Organic compound, organic electroluminescent material and application thereof

Abstract

The application provides an organic compound, an organic electroluminescent material and application thereof. The organic compound has a structure shown in the following formula I. The organic compound provided by the application is used as a host material of a light-emitting layer, so that the electron and hole transport in the host material has good balance, and the HOMO energy level and the LUMO energy level of the organic compound are matched with adjacent hole transport layers and electron transport layers, so that the OLED device has a smaller driving voltage, higher light-emitting efficiency and longer service life.

Description

Technical Field

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

[0002] Compared to traditional light-emitting technologies, OLED devices offer numerous advantages, including low driving voltage, high luminous efficiency, high contrast, high color saturation, wide viewing angle, and fast response time. They hold great potential to replace mainstream liquid crystal displays (LCDs) and become a star technology in the display field. The growing demand in the display field has also driven the rapid development of OLED device structures and organic optoelectronic materials. This is reflected in the continuous emergence of compounds and materials with new structures, functional groups, and substituents. Furthermore, OLED device structures have been continuously optimized, evolving from the initial sandwich structure to a complex structure composed of multiple functional layers.

[0003] Today's OLED devices include a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron-transporting material, an electron-injecting material, and a hole-blocking material. The host material in the light-emitting layer is a key factor affecting the luminous efficiency and performance of OLED devices. Summary of the Invention

[0004] In response to the shortcomings of the prior art, the present invention aims to provide an organic compound, an organic electroluminescent material, and their applications. The organic compound provided by the present invention is used as the host material of the light-emitting layer of an organic light-emitting device, which can reduce the device driving voltage and improve the device's luminous efficiency and lifespan.

[0005] In order to achieve the purpose of the invention, the present invention adopts the following technical solutions:

[0006] In a first aspect, the present invention provides an organic compound having a structure shown in Formula I below:

[0007]

[0008] wherein X1 is selected from a single bond and X2 is selected from an oxygen atom; or X1 is selected from an oxygen atom and X2 is selected from a single bond;

[0009] R1-R 12each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 (for example, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) straight or branched alkyl, C1-C30 (for example, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) wherein one or more methylene groups are substituted with -O- or -S- in a non-adjacent O or S atom C2-C30 (for example, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) alkyl, substituted or unsubstituted C2-C30 (for example, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) alkenyl, C2-C30 (for example, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.) alkenyl, substituted or unsubstituted C7-C60 (for example, C7, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.) aralkyl, substituted or unsubstituted C6-C60 (for example, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.), substituted or unsubstituted C3-C60 (for example, C3, C4, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54,C56, C58, C60, etc.) heteroaryl, substituted or unsubstituted C4-C60 (for example, C4, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.) heteroaralkyl, substituted or unsubstituted C3-C30 (for example, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) cycloalkyl, substituted or unsubstituted C3-C30 (for example, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) heterocycloalkyl, substituted or unsubstituted C3-C30 (for example, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) heterocycloalkyl, substituted or unsubstituted C3-C30 (for example, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C any one of C27, C28, C29, C30, etc.) cycloalkenyl groups; or, two adjacent groups among R1, R2, R3, R4, R5, R6, R7, and R8 are linked to form a C6-C30 (for example, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) aryl group.

[0010] In the present invention, the substituents of the substituted aryl, substituted alkyl, substituted alkenyl, substituted aralkyl, substituted heteroaryl, substituted heteroaralkyl, substituted cycloalkyl, substituted heterocycloalkyl, and substituted cycloalkenyl are each independently selected from deuterium, cyano, halogen, C1-C30 (for example, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, C31, C32, C33, C34, C35, C36, C37, C38, C39, C40, C41, C42, C43, C44, C45, C46, ​​C47, C48, C49, C50, C51, C52, C53, C54, C55, C56, C57, C58, C59, C60, C61, C62, C63, C64, C65, C66, C67, C68, C69, C70, C71, C72, C73, C74, C75, C76, C77, C78, ​​C79, C80, C81, C82, C83, C84, C85, C86, C87, C88 C6, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) straight chain or branched alkyl, C3-C30 (for example, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) C3, C24, C25, C26, C27, C28, C29, C30, etc.) cycloalkyl, C6-C60 (for example, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C any one or a combination of at least two of C3-C60 (for example, C3, C4, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.) heteroaryl.

[0011] Preferably, the C1-C30 straight-chain or branched alkyl group is selected from any one of methyl, ethyl or tert-butyl, or a combination of at least two of them.

[0012] Preferably, the C3-C30 cycloalkyl group is selected from any one of cyclopropane, cyclohexane or adamantane, or a combination of at least two of them.

[0013] Preferably, the substituents of the substituted aryl, substituted alkyl, substituted alkenyl, substituted aralkyl, substituted heteroaryl, substituted heteroaralkyl, substituted cycloalkyl, substituted heterocycloalkyl and substituted cycloalkenyl are each independently selected from the group consisting of deuterium, cyano, halogen, phenyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothiophene, fluorenyl, 9,9'-dimethylfluorenyl, difluorenyl, 9,9'-diphenylfluorenyl, benzonaphthofuranyl, benzonaphthothiophene, carbazolyl, benzocarbazolyl, dibenzofuran-substituted phenyl or dibenzothiophene-substituted phenyl, or a combination of at least two thereof.

[0014] In the present invention, the R1-R 12 Each is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, and substituted or unsubstituted quinazolinyl.

[0015] Preferably, the substituents in the substituted pyrimidinyl, substituted triazinyl and substituted quinazolinyl are each independently selected from deuterium, cyano, halogen, C1-C30 (for example, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C C24, C25, C26, C27, C28, C29, C30, etc.) straight chain or branched alkyl, C3-C30 (for example, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28 , C29, C30, etc.) cycloalkyl, C6-C60 (for example, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.) aryl or C3- any one or a combination of at least two of C60 (for example, C3, C4, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.) heteroaryl groups.

[0016] In the present invention, at least one of R1-R12 is selected from substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazoline;

[0017] The substituents in the substituted pyrimidinyl, substituted triazinyl and substituted quinazolinyl are each independently selected from deuterium, cyano, halogen, C1-C30 (for example, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) straight chain or branched alkyl, C3-C30 (for example, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C C29, C30, etc.) cycloalkyl, C6-C60 (for example, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.), aryl or C3-C C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.) heteroaryl groups or a combination of at least two thereof.

