Organic electroluminescent material, application thereof and organic electroluminescent device

Abstract

The invention relates to an organic compound, belongs to the technical field of organic electroluminescence, and also relates to an organic electroluminescence device adopting the organic compound. The compound provided by the invention has a structure shown in the specification. The compound disclosed by the invention is simple to prepare and relatively good in thermal stability, and meanwhile, the compound disclosed by the invention can adjust the stability of a material, so that the photoelectric property of a device prepared from the compound disclosed by the invention is finally ensured to be obviously improved. # imgabs0 #

Description

Technical Field

[0001] The invention provides an organic compound, belonging to the technical field of organic electroluminescence, and specifically relates to the application of the organic compound and an organic electroluminescent device using the compound. Background Art

[0002] Organic Light Emission Diodes (OLED) is a device with a sandwich-like structure, including positive and negative electrode film layers and organic functional material layers sandwiched between the positive and negative electrode film layers. Voltage is applied to the positive and negative electrodes of the OLED device, positive charges are injected from the positive electrode, and negative charges are injected from the negative electrode. Under the action of the electric field, the positive and negative charges migrate in the organic layer and meet to combine and emit light. Due to the advantages of high brightness, fast response, wide viewing angle, simple process, and flexibility, OLED devices have attracted much attention in the fields of new display technology and new lighting technology. At present, this technology has been widely used in display panels of new lighting fixtures, smart phones, tablet computers and other products, and will further expand to the application fields of large-size display products such as TVs. It is a new display technology with fast development and high technical requirements.

[0003] As OLED continues to advance in the two major fields of lighting and display, people are paying more attention to the research on its core materials. This is because an OLED device with good efficiency and long life is usually the result of an optimized combination of device structure and various organic materials, which provides great opportunities and challenges for researchers to design and develop functional materials of various structures. Common functional organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, luminescent host materials and luminescent guests (dyes), etc.

[0004] In order to prepare OLED light-emitting devices with lower driving voltage, better luminous efficiency and longer device life, and to continuously improve the performance of OLED devices, it is necessary not only to innovate the structure and manufacturing process of OLED devices, but also to continuously study and innovate the optoelectronic functional materials in OLED devices to prepare functional materials with higher performance. Based on this, the OLED material industry has been committed to developing new organic electroluminescent materials to achieve low starting voltage, high luminous efficiency and better device life. In recent years, people in the industry have continuously tried and explored ways to improve device efficiency and stability. Among them, seeking new materials to improve device performance is the most common way. A large number of novel materials have been developed for use in organic electroluminescent devices. Although it has a certain improvement in device performance, it still has a large amount of carrier accumulation at the interface, and there is also the problem of low device efficiency.

[0005] Therefore, the field is in urgent need of developing organic electroluminescent devices with higher performance, and further developing organic electroluminescent materials, especially host materials, that can provide better photoelectric performance is the direction in which the industry continues to strive for breakthroughs. Summary of the invention

[0006] In view of the deficiencies in the prior art, the purpose of the present invention is to provide an organic electroluminescent material and its application, and an organic electroluminescent device. By designing the molecular structure of the compound, the organic electroluminescent material has excellent carrier transport performance. When used in an organic electroluminescent device, it can effectively improve the life and efficiency of the device and reduce the driving voltage.

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

[0008] In a first aspect, the present invention provides an organic compound having a structure as shown in formula (1):

[0009]

[0010] In formula (1), X is O or S;

[0011] In formula (1), R1, R2, R3, and R4 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, and substituted or unsubstituted C3-C60 heteroaryl;

[0012] Formula (a) is fused to Formula (1) at any pair of sites among R1 and R2, R2 and R3, or R3 and R4 to form a ring, and * represents the connection site;

[0013] In formula (1), A is a structure of formula (b), or A is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C60 heteroaryl;

[0014] When A is a structure of formula (b), formula (a) is fused with formula (1) at the R1 and R2 sites or at the R2 and R3 sites to form a ring;

[0015] In formula (a), B is a structure of formula (b), or B is selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, and substituted or unsubstituted C3-C60 heteroaryl;

[0016] When B is of formula (b), the attachment site of B in formula (a) is the meta position of the attachment site of "—L3-Ar3" in formula (a);

[0017] and one of A and B is a structure of formula (b);

[0018] In formula (a), L3 represents a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group;

[0019] Ar3 is selected from substituted or unsubstituted C6-C60 aryl;

[0020] In formula (b), L1, L2, and L each independently represent a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group;

[0021] Ar1 and Ar2 are independently selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group;

[0022] The substituents substituted in A, B, Ar1, Ar2, Ar3, L1, L2, L3, L, R1, R2, R3, and R4 are each independently selected from at least one of deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde, ester, C1-C20 chain alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0023] More preferably, in formula (1), A is a structure of formula (b); and in formula (a), B is hydrogen.

[0024] More preferably, in formula (1), A is hydrogen; and in formula (a), B is a structure of formula (b).

[0025] It should be noted that, for the sake of convenience, the possible effects of each group / feature are described separately in the present invention, but this does not mean that these groups / features act in isolation. In fact, the reason for obtaining good performance is essentially the optimized combination of the entire molecule, which is the result of the synergistic effect between various groups and structures, rather than the effect of a single group or structure.

[0026] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or with multiple substituents. When there are multiple substituents, they may be selected from different substituents. When the same expression is involved in the present invention, it has the same meaning without special explanation, and the selection range of the substituent is as shown above and will not be repeated one by one.

[0027] In the present invention, the expression of chemical elements, unless otherwise specified, includes the concept of isotopes with the same chemical properties. For example, hydrogen (H) includes 1 H (hydrogen), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C. 13 C, etc.

[0028] In the present invention, the heteroatom of the heteroaryl group is selected from atoms or atomic groups of N, O, S, P, B, Si or Se, preferably N, O or S.

[0029] In the present invention, Represents the connection site. The expression of the ring structure crossed out by “—” or “---------” indicates that the connection site is any position on the ring structure that can form a bond.

[0030] In the present invention, the expression of Ca-Cb represents that the number of carbon atoms in the group is ab. Unless otherwise specified, the number of carbon atoms in the group generally does not include the number of carbon atoms in the substituent.

[0031] In the present invention, “each independently” means that when there are multiple subjects, they may be the same as or different from each other.

[0032] In the present invention, the halogen includes fluorine, chlorine, bromine or iodine.

[0033] In the present invention, the C6-C30 (e.g., C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28) aromatic ring includes a single aromatic ring and a condensed aromatic ring; the single aromatic ring includes a benzene ring, a biphenyl ring or a terphenyl ring, and the condensed aromatic ring means that the ring contains at least two aromatic rings, and the aromatic rings share two adjacent carbon atoms and are condensed with each other, exemplarily including but not limited to: naphthalene ring, anthracene ring, phenanthrene ring, indene ring, fluorene ring and its derivatives (9,9-dimethylfluorene ring, benzofluorene ring, etc.), fluoranthene ring, triphenylene ring, pyrene ring, perylene ring, Ring or tetracene ring, etc.

[0034] The C3-C30 (e.g., C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28) heteroaromatic ring includes a single heteroaromatic ring or a condensed heteroaromatic ring. The single heteroaromatic ring exemplarily includes, but is not limited to, a pyrrole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a furan ring, a thiophene ring, a carbazole ring, and the like. The fused heteroaromatic ring means that the ring structure contains at least one heteroaromatic ring and one aromatic ring (heteroaromatic ring or aromatic ring), and the two share two adjacent atoms to condense each other, and exemplary examples include but are not limited to: quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, benzofuran ring, benzothiophene ring, isobenzofuran ring, isobenzothiophene ring, indole ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring and its derivatives (N-phenylcarbazole ring, benzocarbazole ring, dibenzocarbazole ring, indolecarbazole ring, azacarbazole ring, etc.), acridine ring, phenothiazine ring, phenoxazine ring, hydroacridine ring, etc.

