Heterospiro compound and organic light-emitting device

Abstract

The invention discloses a heterocyclic spiro compound and an organic light-emitting device, the heterocyclic spiro compound has a structural general formula as shown in formula (1): in the formula (1), ring A and ring B are independently selected from naphthalene rings or benzene rings; one of X and Y is S, and the other one is O or S; x1, X2 and X3 are respectively and independently selected from N or CR5, and at least one is N; and Ar1, Ar2 and Ar3 are independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C16 cycloalkyl fused C6-C30 aryl group, and a substituted or unsubstituted C2-C30 heteroaryl group. The compound has the advantages of high optical and electrical stability, low driving voltage, high luminous efficiency, long device service life and the like, can be used as a hole blocking material and an electron transport layer material, and is used in OLED luminescent devices.

Description

Technical Field

[0001] This application belongs to the field of organic light-emitting technology, and specifically relates to a heterospirocyclic compound and an organic light-emitting device. Background Technology

[0002] Currently, organic light-emitting diodes (OLEDs), as a next-generation display and lighting technology, are receiving widespread attention and demonstrating significant application potential. However, despite the continued growth in market demand, OLEDs still require further optimization in key performance indicators such as luminous efficiency, operating voltage, and lifespan.

[0003] From a device structure perspective, OLEDs typically employ a "sandwich" configuration where multiple layers of organic functional films are sandwiched between two metal electrodes. Under the influence of an electric field, holes and electrons are injected from the anode and cathode, respectively, migrate, recombine in the emissive layer, and release energy in the form of light or heat, thereby achieving light emission.

[0004] Organic functional materials are a core component of OLED devices, and their properties, such as thermal stability, photochemical stability, electrochemical stability, quantum efficiency, film quality, crystallization behavior, and color purity, have a decisive impact on the overall performance of the device. In the prior art, patent KR1020150129282A discloses a bis(triazine) electron transport material linked by spirofluorene. This material improves the electrochemical stability of organic functional materials to some extent and contributes to extending device lifespan. However, this type of material still has significant shortcomings in terms of driving voltage and photoelectric stability, which urgently need improvement. Improving the electrochemical stability and conductivity of the material not only helps to reduce the device driving voltage and reduce electrochemical damage to the electrodes and organic material layers, but also enhances the device's tolerance to external environmental factors, thereby comprehensively improving the luminous efficiency and lifespan of the OLED.

[0005] Therefore, developing new high-performance organic functional materials is of great significance for promoting the further development of OLED technology. Summary of the Invention

[0006] This application aims to at least solve one of the technical problems existing in the prior art. To this end, this application proposes a heterospirocyclic compound and an organic light-emitting device. The first aspect of this application provides a heterospirocyclic compound.

[0007] Specifically, the structure of the heterospirocyclic compound is shown in formula (1):

[0008] Equation (1) In formula (1), ring A and ring B are independently selected from naphthalene ring or benzene ring; One of X and Y is S, and the other is O or S; X1, X2, and X3 are each independently selected from N or CR5, and at least one of them is N; L1 is selected from any of the structures shown in equations (A-1) to (A-3): ; R1 to R8 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C2-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphinyl or C6-C60 arylamine; a~c and e~g are each independently selected from integers from 0 to 4; d is selected from integers from 0 to 3; Ar1, Ar2, and Ar3 are independently selected from substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C16 cycloalkyl-fused C6-C30 aryl groups, and substituted or unsubstituted C2-C30 heteroaryl groups. The substitutions in Ar1, Ar2, and Ar3 are each independently selected from at least one of deuterium, halogen, cyano, isocyano, phosphin, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C30 substituted or unsubstituted alkyl, and C3-C30 heteroaryl, wherein the number of substitutions ranges from monosubstituted to the maximum number of substitutions. The heteroatoms in the heteroaryl, heteroalkyl, and heterocycloalkyl groups are independently selected from at least one of O, S, N, Se, Si, and Ge.

[0009] Compared with the prior art, the beneficial effects of this application are as follows: The heterospirocyclic compound of this application exhibits excellent optical and electrical stability, significantly reduces driving voltage, significantly improves luminous efficiency, and markedly extends device lifetime. These superior properties make it suitable as an electron transport material or hole blocking layer material for widespread application in OLED light-emitting devices. Furthermore, the low melting point of this heterospirocyclic compound allows it to be used as a molten material, which helps improve the stability of material evaporation and facilitates industrial production. Given these characteristics, this spirocyclic compound demonstrates application potential as a hole blocking layer material and electron transport layer material in the OLED industry, and also shows feasibility for application in the AMOLED industry, providing a new material option for technological innovation and industrial upgrading in related fields. Detailed Implementation

[0010] To enable those skilled in the art to more clearly understand the technical solutions described in this application, the following embodiments are provided for illustration. It should be noted that the following embodiments do not constitute a limitation on the scope of protection claimed in this application.

[0011] Unless otherwise specified, the raw materials, reagents or devices used in the following examples are available from conventional commercial sources or can be obtained by existing known methods.

[0012] The first aspect of this application provides a heterospirocyclic compound.

[0013] Specifically, the structure of the heterospirocyclic compound is shown in formula (1):

[0014] Equation (1) In formula (1), ring A and ring B are independently selected from naphthalene ring or benzene ring; One of X and Y is S, and the other is O or S; X1, X2, and X3 are each independently selected from N or CR5, and at least one of them is N; L1 is selected from any of the structures shown in equations (A-1) to (A-3): ; R1 to R8 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C2-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphinyl or C6-C60 arylamine; a~c and e~g are each independently selected from integers from 0 to 4; d is selected from integers from 0 to 3; Ar1, Ar2, and Ar3 are independently selected from substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C16 cycloalkyl-fused C6-C30 aryl groups, and substituted or unsubstituted C2-C30 heteroaryl groups. The substitutions in Ar1, Ar2, and Ar3 are each independently selected from at least one of deuterium, halogen, cyano, isocyano, phosphin, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C30 substituted or unsubstituted alkyl, and C3-C30 heteroaryl, wherein the number of substitutions ranges from monosubstituted to the maximum number of substitutions. The heteroatoms in the heteroaryl, heteroalkyl, and heterocycloalkyl groups are independently selected from at least one of O, S, N, Se, Si, and Ge.

