Organic compound and application thereof

Abstract

The invention provides a polycyclic aromatic compound and application thereof. The polycyclic aromatic compound has a structure as shown in a formula (1). The polycyclic aromatic compound provided by the invention has good stability and steric configuration, has excellent carrier transport efficiency, and can effectively prolong the service life of an organic electroluminescent device and improve the luminous efficiency when being used as a material of a luminous layer for the organic electroluminescent device.

Description

Technical Field

[0001] This invention belongs to the field of organic light-emitting materials technology, specifically relating to a polycyclic aromatic compound, as well as the application of this compound in organic electroluminescent devices and organic electroluminescent devices using this type of compound. Background Technology

[0002] The inherent flexibility of organic materials makes them ideal for fabrication on flexible substrates, enabling the design and production of aesthetically pleasing and stylish optoelectronic products that offer unparalleled advantages over inorganic materials. Examples of such organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors (FETs), organic photovoltaic cells, and organic sensors. OLEDs, in particular, have experienced rapid development and have already achieved commercial success in the information display field. OLEDs can provide highly saturated red, green, and blue colors, and full-color displays made with them require no additional backlight, offering advantages such as vibrant colors, thinness, and flexibility.

[0003] The core of an OLED device is a thin-film structure containing various organic functional materials. Common functionalized organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, as well as light-emitting host materials and light-emitting guest materials (dyes). When an electric current is applied, electrons and holes are injected and transported to the light-emitting region, where they recombine, thereby generating excitons and emitting light.

[0004] People have developed a variety of organic materials that can improve carrier mobility, regulate carrier balance, improve electroluminescence efficiency, and delay device decay.

[0005] In 2016, Professor Takuji Hatakeyama of Japan proposed a design strategy for TADF (Thermally Activated Delayed Fluorescence) materials based on BN resonance (Adv. Mater. 2016, 28, 2777-2781). These materials, composed of boron atoms, nitrogen atoms, and multiple benzene rings, exhibit a rigid polycyclic aromatic hydrocarbon structure and possess high fluorescence quantum yields. In particular, compared to traditional blue fluorescent dyes, they exhibit narrower spectra and higher color purity, demonstrating significant advantages. However, due to their particularly planar and rigid structure, they are prone to molecular stacking and exciton annihilation, resulting in a severe efficiency roll-off. Therefore, there is still considerable room for improvement in the luminescence performance of this type of organic electroluminescent material.

[0006] As OLED products gradually enter the market, people have increasingly higher requirements for their performance. Current OLED materials and device structures cannot fully address the issues of efficiency, lifespan, and cost in OLED products. Therefore, there is an urgent need in this field to develop more diverse and higher-performance organic materials for application in organic electroluminescent devices, enabling these devices to achieve better luminescence and longer lifespans. Summary of the Invention

[0007] To address the shortcomings of existing technologies, the present invention aims to provide an aromatic compound and its applications, specifically a polycyclic aromatic compound and its applications.

[0008] The polycyclic aromatic compounds provided by this invention introduce nitrogen atoms into a parent nucleus (e.g., a BN parent nucleus) and simultaneously introduce specific low-triple-state segment structural groups into the periphery. This structure can, on the one hand, lower the HOMO energy level of the material, reduce hole trapping, and make the ratio of holes to electrons in the device more balanced, thus improving both efficiency and lifetime. On the other hand, the low-triple-state segments can lower the triplet energy level of the molecule, which is beneficial for further improving the device lifetime. Therefore, through ingenious molecular / device design, the polycyclic aromatic compounds provided by this invention are very suitable for application in OLEDs and for improving device performance.

[0009] To achieve this objective, the present invention adopts the following technical solution:

[0010] In a first aspect, the present invention provides a polycyclic aromatic compound having a structure as shown in formula (1):

[0011]

[0012] In formula (1), ring A and ring B are independently selected from one of unsubstituted or R0-substituted C6-C30 aromatic rings and unsubstituted or R0-substituted C3-C30 heteroaromatic rings.

[0013] R0 is independently selected from deuterium and R A The RO group comprises one or a combination of two of the following: halogen, cyano, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryl, and C6-C30 aryl; adjacent RO groups may be connected to form a ring or not; each RO group is independently not connected to an adjacent ring structure or is connected to form a ring by a chemical bond;

[0014] X1, X2, X3, X4, X5, X6, X7, X8, X9, X 10Each is independently selected from N or CR1, and at least one of them is selected from N; two adjacent R1s are connected in a loop or not connected;

[0015] R2 represents a single-substituted group up to the maximum allowed number of substituents;

[0016] R1 and R2 are each independently selected from hydrogen and R A Halogen, cyano, unsubstituted or R 01 Substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R 01 Substituted C3-C20 cycloalkyl, unsubstituted or R 01 Substituted C2-C20 alkenyl, unsubstituted or R 01 Substituted C3-C30 heteroaryl, unsubstituted or R 01 One of the substituted C6-C30 aryl groups;

[0017] R 01 Each is independently selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryl, and C6-C30 aryl; two adjacent R 01 The R can be connected in a loop or not; 01 Each ring is independent and not connected to the adjacent ring structure or is connected to form a ring by chemical bonds;

[0018] At least one of R0, R1, and R2 is R. A R A It is one of substituted or unsubstituted C6-C60 aryl groups with T1 < 2.40 eV, or substituted or unsubstituted C3-C60 heteroaryl groups with T1 < 2.40 eV, wherein each of the substituted substituents is independently selected from one or a combination of two of deuterium, halogen, cyano, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C1-C20 alkoxy, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl;

[0019] Y1 and Y2 are each independently selected from single bonds, O or S, n1 and n2 are each independently 0 or 1, and n1+n2 is 1 or 2.

[0020] Preferably, in formula (1), at least one of R0, R1, and R2 is selected from R A The R AIt is one of the following: substituted or unsubstituted C13-C40 (e.g., C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, or C38, etc.) aryl groups with T1 < 2.40 eV; or substituted or unsubstituted C12-C40 (e.g., C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, or C38, etc.) heteroaryl groups with T1 < 2.40 eV;

[0021] Preferably, the R A Selected from one of the following substituted or unsubstituted groups, Linkage sites of representative groups:

[0022]

[0023]

[0024] The substituents are independently selected from one or a combination of two of the following: deuterium, halogen, cyano, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C1-C20 alkoxy, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, each of the substituents is independently selected from deuterium, halogen, cyano, amino, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) straight-chain or branched alkyl, C6-C30... One or a combination of two of the following: 3-C10 (e.g., C4, C5, C6, C7, C8 or C9); C2-C10 (e.g., C3, C4, C5, C6, C7, C8 or C9); C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18); and C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18).