[0035] In the present invention, the C1-C20 chain alkyl group includes C1-C20 straight chain alkyl group and C1-C20 branched chain alkyl group. For example, it can be a chain alkyl group of C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.; preferably a C1-C16 chain alkyl group; more preferably a C1-C10 chain alkyl group; illustratively including but not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, n-heptyl, n-nonyl or n-decyl, etc.

[0036] In the present invention, the C2-C10 alkenyl groups can all be C2, C3, C4, C5, C6, C7, C8, C9, C10 alkenyl groups, which contain at least one C=C, illustratively including but not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0037] Specific examples of the C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) alkoxy groups described in the present invention include monovalent groups obtained by connecting the above-mentioned chain alkyl groups to O.

[0038] In the present invention, the C3-C20 cycloalkyl group may be a cycloalkyl group of C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc., illustratively including but not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0039] A specific example of the C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) alkylsilyl group is a monovalent group in which at least one hydrogen in -SiH3 is replaced by the above-mentioned chain alkyl group; a specific example of the C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) alkylamino group is a monovalent group in which at least one hydrogen in -NH2 is replaced by the above-mentioned chain alkyl group.

[0040] Specific examples of the C2-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) heterocycloalkyl groups of the present invention include monovalent groups in which at least one ring C atom in the above-mentioned cycloalkyl groups is replaced by a heteroatom (e.g., O, S, N or P, etc.), including, but not limited to, epoxy, tetrahydropyrrolyl, tetrahydrofuranyl, tetrahydrothiophenyl, morpholinyl, piperidinyl, etc.

[0041] In the present invention, the C6-C60 aromatic group can be an aromatic group of C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, preferably a C6-C30 aromatic group, including a monocyclic aromatic group or a condensed ring aromatic group. The monocyclic aromatic group means that the group contains at least one phenyl group. When it contains at least two phenyl groups, the phenyl groups are connected by a single bond, and examples thereof include but are not limited to: phenyl, biphenyl, terphenyl, etc.; the condensed aromatic group means that the group contains at least two aromatic rings, and the aromatic rings share two adjacent carbon atoms and are fused to each other, and examples thereof include but are not limited to: naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives (9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirobifluorenyl, benzofluorenyl, etc.), fluoranthenyl, triphenylene, pyrenyl, peryl, The aforementioned groups include all possible connection modes thereof.

[0042] In the present invention, the C3-C60 heteroaryl group can be a heteroaryl group of C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, preferably a C3-C30 heteroaryl group, and more preferably a C4-C20 heteroaryl group, including a monocyclic heteroaryl group or a condensed ring heteroaryl group. The monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains a heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are connected by a single bond, exemplarily including but not limited to: furanyl, thienyl, pyrrolyl, pyridyl, etc. The fused ring heteroaryl group means a group containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring) in the molecule, and the two share two adjacent atoms that are fused to each other, including but not limited to: benzofuranyl, benzothiophenyl, isobenzofuranyl, isobenzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl and its derivatives (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolcarbazolyl, azacarbazolyl, etc.), acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, hydroacridinyl, etc.; the aforementioned groups include all feasible connection modes thereof.

[0043] Specific examples of the C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) arylene group of the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned aryl groups; specific examples of the C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) heteroarylene group include divalent groups obtained by removing one hydrogen atom from the above-mentioned heteroaryl groups.

[0044] Specific examples of the C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) aryloxy groups of the present invention include monovalent groups obtained by connecting the above-mentioned aryl groups to O; specific examples of the C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) heteroaryloxy groups include monovalent groups obtained by connecting the above-mentioned heteroaryl groups to O.

[0045] The C6-C60 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.) arylamino group described in the present invention, preferably the C6-C30 arylamino group, is a monovalent group in which at least one hydrogen in -NH2 is replaced by the above aryl group, and illustratively includes but is not limited to phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrenylamino, biphenylamino and the like.

[0046] The C3-C60 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.) heteroarylamino group described in the present invention, preferably the C3-C30 heteroarylamino group, is a monovalent group in which at least one hydrogen in -NH2 is replaced by the above-mentioned heteroaryl group, and illustratively includes but is not limited to: pyridylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0047] More preferably, the compound of the present invention has a structure as shown in formula (2-1) or (2-2):

[0048]

[0049] Wherein: the definitions of X, B, Ar1, Ar2, Ar3, L1, L2, L3, L, R1, R3, and R4 are the same as those in formulas (1), (a), and (b);

[0050] Preferably, B is selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, and substituted or unsubstituted C3-C60 heteroaryl.

[0051] Still further preferably, in formula (2-1) and (2-2), Ar1 and Ar2 are each independently selected from one of the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, benzofluorenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triazine, triazolyl, pyridyl, pyrimidinyl, quinazoline, quinoxaline, benzimidazolyl, benzindazolyl, benzocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, indolecarbazolyl, azadibenzothiophenyl, azadibenzofuranyl, indenocarbazolyl;

[0052] Ar3 is selected from one of the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl 9-phenylfluorenyl, spirofluorenyl, benzofluorenyl;

[0053] The L3 is a single bond, a phenyl group, a biphenyl group or a naphthyl group, and more preferably L3 is a single bond or a phenyl group;

[0054] The L, L1, and L2 are each independently selected from one of the following groups: a single bond, a phenylene group, a naphthylene group, an anthrylene group, a phenanthrylene group, a biphenylene group, a terphenylene group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a 9-methyl-9-phenylfluorenyl group, a spirofluorenyl group, a benzofluorenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a triazine group, a triazolyl group, a pyridyl group, a pyrimidyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, a benzoindazolyl group, a benzocarbazolyl group, a benzofuranocarbazolyl group, a benzothiophenylocarbazolyl group, an indolecarbazolyl group, an azodibenzothiophenyl group, an azodibenzofuranocarbazolyl group;

[0055] The substituents substituted in the above Ar1, Ar2, and Ar3 are each independently selected from one of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C3-C10 heterocycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl.

[0056] More preferably, in formula (2-1) and (2-2), each of the Bs is independently selected from one of hydrogen, deuterium, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl; preferably, the B is hydrogen;

[0057] The R1, R3, and R4 are each independently selected from one of hydrogen, deuterium, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl; preferably, the R1, R3, and R4 are each independently selected from one of hydrogen, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, phenanthrenyl, triphenylene, More preferably, R1, R3, R4 are each independently selected from hydrogen.

[0058] At the same time, it is further preferred that the compound of the present invention has a structure as shown in formula (3-1), (3-2), (3-3) or (3-4):

[0059]

[0060] Wherein: the definitions of X, A, Ar1, Ar2, Ar3, L1, L2, L3, L, R1, R2, R3, and R4 are the same as those in formula (1), (a), and (b);

[0061] Preferably, A is selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, and substituted or unsubstituted C3-C60 heteroaryl.

[0062] Still further preferably, in formula (3-1), (3-2), (3-3) and (3-4), Ar1 and Ar2 are each independently selected from one of the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, benzofluorenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triazine, triazolyl, pyridyl, pyrimidinyl, quinazoline, quinoxaline, benzimidazolyl, benzindazolyl, benzocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, indolecarbazolyl, azadibenzothiophenyl, azadibenzofuranyl and indenocarbazolyl;

[0063] Ar3 is selected from one of the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl 9-phenylfluorenyl, spirofluorenyl, benzofluorenyl;

[0064] The L3 is a single bond, a phenyl group, a biphenyl group or a naphthyl group, and more preferably L3 is a single bond or a phenyl group;

[0065] The L, L1, and L2 are each independently selected from one of the following groups: a single bond, a phenylene group, a naphthylene group, an anthrylene group, a phenanthrylene group, a biphenylene group, a terphenylene group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a 9-methyl-9-phenylfluorenyl group, a spirofluorenyl group, a benzofluorenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a triazine group, a triazolyl group, a pyridyl group, a pyrimidyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, a benzoindazolyl group, a benzocarbazolyl group, a benzofuranocarbazolyl group, a benzothiophenylocarbazolyl group, an indolecarbazolyl group, an azodibenzothiophenyl group, an azodibenzofuranocarbazolyl group;

[0066] The substituents substituted in the above Ar1, Ar2, and Ar3 are each independently selected from one of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C3-C10 heterocycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl.

