Heterocyclic compound and organic electroluminescent device

Abstract

The invention discloses a heterocyclic compound and an organic electroluminescent device. The compound comprises terpyridyl and the following connection structure: the compound can be used for preparing an N-type charge generation layer of an OLED (Organic Light Emitting Diode), can effectively reduce the power consumption of a device, improve the luminous efficiency, prolong the service life of the device and reduce the drift voltage, and has the potential of being applied to an AMOLED (Active Matrix / Organic Light Emitting Diode) industry.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescence technology, and specifically relates to a heterocyclic compound and an organic electroluminescence device. Background Technology

[0002] Currently, organic light-emitting diodes (OLEDs), as a next-generation display technology, have received widespread attention in the display and lighting fields, demonstrating broad application prospects. With the continuous development of OLED technology in display and lighting, higher demands are being placed on the performance of OLED devices, especially in terms of low power consumption, high efficiency, and long lifespan. Therefore, developing higher-performance functional materials and optimizing device structures have become current research hotspots.

[0003] In the most common OLED device structures, the following functional materials are typically included: hole injection materials, hole transport materials, electron transport materials, and luminescent materials (including host and guest materials). Electron transport materials, as a crucial functional material, directly influence electron mobility, ultimately affecting the OLED's luminous efficiency. Therefore, improving the mobility of electron transport materials and reducing device power consumption have become important directions for improving OLED device performance. By forming a tandem OLED structure, stacking multiple luminescent layers and sandwiching charge generation layers between them, mobility can be further improved. Charge generation layers typically include N-type and P-type charge generation layers, with the N-type charge generation layer playing a vital role as an electron transport material in improving mobility and reducing power consumption. However, performance improvements in these materials remain limited, and device efficiency and lifetime still require further improvement.

[0004] Therefore, it is necessary to develop charge generation layer materials with higher mobility. Summary of the Invention

[0005] This invention provides a heterocyclic compound that can be used to prepare the N-type charge generation layer of OLEDs. This compound has high electron mobility, which can effectively reduce device power consumption, improve luminous efficiency, extend device lifespan, and reduce drift voltage.

[0006] The first aspect of this invention relates to a heterocyclic compound having the structure shown in formula (1) or formula (2):

[0007]

[0008] Ar1 is selected from one of the structures shown in equations (A-1) to (A-4);

[0009]

[0010] R1-R6 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 heteroalkyl, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C2-C40 alkynyl, substituted or unsubstituted C3-C40 cycloalkyl, substituted or unsubstituted C3-C40 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C6 0 heteroaryl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C40 alkylsilyl, substituted or unsubstituted C6-C60 arylsilyl, substituted or unsubstituted C1-C40 alkylboryl, substituted or unsubstituted C6-C60 arylboryl, substituted or unsubstituted C6-C60 arylphosphinyl or substituted or unsubstituted C6-C60 arylamino;

[0011] Where a and c are each independently selected from integers from 0 to 3; b, d, and e are each independently selected from integers from 0 to 4; and f is selected from integers from 0 to 7.

[0012] L is selected from one of the structures shown in equations (B-1) to (B-6):

[0013]

[0014] R8 is 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 or C1-C40 alkoxy.

[0015] R9 is 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, C5-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.

[0016] m is selected from integers from 0 to 3; n is selected from integers from 0 to 4;

[0017] Ar2-Ar6 are each independently selected from substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C3-C60 heteroaryl;

[0018] In R1-R6 and Ar2-Ar6, the substitution is independently substituted by at least one of deuterium, halogen, cyano, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 hydrocarbon substituted or unsubstituted C6-C30 aryl, C1-C6 hydrocarbon substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions is from monosubstituted to the maximum number of substitutions;

[0019] The heteroatom in the heteroaryl, heteroalkyl, or heterocycloalkyl group is independently selected from at least one of O, S, N, Se, Si, or Ge.

[0020] The heterocyclic compound possesses a multi-coordination-site structure and high electron mobility, making it suitable as a charge generation layer material for OLED devices and showing potential for application in the AMOLED industry. This compound can coordinate with dopant metal ions, reducing the energy level difference between the N-type and P-type charge generation layers, promoting electron injection into the N-type charge generation layer, and maximizing electron transfer from the N-type charge generation layer to the adjacent electron transport layer, further improving device performance. Attached Figure Description

[0021] Figure 1 A schematic diagram of the structure of an organic electroluminescent device according to an embodiment of the present invention. Detailed Implementation

[0022] To enable those skilled in the art to more clearly understand the technical solutions described in this invention, 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 by this invention.

[0023] A first aspect of the present invention provides a heterocyclic compound having the structure shown in formula (1) or formula (2):

[0024]

[0025] Ar1 is selected from one of the structures shown in equations (A-1) to (A-4);

[0026]

[0027] R1-R6 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 heteroalkyl, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C2-C40 alkynyl, substituted or unsubstituted C3-C40 cycloalkyl, substituted or unsubstituted C3-C40 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C6 0 heteroaryl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C40 alkylsilyl, substituted or unsubstituted C6-C60 arylsilyl, substituted or unsubstituted C1-C40 alkylboryl, substituted or unsubstituted C6-C60 arylboryl, substituted or unsubstituted C6-C60 arylphosphinyl or substituted or unsubstituted C6-C60 arylamino;

[0028] Where a and c are each independently selected from integers from 0 to 3; b, d, and e are each independently selected from integers from 0 to 4; and f is selected from integers from 0 to 7.

[0029] L is selected from one of the structures shown in equations (B-1) to (B-6):

[0030]

[0031] R8 is 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 or C1-C40 alkoxy.

[0032] R9 is 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, C5-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.

[0033] m is selected from integers from 0 to 3; n is selected from integers from 0 to 4;

[0034] Ar2-Ar6 are each independently selected from substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C3-C60 heteroaryl;

[0035] In R1-R6 and Ar2-Ar6, the substitution is independently substituted by at least one of deuterium, halogen, cyano, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 hydrocarbon substituted or unsubstituted C6-C30 aryl, C1-C6 hydrocarbon substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions is from monosubstituted to the maximum number of substitutions;

[0036] The heteroatom in the heteroaryl, heteroalkyl, or heterocycloalkyl group is independently selected from at least one of O, S, N, Se, Si, or Ge.

