as a main material of the light-emitting layer, and can effectively improve the luminous efficiency of the organic electroluminescent device, and reduce voltage and energy consumption. At the same time, the parent core structure contains O and / or S atoms (Y1 and Y2), and under the action of such heteroatoms with lone pairs of electrons, the organic compound is used as the main material of the light-emitting layer, so that the energy transfer rate between the host and the guest is faster, and the occurrence of TTA (triplet-triplet annihilation) and TPQ (triplet-polaron quenching) in the light-emitting layer is reduced, and the utilization rate of excitons is increased, thereby further significantly improving the luminous efficiency of the device.

[0026] It should be noted that, for the sake of convenience, 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 reason for obtaining good performance is essentially 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.

[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), 3H (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 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, 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.

[0035] 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.

[0036] 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.

[0037] 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.

[0038] 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.

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

[0040] The C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0041] 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.

[0042] Specific examples of the C1-C20 alkoxy group include monovalent groups obtained by connecting the above-mentioned linear or branched alkyl groups to O.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] The C6-C60 aryl group is preferably a C6-C30 aryl group, and more preferably a C6-C20 aryl group, including 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 mutually opposite bonds. The adjacent carbon atoms 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 group and the condensed aromatic group connected by a single bond also belong to the scope of aromatic group, such as phenylnaphthyl, naphthylphenyl, etc.

[0047] The C3-C60 heteroaryl group is preferably a C3-C30 heteroaryl group, and more preferably a C3-C20 heteroaryl group, including a monocyclic heteroaryl group or a condensed ring heteroaryl group. The monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains a heteroaryl group and other groups (such as aryl, heteroaryl, etc.), the heteroaryl group and the other groups are connected by a single bond, and exemplary examples include but are 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 share two adjacent atoms that are fused to each other, including, but not limited to, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, isobenzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, naphthiobenzofuranyl, naphthiobenzothiophenyl, carbazolyl and its derivatives (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolcarbazolyl, azacarbazolyl, etc.), acridinyl, phenothiazinyl, phenoxazinyl, hydroacridinyl, etc.

[0048] 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.

[0049] In the present invention, specific examples of the C6-C60 arylamino and C6-C30 arylamino groups are monovalent groups in which at least one hydrogen in -NH2 is replaced by the above aryl groups, including but not limited to phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrenylamino, biphenylamino, etc. Specific examples of the C3-C60 heteroarylamino and C3-C30 heteroarylamino groups are monovalent groups in which at least one hydrogen in -NH2 is replaced by the above heteroaryl groups, including but not limited to pyridylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0050] Preferably, the ring A is selected from a substituted or unsubstituted benzene ring, and the organic compound has a structure as shown in Formula II:

[0051]

[0052] In Formula II, X9, X 10 , X 11 , X 12 Each is independently selected from CR2; R2 in multiple (2, 3, 4) CR2s are the same or different groups.

[0053] R2 is each independently selected from hydrogen, halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or Any one of 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 R2s are each independently not connected to the adjacent ring structure or are connected to form a ring by chemical bonds.

[0054] In Formula II, Y1, Y2, X1, X2, X3, X4, X5, X6, X7, and X8 have the same defined ranges as in Formula I.

[0055] In Formula I and Formula II, Y1 and Y2 are both O, or, Y1 and Y2 are both S, or, one of Y1 and Y2 is O and the other is S.

[0056] Preferably, at least one of Y1 and Y2 is O.

[0057] Preferably, X1, X2, X3, X4, X5, X6, X7, and X8 are each independently selected from CR1 or CR A , and at least one of them is CR A .

[0058] Preferably, one and only one of X1, X2, X3, X4, X5, X6, X7 and X8 is CR A .

[0059] Preferably, the organic compound has a structure as shown in Formula III:

[0060]

[0061] In formula III, Y1 and Y2 are each independently S or O.

[0062] In formula III, two R1 and R2 represent no substitution (ie, R1 and R2 are H), single substitution to the maximum allowable substitution.

[0063] In formula III, two R1 and R2 are the same or different and are independently selected from hydrogen, halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C1-C20 alkylamino, cyano, nitro, hydroxyl, The invention can be any one of amino, 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; R1 and R2 are each independently not connected to the adjacent ring structure or are connected to form a ring by chemical bonds.

[0064] Preferably, one of X2, X3, X6 or X7 is CR A .