[0067] More preferably, in formula (3-1), (3-2), (3-3), and (3-4), each of A is independently selected from one of hydrogen, deuterium, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl; preferably, A is hydrogen;

[0068] The R1, R2, R3, and R4 are each independently selected from one of hydrogen, deuterium, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl; preferably, the R1, R2, R3, and R4 are each independently selected from one of hydrogen, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, phenanthrenyl, triphenylene, More preferably, R1, R2, R3, R4 are each independently selected from hydrogen.

[0069] More preferably, the compounds of the present invention are preferably the following specific compounds, but the present invention is not limited to the specific compounds shown below:

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081] When the compound of the present invention is used as a host material, it has the following beneficial effects compared with the prior art: when the compound is used as a host material of an OLED device, especially a red light host material, the life of the device can be effectively improved while ensuring good device efficiency and driving voltage. When the compound is used as a hole blocking material and an electron transport material, a lower voltage and a higher current efficiency can be obtained.

[0082] The second object of the present invention is to provide an application of the compound described in the first object, wherein the compound is applied to an organic electroluminescent device.

[0083] Preferably, the compound is used as a light-emitting layer material of the organic electroluminescent device, preferably as a light-emitting layer host material of the organic electroluminescent device, and further preferably as an N-type red light host material.

[0084] Preferably, the compound is used as a hole blocking material or an electron transporting material of the organic electroluminescent device.

[0085] The compounds provided by the present invention can also be applied to optical sensors, solar cells, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information tags, electronic artificial skin sheets, sheet-type scanners or electronic paper.

[0086] The third object of the present invention is to provide an organic electroluminescent device, comprising a first electrode, a second electrode and at least one organic layer inserted between the first electrode and the second electrode, wherein the organic layer contains at least one compound described in one of the objects.

[0087] Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer contains at least one compound described in one of the purposes.

[0088] Preferably, the organic layer comprises a hole blocking layer, and the hole blocking layer contains at least one compound described in one of the purposes.

[0089] Preferably, the organic layer comprises an electron transport layer, and the electron transport layer contains at least one compound described in one of the purposes.

[0090] In a specific embodiment, the organic layer may further include a hole transport region and an electron transport region.

[0091] In one embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a thin film transistor (TFT) may also be provided on the substrate used as a display.

[0092] The compound of the present invention has good luminescent properties when used as a luminescent material, especially as a red light host material, and is beneficial to improving the luminescent efficiency of the device. The compound of the present invention can be used as an electron transport layer material or a hole blocking layer material.

[0093] The above-mentioned compound of the present invention is suitable as a functional material of an organic light-emitting device. However, the application scenarios of the compound of the present invention are not limited to organic light-emitting devices. Such organic electronic devices include but are not limited to organic electroluminescent devices, optical sensors, solar cells, lighting elements, information tags, electronic artificial skin sheets, sheet-type scanners or electronic paper, preferably organic electroluminescent devices.

[0094] The present invention also provides an organic electroluminescent device, which comprises a first electrode, a second electrode and at least one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer contains at least one compound represented by the general formula (1) of the present invention.

[0095] The OLED device prepared by using the compound of the present invention has low starting voltage, high luminous efficiency and better service life, and can meet the requirements of current panel and display manufacturers for high-performance materials.

[0096] The compound disclosed in the present invention can be used as a host material, an electron transport material, and a hole blocking material, and is suitable for OLED devices, and can effectively improve the performance of the device. Its good carrier transport performance and high luminous efficiency have potential applications in solving the efficiency roll-off of OLED devices at high current density and extending the life of the device. DETAILED DESCRIPTION

[0097] The technical solution of the present invention is further described in more detail below. It should be understood by those skilled in the art that the specific implementation methods and examples are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0098] Obtaining the compounds of the present invention

[0099] The compound represented by formula (1) of the present invention can be obtained by a known method, for example, by a known organic synthesis method. An exemplary synthesis route is given below, but those skilled in the art can also obtain it by other known methods.

[0100] Synthesis Example 1: Synthesis of Compound N1

[0101]

[0102] (1) Preparation of intermediate N1-2

[0103] The raw material N1-1 (50.4g), 2-chloro-6-fluorophenylboric acid (36.5g), potassium carbonate (83g), tetrakistriphenylphosphine palladium (2.3g) were dissolved in a three-necked flask containing toluene / ethanol / water (600 / 200 / 200mL), replaced with nitrogen, and refluxed for 3 hours. TLC was used to track the completion of the reaction. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by column chromatography to obtain compound N1-2 (43g).

[0104] (2) Preparation of intermediate N1-3

[0105] The intermediate N1-2 (40 g) was dissolved in a three-necked flask containing DMF (200 mL), and cesium carbonate (86 g) was added under stirring at room temperature. After the addition, the reaction was continued under stirring at room temperature for 4 hours. The reaction was completed by TLC tracking. The reaction solution was poured into 1 L of water, and the solid was filtered after stirring. The solid was rinsed with water and ethanol respectively and then dried to obtain the intermediate N1-3 (35 g).

[0106] (3) Preparation of intermediate N1-4

[0107] The intermediate N1-3 (28.2g), pinacol diboron (38.1g), potassium acetate (29g), tris(dibenzyl-BASE acetone)dipalladium (0) (900mg), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (400mg) were dissolved in a three-necked flask containing 500mL 1,4-dioxane, and refluxed for 3h after nitrogen replacement. TLC tracking of the reaction was complete. The reaction solution was cooled to room temperature, the solvent was removed by vacuum rotary evaporation, DCM was dissolved, washed with water, separated, the organic phase was dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the compound N1-4 (31g) was purified by column chromatography.

[0108] (4) Preparation of intermediate N1-5

[0109] Compound N1-4 (30 g), 2-chloro-4,6-diphenyl-1,3,5-triazine (21 g), potassium carbonate (33 g), tetrakistriphenylphosphine palladium (900 mg) were dissolved in a three-necked flask containing toluene / ethanol / water (250 mL / 50 mL / 50 mL), and refluxed for 6 h after replacing nitrogen. TLC was followed to complete the reaction. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with toluene, the combined organic phases were dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and column chromatography was used for purification to obtain intermediate N1-5 (33 g).

[0110] (5) Preparation of intermediate N1-6

[0111] The intermediate N1-5 (30 g) was dissolved in a three-necked flask containing DCM (300 mL), and boron tribromide (31 g) was added dropwise under stirring at room temperature. After the addition was completed, the reaction was continued under stirring at room temperature for 2 hours. The reaction was completed by TLC tracking. The reaction solution was slowly poured into 0.5 L of water for quenching, the liquid was separated, the aqueous phase was extracted with DCM, the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum rotary evaporation to obtain the intermediate N1-6 (25 g).

[0112] (6) Preparation of intermediate N1-7

[0113] The intermediate N1-6 (24 g) was dissolved in a three-necked flask containing toluene, and pyridine (12 g) was added after N2 protection, stirred for a while, cooled to about -20°C, and trifluoromethanesulfonic anhydride (22 g) was added dropwise. After the addition, the mixture was reacted at room temperature for 3 hours. The reaction was completed by TLC tracking. Water was added to quench, the liquids were separated, the aqueous phase was extracted with DCM, the organic phases were combined and dried over anhydrous sodium sulfate, and the crude product was concentrated and washed with ethanol, and filtered to obtain the intermediate N1-7 (23 g).

