Heterocyclic compound and organic electroluminescent device thereof

Abstract

This invention provides a heterocyclic compound and its organic electroluminescent device, specifically relating to the field of organic electroluminescent materials technology. To address the problem of shortened device lifetime caused by the recombination of some holes with electrons after penetrating the light-emitting layer, this invention provides a heterocyclic compound with good electron mobility and excellent electron transport capability. When used as an electron transport layer or hole blocking layer, it can improve the recombination rate of charge carriers in the light-emitting layer. Furthermore, when used as the host material, it can improve the luminous efficiency of the device, thereby extending its lifespan.

Description

Technical Field

[0001] This invention provides a heterocyclic compound and its organic electroluminescent device, specifically relating to the field of organic electroluminescent materials technology. Background Technology

[0002] Research on Organic Light-Emitting Diodes (OLEDs) began in the 1960s, with Pope et al. first reporting the electroluminescence phenomenon in crystals. In the 1980s, Qingyun Deng et al. fabricated high-efficiency fluorescent OLEDs with multilayer structures, inspiring numerous scholars to dedicate themselves to the research of organic electroluminescence. Compared to liquid crystal displays (LCDs), OLEDs, as self-emissive devices, possess many superior characteristics such as wide viewing angle, excellent contrast, low voltage, fast response, high efficiency, and long lifespan. Therefore, they are widely used in lighting and display fields and have broad development prospects.

[0003] In OLEDs, holes from the anode and electrons from the cathode are injected into the light-emitting layer by applying a voltage. The recombination of these holes and electrons generates high-energy excitons. These excitons activate the luminescent material in the light-emitting layer, causing electrons in the luminescent material molecules to transition from the ground state to an excited state. Since electrons in the excited state are extremely unstable, they return to the stable ground state. During this transition, energy is released in the form of light, thus enabling the device to emit light.

[0004] OLEDs typically employ a sandwich structure, with organic functional layers sandwiched between the anode and cathode. This structure is usually multi-layered, including, in addition to the emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, another electron transport layer, an electron injection layer, and a capping layer. To improve the device's luminous efficiency, effective recombination of holes and electrons is crucial. Because the hole mobility of the hole transport layer material is two orders of magnitude higher than that of the electron transport material, an effective balance between hole and electron transport cannot be achieved. This allows some holes to easily pass through the emitting layer and recombine with electrons at the interface between the emitting and electron transport layers or within the electron transport layer itself, leading to a decrease in the device's luminous efficiency. Therefore, developing functional materials with electron transport properties to improve device performance remains a key research focus.

[0005] Furthermore, organic electroluminescent materials have been successfully developed in red, green, and blue color systems, achieving full color gamut display. However, given that the choice of host material has a significant impact on the efficiency and lifespan of the device, further research is still necessary. Summary of the Invention

[0006] To effectively improve the electron migration efficiency of devices and address the problem of shortened device lifetime caused by the recombination of some holes with electrons after penetrating the light-emitting layer, this invention provides a heterocyclic compound and its organic electroluminescent device. When applied to an electron transport layer or hole blocking layer, it can effectively transport electrons and increase the recombination probability of charge carriers in the light-emitting layer. Alternatively, it can be used as the main material of the light-emitting layer to improve the luminous efficiency of the device and extend its lifespan.

[0007] This invention provides a heterocyclic compound, which is represented by Formula 1:

[0008]

[0009] In Equation 1,

[0010] A is selected from formula 2 or formula 3, and -* represents the connection site;

[0011] R1 and R2 are independently selected from any one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C2-C20 heteroaryl groups, or any one of R1 and R2 can be directly bonded to L.

[0012] The R3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C20 heteroaryl, wherein m is selected from 0, 1, 2 or 3;

[0013] The R4 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C20 heteroaryl, wherein n is independently selected from 0, 1 or 2.

[0014] The L, L1, and L2 are independently selected from any one of single-bonded, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C2-C20 heteroarylene.

[0015] The W is selected from a single bond or O, S;

[0016] The X is independently selected from N or CR5;

[0017] The Y is independently selected from O, S, or C(R6)2;

[0018] The Z is independently selected from N or CR8;

[0019] The R5, R6, and R8 are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2-C20 heteroaryl, wherein two adjacent R5s may be connected to form a substituted or unsubstituted ring, and two adjacent R8s may be connected to form a substituted or unsubstituted ring.

[0020] In addition, the present invention also provides an organic electroluminescent device comprising an anode, a cathode and an organic layer, wherein the organic layer is located between the anode and the cathode, and the organic layer comprises a heterocyclic compound having Formula 1.

[0021] Beneficial effects

[0022] The heterocyclic compounds described in this invention possess a rigid structure, resulting in a high glass transition temperature. Furthermore, these compounds exhibit excellent electron mobility and a superior ability to balance carrier transport, thereby reducing the driving voltage of organic electroluminescent devices. Simultaneously, the heterocyclic compounds effectively block the diffusion of holes into the electron transport layer, thereby increasing the recombination rate of carriers in the emissive layer. When used as the main body of the emissive layer, they can improve the luminous efficiency of the device and extend its lifetime. Detailed Implementation

[0023] The present invention will be further illustrated below with reference to specific embodiments. It should be understood that the embodiments described are for illustrative purposes only and are not intended to limit the scope of the invention. After reading this invention, other embodiments obtained by those skilled in the art without inventive effort all fall within the scope of protection claimed in this application.

[0024] The "-*" on the group described in this invention represents a linking site.

[0025] The "halogens" mentioned in this invention include fluorine, chlorine, bromine, and iodine.

[0026] In this invention, "C1-C6" in "substituted or unsubstituted C1-C6 alkyl" refers to the number of carbon atoms in the unsubstituted "alkyl", excluding the number of carbon atoms in the substituents. "C3-C10" in "substituted or unsubstituted C3-C10 cycloalkyl" refers to the number of carbon atoms in the unsubstituted "cycloalkyl", excluding the number of carbon atoms in the substituents. "C6-C30" in "substituted or unsubstituted C6-C30 aryl" refers to the number of carbon atoms in the unsubstituted "aryl", excluding the number of carbon atoms in the substituents. "C2-C20" in "substituted or unsubstituted C2-C20 heteroaryl" refers to the number of carbon atoms in the "heteroaryl", excluding the number of carbon atoms in the substituents.

[0027] The "substituted or unsubstituted silyl group" mentioned in this invention refers to —Si(R k )3 groups, wherein each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings. Preferably, each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15, even more preferably 1 to 10, and most preferably 1 to 8. The cycloalkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 15, even more preferably 3 to 10, and most preferably 3 to 7. The aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 13, even more preferably 6 to 12, and most preferably 6 to 10. Preferably, each R... k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Preferred substituted silyl groups specifically include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc.

[0028] The alkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an alkane molecule. It can be straight-chain or branched, and the chain alkyl groups with more than three carbon atoms in this invention include their isomers. Preferably, it has 1 to 12 carbon atoms, more preferably 1 to 6 carbon atoms. Specific examples may include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, pentyl, and hexyl.

[0029] The cycloalkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from a cycloalkane molecule. Preferably, it has 3 to 20 carbon atoms, more preferably 3 to 10 carbon atoms. Specific examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, norbornelalkyl, adamantylalkyl, but are not limited thereto.

[0030] The aryl group described in this invention refers to the general term for the monovalent group obtained by removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably with 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited thereto; the polycyclic aryl refers to an aryl group containing two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited thereto; the fused-ring aryl refers to an aryl group containing two or more aromatic rings fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthryl, pyrene, perylene, fluorene, benzo[a]fluorene, triphenylene, fluoranyl, 9,9'-spirodifluorene, etc., but not limited thereto.