[0018] Preferably, any one of R1-R12 is selected from substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazoline, and the remaining groups in R1-R12 are selected from hydrogen;

[0019] The substituents in the substituted pyrimidinyl, substituted triazinyl and substituted quinazolinyl are each independently selected from deuterium, cyano, halogen, C1-C30 (for example, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) straight chain or branched alkyl, C3-C30 (for example, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C C29, C30, etc.) cycloalkyl, C6-C60 (for example, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.), aryl or C3-C C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.) heteroaryl groups or a combination of at least two thereof.

[0020] Preferably, R1 is selected from substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazoline, R2-R 12 selected from hydrogen;

[0021] The substituents in the substituted pyrimidinyl, substituted triazinyl and substituted quinazolinyl are each independently selected from deuterium, cyano, halogen, C1-C30 (for example, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) straight chain or branched alkyl, C3-C30 (for example, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C C29, C30, etc.) cycloalkyl, C6-C60 (for example, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.), aryl or C3-C C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.) heteroaryl groups or a combination of at least two thereof.

[0022] Preferably, R2 is selected from substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazoline, R1, R3-R 12 selected from hydrogen;

[0023] The substituents in the substituted pyrimidinyl, substituted triazinyl and substituted quinazolinyl are each independently selected from deuterium, cyano, halogen, C1-C30 (for example, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) straight chain or branched alkyl, C3-C30 (for example, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C C29, C30, etc.) cycloalkyl, C6-C60 (for example, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.), aryl or C3-C C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.) heteroaryl groups or a combination of at least two thereof.

[0024] Preferably, R3 is selected from substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazoline, R1-R2, R4-R 12 selected from hydrogen;

[0025] each of the substituents in the substituted pyrimidinyl, substituted triazinyl, substituted quinazolinyl is independently selected from deuterium, cyano, halogen, C1-C30 (e.g., can be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) straight or branched chain alkyl, C3-C30 (e.g., can be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) cycloalkyl, C6-C60 (e.g., can be C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, C58, C60, etc.) aryl, or C3-C60 (e.g., can be C3, C4, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, C58, C60, etc.) heteroaryl, or a combination of at least two of any of the foregoing.

[0026] Preferably, R4 is selected from substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, R1-R3, R5-R 12 selected from hydrogen;

[0027] The substituents in the substituted pyrimidinyl, substituted triazinyl and substituted quinazolinyl are each independently selected from deuterium, cyano, halogen, C1-C30 (for example, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) straight chain or branched alkyl, C3-C30 (for example, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C C29, C30, etc.) cycloalkyl, C6-C60 (for example, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.), aryl or C3-C C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.) heteroaryl groups or a combination of at least two thereof.

[0028] Preferably, R5 is selected from substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazoline, R1-R4, R6-R 12 selected from hydrogen;

[0029] The substituents in the substituted pyrimidinyl, substituted triazinyl and substituted quinazolinyl are each independently selected from deuterium, cyano, halogen, C1-C30 (for example, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) straight chain or branched alkyl, C3-C30 (for example, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C C29, C30, etc.) cycloalkyl, C6-C60 (for example, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.), aryl or C3-C C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.) heteroaryl groups or a combination of at least two thereof.

[0030] Preferably, R6 is selected from substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazoline, R1-R5, R7-R 12 selected from hydrogen;

[0031] The substituents in the substituted pyrimidinyl, substituted triazinyl and substituted quinazolinyl are each independently selected from deuterium, cyano, halogen, C1-C30 (for example, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) straight chain or branched alkyl, C3-C30 (for example, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C C29, C30, etc.) cycloalkyl, C6-C60 (for example, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.), aryl or C3-C C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.) heteroaryl groups or a combination of at least two thereof.

[0032] Preferably, R7 is selected from substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazoline, R1-R6, R8-R 12 selected from hydrogen;

[0033] The substituents in the substituted pyrimidinyl, substituted triazinyl and substituted quinazolinyl are each independently selected from deuterium, cyano, halogen, C1-C30 (for example, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) straight chain or branched alkyl, C3-C30 (for example, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C C29, C30, etc.) cycloalkyl, C6-C60 (for example, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.), aryl or C3-C C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.) heteroaryl groups or a combination of at least two thereof.

[0034] Preferably, R8 is selected from substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazoline, R1-R7, R9-R 12 selected from hydrogen;

[0035] The substituents in the substituted pyrimidinyl, substituted triazinyl and substituted quinazolinyl are each independently selected from deuterium, cyano, halogen, C1-C30 (for example, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.) straight chain or branched alkyl, C3-C30 (for example, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C C29, C30, etc.) cycloalkyl, C6-C60 (for example, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.), aryl or C3-C C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.) heteroaryl groups or a combination of at least two thereof.

[0036] In the present invention, two adjacent groups among R1, R2, R3, R4, R5, R6, R7 and R8 are connected to form a benzene ring.

[0037] Preferably, R7 and R8 are connected to form a benzene ring.

[0038] Preferably, R6 and R7 are connected to form a benzene ring.

[0039] Preferably, R5 and R6 are connected to form a benzene ring.

[0040] Preferably, R3 and R4 are connected to form a benzene ring.

[0041] Preferably, R2 and R3 are connected to form a benzene ring.

[0042] Preferably, R1 and R2 are connected to form a benzene ring.

[0043] In the present invention, the substituted pyrimidinyl, substituted triazine and substituted quinazoline are each independently selected from any one of the following structures:

[0044]

[0045]

[0046] in, Indicates the attachment site of a group.

[0047] In the present invention, the organic compound is selected from any one of the following N-1 to N-384:

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070] In a second aspect, the present invention provides an organic electroluminescent material. The organic electroluminescent material includes the organic compound described in the first aspect.

[0071] In a third aspect, the present invention provides an organic electroluminescent device, comprising an anode, a cathode, and an organic thin film layer located between the anode and the cathode, wherein the organic thin film layer comprises the organic compound described in the first aspect or the organic electroluminescent material described in the second aspect.

[0072] Preferably, the organic thin film layer includes any one of a hole injection layer, a hole transport layer, a luminescence auxiliary layer, a luminescent layer, a hole blocking layer, an electron buffer layer, an electron transport layer, an electron buffer layer or an electron injection layer, or a combination of at least two thereof.

[0073] Preferably, the light-emitting layer comprises the organic compound as described in the first aspect.