[0065] Preferably, the organic compound has a structure as shown in Formula IIIA or Formula IIIB:

[0066]

[0067] Preferably, R1 is selected from hydrogen, cyano, unsubstituted or R'substituted C1-C10 (e.g. C1, C2, C3, C4, C5, C6, C8, C10, etc.) straight or branched alkyl, unsubstituted or R'substituted C3-C10 (e.g. C3, C4, C5, C6, C8, C10, etc.) cycloalkyl, unsubstituted or R'substituted C6-C20 (e.g. C6, C9, C10, C12, Any one of R'-substituted C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, unsubstituted or R'-substituted C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl, further preferably hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, cyanophenyl, methylphenyl or tert-butylphenyl, further preferably hydrogen.

[0068] Preferably, R2 is selected from hydrogen, cyano, unsubstituted or R'substituted C1-C10 (e.g. C1, C2, C3, C4, C5, C6, C8, C10, etc.) straight or branched alkyl, unsubstituted or R'substituted C3-C10 (e.g. C3, C4, C5, C6, C8, C10, etc.) cycloalkyl, unsubstituted or R'substituted C6-C20 (e.g. C6, C9, C10, C12, Any one of R'-substituted C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, unsubstituted or R'-substituted C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl, further preferably hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, cyanophenyl, methylphenyl or tert-butylphenyl, further preferably hydrogen.

[0069] Preferably, in formula a, L is selected from any one of a single bond, an unsubstituted or R'-substituted C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C25, C28, etc.) arylene group, and an unsubstituted or R'-substituted C3-C30 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C25, C28, etc.) heteroarylene group, preferably any one of a single bond, an unsubstituted or R'-substituted C6-C13 arylene group, and an unsubstituted or R'-substituted C5-C20 heteroarylene group.

[0070] Preferably, L is selected from any one of the following groups which are single bonds, unsubstituted or R'-substituted:

[0071] Wherein, -* represents the attachment site of the group.

[0072] Z1 is selected from O, S, CR11 R 12 or NR 13 Any of the following;

[0073] R 11 , R 12 , R 13 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-C10 alkenyl group, a C6-C30 aryl group, and a C3-C30 heteroaryl group; 11 and R 12 Not connected or connected to form a ring through chemical bonds.

[0074] Preferably, Z1 is O or S.

[0075] Preferably, L is selected from a single bond, an unsubstituted or R'-substituted phenylene group (an unsubstituted or R'-substituted ), unsubstituted or R'-substituted naphthylene (unsubstituted or R'-substituted ), unsubstituted or R'-substituted biphenylene (unsubstituted or R'-substituted , unsubstituted or R' substituted ), unsubstituted or R'-substituted dibenzofuran (unsubstituted or R'-substituted , unsubstituted or R' substituted ), unsubstituted or R'-substituted dibenzothiophenylene (unsubstituted or R'-substituted Unsubstituted or R' substituted )

[0076] The R' in L 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, preferably any one or a combination of at least two of halogen, cyano, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C6-C30 aryl, further preferably any one or a combination of at least two of halogen, cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C8, etc.) straight or branched alkyl, C3-C10 cycloalkyl (e.g., C3, C4, C5, C6, C8, etc.). When the same expressions are mentioned below, they all have the same meaning.

[0077] Preferably, L is selected from any one of the following groups which are single bonds, unsubstituted or R'-substituted: More preferably, a single bond, or

[0078] Preferably, L is selected from any one of the following groups which are single bonds, unsubstituted or R'-substituted: -* represents the attachment site of the group.

[0079] In another preferred technical solution, the L is selected from any one of the following groups which are unsubstituted or R'-substituted:

[0080]

[0081] Preferably, L is selected from a single bond, Any one of .

[0082] Preferably, Ar1 and Ar2 are each independently selected from any one of unsubstituted or R'-substituted C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C25, C28, etc.) aryl, and unsubstituted or R'-substituted C3-C30 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C25, C28, etc.) heteroaryl; R' is each independently selected from Any one or a combination of at least two 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; and each R' is independently not connected to the adjacent ring structure or is connected to form a ring by a chemical bond.

[0083] Preferably, Ar1 and Ar2 are each independently selected from any one of the following groups which are unsubstituted or R'-substituted:

[0084] Wherein, -* represents the attachment site of the group.

[0085] Z2 is selected from O, S, CR 21 R 22 or NR 23 Any one of .

[0086] R 21 , R 22 , R23 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-C10 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.

[0087] Preferably, Ar1 and Ar2 are each independently selected from any one of the following groups which are unsubstituted or R'-substituted:

[0088] Further preferred is any one of the following groups which are unsubstituted or R'-substituted:

[0089] Preferably, Z2 is O, S or CR 21 R 22 .

[0090] Preferably, the R 21 , R 22 Each is independently selected from any one of C1-C10 (for example, C2, C3, C4, C5, C6, C8, etc.) straight chain or branched alkyl, C6-C20 (for example, C6, C7, C8, C9, C10, C12, C14, C16 or C18, etc.) aryl, further preferably any one of C1-C6 straight chain or branched alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, and further preferably methyl.