[0031] The heteroaryl group described in this invention refers to a monovalent group obtained by removing a hydrogen atom from the parent nucleus of a heterocyclic aromatic hydrocarbon molecule. It may contain one or more of N, O, P, S, Si, and Se as heteroatoms, and can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. Preferably, it has 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, particularly preferably 2 to 20 carbon atoms, even more preferably 2 to 12 carbon atoms, and most preferably 2 to 7 carbon atoms. The monocyclic heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; the polycyclic heteroaryl groups include bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, etc., but are not limited thereto; the fused-ring heteroaryl groups include quinolinyl, isoquinolinyl, indolyl, benzothiopheneyl, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, carbazoleyl, benzocarbazoleyl, acridineyl, spirofluoroxanthraceneyl, spirofluoroxanthraceneyl, etc., but are not limited thereto.

[0032] The arylene group referred to in this invention refers to the general term for the divalent group obtained by removing two hydrogen atoms from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, preferably with 6 to 30 carbon atoms, more preferably with 6 to 25 carbon atoms, particularly preferably with 6 to 18 carbon atoms, and most preferably with 6 to 12 carbon atoms. The monocyclic arylene includes, but is not limited to, phenylene; the polycyclic arylene includes, but is not limited to, biphenylene, terphenylene; and the fused-ring arylene includes, but is not limited to, naphthylene, anthracene, phenanthrene, pyrene, perylene, fluorene, trimethyleneene, 9,9'-spirodifluorene, etc., but is not limited to.

[0033] The heteroaryl group described in this invention refers to a divalent group obtained by removing two hydrogen atoms from the parent nucleus of a heterocyclic aromatic hydrocarbon molecule. It may contain one or more of N, O, P, S, Si, and Se as heteroatoms. More preferably, it has 2 to 30 carbon atoms, particularly preferably 2 to 20 carbon atoms, even more preferably 2 to 12 carbon atoms, and most preferably 2 to 7 carbon atoms. The heteroaryl group can be a monocyclic heteroaryl, a polycyclic heteroaryl, or a fused-ring heteroaryl. The monocyclic heteroaryl groups include, but are not limited to, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroloyl, oxazolyl, thiazolyl, and imidazolyl; the polycyclic heteroaryl groups include, but are not limited to, bipyridinyl, bipyrimidinyl, phenylpyridinyl, and phenylpyrimidine; the fused-ring heteroaryl groups include, but are not limited to, quinolinyl, isoquinolinyl, indolyl, benzothiopheneyl, benzofuranyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, carbazolyl, benzocarbazolyl, acridineyl, spirofluoroxanthenyl, and spirofluoroxanthenyl.

[0034] The substituents described in the "substituted or unsubstituted" of this invention may be the same as or different from each other, and are selected from any one of deuterium, tritium, cyano, nitro, trifluoromethyl, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group, preferably deuterium, cyano, halogen atom, trifluoromethyl ... Methyl, C1-C12 alkyl, C3-C12 cycloalkyl, C3-C25 silyl, C6-C30 aryl, C2-C30 heteroaryl, specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, tolyl, pentadeuterated phenyl, naphthyl, anthracene, phenanthrene, pyrene, triphenylene. yl, peryl, fluoranyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, carbazole, 9-phenylcarbazole, 9,9'-spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, pyridine Phosphoryl, furanyl, thiophenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, phenothiazinyl, phenothiazinyl, acridineyl, etc., but not limited to these.

[0035] The "linking to form a substituted or unsubstituted ring" described in this invention refers to two groups linked together by chemical bonds and optionally aromatized. For example:

[0036]

[0037] In this specification, the rings formed by the linkage can be aromatic or non-aromatic rings, and can be three-membered, four-membered, five-membered, six-membered, seven-membered, eight-membered, fused rings, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but not limited to these.

[0038] This invention provides a heterocyclic compound, which is represented by Formula 1:

[0039]

[0040] In Equation 1,

[0041] A is selected from formula 2 or formula 3, and -* represents the connection site;

[0042] R1 and R2 are independently selected from any one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C2-C20 heteroaryl groups, or any one of R1 and R2 can be directly bonded to L.

[0043] The R3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C20 heteroaryl, wherein m is selected from 0, 1, 2 or 3;

[0044] The R4 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C20 heteroaryl, wherein n is independently selected from 0, 1 or 2.

[0045] The L, L1, and L2 are independently selected from any one of single-bonded, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C2-C20 heteroarylene.

[0046] The W is selected from a single bond or O, S;

[0047] The X is independently selected from N or CR5;

[0048] The Y is independently selected from O, S, or C(R6)2;

[0049] The Z is independently selected from N or CR8;

[0050] The R5, R6, and R8 are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2-C20 heteroaryl, wherein two adjacent R5s may be connected to form a substituted or unsubstituted ring, and two adjacent R8s may be connected to form a substituted or unsubstituted ring.

[0051] Preferably, the "substitution" in this invention refers to substitution by any of the following groups, either mono- or poly-substituted: deuterium, cyano, halogen, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C6 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, and substituted or unsubstituted C2-C20 heteroaryl group.

[0052] Preferably, R3 is independently selected from hydrogen, deuterium, cyano, halogen, or any of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorene, dibenzofuranyl, dibenzothiophene, carbazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl.

[0053] Preferably, the heterocyclic compound is selected from one of the following structures:

[0054]

[0055] Preferably, the heterocyclic compound is selected from any one of the following structures:

[0056]

[0057] Preferably, the structure A is selected from one of the following structures:

[0058]

[0059]

[0060] The value of h is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the value of h1 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7; the value of h2 is independently selected from 0, 1, 2, 3, 4, 5, or 6; the value of h3 is independently selected from 0, 1, 2, 3, 4, or 5; the value of h4 is independently selected from 0, 1, 2, 3, or 4; the value of h5 is independently selected from 0, 1, 2, or 3; the value of i is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the value of j is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7; and the value of k is independently selected from 0, 1, 2, 3, 4, 5, or 6.

[0061] The La may or may not be present. When present, it is independently selected from any one of phenylene, biphenylene, naphthylene, deuterated phenylene, deuterated biphenylene, and deuterated naphthylene.

[0062] The limitations of R1, R2, R8, and W are the same as those in Equation 1.

[0063] Preferably, R1 and R2 are independently selected from hydrogen, deuterium, cyano, halogen, or any one of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, fluorene, dibenzofuranyl, dibenzothiophene, carbazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl.

[0064] Preferably, Formula 2 is selected from any one of the following groups:

[0065]

[0066]

[0067] Preferably, Formula 3 is selected from any one of the following groups:

[0068]

[0069]

[0070] Preferably, R8 is independently selected from hydrogen, deuterium, cyano, halogen, or any of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorene, dibenzofuranyl, dibenzothiophene, carbazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl.

[0071] Preferably, Ra is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or any one of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, dimethylphenylsilyl, methyldiphenylmethylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, carbazoyl, pyridinyl, pyrimidinyl, triazinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl;

[0072] h1 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; h2 is independently selected from 0, 1, 2, 3, 4, 5 or 6; h3 is independently selected from 0, 1, 2, 3, 4 or 5; h4 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

[0073] The n1 is independently selected from 0, 1, 2, 3, 4 or 5, the n2 is independently selected from 0, 1, 2, 3 or 4, and the n3 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0074] More preferably, the A structure is selected from one of the following structures:

[0075]

[0076]

[0077] Preferably, the Structurally independent structures are selected from one of the following structures:

[0078]

[0079] The p is independently selected from 0, 1, 2, 3, or 4; the q is independently selected from 0, 1, 2, or 3; the r is independently selected from 0, 1, or 2; the s is independently selected from 0 or 1; the n is independently selected from 0, 1, or 2.

[0080] The limitations of R4, R5, and R6 are the same as the definitions of R4, R5, and R6 in the preceding text of this specification.

