Condensed ring compound and organic electroluminescent device thereof

Abstract

The invention provides a fused ring compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic electroluminescent materials. When the fused ring compound is used as a covering layer material, the light-emitting efficiency of a device can be effectively improved, the service life of the device can be effectively prolonged, the reflection loss of the device can be reduced, due to the good hole migration rate of the fused ring compound, the carrier balance of the device can be optimized, and the light-emitting efficiency can be effectively improved; and due to the proper triplet state energy level, the material can be used as a main body material with excellent performance. In conclusion, the fused ring compound provided by the invention has development potential in multiple fields of television display, smart phones, wearable intelligent equipment, solid-state lighting and the like.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescent materials technology, specifically to a fused ring compound and its organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs), with their superior characteristics such as high energy efficiency, low driving voltage, fast response speed, and stable emission color, have been successfully applied in various fields including television displays, smartphones, wearable smart devices, and solid-state lighting. With the continuous expansion of OLED technology applications and the rapid increase in market demand, the industry has placed higher demands on the overall performance of OLED devices, especially focusing on achieving synergistic optimization of high efficiency, long lifespan, high color purity, and low power consumption to adapt to high-end applications such as ultra-high-definition displays and flexible displays. Therefore, developing novel and highly efficient organic electroluminescent functional layer materials to drive technological upgrades has crucial research value and application significance.

[0003] From a structural perspective, a typical OLED device mainly consists of core functional layers such as the anode, hole injection layer (HIL), hole transport layer (HTL), emissive layer (EML), electron transport layer (ETL), electron injection layer (EIL), cathode, and capping layer (CP). Among these, the hole transport layer material suffers from low hole mobility, resulting in an imbalance between electron and hole transport and low effective exciton recombination rate, affecting the device's luminous efficiency and lifespan. The emissive layer can include guest and host materials. The host material of the emissive layer suffers from carrier transport imbalance and low energy transfer efficiency, affecting the device's emission color, color purity, and luminous efficiency. The capping layer material has a low refractive index and glass transition temperature, affecting the device's light extraction efficiency and luminous efficiency.

[0004] To address the aforementioned issues, developing a wider variety of hole transport layer materials, light-emitting layer substrate materials, and capping layer materials with superior performance, thereby enabling devices to achieve higher efficiency, longer lifespan, and higher color purity, has become an urgent need for technological research and development in the OLED field. Summary of the Invention

[0005] To address the issue of low performance in existing organic electroluminescent devices, this invention provides a fused ring compound and its organic electroluminescent device.

[0006] This invention provides a fused-ring compound having the structure shown in Formula I.

[0007]

[0008] X is selected from O or S;

[0009] Ring A and ring B are independently selected from the rings shown below:

[0010]

[0011] Furthermore, rings A and B are not selected simultaneously.

[0012] The v is independently selected from C(R2) or N, and when v is bonded to other groups, the v is selected from C atoms;

[0013] The R2 is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, and unsubstituted C6-C30 aryl.

[0014] The z is independently selected from C(R3) or N, and when z is bonded to other groups, the z is selected from C atoms;

[0015] The R3 is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl;

[0016] The Ar is selected from any one of the following groups:

[0017]

[0018] The e is independently selected from CH or N, and when the e is bonded to other groups, the e is selected from C atoms;

[0019] The Q is selected from O, S, N(Rz) or C(RxRy);

[0020] The Q1 is selected from N(Rz) or C(RxRy);

[0021] The Rz is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl groups, and substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl groups.

[0022] The Rx and Ry are independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or Rx and Ry can be interconnected to form one or more substituted or unsubstituted alicyclic groups;

[0023] The ring M is selected from substituted or unsubstituted C3 to C30 alicyclic rings;

[0024] The Rd is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl, or adjacent Rds can be interconnected to form one or more substituted or unsubstituted rings;

[0025] a1 is selected from 0, 1, 2, 3, 4 or 5; a2 is selected from 0, 1, 2, 3 or 4; a3 is selected from 0, 1, 2 or 3; a4 is selected from 0, 1 or 2;

[0026] The L1 is selected from any one of the following groups and combinations thereof: single bond, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloalcoholic group, or groups listed below:

[0027]

[0028] The Rm is independently selected from any one of deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or adjacent Rm may be interconnected to form one or more substituted or unsubstituted rings; Rm1 is independently selected from any one of deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl, or adjacent Rm1 can be interconnected to form one or more substituted or unsubstituted rings;

[0029] The Rm2 and Rm3 are independently selected from any one of deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, or adjacent Rm2 and Rm3 can be interconnected to form one or more substituted or unsubstituted aromatic or alicyclic rings;

[0030] The p 11 The options are selected from 1, 2, 3, or 4; p1 is selected from 0, 1, 2, 3, or 4; p2 is selected from 0, 1, 2, or 3; p3 is selected from 0, 1, or 2; p4 is selected from 0, 1, 2, 3, 4, 5, or 6.

[0031] L2 and L3 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and combinations thereof.

[0032] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic functional layer, wherein the organic functional layer is located between the anode and the cathode or outside either the anode or the cathode, and the organic functional layer comprises any one or more of the fused ring compounds.

[0033] Beneficial effects: This invention provides a fused ring compound, which, when used as a capping layer material, can effectively improve the luminous efficiency and lifespan of the device and reduce the reflection loss of the device. Furthermore, thanks to its good hole migration rate, it can optimize the carrier balance of the device and effectively improve the luminous efficiency. In addition, the suitable triplet energy level also makes it suitable as a high-performance host material. Detailed Implementation

[0034] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only some embodiments of this invention, and not all embodiments. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of this invention.