[0015] In some embodiments, the structure shown in equation (1) is selected from the structures shown in equations (A-4) to (A-8): .

[0016] In some embodiments, the structure shown in equation (1) is selected from the structures shown in equations (A-9) to (A-34):

[0017]

[0018] .

[0019] In some implementations, the structures of X and Y are selected from one of the following: 1) X is O and Y is S; 2) X is S and Y is O; 3) X is S and Y is S.

[0020] In some implementations, a is selected from 0, 1, 2, or 3; and / or b, d, e, and f are independently selected from 0, 1, 2, 3, or 4; and / or c is selected from 0, 1, 2, 3, 4, or 5.

[0021] In some embodiments, Ar1, Ar2, and Ar3 are independently selected from substituted or unsubstituted C6-C20 aryl groups, substituted or unsubstituted C3-C16 cycloalkyl-fused C6-C20 aryl groups, and substituted or unsubstituted C2-C20 heteroaryl groups.

[0022] In some embodiments, Ar1, Ar2, and Ar3 are independently selected from substituted or unsubstituted C6-C12 aryl groups, substituted or unsubstituted C3-C16 cycloalkyl-fused C6-C12 aryl groups, and substituted or unsubstituted C2-C12 heteroaryl groups.

[0023] In some embodiments, Ar1, Ar2, and Ar3 are independently selected from substituted or unsubstituted C6-C12 aryl groups, substituted or unsubstituted C3-C8 cycloalkyl-fused C6-C12 aryl groups, and substituted or unsubstituted C2-C12 heteroaryl groups.

[0024] In some embodiments, the substitution in the substituted or unsubstituted C3-C16 cycloalkyl fused C6-C30 aryl group is located on the aryl or cycloalkyl group.

[0025] In some embodiments, the substitutions in Ar1, Ar2, and Ar3 are each independently selected from at least one of deuterium, halogen, cyano, isocyano, phosphin, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C20 aryl with or without C1-C6 hydrocarbon substituted or unsubstituted C3-C20 heteroaryl, wherein the number of substitutions ranges from monosubstituted to the maximum number of substitutions.

[0026] In some embodiments, the substitutions in Ar1, Ar2, and Ar3 are each independently selected from at least one of deuterium, halogen, cyano, isocyano, phosphin, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C12 aryl, and C3-12 heteroaryl substituted or unsubstituted, wherein the number of substitutions ranges from monosubstituted to the maximum number of substitutions.

[0027] In some embodiments, the substitutions in Ar1, Ar2, and Ar3 are each independently selected from at least one of deuterium, halogen, cyano, isocyano, phosphin, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amino, C1-C6 alkyl-substituted or unsubstituted phenyl, C1-C6 alkyl-substituted or unsubstituted naphthyl, C1-C6 alkyl-substituted or unsubstituted biphenyl, and C1-C6 alkyl-substituted or unsubstituted pyridyl, wherein the number of substitutions ranges from monosubstituted to the maximum number of substitutions.

[0028] In some implementations, X1-X3 contain at least two Ns.

[0029] In some implementations, X1-X3 are all N.

[0030] In some embodiments, R1 to R8 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C30 alkyl, C1-C30 heteroalkyl, C2-C30 alkenyl, C2-C30 alkynyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C36 aryl, C2-C36 heteroaryl, C1-C30 alkoxy, C6-C36 aryloxy, C3-C30 alkylsilyl, C6-C36 arylsilyl, C1-C30 alkylboryl, C6-C36 arylboryl, C6-C36 arylphosphinyl, or C6-C36 arylamine.

[0031] In some embodiments, R1 to R8 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C5-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphinyl, or C6-C30 arylamine.

[0032] In some embodiments, R1 to R8 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C20 aryl, C5-C20 heteroaryl, C1-C10 alkoxy, C6-C20 aryloxy, C3-C10 alkylsilyl, C6-C20 arylsilyl, C1-C10 alkylboryl, C6-C20 arylboryl, C6-C20 arylphosphinyl, or C6-C20 arylamine.

[0033] In some embodiments, R1 to R8 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C6 alkyl, C1-C6 heteroalkyl, C3-C8 cycloalkyl, C3-C8 heterocycloalkyl, C6-C12 aryl or C5-C12 heteroaryl.

[0034] In some embodiments, Ar1, Ar2, and Ar3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyrene, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted fluoranthyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted cyclohexylphenyl, or a combination of at least two of the above.

[0035] In some embodiments, the substitutions in Ar1, Ar2 and Ar3 are independently selected from at least one of deuterium, halogen, cyano, C1-C6 alkyl or C3-C10 cycloalkyl.

[0036] In some embodiments, when Ar1, Ar2, and Ar3 are cycloalkyl-fused aryl groups, the number of substitutions is 0 to 4.

[0037] In some embodiments, Ar1, Ar2, and Ar3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted cyclohexylphenyl, or substituted or unsubstituted pyridyl-substituted phenyl.

[0038] In some implementations, formula (1) contains at least one deuterium atom.

[0039] In some embodiments, the compound has one of the following structural formulas:

[0040]

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[0106]

[0107]

[0108] .

[0109] The second aspect of this application provides for the application of the aforementioned heterospirocyclic compounds.

[0110] Specifically, an organic light-emitting device comprises the aforementioned heterospirocyclic compound.