[0081] Preferably, R4 and R5 are independently selected from hydrogen, deuterium, cyano, halogen, or any one of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorene, dibenzofuranyl, dibenzothiophene, carbazoyl, pyridyl, pyrimidinyl, triazinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl. Alternatively, two adjacent R5 groups may be linked to form any one of the following substituted or unsubstituted benzene rings, naphthyl rings, or phenanthrene rings.

[0082] More preferably, the Structurally independent structures are selected from one of the following structures:

[0083]

[0084]

[0085]

[0086] More preferably, the Structurally independent structures are selected from one of the following structures:

[0087]

[0088] Preferably, L, L1, and L2 are independently selected from single bonds or one of the following structures:

[0089]

[0090]

[0091] The R is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C20 heteroaryl.

[0092] The R 12Independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C20 heteroaryl;

[0093] The value of c is independently selected from 0, 1, 2, 3, or 4; the value of d is independently selected from 0, 1, 2, or 3; the value of e is independently selected from 0, 1, or 2.

[0094] The f is independently selected from 0 or 1; the g is independently selected from 0, 1, 2, 3, 4 or 5.

[0095] Preferably, R is independently selected from hydrogen, deuterium, cyano, halogen, or any of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorene, dibenzofuranyl, dibenzothiophene, carbazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl.

[0096] More preferably, L, L1, and L2 are independently selected from single bonds or one of the following structures:

[0097]

[0098]

[0099] Most preferably, the heterocyclic compound is selected from any one of the following compounds:

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132] The present invention also provides an organic electroluminescent device comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode, and the organic layer comprises one or more heterocyclic compounds as described in the present invention.

[0133] Specifically, the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region. Preferably, at least one layer of the hole transport region, the light-emitting layer, or the electron transport region contains one or more heterocyclic compounds as described in this invention.

[0134] Preferably, the electron transport region comprises at least one electron transport layer or hole blocking layer, wherein the at least one electron transport layer or hole blocking layer comprises one or more heterocyclic compounds as described in this invention.

[0135] Preferably, the light-emitting layer comprises one or more heterocyclic compounds as described in this invention.

[0136] More preferably, the organic layer is located between the anode and the cathode, and the organic layer includes an electron transport layer, which includes one or more heterocyclic compounds as described in this invention.

[0137] More preferably, the organic layer is located between the anode and the cathode, and the organic layer includes a hole-blocking layer, which includes one or more heterocyclic compounds as described in this invention.

[0138] More preferably, the light-emitting layer comprises a host material and a guest material, wherein the host material is selected from one or more heterocyclic compounds described in this invention.

[0139] Preferably, the organic layer can be a single-layer structure or a multi-layer structure, and each organic layer can also contain a single-layer or multi-layer structure. The single-layer structure can be composed of a single substance or two or more substances.

[0140] Preferably, the organic electroluminescent device of the present invention has the following structure, but is not limited thereto:

[0141] (1) Substrate / Anode / Hole transport layer / Light emission layer / Electron transport layer / Cathode;

[0142] (2) Substrate / Anode / Hole injection layer / Hole transport layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode;

[0143] (3) Substrate / Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode;

[0144] (4) Substrate / Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Electron injection layer / Cathode;

[0145] (5) Substrate / Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emitting layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode;

[0146] (6) Substrate / Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode / Covering layer;

[0147] In the organic electroluminescent device of the present invention, apart from the heterocyclic compound material described in the present invention, materials known in the art can be used for each functional layer. The following describes the layers and materials that may be involved in the above device:

[0148] The anode material of this invention is typically a material with a high work function, thereby improving hole injection efficiency. Specific examples include, but are not limited to: metals or alloys thereof, such as silver (Ag), aluminum (Al), gold (Au), copper (Cu), nickel (Ni), molybdenum (Mo), titanium (Ti), zinc (Zn), palladium (Pd), platinum (Pt), vanadium (V), chromium (Cr), etc.; metal oxides, such as indium zinc oxide (IZO), indium tin oxide (ITO), indium oxide (InO), zinc oxide (ZnO), etc.; compositions of oxides and metals, such as zinc oxide:aluminum (ZnO:Al), tin oxide:antimony (SnO2:Sb), etc.; and multilayer materials, such as aluminum / gold (Al / Au), aluminum / silver (Al / Ag), etc.

[0149] The cathode material of this invention is typically a material with a low work function, thereby improving the efficiency of electron injection. Specific examples include, but are not limited to: metals, such as indium (In), silver (Ag), magnesium (Mg), aluminum (Al), etc.; metal alloys, such as lithium-aluminum alloy (Li:Al), magnesium-silver alloy (Mg:Ag), etc.; and laminated materials, such as magnesium / aluminum (Mg / Al), magnesium / silver (Mg / Ag), aluminum / silver (Al / Ag), etc.

[0150] The hole injection material of the present invention preferably has a good hole-accepting ability, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably a value between the work function of the anode material and the HOMO of the adjacent organic material layer. Specific examples include, but are not limited to: metalloporphyrins, oligothiophenes, arylamine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, and conductive polymers based on polyaniline and polythiophene.

[0151] The hole transport material of the present invention is typically a material with a high hole mobility, thereby transporting the received holes to the emissive layer. Specific examples of hole transport materials that can be used in the present invention include, but are not limited to: aromatic amine derivatives, such as N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), N4,N4'-di([1,1'-biphenyl]-4-yl)-N4'-(9,9-dimethyl-9H-fluorene-2-yl)-N4-phenyl-[1,1':2',1 [1,1'-triphenyl]-4,4'-diamine, N4,N4'-di([1,1'-biphenyl]-4-yl)-N4'-(9,9-dimethyl-9H-fluorene-2-yl)-N4-phenyl-[1,1':2',1”-triphenyl]-4,4'-diamine, N4,N4,N4”,N4”-tetra([1,1'-biphenyl]-4-yl)-[1,1':4',1”-triphenyl]-4,4”-diamine, etc.; high molecular weight materials such as polyvinylcarbazole (PVC), etc.

[0152] The luminescent material of this invention has the function of receiving holes and electrons and combining them to emit visible light. According to the emission color, it can be divided into red light materials, green light materials, and blue light materials. It typically contains a host material and a guest material. The host material of the luminescent material, in addition to the heterocyclic compounds described in this invention, may also include, but is not limited to: stilbene derivatives, stilbeneylaryl derivatives, triarylamine derivatives, carbazole derivatives, anthracene derivatives, and pyrene derivatives. Specific examples of the guest material of the luminescent material include, but are not limited to: platinum complexes, rhodium complexes, iridium complexes, osmium complexes, anthracene derivatives, pyrene derivatives, and perylene derivatives. Typically, the doping ratio of the guest material in the luminescent layer is 0.01% to 20%, preferably 0.1% to 10%, and more preferably 1% to 10%.

[0153] The electron transport region of the present invention can be selected from at least one of a hole blocking layer, an electron transport layer, and an electron injection layer. Furthermore, the electron transport region can be composed of a single-layer (a single layer containing a single material, or a single layer containing multiple materials) or a multi-layer (multiple layers containing multiple materials) structure.

[0154] The hole-blocking material of the present invention typically possesses excellent hole-blocking capabilities to confine holes within the light-emitting layer. In addition to the heterocyclic compounds described in this invention, other materials may include, but are not limited to, imidazole derivatives, azabenzene derivatives, anthraquinone derivatives, anthrone derivatives, quinoline derivatives, etc.

[0155] The electron transport material of this invention typically needs to have good electron transport capability in order to effectively inject electrons into the light-emitting layer. In addition to the heterocyclic compounds described in this invention, other materials may include, but are not limited to: metal chelates, thiazole derivatives, diazole derivatives, aziridine derivatives, cyano compounds, quinoline derivatives, phenanthroline derivatives, imidazole derivatives, etc.