[0074] Preferably, the light-emitting layer comprises a host material and a guest material, and the host material comprises the organic compound as described in the first aspect.

[0075] Preferably, the hole blocking layer comprises the organic compound as described in the first aspect.

[0076] Preferably, the electron transport layer comprises the organic compound as described in the first aspect.

[0077] In a fourth aspect, the present invention provides an electronic device comprising the organic electroluminescent device according to the third aspect.

[0078] Preferably, the electronic device includes any one of an optical fiber, a lighting device, an electrophotographic photoreceptor, a photoelectric converter, an organic solar cell, a switching element, an organic light-emitting field-effect transistor, an image sensor or a dye laser.

[0079] Compared with the prior art, the present invention has the following beneficial effects:

[0080] (1) The organic compound provided by the present invention has a suitable rigid structure, high molecular stability, good film-forming properties, a high thermal decomposition temperature, and high thermal stability, thereby improving the luminous efficiency and luminous performance of the device;

[0081] (2) The organic compound provided by the present invention is used as the main material of the light-emitting layer, so that the electron and hole transport in the main material have a good balance. At the same time, the HOMO energy level and LUMO energy level of the organic compound match the adjacent hole transport layer and electron transport layer, so that the OLED device has a smaller driving voltage, higher luminous efficiency and life.

[0082] Explanation of terms

[0083] Definition of device terms

[0084] As used in the present invention, the term "organic electroluminescent compound" means a compound that can be used in an organic electroluminescent device and can be contained in any layer constituting the organic electroluminescent device as needed.

[0085] As used in the present invention, the term "organic electroluminescent material" refers to a material that can be used in an organic electroluminescent element and that can include at least one compound. If necessary, the organic electroluminescent material can be included in any layer constituting the organic electroluminescent element. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, an electron blocking material, a luminescence auxiliary material, a light-emitting layer material (including a host material and a doping material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0086] The organic electroluminescent material of the present disclosure may include at least one compound represented by Formula I. Although not limited thereto, the compound having the structure represented by Formula I may be included in the light-emitting layer. In this case, the compound having the structure represented by Formula I may be included as a host. If desired, the host material may include two or more compounds having the structure represented by Formula I. If desired, the host material may further include another compound. Moreover, the compound having the structure represented by Formula I may be included in the electron transport region, and / or the compound having the structure represented by Formula I may be included in the electron buffer layer, and is not limited thereto.

[0087] Hereinafter, each layer of the organic electroluminescent device comprising the compound having the structure represented by formula I of the present invention will be described.

[0088] substrate

[0089] Organic EL devices are generally fabricated on a light-transmitting substrate that supports the organic EL device. The light-transmitting substrate preferably has a transmittance of 50% or more for light in the visible region of 400-700 nm, and is preferably a smooth substrate.

[0090] Examples of such light-transmitting substrates include glass plates and synthetic resin plates. Examples of glass plates include plates formed from soda-lime glass, barium-strontium-containing glass, lead glass, aluminum silicate glass, borosilicate glass, barium borosilicate glass, and quartz. Examples of synthetic resin plates include plates made of polycarbonate resin, acrylic resin, polyethylene terephthalate resin, polyether sulfide resin, and polysulfone resin.

[0091] anode

[0092] The anode plays the role of injecting holes into the hole transport layer or the light-emitting layer, and it is effective to have a work function of 4 eV or more (preferably 4.45 eV or more). Specific examples of anode materials include carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, and alloys thereof, metal oxides such as tin oxide and indium oxide used in ITO substrates and NESA substrates, and organic conductive resins such as polythiophene or polypyrrole.

[0093] cathode

[0094] As the cathode, a cathode having a metal, alloy, conductive compound or mixture thereof with a small work function (less than 4 eV) can be used as an electrode material. As a specific example of such an electrode material, magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride or the like and their alloys can be used, but they are not particularly limited. As the alloy, representative examples include magnesium / silver, magnesium / indium, lithium / aluminum or the like, but they are not particularly limited. The ratio of the alloy is controlled by the temperature, atmosphere, vacuum degree or the like of the evaporation source, and an appropriate ratio is selected. The anode and the cathode can also be formed by a layer structure of more than two layers as needed.

[0095] light-emitting layer

[0096] The light-emitting layer has the functions of carrier injection, carrier transport, and light emission. The light-emitting layer materials include host materials and guest materials. Guest materials include phosphorescent guest materials, fluorescent guest materials, TADF guest materials, etc.

[0097] Hole injection layer / hole transport layer

[0098] The hole injection layer / hole transport layer is a layer that helps inject holes into the light-emitting layer and transport the holes to the light-emitting area. It has a large hole mobility and an ionization energy that is usually as low as 5.7 eV or less. As such a hole injection layer / hole transport layer, it is preferred that the material transports holes to the light-emitting layer at a lower electric field strength. It is further preferred that the hole mobility is, for example, 10 4 -10 6 When the electric field is 10 V / cm -4 cm 2More than 1 x 10~6cm / Vsec. Examples of materials known as hole-transporting layer materials include bis(N-(1-naphthyl-n-phenyl))benzidine (a-NPD), N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (NPB), or N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), and the like.

[0099] Electron buffer layer

[0100] The electron buffer layer helps to block holes in the light-emitting layer and also helps to transport electrons to the light-emitting layer to promote the combination of electrons and holes in the light-emitting layer, improving light-emitting efficiency.

[0101] Electron injection layer / electron transport layer

[0102] The electron injection layer / electron transport layer is a layer that helps to inject electrons into the light-emitting layer and transport electrons to the light-emitting region, and has a large electron mobility. The adhesion-improving layer is an electron injection layer that contains a material that particularly well adheres to the cathode.

[0103] As a material used in the electron injection layer, specifically, LiF, Liq, Li2O, BaO, NaCl, CsF, and the like can be listed, without particular limitation thereto.

[0104] The functions of the OLED can be achieved by combining the various layers described above, or some layers can be completely omitted. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sub-layers. For example, the light-emitting layer can have two layers of different light-emitting materials to achieve the desired light-emitting spectrum.

[0105] To form each layer of the organic electroluminescent device of the present disclosure, a dry film formation method such as vacuum evaporation, sputtering, plasma, ion plating method, etc., or a wet film formation method such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating method, etc., can be used. The organic electroluminescent compound of the present disclosure can be film-formed by a co-evaporation method or a mixture evaporation method.