[0025] More preferably, the R A Selected from one of the following substituted or unsubstituted groups, Linkage sites of representative groups:

[0026]

[0027] The substituents are each independently selected from one or a combination of two of the following: C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) straight-chain or branched alkyl groups; C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) aryl groups; and C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroaryl groups; preferably, the substituents are each independently selected from C1-C3 straight-chain alkyl groups and isopropyl groups. tert-butyl Isobutyl tert-amyl One or a combination of two of phenyl or naphthyl groups.

[0028] More preferably, the R A Selected from one of the following groups, Linkage sites of representative groups:

[0029]

[0030] More preferably, the compound of formula (1) of the present invention is selected from the structures shown in formula (1-1), formula (1-2), formula (1-3), formula (1-4) or formula (1-5):

[0031]

[0032] Among them, X2-X 10 The definition of R2 is the same as that in equation (1);

[0033] Y1 and Y2 are each independently selected from O or S;

[0034] Z2, Z3, Z4, Z5, Z6, Z7, and Z8 are each independently selected from N or CR3;

[0035] R3 is independently selected from hydrogen, deuterium, and R A One or a combination of two of the following: halogen, cyano, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryl, and C6-C30 aryl; adjacent R3s may or may not be linked to form a ring.

[0036] Y3 is selected from O or S.

[0037] Furthermore, X2-X 10At least one of them is selected from N, and at most four (e.g., 1, 2, 3, or 4) are selected from N, and the rest are selected from CR1 (multiple (e.g., 2, 3, 4, 5, 6, 7, 8, or 9) R1s are the same or different from each other, and adjacent R1s are connected by chemical bonds to form a ring or are not connected); more preferably, X3, X5, X8, X 10 At least one (e.g., 1, 2, 3, or 4) is selected from N, and the remainder is selected from CR1; more preferably, X3, X5, X8, X 10 At most two (e.g., one or two) are selected from N, and the rest are selected from CR1; more preferably, X3 and / or X5 are selected from N, and X8, X 10 Selected from N or CR1, the rest selected from CR1 (e.g., X3 or X5 selected from N, the rest selected from CR1, or X3 and X8 selected from N, the rest selected from CR1, or X5 and X...). 10 Selected from N, the rest from CR1); more preferably, X3 and / or X5 are selected from N, X2 and X4 are selected from CH, X8 and X 10 Selected from N or CR1, the rest are selected from CR1;

[0038] Each of R1 is independently selected from hydrogen, R A Halogen, cyano, unsubstituted or R 01 Substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) straight-chain or branched alkyl groups, unsubstituted or R 01 Substituted C3-C10 (e.g., C4, C5, C6, C7, C8, or C9, etc.) cycloalkyl, unsubstituted, or R 01 Substituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28, etc.) heteroaryl, unsubstituted, or R 01 One of the substituted C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28, etc.) aryl groups; R 01Each is independently selected from deuterium, halogen, cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) straight-chain or branched alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, or C9, etc.) cycloalkyl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) alkoxy, C1-C10 (e.g., C 2. C3, C4, C5, C6, C7, C8, or C9, etc.) alkylsilyl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) alkylamino, C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28, etc.) arylamino, C3-C 30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28, etc.) heteroarylamino, C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28, etc.) aryloxy, C3 One of the following: -C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26 or C28, etc.) heteroaryl, and C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26 or C28, etc.) aryl.

[0039] More preferably, each of R1 is independently selected from hydrogen, R A Halogen, cyano, unsubstituted or R 01 Substituted C1-C6 (e.g., C2, C3, C4, or C5) straight-chain or branched alkyl groups, unsubstituted or R 01 Substituted C3-C6 (e.g., C4 or C5) cycloalkyl, unsubstituted or R 01 Substituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroaryl, unsubstituted, or R 01 One of the substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) aryl groups; R 01Each is independently selected from one of the following: deuterium, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8 or C9, etc.) straight-chain or branched alkyl, C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, and C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl.

[0040] More preferably, each of R1 is independently selected from hydrogen, R A halogen, cyano, or any of the following groups, Linkage sites of representative groups:

[0041]

[0042] In this invention, two adjacent R1s are connected to form a ring by chemical bonds (e.g., forming a ring). (etc.) or not connected.

[0043] Further, in formulas (1-1), (1-2), (1-3), (1-4), and (1-5), at most one (e.g., 0 or 1) of Z2 to Z8 is selected from N, and the rest are selected from CR3 (multiple (e.g., 2, 3, 4, 5, 6, or 7) R3s are the same or different from each other; adjacent R3s are connected by chemical bonds to form a ring or are not connected); preferably, Z2 to Z8 are each independently selected from CR3; more preferably, Z2, Z4, and Z5 are selected from CH, and the rest are independently selected from CR3;

[0044] Each of the R3s is independently selected from hydrogen, deuterium, and R. A Halogen, cyano, C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) straight-chain or branched alkyl, C3-C20 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) cycloalkyl, C2-C20 (e.g., C3 ... 10. One or a combination of two of the following: alkenyl (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28); heteroaryl (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28); and aryl (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28).

[0045] More preferably, R3 is independently selected from hydrogen, deuterium, and R A One or a combination of two of the following: C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8 or C9, etc.) straight-chain or branched alkyl groups; C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl groups; and C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl groups.