[0035] In the compounds of this invention, any atom not specified as a particular isotope includes any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances. In this invention, "H," "hydrogen," and "hydrogen atom" refer to isotopes with different numbers of neutrons, including protium, deuterium, and tritium.

[0036] In this specification, "*" indicates a portion connected to another substituent.

[0037] In this specification, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring. For example, Can represent Can represent Can represent And so on.

[0038] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the rings. For example, Can represent Can represent And so on.

[0039] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, or iodine.

[0040] The alkyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The alkyl group can be substituted or unsubstituted. Specific examples may include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, etc., but are not limited thereto.

[0041] The cycloalkyl group described in this invention refers to a monovalent group obtained by removing one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, more preferably 3 to 10 carbon atoms, and particularly preferably 3 to 6 carbon atoms. The cycloalkyl group can be substituted or unsubstituted. The cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, etc.

[0042] 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 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 ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl. 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, substituted or unsubstituted C6-C60 aryl. 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 30 carbon atoms, more preferably 6 to 18, and particularly preferably 6 to 12. Preferably, each R... kThe 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. Preferably, the "substituted or unsubstituted C3-C25 silyl" refers to a silyl group substituted with a substituted or unsubstituted C3-C25 alkyl or aryl group, preferably substituted with 3 alkyl or 3 aryl groups. Examples of “substituted or unsubstituted silyl groups”, especially “substituted or unsubstituted C3 to C25 silyl groups”, may include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, etc.

[0043] The aryl group described in this invention refers to a 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 having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The aryl group can be substituted or unsubstituted. The monocyclic aryl refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl refers to an aryl group containing two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, tetraphenyl, etc., but not limited to this; 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, etc. It includes, but is not limited to, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzo[a]fluorenyl, 9,9'-spirodifluorenyl, etc.

[0044] The heteroaryl group described in this invention refers to a group obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, O, S, N, Si, or P atoms, and preferably have 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, and most preferably 2 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic heteroatom. The heteroaryl group can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. The heteroaryl group can be substituted or unsubstituted. 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, benzo[a]quinolinyl, benzo[a]isoquinolinyl, quinazolinyl, quinoxalinyl, benzo[a] ... Phinyl, o-phenanthroline, naphthidyl, indolyl, benzothiopheneyl, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, dibenzooxazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazoleyl, benzocarbazoleyl, acridineyl, phenoxazinyl, phenthiaazinyl, phenoxthiayl, spirofluorenexanthraceneyl, spirofluorenethixanthraceneyl, etc., but not limited to these.

[0045] The alicyclic hydrocarbons described in this invention refer to cyclic hydrocarbons with aliphatic properties, containing closed carbon rings in the molecule, preferably with 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, even more preferably 3 to 12 carbon atoms, and more preferably 3 to 7 carbon atoms. They can form monocyclic or polycyclic hydrocarbons, and can be saturated or unsaturated alicyclic hydrocarbons. The alicyclic hydrocarbons can be substituted or unsubstituted. Examples of saturated alicyclic hydrocarbons include cyclopropane, cyclobutane, cyclopentane, cyclohexane, and cycloheptane, while examples of unsaturated alicyclic hydrocarbons include cyclopropylene, cyclobutene, cyclopentene, cyclohexene, and cycloheptene, but are not limited thereto. Multiple monocyclic hydrocarbons can also be linked in various ways: two rings in the molecule can share a carbon atom to form a spirocyclic ring; two carbon atoms on a ring can be connected by a carbon bridge to form a bridged ring; several rings can also be interconnected to form a cage-like structure.

[0046] The fused alicyclic and aromatic ring groups described in this invention refer to rings containing one or more aromatic rings and one or more alicyclic rings fused together by sharing two adjacent carbon atoms. The aromatic rings preferably have 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The alicyclic rings preferably have 3 to 30 carbon atoms, more preferably C3 to C18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. The fused alicyclic and aromatic ring groups can be substituted or unsubstituted. Examples include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited thereto.

[0047] The fused cyclic group of alicyclic and heteroaromatic rings mentioned in this invention refers to a monovalent group formed by removing a hydrogen atom after the alicyclic and heteroaromatic rings are fused together. Preferably, it has 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms. Examples include, but not limited to, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenecyclopropyl, dibenzothiophenecyclobutyl, dibenzothiophenecyclopentyl, dibenzothiophenecyclohexyl, dibenzothiophenecycloheptyl, carbazocyclopropyl, carbazocyclobutyl, carbazocyclopentyl, carbazocyclohexyl, carbazocycloheptyl, pyridinocyclopropyl, pyridinocyclobutyl, pyridinocyclopentyl, pyridinocyclohexyl, pyridinobenzocycloheptyl, pyrimidinocyclopropyl, pyrimidinocyclobutyl, pyrimidinocyclopentyl, pyrimidinocyclohexyl, pyrimidinobenzocycloheptyl, etc.

[0048] The arylene group referred to in this invention refers to the general term for the divalent group remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic hydrocarbon molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, preferably having 6 to 30 carbon atoms, more preferably 6 to 22 carbon atoms, even more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Regarding the aforementioned arylene groups, monocyclic arylene groups can be phenylene, etc., but are not limited to these. The arylene group can be substituted or unsubstituted. Polycyclic arylene groups can be biphenylene, terphenylene, tetraphenylene, etc., but are not limited to these. Fused-ring arylene groups can be naphthylene, anthraceneene, phenanthrene, pyrene, fluorene, spirofluorene, triphenylene, perylene, fluorenyl, etc. It includes, but is not limited to, basic, and advanced technologies.