[0106] The product is used in optoelectronics, medicine, biotechnology, optical fibers, lighting devices, electrophotographic photoreceptors, photoelectric converters, organic solar cells, switching elements, organic light-emitting field effect transistors, image sensors, or dye lasers.

[0107] Definitions of terms for substituents

[0108] As used in the present invention, the term "halogen" can include fluorine, chlorine, bromine, or iodine.

[0109] As used herein, the term "C1-C30 alkyl" refers to a monovalent substituent derived from a straight-chain or branched saturated hydrocarbon having 1 to 30 carbon atoms, examples of which include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0110] As used in the present invention, the term "C3-C30 cycloalkyl" refers to a group derived from a monocyclic hydrocarbon or a polycyclic hydrocarbon having 1 to 30 ring main chain carbon atoms, and the cycloalkane may include cyclopropyl, cyclobutyl, adamantyl, and the like.

[0111] As used in the present invention, the term "C3-C30 heterocycloalkyl" refers to a group derived from a monocyclic hydrocarbon or polycyclic hydrocarbon having 1 to 30 ring main chain carbon atoms, wherein at least one carbon atom is replaced by a heteroatom, and the heteroatom is selected from at least one of O, S, N, Si, and P, preferably O, S, and N. In addition, the heterocycloalkyl group may be optionally substituted.

[0112] As used herein, the term "C2-C30 alkenyl" refers to and includes straight-chain and branched alkenyl groups. Alkenyl groups are essentially alkyl groups that include at least one carbon-carbon double bond in the alkyl chain. Cycloalkenyl groups are cycloalkyl groups that include at least one carbon-carbon double bond in the cycloalkyl ring.

[0113] In the present invention, aryl and arylene groups include monocyclic, polycyclic or condensed ring aromatic groups, and the rings may be interrupted by short non-aromatic units and may contain spiro structures, including but not limited to phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, anthracenyl, fluorenyl, spirobifluorenyl, etc.

[0114] In the present invention, the heteroaryl and heteroarylene groups include monocyclic, polycyclic or condensed-ring heteroaryl groups, wherein the rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen and sulfur. Including but not limited to furyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and derivatives thereof.

[0115] As used herein, the term "substituted" refers to a hydrogen atom in a compound being replaced by another substituent. The position is not limited to a specific position, as long as the hydrogen at that position can be replaced by a substituent. When two or more substituents are present, the two or more substituents may be the same or different.

[0116] As used herein, unless otherwise specified, hydrogen atoms include protium, deuterium, and tritium.

[0117] In the present invention, the definition of the group defines the range of the number of carbon atoms, and the number of carbon atoms is any integer within the defined range. For example, a C6-C60 aromatic group represents an aromatic group, and the number of carbon atoms can be any integer within the range of 6-60, such as 6, 8, 10, 15, 20, 30, 35, 40, 45, 50, 55 or 60.

[0118] In the present invention, a pair of adjacent substituents can be optionally combined or fused to form a ring. Preferred rings are five-, six-, or seven-membered carbocyclic rings, including two cases where a portion of the ring formed by the pair of substituents is saturated and a portion of the ring formed by the pair of substituents is unsaturated. As used herein, "adjacent" means that the two substituents involved can be adjacent to each other on the same ring, or on two adjacent rings with two closest available substitutable positions (e.g., the 2, 2' positions in biphenyl or the 1, 8 positions in naphthalene), as long as they can form a stable fused ring system.

[0119] "Two adjacent groups are connected to form a C6-C30 aromatic group" means that two substituents in adjacent positions in the same ring or adjacent rings can be connected to each other by a chemical bond to form a C6-C30 aromatic group. The present invention does not limit the specific method of connecting to form a ring. When the same description is mentioned below, it has the same meaning.

[0120] In this disclosure, "combination" means that one or more members of an applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can conceive from the list. For example, an alkyl group and a deuterium group can be combined to form a partially or fully deuterated alkyl group; or a halogen, an alkyl group, and an aryl group can be combined to form a haloarylalkyl group. In some embodiments, the combination of substituents comprises a combination of 2-4 groups; in other embodiments, the combination of substituents comprises a combination of 2-3 groups; and in yet other embodiments, the combination of substituents comprises a combination of 2 groups. BRIEF DESCRIPTION OF THE DRAWINGS

[0121] Figure 1 Schematic diagram of the structure of an organic electroluminescent device;

[0122] Among them, 1 is the substrate, 2 is the anode, 3 is the hole injection layer, 4 is the hole transport layer, 5 is the light-emitting layer, 6 is the electron transport layer, 7 is the electron injection layer, and 8 is the cathode.

[0123] The simple layered structures illustrated in the accompanying drawings are provided by way of non-limiting examples, and it will be understood that the embodiments of the present disclosure may be used in conjunction with various other structures. The specific materials and structures described are exemplary in nature, and other materials and structures may be used, functional OLEDs may be obtained by combining the layers described in different ways, or layers may be omitted entirely based on design, performance, and cost factors, and other layers not specifically described may be included, and materials other than those specifically described may be used, and although many of the embodiments provided herein describe various layers as including a single material, it will be understood that combinations of materials may be used, and furthermore, the layers may have various sub-layers. The names given to the various layers herein are not intended to be strictly limiting. For example, the hole transport layer 4 transports holes and injects holes into the emissive layer 5, and may be described as a hole transport layer or a hole injection layer. DETAILED DESCRIPTION

[0124] 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.

[0125] The organic compounds in the following examples were synthesized by conventional methods, including Suzuki reaction, bromination on NBS, and methods reported in the literature, for example, refer to the synthesis method in J.CHEM.SOC.PERKIN TRANS.I 1987, 645-647.

[0126] The organic compounds in the following examples were tested using an SQD2 quadrupole mass spectrometer with an APCI source.