[0111] In some embodiments, an organic light-emitting device (OLED) includes a cathode and an anode, the cathode being disposed opposite to the anode, and an organic layer being disposed between the cathode and the anode, the organic layer comprising the aforementioned heterospirocyclic compound.

[0112] In some embodiments, the organic layer includes a light-emitting layer containing the heterospirocyclic compound.

[0113] In some embodiments, the organic layer further includes a hole injection layer and a hole transport layer, which are disposed between the anode and the light-emitting layer.

[0114] In some embodiments, the organic layer includes a light-emitting layer, and further includes at least one of a hole-blocking layer, an electron transport layer, and an electron injection layer disposed between the light-emitting layer and the cathode, wherein any one of the hole-blocking layer, electron transport layer, or electron injection layer contains the aforementioned heterospirocyclic compound.

[0115] In some embodiments, the hole blocking layer and / or electron transport layer of the device contain heterocyclic compounds.

[0116] In some embodiments, the heterocyclic compound serves as a hole-blocking layer material in the device.

[0117] In some embodiments, the heterospirocyclic compound is used as one of the electron transport layer materials in the device.

[0118] definition Unless otherwise stated, the scientific and technical terms used herein have the meanings commonly understood by those skilled in the art. However, for a better understanding of this application, definitions of some terms are provided below. In the event that the definitions of terms provided herein differ from the meanings commonly understood by those skilled in the art, the definitions and interpretations provided herein shall prevail.

[0119] In this instruction manual, " "" indicates the connection site with other groups.

[0120] As used herein, the term “and / or” means the presence or use of the listed items, either alone or in combination. In practice, the term means the use or presence of “at least one” or “one or more” of the listed items.

[0121] "Halogen" refers to fluorine, chlorine, bromine, or iodine.

[0122] "alkyl" refers to a straight-chain or branched saturated hydrocarbon group. The number of carbon atoms can be C1-C60, C1-C40, C1-C30, C1-C20, C1-C12, C1-C10, C1-C6, or C1-C4. Non-limiting examples include methyl, ethyl, propyl, butyl, heptyl, and decyl. Each group includes various isomers; for example, butyl includes n-butyl, isobutyl, sec-butyl, and tert-butyl isomers.

[0123] "Cycloalkyl" refers to an alkyl group with a cyclic structure, which can include monocyclic, polycyclic, and spiroalkyl groups. The number of carbon atoms can be C3-C60, C3-C40, C3-C30, C3-C20, C3-C12, C3-C10, or C3-C6. Non-limiting examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl.

[0124] "Alkenyl" refers to a hydrocarbon containing at least one unsaturated carbon-carbon double bond. The number of carbon atoms can be C2-C40, C2-C30, C2-C20, C2-C12, C2-C10, C2-C6, or C2-C4. Non-limiting examples include: vinyl, propenyl, allyl, butadienyl, hextrienyl, etc.

[0125] "Alynyl" refers to a hydrocarbon containing at least one unsaturated carbon-carbon triple bond. The number of carbon atoms can be C2-C40, C2-C30, C2-C20, C2-C12, C2-C10, C2-C6, or C2-C4. Non-limiting examples include ethynyl and propynyl.

[0126] "Heteroalkyl" refers to an alkyl group in which at least one carbon atom is replaced by a non-carbon atom, excluding cases where the carbon atom serving as a linking site is replaced by a non-carbon atom (e.g., alkoxy, alkylsilyl). The number of carbon atoms can be C1-C40, C1-C30, C1-C20, C1-C12, C1-C10, C1-C6, or C1-C4. Examples include mercaptomethylmethane, methoxymethane, ethoxymethane, tert-butoxymethane, and N,N-dimethylmethane.

[0127] "Heterocyclic alkyl" refers to a cycloalkyl group in which at least one carbon atom of the ring is replaced by a non-carbon atom, which can be selected from at least one of O, S, N, P, B, Si, Ge, or Se. The number of carbon atoms in the ring can be C3-C40, C3-C30, C3-C20, C3-C12, C3-C10, or C3-C6. Non-limiting examples include epoxide butyl, epoxide pentyl, and epoxide hexyl.

[0128] "Aryl" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. It can be a monocyclic aryl or polycyclic aryl. At least one ring in a polycyclic aryl is an aromatic ring system. Multiple rings in a polycyclic aryl can be connected to each other via single bonds or can be fused together, for example, phenyl fusion with phenyl to form naphthyl, or phenyl fusion with phenyl to form diphenyl via single bonds. The number of carbon atoms can be C6-C60, C6-C30, C6-C20, C6-C12, or C6-C10. Non-limiting examples include phenyl, naphthyl, anthracene, phenanthrene, tetraphenyl, pyrene, dinaphthylphenyl, acenaphthyl, benzo[g]pyrene, benzo[g]phenanthrene, benzo[g]triylyl, fluorene, spirodifluorene, 2-phenylnaphthyl, benzo[g]fluorene, dibenzo[g]fluorene, diphenyl, triphenyl, tetraphenyl, and fluoranthyl, etc. Benzophenanthrene groups include 1,2-benzophenanthrene, 3,4-benzophenanthrene, 9,10-benzophenanthrene, etc.