[0049] The heteroaryl group described in this invention refers to the general term for a divalent group formed by removing two hydrogen atoms from the nucleus carbon of an aromatic heterocycle composed of carbon and heteroatoms. The heteroatoms can be one or more of N, O, S, Si, and P, and can be monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. Preferably, it has 2 to 30 carbon atoms, more preferably 2 to 22 carbon atoms, even more preferably 2 to 20 carbon atoms, and most preferably 3 to 12 carbon atoms. The heteroaryl group can be substituted or unsubstituted. Examples may include, but are not limited to, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, thiopheneyl, pyrroloyl, furanyl, pyranyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, carbazolyl, benzocarbazolyl, acridineyl, imoxazanyl, thionazanyl, phenazinyl, phenthiazolyl, phenoxazinyl, indolyl, quinolinyl, isoquinolinyl, benzothiopheneyl, benzofuranyl, dibenzofuranyl, dibenzothiopheneyl, quinoxolinyl, quinoxolinyl, naphthinyl, purineyl, and phenanthrolineyl.

[0050] The fused alicyclic and aromatic ring groups described in this invention refer to fused ring groups of aromatic and aliphatic rings with two linking sites, i.e., divalent groups. Apart from being divalent groups, they are similar to the fused ring groups of aromatic and aliphatic rings described above.

[0051] In this invention, "unsubstituted" in "substituted or unsubstituted" means that the hydrogen atom on the group is not substituted by any substituent; "substituted" means that at least one hydrogen atom on the group is substituted by a substituent, and the position of the substitution is not limited. When multiple hydrogen atoms are substituted by multiple substituents, the multiple substituents may be the same or different.

[0052] 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, cyano, fluorine, halogen atom, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, 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, preferably deuterium, cyano, halogen atom, trifluoromethyl, C1-C12 alkyl, C3-C12 cycloalkyl, C 3–C25 silyl groups, C6–C30 aryl groups, and C2–C30 heteroaryl groups, with specific examples including 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, and triphenylene. The following are some of the following groups: 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, pyrrole, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, pyridinyl, pyrimidinyl, pyrazinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, phenothiazinyl, phenothiazinyl, acridineyl, etc., but not limited to these.

[0053] The "linked ring formation" described in this invention refers to two groups being linked together by chemical bonds and optionally undergoing aromatization. Examples are shown below:

[0054]

[0055] 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.

[0056] This invention provides a fused-ring compound having the structure shown in Formula I.

[0057]

[0058] X is selected from O or S;

[0059] Ring A and ring B are independently selected from the rings shown below:

[0060]

[0061] Furthermore, rings A and B are not selected simultaneously.

[0062] The v is independently selected from C(R2) or N, and when v is bonded to other groups, the v is selected from C atoms;

[0063] The R2 is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, and unsubstituted C6-C30 aryl.

[0064] The z is independently selected from C(R3) or N, and when z is bonded to other groups, the z is selected from C atoms;

[0065] The R3 is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl;

[0066] The Ar is selected from any one of the following groups:

[0067]

[0068] The e is independently selected from CH or N, and when the e is bonded to other groups, the e is selected from C atoms;

[0069] The Q is selected from O, S, N(Rz) or C(RxRy);

[0070] The Q1 is selected from N(Rz) or C(RxRy);

[0071] The Rz is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl groups, and substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl groups.

[0072] The Rx and Ry are independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or Rx and Ry can be interconnected to form one or more substituted or unsubstituted alicyclic groups;

[0073] The ring M is selected from substituted or unsubstituted C3 to C30 alicyclic rings;

[0074] The Rd is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl, or adjacent Rds can be interconnected to form one or more substituted or unsubstituted rings;

[0075] a1 is selected from 0, 1, 2, 3, 4 or 5; a2 is selected from 0, 1, 2, 3 or 4; a3 is selected from 0, 1, 2 or 3; a4 is selected from 0, 1 or 2;

[0076] The L1 is selected from any one of the following groups and combinations thereof: single bond, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloalcoholic group, or groups listed below:

[0077]

[0078] The Rm is independently selected from any one of deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl, or adjacent Rm can be interconnected to form one or more substituted or unsubstituted rings;

[0079] The Rm1 is independently selected from any one of deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, or adjacent Rm1 can be interconnected to form one or more substituted or unsubstituted rings;

[0080] The Rm2 and Rm3 are independently selected from any one of deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, or adjacent Rm2 and Rm3 can be interconnected to form one or more substituted or unsubstituted aromatic or alicyclic rings;

[0081] The p 11 The options are selected from 1, 2, 3, or 4; p1 is selected from 0, 1, 2, 3, or 4; p2 is selected from 0, 1, 2, or 3; p3 is selected from 0, 1, or 2; p4 is selected from 0, 1, 2, 3, 4, 5, or 6.

[0082] L2 and L3 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and combinations thereof.

[0083] Preferably, the Selected from any one of the following groups:

[0084]

[0085] The R2 is selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, or any of the following groups substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, trimethylsilyl, triethylsilyl, tritert-butylsilyl, and triphenylsilyl.