[0046] More preferably, R3 is independently selected from hydrogen, R A halogen, cyano, or any of the following groups, Linkage sites of representative groups:

[0047]

[0048] Furthermore, in equations (1), (1-1), (1-2), (1-3), (1-4), and (1-5), R2 is independently selected from hydrogen, R A Halogen, cyano, unsubstituted or R 01 Substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) straight-chain or branched alkyl groups, unsubstituted or R 01 Substituted C3-C10 (e.g., C4, C5, C6, C7, C8, or C9, etc.) cycloalkyl, unsubstituted, or R 01 Substituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28, etc.) heteroaryl, unsubstituted, or R 01 One of the substituted C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28, etc.) aryl groups; R 01Each is independently selected from deuterium, halogen, cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) straight-chain or branched alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, or C9, etc.) cycloalkyl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) alkoxy, C1-C10 (e.g., C 2. C3, C4, C5, C6, C7, C8, or C9, etc.) alkylsilyl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9, etc.) alkylamino, C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28, etc.) arylamino, C3-C 30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28, etc.) heteroarylamino, C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26, or C28, etc.) aryloxy, C3 One of the following: -C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26 or C28, etc.) heteroaryl, and C6-C30 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, C26 or C28, etc.) aryl.

[0049] More preferably, each of the R2 molecules is independently selected from hydrogen, R... A Halogen, cyano, unsubstituted or R 01 Substituted C1-C6 (e.g., C2, C3, C4, or C5) straight-chain or branched alkyl groups, unsubstituted or R 01 Substituted C3-C6 (e.g., C4 or C5) cycloalkyl, unsubstituted or R 01 Substituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroaryl, unsubstituted, or R 01 One of the substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) aryl groups; R 01Each is independently selected from one of the following: deuterium, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8 or C9, etc.) straight-chain or branched alkyl, C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, and C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) aryl.

[0050] More preferably, each of R2 is independently selected from hydrogen, R A halogen, cyano, or any of the following groups, Linkage sites of representative groups:

[0051]

[0052] In this invention, the "substituted or unsubstituted" group can replace one substituent or multiple substituents. When there are multiple substituents (at least two), they can be the same or different substituents. The same expression used above has the same meaning.

[0053] In this invention, "each of the substituents is independently not connected to the adjacent ring structure" means that the substituent is only connected to the C atom through a single bond; "each of the substituents is independently connected to the adjacent ring structure through chemical bonds to form a ring" means that the substituent, in addition to being connected to the C atom through chemical bonds, is also connected to the adjacent ring through chemical bonds, thereby forming a fused ring structure. The same descriptions used above have the same meaning and will not be repeated here.

[0054] In this invention, the expression of Ca to Cb represents that the group has a to b carbon atoms. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms of the substituent.

[0055] In this invention, the "-" line on the group refers to the way the ring structure is drawn, indicating that the bonding site is located at any position on the ring structure where bonding can occur.

[0056] In this invention, "each independently" means that when there are multiple subjects, they can be the same or different from each other.

[0057] In this invention, unless otherwise specified, the description of chemical elements generally includes the concept of their isotopes. For example, the description of "hydrogen (H)" includes its isotopes. 1 H (protium or H), 2 The concept of H (deuterium or D); carbon (C) includes... 12 C 13 C, etc., will not be elaborated further.

[0058] The heteroatoms in the heteroaryl group of this invention generally refer to atoms or groups of atoms selected from N, O, S, P, Si and Se, preferably from N, O and S.

[0059] Examples of halogens in this invention include fluorine, chlorine, bromine, and iodine.

[0060] In this invention, C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0061] C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0062] C1-C30 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26 or C28, etc.

[0063] C1-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.

[0064] C3-C20 can all be C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.

[0065] C2-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.

[0066] In this invention, the C6-C60 aryl group, preferably C6-C24 aryl group, includes monocyclic aryl and fused-ring aryl groups; the monocyclic aryl group means that the group contains at least one phenyl group, and when it contains at least two phenyl groups, the phenyl groups are linked by single bonds, including but not limited to: phenyl, biphenyl, terphenyl, tetraphenyl, etc. The term "fused-ring aryl" refers to a group containing at least two aromatic rings, wherein the aromatic rings share two adjacent carbon atoms fused together. Exemplary examples include, but are not limited to: naphthyl (1-naphthyl, 2-naphthyl), anthraceneyl (1-anthrayl, 2-anthrayl, 9-anthrayl), phenanthryl, indene, fluorenyl and their 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, phenylmethylfluorenyl, spirodifluorenyl, benzo[a]fluorenyl, etc.), fluoranyl, triphenylene, pyrene (1-pyrene, 2-pyrene, 4-pyrene), peryl, Aryl groups include aryl groups, pheno-tetraphenyl (1-pheno-tetraphenyl, 2-pheno-tetraphenyl, 9-pheno-tetraphenyl), etc. It should be noted that monocyclic aryl groups and fused-ring aryl groups linked by single bonds also fall under the aryl group category, such as phenylnaphthyl, naphthylphenyl, and binaphthyl.

[0067] In this invention, the C3-C60 heteroaryl group, preferably a C3-C20 heteroaryl group, includes monocyclic heteroaryl groups or fused-ring heteroaryl groups. A 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 other groups are connected by a single bond, exemplarily including but not limited to: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiophene, pyrroleyl, bipyridyl, phenylpyridinyl, pyridylphenyl, pyrimidinylphenyl, etc. The term "fused-ring heteroaryl" refers to a molecule containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring), and the two share two adjacent atoms fused together in a group. Examples include, but are not limited to: quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, isobenzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, carbazoleyl and its derivatives (N-phenylcarbazoleyl, N-naphthylcarbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, indolocarbazoleyl, azacarbazoleyl, etc.), acridineyl, phenothiazinyl, phenotoxazinyl, hydrogenated acridineyl, etc. It should be noted that heteroaryl groups connected by single bonds, as well as aryl groups connected by single bonds, also fall under the category of heteroaryl groups, such as phenyldibenzofuranyl, phenyldibenzothiophenyl, dibenzothiophenylphenyl, dibenzofuranylphenyl, etc.

[0068] The C1-C30 straight-chain or branched alkyl group, C1-C20 straight-chain or branched alkyl group, preferably C1-C10 straight-chain or branched alkyl group, includes, but is not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, 2-methylbutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, neohexyl, 2-ethylhexyl, n-octyl, n-heptyl, n-nonyl, n-decyl, etc.

[0069] Specific examples of the C1-C30 alkoxy groups can be exemplified by the monovalent groups obtained by connecting the above-mentioned straight-chain or branched alkyl groups with O.

[0070] The C3-C30 cycloalkyl group mentioned in this invention is preferably a C3-C20 cycloalkyl group, more preferably a C3-C10 cycloalkyl group, such as cyclopropyl, cyclobutyl, cyclopentyl, tert-amyl, cyclohexyl, adamantyl, etc.