[0129] "Heteroaryl" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom. It can be a monocyclic or polycyclic heteroaryl group. In a polycyclic heteroaryl group, multiple rings can be linked together by single bonds or fused together, with at least one carbon atom on at least one ring being replaced by a non-carbon atom. For example, a phenyl group fused with a carbazole group forms a benzocarbazole group, or a phenyl group linked with a carbazole group by a single bond forms a phenyl-substituted carbazole group or a carbazole-substituted phenyl group. The non-carbon atom can be a monovalent group selected from heterocyclic aromatic systems of O, S, N, Se, Si, or Ge, but does not include cases where the aryl group uses a non-carbon atom as a linking site (e.g., aryloxy, arylsilyl, arylamino). The number of carbon atoms can be C3-C30, C3-C20, C3-C12, C3-C10, or C3-C6. Non-limiting examples include: pyrrolo, pyrrolopyrrolo, furanopyrrolo, thienopyrrolo, pyridyl, pyrazolyl, pyrimidinyl, pyrazinyl, triazinyl, pyridazinyl, phenazinyl, phenothiazinyl, phenoxazinyl, indoleyl, isoindoleyl, indoleazolyl, imidazolyl, benzimidazolyl, triazolyl, tetrazolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, furanofuranyl, azadibenzofuranyl, thienofuranyl, diazadibenzofuranyl, benzo[B]naphtho[1,2] -D] furanyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, quinazolinoneyl, carbazoyl, azacarbazoyl, diazacarbazoyl, phenanthrynyl, primidyl, acridineyl, dihydroacridyl, phenanthrynyl, oxazolinyl, oxazolyl, oxadiazolyl, benzoisooxazolyl, thiazoyl, benzothiazoyl, benzoisothiazoyl, pyrroloimidazoyl, furazolyl, thienyl, benzothiaphenyl, dibenzothiaphenyl, azadibenzothiaphenyl, diazadibenzothiaphenyl, thienothiaphenyl and o-diazanaphthyl, etc.

[0130] "Cycloalkyl-fused aryl" refers to a polycyclic structure formed by the fusion of an aryl group and a cycloalkyl group (i.e., sharing two adjacent carbon atoms). The definitions of "aryl" and "cycloalkyl" are as described above. The substitution position of the fused cycloalkyl aryl group can occur in either the cycloalkyl or aryl moiety. Substitution can be deuteration, alkyl substitution, etc., such as 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene.

[0131] The terms "alkoxy" and "aryloxy" refer to groups having a "-O-alkyl" or "-O-aryl" structure, respectively, meaning that the alkyl or aryl group as defined above is connected to the parent nucleus via an oxygen atom. Examples of "alkoxy" include: methoxy, ethoxy, and tert-butoxy (-OC(CH3)3 or... Examples of aryl groups include phenoxy, naphthoxy, or biphenyloxy.

[0132] "Aryl group" refers to an alkyl group substituted with an aryl group, where the definitions of "aryl" and "alkyl" are as described above. The number of carbon atoms in an aryl group can be C7-C30, C7-C20, C7-C12, or C7-C10. Non-limiting examples include benzyl, phenethyl, phenylpropyl, tolylmethyl, and p-tolylmethyl, etc.

[0133] In “alkylsilyl” or “arylsilyl”, the number of alkyl or aryl groups can be 1 to 3; in the terms “alkylboryl”, “alkylamine”, “arylboryl”, “arylphosphine”, and “arylamine”, the number of alkyl or aryl groups can be 1 or 2; the defined carbon number refers to the total number of carbons in the group.

[0134] In expressions such as "the R group of substituted or unsubstituted Ca-Cb", "Ca-Cb" refers to the number of carbon atoms a to b when the R group is unsubstituted, excluding the number of carbon atoms in the substituents when the R group is substituted.

[0135] "Substitution" in "substituted or unsubstituted" means that one or more hydrogen atoms are replaced by other atoms or groups, and unless otherwise defined, it also includes the replacement of one or more hydrogen atoms by groups formed by the connection of two or more of the substituents described above.

[0136] "Maximum number of substitutions" refers to the maximum number of hydrogen atoms contained in the group when there are no substituents other than hydrogen.

[0137] "At least two combinations" means that at least two defined groups are connected by a single bond or fused together. For example, phenyl groups fused together to form a naphthyl group, or phenyl groups connected by a single bond to form a diphenyl group. It should be understood that the combination of groups is contingent upon satisfying the defined range of carbon numbers.

[0138] The following embodiments are merely for the purpose of understanding the technical invention and should not be regarded as specific limitations of this application.

[0139] The raw materials and solvents used in the synthesis of the compounds in this application were all purchased from suppliers well-known to those skilled in the art, such as Alfa and Acros.

[0140] Example: Synthesis of Heterospirocyclic Compounds Synthesis of compound A3

[0141] Synthesis of compound A3-3 Compound A3-1 (15.00 g, 35.49 mmol, CAS: 1073062-42-6), compound A3-2 (7.03 g, 35.49 mmol, CAS: 4688-76-0), tetra(triphenylphosphine)palladium (0.41 g, 0.35 mmol), potassium carbonate (12.26 g, 88.71 mmol), toluene (250 ml), ethanol (50 ml), and deionized water (50 ml) were added to a 500 ml three-necked round-bottom flask. The flask was purged with nitrogen three times. The system was then heated to 90 °C and reacted for 4 hours. The reaction was monitored by TLC (using dichloromethane:n-hexane = 1:5 as the developing solvent). Compound A3-1 was completely consumed.

[0142] After the reaction was complete, the mixture was cooled to room temperature, and extracted with dichloromethane (100 ml * 3) and deionized water (50 ml). The organic phase was then evaporated to dryness (60 °C) to obtain a pale yellow solid. The solid was then dry-coated onto a silica gel column (200-300 mesh silica gel, dichloromethane:n-hexane = 1:5 as eluent) for purification. After elution, the solid was concentrated under reduced pressure at 60 °C for 1 hour to obtain a white solid, compound A3-3 (12.56 g, purity: 99.53%, yield: 71.36%), mass spectrometry: 496.15 (M+H).