[0156] The electron injection material of this invention is typically a material with good electron injection capability in order to reduce the potential barrier between the cathode and the electron transport layer. Specific examples include, but are not limited to: alkali metal salts, such as lithium fluoride; alkaline earth metal salts, such as magnesium fluoride; metal complexes of hydroxyquinoline derivatives, such as lithium hydroxyquinoline; metal oxides, such as aluminum oxide, etc. These compounds can be used alone or in combination with other materials.

[0157] The manufacturing method of each film layer in the organic electroluminescent device of the present invention can be a known method such as dry film deposition or wet film deposition. Specific examples include, but are not limited to, vacuum evaporation, plasma deposition, spin coating, immersion deposition, and spray coating.

[0158] The organic electroluminescent device of the present invention is mainly used in the field of information display, such as organic solar cells, lighting sources, flexible OLEDs, VR, etc.

[0159] Synthesis Examples

[0160] The present invention provides the following preparation method, but the preparation method of the present invention is not limited thereto.

[0161] Route 1:

[0162]

[0163] Route 2:

[0164]

[0165] The X a X b X c X d X e X f X g X h The halogens Cl, Br, or I are represented independently.

[0166] The present invention does not impose any particular restrictions on the source of raw materials involved in the embodiments, which can be obtained from commercially available products or preparation methods known to those skilled in the art.

[0167] The mass spectrometry instrument used was a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters Instruments, UK, with chloroform as the solvent; the elemental analysis instrument used was a Vario EL cube organic elemental analyzer from Elementar, Germany, with sample masses of 5-10 mg.

[0168] [Synthetic Example 1] Synthesis of Compound 8

[0169]

[0170] Preparation of intermediate A-8:

[0171] Under nitrogen protection, 200 mL of tetrahydrofuran, a-8 (110.00 mmol, 38.81 g), b-8 (112.00 mmol, 28.44 g), pd(dppf)Cl2 (0.55 mmol, 0.40 g), and potassium acetate (275.00 mmol, 26.99 g) were added to a three-necked flask. The mixture was stirred, and the solution was heated under reflux for 6.5 h. After the reaction was complete, the mixture was cooled, and 200 mL of water was added. The mixture was filtered and dried in a vacuum oven. The residue was recrystallized from toluene:ethanol = 10:1 to give intermediate A-8 (39.11 g, 80%); HPLC purity ≥99.33%. Mass spectrometry m / z: 444.2272 (theoretical value: 444.2261).

[0172] Preparation of intermediate B-8

[0173] Under nitrogen protection, intermediates A-8 (80.00 mmol, 35.55 g), C-8 (82.00 mmol, 15.70 g), Pd(PPh3)4 (0.80 mmol, 0.92 g), K2CO3 (120.00 mmol, 16.58 g), 140 mL of toluene, 70 mL of ethanol, and 70 mL of water were added to a reaction flask. The mixture was stirred and reacted under reflux for 4 h. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with ethanol. Finally, the filter cake was recrystallized from toluene to obtain intermediate B-8 (26.77 g, 78%); HPLC purity ≥99.61%. Mass spectrometry m / z: 428.1323; theoretical value: (428.1332).

[0174] Preparation of intermediate N-8:

[0175] Under nitrogen protection, 200 mL of tetrahydrofuran, B-8 (50.00 mmol, 21.45 g), b-8 (52.00 mmol, 13.20 g), pd(dppf)Cl2 (0.25 mmol, 0.18 g), and potassium acetate (125.00 mmol, 12.27 g) were added to a three-necked flask. The mixture was stirred, and the solution was heated under reflux for 6.5 h. After the reaction was complete, the mixture was cooled, and 200 mL of water was added. The mixture was filtered and dried in a vacuum oven. The residue was recrystallized from toluene:ethanol = 20:1 to give intermediate N-8 (19.78 g, 76%); HPLC purity ≥99.85%. Mass spectrometry m / z: 520.2561 (theoretical value: 520.2574).

[0176] Preparation of intermediate I-8:

[0177] Under nitrogen protection, 200 mL of tetrahydrofuran, m-8 (90.00 mmol, 24.33 g), b-8 (182.00 mmol, 46.22 g), pd(dppf)Cl2 (0.45 mmol, 0.33 g), and potassium acetate (225.00 mmol, 22.08 g) were added to a three-necked flask. The mixture was stirred and refluxed for 7.5 h. After the reaction was complete, the mixture was cooled, 250 mL of water was added, and the mixture was filtered and dried in a vacuum oven. The residue was recrystallized from toluene:ethanol = 10:1 to give intermediate I-8 (24.60 g, 75%); HPLC purity ≥99.29%. Mass spectrometry m / z: 364.1773 (theoretical value: 364.1784).

[0178] Preparation of intermediate M-8:

[0179] Under nitrogen protection, 200 mL of DMF, I-8 (60.00 mmol, 21.87 g), d-8 (122.00 mmol, 24.16 g), and pd(dppf)Cl2 (0.40 mmol, 0.29 g) were added to a three-necked flask and stirred. Then, an aqueous solution of K3PO4 (60.00 mmol, 12.74 g) was added, and the mixture was heated to 150 °C and refluxed for 24 h. The reaction was then spotted onto a TLC plate, indicating complete reaction. After natural cooling, distilled water was added, followed by extraction with 400 mL of dichloromethane. The layers were separated, and the extract was dried over anhydrous sodium sulfate, filtered, and the filtrate was rotary evaporated and recrystallized from toluene to obtain intermediate M-8 (14.77 g, 71%); HPLC purity ≥99.79%. Mass spectrometry m / z: 346.0518 (theoretical value: 346.0509).

[0180] Preparation of compound 8:

[0181] Under nitrogen protection, 100 mL of tetrahydrofuran, M-8 (30.00 mmol, 10.40 g), N-8 (32.00 mmol, 16.66 g), Pd2(dba)3 (0.30 mmol, 0.27 g), 50% tri-tert-butylphosphine (0.60 mmol, 0.12 g), and sodium tert-butoxide (45.00 mmol, 4.32 g) were added to a three-necked flask. The mixture was stirred and refluxed for 10 h. A sample was spotted onto a TLC plate, indicating complete reaction. After natural cooling, distilled water was added, followed by extraction with 200 mL of dichloromethane. The layers were separated, and the extract was dried over anhydrous sodium sulfate, filtered, and the filter cake was washed with ethanol. Recrystallization from toluene yielded compound 8 (15.22 g, 72%); HPLC purity ≥99.95%. Mass spectrometry m / z: 704.2475 (theoretical value: 704.2464). Theoretical element content (%) C 51 H 32 N2O2: C, 86.91; H, 4.58; N, 3.97. Measured elemental content (%): C, 86.95; H, 4.59; N, 3.95.

[0182] [Synthetic Example 2] Synthesis of Compound 12

[0183]

[0184] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-12, c-8 with an equimolar amount of c-12, and d-8 with an equimolar amount of d-12, yielding compound 12 (17.29 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 778.2860 (theoretical value: 778.2872). Theoretical elemental content (%) C 59 H 38 O2: C, 90.97; H, 4.92. Measured elemental content (%): C, 90.94; H, 4.93.

[0185] [Synthetic Example 3] Synthesis of Compound 39

[0186]

[0187] Following the preparation method of Synthesis Example 1, c-8 was replaced with an equimolar amount of c-39, and d-8 was replaced with an equimolar amount of d-39, yielding compound 39 (16.18 g); HPLC purity ≥ 99.98%. Mass spectrometry m / z: 738.2345 (theoretical value: 738.2353). Theoretical elemental content (%) C 53 H 30 D4S2: C, 86.14; H, 5.18. Measured elemental content (%): C, 86.15; H, 5.16.