[0071] The C2-C20 alkenyl group mentioned in this invention is preferably a C2-C10 alkenyl group, which contains at least one C=C, and includes, but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0072] Specific examples of C2-C20 heterocyclic alkyl groups mentioned in this invention can be exemplified by groups formed by replacing at least one C atom in the aforementioned cycloalkyl group with a heteroatom (e.g., N, O, S, etc.), including but not limited to: epoxy group, oxetane group, tetrahydrofuranyl group, tetrahydrothiophenyl group, tetrahydropyrroleyl group, tetrahydropyranyl group, piperidinyl group, piperazineyl group, dioxaneyl group, morpholinyl group, etc.

[0073] Furthermore, preferred structures of the compounds described in this invention can be exemplified by the following specific compounds, but are not limited to these compounds:

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082] The specific reasons for the excellent performance of the above-mentioned compounds as light-emitting layer materials are not yet clear, but it is speculated that the reasons may be as follows:

[0083] (1) X1-X in the core structure of the compound of the present invention 10 At least one of them is N, which can reduce the HOMO energy level of the compound, reduce hole trapping, and thus achieve a more balanced ratio of holes and electrons in the device;

[0084] (2) The n1+n2 in the core structure of the compound of the present invention is 1 or 2, which can adjust the blue shift of light color caused by the introduction of N atoms in the molecular structure, and ensure that the emission peak of the compound of the present invention is located near sky blue light (~460nm);

[0085] (3) The compound core of this invention is designed with R-connection A The low triplet group with this specific structure has been verified through extensive experiments to effectively reduce the triplet energy level of the compound, thereby ensuring a significant improvement in the lifetime of organic electroluminescent devices using the compound of this invention.

[0086] As another aspect of the invention, the application of the compound described above in an organic electroluminescent device is also provided, wherein the compound is applied to an organic electronic device. 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. More specifically, the application as a light-emitting layer material in an organic electroluminescent device is preferred, and the application in a blue organic electroluminescent device is even more preferred. More preferably, the compound of the present invention is used as a blue dye (blue dopant material) in the organic electroluminescent device.

[0087] As another aspect of the present invention, an organic electroluminescent device is also provided, comprising a first electrode, a second electrode and an organic layer inserted between the first electrode and the second electrode, wherein the organic layer contains a compound represented by formula (1) as described above.

[0088] Specifically, one embodiment of the present invention provides an organic electroluminescent device, including a substrate, and a first electrode, a plurality of light-emitting functional layers, and a second electrode sequentially formed on the substrate; the light-emitting functional layers include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is located between the hole transport layer and the electron transport layer; wherein the light-emitting layer includes a host material and a dopant material, and the dopant material includes at least one compound represented by formula (1) as described above.

[0089] The present invention also discloses an electronic device having a display screen or display panel, wherein the display screen or display panel employs an organic electroluminescent device as described above. Detailed implementation method:

[0090] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be considered as specific limitations thereof. The polycyclic aromatic compounds provided by the present invention can be obtained by known methods, such as synthesis using known organic synthesis methods. Exemplary synthetic routes are given below, but those skilled in the art can also obtain them using other known methods.

[0091] In one specific embodiment, the polycyclic aromatic compound can be prepared via the following synthetic route:

[0092]

[0093] Among them, ring A, ring B, R2, Y1, Y2, X1-X 10 n1 and n2 have the same defined range as in equation (1); Hal 1 Hal 2 Hal 3 Each is an independent halogen, and Cl or Br is preferred.

[0094] It should be noted that obtaining the polycyclic aromatic compounds is not limited to the synthetic methods and raw materials used in this invention. Those skilled in the art can also select other methods or routes to obtain the polycyclic aromatic compounds proposed in this invention. Compounds for which synthetic methods are not mentioned in this invention are all commercially available raw material products, or are prepared in-house using these raw material products according to known methods.

[0095] The solvents and reagents used in this invention can all be purchased from the chemical product market.

[0096] The specific preparation methods of the polycyclic aromatic compounds of the present invention will be described in detail below using several synthetic examples, but the preparation methods of the present invention are not limited to these synthetic examples.

[0097] The structural analysis of intermediates and compounds in this invention was performed using an ABSCIEX mass spectrometer (4000QTRAP).

[0098] Synthetic Example 1: Synthesis of Polycyclic Aromatic Compound M1

[0099]

[0100] Synthesis of intermediate M1-1:

[0101] At room temperature, M1-0 (20.0 g), 2-chloro-4-tert-butylaniline (23.3 g), Pd(dppf)Cl2 (4.6 g), sodium tert-butoxide (24.3 g), and toluene (500 mL) were added to a 1 L single-necked flask. The mixture was purged with nitrogen three times and heated to 100 °C overnight. The reaction mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 5:2, v:v) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 28.7 g of a white solid, with a yield of 87.0%.

[0102] Mass of the molecular ion [M+H] determined by mass spectrometry analysis + 261.24 (Theoretical value: 260.11).

[0103] Synthesis of intermediate M1-2:

[0104] At room temperature, M1-1 (20.0 g), Pd(OAc)2 (0.9 g), tri-tert-butylphosphide tetrafluoroborate (2.2 g), sodium tert-butoxide (14.7 g), and toluene (500 mL) were added to a 1 L single-necked flask. The mixture was purged with nitrogen three times and heated to 100 °C overnight. The reaction mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 5:2, v:v) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 13.6 g of a white solid, yield 79.0%.

[0105] Mass of the molecular ion [M+H] determined by mass spectrometry analysis + 225.16 (Theoretical value: 224.13).

[0106] Synthesis of intermediate M1-3:

[0107] At room temperature, M1-2 (10.0 g), 1,3-dibromo-2-chloro-5-tert-butylbenzene (14.6 g), Pd2(dba)3 (2.0 g), tri-tert-butylphosphide tetrafluoroborate (1.3 g), sodium tert-butoxide (8.6 g), and toluene (500 mL) were added to a 1 L single-necked flask. The mixture was purged with nitrogen three times and heated to 100 °C overnight. The reaction mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 10:1, v:v) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 17.4 g of a white solid, with a yield of 83.3%.

[0108] Mass of the molecular ion [M+H] determined by mass spectrometry analysis + : 469.15 (Theoretical value: 468.10).

