Organic compound, electroluminescent material and application thereof

Abstract

The invention provides an organic compound, an electroluminescent material and application of the organic compound, the organic compound has a structure as shown in a formula I. Through design of a molecular structure, the organic compound has a specific spatial configuration, the overall energy level of molecules is effectively regulated and controlled, and the organic compound is endowed with a relatively low and appropriate LUMO energy level. The organic compound is high in electron mobility and excellent in electron injection and transmission performance, has excellent physical and thermodynamic properties and photoelectric properties, is used for the organic electroluminescent device, can serve as a luminescent layer main body material, has excellent carrier transmission performance, can remarkably prolong the service life of the device, and enables the device to have better comprehensive performance.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic electroluminescent materials, and in particular relates to an organic compound, an electroluminescent material and applications thereof. Background Art

[0002] In recent years, optoelectronic devices based on organic materials have developed rapidly and have become a research hotspot in the field. Examples of organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors (FETs), organic photovoltaic cells (OPCs), and organic sensors. OLEDs have developed particularly rapidly and have achieved commercial success in the information display field. OLEDs can produce highly saturated red, green, and blue colors. Full-color displays made with them require no additional backlight source and offer advantages such as vibrant colors, thinness, and flexibility.

[0003] The core of an OLED device 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). When power is applied, electrons and holes are injected and transported to the light-emitting region, where they recombine, generating excitons and emitting light.

[0004] Current OLEDs can be divided into fluorescent luminescence, phosphorescent luminescence, thermally excited delayed fluorescence and thermally excited sensitized fluorescence according to the luminescence mechanism. Common fluorescent luminophores mainly utilize 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, platinum complexes, etc.) can simultaneously utilize triplet excitons and singlet excitons to emit light, and are called phosphorescent luminophores. Their energy conversion efficiency can be increased by up to 4 times that of traditional fluorescent luminophores. 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 luminophore through energy transfer, which can also achieve higher luminescence efficiency.

[0005] Although products using OLED technology have been commercialized, there is still a need to continuously improve device performance, such as lifespan and efficiency, to meet people's pursuit of high-quality display effects. Therefore, the field urgently needs to develop more diverse and higher-performance organic materials. Their application in organic electroluminescent devices can enable devices to achieve better luminescence and longer lifespan. Summary of the Invention

[0006] In view of the shortcomings of the prior art, the purpose of the present invention is to provide an organic compound, an electroluminescent material and its application. Through the design of the molecular structure, the organic compound has excellent photoelectric properties. It is applied to organic electroluminescent devices and is particularly suitable as the main material of the light-emitting layer, which can effectively improve the life of the device.

[0007] In order to achieve the purpose of the invention, 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, the dotted line represents a single bond or no connection; when the dotted line represents a single bond, it means that the rings are connected to form a ring by a single bond (forming a silcyclopentadiene structure); when the dotted line represents no connection, the chemical bond shown by the dotted line does not exist; when the same description is involved below, it has the same meaning and will not be repeated one by one.

[0011] In Formula I, Z1, Z2, and Z3 are each independently selected from CH or N, and at least one of Z1, Z2, and Z3 is N.

[0012] In Formula I, Ar1 is selected from any one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group.

[0013] In formula I, Ar2 is selected from any one of the following groups:

[0014]

[0015] represents the attachment site of the group; Y is O or S.

[0016] In Formula I, L1, L2, and L3 are each independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; when L1 is a single bond, it represents that Ar1 and the nitrogen six-membered ring where Z1 is located are directly connected by a single bond; the same applies to the description of L2 and L3 being single bonds, and they are not explained one by one.

[0017] R1, R2, R3, R4, R5, and R6 are each independently selected from any one of deuterium, halogen, cyano, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 arylamino, and substituted or unsubstituted C3-C30 heteroarylamino.

[0018] The substituents substituted in Ar1, L1, L2, L3, R1, R2, R3, R4, R5 and R6 are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C1-C20 alkoxy, C2-C20 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C3-C30 arylamino and C3-C30 heteroarylamino.

[0019] In the present invention, the "substituted or unsubstituted" group may be substituted with one or more substituents. When there are multiple substituents (at least two), they may be the same or different. The same expressions used below have the same meaning. Unless otherwise specified, the range of substituents is as shown above and will not be repeated here.

[0020] m1, m2, m3, and m4 represent the number of substituents R1, R2, R3, and R4, respectively; m5 and m7 represent the number of substituents R5; and m6 and m8 represent the number of substituents R6.

[0021] m1, m2, m3, and m8 are each independently selected from integers of 0-5, for example, 0, 1, 2, 3, 4, or 5; m4 and m7 are each independently selected from integers of 0-4, for example, 0, 1, 2, 3, or 4; m5 is selected from integers of 0-3, for example, 0, 1, 2, or 3; m6 is selected from integers of 0-6, for example, 0, 1, 2, 3, 4, 5, or 6.

[0022] It should be noted that when m1 is 0, the number of R1s is zero. In this case, the benzene rings connected to R1s do not contain any substituents and are all CH. When m1 ≥ 2, multiple R1s can be the same or different groups. The same applies to m2, m3, m4, m5, m6, m7, and m8. For the sake of brevity, they are not explained one by one.

[0023] The organic compound provided by the present invention has a structure shown in Formula I. The molecule contains an electron-withdrawing nitrogen six-membered ring, and the ring is respectively connected to a phenyl silicon group with a characteristic structure, an oxygen / sulfur fused ring structure Ar2, and an aromatic group Ar1. Through the design of the molecular structure, in particular, the introduction of a heterocycle with a low triplet energy level, the overall energy level of the molecule is effectively regulated, and a low and suitable LUMO energy level is given to it, so that the electron mobility of the organic compound is high, the electron injection and transport performance is excellent, and it has excellent physical thermodynamic properties and photoelectric properties. It is used in organic electroluminescent devices and can be used as the main material of the light-emitting layer, significantly improving the life of the device and achieving a better luminescence effect.

[0024] It should be noted that, while the potential effects of various groups / features are described separately for ease of explanation, this does not imply that these groups / features function in isolation. In fact, excellent performance is essentially the result of the optimized combination of the entire molecule and the synergistic effects of the various groups, rather than the effects of any single group.

[0025] 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.

[0026] It should be noted that, according to the definition of the dotted line in the present invention, the silicon-containing group in Formula I (and Formula IIA and Formula IIB herein) has any one of the following four structures:

[0027] Represents the connection site between the group and L3.