[0037] Unless otherwise specified, "*" in the structural formula indicates a connection site, which usually means that the corresponding structure is connected to other atoms or groups through the site indicated by "*". For example, Ar1 is selected from formula (A-1), which means that Ar1 is connected to L through the site marked "*" in formula (A-1).

[0038] In some embodiments, the heterocyclic compounds described above are selected from one of the structures shown in formulas (C-1) to (C-8):

[0039]

[0040] In some embodiments, L is selected from one of the structures shown in equations (D-1) to (D-10):

[0041]

[0042] In some embodiments, R1-R6 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C5-C20 heteroaryl.

[0043] In some embodiments, R1-R6 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 heteroalkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C12 heterocycloalkyl, substituted or unsubstituted C6-C12 aryl, or substituted or unsubstituted C5-C12 heteroaryl.

[0044] Furthermore, R1-R6 are each independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C12 aryl or substituted or unsubstituted C5-C12 heteroaryl. Among them, aryl can be phenyl, biphenyl, naphthyl, etc.; heteroaryl can be pyridyl, etc.

[0045] In some embodiments, R8 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, or C3-C20 heterocycloalkyl.

[0046] In some embodiments, R8 is selected from hydrogen, deuterium, halogen, cyano, C1-C12 alkyl, C1-C12 heteroalkyl, C3-C12 cycloalkyl, or C3-C12 heterocycloalkyl.

[0047] Furthermore, R8 is selected from hydrogen, deuterium, halogen, cyano, or C1-C6 alkyl groups.

[0048] Furthermore, when L is selected from any of the structures shown in formulas (D-2) to (D-9), R8 is selected from hydrogen.

[0049] In some embodiments, R9 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C240 heteroalkyl, C2-C20 alkenyl, C2-20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl, or C5-C20 heteroaryl.

[0050] In some embodiments, R9 is selected from hydrogen, deuterium, halogen, cyano, C1-C12 alkyl, C1-C12 heteroalkyl, C3-C12 cycloalkyl, or C3-C12 heterocycloalkyl.

[0051] Furthermore, R9 is selected from hydrogen, deuterium, halogen, cyano or C1-C6 alkyl, and even further selected from hydrogen or deuterium.

[0052] In some embodiments, Ar2-Ar6 are each independently selected from substituted or unsubstituted C6-C30 aryl groups or substituted or unsubstituted C3-C30 heteroaryl groups.

[0053] In some embodiments, Ar2-Ar6 are each independently selected from the following groups, or are combinations of at least two of the following groups linked together: substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-dimethylfluorenyl... -Diphenylfluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted carbazole, substituted or unsubstituted pyridinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, or substituted or unsubstituted benzophenanthrene. The combined group refers to a structural unit formed by at least two groups as defined above linked or fused together by chemical bonds. In some embodiments, the chemical bond connection can be a single bond, for example, a combination of phenyl and naphthyl to form -phenyl-1-naphthyl- or -phenyl-2-naphthyl-. It should be understood that the combination of groups is contingent upon satisfying the Ar2-Ar6 carbon number range defined above.

[0054] In some embodiments, Ar2-Ar6 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted pyreneyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, or substituted or unsubstituted fluoranthyl.

[0055] In some embodiments, the substitutions in R1-R6 and Ar2-Ar6 are independently at least one of deuterium, halogen, cyano, C1-C6 alkyl, C3-C12 cycloalkyl, C1-C6 hydrocarbon substituted or unsubstituted C6-C20 aryl, C1-C6 hydrocarbon substituted or unsubstituted C3-C20 heteroaryl, wherein the number of substitutions is from monosubstituted to the maximum number of substitutions. For example, when the substituent is deuterium, it can be from monosubstituted to the maximum number of substitutions; when the substituent is an atom or group other than deuterium, it can be monosubstituted, disubstituted, or trisubstituted.

[0056] In some embodiments, the substitutions in R1-R6 and Ar2-Ar6 are independently substituted by at least one of deuterium, halogen, cyano, C1-C6 alkyl, C3-C12 cycloalkyl, C6-C12 aryl, and C3-C12 heteroaryl, wherein the number of substitutions ranges from monosubstituted to a maximum number of substituted groups. Specific substituents include, for example, deuterium, fluorine, cyano, methyl, tert-butyl, cyclohexyl, phenyl, or pyridyl.

[0057] In some embodiments, the heterocyclic compounds described above satisfy at least one of the following conditions:

[0058] c1) R1, R2, R4, and R5 are each independently selected from hydrogen, deuterium, or phenyl;

[0059] c2) R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl or substituted or unsubstituted naphthyl, wherein the substitution is independently substituted by at least one of fluorine, methyl, phenyl, and the number of substitutions is from monosubstituted to the maximum number of substitutions;

[0060] c3)R6 is selected from deuterium, deuterated or unsubstituted phenyl, deuterated or unsubstituted naphthyl or deuterated or unsubstituted pyridyl, wherein the number of deuterations ranges from monosubstituted to the maximum number of substituted.

[0061] c4)R8 is selected from hydrogen, deuterium, cyano or methyl;

[0062] c5)R9 is selected from hydrogen;

[0063] c6) Ar2-Ar5 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyrene, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophene, wherein the substitution is independently by at least one of deuterium, methyl, phenyl, cyclohexyl, tert-butyl, pyridyl, wherein the number of substitutions is from monosubstituted to the maximum number of substitutions;

[0064] c7)Ar6 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, or substituted or unsubstituted dibenzofuranyl; wherein the substitution is independently substituted by at least one of deuterium, fluorine, cyano, methyl, phenyl, or pyridyl, and the number of substitutions is from monosubstituted to the maximum number of substitutions.

[0065] In some embodiments, the heterocyclic compound described above is one of the following structural formulas, or one of the following structural formulas in which hydrogen is partially or completely substituted by deuterium or fluorine:

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075] A second aspect of the present invention provides an organic electroluminescent device comprising the heterocyclic compound described above.