[0143] Synthesis of compound A3-6 Compound A3-4 (15.00 g, 52.90 mmol, CAS: 947188-01-4) and dry tetrahydrofuran (200 ml) were added to a 500 ml three-necked round-bottom flask. The flask was purged with nitrogen three times. The system was then cooled to -78 °C. A solution of n-butyllithium in n-hexane (27.51 ml, 68.77 mmol, concentration 2.5 mol / L) was then added dropwise, keeping the internal temperature below -70 °C. The addition was completed over 20 minutes, and the mixture was stirred at -78 °C for 0.5 hours. Finally, compound A3-5 (15.72 g, 74.06 mmol, CAS: 492-22-8) was slowly added dropwise over 10 minutes, and the mixture was stirred continuously at -78 °C. Stirred at 78℃ for 1.5 hours, monitored by TLC (dichloromethane:n-hexane = 1:5 as the developing solvent), compound A3-4 was completely consumed.

[0144] The reaction was quenched dropwise with deionized water (100 ml), and after reaching room temperature, the mixture was directly separated. The aqueous phase was extracted twice with ethyl acetate (100 ml * 2). The organic phases were combined and concentrated under reduced pressure at 65°C for 1 hour to obtain a light yellow solid. The solid was then dry-loaded onto a silica gel column for purification by silica gel column chromatography (200 μL / min). Using 300-mesh silica gel and dichloromethane:n-hexane = 1:5 as eluent, the solution was concentrated under reduced pressure at 65°C to obtain a white solid, compound A3-6 (16.53 g, purity: 99.39%, yield: 74.95%), mass spectrometry: 417.06 (M+H).

[0145] Synthesis of compound A3-7 Compound A3-6 (16.00 g, 38.38 mmol), concentrated hydrochloric acid (2.4 ml, 76.75 mmol), and acetic acid (200 ml) were added to a 500 ml three-necked round-bottom flask. The system was then cooled to 70 °C and reacted for 1 h. The reaction was monitored by TLC (using dichloromethane:n-hexane = 1:5 as the developing solvent). Compound A3-6 was completely consumed.

[0146] Add methanol (100 ml) to the system, a large amount of solid precipitates, filter, and dry-load the sample onto a silica gel column for silica gel column chromatography purification (200 ml). Using 300-mesh silica gel and dichloromethane:n-hexane = 1:5 as eluent, the mixture was concentrated under reduced pressure at 65°C to obtain a white solid compound A3-7 (9.97 g, purity: 99.56%, yield: 65.13%), mass spectrometry: 399.05 (M+H).

[0147] Synthesis of compound A3-9 Compound A3-7 (9.90 g, 24.82 mmol), compound A3-8 (6.43 g, 25.31 mmol), tris(dibenzylacetone)dipalladium (0.23 g, 0.25 mmol), 2-dicyclohexylphosphine-2′,4′,6′-triisopropylbiphenyl (0.24 g, 0.50 mmol), potassium acetate (6.09 g, 62.05 mmol), and 1,4-dioxane (300 ml) were added to a 500 ml three-necked round-bottom flask. The flask was purged with nitrogen three times, and then the system was heated to 100 °C and reacted for 2 hours. The reaction was monitored by TLC (ethyl acetate:n-hexane = 1:5 as the developing solvent). Compound A3-7 was completely consumed.

[0148] Cool to 60℃, concentrate under reduced pressure to remove solvent, add dichloromethane (150ml), wash three times with deionized water (50ml*3), separate the liquid, dry-load the sample onto a silica gel column using silica gel column chromatography (200-300 mesh silica gel, ethyl acetate:n-hexane = 1:10 as eluent). After elution, concentrate under reduced pressure at 60℃ for 1 hour to obtain a white solid, compound A3-9 (9.23g, purity: 99.26%, yield: 75.83%), mass spectrometry: 491.18 (M+H).

[0149] Synthesis of compound A3 Following the synthesis and purification method of compound A3-3, only the corresponding raw materials need to be changed to obtain the target compound A3 (10.73 g, purity: 99.95%, yield: 70.96%). After sublimation purification of 10.73 g of crude compound A3, sublimed pure compound A3 (8.96 g, purity: 99.95%, yield: 83.50%) was obtained, mass spectrometry: 824.27 (M+H).

[0150] 1 H NMR (400 MHz, CDCl3) δ 8.66 (t, J = 2.2 Hz, 1H), 8.43 – 8.36 (m,5H), 7.96 (t, J = 2.1 Hz, 1H), 7.60 – 7.44 (m, 16H), 7.43 – 7.31 (m, 8H),7.18 – 7.14 (m, 3H), 7.10 – 6.98 (m, 3H). Synthesis of intermediate A15-5

[0151] Synthesis of compound A15-3 Following the synthesis and purification method of compound A3-3, only the corresponding raw materials need to be changed to obtain the target compound A15-3 (15.83 g, purity: 99.30%, yield: 72.58%), mass spectrometry: 214.03 (M+H). The CAS number for A15-1 is 150255-96-2.

[0152] Synthesis of compound A15-4 Following the synthesis and purification method of compound A3-9, only the corresponding raw materials need to be changed to obtain the target compound A15-4 (16.52g, purity: 99.16%, yield: 74.62%), mass spectrometry: 306.16 (M+H).

[0153] Synthesis of compound A15-5 Following the synthesis and purification method of compound A3-3, only the corresponding raw materials need to be changed to obtain the target compound A15-5 (13.06g, purity: 99.61%, yield: 70.64%), mass spectrometry: 521.15 (M+H).

[0154] Synthesis of intermediate A32-4

[0155] Synthesis of intermediate A32-2 Compound A32-1 (15.00 g, 43.65 mmol, CAS: 2817665-98-6), compound A3-8 (11.31 g, 44.52 mmol), [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (0.32 g, 0.44 mmol), potassium acetate (10.71 g, 109.12 mmol), and 1,4-dioxane (300 ml) were added to a 500 ml three-necked round-bottom flask. The flask was purged with nitrogen three times, and then the system was heated to 100 °C and reacted for 2 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). Compound A32-1 was completely consumed.