[0086] More preferably, the Selected from any one of the following groups:

[0087]

[0088]

[0089]

[0090] f1 is selected from 0, 1, 2, 3 or 4; f2 is selected from 0, 1, 2, 3, 4, 5 or 6; f3 is selected from 0, 1, 2, 3, 4 or 5; f4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; f5 is selected from 0, 1, 2 or 3; f6 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0091] Preferably, the Selected from any one of the following groups:

[0092]

[0093] The R3 is selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene;

[0094] The n1 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the n2 is selected from 0, 1, 2, or 3; the n3 is selected from 0, 1, 2, 3, 4, 5, or 6; the n4 is selected from 0, 1, or 2; and the n5 is selected from 0, 1, 2, 3, 4, or 5. Preferably, the Ar is selected from any one of the following groups:

[0095]

[0096]

[0097] The Rd is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane. Alkyl, norbornel, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, or two adjacent Rds may be connected to each other to form one or more substituted or unsubstituted rings;

[0098] a1 is selected from 0, 1, 2, 3, 4, or 5; a2 is selected from 0, 1, 2, 3, or 4; a3 is selected from 0, 1, 2, or 3; a4 is selected from 0, 1, or 2; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; a6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a7 is selected from 0, 1, 2, 3, 4, 5, or 6; a8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; a9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; a 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; a 11 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; a 12 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11;

[0099] Preferably, the e is independently selected from CH, or one, two or three e in each group are selected from N, and when the e is bonded to other groups, the e is selected from C atoms.

[0100] Preferably, L1 is selected from single bonds or any of the following groups and combinations thereof:

[0101]

[0102] The Rm is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane. Alkyl, norbornel, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, or two adjacent Rm may be connected to each other to form one or more substituted or unsubstituted rings;

[0103] The Rm1 is independently selected from deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane. The following compounds can be connected to each other to form one or more substituted or unsubstituted rings: alkyl, norbornelalkyl, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracel, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiopheneyl, or two adjacent Rm1s can be connected to each other to form one or more substituted or unsubstituted rings;

[0104] The Rm0 is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene;

[0105] The p 11 The options are selected from 1, 2, 3, or 4; p1 is selected from 0, 1, 2, 3, or 4; p2 is selected from 0, 1, 2, or 3; p3 is selected from 0, 1, or 2; p4 is selected from 0, 1, 2, 3, 4, 5, or 6; p5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; p6 is selected from 0, 1, 2, 3, 4, or 5.

[0106] Preferably, L1 is selected from single bonds or any of the following groups and combinations thereof:

[0107]

[0108] Preferably, L1 is selected from single bonds or any of the following groups and combinations thereof:

[0109]

[0110] Preferably, L2 and L3 are independently selected from single bonds or any of the following groups and combinations thereof:

[0111]

[0112] The s is independently selected from CH or N, and when s is bonded to other groups, the s is selected from C atoms;

[0113] The T is selected from O, S, N(Rw) or C(RhRi);

[0114] The Rw is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl groups, and substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl groups.

[0115] The ring K is selected from substituted or unsubstituted C3 to C30 alicyclic rings;

[0116] The Rh and Ri are independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, or fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or adjacent Rh and Ri can be connected to each other to form substituted or unsubstituted rings;

[0117] The Rn is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or adjacent Rn can be interconnected to form one or more substituted or unsubstituted rings;

[0118] The q1 is selected from 0, 1, 2, 3 or 4; the q2 is selected from 0, 1, 2 or 3; the q3 is selected from 0, 1 or 2; and the q4 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0119] Preferably, the s is independently selected from CH, or one, two or three s in each group are selected from N, and when s is bonded to other groups, the s is selected from C atoms.

[0120] Preferably, in each six-membered ring containing s, at most two or at most one is selected from N.

[0121] Preferably, Rn contains at most two or at most one selected from substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic groups.

[0122] Preferably, L2 and L3 are independently selected from single bonds or any of the following groups and combinations thereof:

[0123]

[0124] The Rn is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane. Alkyl, norbornel, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, or two adjacent Rn may be connected to each other to form one or more substituted or unsubstituted rings;

[0125] The q5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the q6 is selected from 0, 1, 2, 3, 4 or 5.

[0126] Preferably, L2 and L3 are independently selected from single bonds or any of the following groups and combinations thereof:

[0127]

[0128] Preferably, the fused-ring compound is selected from any one of the following structures:

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161] The above lists some specific structural forms of fused ring compounds represented by Formula I in this invention. However, this invention is not limited to these listed chemical structures. Any structure based on the structure shown in Formula I, with substituents defined above, should be included.

[0162] The present invention provides an organic electroluminescent device, comprising an anode, a cathode, and an organic functional layer, wherein the organic functional layer is located between the anode and the cathode or outside either the anode or the cathode, and the organic functional layer comprises any one or more of the fused ring compounds described in the present invention.

[0163] Preferably, the organic functional layer is located outside either the anode or the cathode, and the organic functional layer includes a capping layer, which contains any one or more of the fused ring compounds of the present invention.

[0164] Preferably, the organic functional layer is located between the anode and the cathode, and the organic functional layer includes a hole transport region, a light-emitting layer and an electron transport region. The light-emitting layer is located between the hole transport region and the electron transport region, and the light-emitting layer contains any one or more of the fused ring compounds of the present invention.

[0165] Preferably, the light-emitting layer comprises a host material and a guest material, wherein the host material comprises any one or more of the fused ring compounds described in this invention.

[0166] Preferably, the organic functional layer is located between the anode and the cathode, and the organic functional layer includes a hole transport region, a light-emitting layer and an electron transport region. The hole transport layer region is located between the anode and the light-emitting layer, and the hole transport layer region contains any one or more of the fused ring compounds of the present invention.

[0167] The hole transport region comprises a hole transport layer and an electron blocking layer, wherein the hole transport layer comprises any one or more of the fused ring compounds described in this invention.

[0168] This invention does not particularly limit the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The organic functional layers of the aforementioned organic electroluminescent device and the electrodes on both sides of the device are described below:

[0169] The organic electroluminescent device of the present invention is typically formed on a substrate. The substrate need not change during the formation of electrodes and organic layers; for example, substrates made of glass, plastic, polymer films, silicon, etc.