[0028] In the present invention, the halogen may be fluorine, chlorine, bromine or iodine. The following descriptions of the same elements have the same meanings.

[0029] 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.

[0030] In the present invention, unless otherwise specified, the heteroatom in the heteroaryl group is selected from N, O, S, P, B, Si or Se, preferably N, O or S. The heteroatom in the heterocycloalkyl group is selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0031] 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.

[0032] In the present invention, “*” indicates the attachment site of the group.

[0033] In the present invention, the expression Ca-Cb represents that the number of carbon atoms in the group is ab. Unless otherwise specified, the number of carbon atoms does not include the number of carbon atoms in the substituent.

[0034] In the present invention, “each independently” means that when there are multiple subjects, they may be the same or different.

[0035] The C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0036] The C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0037] The C1-C30 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C22, C24, C26 or C28, etc.

[0038] 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.

[0039] The C2-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0040] 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.

[0041] 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.

[0042] The C3-C60 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.

[0043] In the present invention, the C6-C30 aryl group, C6-C60 aryl group, preferably C6-C25 aryl group, further preferably C6-C20 aryl group, includes monocyclic aryl group and condensed ring aryl group; the monocyclic aryl group means that the group contains at least one phenyl group, when containing at least two phenyl groups, the phenyl groups are connected by a single bond, illustratively including but not limited to: phenyl, biphenyl, terphenyl, quaterphenyl, etc.; the condensed ring aryl group means that the group contains at least two aromatic rings, and the aromatic rings are The groups that share two adjacent carbon atoms fused to each other include, but are not limited to, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives (9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirobifluorenyl, benzofluorenyl, etc.), fluoranthenyl, triphenylene, pyrenyl, perylene, It should be noted that monocyclic aromatic groups and condensed aromatic groups connected by a single bond also fall within the scope of aromatic groups, such as phenylnaphthyl, naphthylphenyl, naphthylnaphthyl, phenylnaphthylphenyl, etc.

[0044] The C3-C30 heteroaryl group, C3-C60 heteroaryl group, preferably C3-C20 heteroaryl group, includes a monocyclic heteroaryl group or a condensed ring heteroaryl group. The monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, etc.), the heteroaryl group and the other group are connected by a single bond, and illustratively include but are not limited to: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, bipyridyl, phenylpyridyl, pyridylphenyl, etc. The fused-ring heteroaryl group refers to a group containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring) in the molecule, and the two share two adjacent atoms fused to each other, including but not limited to: quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, isobenzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl and its derivatives (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolecarbazolyl, azacarbazolyl, etc.), acridinyl, phenothiazinyl, phenoxazinyl, hydroacridinyl, etc. It should be noted that heteroaryl groups and heteroaryl groups connected by a single bond, and aryl groups and heteroaryl groups connected by a single bond also fall within the scope of heteroaryl groups, for example, phenyldibenzofuranyl, phenyldibenzothienyl, dibenzofuranylphenyl, dibenzothienylphenyl, etc.

[0045] In the present invention, the C6-C30 arylene group is a divalent group obtained by removing one H atom from the above-mentioned aryl groups; the C3-C30 heteroarylene group is a divalent group obtained by removing one H atom from the above-mentioned heteroaryl groups.

[0046] In the present invention, the C6-C30 aryloxy group is a monovalent group formed by connecting the above-mentioned aryl groups with O, and the C3-C30 heteroaryloxy group is a monovalent group formed by connecting the above-mentioned heteroaryl groups with O.

[0047] 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-mentioned aryl group. 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-mentioned heteroaryl group.

[0048] The C1-C30 straight chain or branched chain alkyl group, C1-C20 straight chain or branched chain alkyl group, preferably C1-C16 straight chain or branched chain alkyl group, further preferably C1-C10 straight chain or branched chain alkyl group, further preferably C1-C6 straight chain or branched chain alkyl group, illustratively include but are 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.

[0049] Specific examples of the C1-C20 alkoxy group include monovalent groups obtained by connecting the above-mentioned linear or branched alkyl groups to O.

[0050] A specific example of the C1-C20 alkylamino group is a monovalent group in which at least one hydrogen atom in -NH2 is replaced by a linear or branched alkyl group as described above. A specific example of the C1-C20 alkylsilyl group is a monovalent group in which at least one hydrogen atom in -SiH3 is replaced by a linear or branched alkyl group as described above.

[0051] The C3-C30 cycloalkyl group, C3-C20 cycloalkyl group, preferably C3-C10 cycloalkyl group, includes monocyclic alkyl groups or polycyclic alkyl groups. A monocyclic alkyl group refers to an alkyl group containing a single cyclic structure, and a polycyclic alkyl group refers to a structure composed of two or more cycloalkyl groups sharing one or more ring carbon atoms. Exemplary groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl groups.

[0052] Specific examples of the C2-C20 heterocycloalkyl group include monovalent groups formed by replacing one of the ring carbon atoms in the above cycloalkyl group with a heteroatom, wherein the heteroatom is preferably N, O or S.

[0053] The C2-C20 alkenyl group, which contains at least one C=C, illustratively includes but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0054] In formula I of the present invention, Z1, Z2, and Z3 are each independently selected from CH or N, and the number of N in Z1, Z2, and Z3 can be 1, 2, or 3. Preferably, Z1, Z2, and Z3 are all N, and the organic compound contains a triazine ring.

[0055] Preferably, the organic compound has a structure as shown in Formula IIA or Formula IIB:

[0056]

[0057]

[0058] Among them, L1, L2, L3, Ar1, R1, R2, R3, R4, R5, R6, m1, m2, m3, m4, m5, m6, m7, and m8 have the same limited ranges as above.

[0059] Preferably, Ar1 is selected from any one of the following substituted or unsubstituted groups:

[0060]

[0061] in, Represents the attachment site of the group.

[0062] X1 is selected from O, S, CR 11 R 12 or NR 13 Any one of .

[0063] R A 、R 11 、R 12 、R 13Each is independently selected from any one of hydrogen, 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-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28, etc.) aryl, C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28, etc.) heteroaryl; the R 11 and R 12 Not connected or connected to form a ring through chemical bonds.

[0064] Preferably, the R 11 、R 12 、R 13 Each is independently selected from any one of C1-C6 straight chain or branched alkyl, C2-C6 alkenyl, and C6-C20 aryl, and is more preferably any one of C1-C5 straight chain or branched alkyl, phenyl, biphenyl, terphenyl, and naphthyl.