[0114] (7) Preparation of intermediate N1-8

[0115] The intermediate N1-7 (22g), pinacol borate (14g), potassium acetate (11g), Pd(dppf)2Cl2 (269mg) were dissolved in a three-necked flask containing 500mL 1,4-dioxane, and refluxed for 2 hours after nitrogen replacement. TLC was followed to complete the reaction. The reaction solution was cooled to room temperature, the solvent was removed by vacuum rotary evaporation, DCM was dissolved, washed with water, separated, the organic phase was dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the compound N1-8 (17g) was obtained by column chromatography purification.

[0116] (8) Preparation of target product N1

[0117] The intermediate N1-8 (15g), phenylboronic acid (3.5g), potassium carbonate (11g), tetrakistriphenylphosphine palladium (0.3g) were dissolved in a three-necked flask containing toluene / ethanol / water (200 / 30 / 30mL), and the nitrogen was replaced and refluxed for 5 hours. TLC was used to track the completion of the reaction. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and the compound N1 (10g) was purified by column chromatography. The molecular weight of the obtained compound N1 was calculated to be 525.18, and the measured value m / z was 526.2 (M+1).

[0118] Synthesis Example 2: Synthesis of Compound N23

[0119]

[0120] (1) Preparation of intermediate N23-2

[0121] The raw material N23-1 (50.4g), 2-chloro-6-fluorophenylboric acid (36.5g), potassium carbonate (83g), tetrakistriphenylphosphine palladium (2.3g) were dissolved in a three-necked flask containing toluene / ethanol / water (600 / 200 / 200mL), replaced with nitrogen and refluxed for 4 hours. TLC was used to track the completion of the reaction. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by column chromatography to obtain compound N23-2 (41g).

[0122] (2) Preparation of intermediate N23-3

[0123] The intermediate N23-2 (40 g) was dissolved in a three-necked flask containing DMF (200 mL), and cesium carbonate (86 g) was added under stirring at room temperature. After the addition was completed, the reaction was continued under stirring at room temperature for 2 hours. The reaction was completed by TLC tracking. The reaction solution was poured into 1 L of water, and the solid was filtered after stirring. The solid was rinsed with water and ethanol respectively and then dried to obtain the intermediate N23-3 (34 g).

[0124] (3) Preparation of intermediate N23-4

[0125] The intermediate N23-3 (28.2g), biboric acid pinacol ester (38.1g), potassium acetate (29g), tris (dibenzylidene-BASE acetone) palladium (0) (900mg), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (400mg) were dissolved in a three-necked flask containing 500mL 1,4-dioxane, and refluxed for 4 hours after nitrogen replacement. TLC tracking of the reaction was complete. The reaction solution was cooled to room temperature, the solvent was removed by vacuum rotary evaporation, DCM was dissolved, washed with water, separated, the organic phase was dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the compound N23-4 (32g) was obtained by column chromatography purification.

[0126] (4) Preparation of intermediate N23-5

[0127] Compound N23-4 (30 g), 2-chloro-4,6-diphenyl-1,3,5-triazine (21 g), potassium carbonate (33 g), tetrakistriphenylphosphine palladium (900 mg) were dissolved in a three-necked flask containing toluene / ethanol / water (250 mL / 50 mL / 50 mL), and refluxed for 4 hours after nitrogen replacement. TLC was followed to complete the reaction. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with toluene, the combined organic phases were dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the intermediate N23-5 (31 g) was obtained by column chromatography purification.

[0128] (5) Preparation of intermediate N23-6

[0129] The intermediate N23-5 (30 g) was dissolved in a three-necked flask containing DCM (300 mL), and boron tribromide (31 g) was added dropwise under stirring at room temperature. After the addition was completed, the reaction was continued to stir at room temperature for 3 hours. The reaction was completed by TLC tracking. The reaction solution was slowly poured into 0.5 L of water for quenching, the liquid was separated, the aqueous phase was extracted with DCM, the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum rotary evaporation to obtain the intermediate N23-6 (24 g).

[0130] (6) Preparation of intermediate N23-7

[0131] The intermediate N23-6 (24 g) was dissolved in a three-necked flask containing toluene, and pyridine (12 g) was added after N2 protection. The temperature was cooled to about -20°C, and trifluoromethanesulfonic anhydride (22 g) was added dropwise under stirring. After the addition, the mixture was reacted at room temperature for 3 hours. The reaction was completed by TLC tracking. Water was added to quench the mixture, and the liquids were separated. The aqueous phase was extracted with DCM, and the organic phases were combined and dried over anhydrous sodium sulfate. The crude product was concentrated, stirred and washed with ethanol, and filtered to obtain the intermediate N23-7 (24 g).

[0132] (7) Preparation of intermediate N23-8

[0133] The intermediate N23-7 (22g), bipyralidin (14g), potassium acetate (11g), Pd (dppf) 2Cl2 (269mg) were dissolved in a three-necked flask containing 500mL 1,4-dioxane, and refluxed for 3 hours after nitrogen replacement. TLC was followed to complete the reaction. The reaction solution was cooled to room temperature, the solvent was removed by vacuum rotary evaporation, DCM was dissolved, washed with water, separated, the organic phase was dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the compound N23-8 (16g) was obtained by column chromatography purification.

[0134] (8) Preparation of target product N23

[0135] The intermediate N23-8 (15g), 2-naphthaleneboronic acid (5g), potassium carbonate (11g), tetrakistriphenylphosphine palladium (0.3g) were dissolved in a three-necked flask containing toluene / ethanol / water (200 / 30 / 30mL), and the nitrogen was replaced and refluxed for 4 hours. TLC was followed to complete the reaction. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and the compound N23 (11g) was purified by column chromatography. The molecular weight of the obtained compound N23 was calculated to be 575.20, and the measured value m / z was 576.2 (M+1).

[0136] Synthesis Example 3: Synthesis of Compound N56

[0137]

[0138] (1) Preparation of intermediate N56-2

[0139] The raw material N56-1 (54 g), phenylboric acid (26.8 g), potassium carbonate (83 g), tetrakistriphenylphosphine palladium (2.3 g) were dissolved in a three-necked flask containing toluene / ethanol / water (600 / 200 / 200 mL), and the mixture was refluxed for 3 hours after nitrogen replacement. The reaction was completed by TLC tracking. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and the compound N56-2 (45 g) was obtained by column chromatography purification.

[0140] (2) Preparation of intermediate N56-3

[0141] The intermediate N56-2 (26.8g), biboric acid pinacol ester (38.1g), potassium acetate (29g), tris (dibenzylidene-BASE acetone) palladium (0) (900mg), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (400mg) were dissolved in a three-necked flask containing 500mL 1,4-dioxane, and refluxed for 4 hours after nitrogen replacement. TLC tracking of the reaction was complete. The reaction solution was cooled to room temperature, the solvent was removed by vacuum rotary evaporation, DCM was dissolved, washed with water, separated, the organic phase was dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the compound N56-3 (32g) was obtained by column chromatography purification.

[0142] (3) Preparation of intermediate N56-4

[0143] Compound N56-3 (30 g), 2-chloro-4-(dibenzo[b, d]furan-1-yl)-6-phenyl-1,3,5-triazine (40 g), potassium carbonate (35 g), tetrakistriphenylphosphine palladium (1 g) were dissolved in a three-necked flask containing toluene / ethanol / water (300 mL / 50 mL / 50 mL), replaced with nitrogen, and refluxed for 5 hours. TLC was used to track the completion of the reaction. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with toluene, the combined organic phases were dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the intermediate N56-4 (41 g) was obtained by column chromatography.