[0091] Preferably, the R' in Ar1 and Ar2 are each independently selected from halogen, cyano, nitro, hydroxyl, amino, C1-C10 (e.g., C2, C3, C4, C5, C6, C8, etc.) straight or branched alkyl, C3-C10 (e.g., C4, C5, C6, C8, etc.) cycloalkyl, C2-C10 (e.g., C2, C3, C4, C5, C6, C8, etc.) alkenyl, C6-C30 (e.g., C6, C9, C10, etc.) , C12, C14, C15, C16, C18, C20, C22, C25, C28, etc.) aryl, C3-C30 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C25, C28, etc.) heteroaryl or a combination of at least two thereof; the R' is independently not connected to the adjacent ring structure or is connected to form a ring by a chemical bond.

[0092] Preferably, the R' is independently selected from any one of halogen, cyano, C1-C6 straight or branched alkyl, C3-C10 cycloalkyl, C2-C6 alkenyl, phenyl, biphenyl, and naphthyl, and more preferably any one of halogen, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexyl, C2-C6 alkenyl, phenyl, biphenyl, and naphthyl.

[0093] Preferably, the R' in Ar1 and Ar2 are independently not connected to the adjacent ring structure or are connected by chemical bonds to form a ring Cy, and the ring Cy is selected from any one of a substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aromatic ring, a substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaromatic ring, and more preferably In any of the above examples, the dotted line represents the fused bond of ring Cy.

[0094] Preferably, Ar1 and Ar2 are each independently selected from any one of the following groups which are unsubstituted or R'-substituted:

[0095]

[0096]

[0097] Further preferably, Ar1 and Ar2 are each independently selected from any one of the following groups which are unsubstituted or R'-substituted:

[0098]

[0099] ; Wherein, -* represents the attachment site of the group.

[0100] Preferably, Ar1 and Ar2 are each independently selected from any one of the following groups which are unsubstituted or R'-substituted:

[0101]

[0102] Preferably, the organic compound has a structure shown in any one of the following N1-N631:

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[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]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151] 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.

[0152] 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.

[0153] Preferably, the organic compound is applied to an organic electroluminescent device, and more preferably applied to a red organic electroluminescent device.

[0154] Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device, and more preferably as a host material of the light-emitting layer.

[0155] 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.

[0156] Preferably, the organic layer comprises at least one organic compound having a structure shown by N1-N631.

[0157] 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.

[0158] Preferably, the light-emitting layer comprises a host material and a doping material, and the host material comprises at least one organic compound as described in the first aspect.

[0159] As a preferred technical solution of the present invention, the organic compound serves as the main material of the light-emitting layer, which is an electronic main material with a low triplet energy level difference, and is particularly suitable as the main material of the red light-emitting layer. It can improve the life and luminous efficiency of the organic electroluminescent device and reduce the operating voltage and energy consumption.

[0160] Preferably, the host material comprises a combination of a first host material and a second host material, and the first host material comprises at least one organic compound as described in the first aspect.

[0161] Preferably, the second host material has a structure as shown in Formula IV:

[0162]

[0163] In formula IV, Ar3, Ar4, and Ar5 are each independently selected from any one of a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group; Ar3, Ar4, and Ar5 are not connected or are connected to form a ring through chemical bonds.

[0164] The substituted substituents in Ar3, Ar4 and Ar5 are each independently selected from any one of halogen, C1-C20 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl and C3-C60 heteroaryl; in Ar3, Ar4 and Ar5, the substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring by chemical bonds.

[0165] Preferably, the organic compound is used as the first host material in a dual host device, which has excellent electron transport performance. When compounded with the second host material of the structure shown in Formula IV, it can effectively regulate and achieve the transmission balance of holes and electrons, further improve the efficiency and life of the device, and give the device better overall performance.

[0166] Preferably, the mass ratio of the first host material to the second host material is (0.1-2):1, for example, it can be 0.2:1, 0.3:1, 0.4:1, 0.5:1, 0.6:1, 0.7:1, 0.8:1, 0.9:1, 1:1, 1.1:1, 1.2:1, 1.3:1, 1.4:1, 1.5:1, 1.6:1, 1.7:1, 1.8:1 or 1.9:1, and is further preferably (0.5-1.5):1.

[0167] Preferably, the doping material (also called "dye", "luminescent dye", "guest material") is a phosphorescent doping material.

[0168] Preferably, based on the mass of the main material being 100%, the mass of the doping material in the light-emitting layer is 0.1-10%, for example, 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8% or 9%.

[0169] Preferably, the organic layer further includes a hole transport region and an electron transport region.