[0076] In some embodiments, the organic electroluminescent device includes an anode and a cathode, with a functional layer between the anode and the cathode, the functional layer containing the aforementioned heterocyclic compound.

[0077] In some embodiments, a first light-emitting unit, a charge-generating layer, and a second light-emitting unit are sequentially stacked from the anode side to the cathode side in the functional layer, wherein the charge-generating layer contains the aforementioned heterocyclic compound.

[0078] In some embodiments, an N-type charge generation layer and a P-type charge generation layer are sequentially stacked from the first light-emitting unit side to the second light-emitting unit side, wherein the N-type charge generation layer contains the aforementioned heterocyclic compound.

[0079] In some embodiments, the N-type charge generation layer further comprises a doped material.

[0080] In some embodiments, the dopant material is selected from at least one of alkali metals (e.g., Li, Na, K), alkaline earth metals (e.g., Ca, Mg) or lanthanides (e.g., La, Yb, Ce).

[0081] In some embodiments, the mass percentage of the doped material in the N-type charge generation layer may be 0.1%-20%, or 1%-10%, or 1%-5%; the mass percentage of the heterocyclic compound may be 80%-99.9%, or 90%-99%, or 95%-99%.

[0082] In some embodiments, the first light-emitting unit is provided with a first hole functional layer, a first light-emitting layer, and a first electron functional layer stacked sequentially from the anode side to the charge generation layer side. As an example, the first hole functional layer is provided with a hole injection layer, a first hole transport layer, and a first electron blocking layer stacked sequentially from the anode side to the first light-emitting layer side; the first electron functional layer includes a first electron transport layer.

[0083] In some embodiments, the second light-emitting unit is provided with a second hole functional layer, a second light-emitting layer, and a second electron functional layer stacked sequentially from the charge generation layer towards the cathode side. As an example, the second hole functional layer is provided with a second hole transport layer and a second electron blocking layer stacked sequentially from the charge generation layer side towards the second light-emitting layer side; the second electron functional layer is provided with a second electron transport layer and an electron injection layer stacked sequentially from the second light-emitting layer side towards the cathode side.

[0084] In some embodiments, the functional layers are sequentially stacked from the anode side to the cathode side as follows: a hole injection layer, a first hole transport layer, a first electron blocking layer, a first light-emitting layer, a first electron transport layer, an N-type charge generation layer, a P-type charge generation layer, a second hole transport layer, a second electron blocking layer, a second light-emitting layer, a second electron transport layer, and an electron injection layer; wherein the N-type charge generation layer contains the aforementioned heterocyclic compound.

[0085] It should be noted that the present invention does not limit the stacked structure of the light-emitting unit, and those skilled in the art can use any stacked structure known in the prior art.

[0086] A third aspect of the present invention provides an optoelectronic element, including the organic electroluminescent device described above.

[0087] Non-limiting examples of optoelectronic components include: lighting fixtures (such as lamps), displays (such as automotive displays, computer displays, or television displays, where the display type may be an AMOLED display), or sensors, etc.

[0088] Based on the role of this heterocyclic compound in improving electron mobility, it can be used as a charge generation layer material in OLED devices. This can effectively reduce driving voltage, improve luminous efficiency, extend device lifetime, and reduce drift voltage, showing potential for application in the AMOLED industry. Specifically, the compound's multiple coordination sites allow for better coordination with dopants (such as alkali metals, alkaline earth metals, and lanthanides) and metal ions, reducing material degradation caused by metal ion migration within the device. This heterocyclic compound can reduce the energy level difference between the N-type and P-type charge generation layers, thereby promoting electron injection into the N-type charge generation layer and maximizing electron transfer from the N-type charge generation layer to the adjacent electron transport layer, further improving device performance.

[0089] definition

[0090] Unless otherwise specified, all general formulas and their subordinate general formulas (e.g., group designation Ar1, etc.) involved in this invention have the same scope of interpretation in all embodiments of this invention. The definitions of different symbols can be freely combined, and all such combinations fall within the protection scope of this invention.

[0091] The term "halogen" refers to one or more of fluorine, chlorine, bromine, or iodine, typically including fluorine, chlorine, or bromine.

[0092] The term "alkyl" refers to a straight-chain or branched saturated hydrocarbon group. Non-limiting examples of alkyl groups include methyl, ethyl, propyl, butyl, heptyl, decyl, etc. Each group includes various isomers; for example, butyl includes isomers such as n-butyl, isobutyl, sec-butyl, tert-butyl, etc.

[0093] The term "heteroalkyl" refers to an alkyl group in which at least one carbon atom is replaced by a non-carbon atom or a group containing a non-carbon atom. The non-carbon atom can be selected from at least one of O, S, N, Si, Ge, or Se, but does not include cases where the carbon atom serving as a linking site is replaced by a non-carbon atom (e.g., alkoxy, alkylsilyl, alkylboryl). Non-limiting examples of heteroalkyl groups include mercaptomethylmethane, methoxymethane, ethoxymethane, tert-butoxymethane, N,N-dimethylmethane, etc.

[0094] The term "alkoxy" refers to a group having an -O-alkyl group, i.e., an alkyl group as defined above connected to a given group or given structural formula via an oxygen atom. Non-limiting examples of alkoxy groups include methoxy, ethoxy, and tert-butoxy.

[0095] The term "alkenyl" refers to a hydrocarbon group containing at least one double bond. Non-limiting examples of alkenyl groups include: vinyl, propenyl, allyl, isopropenyl, 1-butadienyl, 2-butadienyl, 1-hextrienyl, 2-hextrienyl, and 3-hextrienyl.

[0096] The term "alkynyl" refers to a hydrocarbon group containing at least one triple bond. Non-limiting examples of alkynyl groups include ethynyl and propynyl.

[0097] The term "cycloalkyl" refers to a non-aromatic carbonyl ring consisting of at least two carbon atoms, which may include monocyclic, polycyclic, and spiroalkyl rings. Non-limiting examples of cycloalkyl rings include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl (including 1-adamantyl, 2-adamantyl), 1-norbornyl or 2-norbornyl, etc.