[0109] Synthesis of intermediate M1-4:

[0110] At room temperature, M1-3 (15.0 g), A0 (8.3 g), Pd2(dba)3 (1.5 g), tri-tert-butylphosphide tetrafluoroborate (0.9 g), sodium tert-butoxide (5.8 g), and toluene (500 mL) were added to a 1 L single-necked flask. The mixture was purged with nitrogen three times and heated to 100 °C overnight. The reaction mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 10:1, v:v) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 16.7 g of a white solid, with a yield of 80.7%.

[0111] Mass of the molecular ion [M+H] determined by mass spectrometry analysis + : 648.32 (Theoretical value: 647.28).

[0112] Synthesis of compound M1-5:

[0113] At room temperature, M1-4 (15.0 g) was dissolved in 100 mL of xylene. After purging with nitrogen three times, the reaction system was cooled to -20 °C, and then tert-butyllithium (28.9 mL, 1.6 M) was added. The mixture was stirred at this low temperature for 30 minutes. The temperature was then gradually increased to 60 °C and maintained for 2 hours. Finally, the temperature of the reaction system was lowered back to -20 °C, and boron tribromide (8.8 mL) was added under nitrogen protection. After stirring for 30 minutes, diisopropylethylamine (30.0 mL) was added. The reaction system was then heated to 120 °C and reacted for 3 hours. After cooling to room temperature, the organic phase was evaporated to dryness under reduced pressure. The mixture was extracted with dichloromethane (200 mL), dried over anhydrous sodium sulfate, concentrated with silica gel, and subjected to column chromatography (PE:DCM = 10:1, v:v) to obtain a crude product. Recrystallization yielded 2.1 g of a yellow solid, with a yield of 14.6%.

[0114] Mass of the molecular ion [M+H] determined by mass spectrometry analysis + 622.45 (Theoretical value: 621.31).

[0115] Synthesis of compound M1:

[0116] At room temperature, M1-5 (2.0 g), Al (0.7 g), Pd132 (0.1 g), sodium tert-butoxide (0.6 g), and toluene (20 mL) were added to a 100 mL single-necked flask. The mixture was purged with nitrogen three times and heated to 100 °C overnight. The reaction mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 10:1, v:v) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 2.1 g of a yellow solid, with a yield of 81.4%.

[0117] Mass of the molecular ion [M+H] determined by mass spectrometry analysis + : 803.46 (Theoretical value: 802.42).

[0118] Synthesis Example 2: Synthesis of polycyclic aromatic compound M15

[0119]

[0120] The synthesis of intermediates M1-1, M1-2 and M1-3 is as described above;

[0121] Synthesis of intermediate M15-4:

[0122] The synthesis method is the same as M1-4, except that A2 is used instead of A1.

[0123] Mass of the molecular ion [M+H] determined by mass spectrometry analysis + 648.55 (Theoretical value: 647.28).

[0124] Synthesis of intermediate M15-5:

[0125] At room temperature, M15-4 (15.0 g), A3 (4.4 g), Pd132 (0.8 g), sodium tert-butoxide (4.4 g), and toluene (500 mL) were added to a 1 L single-necked flask. The mixture was purged with nitrogen three times and heated to 100 °C overnight. The reaction mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 5:3, v:v) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 14.7 g of a white solid, yield 79.0%.

[0126] Mass of the molecular ion [M+H] determined by mass spectrometry analysis + : 803.36 (Theoretical value: 802.38).

[0127] Synthesis of compound M15:

[0128] The synthesis method is the same as M1-5, except that M1-4 is replaced by M15-5.

[0129] Mass of the molecular ion [M+H] determined by mass spectrometry analysis + 777.45 (Theoretical value: 776.41).

[0130] Synthesis Example 3: Synthesis of the polycyclic aromatic compound M62

[0131]

[0132] The synthesis of intermediates M1-1 and M1-2 is as described above;

[0133] Synthesis of intermediate M62-3:

[0134] The synthesis method is the same as M1-3, except that 1,3-dibromo-2,5-dichlorobenzene is used instead of 1,3-dibromo-2-chloro-5-tert-butylbenzene. The molecular ion mass [M+H] was determined by mass spectrometry. + : 447.12 (Theoretical value: 446.00).

[0135] Synthesis of intermediate M62-4:

[0136] The synthesis method is the same as M1-4, except that M1-3 is replaced by M62-3 and A1 is replaced by A4.

[0137] Mass of the molecular ion [M+H] determined by mass spectrometry analysis + : 648.23 (Theoretical value: 647.28).

[0138] Synthesis of intermediate M62-5:

[0139] The synthesis method is the same as M1-5, except that M1-4 is replaced by M62-4.

[0140] Mass of the molecular ion [M+H] determined by mass spectrometry analysis + : 622.36 (Theoretical value: 621.31).

[0141] Synthesis of compound M62:

[0142] At room temperature, M62-5 (2.0 g), 1-pyreneboronic acid (0.8 g), Pd(OAc)2 (0.1 g), tri-tert-butylphosphide tetrafluoroborate (0.2 g), sodium tert-butoxide (0.6 g), and toluene (500 mL) were added to a 1 L single-necked flask. The mixture was purged with nitrogen three times and heated to 100 °C overnight. The reaction mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 5:2, v:v) to obtain a crude product. Methanol was then added and the mixture was slurried to give 1.9 g of a yellow solid, with a yield of 75.1%.

[0143] Mass of the molecular ion [M+H] determined by mass spectrometry analysis + 788.56 (Theoretical value: 787.41).

[0144] Synthesis Example 4: Synthesis of the polycyclic aromatic compound M81

[0145]

[0146] Synthesis of intermediate M81-1:

[0147] At room temperature, M81-0 (20.0 g), 1-peryleneboronic acid (28.7 g), Pd(PPh3)4 (5.6 g), potassium carbonate (26.8 g), and 1,4-dioxane / water (550 mL, v / v = 10 / 1) were added to a 1 L single-necked flask. The mixture was purged with nitrogen three times and heated to 100 °C overnight. The reaction mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 5:3, v:v) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 30.7 g of a white solid, yielding 83.9%.

[0148] Mass of the molecular ion [M+H] determined by mass spectrometry analysis + 378.15 (Theoretical value: 377.10).