[0188] [Synthetic Example 4] Synthesis of Compound 51

[0189]

[0190] Following the preparation method of Example 1, B-8 was replaced with an equimolar amount of B-51, and d-8 was replaced with an equimolar amount of d-12, yielding compound 51 (14.67 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 626.2238 (theoretical value: 626.2246). Theoretical elemental content (%) C 47 H 30 O2: C, 90.07; H, 4.82. Measured elemental content (%): C, 90.05; H, 4.83.

[0191] [Synthetic Example 5] Synthesis of Compound 92

[0192]

[0193] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-92, c-8 with an equimolar amount of c-92, and d-8 with an equimolar amount of d-12, yielding compound 92 (17.17 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 752.2728 (theoretical value: 752.2715). Theoretical elemental content (%) C 57 H 36 O2: C, 90.93; H, 4.82. Measured elemental content (%): C, 90.91; H, 4.85.

[0194] [Synthetic Example 6] Synthesis of Compound 105

[0195]

[0196] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-105, and d-8 was replaced with an equimolar amount of d-12, yielding compound 105 (15.60 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 702.2545 (theoretical value: 702.2559). Theoretical elemental content (%) C 53 H 34 O2: C, 90.57; H, 4.88. Measured elemental content (%): C, 90.54; H, 4.93.

[0197] [Synthetic Example 7] Synthesis of Compound 113

[0198]

[0199] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-113, and d-8 was replaced with an equimolar amount of d-12, yielding compound 113 (16.94 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 752.2723 (theoretical value: 752.2715). Theoretical elemental content (%) C 57 H 36 O2: C, 90.93; H, 4.82. Measured elemental content (%): C, 90.95; H, 4.81.

[0200] [Synthetic Example 8] Synthesis of Compound 126

[0201]

[0202] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-126, and d-8 was replaced with an equimolar amount of d-12, yielding compound 126 (16.07 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 704.2451 (theoretical value: 704.2464). Theoretical elemental content (%) C 51 H 32 N2O2: C, 86.91; H, 4.58; N, 3.97. Measured elemental content (%): C, 86.93; H, 4.57; N, 3.99.

[0203] [Synthetic Example 9] Synthesis of Compound 133

[0204]

[0205] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-133, and d-8 was replaced with an equimolar amount of d-133, yielding compound 133 (19.51 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 902.3197 (theoretical value: 902.3185). Theoretical elemental content (%) C 69 H 42 O2: C, 91.77; H, 4.69. Measured elemental content (%): C, 91.75; H, 4.70.

[0206] [Synthetic Example 10] Synthesis of Compound 140

[0207]

[0208] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-105, and d-8 was replaced with an equimolar amount of d-140 to obtain compound 140 (15.60 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 702.2569 (theoretical value: 702.2559). Theoretical elemental content (%) C 53 H 34 O2: C, 90.57; H, 4.88. Measured elemental content (%): C, 90.59; H, 4.85.

[0209] [Synthetic Example 11] Synthesis of Compound 216

[0210]

[0211] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-105, c-8 with an equimolar amount of c-12, and d-8 with an equimolar amount of d-216, yielding compound 216 (16.59 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 778.2885 (theoretical value: 778.2872). Theoretical elemental content (%) C 59 H 38 O2: C, 90.97; H, 4.92. Measured elemental content (%): C, 90.95; H, 4.96.

[0212] [Synthetic Example 12] Synthesis of Compound 255

[0213]

[0214] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-105, c-8 with an equimolar amount of c-255, and d-8 with an equimolar amount of d-12, yielding compound 255 (18.92 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 818.3177 (theoretical value: 818.3185). Theoretical elemental content (%) C 62 H 42 O2: C, 90.92; H, 5.17. Measured elemental content (%): C, 90.94; H, 5.14.

[0215] [Synthetic Example 13] Synthesis of Compound 272

[0216]

[0217] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of B-51, and d-8 was replaced with an equimolar amount of d-12, yielding compound 272 (19.24 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 854.3174 (theoretical value: 854.3185). Theoretical elemental content (%) C 65 H 42 O2: C, 91.31; H, 4.95. Measured elemental content (%): C, 91.29; H, 4.99.

[0218] [Synthetic Example 14] Synthesis of Compound 305

[0219]

[0220] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-105, c-8 with an equimolar amount of c-12, and d-8 with an equimolar amount of d-305, yielding compound 305 (19.55 g); HPLC purity ≥ 99.98%. Mass spectrometry m / z: 930.3480 (theoretical value: 930.3498). Theoretical elemental content (%) C 71 H 46 O2: C, 91.58; H, 4.98. Measured elemental content (%): C, 91.54; H, 5.00.

[0221] [Synthetic Example 15] Synthesis of Compound 308

[0222]

[0223] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-133, c-8 with an equimolar amount of c-12, and d-8 with an equimolar amount of d-308, yielding compound 308 (21.97 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 1030.3823 (theoretical value: 1030.3811). Theoretical elemental content (%) C 79 H 50 O2: C, 92.01; H, 4.89. Measured elemental content (%): C, 92.05; H, 4.88.

[0224] [Synthetic Example 16] Synthesis of Compound 310

[0225]

[0226] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-133, c-8 with an equimolar amount of c-310, and d-8 with an equimolar amount of d-272, yielding compound 310 (19.82 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 904.3355 (theoretical value: 904.3341). Theoretical elemental content (%) C 69 H 44 O2: C, 91.56; H, 4.90. Measured elemental content (%): C, 91.52; H, 4.93.

[0227] [Synthetic Example 17] Synthesis of Compound 315

[0228]

[0229] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-105, c-8 with an equimolar amount of c-315, and d-8 with an equimolar amount of d-315, yielding compound 315 (19.52 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 855.3128 (theoretical value: 855.3137). Theoretical elemental content (%) C 64 H 41 NO2: C, 89.80; H, 4.83; N, 1.64. Measured elemental content (%): C, 89.81; H, 4.82; N, 1.67.

[0230] [Synthetic Example 18] Synthesis of Compound 328

[0231]

[0232] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-133, c-8 with an equimolar amount of c-12, and d-8 with an equimolar amount of d-328, yielding compound 328 (19.32 g); HPLC purity ≥ 99.98%. Mass spectrometry m / z: 932.3415 (theoretical value: 932.3403). Theoretical elemental content (%) C 69 H 44 N2O2: C, 88.82; H, 4.75; N, 3.00. Measured elemental content (%): C, 88.88; H, 4.72; N, 2.99.

[0233] [Synthetic Example 19] Synthesis of Compound 331

[0234]

[0235] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-105, c-8 with an equimolar amount of c-39, and d-8 with an equimolar amount of d-12, yielding compound 331 (15.69 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 7062818 (theoretical value: 706.2810). Theoretical elemental content (%) C 53 H 30 D4O2: C, 90.06; H, 5.42. Measured elemental content (%): C, 90.05; H, 5.45.

[0236] [Synthetic Example 20] Synthesis of Compound 343

[0237]

[0238] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-343, and d-8 was replaced with an equimolar amount of d-12, yielding compound 343 (16.66 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 730.2880 (theoretical value: 730.2872). Theoretical elemental content (%) C 55 H 38 O2: C, 90.38; H, 5.24. Measured elemental content (%): C, 90.35; H, 5.28.

[0239] [Synthetic Example 21] Synthesis of Compound 356

[0240]

[0241] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-356, and d-8 was replaced with an equimolar amount of d-12, yielding compound 356 (18.08 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 836.3666 (theoretical value: 836.3654). Theoretical elemental content (%) C 63 H 48 O2: C, 90.40; H, 5.78. Measured element content (%): C, 90.38; H, 5.81.