[0098] The term "heterocyclic alkyl" refers to a cycloalkyl group in which at least one carbon atom is replaced by a non-carbon atom, which may be selected from at least one of O, S, N, Si, Ge, or Se. Non-limiting examples of heterocyclic alkyl groups include epoxide butyl, epoxide pentyl, and epoxide hexyl.

[0099] The term "aryl" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom; it can be monocyclic or polycyclic. In a polycyclic aryl compound, at least one ring is an aromatic ring system. The multiple rings in a polycyclic aryl compound can be linked together by single bonds or can be fused together. Specific examples of aryl compounds include phenyl, naphthyl, anthraceneyl, phenanthryl, tetraphenyl, pyrene, etc. Benzyl, benzo[c]phenanthrene, benzo[g] Fluoryl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, biphenyl, triphenyl, tetraphenyl, fluoranthyl, etc.

[0100] The term "heteroaryl" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, wherein the non-carbon atom can be a monovalent group selected from a heterocyclic aromatic system of O, S, N, Se, Si or Ge, but does not include cases where the aryl group is attached to the host structure through a non-carbon atom group (e.g., aryloxy, arylsilyl, arylboryl, arylphosphinyl, arylamine). Specific examples of heteroaryl groups include pyrroleyl, pyrazinyl, pyridinyl, pyrimidinyl, triazinyl, indolyl, isoindolyl, imidazolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, dibenzothiopheneyl, azadibenzofuranyl, azadibenzothiopheneyl, diazadibenzofuranyl, diazadibenzothiopheneyl, quinolinyl, isoquinolinyl, quinoxolinyl, carbazoleyl, phenanthridineyl, acridineyl, phenanthridineyl, phenazinyl, phenthiazinyl, phenoxazinyl, oxazolinyl, oxadiazinyl, furazinyl, thiopheneyl, benzothiopheneyl, dihydroacridinyl, azacarbazoleyl, diazacarbazoleyl, quinazolinyl, etc.

[0101] The term "hydrocarbon group" refers to a group consisting only of carbon and hydrogen atoms, including saturated hydrocarbon groups (e.g., alkyl, cycloalkyl), unsaturated non-aromatic hydrocarbon groups (e.g., alkenyl, ynyl), and aromatic hydrocarbon groups (e.g., phenyl).

[0102] In the terms "alkylsilyl" or "arylsilyl," the number of alkyl or aryl groups can be one to three. "alkylboryl" includes monoalkylboryl and dialkylboryl, "arylboryl" includes monoarylboryl and diarylboryl, "arylphosphine" includes monoarylphosphine and diarylphosphine, and "arylamine" includes monoarylamine and diarylamine. In alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphine, and arylamine, the defined carbon number refers to the total number of carbons in the corresponding group.

[0103] The "carbon number ab" in the statement "R group with substituted or unsubstituted carbon number ab" refers to the carbon number when the R group is unsubstituted, excluding the carbon number of the substituent when the R group is substituted.

[0104] "Substituted" in "substituted or unsubstituted" means that one or more hydrogen atoms are replaced by other atoms or functional groups, and unless otherwise defined, it also includes cases where one or more hydrogen atoms are replaced by groups formed by connecting two or more of the substituents mentioned above.

[0105] "Maximum number of substitutions" refers to the maximum number of hydrogen atoms contained in the group when there are no substituents other than hydrogen.

[0106] The following embodiments are merely for the purpose of understanding the technical invention and should not be regarded as specific limitations of the present invention.

[0107] Unless otherwise stated, the raw materials and reagents used in the following examples are commercially available products or can be prepared by known methods. All solvent ratios, unless otherwise specified, are volume ratios. For example, the eluent ethyl acetate:n-hexane = 1:20, which is a volume ratio.

[0108] Synthesis of compound A2

[0109]

[0110] Synthesis of compound A2-3

[0111] Compound A2-1 (CAS: 149817-62-9, 15.00 g, 48.05 mmol), compound A2-2 (CAS: 2641692-27-3, 11.73 g, 50.45 mmol), tetra(triphenylphosphine)palladium (0.83 g, 0.72 mmol), potassium carbonate (16.60 g, 120.13 mmol), tetrahydrofuran (300 mL), and deionized water (50 mL) were added to a 500 mL three-necked round-bottom flask. The flask was evacuated and purged with nitrogen three times. The system was then heated to 75 °C and reacted for 3 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). Compound A2-1 was completely consumed.

[0112] Cool to room temperature, concentrate under reduced pressure to remove some of the solvent, add ethyl acetate (500 mL), wash three times with deionized water (90 mL * 3), separate the contents, dry-load 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 °C for 1 hour to obtain a white solid, compound A2-3 (15.37 g, purity: 99.35%, yield: 76.18%), mass spectrometry: 420.12 (M+H).

[0113] Synthesis of compound A2-5

[0114] Compound A2-3 (15.00 g, 35.72 mmol), compound A2-4 (9.52 g, 37.51 mmol), tris(dibenzylideneacetone)palladium (0.65 g, 0.71 mmol), 2-dicyclohexylphosphine-2′,4′,6′-triisopropylbiphenyl (0.68 g, 1.43 mmol), potassium acetate (8.76 g, 89.30 mmol), and 1,4-dioxane (350 mL) were added to a 500 mL three-necked round-bottom flask. The flask was evacuated and purged with nitrogen three times. The system was then heated to 100 °C and reacted for 2 hours. The reaction was monitored by TLC (using n-hexane:ethyl acetate = 10:1 as the developing solvent). Compound A2-3 was completely consumed.

[0115] The solution was cooled to 60℃, concentrated under reduced pressure to remove the solvent, and ethyl acetate (500 mL) was added. The solution was washed three times with deionized water (100 mL * 3), separated, and loaded onto a silica gel column using a dry method. The solution was purified by silica gel column chromatography (200-300 mesh silica gel, n-hexane:ethyl acetate = 10:1 as eluent). After elution, the solution was concentrated under reduced pressure at 60℃ for 1 hour to obtain the target compound A2-5 (13.05 g, purity: 99.18%, yield: 71.43%), mass spectrometry: 512.24 (M+H).