[0065] Preferably, the R 11 and R 12 Not connected or connected by chemical bonds to form a spirobifluorenyl group.

[0066] Preferably, the R 13 Any one selected from C6-C20 aryl groups, more preferably any one selected from phenyl, biphenyl, terphenyl, and naphthyl.

[0067] Preferably, the R A Any one selected from C1-C6 linear or branched alkyl groups, C6-C20 aryl groups, more preferably any one selected from phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups.

[0068] Preferably, the substituents substituted in Ar1 are each independently selected from deuterium, halogen, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl, C3-C20 (e.g., C3 , C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl or a combination of at least two thereof, and further preferably deuterium, fluorine, C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, furyl, thienyl, pyrrolyl, N-phenylpyrrolyl, benzofuranyl, benzothienyl, indolyl, N-phenylindolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl or a combination of at least two thereof.

[0069] Preferably, Ar1 is selected from any one of the following substituted or unsubstituted groups:

[0070]

[0071] in, Represents the attachment site of the group.

[0072] In the specific structures of Ar1 listed above, one or more (≥2, may be all) H groups may be optionally replaced by D (deuterium).

[0073] Preferably, L1, L2, and L3 are each independently selected from any one of a single bond, a substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) arylene group, and a substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroarylene group.

[0074] Preferably, L1, L2, and L3 are each independently selected from any one of the following groups:

[0075] in, Represents the attachment site of the group.

[0076] X2 is selected from O, S, CR21 R 22 or NR 23 Any one of .

[0077] R 21 、R 22 、R 23 Each is independently selected from any one of hydrogen, 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-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28, etc.) aryl, C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28, etc.) heteroaryl; the R 21 and R 22 Not connected or connected to form a ring through chemical bonds.

[0078] Preferably, the R 21 、R 22 、R 23 Each is independently selected from any one of C1-C6 straight chain or branched alkyl, C2-C6 alkenyl, and C6-C20 aryl, and is more preferably any one of C1-C5 straight chain or branched alkyl, phenyl, biphenyl, terphenyl, and naphthyl.

[0079] Preferably, X2 is O or S.

[0080] Preferably, L1, L2, and L3 are each independently selected from any one of the following groups:

[0081]

[0082] in, Represents the attachment site of the group.

[0083] In the specific structures of L1, L2, and L3 listed above, one or more (≥2, may be all) H may be optionally replaced by D (deuterium).

[0084] Preferably, R1, R2, R3, R4, R5, and R6 are each independently selected from any one of deuterium, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) linear or branched alkyl, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) aryl, substituted or unsubstituted C3-C20 heteroaryl, and substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl.

[0085] Preferably, R1, R2, R3, R4, R5, and R6 are each independently selected from deuterium, substituted or unsubstituted C1-C3 straight chain alkyl, Represents the attachment site of the group.

[0086] Further preferably, in the present invention, the substituents substituted in Ar1, L1, L2, L3, R1, R2, R3, R4, R5, and R6 are each independently selected from deuterium, halogen, cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight or branched alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) aryl, C3-C20 (for example, C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, any one or a combination of at least two thereof, further preferably deuterium, fluorine, C1-C6 straight or branched alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, furyl, thienyl, pyrrolyl, N-phenylpyrrolyl, benzofuranyl, benzothienyl, indolyl, N-phenylindolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl or a combination of at least two thereof.

[0087] Preferably, the organic compound has a structure shown in any one of the following N1-N163:

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099] It should be noted that the expressions N57, N58, and N59 represent that all H in the compound are replaced by D.

[0100] In a second aspect, the present invention provides a use of the organic compound according to the first aspect, wherein the organic compound is used in an organic electronic device.

[0101] 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.

[0102] Preferably, the organic compound is used in an organic electroluminescent device.

[0103] Further preferably, the organic compound is applied to a red organic electroluminescent device.

[0104] Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device.

[0105] Preferably, the organic compound is used as a host material of a light-emitting layer in an organic electroluminescent device, and more preferably as a host material of a red light-emitting layer.

[0106] The organic compound of the present invention is used as a light-emitting layer material. It is an electronic host material with a low triplet energy pole and is particularly suitable as a red light-emitting layer host material. It has good luminescence performance and is conducive to improving the service life of the device.

[0107] In a third aspect, the present invention provides an electroluminescent material, comprising a combination of a first host material and a second host material; the first host material comprises at least one of the organic compounds described in the first aspect, and the second host material is an aromatic amine compound.

[0108] In the present invention, the organic compound having the structure shown in Formula I is used as the first host material, which has excellent electron transport properties; the second host material is an aromatic amine compound, which has excellent hole injection and transport properties. The two host materials are compounded with each other, so that the electroluminescent material is used in an organic electroluminescent device and can be used as a dual host material in the light-emitting layer, which can effectively regulate the injection / transport balance of holes and electrons, promote the transport balance of carriers, and facilitate the location of the electron and hole recombination center in the light-emitting layer to occur at the center of the light-emitting layer, avoiding the offset of the light-emitting recombination interface, thereby significantly improving the life of the device and improving the overall performance of the device.

[0109] Preferably, the second host material has a structure as shown in Formula III:

[0110]

[0111] In formula III, 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; and Ar3, Ar4, and Ar5 are each independently not connected or connected to form a ring through chemical bonds.

[0112] It should be noted that when Ar3, Ar4, and Ar5 are not connected, that is, the second host material of the structure represented by Formula III is a triarylamine compound. For example, Ar3 and Ar4 are chemically bonded to form a ring, that is, a carbazole-derived fused ring structure is formed between Ar3, Ar4, and the N atom.

[0113] The substituents substituted by Ar3, Ar4 and Ar5 are each independently selected from any one of deuterium, halogen, C1-C20 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, thiol, 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. A combination of at least two of them.

[0114] Preferably, the mass ratio of the first main material to the second main 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 further preferably (0.5-1.5):1.

[0115] In a fourth aspect, the present invention provides an organic electroluminescent device, comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises at least one of the organic compound described in the first aspect and the electroluminescent material described in the third aspect.

[0116] Preferably, the organic layer includes a light-emitting layer, and the light-emitting layer includes at least one of the organic compound described in the first aspect and the electroluminescent material described in the third aspect.

[0117] Preferably, the light-emitting layer comprises a host material and a dopant material, and the host material comprises at least one of the organic compound described in the first aspect and the electroluminescent material described in the third aspect.