[0242] [Synthetic Example 22] Synthesis of Compound 361

[0243]

[0244] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-105, c-8 with an equimolar amount of c-12, and d-8 with an equimolar amount of d-361, yielding compound 361 (20.67 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 930.3490 (theoretical value: 930.3498). Theoretical elemental content (%) C 71 H 46 O2: C, 91.58; H, 4.98. Measured elemental content (%): C, 91.63; H, 4.97.

[0245] [Synthetic Example 23] Synthesis of Compound 366

[0246]

[0247] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-366, c-8 with an equimolar amount of c-12, and d-8 with an equimolar amount of d-366, yielding compound 366 (17.57 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 780.2785 (theoretical value: 780.2777). Theoretical elemental content (%) C 57 H 36 N2O2: C, 87.67; H, 4.65; N, 3.59. Measured elemental content (%): C, 87.66; H, 4.68; N, 3.60.

[0248] [Synthetic Example 24] Synthesis of Compound 375

[0249]

[0250] Preparation of intermediate d-375:

[0251] Under nitrogen protection, 100 mL of tetrahydrofuran, g-375 (150.00 mmol, 36.60 g), h-375 (152.00 mmol, 43.62 g), pd2(dba)3 (1.50 mmol, 1.37 g), 50% tri-tert-butylphosphine (3.00 mmol, 0.61 g), and sodium tert-butoxide (225.00 mmol, 21.62 g) were added to a three-necked flask. The mixture was stirred and refluxed for 10 h. A sample was spotted onto a TLC plate, indicating complete reaction. After natural cooling, distilled water was added, and the mixture was extracted with 200 mL of dichloromethane. The layers were separated, and the extract was dried over anhydrous sodium sulfate, filtered, and the filtrate was rotary evaporated and recrystallized from toluene to obtain intermediate d-375 (32.43 g, 78%); HPLC purity ≥99.80%. Mass spectrometry m / z: 276.0070 (theoretical value: 276.0088).

[0252] Following the preparation method of Example 1, B-8 was replaced with an equimolar amount of a-105, and d-8 was replaced with an equimolar amount of d-375, yielding compound 375 (16.76 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 786.3381 (theoretical value: 786.3374). Theoretical elemental content (%) C 59 H 30 D8O2: C, 90.04; H, 5.89. Measured elemental content (%): C, 90.07; H, 5.88.

[0253] [Synthetic Example 25] Synthesis of Compound 388

[0254]

[0255] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-105, c-8 with an equimolar amount of c-310, m-8 with an equimolar amount of m-388, and d-8 with an equimolar amount of d-315, yielding compound 388 (20.96 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 918.3485 (theoretical value: 918.3498). Theoretical elemental content (%) C 70 H 46 O2: C, 91.47; H, 5.04. Measured elemental content (%): C, 91.49; H, 5.05.

[0256] [Synthetic Example 26] Synthesis of Compound 391

[0257]

[0258] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-391, and d-8 was replaced with an equimolar amount of d-12, yielding compound 391 (18.32 g); HPLC purity ≥ 99.98%. Mass spectrometry m / z: 792.2675 (theoretical value: 792.2664). Theoretical elemental content (%) C 59 H 36 O3: C, 89.37; H, 4.58. Measured elemental content (%): C, 89.38; H, 4.55.

[0259] [Synthetic Example 27] Synthesis of Compound 475

[0260]

[0261] Following the preparation method of Example 1, a-8 was replaced with an equimolar amount of a-105, and d-8 was replaced with an equimolar amount of d-475, yielding compound 475 (19.43 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 886.2738 (theoretical value: 886.2728). Theoretical elemental content (%) C 65 H 42 S2: C, 88.00; H, 4.77. Measured elemental content (%): C, 88.03; H, 4.75.

[0262] [Synthetic Example 28] Synthesis of Compound 533

[0263]

[0264] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-533, and d-8 was replaced with an equimolar amount of d-475, yielding compound 533 (20.52 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 911.2695 (theoretical value: 911.2680). Theoretical elemental content (%) C 66 H 41 NS2: C, 86.90; H, 4.53; N, 1.54. Measured elemental content (%): C, 86.88; H, 4.51; N, 1.55.

[0265] [Synthetic Example 29] Synthesis of Compound 567

[0266]

[0267] Following the preparation method of Example 1, a-8 was replaced with an equimolar amount of a-133, and d-8 was replaced with an equimolar amount of d-567, yielding compound 567 (17.87 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 850.3609 (theoretical value: 850.3600). Theoretical elemental content (%) C 67 H 46 C, 94.55; H, 5.45. Measured elemental content (%): C, 94.57; H, 5.44.

[0268] [Synthetic Example 30] Synthesis of Compound 624

[0269]

[0270] Preparation of intermediate N-216:

[0271] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-105, and c-8 was replaced with an equimolar amount of c-12 to obtain compound N-216 (23.56 g, 79%); HPLC purity ≥99.84%. Mass spectrometry m / z: 596.2870 (theoretical value: 596.2887).

[0272] Preparation of intermediate C-624:

[0273] Under nitrogen protection, 200 mL of tetrahydrofuran, m-624 (150.00 mmol, 47.60 g), b-8 (152.00 mmol, 38.60 g), pd(dppf)Cl2 (0.75 mmol, 0.55 g), and potassium acetate (375.00 mmol, 36.80 g) were added to a three-necked flask. The mixture was stirred and refluxed for 8 h. After the reaction was complete, the mixture was cooled, 300 mL of water was added, and the mixture was filtered and dried in a vacuum oven. The residue was recrystallized from toluene:ethanol = 10:1 to give intermediate C-624 (39.04 g, 82%); HPLC purity ≥99.11%. Mass spectrometry m / z: 316.0028 (theoretical value: 316.0037).

[0274] Preparation of intermediate D-624:

[0275] Under nitrogen protection, 200 mL of DMF, C-624 (120.00 mmol, 38.09 g), g-375 (122.00 mmol, 29.77 g), and pd(dppf)Cl2 (0.80 mmol, 0.59 g) were added to a three-necked flask and stirred. Then, an aqueous solution of K3PO4 (120.00 mmol, 25.47 g) was added, and the mixture was heated to 150 °C and refluxed for 24 h. The reaction was then spotted onto a TLC plate, indicating complete reaction. After natural cooling, distilled water was added, and the mixture was extracted with 400 mL of dichloromethane. The layers were separated, and the extract was dried over anhydrous sodium sulfate, filtered, and the filtrate was rotary evaporated and recrystallized from toluene to obtain intermediate D-624 (29.53 g, 80%); HPLC purity ≥99.20%. Mass spectrometry m / z: 305.9438 (theoretical value: 305.9447).

[0276] Preparation of intermediate E-624:

[0277] Under nitrogen protection, 200 mL of tetrahydrofuran, D-624 (90.00 mmol, 27.68 g), b-8 (92.00 mmol, 23.36 g), pd(dppf)Cl2 (0.45 mmol, 0.33 g), and potassium acetate (225.00 mmol, 22.08 g) were added to a three-necked flask. The mixture was stirred and refluxed for 7.5 h. After the reaction was complete, the mixture was cooled, 250 mL of water was added, and the mixture was filtered and dried in a vacuum oven. The residue was recrystallized from toluene:ethanol = 10:1 to give intermediate E-624 (24.58 g, 77%); HPLC purity ≥99.31%. Mass spectrometry m / z: 354.1185 (theoretical value: 354.1194).