[0127] Preparation Example 1

[0128] This preparation example provides an intermediate 1, and the preparation method of intermediate 1 comprises the following steps:

[0129]

[0130] Synthesis of intermediate 1-1: Raw material 1 (1 mmol) was added to 10 mL (PEG (2 g) -CH2Cl2), followed by the addition of dilute hydrochloric acid (1 mmol, 1 mL), the system was cooled to 0 ° C, and an aqueous solution of sodium nitrite (1 mmol) was slowly added dropwise. After the addition was complete, stirring was continued for 30 minutes, and then cuprous chloride (1 mmol) was added at 0 ° C. After the reaction was completed, a dilute aqueous sodium hydroxide solution was added to the system to remove PEG, extracted with dichloromethane, and dried over anhydrous magnesium sulfate. The crude product was separated by column chromatography (ethyl acetate: n-hexane (volume ratio 1:10)) to obtain intermediate 1-1 (0.1 g, yield 49%);

[0131] MS (APCI) m / z [M+H] + : found: 208.19.

[0132] Synthesis of intermediate 1-2: Intermediate 1-1 (1 mmol), palladium acetate (0.05 mmol), NBS (1.1 mmol) were added to toluene (10 mL) under nitrogen protection, and the mixture was heated to 110 °C for 5 h. After the reaction was completed, the solvent was removed, and the crude product was separated by column chromatography (ethyl acetate: n-hexane (volume ratio 1:10)) to obtain intermediate 1-2 (0.19 g, yield 67%);

[0133] MS (APCI) m / z [M+H]+: found: 286.21.

[0134] Synthesis of intermediate 1-3: Intermediate 1-2 (1 mmol), raw material 2 (1 mmol), tetrakis(triphenylphosphine)palladium (0.05 mmol), tetrabutylammonium bromide (0.05 mmol) and sodium carbonate (2 mmol) were added to toluene (10 mL), ethanol (1 mL) and water (1 mL), and the system was heated to 80 °C for 8 h. After the reaction was completed, the system was cooled to room temperature, water was added, and ethyl acetate was extracted. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed, and the crude product was separated by column chromatography (ethyl acetate: n-hexane (volume ratio 1:10)) to obtain intermediate 1-3 (0.21 g, yield 63%);

[0135] MS (APCI) m / z [M+H]+: found: 335.11.

[0136] Synthesis of intermediate 1-4: Raw material 1 (1 mmol), raw material 2 (1 mmol), cesium carbonate (1 mmol) and copper (I) iodide were added to N,N-dimethylformamide (10 mL), heated to 110 °C, and reacted. After the reaction was completed, water was washed, ethyl acetate was extracted, the organic phase was dried over anhydrous magnesium sulfate, and the organic solvent was removed by rotary evaporation. The crude product was separated by column chromatography (ethyl acetate: n-hexane (volume ratio 1:50)) to obtain intermediate 1-4 (0.23 g, yield 75%);

[0137] MS (APCI) m / z [M+H]+: found: 298.21.

[0138] Synthesis of intermediate 1-5: Intermediate 1-4 (1 mmol) was added to a mixed solution of ethyl acetate and 1,2-dichlorobenzene, and Pd / c (10% Pd) was added under nitrogen protection. The reaction system was stirred at room temperature under 1 atm hydrogen pressure for 2 h. The reaction solution was filtered with diatomite, and the organic solvent was removed by reduced pressure distillation to obtain intermediate 1-5 (0.23 g, yield 86%);

[0139] MS (APCI) m / z [M+H]+: found: 268.24.

[0140] The synthesis of intermediate 1-6 was the same as that of intermediate 1-2, except that intermediate 1-1 was replaced with an equal molar amount of intermediate 1-5 to obtain intermediate 1-6 (0.22 g, yield 64%);

[0141] MS (APCI) m / z [M+H] + : found: 346.41.

[0142] The synthesis of intermediate 1-7 was the same as that of intermediate 1-1, except that the starting material 1 was replaced with an equal molar amount of intermediate 1-6 to obtain intermediate 1-7 (0.19 g, yield 54%).

[0143] MS (APCI) m / z [M+H] + : found: 365.08.

[0144] The synthesis of intermediate 1-8 was the same as that of intermediate 1-3, except that intermediate 1-2 was replaced by an equal molar amount of intermediate 1-7, and raw material 2 was replaced by an equal molar amount of raw material 3 to obtain intermediate 1-8 (0.23 g, yield 60%).

[0145] MS (APCI) m / z [M+H] + : found: 379.32.

[0146] The synthesis of intermediate 1-9 was the same as that of intermediate 1-4, except that intermediate 1-3 was replaced with an equal molar amount of intermediate 1-8 to obtain intermediate 1-9 (0.27 g, yield 79%).

[0147] MS (APCI) m / z [M+H] + : found: 343.26.

[0148] Synthesis of Intermediate 1: Intermediate 1-9 (1 mmol), pinacol diboronate (1.2 mmol), sodium acetate (2 mmol), tris(dibenzylideneacetone)dipalladium (0.05 mmol), and 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (1.5 mmol) were added to 1,4-dioxane (10 mL) and the atmosphere was replaced with nitrogen three times. The reaction was heated to 100°C under nitrogen protection. After the reaction was completed, water was added to quench the reaction, and the mixture was extracted with dichloromethane. The organic solvent was removed by rotary evaporation, and the crude product was separated by column chromatography (ethyl acetate:n-hexane (volume ratio 1:50)) to obtain Intermediate 1 (0.35 g, 82% yield).

[0149] MS (APCI) m / z [M+H] + : found: 435.20.

[0150] Preparation Example 2

[0151] This preparation example provides an intermediate 2, and the preparation method of intermediate 2 comprises the following steps:

[0152]

[0153] The synthesis of intermediate 2-1 was the same as that of intermediate 1-3, except that intermediate 1-2 was replaced by an equal molar amount of intermediate 1-7, and starting material 2 was replaced by an equal molar amount of starting material 4 to obtain intermediate 2-1 (0.24 g, yield 56%).

[0154] MS (APCI) m / z [M+H] + : found: 429.19.

[0155] The synthesis of intermediate 2-2 was the same as that of intermediate 1-4, except that intermediate 1-3 was replaced with an equal molar amount of intermediate 2-1 to obtain intermediate 2-2 (0.30 g, yield 77%);

[0156] MS (APCI) m / z [M+H] + : found: 393.22.

[0157] The synthesis of intermediate 2 was the same as that of intermediate 1, except that intermediate 1-9 was replaced with an equal molar amount of intermediate 2-2 to obtain intermediate 2 (0.40 g, yield 83%).

[0158] MS (APCI) m / z [M+H] + : found: 485.31.