[0118] Preferably, the light-emitting layer comprises a host material and a dopant material, and the host material comprises at least one of the organic compound described in the first aspect and the electroluminescent material described in the third aspect.

[0119] Preferably, the doping material (also called "dye", "guest material", "dopant") is a phosphorescent doping material, more preferably a red phosphorescent doping material.

[0120] Preferably, based on the mass of the main material being 100%, the mass of the doping material is 1-10%, for example, 2%, 3%, 4%, 5%, 6%, 7%, 8% or 9%.

[0121] Preferably, based on 100% by mass of the electroluminescent material, the mass of the doping material is 1-10%, for example, 2%, 3%, 4%, 5%, 6%, 7%, 8% or 9%.

[0122] Preferably, the organic layer further includes a hole transport region and an electron transport region.

[0123] 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.

[0124] 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.

[0125] Optionally, the electron transport layer comprises at least one organic compound described in the first aspect; and / or the hole blocking layer comprises at least one organic compound described in the first aspect.

[0126] In a preferred embodiment, the organic electroluminescent device (OLED device) includes a first electrode, a second electrode, and an organic layer located between the electrodes. The organic layer can be divided into multiple regions, such as a hole transport region, a light-emitting layer, and an electron transport region; the light-emitting layer comprises at least one of the organic compound and electroluminescent material provided by the present invention.

[0127] In a preferred technical solution, the organic electroluminescent device includes a first electrode, multiple light-emitting functional layers (organic layers), and a second electrode arranged in sequence; the organic layers include a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer arranged in sequence, with the hole injection layer in contact with the first electrode (anode). The organic layer (preferably the light-emitting layer) comprises at least one of the organic compound and electroluminescent material provided by the present invention.

[0128] In a preferred embodiment, a substrate can be used below the first electrode or above the second electrode. The substrate is made of glass or a polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. Furthermore, the substrate used for the display can also be provided with thin-film transistors (TFTs).

[0129] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode serves as an anode, transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), and any combination thereof can be used. When the first electrode serves as a cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) can be used, as well as any combination thereof.

[0130] The organic layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic layer can be an organic small molecule, an organic macromolecule or a polymer, or a combination thereof.

[0131] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including single-layer hole transport layers containing only one compound and single-layer hole transport layers containing multiple compounds. The hole transport region can also be a multilayer structure comprising at least one of the following: a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.

[0132] The material of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, wherein the aromatic amine derivatives include the compounds shown below as HT-1 to HT-51; or any combination thereof.

[0133]

[0134]

[0135]

[0136]

[0137] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can use one or more of the compounds HT-1 to HT-51 described above, or one or more of the compounds HI-1 to HI-3 described below. Alternatively, one or more of the compounds HT-1 to HT-51 can be doped with one or more of the compounds HI-1 to HI-3 described below.

[0138]

[0139] The light-emitting layer includes a luminescent dye (i.e., dopant) that can emit light of different wavelengths and a host material (host). The light-emitting layer can be a single-color light-emitting layer that emits a single color, such as red, green, or blue. Multiple single-color light-emitting layers of different colors can be arranged in a planar pattern according to a pixel pattern, or they can be stacked together to form a multi-color light-emitting layer. When light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single-color light-emitting layer that can simultaneously emit different colors, such as red, green, and blue.

[0140] Depending on the technology, the light-emitting layer material can be made of fluorescent electroluminescent materials, phosphorescent electroluminescent materials, thermally activated delayed fluorescence materials, and other materials. An OLED device can use a single light-emitting technology or a combination of multiple technologies. These different light-emitting materials, categorized by technology, can emit light of the same color or different colors.

[0141] In one aspect of the present invention, the light-emitting layer utilizes phosphorescent electroluminescence technology. The host material of the light-emitting layer comprises the electroluminescent material provided by the present invention, i.e., a combination of a first host material and a second host material, wherein the first host material comprises at least one organic compound having a structure represented by Formula I.

[0142] The second host material is an aromatic amine compound having a structure shown in Formula III; specifically, the second host material can be selected from, but not limited to, one or more combinations of the following specific compounds H1-H28.

[0143]

[0144]

[0145]

[0146] 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.

[0147]

[0148]

[0149] 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 can be one or more compounds selected from HT-1 to HT-51, but is not limited thereto.

[0150] The OLED organic material layer may also include an electron transport region between the light-emitting layer and the cathode. This region may be a single-layer electron transport layer (ETL), including those containing only one compound and those containing multiple compounds. The region may also be a multilayer structure comprising at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0151] The OLED organic layer may also include an electron transport region (ETR) between the light-emitting layer and the cathode. This ETR can be a single-layer ETL, including those containing only one compound and those containing multiple compounds. The ETR can also be a multilayer structure comprising at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0152] 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.

[0153]

[0154]

[0155]

[0156]

[0157] 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 can be made of, but is not limited to, one or more compounds of the above ET-1 to ET-73.

[0158] The device may further include an electron injection layer located between the electron transport layer and the cathode. The electron injection layer material includes, but is not limited to, one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, and Yb.

[0159] In a fifth aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the fourth aspect.

[0160] Preferably, the display device includes a display screen or a display panel.

[0161] The present invention further provides an electronic device, comprising the aforementioned display device.

[0162] Compared with the prior art, the present invention has the following beneficial effects:

[0163] The organic compound provided by the present invention has a structure shown in Formula I. Through the design of the molecular structure, it has a specific spatial configuration, effectively regulating the overall energy level of the molecule, and giving it a low and suitable LUMO energy level. The organic compound has high electron mobility, excellent electron injection and transport performance, excellent physical thermodynamic properties and photoelectric properties. It is used in organic electroluminescent devices and can be used as a main material for the light-emitting layer. It has excellent carrier transport performance, can significantly improve the life of the device, and make the device have better overall performance. BRIEF DESCRIPTION OF THE DRAWINGS

[0164] Figure 1 This is the X-ray diffraction result of the intermediate S5-3 provided in Preparation Example 5. DETAILED DESCRIPTION

[0165] The technical solution of the present invention is further described below by way of specific embodiments. It should be understood by those skilled in the art that the embodiments are merely to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0166] In a specific embodiment, the organic compound can be prepared by the following representative synthetic route:

[0167]

[0168] Wherein, Z1, Z2, Z3, L1, L2, L3, Ar1, Ar2, R1, R2, R3, R4, m1, m2, m3, and m4 have the same definitions as in Formula I; Hal1 and Hal2 are each independently selected from any one of F, I, Br, and Cl; U1 and U2 are each independently selected from Reaction I and reaction II are carried out in the presence of a palladium catalyst; the order of reaction I and reaction II can be adjusted according to the synthesis situation, that is, reaction I can be carried out first and then reaction II, or reaction II can be carried out first and then reaction I.