[0116] Synthesis of compound A2

[0117] Following the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed. A2-2 is replaced with A2-5, and bromine reacts with borate ester to obtain the target compound A2 (10.14 g, purity: 99.95%, yield: 70.07%). After sublimation purification of 10.14 g of crude compound A2, sublimed pure compound A2 (7.69 g, purity: 99.95%, yield: 75.83%) was obtained, mass spectrometry: 617.24 (M+H).

[0118] 1 H NMR(400MHz, CDCl3)δ8.73(s,2H),8.72–8.67(m,6H),8.62(dd,J=8.4,1.4Hz,4H),8.32(d,J=2.0Hz,1H),7.81–7.76(m,5H),7.63 (dd,J=9.2,1.9Hz,1H),7.54(dd,J=8.1,1.4Hz,2H),7.46(dd,J=8.2,7.1Hz,2H),7.39(d,J=7.3Hz,1H),7.22(dd,J=7.1,4.0,4H).

[0119] Synthesis of compound A37

[0120]

[0121] Synthesis of compound A37-3

[0122] Following the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed. Replace A2-1 with A37-1 (CAS:1036005-64-7) and replace A2-2 with A37-2 (CAS:535934-25-9). React iodine with boric acid to obtain the target compound A37-3 (18.34 g, purity: 99.37%, yield: 77.68%), mass spectrometry: 422.01 (M+H).

[0123] Synthesis of compound A37-5

[0124] Following the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed. Replace A2-1 with A37-3 and A2-2 with A37-4 (CAS: 629644-82-2). React bromine with boric acid to obtain the target compound A37-5 (15.11 g, purity: 99.26%, yield: 70.17%), mass spectrometry: 471.13 (M+H).

[0125] Synthesis of compound A37-6

[0126] Following the synthesis and purification method of compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A37-6 (11.94 g, purity: 99.42%, yield: 72.06%), mass spectrometry: 563.25 (M+H).

[0127] Synthesis of compound A37

[0128] Following the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed. A2-1 is replaced with A37-7 (CAS: 22426-14-8), and A2-2 is replaced with A37-6. The bromine reacts with the borate ester to obtain the target compound A37 (8.72 g, purity: 99.93%, yield: 68.82%). After sublimation purification of 8.72 g of crude compound A37, sublimed pure compound A37 (6.69 g, purity: 99.97%, yield: 76.72%) was obtained, mass spectrometry: 615.22 (M+H).

[0129] 1 H NMR(400MHz, CDCl3) δ9.11(d,J=2.4Hz,1H),9.05(dd,J=3.9,1.7Hz,1H),8.91(dd,J=4.1,1.9Hz,1H),8.75 (s,2H),8.70(dd,J=4.0,1.7Hz,2H),8.62(dd,J=8.3,1.4Hz,2H),8.42(dd,J=8.3,1.7Hz,1H),8.25–8.17(m ,2H),8.13(d,J=2.2Hz,1H),8.01(dd,J=8.5,6.6Hz,2H),7.95(s,2H),7.88(d,J=9.2Hz,1H),7.78(dd,J=8. 5,7.2,2H),7.69(dd,J=8.9,2.3Hz,1H),7.65–7.60(m,2H),7.46(dd,J=7.6,4.1Hz,1H),7.24-7.20(m,2H).

[0130] Synthesis of compound A297

[0131]

[0132] Synthesis of compound A297-3

[0133] Following the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed. Replace A2-1 with A297-1 (CAS:19393-94-3) and A2-2 with A297-2 (CAS:100124-06-9). React iodine with boric acid to obtain the target compound A297-3 (13.64 g, purity: 99.60%, yield: 73.50%), mass spectrometry: 400.91 (M+H).

[0134] Synthesis of compound A297

[0135] Following the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed: A2-1 is replaced with A297-3, and A2-2 is replaced with A37-1. The bromine reacts with boric acid to obtain the target compound A297 (9.17 g, purity: 99.96%, yield: 70.33%). After sublimation purification of 9.17 g of crude compound A297, sublimed pure compound A297 (7.34 g, purity: 99.96%, yield: 80.04%) was obtained, mass spectrometry: 707.25 (M+H).

[0136] 1 H NMR (400MHz, CDCl3) δ8.75(d,J=2.4Hz,1H),8.73(s,2H),8.70(dd,J=4.0,1.7Hz,4H),8.62(dd,J=8.4,1.4Hz,4H),8.37(s,2H ),8.10–8.02(m,2H),7.96–7.91(m,1H),7.81–7.73(m,6H),7.64(dd,J=8.1,2.4Hz,1H),7.52–7.35(m,3H),7.24-7.20(m,4H).

[0137] Synthesis of compound A323

[0138]

[0139] Synthesis of compound A323-2

[0140] Following the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed. Replace A2-2 with A323-1 (CAS: 544678-60-6), and react bromine with boric acid to obtain the target compound A323-2 (17.56 g, purity: 99.38%, yield: 75.36%), mass spectrometry: 420.12 (M+H).

[0141] Synthesis of compound A323-3

[0142] Following the synthesis and purification method of compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A323-3 (13.27, purity: 99.14%, yield: 72.55%), mass spectrometry: 512.24 (M+H).

[0143] Synthesis of compound A323-4

[0144] Following the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed. Replace A2-1 with A37-7 and A2-2 with A323-2, and react bromine with borate ester to obtain the target compound A323-4 (11.35 g, purity: 99.90%, yield: 69.07%), mass spectrometry: 564.21 (M+H).

[0145] Synthesis of compound A323

[0146] Referring to the synthesis and purification method of compound A334-2 below, only the corresponding raw materials need to be changed to obtain the target compound A323 (5.72 g, purity: 99.91%, yield: 49.78%). After sublimation purification of 5.72 g of crude compound A323, sublimed pure compound A323 (3.60 g, purity: 99.90%, yield: 62.93%) was obtained, mass spectrometry: 589.37 (M+H).

[0147] Compounds A17, A29, A40, A46, A70, A90, A115, A138, A189, A217, A257, A298, A304, A319, and A334 were prepared using the same synthesis and purification method as compound A2, with the only difference being that the raw materials used were replaced with those listed in Table 1 below.