[0159] Preparation Example 3

[0160] This preparation example provides an intermediate 3, and the preparation method of intermediate 3 comprises the following steps:

[0161]

[0162]

[0163] Synthesis of intermediate 3-1: Lead tetroxide (1 mmol) and potassium chloride (1 mmol) were added to raw material 1 (1 mmol), and trifluoroacetic acid (1.1 mmol) was added and stirred until the lead tetroxide was completely dissolved. After the reaction, the system was diluted with water and extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, and the crude product was separated by column chromatography (ethyl acetate:n-hexane (volume ratio 1:50)) to obtain intermediate 3-1 (0.10 g, yield 46%).

[0164] MS (APCI) m / z [M+H] + : found: 223.19.

[0165] Synthesis of intermediate 3-2: Intermediate 3-1 (1 mmol) was added to 10 mL (PEG (2 g) -CH2Cl2), followed by the addition of dilute bromic acid (1 mmol, 1 mL). The system was cooled to 0 ° C, and an aqueous solution of sodium nitrite (1 mmol) was slowly added dropwise. After the addition was complete, stirring was continued for 30 min, and then cuprous bromide (1 mmol) was added at 0 ° C. After the reaction was completed, dilute aqueous sodium hydroxide solution was added to the system to remove PEG, extracted with dichloromethane, and dried over anhydrous magnesium sulfate. The crude product was separated by column chromatography (ethyl acetate: n-hexane (volume ratio 1:10)) to obtain intermediate 3-2 (0.12 g, yield 41%);

[0166] MS (APCI) m / z [M+H] + : found: 286.08.

[0167] The synthesis of intermediate 3-3 was the same as that of intermediate 1-3, except that intermediate 1-2 was replaced with an equal molar amount of intermediate 3-2 to obtain intermediate 3-3 (0.17 g, yield 52%);

[0168] MS (APCI) m / z [M+H] + : found: 334.23.

[0169] The synthesis of intermediate 3-4 was the same as that of intermediate 1-4, except that intermediate 1-3 was replaced with an equal molar amount of intermediate 3-3 to obtain intermediate 3-4 (0.24 g, yield 79%);

[0170] MS (APCI) m / z [M+H] + : found: 298.18.

[0171] The synthesis of intermediate 3-5 was the same as that of 1-5, except that intermediate 1-4 was replaced with an equal molar amount of intermediate 3-4 to obtain intermediate 3-5 (0.22 g, yield 82%);

[0172] MS (APCI) m / z [M+H] + : found: 268.24.

[0173] The synthesis of intermediate 3-6 was the same as that of intermediate 1-2, except that intermediate 1-1 was replaced with an equal molar amount of intermediate 3-5 to obtain intermediate 3-6 (0.21 g, yield 60%);

[0174] MS (APCI) m / z [M+H] + : found: 346.15.

[0175] The synthesis of intermediate 3-7 was the same as that of intermediate 1-1, except that the starting material 1 was replaced with an equal molar amount of intermediate 3-6 to obtain intermediate 3-7 (0.15 g, yield 43%).

[0176] MS (APCI) m / z [M+H]+: found: 365.22.

[0177] The synthesis of intermediate 3-8 was the same as that of intermediate 1-3, except that intermediate 1-2 was replaced by the same molar amount of intermediate 3-2, and raw material 2 was replaced by the same molar amount of raw material 3, to obtain intermediate 3-3 (0.19 g, yield 50%);

[0178] MS (APCI) m / z [M+H]+: found: 379.21.

[0179] The synthesis of intermediate 3-9 was the same as that of intermediate 1-4, except that intermediate 1-3 was replaced by the same molar amount of intermediate 3-8, to obtain intermediate 3-9 (0.28 g, yield 82%);

[0180] MS (APCI) m / z [M+H]+: found: 343.19.

[0181] The synthesis of intermediate 3 was the same as that of intermediate 1, except that intermediate 1-9 was replaced by the same molar amount of intermediate 3-9, to obtain intermediate 3 (0.35 g, yield 81%);

[0182] MS (APCI) m / z [M+H]+: found: 435.37.

[0183] Preparation Example 4

[0184] The present preparation example provides an intermediate 4, and a preparation method of the intermediate 4 includes the following steps:

[0185]

[0186] The synthesis of intermediate 4-1 was the same as that of intermediate 1-3, except that intermediate 1-2 was replaced by the same molar amount of intermediate 3-7, and raw material 2 was replaced by the same molar amount of raw material 4, to obtain intermediate 4-1 (0.18 g, yield 43%);

[0187] MS (APCI) m / z [M+H]+: found: 429.24.

[0188] The synthesis of intermediate 4-2 was the same as that of intermediate 1-4, except that intermediate 1-3 was replaced by the same molar amount of intermediate 4-1, to obtain intermediate 4-2 (0.30 g, yield 78%);

[0189] MS (APCI) m / z [M+H]+: found: 393.17.

[0190] The synthesis of intermediate 4 is similar to that of intermediate 1 except that intermediate 1-9 is replaced by an equivalent molar amount of intermediate 4-2 to give intermediate 4 (0.39 g, 81% yield);

[0191] MS (APCI) m / z [M+H]+: found: 485.27.

[0192] Preparation Example 5

[0193] The present preparation example provides an intermediate 5, and a preparation method of the intermediate 5 comprises the following steps:

[0194]

[0195] The synthesis of intermediate 5-1 is similar to that of intermediate 1-3 except that intermediate 1-2 is replaced by an equivalent molar amount of intermediate 3-7, and raw material 2 is replaced by an equivalent molar amount of raw material 5 to give intermediate 5-1 (0.18 g, 41% yield);

[0196] MS (APCI) m / z [M+H]+: found: 429.19.

[0197] The synthesis of intermediate 5-2 is similar to that of intermediate 1-4 except that intermediate 1-3 is replaced by an equivalent molar amount of intermediate 5-1 to give intermediate 5-2 (0.30 g, 77% yield);

[0198] MS (APCI) m / z [M+H]+: found: 393.27.

[0199] The synthesis of intermediate 5 is similar to that of intermediate 1 except that intermediate 1-9 is replaced by an equivalent molar amount of intermediate 5-2 to give intermediate 5 (0.41 g, 85% yield);

[0200] MS (APCI) m / z [M+H]+: found: 485.36.