[0149] Synthesis of intermediate M81-2:

[0150] The synthesis method is the same as M1-1, except that 2-chloro-4-tert-butylaniline is replaced with M81-1.

[0151] Mass of the molecular ion [M+H] determined by mass spectrometry analysis + : 455.16 (Theoretical value: 454.12).

[0152] Synthesis of intermediate M81-3:

[0153] The synthesis method is the same as M1-2, except that M1-1 is replaced by M81-2.

[0154] Mass of the molecular ion [M+H] determined by mass spectrometry analysis + : 419.25 (Theoretical value: 418.15).

[0155] Synthesis of intermediate M81-4:

[0156] The synthesis method is the same as M1-3, except that M81-3 is used instead of M1-2.

[0157] Mass of the molecular ion [M+H] determined by mass spectrometry analysis + : 663.13 (Theoretical value: 662.11).

[0158] Synthesis of intermediate M81-5:

[0159] The synthesis method is the same as M62-4, except that M81-4 is used instead of M62-3.

[0160] Mass of the molecular ion [M+H] determined by mass spectrometry analysis + : 864.47 (Theoretical value: 863.40).

[0161] Synthesis of compound M81:

[0162] The synthesis method is the same as M1-5, except that M1-4 is replaced with M81-5.

[0163] Mass of the molecular ion [M+H] determined by mass spectrometry analysis + : 838.75 (Theoretical value: 837.43).

[0164] This invention provides specific synthesis methods for the above-mentioned compounds. For compounds in the following examples (others) that are not given specific synthesis methods, they are also prepared by similar methods, which only require replacing the raw materials. These methods will not be elaborated here. Alternatively, those skilled in the art can also prepare them using other methods in the prior art.

[0165] Theoretical calculations:

[0166] The calculations described in this invention are performed using the Gaussian16 program.

[0167] The ground-state structure of the molecule was optimized at the B3LYP / 6-31G* computational level. The energy levels of the highest occupied orbital (HOMO) and lowest unoccupied orbital (LUMO) in the ground state were calculated using the B3LYP / 6-31G* method. The UV-Vis absorption spectrum of the molecule was obtained using the B3LYP / 6-31G* method in the SMD solvent model (toluene).

[0168] The structure of the lowest triplet excited state of the molecule was optimized using the B3LYP / 6-31G* method. The energy levels of the highest occupied orbital (HOMO) and lowest unoccupied orbital (LUMO) of the molecule in the excited state were calculated using the B3LYP / 6-31G* method. The maximum phosphorescence emission wavelength of the molecule was obtained using the B3LYP / 6-31G* method in the SMD solvent model (toluene). See Table 1 below for details.

[0169] Table 1:

[0170]

[0171]

[0172]

[0173] As shown in Table 1, the T1 of all the low triplet small molecule groups mentioned above is less than 2.40 eV. Detailed Implementation

[0175] An OLED includes a first electrode and a second electrode, and an organic material layer located between the electrodes. This organic material layer can be further divided into multiple regions. For example, the organic material layer may include a hole transport region, a light-emitting layer, and an electron transport region.

[0176] In specific embodiments, a substrate can be used below the first electrode or above the second electrode. The substrate is typically made of glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. Furthermore, thin-film transistors (TFTs) can also be incorporated into the substrate used for displays.

[0177] The first electrode can be formed by sputtering or depositing the material to be used as the first electrode on a substrate. When the first electrode is used as the anode, it can be a transparent conductive oxide material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof. When the first electrode is used as the cathode, it can be a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0178] Organic material layers can be formed on electrodes using methods such as vacuum thermal evaporation, spin coating, and printing. The compounds used as organic material layers can be small organic molecules, large organic molecules, polymers, and combinations thereof.

[0179] The hole transport region is located between the anode and the emissive 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. Alternatively, the hole transport region can be a multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the emissive layer.

[0180] The material for the hole transport region may be selected from, but is 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 as shown in HT-1 to HT-51 below; or any combination thereof.

[0181]

[0182]

[0183]

[0184]

[0185] 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 be one or more compounds of HT-1 to HT-51 mentioned above, or one or more compounds of HI-1 to HI-3 mentioned below; it can also be one or more compounds of HT-1 to HT-51 doped with one or more compounds of HI-1 to HI-3 mentioned below.

[0186]

[0187] The emissive layer includes luminescent dyes (i.e., dopants) that can emit different wavelengths of light, and may also include a host material. The emissive layer can be a monochromatic emissive layer emitting a single color such as red, green, or blue. Multiple monochromatic emissive layers of different colors can be arranged in a planar pattern according to pixel design, or they can be stacked together to form a colored emissive layer. When different colored emissive layers are stacked together, they can be separated from each other or connected to each other. The emissive layer can also be a single colored emissive layer that can simultaneously emit different colors such as red, green, and blue.

[0188] Depending on the technology used, the light-emitting layer material can be various, including fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescence materials. An OLED device can employ a single light-emitting technology or a combination of different technologies. These different light-emitting materials, categorized by technology, can emit light of the same color or different colors.

[0189] In one aspect of the invention, the light-emitting layer employs fluorescent electroluminescence technology. The fluorescent dopant in the light-emitting layer may be selected from, but not limited to, one or more combinations of M1 to M267 listed above.

[0190] In one aspect of the invention, the light-emitting layer employs phosphorescent photoluminescence technology. The main material of the light-emitting layer is selected from, but not limited to, one or more combinations of PH-1 to PH-117.

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197] In one aspect of the invention, the light-emitting layer employs phosphorescent photoluminescence technology. The phosphorescent dopant of the light-emitting layer may be selected from, but is not limited to, one or more combinations of BPD-1 to BPD-16 listed below.

[0198]

[0199]

[0200] In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light-emitting layer. The electron blocking layer may employ, but is not limited to, one or more compounds of HT-1 to HT-51 described above, or one or more compounds of PH-75 to PH-117 described above; or a mixture of one or more compounds of HT-1 to HT-51 and one or more compounds of PH-75 to PH-117 may be employed.

[0201] The OLED organic material layer may also include an electron transport region between the light-emitting layer and the cathode. The electron transport region can be a single-layer electron transport layer (ETL), including single-layer electron transport layers containing only one compound and single-layer electron transport layers containing multiple compounds. Alternatively, the electron transport region can be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0202] In one aspect of the present invention, the electron transport layer material may be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0203]

[0204]

[0205]

[0206]

[0207]

[0208] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light-emitting layer. The hole blocking layer may employ, but is not limited to, one or more compounds of ET-1 to ET-73, or one or more compounds of PH-1 to PH-74; or a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-74 may be employed.