[0144] (4) Preparation of intermediate N56-5

[0145] Compound N56-4 (40 g) was dissolved in a three-necked flask containing DCM (300 mL), and NBS (13 g) was added in batches. After the addition, the mixture was stirred at room temperature for 3 hours. The reaction was completed by TLC tracking. Water was added to quench the reaction, and the liquids were separated. The aqueous phase was extracted with DCM, and the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum rotary evaporation. The intermediate N56-5 (34 g) was obtained by column chromatography purification.

[0146] (5) Preparation of intermediate N56-6

[0147] The intermediate N56-5 (33 g), o-fluorophenylboric acid (8 g), potassium carbonate (22 g), tetrakistriphenylphosphine palladium (0.6 g) were dissolved in a three-necked flask containing toluene / ethanol / water (300 / 50 / 50 mL), replaced with nitrogen, and refluxed for 4 hours. TLC was used to track the completion of the reaction. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by column chromatography to obtain compound N56-6 (30 g).

[0148] (6) Preparation of intermediate N56-7

[0149] The intermediate N56-6 (30 g) was dissolved in a three-necked flask containing DCM (300 mL), and boron tribromide (23 g) was added dropwise under stirring at room temperature. After the addition was completed, the reaction was continued to stir at room temperature for 3 hours. The reaction was completed by TLC tracking. The reaction solution was slowly poured into 0.5 L of water for quenching, the liquid was separated, the aqueous phase was extracted with DCM, the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum rotary evaporation to obtain the intermediate N56-7 (23 g).

[0150] (7) Preparation of target product N56

[0151] The intermediate N56-7 (23 g) was dissolved in a three-necked flask containing DMF (200 mL), and cesium carbonate (24 g) was added under stirring at room temperature. After the addition was completed, the reaction was continued under stirring at room temperature for 3 hours. The reaction was completed by TLC tracking. The reaction solution was poured into 1 L of water, and the solid was filtered after stirring. The solid was rinsed with water and ethanol respectively and then dried. The crude product was purified by column chromatography to obtain compound N56 (19 g). The calculated molecular weight of the obtained compound N56 was 615.19, and the measured value m / z was 616.2 (M+1).

[0152] Synthesis Example 4: Synthesis of Compound N67

[0153]

[0154] (1) Preparation of intermediate N67-1

[0155] The raw materials 6-chloro-1-naphthaleneboronic acid (42g), 2-chloro-4,6-diphenyl-1,3,5-triazine (53.4g), potassium carbonate (83g), tetrakistriphenylphosphine palladium (2.3g) were dissolved in a three-necked flask containing toluene / ethanol / water (600 / 200 / 200mL), replaced with nitrogen and refluxed for 4 hours. TLC tracked the completion of the reaction. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by column chromatography to obtain compound N67-1 (67g).

[0156] (2) Preparation of intermediate N67-2

[0157] The intermediate N67-1 (39.3 g), biboric acid pinacol ester (38.1 g), potassium acetate (29 g), tris (dibenzylidene-BASE acetone) palladium (0) (900 mg), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (400 mg) were dissolved in a three-necked flask containing 500 mL of 1,4-dioxane, and refluxed for 5 hours after nitrogen replacement. TLC tracking of the reaction was complete. The reaction solution was cooled to room temperature, the solvent was removed by vacuum rotary evaporation, DCM was dissolved, washed with water, separated, the organic phase was dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the compound N67-2 (42 g) was obtained by column chromatography purification.

[0158] (3) Preparation of intermediate N67-3

[0159] The intermediate N67-2 (42g), 3-chloro-6-methoxy-1-bromonaphthalene (23.4g), potassium carbonate (36g), tetrakistriphenylphosphine palladium (1g) were dissolved in a three-necked flask containing toluene / ethanol / water (600 / 200 / 200mL), replaced with nitrogen, and refluxed for 5 hours. TLC was used to track the completion of the reaction. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by column chromatography to obtain compound N67-3 (41g).

[0160] (4) Preparation of intermediate N67-4

[0161] The intermediate N67-3 (41g), phenylboronic acid (10g), potassium carbonate (31g), tris (dibenzylidene-BASE acetone) palladium (0) (700mg), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (400mg) were dissolved in a three-necked flask containing 500mL 1,4-dioxane and 50mL water, and refluxed for 4 hours after nitrogen replacement. TLC tracking of the reaction was complete. The reaction solution was cooled to room temperature, the solvent was removed by vacuum rotary evaporation, DCM was dissolved, washed with water, separated, the organic phase was dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the compound N67-4 (40g) was purified by column chromatography.

[0162] (5) Preparation of intermediate N67-5

[0163] The intermediate N67-4 (40 g) was dissolved in a three-necked flask containing DCM (300 mL), and NBS (12 g) was added in batches. After the addition, the mixture was stirred at room temperature for 3 hours. The reaction was completed by TLC tracking. Water was added to quench the reaction, the liquid was separated, the aqueous phase was extracted with DCM, the organic phases were combined and dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the intermediate N67-5 (40 g) was obtained by column chromatography purification.

[0164] (6) Preparation of intermediate N67-6

[0165] The intermediate N67-5 (40g), o-fluorophenylboric acid (8.4g), potassium carbonate (25g), tetrakistriphenylphosphine palladium (0.7g) were dissolved in a three-necked flask containing toluene / ethanol / water (300 / 50 / 50mL), replaced with nitrogen and refluxed for 4 hours. TLC was followed to complete the reaction. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by column chromatography to obtain compound N67-6 (37g).

[0166] (7) Preparation of intermediate N67-7

[0167] The intermediate N67-6 (37 g) was dissolved in a three-necked flask containing DCM (400 mL), and boron tribromide (27 g) was added dropwise under stirring at room temperature. After the addition was completed, the reaction was continued to stir at room temperature for 3 hours. The reaction was completed by TLC tracking. The reaction solution was slowly poured into 0.5 L of water for quenching, the liquid was separated, the aqueous phase was extracted with DCM, the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum rotary evaporation to obtain the intermediate N67-7 (29 g).

[0168] (8) Preparation of target product N67

[0169] The intermediate N67-7 (29 g) was dissolved in a three-necked flask containing DMF (300 mL), and cesium carbonate (28 g) was added under stirring at room temperature. After the addition was completed, the reaction was continued under stirring at room temperature for 3 hours. The reaction was completed by TLC tracking. The reaction solution was poured into 1 L of water, and the solid was filtered after stirring. The solid was rinsed with water and ethanol respectively and then dried. The crude product was purified by column chromatography to obtain compound N67 (19 g). The molecular weight of the obtained compound N67 was calculated to be 651.23, and the measured value m / z was 652.2 (M+1).

[0170] Synthesis Example 5: Synthesis of Compound N80

[0171]

[0172] (1) Preparation of intermediate N80-1

[0173] The raw materials 3-chloro-6-methoxy-1-bromonaphthalene (54 g), bipyralidin (77 g), potassium acetate (58 g), Pd(dppf)2Cl2 (1.5 g) were dissolved in a three-necked flask containing 500 mL of 1,4-dioxane, and refluxed for 3 hours after nitrogen replacement. TLC was followed to complete the reaction. The reaction solution was cooled to room temperature, the solvent was removed by vacuum rotary evaporation, DCM was dissolved, washed with water, separated, the organic phase was dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the compound N80-1 (55 g) was obtained by column chromatography purification.

[0174] (2) Preparation of intermediate N80-2

[0175] Compound N80-1 (55 g), 2-chloro-4-(dibenzo[b, d]furan-4-yl)-6-phenyl-1,3,5-triazine (62 g), potassium carbonate (72 g), tetrakistriphenylphosphine palladium (2 g) were dissolved in a three-necked flask containing toluene / ethanol / water (600 mL / 200 mL / 200 mL), and refluxed for 4 hours after nitrogen replacement. TLC was followed to complete the reaction. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with toluene, the combined organic phases were dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the intermediate N80-2 (80 g) was obtained by column chromatography purification.