[0170] The anode material described in this invention preferably uses a material with a high energy function, which improves hole injection efficiency. The anode material that can be used in this invention is selected from the following: indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO) or any combination thereof, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) or any combination thereof. The anode can have a single-layer structure or a multilayer structure including two or more layers. For example, the anode can have a single-layer structure of Al or a three-layer structure of ITO / Ag / ITO, but is not limited thereto.

[0171] The hole injection layer described in this invention preferably uses a material with good hole-accepting ability. Specific examples of materials that can be used in the hole injection layer of this invention may include silver oxide, vanadium oxide, tungsten oxide, copper oxide, phthalocyanine compounds, benzidine compounds, phenazine compounds, etc., but are not limited thereto.

[0172] The hole transport layer material described in this invention is preferably a material with high hole mobility. It can be selected from any one or more of the following structures: N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-di(naphthyl-2-yl)-N,N'-di(phenyl)biphenyl-4,4'-diamine (β-NPB), 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), carbazole derivatives, triarylamine derivatives, biphenyl diamine derivatives, fluorene derivatives, stilbene derivatives, quinacridone compounds, anthraquinone compounds, polyaniline, polythiophene, etc., or the fused ring compounds described in this invention, but are not limited thereto.

[0173] The electron blocking layer material described in this invention is preferably a material that has the property of preventing electrons from passing through the light-emitting layer. Specific examples may include materials such as triarylamine derivatives, spirofluorene derivatives, furan derivatives, etc., such as N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), but are not limited thereto.

[0174] The light-emitting layer material of this invention includes a host material and a dopant material. The host material of the light-emitting layer needs to have bipolar charge transport properties and suitable energy levels, and is selected from 4,4'-bis(9-carbazole)biphenyl (CBP), 9,10-bis(2-naphthyl)anthracene (ADN), 9,9'-(1,3-phenyl)bis-9H-carbazole (mCP), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 9,10-bis(1-naphthyl)anthracene (α-AND), N,N'-bis-(1-naphthyl)-N,N'-diphenyl-[1,1':4',1”:4”,1”'-tetraphenyl]-4,4”'-diamino (4PNPB), 1,3,5-tris(9-carbazole)benzene (TCP), etc., or the fused ring compounds of this invention, but are not limited thereto.

[0175] The light-emitting layer doping materials of this invention are classified into blue light-emitting materials, green light-emitting materials, and red light-emitting materials. The light-emitting layer doping materials can be simple fluorescent or phosphorescent materials, or a combination of fluorescent and phosphorescent materials, selected from, but not limited to, 2,5,8,11-tetratert-butylperylene (TBPe), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (BDAVBi), bis(4,6-difluorophenylpyridine-C2,N)pyridinecarboxylated iridium (FIrpic), tris(2-phenylpyridine)iridium (Ir(ppy)3), bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), tris[1-phenylisoquinoline-C2,N]iridium(III) (Ir(piq)3), bis(1-phenylisoquinoline)(acetylacetonate)iridium (Ir(piq)2(acac)).

[0176] The hole blocking layer of this invention preferably uses a material with strong hole blocking capability and suitable HOMO / LUMO energy levels. The hole blocking layer material of this invention can be selected from any one or more of the following structures: phenanthroline derivatives, rare earth derivatives, imidazole derivatives, oxazole derivatives, oxadiazole derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, diazanphenanthrene derivatives, azirbenzene derivatives, anthrone derivatives, etc., but is not limited thereto.

[0177] The electron transport layer material described in this invention is preferably a material with high electron mobility. It can be selected from any one or more of the following structures: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), tris(8-hydroxyquinoline)aluminum(III) (Alq3), etc., but is not limited thereto.

[0178] The electron injection layer material described in this invention is preferably a material with a small barrier difference to the adjacent organic layer material. Specific examples may include: alkali metal compounds (such as lithium oxide, lithium fluoride, cesium carbonate, cesium fluoride, cesium 8-hydroxyquinoline, 8-hydroxyquinoline aluminum), organometallic salts (metal acetate, metal benzoate, or metal stearate), molybdenum trioxide, aluminum, etc., but are not limited to these.

[0179] The cathode material of the present invention preferably uses a material with a low work function that can promote electron injection into the organic layer, thereby reducing the electron injection barrier. It can be selected from any one or more of the following materials: Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds thereof, or mixtures thereof (e.g., mixtures of Ag and Mg), but is not limited thereto.

[0180] The capping layer described in this invention is provided on the outside of either the anode or the cathode electrode, and preferably uses a material that can improve the internal optical coupling efficiency of the device. It can be selected from any one or more of the following structures: arylamine derivatives, biscarbazole derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, triazole derivatives, benzofuran derivatives, diamine derivatives, porphyrin derivatives, phthalocyanine derivatives, etc., or the fused-ring compounds described in this invention, but are not limited thereto.

[0181] The present invention does not impose any special restrictions on the thickness of each organic layer of the organic electroluminescent device; thicknesses commonly used in the field can be adopted.

[0182] The organic electroluminescent device of the present invention can be applied using any one of the following methods: vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer, electrospray coating, slot coating, and dip coating.

[0183] The organic electroluminescent device of the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0184] The organic electroluminescent device described in this invention can be widely used in panel displays, lighting sources, flexible OLEDs, electronic paper, organic solar cells, organic photosensitive materials or organic thin-film transistors, signs, signal lights and other fields.

[0185] This invention provides a method for preparing compounds represented by Formula I, which is carried out via a carbon-nitrogen coupling reaction well known in the art. However, the preparation method of this invention is not limited to this, and the structure of Formula I can be prepared by the reaction route shown below:

[0186]

[0187] Among them, Xa, Xb, Xc, and Xd may be the same or different from each other, and are selected from any one of Cl, Br, and I; the limitations of A, B, L1, L2, L3, Ar, and z are the same as those described above.