[0148] Table 1

[0149]

[0150]

[0151]

[0152]

[0153] The synthesis methods of the relevant intermediates are as follows in the table above:

[0154] Synthesis of intermediate A29-4

[0155]

[0156] Synthesis of compound A29-3

[0157] Following the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed. Replace A2-1 with A29-1 and A2-2 with A29-2 (CAS: 2226739-30-4), and react iodine with boric acid to obtain the target compound A29-3 (18.41g, purity: 99.26%, yield: 73.54%), mass spectrometry: 342.98 (M+H).

[0158] Synthesis of intermediate A29-4

[0159] Following the synthesis and purification method of compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A29-4 (14.28 g, purity: 99.31%, yield: 71.06%), mass spectrometry: 391.16 (M+H).

[0160] Synthesis of intermediate A40-4

[0161]

[0162] Synthesis of compound A40-3

[0163] Following the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed. Replace A2-1 with A40-2 (CAS:774608-49-0) and replace A2-2 with A40-1 (CAS:5720-05-8). React iodine with boric acid to obtain the target compound A40-3 (17.11 g, purity: 99.40%, yield: 70.32%), mass spectrometry: 280.97 (M+H).

[0164] Synthesis of intermediate A40-4

[0165] Following the synthesis and purification method of compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A40-4 (12.84 g, purity: 99.17%, yield: 73.44%), mass spectrometry: 329.14 (M+H).

[0166] Synthesis of intermediate A46-7

[0167]

[0168] Synthesis of compound A46-3

[0169] Following the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed. Replace A2-1 with A46-1 (CAS: 31928-47-9) and replace A2-2 with A46-2 (CAS: 126747-14-6). React bromine-iodine with boric acid to obtain the target compound A46-3 (18.20 g, purity: 99.27%, yield: 74.36%), mass spectrometry: 291.95 (M+H).

[0170] Synthesis of intermediate A46-4

[0171] Following the synthesis and purification method of compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A46-4 (13.92g, purity: 99.22%, yield: 71.85%), mass spectrometry: 340.12 (M+H).

[0172] Synthesis of intermediate A46-7

[0173] Following the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound A46-7 (10.74 g, purity: 99.46%, yield: 74.16%), mass spectrometry: 291.06 (M+H).

[0174] Synthesis of intermediate A70-2

[0175]

[0176] Synthesis of compound A70-1

[0177] Following the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed to obtain the target compound A70-1 (15.30 g, purity: 99.51%, yield: 72.09%), mass spectrometry: 344.09 (M+H).

[0178] Synthesis of intermediate A70-2

[0179] Following the synthesis and purification method of compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A70-2 (11.93g, purity: 99.29%, yield: 76.42%), mass spectrometry: 436.21 (M+H).

[0180] Synthesis of intermediate A90-4

[0181]

[0182] Synthesis of compound A90-3

[0183] Following the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed. Replace A2-1 with A90-1 (CAS: 31928-44-6) and A2-2 with A90-2 (CAS: 2226739-30-4). React iodine with boric acid to obtain the target compound A90-3 (16.71g, purity: 99.44%, yield: 69.52%), mass spectrometry: 267.95 (M+H).

[0184] Synthesis of intermediate A90-4

[0185] Following the synthesis and purification method of compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A90-4 (14.06 g, purity: 99.20%, yield: 75.28%), mass spectrometry: 316.12 (M+H).

[0186] Synthesis of intermediate A115-4

[0187]

[0188] Synthesis of compound A115-3

[0189] Following the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed. Replace A2-1 with A115-1 (CAS:1260393-65-4) and replace A2-2 with A115-2 (CAS:2793402-18-1). React chlorine with boric acid to obtain the target compound A115-3 (13.71 g, purity: 99.34%, yield: 67.49%), mass spectrometry: 547.05 (M+H).

[0190] Synthesis of intermediate A115-4

[0191] Following the synthesis and purification method of compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A115-4 (10.28 g, purity: 99.36%, yield: 76.62%), mass spectrometry: 595.22 (M+H).

[0192] Synthesis of intermediate A138-4

[0193]

[0194] Synthesis of compound A138-3

[0195] Following the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed. Replace A2-1 with A138-2 (CAS: 6560-83-4) and replace A2-2 with A138-1 (CAS: 1217501-18-2). React iodine with boric acid to obtain the target compound A138-3 (15.22 g, purity: 99.47%, yield: 72.50%), mass spectrometry: 317.96 (M+H).

[0196] Synthesis of intermediate A138-4

[0197] Following the synthesis and purification method of compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A138-4 (11.43 g, purity: 99.15%, yield: 73.70%), mass spectrometry: 366.14 (M+H).

[0198] Synthesis of intermediate A304-4

[0199]

[0200] Synthesis of compound A304-3

[0201] Following the synthesis and purification method of compound A2-3, only the corresponding raw materials need to be changed. Replace A2-1 with A304-1 (CAS:148836-41-3) and replace A2-2 with A304-2 (CAS:150255-96-2). React iodine with boric acid to obtain the target compound A304-3 (16.20 g, purity: 99.19%, yield: 76.55%), mass spectrometry: 291.95 (M+H).

[0202] Synthesis of intermediate A304-4

[0203] Following the synthesis and purification method of compound A2-5, only the corresponding raw materials needed to be changed to obtain the target compound A304-4 (13.51 g, purity: 99.35%, yield: 74.53%), mass spectrometry: 340.12.

[0204] Synthesis of intermediate A319-2

[0205]

[0206] Following the synthesis and purification method of compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A319-2 (10.87g, purity: 99.26%, yield: 68.49%), mass spectrometry: 320.16 (M+H).

[0207] Synthesis of intermediate A334-3

[0208]

[0209] Synthesis of compound A334-3

[0210] Compound A334-1 (20.00 g, 74.75 mmol, CAS: 126866-33-9), platinum dioxide (0.64 g, 2.81 mmol), and heavy water (300 mL) were added to a 500 mL pressure-resistant reactor. The reactor was evacuated and purged with argon three times. The temperature was raised to 250 °C and the reaction was carried out for 10 hours.