[0278] Preparation of intermediate M-624:

[0279] Under nitrogen protection, 200 mL of DMF, E-624 (60.00 mmol, 21.28 g), d-366 (62.00 mmol, 12.22 g), and pd(dppf)Cl2 (0.40 mmol, 0.29 g) were added to a three-necked flask and stirred. Then, an aqueous solution of K3PO4 (60.00 mmol, 12.74 g) was added, and the mixture was heated to 150 °C and refluxed for 24 h. The reaction was then spotted onto a TLC plate, indicating complete reaction. After natural cooling, distilled water was added, and the mixture was extracted with 400 mL of dichloromethane. The layers were separated, and the extract was dried over anhydrous sodium sulfate, filtered, and the filtrate was rotary evaporated and recrystallized from toluene to give intermediate M-624 (15.52 g, 75%); HPLC purity ≥99.72%. Mass spectrometry m / z: 344.0616 (theoretical value: 344.0604).

[0280] Preparation of compound 624:

[0281] Under nitrogen protection, 100 mL of tetrahydrofuran, M-624 (30.00 mmol, 10.34 g), N-216 (32.00 mmol, 19.09 g), Pd2(dba)3 (0.30 mmol, 0.27 g), 50% tri-tert-butylphosphine (0.60 mmol, 0.12 g), and sodium tert-butoxide (45.00 mmol, 4.32 g) were added to a three-necked flask. The mixture was stirred and refluxed for 10 h. A sample was spotted onto a TLC plate, indicating complete reaction. After natural cooling, distilled water was added, and the mixture was extracted with 200 mL of dichloromethane. The layers were separated, and the extract was dried over anhydrous sodium sulfate, filtered, and the filter cake was washed with ethanol. Recrystallization from toluene yielded compound 624 (17.99 g, 77%); HPLC purity ≥99.95%. Mass spectrometry m / z: 778.2880 (theoretical value: 778.2872). Theoretical element content (%) C 59H 38 O2: C, 90.97; H, 4.92. Measured elemental content (%): C, 90.94; H, 4.96.

[0282] [Synthetic Example 31] Synthesis of Compound 627

[0283]

[0284] Following the preparation method of Synthesis Example 30, c-12 was replaced with an equimolar amount of c-8, and d-366 was replaced with an equimolar amount of d-39, yielding compound 627 (16.82 g); HPLC purity ≥ 99.98%. Mass spectrometry m / z: 718.2338 (theoretical value: 718.2330). Theoretical elemental content (%) C 53 H 34 OS: C, 88.55; H, 4.77. Measured elemental content (%): C, 88.51; H, 4.78.

[0285] [Synthetic Example 32] Synthesis of Compound 633

[0286]

[0287] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of B-51, m-8 with an equimolar amount of m-633, and d-8 with an equimolar amount of d-315, yielding compound 633 (18.98 g); HPLC purity ≥ 99.98%. Mass spectrometry m / z: 854.3197 (theoretical value: 854.3185). Theoretical elemental content (%) C 65 H 42 O2: C, 91.31; H, 4.95. Measured elemental content (%): C, 91.33; H, 4.94.

[0288] [Synthetic Example 33] Synthesis of Compound 646

[0289]

[0290] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-646, and d-8 was replaced with an equimolar amount of d-12, yielding compound 646 (15.14 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 700.2416 (theoretical value: 700.2402). Theoretical elemental content (%) C 53 H 32 O2: C, 90.83; H, 4.60. Measured element content (%): C, 90.81; H, 4.59.

[0291] [Synthetic Example 34] Synthesis of Compound 701

[0292]

[0293] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-701, and d-8 was replaced with an equimolar amount of d-39, yielding compound 701 (17.62 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 782.2112 (theoretical value: 782.2102). Theoretical elemental content (%) C 57 H 34 S2: C, 87.43; H, 4.38. Measured elemental content (%): C, 87.45; H, 4.39.

[0294] [Synthetic Example 35] Synthesis of Compound 735

[0295]

[0296] Following the preparation method of Example 1, a-8 was replaced with an equimolar amount of a-735, c-8 with an equimolar amount of c-12, and d-8 with an equimolar amount of d-39, yielding compound 735 (19.62 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 920.3518 (theoretical value: 920.3510). Theoretical elemental content (%) C 67 H 52 S2: C, 87.35; H, 5.69. Measured elemental content (%): C, 87.33; H, 5.70.

[0297] [Synthetic Example 36] Synthesis of Compound 772

[0298]

[0299] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-772, and d-8 was replaced with an equimolar amount of d-12, yielding compound 772 (16.77 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 716.2344 (theoretical value: 716.2351). Theoretical elemental content (%) C 53 H 32 O3: C, 88.80; H, 4.50. Measured elemental content (%): C, 88.85; H, 4.49.

[0300] [Synthetic Example 37] Synthesis of Compound 820

[0301]

[0302] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-820, and d-8 was replaced with an equimolar amount of d-39, yielding compound 820 (18.70 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 798.2060 (theoretical value: 798.2051). Theoretical elemental content (%) C 57 H 34 OS2: C, 85.68; H, 4.29. Measured elemental content (%): C, 85.65; H, 4.28.

[0303] [Synthetic Example 38] Synthesis of Compound 857

[0304]

[0305] Following the preparation method of Example 1, a-8 was replaced with an equimolar amount of a-857, and d-8 was replaced with an equimolar amount of d-315, yielding compound 857 (19.81 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 868.2960 (theoretical value: 868.2977). Theoretical elemental content (%) C 65 H 40 O3: C, 89.84; H, 4.64. Measured element content (%): C, 89.85; H, 4.66.

[0306] [Synthetic Example 39] Synthesis of Compound 872

[0307]

[0308] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-872, and d-8 was replaced with an equimolar amount of d-872, yielding compound 872 (17.80 g); HPLC purity ≥ 99.98%. Mass spectrometry m / z: 750.1816 (theoretical value: 750.1800). Theoretical elemental content (%) C 51 H 30 N₂OS₂: C, 81.57; H, 4.03; N, 3.73. Measured elemental content (%): C, 81.58; H, 4.02; N, 3.75.

[0309] [Synthetic Example 40] Synthesis of Compound 922

[0310]

[0311] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-922, c-8 with an equimolar amount of c-922, and d-8 with an equimolar amount of d-12, yielding compound 922 (18.38 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 816.2923 (theoretical value: 816.2938). Theoretical elemental content (%) C 59 H 28 D8O2S: C, 86.73; H, 5.43. Measured elemental content (%): C, 86.75; H, 5.40.

[0312] [Synthetic Example 41] Synthesis of Compound 961

[0313]

[0314] Following the preparation method of Synthesis Example 1, a-8 was replaced with an equimolar amount of a-961, and d-8 was replaced with an equimolar amount of d-12, yielding compound 961 (16.76 g); HPLC purity ≥ 99.97%. Mass spectrometry m / z: 734.2042 (theoretical value: 734.2028). Theoretical elemental content (%) C 51 H 30 N2O2S: C, 83.36; H, 4.11; N, 3.81. Measured elemental content (%): C, 83.37; H, 4.12; N, 3.76.

[0315] [Device Example 1]

[0316] The ITO glass substrate was ultrasonically cleaned twice with a 5% glass cleaning solution for 20 minutes each time, followed by ultrasonic cleaning twice with deionized water for 10 minutes each time. It was then ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each, and dried at 120°C. The organic materials were sublimated to achieve a purity of over 99.99%.

[0317] First, the treated transparent ITO glass substrate is placed on the substrate holder of the vacuum evaporation apparatus. Then, HI-1 is deposited onto the substrate surface to form... A film of a certain thickness is used as a hole injection layer; based on this, HT-1 is deposited by evaporation as a hole transport layer with a thickness of [missing information]. Then, a BH1:BD1 ratio of 95:5 (mass ratio) is vacuum-deposited onto the hole transport layer as the emitting layer, with a thickness of [missing information]. Compound 8 of the present invention is deposited on the light-emitting layer as a hole-blocking layer with a thickness of [missing information]. Then, ET-1 and Liq (mass ratio 1:1) are deposited on top of the hole blocking layer as an electron transport layer, with a thickness of [missing information]. LiF was deposited on the electron transport layer as an electron injection layer, with a thickness of [missing information]. Al was thermally deposited as the cathode on the electron injection layer, with a thickness of [missing information].