[0188] The above-mentioned substituents can be bonded by methods known in the art, and the type and position or number of substituents can be changed according to techniques known in the art.

[0189] The invention is explained in more detail through the following examples, but is not intended to limit the invention. Based on this description, those skilled in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the entire scope disclosed without inventive effort.

[0190] Preparation and characterization of compounds

[0191] Description of raw materials, reagents, and characterization equipment:

[0192] The present invention does not impose any particular restrictions on the source of the raw materials and reagents used in the following embodiments; they can be commercially available products or prepared using methods well known to those skilled in the art. All raw materials and reagents used in the present invention are of reagent purity.

[0193] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0194] Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0195] Synthesis Example 1: Preparation of b-141

[0196]

[0197] Preparation of intermediate b-141:

[0198] Under nitrogen protection, e-141 (28.72 g, 80.00 mmol), f-141 (27.54 g, 80.00 mmol), and K2CO3 (22.11 g, 160.00 mmol) were dissolved in 360 mL of toluene / ethanol / water (2:1:1) and Pd(dppf)Cl2 (1.17 g, 1.6 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 6 h. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the obtained solid with toluene / ethanol = 5:1 to give intermediate b-141 (29.84 g, yield 83%); HPLC purity ≥ 99.87%. Mass spectrometry m / z: 448.0474 (theoretical value: 448.0463).

[0199] Using the method described above, the following intermediates were synthesized by equimolar substitution of raw material e-141 and raw material f-141:

[0200]

[0201] Synthesis Example 2: Preparation of Compound 3

[0202]

[0203] Preparation of intermediate A-3:

[0204] Under nitrogen protection, toluene (300 mL), a-3 (10.96 g, 50.00 mmol), b-3 (14.86 g, 50.00 mmol), sodium tert-butoxide (9.61 g, 100.00 mmol), palladium acetate (0.17 g, 0.75 mmol), and tri-tert-butylphosphine (0.61 g, 3.00 mmol) were added to a reaction flask and refluxed for 3.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The solution was recrystallized from toluene:ethanol (5:1) to give A-3 (17.86 g, yield 82%). The purity of the solid was ≥99.88% as determined by HPLC. Mass spectrometry m / z: 435.1632 (theoretical value: 435.1623).

[0205] Preparation of compound 3:

[0206] Under nitrogen protection, toluene (250 mL), A-3 (13.07 g, 30.00 mmol), c-3 (8.43 g, 30.00 mmol), sodium tert-butoxide (5.77 g, 60.00 mmol), tris(dibenzylacetone) dipalladium (0.27 g, 0.30 mmol), and X-phos (0.29 g, 0.60 mmol) were added to a reaction flask and refluxed for 4 hours. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with chloroform. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was recrystallized from toluene to give compound 3 (14.69 g, yield 77%). The purity of the solid was ≥99.97% as determined by HPLC. Mass spectrometry m / z: 635.2263 (theoretical value: 635.2249). Theoretical elemental content (%) C 48 H 29 NO: C, 90.68; H, 4.60; N, 2.20. Measured elemental content (%): C, 90.72; H, 4.63; N, 2.15.

[0207] Synthesis Example 3: Preparation of Compound 8

[0208]

[0209] According to the preparation method in Synthesis Example 2, b-3 was replaced with an equimolar amount of b-8 to obtain compound 8 (14.30 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 635.2261 (theoretical value: 635.2249). Theoretical elemental content (%) C 48 H 29 NO: C, 90.68; H, 4.60; N, 2.20. Measured elemental content (%): C, 90.71; H, 4.64; N, 2.17.

[0210] Synthesis Example 4: Preparation of Compound 16

[0211]

[0212] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-16 to obtain compound 16 (12.26 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 559.1927 (theoretical value: 559.1936). Theoretical elemental content (%) C 42 H 25 NO: C, 90.14; H, 4.50; N, 2.50. Measured elemental content (%): C, 90.12; H, 4.55; N, 2.48.

[0213] Synthesis Example 5: Preparation of Compound 35

[0214]

[0215] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-26, b-3 was replaced with an equimolar amount of b-26, and c-3 was replaced with an equimolar amount of c-26, yielding compound 26 (15.83 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 712.2523 (theoretical value: 712.2515). Theoretical elemental content (%) C 53 H 32 N₂O: C, 89.30; H, 4.52; N, 3.93. Measured elemental content (%): C, 89.33; H, 4.54; N, 3.91.

[0216] Synthesis Example 6: Preparation of Compound 44

[0217]

[0218] According to the preparation method in Synthesis Example 2, b-3 was replaced with an equimolar amount of b-44, and c-3 was replaced with an equimolar amount of c-44 to obtain compound 44 (15.40 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 712.2526 (theoretical value: 712.2515). Theoretical elemental content (%) C 53 H 32 N₂O: C, 89.30; H, 4.52; N, 3.93. Measured elemental content (%): C, 89.32; H, 4.53; N, 3.91.

[0219] Synthesis Example 7: Preparation of Compound 60

[0220]

[0221] According to the preparation method in Example 2, a-3 was replaced with an equimolar amount of a-60 to obtain compound 60 (15.38 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 711.2569 (theoretical value: 711.2562). Theoretical elemental content (%) C 54 H 33 NO: C, 91.11; H, 4.67; N, 1.97. Measured elemental content (%): C, 91.14; H, 4.68; N, 1.95.