[0169] In one embodiment, U2 is The structure of raw material S is It can be prepared by the following representative synthetic route:

[0170]

[0171] Wherein, Hal3, Hal4, and Hal5 are each independently selected from any one of F, I, Br or Cl; preferably, Hal3 is Br, Hal4 is F, and Hal5 is Cl.

[0172] It should be noted that obtaining the organic compound is not limited to the synthesis method and raw materials used in the present invention. Those skilled in the art can also make routine adjustments to the preparation method according to actual needs, or can choose other methods or routes to obtain the organic compound proposed in the present invention. Organic compounds represented by Formula I synthesized by those skilled in the art using other methods also fall within the scope of protection of the present invention.

[0173] The specific preparation method of the organic compound of the present invention will be described in detail below using a number of preparation examples and synthesis examples, but the preparation method of the present invention is not limited to these synthesis examples.

[0174] The compounds, solvents and reagents used in the synthesis methods not mentioned in the present invention are all raw materials obtained through commercial channels and can be purchased from the domestic chemical product market or prepared in-house using these raw materials according to known methods.

[0175] The mass spectrometric data (MS, m / z) of the intermediates and target products described in the following embodiments of the present invention were obtained by liquid chromatography-mass spectrometry (LC-MS / MS) (Agilent 6530 LC / Q-TOF, ESI+APCI ion source), specifically M+H. Compounds with the same molecular weight but different substitution sites were identified by reference to HPLC peak times and the use of different starting materials to confirm structural accuracy.

[0176] Preparation Example 1: Preparation of Intermediate S1

[0177]

[0178] 1-Bromo-8-naphthol (0.3 mol), 2-fluoro-5-chloro-phenylboronic acid (0.31 mol), potassium carbonate (0.4 mol), tetrakis(triphenylphosphine)palladium (0.003 mol), water (50 mL) and dioxane (600 mL) were added to a reaction flask and heated to 90°C for 6 h. The reaction was monitored by thin layer chromatography (TLC) to ensure completion. Water and dichloromethane were added for extraction. The organic phase was separated and concentrated to obtain intermediate S1-1.

[0179] Add intermediate S1-1 (0.2 mol), cesium carbonate (0.4 mol), and N,N-dimethylformamide (DMF) (600 mL) to a reaction flask. Heat to 130°C with stirring for 5 h. Monitor the reaction for completion by TLC. Extract with brine and ethyl acetate, and concentrate the organic phase to obtain intermediate S1-2.

[0180] Intermediate S1-2 (0.15 mol), pinacol diboron (0.2 mol), potassium acetate (0.25 mol), tris(dibenzylacetone)dipalladium (0.0015 mol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.003 mol) and dioxane (500 mL) were added to a reaction flask and heated to 90° C. for 6 h. The reaction was complete under TLC monitoring. Water and dichloromethane were added for extraction. The organic phase was separated and concentrated to obtain intermediate S1 (MS=345.2).

[0181] Preparation Example 2-4: Preparation of Intermediates S2, S3, and S4

[0182] The 2-fluoro-5-chloro-phenylboronic acid in Preparation Example 1 was replaced by an equal molar amount of Other raw materials, steps and process parameters were the same as those in Preparation Example 1 to obtain intermediates S2, S3 and S4.

[0183]

[0184] Preparation Example 5: Preparation of Intermediate S5

[0185]

[0186] 1-Bromo-8-naphthol (0.3 mol), 2-fluoro-phenylboronic acid (0.31 mol), potassium carbonate (0.4 mol), tetrakis(triphenylphosphine)palladium (0.003 mol), water (50 mL) and dioxane (600 mL) were added to a reaction flask, heated to 90°C for 6 h, and the reaction was completed after TLC monitoring. Water and dichloromethane were added for extraction, and the organic phase was separated and concentrated to obtain intermediate S5-1.

[0187] Intermediate S5-1 (0.2 mol), cesium carbonate (0.4 mol), and DMF (600 mL) were added to a reaction flask and heated to 130°C with stirring for 5 h. The reaction was complete when monitored by TLC. Brine and ethyl acetate were added for extraction, and the organic phase was concentrated to obtain intermediate S5-2.

[0188] Intermediate S5-2 (0.15 mol) and DMF (600 mL) were added to a reaction flask. The mixture was cooled to -10°C with stirring and allowed to react. A solution of N-bromosuccinimide (NBS, 0.16 mol) in DMF was then added dropwise. After the addition was complete, the mixture was incubated for 2 hours. Completion of the reaction was monitored by gas chromatography-mass spectrometry (GC-MS). Brine and ethyl acetate were added for extraction, and the organic phase was concentrated to obtain intermediate S5-3.

[0189] The structure of intermediate S5-3 was verified by X-ray diffractometer (XRD, model Synergy-R, Rigaku), and the obtained X-ray diffraction results are shown in FIG Figure 1 As shown, from Figure 1 It can be seen that the product prepared by the present invention is consistent with the target structure, and the Br atom is connected to a specific position of the fused ring.

[0190] Intermediate S5-3 (0.1 mol), pinacol diboron (0.12 mol), potassium acetate (0.15 mol), 1,1-bis(diphenylphosphino)ferrocenepalladium dichloride (0.001 mol) and dioxane (400 mL) were added to a reaction flask and heated to 90°C for 6 h. The reaction was completed under TLC monitoring. Water and dichloromethane were added for extraction. The organic phase was separated and concentrated to obtain intermediate S1 (MS=345.2).

[0191] Synthesis Example 1: Preparation of Organic Compound N1

[0192]

[0193] Raw material M1 (0.02 mol), pinacol diboron (0.022 mol), potassium acetate (0.025 mol), 1,1-bis(diphenylphosphino)ferrocenepalladium dichloride (0.0001 mol) and dioxane (200 mL) were added to a reaction flask, heated to 90°C for 5 h, and the reaction was complete under TLC monitoring. Water and dichloromethane were added for extraction, and the organic phase was separated and concentrated to obtain intermediate N1-A.