[0176] (3) Preparation of intermediate N80-3

[0177] The intermediate N80-2 (80g), biboric acid pinacol ester (59g), potassium acetate (45g), tris (dibenzylidene-BASE acetone) palladium (0) (1.4g), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (600mg) were dissolved in a three-necked flask containing 1000mL 1,4-dioxane, and refluxed for 4h after nitrogen replacement. TLC tracking of the reaction was complete. The reaction solution was cooled to room temperature, the solvent was removed by vacuum rotary evaporation, DCM was dissolved, washed with water, separated, the organic phase was dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the compound N80-3 (75g) was purified by column chromatography.

[0178] (4) Preparation of intermediate N80-4

[0179] The intermediate N80-3 (75g), phenylboronic acid (15g), potassium carbonate (51g), tetrakistriphenylphosphine palladium (1.4g) were dissolved in a three-necked flask containing toluene / ethanol / water (500 / 50 / 50mL), replaced with nitrogen and refluxed for 4 hours. TLC was followed to complete the reaction. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by column chromatography to obtain compound N80-4 (61g).

[0180] (5) Preparation of intermediate N80-5

[0181] The intermediate N80-4 (60 g) was dissolved in a three-necked flask containing DCM (600 mL), and NBS (20 g) was added in batches. After the addition, the mixture was stirred at room temperature for 3 hours. The reaction was completed by TLC tracking. Water was added to quench the reaction, the liquid was separated, the aqueous phase was extracted with DCM, the organic phases were combined and dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the intermediate N80-5 (58 g) was obtained by column chromatography purification.

[0182] (6) Preparation of intermediate N80-6

[0183] The intermediate N80-5 (58g), o-fluorophenylboric acid (8g), potassium carbonate (38g), tetrakistriphenylphosphine palladium (1g) were dissolved in a three-necked flask containing toluene / ethanol / water (500 / 50 / 50mL), replaced with nitrogen and refluxed for 6 hours. TLC was used to track the completion of the reaction. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by column chromatography to obtain compound N80-6 (52g).

[0184] (7) Preparation of intermediate N80-7

[0185] The intermediate N80-6 (52 g) was dissolved in a three-necked flask containing DCM (500 mL), and boron tribromide (40 g) was added dropwise under stirring at room temperature. After the addition was completed, the reaction was continued to stir at room temperature for 3 hours. The reaction was completed by TLC tracking. The reaction solution was slowly poured into 0.5 L of water for quenching, the liquid was separated, the aqueous phase was extracted with DCM, the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum rotary evaporation to obtain the intermediate N80-7 (40 g).

[0186] (8) Preparation of target product N80

[0187] The intermediate N80-7 (40 g) was dissolved in a three-necked flask containing DMF (400 mL), and cesium carbonate (41 g) was added under stirring at room temperature. After the addition was completed, the reaction was continued under stirring at room temperature for 3 hours. The reaction was completed by TLC tracking. The reaction solution was poured into 2L of water, and the solid was filtered after stirring. The solid was rinsed with water and ethanol respectively and then dried. The crude product was purified by column chromatography to obtain compound N80 (31 g). The molecular weight of the obtained compound N67 was calculated to be 615.19, and the measured value m / z was 616.2 (M+1).

[0188] Synthesis Example 6: Synthesis of Compound N100

[0189]

[0190] (1) Preparation of intermediate N100-1

[0191] The raw materials 5-chloro-7-bromonaphthol (51.2 g), phenylboronic acid (26.8 g), potassium carbonate (83 g), tetrakistriphenylphosphine palladium (2.3 g) were dissolved in a three-necked flask containing toluene / ethanol / water (600 / 200 / 200 mL), replaced with nitrogen, and refluxed for 6 hours. TLC was used to track the completion of the reaction. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by column chromatography to obtain compound N100-1 (30 g).

[0192] (2) Preparation of intermediate N100-2

[0193] Compound N100-1 (30 g), intermediate N67-2 (57 g), potassium carbonate (49 g), tetrakistriphenylphosphine palladium (1.3 g) were dissolved in a three-necked flask containing toluene / ethanol / water (300 mL / 50 mL / 50 mL), and refluxed for 8 hours after nitrogen replacement. TLC was followed to complete the reaction. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with toluene, the combined organic phases were dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the intermediate N100-2 (41 g) was obtained by column chromatography purification.

[0194] (3) Preparation of intermediate N100-3

[0195] The intermediate N100-2 (40 g) was dissolved in a three-necked flask containing DCM (400 mL), and NBS (13 g) was added in batches. After the addition, the mixture was stirred at room temperature for 2 hours. The reaction was completed by TLC tracking. Water was added to quench the reaction, the liquid was separated, the aqueous phase was extracted with DCM, the organic phases were combined and dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the intermediate N100-3 (32 g) was obtained by column chromatography purification.

[0196] (4) Preparation of intermediate N100-4

[0197] Compound N100-3 (30 g), o-fluorophenylboric acid (6.5 g), potassium carbonate (19 g), tetrakistriphenylphosphine palladium (0.5 g) were dissolved in a three-necked flask containing toluene / ethanol / water (300 / 50 / 50 mL), and refluxed for 7 hours after nitrogen replacement. TLC was used to track the completion of the reaction. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by column chromatography to obtain compound N100-4 (19 g).

[0198] (5) Preparation of target product N100

[0199] The intermediate N100-4 (19 g) was dissolved in a three-necked flask containing DMF (200 mL), and cesium carbonate (18 g) was added under stirring at room temperature. After the addition was completed, the reaction was continued under stirring at room temperature for 3 hours. The reaction was completed by TLC tracking. The reaction solution was poured into 1 L of water, and the solid was filtered after stirring. The solid was rinsed with water and ethanol respectively and then dried. The crude product was purified by column chromatography to obtain compound N100 (16 g). The calculated molecular weight of the obtained compound N100 was 651.23, and the measured value m / z was 652.2 (M+1).

[0200] Synthesis Example 7: Synthesis of Compound N114

[0201]

[0202] (1) Preparation of intermediate N114-1

[0203] The intermediate N1-4 (37.4g), 2-(3-chloro-1-naphthyl)-4,6-diphenyl-1,3,5-triazine (39.3g), potassium carbonate (40g), tris(dibenzylidene-BASE acetone)dipalladium (0) (900mg), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (400mg) were dissolved in a three-necked flask containing 500mL 1,4-dioxane and 50mL water, and refluxed for 4 hours after nitrogen replacement. TLC tracking of the reaction was complete. The reaction solution was cooled to room temperature, the solvent was removed by vacuum rotary evaporation, DCM was dissolved, washed with water, separated, the organic phase was dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the compound N114-1 (55g) was purified by column chromatography.

[0204] (2) Preparation of intermediate N114-2

[0205] The intermediate N114-1 (55 g) was dissolved in a three-necked flask containing DCM (500 mL), and boron tribromide (45 g) was added dropwise under stirring at room temperature. After the addition was completed, the reaction was continued to stir at room temperature for 3 hours. The reaction was completed by TLC tracking. The reaction solution was slowly poured into 1L of water for quenching, the liquid was separated, the aqueous phase was extracted with DCM, the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum rotary evaporation to obtain the intermediate N114-2 (45 g).

[0206] (3) Preparation of intermediate N114-3

[0207] The intermediate N114-2 (45 g) was dissolved in a three-necked flask containing toluene, and pyridine (18 g) was added after N2 protection. The temperature was cooled to about -20°C, and trifluoromethanesulfonic anhydride (32 g) was added dropwise under stirring. After the addition, the mixture was reacted at room temperature for 3 hours. The reaction was completed by TLC tracking. Water was added to quench the mixture, and the liquids were separated. The aqueous phase was extracted with DCM, and the organic phases were combined and dried over anhydrous sodium sulfate. The crude product was concentrated, stirred and washed with ethanol, and filtered to obtain the intermediate N114-3 (47 g).