[0156] The solution was cooled to 60°C, concentrated under reduced pressure to remove the solvent, and ethyl acetate (200 ml) was added. The solution was washed three times with deionized water (50 ml * 3), extracted, and separated. The solution was then loaded onto a silica gel column using a dry chromatography method and purified by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate: n-hexane = 1:20 as eluent). After elution, the solution was concentrated under reduced pressure at 60°C for 1 hour to obtain a white solid, which was compound A32-2 (12.67 g, purity: 99.23%, yield: 74.29%), mass spectrometry: 391.16 (M+H).

[0157] Synthesis of intermediate A32-4 Compound A32-2 (12.00 g, 30.71 mmol), compound A32-3 (8.22 g, 30.71 mmol, CAS: 3842-55-5), tetra(triphenylphosphine)palladium (0.35 g, 0.31 mmol), sodium hydroxide (3.07 g, 76.78 mmol), tetrahydrofuran (250 ml), and water (50 ml) were added to a 500 ml three-necked round-bottom flask. The flask was purged with nitrogen three times, and then the system was heated to 75 °C and reacted for 8 hours. The reaction was monitored by TLC (using dichloromethane:n-hexane = 1:5 as the developing solvent). Compound A32-3 was completely consumed.

[0158] Cool to 60℃, concentrate under reduced pressure to remove solvent, add dichloromethane (200ml), wash three times with deionized water (50ml*3), extract and separate, dry-load onto silica gel column for silica gel column chromatography purification (200-300 mesh silica gel, dichloromethane:n-hexane = 1:5 as eluent). After elution, concentrate under reduced pressure at 60℃ for 1 hour to obtain a white solid as compound A32-4 (10.88g, purity: 99.60%, yield: 71.42%), mass spectrometry: 496.15 (M+H).

[0159] Synthesis of intermediate A41-5

[0160]

[0161] Synthesis of intermediate A41-3 Compound A41-1 (15.00 g, 47.27 mmol, CAS: 535934-25-9), compound A41-2 (12.96 g, 47.27 mmol, CAS: 1310405-29-8), tetra(triphenylphosphine)palladium (0.55 g, 0.47 mmol), potassium carbonate (16.33 g, 118.17 mmol), tetrahydrofuran (300 ml), and water (50 ml) were added to a 500 ml three-necked round-bottom flask. The mixture was purged with nitrogen three times, and then the system was heated to 50 °C and reacted for 6 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). Compound A41-1 was completely consumed.

[0162] Cool to 60℃, concentrate under reduced pressure to remove solvent, add ethyl acetate (200ml), wash three times with deionized water (50ml*3), separate the contents, dry-pick up the sample onto a silica gel column using silica gel column chromatography (200-300 mesh silica gel, ethyl acetate:n-hexane = 1:20 as eluent). After elution, concentrate under reduced pressure at 60℃ for 1 hour to obtain a white solid, compound A41-3 (14.36g, purity: 99.20%, yield: 72.38%), mass spectrometry: 419.01 (M+H).

[0163] Synthesis of intermediate A41-4 Following the synthesis and purification method of compound A32-2, only the corresponding raw materials need to be changed to obtain the target compound A41-4 (11.50 g, purity: 99.12%, yield: 73.86%), mass spectrometry: 467.19 (M+H).

[0164] Synthesis of intermediate A41-5 Following the synthesis and purification method of compound A32-4, only the corresponding raw materials need to be changed to obtain the target compound A41-5 (9.85g, purity: 99.63%, yield: 73.06%), mass spectrometry: 572.18 (M+H).

[0165] Synthesis of intermediate A59-3

[0166] Synthesis of intermediate A59-3 Following the synthesis and purification method of compound A32-4, only the corresponding raw materials need to be changed to obtain the target compound A59-3 (11.72 g, purity: 99.34%, yield: 70.63%), mass spectrometry: 572.18 (M+H). The CAS of A59-1 is 2607747-86-2, and the CAS of A59-2 is 1472062-94-4.

[0167] Synthesis of intermediate A81-4

[0168] Synthesis of intermediate A81-4 Following the synthesis and purification methods of compounds A32-2 and A32-4, only the corresponding raw materials need to be changed to obtain the target compound A81-4 (12.95 g, purity: 99.65%, yield: 74.61%), mass spectrometry: 495.15 (M+H). The CAS numbers for A81-1 and A81-3 are 2791439-58-0 and 2915-16-4 respectively.

[0169] Synthesis of intermediate A119-6

[0170] Synthesis of intermediate A119-6 Following the synthesis and purification methods of compounds A41-3, A41-4, and A41-5, only the corresponding raw materials need to be changed to obtain the target compound A119-6 (9.73 g, purity: 99.49%, yield: 69.86%), mass spectrometry: 596.18 (M+H). The CAS numbers for A119-1, A119-2, and A119-5 are: 774608-49-0, 500904-93-8, and 1472062-95-5, respectively.

[0171] Synthesis of intermediate A139-1

[0172] Synthesis of intermediate A139-1 Following the synthesis and purification method of compound A3-3, only the corresponding raw materials need to be changed to obtain the target compound A139-1 (13.64 g, purity: 99.50%, yield: 74.15%), mass spectrometry: 572.18 (M+H).

[0173] Synthesis of intermediate A159-2

[0174] Synthesis of intermediate A159-2 Following the synthesis and purification method of compound A32-4, only the corresponding raw materials need to be changed to obtain the target compound A159-2 (12.82 g, purity: 99.44%, yield: 70.30%), mass spectrometry: 612.21 (M+H). The CAS number for A159-1 is 1618106-98-1.

[0175] Synthesis of intermediate A177-6

[0176] Synthesis of intermediate A177-6 Following the synthesis and purification methods of compounds A41-3, A41-4, and A41-5, only the corresponding raw materials need to be changed to obtain the target compound A177-6 (11.20 g, purity: 99.23%, yield: 68.34%), mass spectrometry: 496.15 (M+H). The CAS numbers for A177-1, A177-2, and A177-5 are 31928-44-6, 1408000-96-3, and 29509-91-9, respectively.