[0194] Intermediate N1-A (0.015 mol), 2,4-dichloro-6-phenyl-1,3,5-triazine (P1, 0.015 mol), potassium carbonate (0.02 mol), tetrakis(triphenylphosphine)palladium (0.00015 mol), water (20 mL) and dioxane (200 mL) were added to a reaction flask, heated to 100 ° C. for 3 h, and the reaction was completed after TLC monitoring. Water and dichloromethane were added for extraction. The organic phase was separated and concentrated, washed with 100 ml of ethanol, and then filtered to obtain intermediate N1-B.

[0195] Intermediate N1-B (0.005 mol), S3 (0.005 mol), potassium carbonate (0.006 mol), tetrakis(triphenylphosphine)palladium (0.05 mmol), water (3 mL) and dioxane (80 mL) were added to a reaction flask and heated to 100°C for 3 h. A large amount of solid precipitated from the reaction system. The reaction was complete as monitored by TLC. The reaction liquid was directly filtered, the filter cake was dried, 50 times the amount of xylene was added, heated under reflux to dissolve, and then filtered while hot. The filtrate was allowed to stand for crystallization, and N1 (MS: 708.2) was obtained by filtration.

[0196] Synthesis example 2-15

[0197] The process route of Synthesis Example 2-15 is the same as that of Synthesis Example 1, except that different raw materials are used. The raw materials, target compounds and mass spectrum data (measured values) are shown in Table 1; in Table 1, the raw material M is Raw material P is Intermediate S is the intermediate S1-S5 obtained in Preparation Examples 1-5.

[0198] Table 1

[0199]

[0200]

[0201]

[0202]

[0203]

[0204] Synthesis Example 16: Preparation of Organic Compound N60

[0205]

[0206] Intermediate S1-2 (0.02 mol) and DMF (100 mL) were added to a reaction flask. The mixture was cooled to -10°C with stirring and then a solution of NBS (0.025 mol) in DMF was added dropwise. After the addition was complete, the mixture was incubated for 2 hours. Completion of the reaction was monitored by GC-MS. Brine and ethyl acetate were added for extraction, and the organic phase was concentrated to obtain intermediate S6-A.

[0207] Intermediate S6-A (0.014 mol), phenylboronic acid (0.018 mol), potassium carbonate (0.02 mol), tetrakis(triphenylphosphine)palladium (0.0002 mol), water (10 mL) and dioxane (100 mL) were added to a reaction flask and heated to 100°C for 3 h. The reaction was completed after TLC monitoring. After cooling, water and dichloromethane were added for extraction. The organic phase was concentrated, washed with ethanol, and filtered to obtain S6-B.

[0208] Intermediate S6-B (0.012 mol), pinacol diboron (0.015 mol), potassium acetate (0.016 mol), tris(dibenzylacetone)dipalladium (0.00012 mol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.00024 mol) and dioxane (100 mL) were added to a reaction flask and heated to 100° C. for 8 h. The reaction was complete after TLC monitoring. Water and dichloromethane were added for extraction. The organic phase was separated and concentrated to obtain intermediate S6 (MS=421.2).

[0209] Intermediate S6 (0.01 mol), N1-B (0.01 mol, prepared by the same method as in Synthesis Example 1), potassium carbonate (0.012 mol), tetrakis(triphenylphosphine)palladium (0.00012 mol), water (10 mL) and dioxane (100 mL) were added to a reaction flask and heated to 100° C. for 5 h. The reaction was completed under TLC monitoring. After cooling, a large amount of solid precipitated. The reaction solution was directly filtered, and the filter cake was washed once with water and once with ethanol, and then recrystallized from toluene to obtain N60 (MS=784.3).

[0210] Synthesis Example 17: Preparation of Organic Compound N144

[0211]

[0212] Raw material M19 (0.05 mol), 3-chlorophenylboronic acid (0.05 mol), potassium carbonate (0.055 mol), tetrakistriphenylphosphine palladium (0.0005 mol), water (20 mL) and dioxane (200 mL) were added to a reaction flask and heated to 100°C for 3 h. The reaction was monitored to be complete by TLC. After cooling, water and dichloromethane were added for extraction. The organic phase was concentrated, washed with ethanol, and filtered to obtain N144-A.

[0213] Intermediate N144-A (0.045 mol), pinacol diboron (0.05 mol), potassium acetate (0.055 mol), tris(dibenzylacetone)dipalladium (0.00045 mol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.0009 mol) and dioxane (300 mL) were added to a reaction flask and heated to 100°C for 8 h. The reaction was complete after TLC monitoring. Water and dichloromethane were added for extraction. The organic phase was separated and concentrated to obtain intermediate N144-B.

[0214] Intermediate N144-B (0.03 mol), P1 (0.03 mol), potassium carbonate (0.035 mol), tetrakis(triphenylphosphine)palladium (0.00035 mol), water (20 mL) and dioxane (200 mL) were added to a reaction flask and heated to 90°C for 5 h. The reaction was completed after TLC monitoring. After cooling, water and dichloromethane were added for extraction. The organic phase was concentrated, washed with ethanol and filtered to obtain N144-C.

[0215] Intermediate N144-C (0.015 mol), S1 (0.015 mol), potassium carbonate (0.02 mol), tetrakis(triphenylphosphine)palladium (0.00015 mol), water (15 mL) and dioxane (150 mL) were added to a reaction flask and heated to 90°C for 8 h. The reaction was complete under TLC monitoring. After cooling, solid precipitated. The reaction solution was directly filtered, and the filter cake was washed once with water and once with ethanol, and then recrystallized from toluene to obtain N144 (MS=784.3).

[0216] Synthesis Example 18: Preparation of Organic Compound N57

[0217]

[0218] N64 (0.01 mol), benzene-d6 (perdeuterated benzene, 10 mol), and trifluoromethanesulfonic acid (0.1 mol) were added to a reaction flask and heated to 70°C for 16 h. The reaction was stopped when the molecular weight was 741.24 as monitored by liquid chromatography-mass spectrometry (LC-MS). After cooling, an aqueous solution of potassium phosphate was added to the reaction solution, the pH was adjusted to neutral, and the organic phase was separated and concentrated to obtain N57.

[0219] The present invention exemplifies a specific synthesis method of an intermediate (intermediate S) and an example of synthesizing the organic compound of the present invention by coupling reaction of a triazine raw material (raw material P) with the intermediate S and the raw material M. For other compounds for which no specific synthesis method is given, they can also be prepared by similar methods by simply replacing the raw materials. These will not be described in detail here, or those skilled in the art can also prepare them by other methods in the prior art.