[0170] 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.

[0171] 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.

[0172] 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 with a structure shown in N1-N631.

[0173] In a preferred technical solution, the organic electroluminescent device includes a substrate, and a first electrode, a plurality of light-emitting functional layers (organic layers) and a second electrode sequentially arranged on the substrate; the organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer sequentially arranged, 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 N1-N631.

[0174] 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.

[0175] 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.

[0176] 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.

[0177] 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.

[0178] 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.

[0179]

[0180]

[0181]

[0182] 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.

[0183]

[0184] 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.

[0185] According to different technologies, the light-emitting layer material can be made of different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, thermally activated delayed fluorescent materials, etc. In an OLED device, a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be used. These different light-emitting materials classified by technology can emit light of the same color or different colors.

[0186] In the preferred technical solution of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The main material of the light-emitting layer includes a combination of a first main material and a second main material, wherein the first main material includes at least one organic compound described in Formula I.

[0187] The second host material has Specifically, the second host material can be selected from, but not limited to, one or more combinations of the following specific compounds H1-H32.

[0188]

[0189]

[0190]

[0191]

[0192] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of RPD-1 to RPD-28 listed below.

[0193]

[0194]

[0195] 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 one or more compounds of HT-1 to HT-51, but is not limited thereto.

[0196] 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).

[0197] 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.

[0198]

[0199]

[0200]

[0201]

[0202] 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 one or more compounds of the above ET-1 to ET-73, but is not limited thereto.

[0203] 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.

[0204] In a fourth aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the third aspect.

[0205] Preferably, the display device includes a display screen or a display panel.

[0206] The present invention also provides an electronic device, which includes the above-mentioned display device.

[0207] Compared with the prior art, the present invention has the following beneficial effects:

[0208] The organic compound provided by the present invention has a structure shown in Formula I, wherein the parent core is a condensed ring structure containing O and / or S, and the organic compound has excellent electron transport performance and photoelectric properties by designing a specific condensed ring structure connected with a triazine structure, and is particularly suitable as a host material of a light-emitting layer, and can achieve excellent carrier, especially electron transport effects, and make the energy transfer rate between the host and the guest faster, reduce the occurrence of TTA and TPQ in the light-emitting layer, and increase the utilization rate of excitons, thereby effectively improving the luminous efficiency of the organic electroluminescent device, reducing voltage and energy consumption, and making the device have better comprehensive luminous performance. DETAILED DESCRIPTION

[0209] 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.

[0210] The organic compound represented by Formula I of the present invention can be synthesized by known organic synthesis methods. An exemplary synthesis route is given below, but those skilled in the art can also obtain it by other known methods.

[0211] In a specific embodiment, the organic compound can be prepared by the following synthetic route:

[0212]

[0213] Among them, ring A, Y1, Y2, X1, X2, X3, X4, R A It has the same definition as in formula I and formula a; in raw material A, X5, X6, X7, and X8 are each independently selected from CR1, CR B or N, and one of them is CR B , R1 is defined as in Formula I, R B is a methoxy group; Hal1, Hal2, Hal3 are each independently selected from halogen, preferably Cl, Br or I.

[0214] In intermediate A, one of X5, X6, X7, and X8 is CR B , R B is a methoxyl group, which is converted into Then with R A -Hal3( ) to carry out coupling reaction to obtain the target product with the structure shown in formula I.

[0215] In one embodiment, R B Methoxy group is converted to , an exemplary reaction pathway is: first converting the methoxy group into a hydroxyl group, and then reacting with trifluoromethanesulfonic anhydride to convert the hydroxyl group into a trifluoromethanesulfonic acid group ( ), and then reacted with biboric acid pinacol ester to obtain

[0216] The specific preparation method of the organic compound of the present invention will be described in detail below using multiple preparation examples and synthesis examples as examples. However, the preparation method of the organic compound of the structure shown in Formula I of the present invention includes but is not limited to the synthesis method in the specific implementation method. Those skilled in the art can also make routine adjustments to the preparation method according to actual needs. The organic compound of the structure shown in Formula I synthesized by other methods also belongs to the protection scope of the present invention.

[0217] The following preparation examples and synthesis examples of the present invention exemplarily provide specific synthesis methods of representative compounds. The solvents and reagents used in the synthesis examples can be purchased or customized from the chemical product market. The mass spectrometry characterization data (MS) of the intermediates and target compounds in the present invention are obtained by mass spectrometer testing; the reaction process and end point are detected by gas chromatography-mass spectrometry (GC-MS) and / or thin layer chromatography (TLC).

[0218] The compounds of the synthesis methods not mentioned in the present invention are all raw materials obtained from commercial channels, or are prepared by themselves according to known methods using these raw materials.