[0177] Synthesis of intermediate A205-4 ; Synthesis of intermediate A205-2 Following the synthesis and purification methods of compounds A41-3, A41-4, and A41-5, only the corresponding raw materials need to be changed to obtain the target compound A205-4 (13.66 g, purity: 99.37%, yield: 74.22%), mass spectrometry: 521.15 (M+H). The CAS number for A205-1 is 148836-41-3.

[0178] Synthesis of intermediate A306-4 ; Synthesis of intermediate A306-4 Following the synthesis and purification methods of compounds A41-3, A41-4, and A41-5, only the corresponding raw materials need to be changed to obtain the target compound A306-4 (10.54 g, purity: 99.63%, yield: 70.19%), mass spectrometry: 509.17 (M+H). The CAS number for A306-1 is 1228456-15-2.

[0179] Synthesis of intermediate A336-4 ; Synthesis of intermediate A336-4 Following the synthesis and purification methods of compounds A41-3, A41-4, and A41-5, only the corresponding raw materials need to be changed to obtain the target compound A336-4 (12.10 g, purity: 99.43%, yield: 71.81%), mass spectrometry: 501.18 (M+H). The CAS number for A336-1 is 1898284-38-2.

[0180] Synthesis of intermediate A348-3

[0181] Synthesis of intermediate A348-3 Compound A348-1 (15.00 g, 67.24 mmol, CAS: 771-15-3), compound A348-2 (26.34 g, 201.73 mmol), cesium carbonate (43.82 g, 134.49 mmol), and N-methylpyrrolidone (350 ml) were added to a 500 ml three-necked round-bottom flask. The mixture was purged with nitrogen three times, and then the system was heated to 140 °C and reacted for 24 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:20 as the developing solvent). Compound A3-1 was completely consumed.

[0182] After the reaction was complete, the mixture was cooled to room temperature, and extracted with ethyl acetate (100 ml * 3) and deionized water (50 ml). The organic phase was then evaporated to dryness (60 °C). The sample was mixed with silica gel and dry-coated onto a column for silica gel column chromatography purification (200-300 mesh silica gel, ethyl acetate:n-hexane = 1:30 as eluent). After elution, the mixture was concentrated under reduced pressure at 60 °C for 1 hour to obtain a white solid, compound A348-3 (16.32 g, purity: 99.06%, yield: 72.75%), mass spectrometry: 332.96 (M+H).

[0183] Synthesis of intermediate A364-3

[0184] Synthesis of intermediate A364-2 Following the synthesis and purification methods of compounds A41-3, A41-4, and A41-5, only the corresponding raw materials need to be changed to obtain the target compound A336-4 (10.53 g, purity: 99.30%, yield: 71.81%), mass spectrometry: 546.17 (M+H). Among them, A364-1... CAS:500904-93-8.

[0185] Combining the above intermediates, compounds A15, A32, A41, A59, A81, A119, A128, A139, A159, A177, A205, A243, A306, A336, A348, and A364 were prepared using a similar synthetic method to compound A3, the difference being the different raw materials used, as shown in Table 1 below.

[0186] Table 1

[0187] Application example: Fabrication of organic light-emitting devices The spirocyclic compound obtained in the above embodiments is applied to an organic light-emitting device (OLED). The OLED comprises a glass substrate, an anode, a hole injection layer, a first hole transport layer (HTL1), a second hole transport layer (HTL2), a light-emitting layer, a hole blocking layer (HBL), an electron transport layer (ETL), and a cathode, all stacked together. Specifically, the fabrication method of this OLED is as follows: A glass substrate with an ITO transparent electrode (anode) on its surface is taken, wherein the anode thickness is 100 nm. The glass substrate is ultrasonically cleaned in ethanol for 10 minutes, then dried at 150°C, and then treated with N2Plasma for 30 minutes. Compound HATCN is deposited on the surface of the anode side to form a hole injection layer, wherein the hole injection layer thickness is 5 nm. Compound HTM1 is deposited on the surface of the hole injection layer side to form a first hole transport layer, wherein the first hole transport layer thickness is 60 nm. Compound HTM2 is deposited on the surface of the first hole transport layer side to form a second hole transport layer, wherein the second hole transport layer thickness is 10 nm. A host material and a guest material are co-deposited on the surface of the second hole transport layer side to form a light-emitting layer. The weight ratio of the guest material is 97%:3%; the thickness of the luminescent layer is 25 nm; HBL material is vapor-deposited on one side of the luminescent layer to form a hole blocking layer, wherein the hole blocking layer has a thickness of 5 nm; the HBL material is the spirocyclic compound of this application or the comparative compound, and the specific materials are shown in Table 2; an electron transport material is vapor-deposited on one side of the hole blocking layer to form an electron transport layer, wherein the thickness of the electron transport layer is 350 nm, the electron transport material is compound ETL or a mixture of the spirocyclic compound of this application (or the comparative compound) and LiQ, wherein the weight ratio of the two in the mixture is 1:1, and the specific material combination is shown in Table 2; metals Mg and Ag are co-deposited on one side of the electron transport layer to form a cathode composed of magnesium-silver alloy material, wherein the cathode has a thickness of 100 nm, and the weight ratio of Mg to Ag is 1:9.

[0188] The structural formulas of HAT-CN, HTL, EBL, host material (BH), guest material (BD), ETL, LiQ, and comparative compounds 1-4 are as follows: .