[0220] Example 1

[0221] 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 specific preparation method is as follows:

[0222] (1) A glass plate coated with an ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone / ethanol, 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;

[0223] (2) Place the glass plate with the ITO anode in a vacuum chamber and evacuate to a vacuum of <1×10 -5 Pa, a mixture of compound HT-29:HI-1 (97 / 3, w / w) was vacuum-deposited on the above-mentioned anode layer as a hole injection layer at a deposition rate of 0.1 nm / s and a deposition film thickness of 10 nm;

[0224] (3) Vacuum evaporation of 60 nm of compound HT-29 as a hole transport layer on the hole injection layer at a deposition rate of 0.1 nm / s;

[0225] (4) Vacuum evaporation of 60 nm of compound HT-37 on the hole transport layer as an electron blocking layer at a deposition rate of 0.1 nm / s;

[0226] (5) Vacuum evaporation of a light-emitting layer on the electron blocking layer, the light-emitting layer comprising a mixture of a host material and a doping material (dye, RPD-18), the mass ratio (w / w) of the host material to the doping material being 100:3; the host material being a combination of the organic compound N1 (first host material) and the compound H26 (second host material) provided by the present invention, the mass ratio of N1 to H25 being 1:1; the dual-source co-evaporation method was used for evaporation, the evaporation rate being 0.1 nm / s, and the total film thickness being 40 nm;

[0227] (6) Vacuum-deposit 5 nm of compound ET-17 on the light-emitting layer as the hole blocking layer of the device at a deposition rate of 0.1 nm / s;

[0228] (7) A mixture of compounds ET-66:ET-57 (50 / 50, w / w) was vacuum-deposited on the hole-blocking layer as an electron transport layer at a deposition rate of 0.1 nm / s and a film thickness of 25 nm;

[0229] (8) Vacuum evaporation of 1 nm of LiF compound on the electron transport layer as an electron injection layer at a deposition rate of 0.1 nm / s;

[0230] (9) Vacuum-evaporating metal aluminum with a thickness of 150 nm on the electron injection layer as a cathode at a deposition rate of 1 nm / s to obtain the organic electroluminescent device.

[0231] Examples 2-26, Comparative Examples 1-8

[0232] An organic electroluminescent device differs from Example 1 only in that the host material of the light-emitting layer is replaced with the materials listed in Tables 2 and 3; all other layers, thicknesses, materials, and preparation methods are the same as in Example 1. In Tables 2 and 3, the mass ratio of the first host material to the second host material is 1:1.

[0233] The structure of the first host material in each comparative example is as follows:

[0234]

[0235] The performance test of the organic electroluminescent device is carried out as follows:

[0236] The brightness of the organic electroluminescent device was measured using a luminance meter from 10000 cd / m 2 Attenuation to 9700cd / m 2 The time taken to complete the test is recorded as the life of the device (LT97);

[0237] In Table 2, the life test value of Comparative Example 1 is recorded as 1.0, and the ratio of the life test values ​​of other devices to the test value of Comparative Example 1 is calculated;

[0238] Table 2

[0239]

[0240]

[0241] Table 3

[0242] Device First main material Second main material LT97 life (h) Example 22 N64 H2 82 Comparative Example 4 Ref-1 H2 50 Example 23 N64 H9 86 Comparative Example 5 Ref-1 H9 53 Example 24 N64 H13 109 Comparative Example 6 Ref-1 H13 91 Example 25 N64 H15 92 Comparative Example 7 Ref-1 H15 64 Example 26 N64 H17 129 Comparative Example 8 Ref-1 H17 108

[0243] Furthermore, the HOMO, LUMO energy levels, and low-temperature PL luminescence performance of the first host material were tested as follows:

[0244] (1)HOMO energy level, LUMO energy level

[0245] Cyclic voltammetry was performed on the main material to be tested using an electrochemical workstation. The workstation used a three-electrode system with a platinum electrode as the working electrode, a platinum wire electrode as the counter electrode, and an Ag wire electrode as the reference electrode. 0.5 g of the sample to be tested was dissolved in 5 mL of ultra-dry tetrahydrofuran. Tetrabutylammonium perchlorate was used as the electrolyte salt. The test sample was protected by nitrogen. The voltage range was -2 V to 2 V, the scan rate was 100 mV / s, and the number of scans was 2. On the CV curve, the peak value, i.e., the oxidation potential E, was read. ox and the reduction potential E red , according to the same settings as above, test the oxidation potential E of ferrocene Fe Calculated HOMO = -((E ox -E Fe )+4.8), LUMO=-((E red -E Fe )+4.8).

[0246] (2) Low-temperature PL luminescence performance

[0247] Dissolve 0.1 mg of the sample to be tested in 10 mL of 2-methyltetrahydrofuran, dilute 10-fold, and place in a quartz tube for testing. Use a Hitachi F-7000 fluorescence photometer for testing. Place a Dewar flask on the sample holder and pour liquid nitrogen into the Dewar flask, ensuring that the liquid nitrogen can submerge the sample in the quartz tube. Place the sample in the Dewar flask and wait 2-3 minutes to ensure that the sample is completely frozen. Select the phosphorescence mode on the instrument and delay the test for 5 seconds. After the test is completed, the peak emission value is the low-temperature phosphorescence PL value of the sample.

[0248] The obtained data are shown in Table 4:

[0249] Table 4

[0250] Compound number HOMO(eV) LUMO(eV) Low temperature PL (nm) N64 -5.52 -2.59 567 Ref-1 -6.09 -2.63 456

[0251] The test data in Tables 2 and 3 indicate that the organic compounds provided herein, as host materials for the light-emitting layer of organic electroluminescent devices, can significantly improve device lifespan. In particular, compared to the comparative compounds Ref-1, Ref-2, and Ref-3, Examples 1-21 of the present invention exhibit outstanding lifespan advantages, with improvements of ≥30%, ranging from 30% to 180%. Table 3 also demonstrates that the organic compounds described herein exhibit similarly good lifespan advantages when used with other types of hole-type hosts, demonstrating the broad compatibility of the organic compounds provided herein.