[0209] The device may also include an electron injection layer located between the electron transport layer and the cathode, and the electron injection layer material includes, but is not limited to, one or more combinations of the following.

[0210] LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, Yb.

[0211] The fabrication process of the organic electroluminescent device in this embodiment is as follows:

[0212] Device Example 1

[0213] An organic electroluminescent device includes, sequentially arranged, 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). The fabrication method of this organic electroluminescent device is as follows:

[0214] (1) The glass substrate coated with ITO transparent conductive layer was ultrasonically treated in commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in acetone / ethanol mixed solvent, baked in a clean environment until the moisture was completely removed, cleaned with ultraviolet light and ozone, and bombarded with low-energy cation beam.

[0215] (2) Place the glass substrate with the anode in the vacuum chamber and evacuate it to a vacuum level of less than 1×10⁻⁶. -5 Pa, a mixture of compound HT-4:HI-3 (97 / 3, w / w) was vacuum-deposited on the above anodic layer as a hole injection layer at a deposition rate of 0.1 nm / s and a film thickness of 10 nm.

[0216] (3) The compound HT-4 was vacuum-deposited on the hole injection layer as a hole transport layer at a deposition rate of 0.1 nm / s and a total film thickness of 105 nm.

[0217] (4) The compound PH-75 was vacuum-deposited on the hole transport layer as an electron blocking layer at a deposition rate of 0.1 nm / s and a total film thickness of 5 nm.

[0218] (5) A light-emitting layer is vacuum-deposited on the electron blocking layer. The light-emitting layer comprises a quaternary mixture of host material PH-75:PH-59 (5:4, w / w), sensitizer BPD-1 (doped 13%) and dye (polycyclic aromatic compound M1 provided by the present invention, doped 1%). The total evaporation rate is 0.1 nm / s and the total evaporation film thickness is 35 nm.

[0219] (6) The compound PH-59 was vacuum-deposited on the light-emitting layer as a hole blocking layer at a deposition rate of 0.1 nm / s and a total film thickness of 5 nm.

[0220] (7) A mixture of compound ET-69: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 total film thickness of 25 nm.

[0221] (8) LiF was vacuum-deposited on the electron transport layer as an electron injection layer at a deposition rate of 0.1 nm / s and a thickness of 1 nm.

[0222] (9) An Al layer with a thickness of 150 nm is vacuum-deposited on the electron injection layer as the cathode of the device at a deposition rate of 1 nm / s to obtain the organic electroluminescent device.

[0223] The dyes used in the device comparison examples 1-5 are shown below:

[0224]

[0225] Device Examples 2-10, Device Comparative Examples 1-5

[0226] An organic electroluminescent device is disclosed, which differs from device example 1 only in that the dyes of the light-emitting layer are the compounds shown in Table 1; the other layers, thicknesses, materials and preparation methods are the same as those of device example 1.

[0227] The dyes used in Comparative Examples 1-5 of the devices are D1, D2, D3, D4 and D5 as described above.

[0228] Device performance testing:

[0229] (1) Emission peak value λ max : Measured directly by organic electroluminescent devices;

[0230] (1) LT95 lifespan: tested with a luminance meter at 40mA / cm 2 The initial brightness value of the device under the current density is measured. The current density is kept constant, and the time it takes for the device brightness to drop to 95% of the initial brightness is measured in hours. The LT95 lifetime test value of device comparison example 4 is recorded as 1.0. The ratio of the LT95 lifetime test value of other devices to the LT95 lifetime test value of device comparison example 4 is calculated.

[0231] (2) External quantum efficiency: The device efficiency was measured using the integrating sphere method at 10 mA / cm². 2 The external quantum efficiency (EQE, %) at current density is denoted as 1.0, with the external quantum efficiency test value of device comparison example 4 as 1.0. The ratio of the external quantum efficiency test value of other devices to the external quantum efficiency test value of device comparison example 4 is calculated.

[0232] The test results are shown in Table 2:

[0233] Table 2:

[0234]

[0235]

[0236] As can be seen from the data in Table 2, compared with the compounds of the present invention, D1 and D3 emit green light due to the different parent core skeleton, which is significantly different from the compounds of the present invention in terms of application scenarios. The larger emission wavelength of the dye will result in insufficient energy transfer in the device, which will seriously affect the efficiency and lifespan of the device.

[0237] For compounds D2 and D5, relative to the compounds of the present invention, in X1-X 10 The absence of an N atom at the position results in a molecule with a high HOMO energy level, leading to severe dye trapping in the device and significantly reducing the efficiency of the sensitized device.

[0238] For compound D4, due to the lack of low triplet groups on the parent nucleus, the triplet energy level of the entire molecule is relatively high. At the same time, due to the more planar structure of the molecule, it is easy to aggregate, causing mutual quenching between excitons, resulting in a decrease in efficiency and lifetime compared with the compound of the present invention.

[0239] In summary, this invention, through a special design of its molecular structure, enables the polycyclic aromatic compound to serve as a dye for the luminescent layer, effectively improving efficiency and lifespan, making it a high-performance blue light material.

[0240] Although the invention has been described in conjunction with embodiments, the invention is not limited to the above embodiments. It should be understood that various modifications and improvements can be made by those skilled in the art under the guidance of the inventive concept, and the appended claims summarize the scope of the invention.