[0208] (4) Preparation of intermediate N114-4

[0209] The intermediate N114-3 (47 g), pinacol diboron (25 g), potassium acetate (19 g), Pd(dppf)2Cl2 (500 mg) were dissolved in a three-necked flask containing 500 mL of 1,4-dioxane, and refluxed for 4 hours after nitrogen replacement. TLC was followed to complete the reaction. The reaction solution was cooled to room temperature, the solvent was removed by vacuum rotary evaporation, DCM was dissolved, washed with water, separated, the organic phase was dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the compound N114-4 (37 g) was obtained by column chromatography purification.

[0210] (5) Preparation of target product N114

[0211] The intermediate N114-4 (10 g), phenylboronic acid (2 g), potassium carbonate (6 g), tetrakistriphenylphosphine palladium (0.2 g) were dissolved in a three-necked flask containing toluene / ethanol / water (200 / 30 / 30 mL), and the mixture was refluxed for 4 hours after nitrogen replacement. The reaction was completed by TLC tracking. The reaction solution was cooled to room temperature, separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was removed by vacuum rotation, and the compound N114 (8 g) was obtained by column chromatography purification. The molecular weight of the obtained compound N114 was calculated to be 651.23, and the measured value m / z was 652.2 (M+1).

[0212] Synthesis Example 8: Synthesis of Compound N189

[0213]

[0214] The intermediate N1-8 (10g), 10-chlorobenzo[KL]xanthene (4.4g), potassium carbonate (7g), tris(dibenzylidene-BASE acetone)dipalladium (0) (200mg), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (200mg) were dissolved in a three-necked flask containing 200mL 1,4-dioxane and 20mL water, and refluxed for 6 hours after nitrogen replacement. TLC tracking of the reaction was complete. The reaction solution was cooled to room temperature, the solvent was removed by vacuum rotary evaporation, DCM was dissolved, washed with water, separated, the organic phase was dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum rotary evaporation, and the compound N189 (9g) was purified by column chromatography. The molecular weight of the obtained compound N189 was calculated to be 665.21, and the measured value m / z was 666.2 (M+1).

[0215] Device Implementation Method

[0216] OLED includes a first electrode, a second electrode, and an organic material layer between the electrodes. The organic material can be divided into multiple regions. For example, the organic material layer can include a hole transport region, a light emitting layer, and an electron transport region.

[0217] In a specific embodiment, the first electrode can be formed by sputtering or depositing a material used as the first electrode on a substrate. When the first electrode is used as an anode, transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO) and any combination thereof can be used. When the first electrode is used as a cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and any combination thereof can be used.

[0218] The organic layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic layer can be an organic small molecule, an organic macromolecule, a polymer, and a combination thereof.

[0219] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a hole transport layer (HTL) of a single-layer structure, including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multi-layer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0220] The material of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, wherein the aromatic amine derivatives include compounds shown in HT-1 to HT-50 below; or any combination thereof.

[0221]

[0222]

[0223]

[0224] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can use one or more compounds of HT-1 to HT-50 mentioned above, or one or more compounds of HI-1 to HI-3 described below; or one or more compounds of HT-1 to HT-50 can be doped with one or more compounds of HI-1 to HI-3 described below.

[0225]

[0226] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a host material (Host). The light-emitting layer can be a monochrome light-emitting layer that emits a single color such as red, green, and blue. A plurality of monochrome light-emitting layers of different colors can be arranged in a plane according to a pixel pattern, or they can be stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[0227] According to different technologies, the light-emitting layer material can be made of different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescent materials. In an OLED device, a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be used. These different light-emitting materials classified by technology can emit light of the same color or different colors.

[0228] In one aspect of the present invention, the light-emitting layer adopts fluorescent electroluminescence technology. The fluorescent host material of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFH-1 to BFH-17 listed below.

[0229]

[0230] In one aspect of the present invention, the light-emitting layer adopts fluorescent electroluminescence technology. The fluorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFD-1 to BFD-24 listed below.

[0231]

[0232]

[0233] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of RPD-1 to RPD-28 listed below.

[0234]

[0235]

[0236] The electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region may also be a multi-layer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0237] In one aspect of the present invention, the electron transport layer material can be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0238]

[0239]

[0240]

[0241]

[0242] The device may further include an electron injection layer located between the electron transport layer and the cathode. Materials for the electron injection layer include, but are not limited to, one or more combinations of the following.

[0243] Liq, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Yb.

[0244] The cathode is a metal such as a magnesium-silver mixture, LiF / Al, ITO, a metal mixture, or an oxide.

[0245] Compounds D1 and D2 were synthesized based on the method reported in CN113316627A; compound D3 was synthesized based on the method reported in CN113549059A; compounds D4 and D5 were synthesized based on the method reported in CN114671835A, and their structural formulas are as follows. The specific process will not be repeated here.

[0246]

[0247] Device Embodiment

[0248] Device Example 1

[0249] This embodiment provides an organic electroluminescent device, and the specific preparation method is as follows:

[0250] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone:ethanol, baked in a clean environment until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam; the glass substrate with the ITO anode was placed in a vacuum chamber and evacuated to 10 -5Pa, on the above-mentioned anode layer film, vacuum thermally evaporate 10nm of HT-4:HI-3 (97 / 3, w / w) mixture as a hole injection layer; 60nm of compound HT-4 as a hole transport layer; 60nm of compound HT-47 as an electron blocking layer material of the device; the following compound H-1 and the compound N1 of the present invention listed in Table 1 are respectively introduced into a small chamber of a vacuum vapor deposition device as the first and second main compounds, and the compound RPD-8 is introduced into another small chamber as a dopant, and the two main materials are evaporated at a rate of 1:1, and the dopant is doped at a doping amount of 3wt% relative to the total amount of the main and the dopant to form a light-emitting layer with a thickness of 40nm on the electron blocking layer; 5nm of ET-17 is used as the hole blocking layer of the device; 25nm of the compound ET-69:ET-57 (50 / 50, w / w) mixture is used as the electron transport layer; 1nm of LiF is used as the electron injection layer; 150nm of metal aluminum is used as the cathode. The total evaporation rate of all organic layers and LiF was controlled at 0.1 nm / sec, and the evaporation rate of the metal electrode was controlled at 1 nm / sec.

[0251] The difference between Examples 2-10 and Comparative Examples 1-5 and Example 1 is that the second main material N1 is replaced by other compounds, as shown in Table 1 for details.

[0252] The material structure of the first host compound H-1 is as follows, and it can be obtained from the market.

[0253]

[0254] Performance Testing

[0255] The following performance tests were performed on the organic electroluminescent devices prepared in the above examples and comparative examples:

[0256] The device voltage and efficiency are at a brightness of 3000cd / m 2 The device life (LT97) test is as follows: maintain 60mA / cm 2 The current is constant and the time it takes for the brightness of the organic electroluminescent device to drop to 97% of the initial brightness is measured in hours.

[0257] The above test results are shown in Table 1.

[0258] Table 1:

[0259]

[0260]

[0261] As shown in Table 1, the organic electroluminescent material provided by the present invention has excellent carrier injection and transport performance. It is used as a phosphorescent host material for an organic electroluminescent device, which can effectively improve the efficiency, lifespan and operating voltage of the device. The specific reason is unclear. It is speculated from the device performance that it may be the special linking mode of this triazine with benzodibenzofuran and aromatic ring. As an N-type host, good electron injection and migration characteristics can be obtained. The lengthened molecular axial length is conducive to improving the light extraction effect in the device, and the oxygen heteroatom may be conducive to accelerating the exciton energy transfer from the host to the dye, thereby obtaining better device performance. Compared with the molecules D1 and D2 in Comparative Examples 1 and 2, the triazine in the patent of the present invention is located on the benzene ring side of benzodibenzofuran, and the aromatic ring is located on the naphthalene ring side of benzodibenzofuran. Such connection is conducive to maintaining the overall planar conjugation of the molecule and the overall axial length of the molecule, which is conducive to the improvement of electron mobility and the light extraction performance of the device. Compared with the molecules D3, D4 and D5 in Comparative Examples 3, 4 and 5, the special connection mode of the molecules D3, D4 and D5 greatly destroys the planarity of their molecular structures, thereby reducing the electron mobility as an N-type host, thereby affecting the device performance.