[0222] Synthesis Example 8: Preparation of Compound 77

[0223]

[0224] According to the preparation method in Example 2, a-3 was replaced with an equimolar amount of a-77, and b-3 was replaced with an equimolar amount of b-77, yielding compound 77 (13.67 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 641.1822 (theoretical value: 641.1813). Theoretical elemental content (%) C 48 H 29 NOS: C, 86.33; H, 4.38; N, 2.10. Measured elemental content (%): C, 86.30; H, 4.35; N, 2.13.

[0225] Synthesis Example 9: Preparation of Compound 91

[0226]

[0227] According to the preparation method in Example 2, a-3 was replaced with an equimolar amount of a-77, and c-3 was replaced with an equimolar amount of c-26, yielding compound 91 (14.06 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 641.1820 (theoretical value: 641.1813). Theoretical elemental content (%) C 46 H 27 NOS: C, 86.09; H, 4.24; N, 2.18. Measured elemental content (%): C, 86.11; H, 4.25; N, 2.16.

[0228] Synthesis Example 10: Preparation of Compound 131

[0229]

[0230] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-131 to obtain compound 131 (13.56 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 645.2053 (theoretical value: 645.2064). Theoretical elemental content (%) C 46 H 23 D4NOS: C, 85.55; H, 4.84; N, 2.17. Measured elemental content (%): C, 85.57; H, 4.86; N, 2.14.

[0231] Synthetic Example 11: Preparation of Compound 141

[0232]

[0233] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-77, and b-3 was replaced with an equimolar amount of b-141 to obtain compound 141 (16.44 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 793.2446 (theoretical value: 793.2439). Theoretical elemental content (%) C 58 H 35 NOS: C, 87.74; H, 4.44; N, 1.76. Measured elemental content (%): C, 87.77; H, 4.42; N, 1.78.

[0234] Synthetic Example 12: Preparation of Compound 174

[0235]

[0236] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-174, and b-3 was replaced with an equimolar amount of b-174, yielding compound 174 (14.36 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 703.2269 (theoretical value: 703.2260). Theoretical elemental content (%) C 50 H 29 N3O2: C, 85.33; H, 4.15; N, 5.97. Measured elemental content (%): C, 85.32; H, 4.14; N, 5.99.

[0237] Synthesis Example 13: Preparation of Compound 192

[0238]

[0239] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-192 to obtain compound 192 (13.99 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 675.2189 (theoretical value: 675.2198). Theoretical elemental content (%) C 50 H 29 NO2: C, 88.87; H, 4.33; N, 2.07. Measured elemental content (%): C, 88.89; H, 4.34; N, 2.06.

[0240] Synthesis Example 14: Preparation of Compound 213

[0241]

[0242] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-213, and b-3 was replaced with an equimolar amount of b-213, yielding compound 213 (12.97 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 626.2007 (theoretical value: 626.1994). Theoretical elemental content (%) C 45 H 26 N2O2: C, 86.24; H, 4.18; N, 4.47. Measured elemental content (%): C, 86.27; H, 4.16; N, 4.45.

[0243] Synthesis Example 15: Preparation of Compound 240

[0244]

[0245] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-240, and b-3 was replaced with an equimolar amount of b-240, yielding compound 240 (17.34 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 802.2630 (theoretical value: 802.2620). Theoretical elemental content (%) C 59 H 34 N2O2: C, 88.26; H, 4.27; N, 3.49. Measured elemental content (%): C, 88.21; H, 4.25; N, 3.47.

[0246] Synthetic Example 16: Preparation of Compound 316

[0247]

[0248] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-316, and b-3 was replaced with an equimolar amount of b-316 to obtain compound 316 (13.64 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 649.2052 (theoretical value: 649.2042). Theoretical elemental content (%) C 48 H 27 NO2: C, 88.73; H, 4.19; N, 2.16. Measured elemental content (%): C, 88.71; H, 4.23; N, 2.19.

[0249] Synthesis Example 17: Preparation of Compound 396

[0250]

[0251] According to the preparation method in Example 2, a-3 was replaced with an equimolar amount of a-396 to obtain compound 396 (14.03 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 649.2054 (theoretical value: 649.2042). Theoretical elemental content (%) C 48 H 27 NO2: C, 88.73; H, 4.19; N, 2.16. Measured elemental content (%): C, 88.75; H, 4.17; N, 2.17.

[0252] Synthesis Example 18: Preparation of Compound 451

[0253]

[0254] According to the preparation method in Example 2, a-3 was replaced with an equimolar amount of a-451 to obtain compound 451 (13.18 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 636.2193 (theoretical value: 636.2202). Theoretical elemental content (%) C 47 H 28 N₂O: C, 88.66; H, 4.43; N, 4.40. Measured elemental content (%): C, 88.64; H, 4.45; N, 4.41.

[0255] Synthesis Example 19: Preparation of Compound 497

[0256]

[0257] According to the preparation method in Example 2, a-3 was replaced with an equimolar amount of a-497, and b-3 was replaced with an equimolar amount of b-497 to obtain compound 497 (10.85 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 509.1791 (theoretical value: 509.1780). Theoretical elemental content (%) C 38 H 23 NO: C, 89.56; H, 4.55; N, 2.75. Measured elemental content (%): C, 89.57; H, 4.52; N, 2.78.

[0258] Synthesis Example 20: Preparation of Compound 511

[0259]

[0260] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-511 to obtain compound 511 (12.76 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 590.2418 (theoretical value: 590.2406). Theoretical elemental content (%) C 44 H 22 D5NO: C, 89.46; H, 5.46; N, 2.37. Measured elemental content (%): C, 89.44; H, 5.47; N, 2.39.