[0252] The only difference between the present invention and Ref-1 is the different substituents. As can be seen from Table 4, the organic compound N64 and Ref-1 have a slightly shallower LUMO energy level and a lower triplet energy level (low-temperature PL, i.e., E=hc / λ, and the triplet energy level is inversely proportional to the wavelength). The emission wavelength of the guest in the red light device is generally around 620-630nm. In order to ensure the effective energy transfer between the host and the guest, the host energy needs to be at least 30nm higher than the guest to prevent energy backtransmission, but the higher the better. The higher the energy level, the host material needs to withstand higher energy. When the device is lit for a long time, the host material is bound to partially decompose at high energy, resulting in a faster lifespan decay. The present invention regulates the overall energy level of the molecule by introducing a low triplet energy level heterocyclic group Ar2 with a specific structure, so that it has a lower and usable energy level, which is one of the reasons why its lifespan is higher than Ref-1. Moreover, the LUMO energy level of the organic compound N64 is also significantly shallower than that of the comparative compound Ref-1, indicating that the six-membered heterocyclic fused structure Ar2 of the present invention has a lower electron mobility than the dibenzofuran structure in the comparative compound, which is just able to adapt to the high electron mobility characteristics of the silicon group, making its carriers more balanced. This is the second reason why the lifetime is higher than that of the comparative compound Ref-1, and the same is true for Ref-2. The introduction of the six-membered heterocyclic fused structure in the comparative compound Ref-3 reduces the electron mobility, but there is no silicon-based strong electron mobility group in the structure, resulting in carrier imbalance when adapted to the hole-type host, causing the light-emitting composite interface to shift to the transport layer, resulting in a lower lifetime.

[0253] The applicant states that while the above-described embodiments illustrate the organic compounds, electroluminescent materials, and their applications, the present invention is not limited to the aforementioned process steps, nor does it necessarily rely on these process steps for implementation. Persons skilled in the art will appreciate that any improvements to the present invention, equivalent substitutions for the raw materials used, additions of auxiliary components, and selection of specific methods, etc., fall within the scope of protection and disclosure 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 dashed line represents a single bond or no connection; Z1, Z2, and Z3 are each independently selected from CH or N, and at least one of Z1, Z2, and Z3 is N; Ar1 is selected from any one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group; Ar2 is selected from any one of the following groups: represents the attachment site of the group; Y is O or S; L1, L2, and L3 are each independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; R1, R2, R3, R4, R5, and R6 are each independently selected from any one of deuterium, halogen, cyano, substituted or unsubstituted C1-C30 linear or branched alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 arylamino, and substituted or unsubstituted C3-C30 heteroarylamino; The substituents substituted in Ar1, L1, L2, L3, R1, R2, R3, R4, R5, and R6 are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C1-C20 alkoxy, C2-C20 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C3-C30 arylamino, and C3-C30 heteroarylamino; m1, m2, m3, and m8 are each independently selected from integers of 0-5, m4 and m7 are each independently selected from integers of 0-4, m5 is selected from integers of 0-3, and m6 is selected from integers of 0-6.

2. The organic compound according to claim 1, characterized in that The organic compound has a structure as shown in Formula IIA or Formula IIB: Among them, L1, L2, L3, Ar1, R1, R2, R3, R4, R5, R6, m1, m2, m3, m4, m5, m6, m7, and m8 have the same defined ranges as in claim 1.

3. The organic compound according to claim 1 or 2, characterized in that The Ar1 is selected from any one of the following substituted or unsubstituted groups: in, The attachment site of the representative group; X1 is selected from O, S, CR 11 R 12 or NR 13 Any of the following; R A 、R 11 、R 12 、R 13 Each is independently selected from any one of hydrogen, C1-C10 straight or branched alkyl, C2-C10 alkenyl, C6-C30 aryl, and C3-C30 heteroaryl; the R 11 and R 12 Not connected or connected to form a ring through chemical bonds; Preferably, the substituents in Ar1 are each independently selected from any one or a combination of at least two of deuterium, halogen, C1-C10 linear or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C20 aryl, and C3-C20 heteroaryl.

4. The organic compound according to claim 1 or 2, characterized in that The Ar1 is selected from any one of the following substituted or unsubstituted groups: in, Represents the attachment site of the group.

5. The organic compound according to claim 1 or 2, characterized in that The L1, L2, and L3 are each independently selected from any one of a single bond, a substituted or unsubstituted C6-C20 arylene group, and a substituted or unsubstituted C3-C20 heteroarylene group; Preferably, L1, L2, and L3 are each independently selected from any one of the following groups: in, The attachment site of the representative group; X2 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 of hydrogen, C1-C10 straight or branched alkyl, C2-C10 alkenyl, C6-C30 aryl, and C3-C30 heteroaryl; the R 21 and R 22 Not connected or connected to form a ring through chemical bonds.

6. The organic compound according to claim 1 or 2, characterized in that R1, R2, R3, R4, R5, and R6 are each independently selected from any one of deuterium, substituted or unsubstituted C1-C10 linear or branched alkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, and substituted or unsubstituted C3-C10 cycloalkyl; Preferably, R1, R2, R3, R4, R5, and R6 are each independently selected from deuterium, substituted or unsubstituted C1-C3 straight chain alkyl, Represents the attachment site of the group.

7. The organic compound according to claim 1 or 2, characterized in that The organic compound has a structure shown in any one of the following N1-N163:

8. Use of the organic compound according to any one of claims 1 to 7, characterized in that: The organic compound is applied to organic electronic devices; Preferably, the organic compound is used in an organic electroluminescent device; Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device.

9. An electroluminescent material, characterized in that The electroluminescent material includes a combination of a first host material and a second host material; the first host material includes at least one of the organic compounds according to any one of claims 1 to 7, and the second host material is an aromatic amine compound.

10. The electroluminescent material according to claim 9, characterized in that The second host material has a structure as shown in Formula III: 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; and Ar3, Ar4, and Ar5 are each independently not connected or connected to form a ring through a chemical bond; The substituents substituted by Ar3, Ar4 and Ar5 are each independently selected from any one of deuterium, halogen, C1-C20 straight or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, thiol, 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. A combination of at least two of them.

11. The electroluminescent material according to claim 9 or 10, characterized in that The mass ratio of the first host material to the second host material is (0.1-2):1, preferably (0.5-1.5):

1.

12. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises at least one of the organic compound according to any one of claims 1 to 7 and the electroluminescent material according to any one of claims 9 to 11; Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one of the organic compound according to any one of claims 1 to 7 and the electroluminescent material according to any one of claims 9 to 11; Preferably, the light-emitting layer comprises a host material and a dopant material, and the host material comprises at least one of the organic compound according to any one of claims 1 to 7 and the electroluminescent material according to any one of claims 9 to 11.

13. A display device, characterized in that: The display device comprises the organic electroluminescent device according to claim 12.

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