[0219] Preparation Example 1: Synthesis of Intermediate M1

[0220]

[0221] S1 (0.5 mol) and N,N-dimethylformamide (DMF, 1000 mL) were added to the reaction bottle, cooled to 0°C, and N-iodosuccinimide (NIS, 0.6 mol) was added in batches. The temperature did not exceed 10°C during the process. After the addition was completed, the reaction was allowed to react at room temperature for 5 hours. After the reaction was completed by GC-MS, the reaction solution was poured into water to precipitate a large amount of solids. The intermediate M1-1 was filtered and dried.

[0222] Intermediate M1-1 (0.35 mol), 2-chloro-5-methoxyphenol (0.35 mol), cuprous iodide (0.3 mol), o-phenanthroline (0.6 mol), and cesium carbonate (0.4 mol) were added to DMF (1000 mL), heated to 100° C. for 10 h, and the reaction was complete under TLC monitoring. After the reaction system was cooled, DMF was directly distilled off under reduced pressure, and intermediate M1-2 was obtained by substrate column chromatography purification.

[0223] The intermediate M1-2 (0.2 mol), cesium carbonate (0.4 mol), palladium acetate (0.01 mol), and tricyclohexylphosphine (0.02 mol) were added to DMF (800 mL), heated to reflux for 4 h, and the reaction was completed under the control of TLC. After cooling, water and dichloromethane were added for extraction. When the organic phase was concentrated to 100 mL, a large amount of solid precipitated. After adding 300 mL of ethanol, the white solid M1-3 was obtained by filtration.

[0224] The intermediate M1-3 (0.17 mol) was added to dichloromethane (1000 mL), cooled to 0°C, and boron tribromide (0.25 mol) was added dropwise. After the addition was completed, the temperature was gradually raised to room temperature for 5 hours. The reaction was complete under TLC monitoring. After cooling, the reaction solution was quenched with water, and the organic phase was concentrated to 200 mL. A large amount of solid precipitated, which was filtered and the filter cake was washed once with ethanol to obtain the intermediate M1-4.

[0225] M1-4 (0.14 mol), triethylamine (0.42 mol) and 3000 mL of dichloromethane were added to the reaction flask, stirred for 30 min and gradually dissolved, cooled to 0 °C and trifluoromethanesulfonic anhydride (0.28 mol) was added dropwise, and after the addition was completed, the temperature was gradually restored to room temperature for 2 h. The reaction was complete under TLC monitoring. The reaction solution was poured into water, the organic phase was separated and concentrated to obtain a brown solid, and the intermediate M1-5 was obtained after recrystallization from toluene / ethanol.

[0226] M1-5 (0.1 mol), bipyralidin (0.12 mol), potassium acetate (0.15 mol), (1,1'-bis(diphenylphosphino)ferrocene)palladium dichloride (0.001 mol), and 500 mL of dioxane were added to a reaction flask and heated to reflux for 5 h. The reaction was completed under the control of TLC. The reaction solution was directly filtered and concentrated. The substrate was washed with methanol and then filtered and dried to obtain the intermediate M1 (MS: 435.2).

[0227] Preparation Example 2-4: Synthesis of Intermediates M2, M3, and M4

[0228] The synthesis method of intermediates M2, M3, and M4 is similar to that of intermediate M1, except that 2-chloro-5-methoxyphenol in Preparation Example 1 is replaced by equimolar amounts of 2-chloro-4-methoxyphenol, 2-chloro-3-methoxyphenol, and 2-chloro-6-methoxyphenol, respectively, and other materials, synthesis steps, and parameters are the same as those in Preparation Example 1 to obtain intermediates M2, M3, and M4 as shown below.

[0229]

[0230] Preparation Example 5: Synthesis of Intermediate 5

[0231]

[0232] The synthesis method of intermediate M5 is similar to that of intermediate M1, except that S1 in Preparation Example 1 is replaced by an equimolar amount of S2, and other materials, synthesis steps and parameters are the same as those in Preparation Example 1 to obtain intermediate M5 (MS: 451.2).

[0233] Preparation Example 6-12: Synthesis of Intermediates M6, M7, M8, M9, M10, M11, and M12

[0234] The synthesis method of intermediates M6, M7, M8, M11 and M12 is similar to that of intermediate M5, except that 2-chloro-5-methoxyphenol in Preparation Example 5 is replaced by equimolar amounts of 2-chloro-4-methoxyphenol, 2-chloro-3-methoxyphenol, 2-chloro-6-methoxyphenol, 2-chloro-5-methoxythiophenol and 2-chloro-4-methoxythiophenol, respectively, and other materials, synthesis steps and parameters are the same as those in Preparation Example 5 to obtain intermediates M6, M7, M8, M11 and M12 as shown below.