[0201] Preparation Example 6

[0202] The present preparation example provides an intermediate 6, and a preparation method of the intermediate 6 comprises the following steps:

[0203]

[0204] The synthesis of intermediate 6-1 is similar to that of intermediate 1-3 except that intermediate 1-2 is replaced by an equivalent molar amount of intermediate 3-7, and raw material 2 is replaced by an equivalent molar amount of raw material 6 to give intermediate 6-1 (0.19 g, 44% yield);

[0205] MS (APCI) m / z [M+H]+: found: 429.19.

[0206] The synthesis of intermediate 6-2 was the same as that of intermediate 1-4, except that intermediate 1-3 was replaced with an equal molar amount of intermediate 6-1 to obtain intermediate 6-2 (0.28 g, yield 73%);

[0207] MS (APCI) m / z [M+H] + : found: 393.28.

[0208] The synthesis of intermediate 6 was the same as that of intermediate 1, except that intermediate 1-9 was replaced by an equal molar amount of intermediate 6-2 to obtain intermediate 6 (0.4 g, yield 84%).

[0209] MS (APCI) m / z [M+H] + : found: 485.31.

[0210] Preparation Example 7

[0211] This preparation example provides an intermediate 7, and the preparation method of intermediate 7 comprises the following steps:

[0212]

[0213] The synthesis of intermediate 7-1 was the same as that of intermediate 1-3, except that intermediate 1-2 was replaced by an equal molar amount of intermediate 2-2, and raw material 2 was replaced by an equal molar amount of raw material 3 to obtain intermediate 7-1 (0.16 g, yield 53%).

[0214] MS (APCI) m / z [M+H] + : found: 301.11.

[0215] The synthesis of intermediate 7-2 was the same as that of intermediate 1-4, except that intermediate 1-3 was replaced with an equal molar amount of intermediate 7-1 to obtain intermediate 7-2 (0.20 g, yield 77%);

[0216] MS (APCI) m / z [M+H] + : found: 264.18.

[0217] The synthesis of intermediate 7-3 was the same as that of 1-5, except that intermediate 1-4 was replaced with an equal molar amount of intermediate 7-2 to obtain intermediate 7-3 (0.18 g, yield 80%);

[0218] MS (APCI) m / z [M+H] + : found: 234.21.

[0219] Synthesis of intermediate 7-4: The synthesis was the same as that of intermediate 1-2, except that intermediate 1-1 was replaced with an equal molar amount of intermediate 7-3 to obtain intermediate 7-4 (0.18 g, yield 59%);

[0220] MS (APCI) m / z [M+H] + : found: 313.08.

[0221] The synthesis of intermediate 7-5 was the same as that of intermediate 1-1, except that the starting material 1 was replaced with an equal molar amount of intermediate 7-4 to obtain intermediate 7-5 (0.15 g, yield 45%);

[0222] MS (APCI) m / z [M+H] + : found: 331.13.

[0223] The synthesis of intermediate 7-6 was the same as that of intermediate 1-3, except that intermediate 1-2 was replaced by intermediate 7-5 to obtain intermediate 7-6 (0.119 g, yield 50%);

[0224] MS (APCI) m / z [M+H] + : found: 379.24.

[0225] The synthesis of intermediate 7-7 was the same as that of intermediate 1-4, except that intermediate 1-3 was replaced with an equal molar amount of intermediate 7-6 to obtain intermediate 7-7 (0.27 g, yield 80%);

[0226] MS (APCI) m / z [M+H] + : found: 343.18.

[0227] The synthesis of intermediate 7 was the same as that of intermediate 1, except that intermediate 1-9 was replaced by an equal molar amount of intermediate 7-7 to obtain intermediate 7 (0.36 g, yield 83%);

[0228] MS (APCI) m / z [M+H] + : found: 435.30.

[0229] Example 1

[0230] This embodiment provides an organic compound N-8, and the preparation method of the organic compound comprises the following steps:

[0231]

[0232] Synthesis of Compound N-8: Intermediate 1 (1 mmol), starting material 7 (1 mmol), sodium bicarbonate (2 mmol), tetrakistriphenylphosphine palladium (0.05 mmol), and dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (0.05 mmol) were added to a mixed solution of toluene (7 mL), ethanol (2 mL), and water (2 mL), and the atmosphere was replaced with nitrogen three times. Under nitrogen protection, the temperature was raised to 80°C and the reaction was carried out for 6 hours. After the reaction, the extract was extracted with ethyl acetate, and the resulting extract was dried over magnesium sulfate, filtered, and dried by rotary evaporation. The crude product was purified by chromatography (ethyl acetate:n-hexane (volume ratio 1:10)) to obtain Compound N-8 (0.55 g, 79% yield).

[0233] HRMS (ESI) m / z [M+H] + : found: 692.28.

[0234] Example 2-13

[0235] Example 2-13 provides 12 organic compounds. The preparation method is the same as that of compound N-5, except that the starting materials are different. The starting materials, yields, and mass spectrometry data of Examples 2-13 are shown below:

[0236]

[0237]

[0238]

[0239]

[0240] Application Examples 1-13 and Comparative Application Example 1

[0241] The following application examples 1-13 and comparative application example 1 respectively provide an OLED, such as Figure 1 As shown, the organic light-emitting device includes a substrate (indium tin oxide (ITO) coated glass substrate) 1, an anode 2, a hole injection layer (HIL) 3, a hole transport layer 4 (HTL), an emission layer (EML) 5, an electron transport layer (ETL) 6, an electron injection layer (EIL) 7 and a cathode 8 stacked in sequence;

[0242] The materials used are as follows:

[0243]

[0244] The preparation steps of OLED devices are as follows:

[0245] (1) Substrate cleaning: A glass substrate 1 coated with transparent ITO was ultrasonically treated in an aqueous detergent (the composition and concentration of the aqueous detergent: ethylene glycol solvent ≤ 10 wt%, triethanolamine ≤ 1 wt%), rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent (volume ratio 1:1), baked in a clean environment until the water was completely removed, and then cleaned with ultraviolet light and ozone.

[0246] (2) Evaporation of organic light-emitting functional layer:

[0247] The glass substrate 1 with the anode layer 2 is placed in a vacuum chamber and evacuated to 1×10 -6 to 2×10 -4 Pa, a mixture of PD and HT was vacuum-deposited on the above-mentioned anode layer film, wherein the mass ratio of PD to HT was 3:97, as the hole injection layer 3, and the deposition thickness was 10 nm;

[0248] A hole transport layer 4 (made of HT) is evaporated on the hole injection layer 3 with a thickness of 80 nm.