Claims

1. A polycyclic aromatic compound having the structure shown in formula (1): In formula (1), ring A and ring B are independently selected from one of unsubstituted or R0-substituted C6-C30 aromatic rings and unsubstituted or R0-substituted C3-C30 heteroaromatic rings. R0 is independently selected from deuterium and R A The RO group comprises one or a combination of two of the following: halogen, cyano, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryl, and C6-C30 aryl; adjacent RO groups may be connected to form a ring or not; each RO group is independently not connected to an adjacent ring structure or is connected to form a ring by a chemical bond; X1, X2, X3, X4, X5, X6, X7, X8, X9, X 10 Each is independently selected from N or CR1, and at least one of them is selected from N; two adjacent R1s are connected in a loop or not connected; R2 represents a single-substituted group up to the maximum allowed number of substituents; R1 and R2 are each independently selected from hydrogen, R A Halogen, cyano, unsubstituted or R 01 Substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R 01 Substituted C3-C20 cycloalkyl, unsubstituted or R 01 Substituted C2-C20 alkenyl, unsubstituted or R 01 Substituted C3-C30 heteroaryl, unsubstituted or R 01 One of the substituted C6-C30 aryl groups; R 01 Each is independently selected from one or a combination of two of the following: deuterium, halogen, cyano, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryl, and C6-C30 aryl; two adjacent R 01 The R can be connected in a loop or not; 01 Each ring is independent and not connected to the adjacent ring structure or is connected to form a ring by chemical bonds; At least one of R0, R1, and R2 is R. A R A It is one of substituted or unsubstituted C6-C60 aryl groups with T1 < 2.40 eV, or substituted or unsubstituted C3-C60 heteroaryl groups with T1 < 2.40 eV, wherein each of the substituted substituents is independently selected from one or a combination of two of deuterium, halogen, cyano, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C1-C20 alkoxy, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl; Y1 and Y2 are each independently selected from single bonds, O or S, n1 and n2 are each independently 0 or 1, and n1+n2 is 1 or 2.

2. The polycyclic aromatic compound according to claim 1, characterized in that, In equation (1), at least one of R0, R1, and R2 is selected from R A The R A It is one of the substituted or unsubstituted C13-C40 aryl groups with T1 < 2.40 eV, or the substituted or unsubstituted C12-C40 heteroaryl groups with T1 < 2.40 eV; Preferably, the R A Selected from one of the following substituted or unsubstituted groups, —* represents the linkage site of the group: The substituents therein are each independently selected from one or a combination of two of the following: deuterium, halogen, cyano, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C1-C20 alkoxy, C3-C20 cycloalkyl, C2-C20 heterocyclic alkyl, C6-C30 aryl, and C3-C30 heteroaryl; preferably, the substituents therein are each independently selected from one or a combination of two of the following: deuterium, halogen, cyano, amino, C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C2-C10 heterocyclic alkyl, C6-C20 aryl, and C3-C20 heteroaryl.

3. The polycyclic aromatic compound according to claim 1 or 2, characterized in that, The structure is selected from the following formulas (1-1), (1-2), (1-3), (1-4), or (1-5): Among them, X2-X 10 The definition of R2 is the same as that in equation (1); Y1 and Y2 are each independently selected from O or S; Z2, Z3, Z4, Z5, Z6, Z7, and Z8 are each independently selected from N or CR3; R3 is independently selected from hydrogen, deuterium, and R A One or a combination of two of the following: halogen, cyano, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryl, and C6-C30 aryl; adjacent R3s may or may not be linked to form a ring. Y3 is selected from O or S.

4. The polycyclic aromatic compound according to claim 1 or 3, characterized in that, X2-X 10 At least one of them is selected from N, and at most four are selected from N, with the remainder selected from CR1; preferably, X3, X5, X8, X 10 At least one of them is selected from N, and the rest are selected from CR1; further preferably, X3, X5, X8, X 10 At most two of them are selected from N, and the rest are selected from CR1; more preferably, X3 and / or X5 are selected from N, and X8, X 10 Selected from N or CR1, the rest selected from CR1; most preferably, X3 and / or X5 are selected from N, X2 and X4 are selected from CH, and X8 and X... 10 Selected from N or CR1, the rest are selected from CR1; Each of R1 is independently selected from hydrogen, R A Halogen, cyano, unsubstituted or R 01 Substituted C1-C10 straight-chain or branched alkyl groups, unsubstituted or R 01 Substituted C3-C10 cycloalkyl, unsubstituted or R 01 Substituted C3-C30 heteroaryl, unsubstituted or R 01 One of the substituted C6-C30 aryl groups; said R 01 Each is independently selected from one of the following: deuterium, halogen, cyano, C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylsilyl, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryl, and C6-C30 aryl. Preferably, each of R1 is independently selected from hydrogen, R A Halogen, cyano, or any of the following groups, —* represents the linkage site of the group:

5. The polycyclic aromatic compound according to claim 3, characterized in that, At most one of Z2 to Z8 is selected from N, and the rest are selected from CR3; preferably, each of Z2 to Z8 is independently selected from CR3; Each of the R3s is independently selected from hydrogen, deuterium, and R. A Halogen, cyano, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C3-C30 heteroaryl, C6-C30 aryl; one or a combination of two of these groups. Preferably, each of the R3s is independently selected from hydrogen, R... A Halogen, cyano, or any of the following groups, —* represents the linkage site of the group:

6. The polycyclic aromatic compound according to claim 1 or 3, characterized in that, Each of R2 is independently selected from hydrogen, R A Halogen, cyano, unsubstituted or R 01 Substituted C1-C10 straight-chain or branched alkyl groups, unsubstituted or R 01 Substituted C3-C10 cycloalkyl, unsubstituted or R 01 Substituted C3-C30 heteroaryl, unsubstituted or R 01 One of the substituted C6-C30 aryl groups; R 01 Each is independently selected from one of the following: deuterium, halogen, cyano, C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylsilyl, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryl, and C6-C30 aryl. Preferably, each of R2 is independently selected from hydrogen, R A Halogen, cyano, or any of the following groups, —* represents the linkage site of the group:

7. The polycyclic aromatic compound according to any one of claims 1-6, characterized in that, The aromatic compound has any one of the following structures:

8. The application of the polycyclic aromatic compound according to any one of claims 1 to 7, wherein the application is as a functional material in organic electronic devices, said organic electronic devices including organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin-film transistors, organic field-effect transistors, information tags, electronic artificial skin sheets, sheet-type scanners, or electronic paper; Preferably, the polycyclic aromatic compound is used as a light-emitting layer material in an organic electroluminescent device, and more preferably as a dopant material in the light-emitting layer.

9. An organic electroluminescent device, comprising a first electrode, a second electrode, and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer comprises a light-emitting layer, and at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron blocking layer, wherein the light-emitting layer comprises a host material and a dopant material, and the dopant material comprises at least one polycyclic aromatic compound as described in any one of claims 1 to 7.

10. An electronic device having a display screen or display panel, the display screen or display panel comprising the organic electroluminescent device of claim 9.

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