[0189] evaluate: The above-mentioned organic light-emitting devices were subjected to device performance testing. The spirocyclic compound prepared in this application and comparative compounds 1-4 were used as hole-blocking layer materials and electron transport layer materials, respectively, for comparison. A constant current power supply (Keithley 2400) was used, and a fixed current density was applied to the light-emitting element. The emission spectrum was measured using a spectroradiometer (CS2000). Simultaneously, at 10 mA / cm²... 2 The IVL (current-voltage-luminance) performance of the devices was measured, and the lifetime of the LT95 devices was tested at 1000 nits. The results are shown in Table 2 below (the examples in Table 2 use at least one layer of the heterospirocyclic compound of this application, and the comparative examples use comparative compounds).

[0190] Table 2

[0191] The compounds in this application employ a non-planar rigid spiroring core structure, exhibiting high electron mobility, which is beneficial for electron-hole transport balance. Furthermore, through specific linkage methods of the connecting groups, energy levels can be fine-tuned, resulting in a lower electron injection energy barrier and improved device performance. As shown in the data comparison in the table above, using the compounds in this application as hole blocking layer materials and electron transport layer materials in organic light-emitting devices demonstrates superior performance compared to comparative compounds 1-4 in terms of driving voltage, luminous efficiency, and device lifetime.

[0192] The above results indicate that the compounds of this application possess advantages such as good optical, electrical, and thermal stability, high luminous efficiency, low voltage, and long lifetime, making them suitable for use in organic light-emitting devices. In particular, they have the potential to be applied in the AMOLED industry as hole-blocking layer materials and electron transport layer materials.

[0193] Furthermore, since it is impossible to exhaustively list all the compounds in this application, Table 2 above only lists the performance of some compounds or devices in this application. However, within the scope of protection claimed in this application, especially the compounds with the specific structural formulas given in this invention, all have advantages similar to compound A3, such as high optical, electrical, and thermal stability, low sublimation temperature, low driving voltage, high luminous efficiency, and long device life.

Claims

1. A heterospirocyclic compound, characterized in that: The structure of the heterospirocyclic compound is shown in formula (1): Equation (1) In formula (1), ring A and ring B are independently selected from naphthalene ring or benzene ring; One of X and Y is S, and the other is O or S; X1, X2, and X3 are each independently selected from N or CR5, and at least one of them is N; L1 is selected from any of the structures shown in equations (A-1) to (A-3): ； R1 to R8 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C2-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphinyl or C6-C60 arylamine; a~c and e~g are each independently selected from integers from 0 to 4; d is selected from integers from 0 to 3; Ar1, Ar2, and Ar3 are independently selected from substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C16 cycloalkyl-fused C6-C30 aryl groups, and substituted or unsubstituted C2-C30 heteroaryl groups. The substitutions in Ar1, Ar2, and Ar3 are each independently selected from at least one of deuterium, halogen, cyano, isocyano, phosphin, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C30 substituted or unsubstituted alkyl, and C3-C30 heteroaryl, wherein the number of substitutions ranges from monosubstituted to the maximum number of substitutions. The heteroatoms in the heteroaryl, heteroalkyl, and heterocycloalkyl groups are independently selected from at least one of O, S, N, Se, Si, and Ge.

2. The heterospirocyclic compound according to claim 1, characterized in that: The structure shown in equation (1) is selected from the structures shown in equations (A-4) to (A-8): 。 3. The heterospirocyclic compound according to claim 1, characterized in that: The structure shown in equation (1) is selected from the structures shown in equations (A-9) to (A-34): 。 4. The heterospirocyclic compound according to any one of claims 1 to 3, characterized in that: The structures of X and Y are selected from one of the following: 1) X is O, Y is S; 2) X is S, Y is O; 3) X is S, Y is S; and / or, R1 to R8 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C30 alkyl, C1-C30 heteroalkyl, C2-C30 alkenyl, C2-C30 alkynyl, C3-C30 heterocycloalkyl, C6-C36 aryl, C2-C36 heteroaryl, C1-C30 alkoxy, C6-C36 aryloxy, C3-C30 alkylsilyl, C6-C36 arylsilyl, C1-C30 alkylboron, C6-C36 arylboron, C6-C36 arylphosphine, or C6-C36 arylamine.

5. The heterospirocyclic compound according to any one of claims 1 to 3, characterized in that: X1-X3 contains at least two N; And / or, R1 to R8 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C6 alkyl, C1-C6 heteroalkyl, C3-C8 cycloalkyl, C3-C8 heterocycloalkyl, C6-C12 aryl or C5-C12 heteroaryl.

6. The heterospirocyclic compound according to any one of claims 1 to 3, characterized in that: X1-X3 are all N; and / or, Ar1, Ar2, and Ar3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted... Or unsubstituted spirodifluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrene, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted fluoranthyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazole, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted cyclohexylphenyl, or a combination of at least two of the above.

7. The heterospirocyclic compound according to any one of claims 1 to 3, characterized in that: Ar1, Ar2 and Ar3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted cyclohexylphenyl or substituted or unsubstituted pyridyl-substituted phenyl; the substituted in Ar1, Ar2 and Ar3 are independently selected from at least one of deuterium, halogen, cyano, C1-C6 alkyl or C3-C10 cycloalkyl; and / or, formula (1) contains at least one deuterium atom.

8. The heterospirocyclic compound according to any one of claims 1 to 3, characterized in that: The compound has one of the following structural formulas: 。 9. An organic light-emitting device, characterized in that: It includes a cathode and an anode, the cathode being disposed opposite to the anode, and an organic layer being disposed between the cathode and the anode, the organic layer comprising a heterospirocyclic compound as described in any one of claims 1 to 8.

10. The organic light-emitting device according to claim 9, characterized in that: The organic layer includes a light-emitting layer containing the heterospirocyclic compound; or, the organic layer includes a light-emitting layer and further includes a hole-blocking layer or an electron transport layer disposed between the light-emitting layer and the cathode, the hole-blocking layer or electron transport layer containing the heterospirocyclic compound.

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