[0235] The synthesis method of intermediates M9 and M10 is similar to that of intermediate M1, except that 2-chloro-5-methoxyphenol in Preparation Example 1 is replaced by equimolar amounts of 2-chloro-4-methoxythiophenol and 2-chloro-5-methoxythiophenol, respectively, and other materials, synthesis steps and parameters are the same as those in Preparation Example 1 to obtain intermediates M9 and M10 as shown below.

[0236]

[0237] Synthesis Example 1: Synthesis of Organic Compound N93

[0238]

[0239] Intermediate M12 (0.02 mol, hereinafter referred to as intermediate M), raw material C1 (0.02 mol, hereinafter referred to as raw material C), potassium carbonate (0.024 mol), tris(dibenzylideneacetone)dipalladium (0.0002 mol), 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (0.0004 mol), water (20 mL) and dioxane (200 mL) were added to a reaction bottle, heated to 100° C. and reacted for 5 h. The reaction was completed under the control of TLC. Water and dichloromethane were added for extraction. The organic phase was separated and concentrated and purified by column chromatography to obtain the target product N93 (MS: 648.2).

[0240] Synthesis Example 2-31

[0241] The following organic compounds were prepared by a synthetic method similar to that of the organic compound N93, except that the intermediate M and / or raw material C were different. The intermediate M, raw material C, target product and mass spectrometry characterization data (MS) are shown in Table 1.

[0242] Table 1

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253] Most of the raw materials involved in Table 1 can be purchased directly from the market. A small part of the raw materials that are difficult to obtain in bulk on the market are directly customized and synthesized by cooperative intermediate manufacturers. Customized companies can prepare them through simple 1-2 steps of reaction, as shown below:

[0254]

[0255] The present invention exemplarily provides specific synthesis methods for the above-mentioned compounds. For other organic compounds for which no specific synthesis methods are provided, they can also be prepared by similar methods, which can be obtained by simply replacing the raw materials. They will not be described in detail here, or those skilled in the art can also prepare them by other methods in the prior art.

[0256] Device Example 1

[0257] 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) arranged in sequence. The preparation method of the organic electroluminescent device is as follows:

[0258] (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;

[0259] (2) Place the glass substrate with the anode in a vacuum chamber and evacuate the chamber to a vacuum of less than 1×10 -5 Pa, vacuum evaporating a mixture of compound HT-29:HI-1 (97 / 3, w / w) on the above anode layer as a hole injection layer, the evaporation rate is 0.1 nm / s, and the evaporation film thickness is 10 nm;

[0260] (3) vacuum evaporating compound HT-29 on the hole injection layer as a hole transport layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 60 nm;

[0261] (4) vacuum evaporating compound HT-37 on the hole transport layer as an electron blocking layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 60 nm;

[0262] (5) vacuum evaporating a light-emitting layer on the electron blocking layer, wherein the light-emitting layer includes a main material and a doping material (dye, RPD-18), and the mass ratio (w / w) of the main material to the doping material is 100:3; the main material is a mixture of a first main material (the organic compound N93 provided by the present invention) and a second main material (compound H29) (the mass ratio of N93 to H29 is 1:1); the evaporation is carried out by a dual-source co-evaporation method, the evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 40 nm;

[0263] (6) vacuum evaporating compound ET-17 on the light-emitting layer as a hole blocking layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 5 nm;

[0264] (7) vacuum evaporating a mixture of compounds ET-66:ET-57 (50 / 50, w / w) on the hole blocking layer as an electron transport layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 25 nm;

[0265] (8) Vacuum evaporating LiF on the electron transport layer as an electron injection layer at a rate of 0.1 nm / s and a thickness of 1 nm;

[0266] (9) Vacuum evaporating metal Al with a thickness of 150 nm on the electron injection layer as a cathode at a evaporation rate of 1 nm / s to obtain the organic electroluminescent device.

[0267] Device Examples 2-31, Device Comparative Examples 1-3

[0268] An organic electroluminescent device, which differs from device embodiment 1 only in that the main materials of the light-emitting layer are the compounds shown in Table 2, and the mass ratio of the first main material to the second main material is 1:1; other layers, thicknesses, materials and preparation methods are the same as those of device embodiment 1.

[0269] The structure of the host material in the above device embodiment and device comparative example is as follows:

[0270]

[0271] The performance test of the organic electroluminescent devices provided in device examples 1-33 and device comparative examples 1-3 was performed, and the specific method was as follows:

[0272] At the same brightness of 3000cd / m 2 Under the condition of 100 ℃ and 80 ℃, the current density and voltage of the organic electroluminescent device are measured using a digital source meter and a brightness meter. The ratio of brightness to current density is the current efficiency.