[0211] Cool to room temperature, add dichloromethane (300 mL), wash three times with deionized water (100 mL * 3), separate the contents, dry-load 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 °C for 1 hour to obtain the target compound A334-2 (11.06 g, purity: 99.36%, yield: 53.68%), mass spectrometry: 275.01 (M+H).

[0212] Synthesis of intermediate A334-4

[0213] Following the synthesis and purification method of compound A2-5, only the corresponding raw materials need to be changed to obtain the target compound A334-4 (8.85g, purity: 99.46%, yield: 72.01%), mass spectrometry: 339.21 (M+H).

[0214] Application example: Fabrication of organic electroluminescent devices

[0215] like Figure 1 The diagram shows a schematic of an organic electroluminescent device, comprising a glass substrate 01, an anode 02, a hole injection layer 03, a first hole transport layer 04, a first electron blocking layer 05, a first light-emitting layer 06, a first electron transport layer 07, an N-type charge generation layer 08, a P-type charge generation layer 09, a second hole transport layer 10, a second electron blocking layer 11, a second light-emitting layer 12, a second electron transport layer 13, an electron injection layer 14, and a cathode 15, stacked sequentially.

[0216] Component fabrication method:

[0217] A glass substrate 01 with an ITO transparent electrode (anode) on its surface is provided, wherein the thickness of the anode is 1000 nm;

[0218] The glass substrate 01 was washed sequentially with deionized water, ethanol, acetone and deionized water, then dried at 80°C and then treated with oxygen plasma for 30 minutes.

[0219] The compound HATCN was vapor-deposited on the surface of the anode 02 to form a hole injection layer 03 with a thickness of 20 nm.

[0220] HTL is deposited on one side of the hole injection layer 03 to form the first hole transport layer 04 with a thickness of 10 nm.

[0221] An EBL is deposited on one side of the first hole transport layer 04 to form a first electron blocking layer 05 with a thickness of 5 nm.

[0222] A host material (BH) and a guest material (BD) are co-deposited on one side of the first electron blocking layer 05 to form a first light-emitting layer 06, wherein the weight ratio of BH to BD is 97:3 and the thickness of the first light-emitting layer 06 is 20nm.

[0223] ET and LiQ are co-deposited on one side of the first light-emitting layer to form a first electron transport layer 07, wherein the weight ratio of ET to LiQ is 1:1 and the thickness of the first electron transport layer 07 is 35nm.

[0224] A heterocyclic compound and a doped material (metal Yb) are co-deposited on one side of the first electron transport layer 07 to form an N-type charge generation layer 08 (N-CGL). The types of heterocyclic compounds in the N-CGL layers of each embodiment and comparative example are shown in Table 2. The weight ratio of the heterocyclic compound to Yb is 95:5, and the thickness of the N-type charge generation layer is 100 nm.

[0225] HATCN was deposited on one side of the N-type charge generation layer 08 to form a P-type charge generation layer 09 with a thickness of 10 nm.

[0226] HTL is deposited on one side of the P-type charge generation layer 09 to form a second hole transport layer 10 with a thickness of 10 nm.

[0227] An EBL is deposited on one side of the second hole transport layer 10 to form a second electron blocking layer 11 with a thickness of 5 nm.

[0228] A host material (BH) and a guest material (BD) are co-deposited on one side surface of the second electron blocking layer 11 to form a second light-emitting layer 12, wherein the weight ratio of BH to BD is 97:3 and the thickness of the second light-emitting layer 12 is 20 nm.

[0229] ET and LiQ are co-deposited on one side of the second light-emitting layer 12 to form a second electron transport layer 13, wherein the weight ratio of ET to LiQ is 1:1 and the thickness of the second electron transport layer 13 is 35nm.

[0230] Yb is deposited on one side of the second electron transport layer 13 to form an electron injection layer 14 with a thickness of 1 nm.

[0231] Ag is vapor-deposited on one side of the electron injection layer 14 to form a cathode 15 with a thickness of 1000 nm, thus obtaining an organic electroluminescent device.

[0232] The structural formulas of HAT-CN, HTL, EBL, BH, BD, ET, LiQ, and comparative compounds 1-6 are as follows:

[0233]

[0234] Comparative compounds

[0235]

[0236] evaluate:

[0237] The fabricated organic electroluminescent device was subjected to device performance testing. A constant current power supply (Keithley 2400) was used to flow a fixed current density through the light-emitting element, and the emission spectrum was measured using a spectroradiometer (CS2000). Simultaneously, at 10 mA / cm²... 2 The IVL (current-voltage-luminance) performance of the device was measured at 50 mA / cm². 2 The lifetime of the LT95 device was tested, and the drift voltage of the device (the difference between the voltage at which the lifetime decays to LT95 and the initial voltage) was also tested.

[0238] The test results are shown in Table 2:

[0239] Table 2

[0240]

[0241] As shown in Table 2, compared with comparative compounds 1-6, the N-CGL layer prepared using the heterocyclic compounds in the embodiments of this invention significantly reduces the device operating voltage when used in series with an organic electroluminescent device, effectively reducing power consumption. Simultaneously, current efficiency and device lifetime are significantly improved, and the drift voltage is lower, indicating higher stability of the device under long-term operating conditions. Introducing specific linking groups into the molecular structure and combining them with a specific terpyridine heterocyclic structure can improve coordination stability with metal ions and allow for fine-tuning of energy levels, thereby reducing the electron injection barrier. Furthermore, as shown in Example 1 and Comparative Example 6, comparative compound 6, due to its sterically hindered benzene linkage, results in elongated bis-terpyridine bond lengths, leading to poor material stability under heat or electroluminescence and a shorter device lifetime. This type of heterocyclic compound, as an N-type charge-generating layer material, is suitable for OLED light-emitting devices and has the potential for application in the AMOLED industry.