[0249] The light-emitting layer 5 is deposited on the hole transport layer 4. The specific preparation method is: vacuum evaporation of the light-emitting host material (as shown in the table below) and the guest material GD by co-evaporation, with a total film thickness of 30 nm;

[0250] An electron transport layer 6 is deposited on the light-emitting layer 5 by vacuum evaporation of ET and LiQ in a co-evaporation manner, with a total film thickness of 30 nm.

[0251] An electron injection layer 7 (made of LiQ) is vacuum-deposited on the electron transport layer 6, with a total film thickness of 1 nm.

[0252] Cathode 8Al was vapor-deposited on the electron injection layer 7, and the total vapor-deposited film thickness was 90 nm.

[0253] The parameters of each layer in the device, its material, thickness, etc. are shown in the following table:

[0254]

[0255] Test Case

[0256] Device performance test

[0257] Test objects: Organic electroluminescent devices provided in Application Examples 1-13 and Comparative Application Example 1

[0258] Instruments: The device's current, voltage, brightness, luminous spectrum and other characteristics are tested synchronously using a PR 650 spectrum scanning luminance meter and a Keithley K 2400 digital source meter system;

[0259] Photoelectric property test condition: current density is 10mA / cm 2 ;

[0260] Lifetime test: current density is 10mA / cm 2 , record time (in hours) when device brightness drops to 95% of original brightness;

[0261] Test results are shown in Table 1 as follows:

[0262] Table 1

[0263]

[0264] From the data in Table 1, it can be seen that the organic compound provided by the application used in the light-emitting layer host material of the organic light-emitting device can reduce the device driving voltage, improve the device light-emitting efficiency and lifetime.

[0265] The applicant declares that the process method of the application is illustrated by the above examples, but the application is not limited to the above process steps, that is, it does not mean that the application must rely on the above process steps to be implemented. It should be understood by those skilled in the art that any improvement on the application, equivalent replacement of the materials selected by the application, addition of auxiliary ingredients, selection of specific methods, etc. fall within the protection scope and disclosure scope of the application.

Claims

1. An organic compound, characterized in that The organic compound has the structure shown in the following formula I: Formula I; wherein X1 is selected from a single bond, and X2 is selected from an oxygen atom; (1) R2 is selected from substituted pyrimidinyl, substituted triazine, R1, R3-R 12 is selected from hydrogen, or, (2) R2 is selected from substituted pyrimidinyl, substituted triazine, R1, R3-R6, R9-R 12 Selected from hydrogen, R7 and R8 connected to form a benzene ring; The substituents in the substituted pyrimidinyl group and the substituted triazinyl group are each independently selected from any one or a combination of C6-C60 aryl group or C3-C60 heteroaryl group.

2. An organic compound, characterized in that The organic compound has the structure shown in the following formula I: Formula I; wherein X1 is selected from an oxygen atom, and X2 is selected from a single bond; (1) Any one of R2 and R6 is selected from substituted pyrimidinyl and substituted triazine, R1-R 12 The remaining groups in are selected from hydrogen, or (2) any one of R2 and R6 is selected from substituted pyrimidinyl and substituted triazine, and two adjacent groups in R1, R2, R3 and R4 are connected to form a benzene ring, R1-R 12 The remaining groups in are selected from hydrogen; The substituents in the substituted pyrimidinyl group and the substituted triazinyl group are each independently selected from any one or a combination of C6-C60 aryl group or C3-C60 heteroaryl group.

3. The organic compound according to claim 1 or 2, characterized in that R2 is selected from substituted pyrimidinyl, substituted triazinyl, R1, R3-R 12 selected from hydrogen; The substituents in the substituted pyrimidinyl group and the substituted triazinyl group are each independently selected from any one or a combination of C6-C60 aryl group or C3-C60 heteroaryl group.

4. The organic compound according to claim 2, characterized in that R6 is selected from substituted pyrimidinyl, substituted triazine, R1-R5, R7-R 12 selected from hydrogen; The substituents in the substituted pyrimidinyl group and the substituted triazinyl group are each independently selected from any one or a combination of C6-C60 aryl group or C3-C60 heteroaryl group.

5. The organic compound according to claim 2, characterized in that The R3 and R4 are connected to form a benzene ring.

6. The organic compound according to claim 2, characterized in that The R2 and R3 are connected to form a benzene ring.

7. The organic compound according to claim 2, characterized in that The R1 and R2 are connected to form a benzene ring.

8. The organic compound according to claim 1 or 2, characterized in that The substituted pyrimidinyl and substituted triazine groups are each independently selected from any one of the following structures: ； in, Indicates the attachment site of a group.

9. An organic compound, characterized in that The organic compound is selected from any one of the following compounds: 。 10. An organic electroluminescent material, characterized in that: The organic electroluminescent material comprises the organic compound according to any one of claims 1 to 9.

11. An organic electroluminescent device, characterized in that: The organic electroluminescent device includes an anode, a cathode, and an organic thin film layer located between the anode and the cathode, wherein the organic thin film layer includes any one or a combination of at least two of a hole injection layer, a hole transport layer, a luminescence auxiliary layer, a light-emitting layer, a hole blocking layer, an electron buffer layer, an electron transport layer, or an electron injection layer, and the light-emitting layer includes the organic compound according to any one of claims 1 to 9.

12. The organic electroluminescent device according to claim 11, characterized in that: The light-emitting layer includes a host material and a guest material, and the host material includes the organic compound according to any one of claims 1 to 9.

13. An electronic device, characterized in that: The electronic device comprises the organic electroluminescent device according to claim 11 or 12.

14. The electronic device according to claim 13, wherein: The electronic device is an optical fiber.

15. The electronic device according to claim 13, wherein: The electronic device is a lighting device.

16. The electronic device according to claim 13, wherein: The electronic device is an electrophotographic photoreceptor.

17. The electronic device according to claim 13, wherein: The electronic device is a photoelectric converter.

18. The electronic device according to claim 13, wherein: The electronic device is an organic solar cell.

19. The electronic device according to claim 13, wherein: The electronic device is a switching element.

20. The electronic device according to claim 13, wherein The electronic device is an organic light-emitting field-effect transistor.

21. The electronic device according to claim 13, wherein: The electronic device is an image sensor.

22. The electronic device according to claim 13, wherein: The electronic device is a dye laser.

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