[0273] The test values ​​of voltage and current efficiency of device comparison example 1 are recorded as 1, and the ratios of the test values ​​of voltage of other devices to the test values ​​of voltage and current efficiency of device comparison example 1 (relative voltage, relative current efficiency) are calculated. The specific results are shown in Table 2.

[0274] Table 2

[0275]

[0276]

[0277] Combined with the data in Table 2, it can be seen that the organic compound provided by the present invention has excellent electron transport performance and photoelectric properties. As the main material of the light-emitting layer of the organic electroluminescent device, it can effectively improve the luminous efficiency of the device and reduce the voltage. Further, combined with device examples 1-33, it can be seen that the organic compound is combined with a hole-type host with good hole injection and transmission, so that the dual-host red light organic electroluminescent device has a lower voltage and higher efficiency.

[0278] By comparing the light-emitting layer materials and effect data of the device embodiments 1-33 of the present invention with the device comparative examples 1-3, it can be seen that the electron-deficient group in comparative example 1 is a quinazoline group, and its electron transport ability is significantly weaker than that of the present invention. In comparative example 2, a carbazole derivative is introduced, and the electron-rich effect of carbazole itself will weaken the overall electron transport performance of the molecule, so the overall performance is not as good as the material of the present invention. The difference between comparative example 3 and the present invention is that the fusion direction of benzofuran is inconsistent, and this change in direction affects the change in the electron cloud density of the entire molecule, and then exhibits different electronic properties. In the present invention, the two benzofuran structures are fused in the same direction, so that the electron cloud density in the parent nucleus is superimposed, so that R A After substitution, the molecule as a whole exhibits stronger electron mobility, and its performance is better than that of comparative example 3.

[0279] The applicant declares that the present invention uses the above-mentioned embodiments to illustrate the organic compounds and their applications, and the organic electroluminescent device 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 various 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: Wherein, Ring A is selected from any one of substituted or unsubstituted C6-C60 aromatic rings; The substituents substituted in Ring A are each independently selected from any one of halogen, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, 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; Y1 and Y2 are each independently S or O; X1, X2, X3, X4, X5, X6, X7, and X8 are each independently selected from CR1, CR A or N, and at least one of X1, X2, X3, X4, X5, X6, X7 and X8 is CR A ; R1 is independently selected from hydrogen, halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or Any one of 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; each of the R1s is independently not connected to the adjacent ring structure or is connected to form a ring through a chemical bond; R A It has the structure shown in formula a: Wherein, -* represents the attachment site of the group; L is selected from any one of a single bond, an unsubstituted or R'-substituted C6-C60 arylene group, and an unsubstituted or R'-substituted C3-C60 heteroarylene group; Ar1 and Ar2 are each independently selected from any one of an unsubstituted or R'-substituted C6-C60 aryl group and an unsubstituted or R'-substituted C3-C60 heteroaryl group; R' is independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, or a combination of at least two thereof; each of the R's is independently not connected to an adjacent ring structure or is connected to form a ring by a chemical bond.

2. The organic compound according to claim 1, characterized in that The organic compound has a structure as shown in Formula II: Among them, X9, X 10 , X 11 , X 12 Each independently selected from CR2; R2 is each independently selected from hydrogen, halogen, unsubstituted or R'substituted C1-C20 straight or branched alkyl, unsubstituted or R'substituted C3-C20 cycloalkyl, unsubstituted or R'substituted C2-C20 alkenyl, unsubstituted or R'substituted C1-C20 alkoxy, unsubstituted or R'substituted C1-C20 alkylsilyl, unsubstituted or R'substituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or Any one of 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; each of the R2s is independently not connected to the adjacent ring structure or is connected to form a ring through a chemical bond; Y1, Y2, X1, X2, X3, X4, X5, X6, X7, and X8 have the same defined ranges as in Formula I.

3. The organic compound according to claim 1 or 2, characterized in that At least one of Y1 and Y2 is O.

4. The organic compound according to claim 1 or 2, characterized in that The X1, X2, X3, X4, X5, X6, X7, and X8 are each independently selected from CR1 or CR A , and at least one of them is CR A ; Preferably, one and only one of X1, X2, X3, X4, X5, X6, X7 and X8 is CR A .

5. The organic compound according to claim 1 or 2, characterized in that One of X2, X3, X6 or X7 is CR A .

6. The organic compound according to any one of claims 1 to 5, characterized in that The R1 is selected from any one of hydrogen, cyano, unsubstituted or R'-substituted C1-C10 straight or branched alkyl, unsubstituted or R'-substituted C3-C10 cycloalkyl, unsubstituted or R'-substituted C6-C20 aryl, and unsubstituted or R'-substituted C3-C20 heteroaryl, preferably hydrogen.