Claims

1. A heterocyclic compound, characterized in that, It has the structure shown in equation (1) or equation (2): Ar1 is selected from one of the structures shown in equations (A-1) to (A-4); R1-R6 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 heteroalkyl, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C2-C40 alkynyl, substituted or unsubstituted C3-C40 cycloalkyl, substituted or unsubstituted C3-C40 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C6 0 heteroaryl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C40 alkylsilyl, substituted or unsubstituted C6-C60 arylsilyl, substituted or unsubstituted C1-C40 alkylboryl, substituted or unsubstituted C6-C60 arylboryl, substituted or unsubstituted C6-C60 arylphosphinyl or substituted or unsubstituted C6-C60 arylamino; Where a and c are each independently selected from integers from 0 to 3; b, d, and e are each independently selected from integers from 0 to 4; and f is selected from integers from 0 to 7. L is selected from one of the structures shown in equations (B-1) to (B-6): R8 is 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 or C1-C40 alkoxy. R9 is 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, C5-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. m is selected from integers from 0 to 3; n is selected from integers from 0 to 4; Ar2-Ar6 are each independently selected from substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C3-C60 heteroaryl; In R1-R6 and Ar2-Ar6, the substitution is independently substituted by at least one of deuterium, halogen, cyano, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 hydrocarbon substituted or unsubstituted C6-C30 aryl, C1-C6 hydrocarbon substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions is from monosubstituted to the maximum number of substitutions; The heteroatom in the heteroaryl, heteroalkyl, or heterocycloalkyl group is independently selected from at least one of O, S, N, Se, Si, or Ge.

2. The heterocyclic compound according to claim 1, characterized in that, The heterocyclic compound satisfies at least one of the following conditions: a1) Each of R1-R6 is independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C20 aryl or substituted or unsubstituted C5-C20 heteroaryl; a2) The R8 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl or C3-C20 heterocycloalkyl. a3) R9 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C240 heteroalkyl, C2-C20 alkenyl, C2-20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl or C5-C20 heteroaryl; a4) Each of Ar2-Ar6 is independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl; a5) In R1-R6 and Ar2-Ar6, the substitution is independently substituted by at least one of deuterium, halogen, cyano, C1-C6 alkyl, C3-C12 cycloalkyl, C1-C6 hydrocarbon substituted or unsubstituted C6-C20 aryl, C1-C6 hydrocarbon substituted or unsubstituted C3-C20 heteroaryl, wherein the number of substitutions is from monosubstituted to the maximum number of substitutions.

3. The heterocyclic compound according to claim 1, characterized in that, The heterocyclic compound satisfies at least one of the following conditions: b1) Each of R1-R6 is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 heteroalkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C12 heterocycloalkyl, substituted or unsubstituted C6-C12 aryl or substituted or unsubstituted C5-C12 heteroaryl; b2) R8 and R9 are each independently selected from hydrogen, deuterium, halogen, cyano, C1-C12 alkyl, C1-C12 heteroalkyl, C3-C12 cycloalkyl or C3-C12 heterocycloalkyl; b3) In R1-R6 and Ar2-Ar6, the substitution is independently substituted by at least one of deuterium, halogen, cyano, C1-C6 alkyl, C3-C12 cycloalkyl, C6-C12 aryl, and C3-C12 heteroaryl, wherein the number of substitutions is from monosubstituted to the maximum number of substitutions.

4. The heterocyclic compound according to claim 1, characterized in that, The heterocyclic compound is selected from one of the structures shown in formula (C-1) to formula (C-8):

5. The heterocyclic compound according to claim 1, characterized in that, The L is selected from one of the structures shown in equations (D-1) to (D-10):

6. The heterocyclic compound according to claim 1, characterized in that, Each of the Ar2-Ar6 groups is independently selected from the following groups, or a combination group consisting of at least two of the following groups linked together: substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenyl Fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrene, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, or substituted or unsubstituted benzophenanthryl.

7. The heterocyclic compound according to claim 1, characterized in that, The heterocyclic compound satisfies at least one of the following conditions: c1) R1, R2, R4, and R5 are each independently selected from hydrogen, deuterium, or phenyl; c2) The R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl or substituted or unsubstituted naphthyl, wherein the substitution is independently substituted by at least one of fluorine, methyl, phenyl, wherein the number of substitutions is from monosubstituted to the maximum number of substitutions; c3) The R6 is selected from deuterium, deuterated or unsubstituted phenyl, deuterated or unsubstituted naphthyl or deuterated or unsubstituted pyridyl, wherein the number of deuterations ranges from monosubstituted to the maximum number of substituted. c4) The R8 is selected from hydrogen, deuterium, cyano or methyl; c5) The R9 mentioned is selected from hydrogen; c6) Each of Ar2-Ar5 is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyrene, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophene, wherein the substitution is independently by at least one of deuterium, methyl, phenyl, cyclohexyl, tert-butyl, pyridyl, wherein the number of substitutions is from monosubstituted to the maximum number of substitutions; c7) The Ar6 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, or substituted or unsubstituted dibenzofuranyl; wherein the substitution is independently substituted by at least one of deuterium, fluorine, cyano, methyl, phenyl, or pyridyl, and the number of substitutions is from monosubstituted to the maximum number of substitutions.

8. An organic electroluminescent device, characterized in that, It includes an anode and a cathode, with a functional layer between the cathode and the anode, the functional layer comprising a heterocyclic compound as described in any one of claims 1-7.

9. The organic electroluminescent device according to claim 8, characterized in that, The functional layer consists of a first light-emitting unit, a charge-generating layer, and a second light-emitting unit, stacked sequentially from the anode side to the cathode side. The charge-generating layer contains the heterocyclic compound.

10. The organic electroluminescent device according to claim 9, characterized in that, The charge generation layer consists of an N-type charge generation layer and a P-type charge generation layer stacked sequentially from the first light-emitting unit side to the second light-emitting unit side, wherein the N-type charge generation layer contains the heterocyclic compound.

11. The organic electroluminescent device according to claim 10, characterized in that, The N-type charge generation layer further includes a doping material, which is selected from at least one of alkali metals, alkaline earth metals, or lanthanides. Optionally, the mass percentage of the doped material in the N-type charge generation layer is 0.1%-20%.

12. A photoelectric element, characterized in that, Including the organic electroluminescent device as described in any one of claims 8-11.

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