[0318]

[0319] [Device Example 2-18]

[0320] Organic electroluminescent devices 2-18 were prepared by replacing compound 8 in device example 1 with compounds 12, 39, 51, 92, 140, 272, 315, 366, 475, 567, 627, 646, 701, 820, 857, 922, and 961 of the present invention as hole blocking layers, and the other preparation steps were the same as those in device example 1.

[0321] [Comparative Device Examples 1-2]

[0322] Comparative devices 1 and 2 were prepared by replacing compound 8 in device example 1 with comparative compound 1 and comparative compound 2 as hole blocking layers, and the other preparation steps were the same as those in device example 1.

[0323]

[0324] Table 1:

[0325]

[0326]

[0327] [Device Example 19]

[0328] The treated transparent ITO glass substrate is placed on the substrate holder of the vacuum evaporation apparatus, and then HI-1 is deposited on the substrate surface to form... A film of a certain thickness is used as a hole injection layer; based on this, HT-2 is deposited by evaporation as a hole transport layer with a thickness of [missing information]. A BH2:BD2 ratio of 95:5 (mass ratio) light-emitting layer was vacuum-deposited onto the hole transport layer as the luminescent layer, with a thickness of [missing information]. HB-1 is deposited on the light-emitting layer as a hole-blocking layer with a thickness of [missing information]. Then, compound 12 of the present invention and Liq (mass ratio 1:1) are vapor-deposited on top of the hole blocking layer as an electron transport layer, with a thickness of [missing information]. LiF was deposited on the electron transport layer as an electron injection layer, with a thickness of [missing information]. Al was thermally deposited as the cathode on the electron injection layer, with a thickness of [missing information].

[0329]

[0330] [Device Examples 20-40]

[0331] Organic electroluminescent devices 20-40 were prepared by replacing compound 12 in device example 19 with compounds 39, 51, 105, 126, 216, 255, 272, 308, 328, 343, 356, 375, 391, 475, 646, 735, 772, 820, 872, 922, and 961 of the present invention as the electron transport layer, and the other preparation steps were the same as those in device example 19.

[0332] [Comparative Device Examples 3-4]

[0333] Comparative devices 3 and 4 were prepared by replacing compound 12 in device example 19 with comparative compounds 3 and 4 as electron transport layers, and the other preparation steps were the same as those in device example 19.

[0334]

[0335] Table 2:

[0336]

[0337]

[0338] As shown in Tables 1 and 2, when the heterocyclic compounds described in this invention are used in the hole blocking layer or electron transport layer of organic electroluminescent devices, they can improve the luminous efficiency of organic electroluminescent devices, reduce the driving voltage, and extend the service life of the devices.

[0339] [Device Example 41]

[0340] The treated transparent ITO glass substrate is placed on the substrate holder of the vacuum evaporation apparatus, and then HI-1 is deposited on the substrate surface to form... A film of a certain thickness is used as a hole injection layer; based on this, HT-1 is deposited by evaporation as a hole transport layer with a thickness of [missing information]. Then, the compound 8:GH:GD of this invention, with a mass ratio of 46:46:8, is vacuum-deposited onto the hole transport layer as a light-emitting layer, with a thickness of [missing information]. HB-1 is deposited on the light-emitting layer as a hole-blocking layer with a thickness of [missing information]. Then, ET-1 and Liq (mass ratio 1:1) are deposited on top of the hole blocking layer as an electron transport layer, with a thickness of [missing information]. LiF was deposited on the electron transport layer as an electron injection layer, with a thickness of [missing information]. Al was thermally deposited as the cathode on the electron injection layer, with a thickness of [missing information].

[0341]

[0342] [Device Examples 42-80]

[0343] Organic electroluminescent devices 42-80 were prepared by replacing compound 8 in device example 41 with compounds 12, 39, 51, 92, 105, 113, 126, 133, 140, 216, 255, 272, 305, 308, 310, 315, 328, 331, 343, 356, 361, 366, 375, 388, 391, 475, 533, 567, 624, 627, 633, 646, 701, 735, 772, 820, 857, 872, and 922 of the present invention.

[0344] [Comparative Device Examples 5-6]

[0345] Comparative devices 5 and 6 were prepared by replacing compound 8 in device example 41 with comparative compounds 5 and 6, and the other preparation steps were the same as those in device example 41.

[0346]

[0347] Table 3:

[0348]

[0349]

[0350] As shown in Table 3, using the compounds of the present invention as the main body in the light-emitting layer of organic electroluminescent devices can improve the luminous efficiency of organic electroluminescent devices and extend the service life of the devices.

[0351] It should be noted that the present invention has been specifically described with reference to individual embodiments. For those skilled in the art, various modifications in form or detail to the present invention can be made without departing from the principle of the present invention, and such modifications also fall within the protection scope of the present invention.

Claims

1. A heterocyclic compound, characterized in that, The heterocyclic compound is represented by Formula 1: In Equation 1, the structure A is selected from one of the following structures: ； The h is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the h1 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7; the h3 is independently selected from 0, 1, 2, 3, 4, or 5; the i is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the k is independently selected from 0, 1, 2, 3, 4, 5, or 6. The La is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene; For connection sites; R1 and R2 are independently selected from any one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiopheneyl. R3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl groups, wherein m is selected from 0, 1, 2 or 3; The Structurally independent structures are selected from one of the following structures: ； The value of p is independently selected from 0, 1, 2, 3, or 4; the value of q is independently selected from 0, 1, 2, or 3; the value of n is independently selected from 0, 1, or 2. R4 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl, wherein n is independently selected from 0, 1 or 2; The L is selected from a single bond or one of the following structures: ； L1 and L2 are independently selected from single bonds or one of the following structures: ； The R is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl groups; The value of c is independently selected from 0, 1, 2, 3, or 4; The d is independently selected from 0, 1, 2, or 3; The W is selected from a single bond or O, S; The R5 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl groups, wherein two adjacent R5s may be connected to form a substituted or unsubstituted benzene ring. The R6 is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl groups; The R8 is independently selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted phenyl, and two adjacent R8s may be connected to form a substituted or unsubstituted benzene ring. The substituents in the "substituted or unsubstituted" group are the same or different from each other and are selected from deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, and deuterated tert-butyl.

2. The heterocyclic compound according to claim 1, characterized in that, The structure A is selected from one of the following structures: 。 3. The heterocyclic compound according to claim 1, characterized in that, The Structurally independent structures are selected from one of the following structures: 。 4. The heterocyclic compound according to claim 1, characterized in that, The Structurally independent structures are selected from one of the following structures: 。 5. The heterocyclic compound according to claim 1, characterized in that, L1 and L2 are independently selected from single bonds or one of the following structures: 。 6. The heterocyclic compound according to claim 1, characterized in that, The L is selected from a single bond or one of the following structures: ； L1 and L2 are independently selected from single bonds or one of the following structures: 。 7. A heterocyclic compound, characterized in that, The heterocyclic compound is selected from any one of the following compounds: 。 8. An organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode, characterized in that, The organic layer comprises one or more of the heterocyclic compounds described in any one of claims 1-7.

9. An organic electroluminescent device according to claim 8, characterized in that, The organic layer includes an electron transport region, which comprises at least one electron transport layer or a hole blocking layer, wherein the at least one electron transport layer or hole blocking layer comprises one or more heterocyclic compounds according to any one of claims 1-7.

10. An organic electroluminescent device according to claim 8, characterized in that, The organic layer includes a light-emitting layer, which contains one or more of the heterocyclic compounds according to any one of claims 1-7.

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