[0262] The above experimental data show that the novel organic material of the present invention is used as the red light host material of the organic electroluminescent device and is an organic light-emitting material with good performance and has broad application prospects.

[0263] The present invention illustrates the detailed method of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned detailed method, that is, it does not mean that the present invention must rely on the above-mentioned detailed method to be implemented. Although the present invention is described in conjunction with the embodiments, the present invention is not limited to the above-mentioned embodiments. It should be understood that under the guidance of the concept of the present invention, those skilled in the art can make various modifications and improvements. The attached claims summarize the scope of the present invention. The equivalent replacement of the raw materials of the product of the present invention, the addition of auxiliary components, the selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic compound, characterized in that It has the structure shown in the following formula (1): In formula (1), X is O or S; In formula (1), R1, R2, R3, and R4 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, and substituted or unsubstituted C3-C60 heteroaryl; Formula (a) is fused to Formula (1) at any pair of sites among R1 and R2, R2 and R3, or R3 and R4 to form a ring, and * represents the connection site; In formula (1), A is a structure of formula (b), or A is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C60 heteroaryl; When A is a structure of formula (b), formula (a) is fused with formula (1) at the R1 and R2 sites or at the R2 and R3 sites to form a ring; In formula (a), B is a structure of formula (b), or B is selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, and substituted or unsubstituted C3-C60 heteroaryl; When B is of formula (b), the connection site of B in formula (a) is the meta position of the connection site of "—L3-Ar3" in formula (a); and one of A and B is a structure of formula (b); In formula (a), L3 represents a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group; Ar3 is selected from substituted or unsubstituted C6-C60 aryl; In formula (b), L1, L2, and L each independently represent a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group; Ar1 and Ar2 are independently selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group; The substituents substituted in A, B, Ar1, Ar2, Ar3, L1, L2, L3, L, R1, R2, R3, and R4 are each independently selected from at least one of deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde, ester, C1-C20 chain alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

2. The organic compound according to claim 1, characterized in that In formula (1), A is a structure of formula (b); and in formula (a), B is hydrogen; Alternatively, in formula (1), A is hydrogen; and in formula (a), B is a structure of formula (b).

3. The organic compound according to claim 1, characterized in that Having a structure as shown in formula (2-1) or (2-2): Wherein: the definitions of X, B, Ar1, Ar2, Ar3, L1, L2, L3, L, R1, R3, and R4 are the same as those in formulas (1), (a), and (b); Preferably, B is selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, and substituted or unsubstituted C3-C60 heteroaryl.

4. The organic compound according to claim 3, characterized in that The Ar1 and Ar2 are each independently selected from one of the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, benzofluorenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triazine, triazolyl, pyridyl, pyrimidinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzindazolyl, benzocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, indolecarbazolyl, azadibenzothiophenyl, azadibenzofuranyl, indenocarbazolyl; Ar3 is selected from one of the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl 9-phenylfluorenyl, spirofluorenyl, benzofluorenyl; The L3 is a single bond, a phenyl group, a biphenyl group or a naphthyl group, and more preferably L3 is a single bond or a phenyl group; The L, L1, and L2 are each independently selected from one of the following groups: a single bond, a phenylene group, a naphthylene group, an anthrylene group, a phenanthrylene group, a biphenylene group, a terphenylene group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a 9-methyl-9-phenylfluorenyl group, a spirofluorenyl group, a benzofluorenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a triazine group, a triazolyl group, a pyridyl group, a pyrimidyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, a benzoindazolyl group, a benzocarbazolyl group, a benzofuranocarbazolyl group, a benzothiophenylocarbazolyl group, an indolecarbazolyl group, an azodibenzothiophenyl group, an azodibenzofuranocarbazolyl group; The substituents substituted in the above Ar1, Ar2, and Ar3 are each independently selected from one of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C3-C10 heterocycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl.

5. The organic compound according to claim 3 or 4, characterized in that Each of the Bs is independently selected from one of hydrogen, deuterium, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl; Preferably, B is hydrogen; The R1, R3, and R4 are each independently selected from one of hydrogen, deuterium, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl; Preferably, R1, R3, and R4 are each independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, phenanthrenyl, triphenylene, quinolinyl, pyridyl or quinolyl; More preferably, said R1, R3, and R4 are each independently selected from hydrogen.

6. The organic compound according to claim 1, characterized in that Having a structure as shown in formula (3-1), (3-2), (3-3) or (3-4): Wherein: the definitions of X, A, Ar1, Ar2, Ar3, L1, L2, L3, L, R1, R2, R3, and R4 are the same as those in formula (1), (a), and (b); Preferably, A is selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, and substituted or unsubstituted C3-C60 heteroaryl.

7. The organic compound according to claim 6, characterized in that The Ar1 and Ar2 are each independently selected from one of the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, benzofluorenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triazine, triazolyl, pyridyl, pyrimidinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzindazolyl, benzocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, indolecarbazolyl, azadibenzothiophenyl, azadibenzofuranyl, indenocarbazolyl; Ar3 is selected from one of the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl 9-phenylfluorenyl, spirofluorenyl, benzofluorenyl; The L3 is a single bond, a phenyl group, a biphenyl group or a naphthyl group, and more preferably L3 is a single bond or a phenyl group; The L, L1, and L2 are each independently selected from one of the following groups: a single bond, a phenylene group, a naphthylene group, an anthrylene group, a phenanthrylene group, a biphenylene group, a terphenylene group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a 9-methyl-9-phenylfluorenyl group, a spirofluorenyl group, a benzofluorenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a triazine group, a triazolyl group, a pyridyl group, a pyrimidyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, a benzoindazolyl group, a benzocarbazolyl group, a benzofuranocarbazolyl group, a benzothiophenylocarbazolyl group, an indolecarbazolyl group, an azodibenzothiophenyl group, an azodibenzofuranocarbazolyl group; The substituents substituted in the above Ar1, Ar2, and Ar3 are each independently selected from one of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C3-C10 heterocycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl.

8. The organic compound according to claim 6 or 7, characterized in that Each of the A's is independently selected from one of hydrogen, deuterium, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl; Preferably, A is hydrogen; The R1, R2, R3, and R4 are each independently selected from one of hydrogen, deuterium, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl; Preferably, R1, R2, R3, and R4 are each independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, phenanthrenyl, triphenylene, quinolinyl, pyridyl or quinolyl; More preferably, said R1, R2, R3, and R4 are each independently selected from hydrogen.

9. The organic compound according to claim 1, characterized in that Selected from the following compounds:

10. Use of the organic compound according to any one of claims 1 to 9, wherein the use is as a functional material in an organic electronic device, wherein the organic electronic device is selected from an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner or an electronic paper; Preferably, the organic compound is used as a light-emitting host material in an organic electroluminescent device.

11. 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, characterized in that: The light-emitting functional layer contains the organic compound according to any one of claims 1 to 9; Preferably, the light-emitting functional layer includes a light-emitting layer and at least one of an electron blocking layer, a hole injection layer, a hole transport layer, and an electron transport layer. The light-emitting layer includes a main material and a doping material, and the main material includes the organic compound described in any one of claims 1 to 9.

12. An electronic device having a display screen or a display panel, characterized in that: The display screen or display panel adopts the organic electroluminescent device according to claim 9.

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