7. The organic compound according to any one of claims 2 to 5, characterized in that The R2 is selected from any one of hydrogen, cyano, unsubstituted or R'-substituted C1-C10 straight or branched alkyl, unsubstituted or R'-substituted C3-C10 cycloalkyl, unsubstituted or R'-substituted C6-C20 aryl, and unsubstituted or R'-substituted C3-C20 heteroaryl, preferably hydrogen.

8. The organic compound according to any one of claims 1 to 5, characterized in that The L is selected from any one of a single bond, an unsubstituted or R'-substituted C6-C30 arylene group, and an unsubstituted or R'-substituted C3-C30 heteroarylene group, preferably any one of a single bond, an unsubstituted or R'-substituted C6-C13 arylene group, and an unsubstituted or R'-substituted C5-C20 heteroarylene group; Preferably, L is selected from any one of the following groups which are single bonds, unsubstituted or R'-substituted: Wherein, -* represents the attachment site of the group; Z1 is selected from O, S, CR 11 R 12 or NR 13 Any of the following: R 11 , R 12 , R 13 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-C10 alkenyl group, a C6-C30 aryl group, and a C3-C30 heteroaryl group; 11 and R 12 Not connected or connected into rings by chemical bonds; Preferably, Z1 is O or S; Preferably, L is selected from any one of the following groups which are single bonds, unsubstituted or R'-substituted: More preferably, a single bond, 9. The organic compound according to claim 8, characterized in that The L is selected from any one of the following groups which are single bonds, unsubstituted or R'substituted: -* represents the attachment site of the group; Preferably, L is selected from a single bond, Any one of .

10. The organic compound according to any one of claims 1 to 5, characterized in that The Ar1 and Ar2 are each independently selected from any one of unsubstituted or R'-substituted C6-C30 aryl groups, and unsubstituted or R'-substituted C3-C30 heteroaryl groups; R' is each independently selected from any one of halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl groups, or a combination of at least two thereof; the R' is each independently not connected to adjacent ring structures or connected to form a ring through chemical bonds; Preferably, Ar1 and Ar2 are each independently selected from any one of the following groups which are unsubstituted or R'-substituted: Wherein, -* represents the attachment site of the group; Z2 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-C10 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.

11. The organic compound according to claim 10, characterized in that The Ar1 and Ar2 are each independently selected from any one of the following groups which are unsubstituted or R'-substituted: Further preferred is any one of the following groups which are unsubstituted or R'-substituted: Preferably, Z2 is O, S or CR 21 R 22 ; Preferably, the R 21 , R 22 Each is independently selected from any one of C1-C10 straight or branched alkyl, C6-C20 aryl; Preferably, the R' is independently selected from any one or a combination of at least two of halogen, cyano, nitro, hydroxyl, amino, C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C6-C30 aryl, and C3-C30 heteroaryl; and the R' is independently not connected to the adjacent ring structure or is connected to form a ring through a chemical bond.

12. The organic compound according to claim 10, characterized in that The Ar1 and Ar2 are each independently selected from any one of the following groups which are unsubstituted or R'-substituted: Preferably, Ar1 and Ar2 are each independently selected from any one of the following groups which are unsubstituted or R'-substituted: Wherein, -* represents the attachment site of the group; Preferably, Ar1 and Ar2 are each independently selected from any one of the following groups which are unsubstituted or R'-substituted:

13. The organic compound according to claim 1, characterized in that The organic compound has a structure shown in any one of the following N1-N631:

14. Use of an organic compound as claimed in any one of claims 1 to 13, 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.

15. 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 13; 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 13; Preferably, the light-emitting layer comprises a host material and a doping material, and the host material comprises at least one organic compound as described in any one of claims 1 to 13; Preferably, the host material comprises a combination of a first host material and a second host material, and the first host material comprises the organic compound according to any one of claims 1 to 13; Preferably, the second host material has a structure as shown in Formula IV: Wherein, Ar3, Ar4, and Ar5 are each independently selected from any one of a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C3-C60 heteroaryl group; Ar3, Ar4, and Ar5 are not connected or are connected to form a ring through a chemical bond; The substituents substituted in Ar3, Ar4 and Ar5 are each independently selected from any one or a combination of at least two of halogen, C1-C20 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; In Ar3, Ar4, and Ar5, the substituted substituents are each independently not connected to the adjacent ring structure or are connected to form a ring through a chemical bond; Preferably, the mass ratio of the first host material to the second host material is (0.1-2):

1.

16. A display device, characterized in that: The display device comprises the organic electroluminescent device as claimed in claim 15 .

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