[0261] Synthesis Example 21: Preparation of Compound 512

[0262]

[0263] According to the preparation method in Example 2, a-3 was replaced with an equimolar amount of a-512 to obtain compound 512 (13.09 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 641.2705 (theoretical value: 641.2719). Theoretical elemental content (%) C 48 H 35 NO: C, 89.83; H, 5.50; N, 2.18. Measured elemental content (%): C, 89.86; H, 5.51; N, 2.14.

[0264] Synthesis Example 22: Preparation of Compound 524

[0265]

[0266] According to the preparation method in Example 2, a-3 was replaced with an equimolar amount of a-524 to obtain compound 524 (14.20 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 685.2415 (theoretical value: 685.2406). Theoretical elemental content (%) C 52 H 31 NO: C, 91.07; H, 4.56; N, 2.04. Measured elemental content (%): C, 91.04; H, 4.57; N, 2.08.

[0267] Synthesis Example 23: Preparation of Compound 552

[0268]

[0269] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-552, and b-3 was replaced with an equimolar amount of b-552, yielding compound 552 (15.01 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 735.2577 (theoretical value: 735.2562). Theoretical elemental content (%) C 56 H 33 NO: C, 91.40; H, 4.52; N, 1.90. Measured elemental content (%): C, 91.46; H, 4.49; N, 1.86.

[0270] Synthesis Example 24: Preparation of Compound 562

[0271]

[0272] According to the preparation method in Example 2, a-3 was replaced with an equimolar amount of a-562 to obtain compound 562 (13.31 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 633.2078 (theoretical value: 633.2093). Theoretical elemental content (%) C 48 H 27 NO: C, 90.97; H, 4.29; N, 2.21. Measured elemental content (%): C, 91.02; H, 4.31; N, 2.17.

[0273] Synthesis Example 25: Preparation of Compound 586

[0274]

[0275] According to the preparation method in Example 2, a-3 was replaced with an equimolar amount of a-586 to obtain compound 586 (13.05 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 639.2574 (theoretical value: 639.2562). Theoretical elemental content (%) C 48 H 33 NO: C, 90.11; H, 5.20; N, 2.19. Measured elemental content (%): C, 90.15; H, 5.22; N, 2.16.

[0276] Synthesis Example 26: Preparation of Compound 599

[0277]

[0278] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-599 to obtain compound 599 (14.78 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 674.2347 (theoretical value: 674.2358). Theoretical elemental content (%) C 50 H 30 N2O: C, 89.00; H, 4.48; N, 4.15. Measured elemental content (%): C, 88.98; H, 4.47; N, 4.16.

[0279] Synthesis Example 27: Preparation of Compound 620

[0280]

[0281] According to the preparation method in Synthesis Example 2, b-3 was replaced with an equimolar amount of b-620, and c-3 was replaced with an equimolar amount of c-620 to obtain compound 620 (14.08 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 651.2011 (theoretical value: 651.2021). Theoretical elemental content (%) C 48 H 29 NS: C, 88.45; H, 4.48; N, 2.15. Measured elemental content (%): C, 88.49; H, 4.46; N, 2.17.

[0282] Synthesis Example 28: Preparation of Compound 631

[0283]

[0284] According to the preparation method in Synthesis Example 2, b-3 was replaced with an equimolar amount of b-631, and c-3 was replaced with an equimolar amount of c-620, yielding compound 631 (14.93 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 731.2599 (theoretical value: 731.2585). Theoretical elemental content (%) C 54 H 29 D4NS: C, 88.61; H, 5.09; N, 1.91. Measured elemental content (%): C, 88.66; H, 5.07; N, 1.92.

[0285] Synthesis Example 29: Preparation of Compound 692

[0286]

[0287] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-692, and b-3 was replaced with an equimolar amount of b-620, yielding compound 692 (13.84 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 658.1529 (theoretical value: 658.1537). Theoretical elemental content (%) C 45 H 26 N2S2: C, 82.04; H, 3.98; N, 4.25. Measured elemental content (%): C, 82.07; H, 3.99; N, 4.22.

[0288] Synthesis Example 30: Preparation of Compound 695

[0289]

[0290] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-695, and b-3 was replaced with an equimolar amount of b-620, yielding compound 695 (16.07 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 733.1881 (theoretical value: 733.1898). Theoretical elemental content (%) C 52 H 31 NS2: C, 85.10; H, 4.26; N, 1.91. Measured elemental content (%): C, 85.14; H, 4.24; N, 1.87.

[0291] Synthesis Example 31: Preparation of Compound 732

[0292]

[0293] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-174, b-3 was replaced with an equimolar amount of b-620, and c-3 was replaced with an equimolar amount of c-732, yielding compound 732 (16.91 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 793.2452 (theoretical value: 793.2439). Theoretical elemental content (%) C 58 H 35 NOS: C, 87.74; H, 4.44; N, 1.76. Measured elemental content (%): C, 87.72; H, 4.39; N, 1.79.

[0294] Synthesis Example 32: Preparation of Compound 737

[0295]

[0296] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-174, b-3 was replaced with an equimolar amount of b-620, and c-3 was replaced with an equimolar amount of c-737, yielding compound 737 (16.91 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 793.2456 (theoretical value: 793.2439). Theoretical elemental content (%) C 58 H 35 NOS: C, 87.74; H, 4.44; N, 1.76. Measured elemental content (%): C, 87.78; H, 4.42; N, 1.79.

[0297] Synthesis Example 33: Preparation of Compound 758

[0298]

[0299] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-758, and b-3 was replaced with an equimolar amount of b-620, yielding compound 758 (13.33 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 643.1728 (theoretical value: 643.1718). Theoretical elemental content (%) C 44 H 25 N3OS: C, 82.09; H, 3.91; N, 6.53. Measured elemental content (%): C, 82.06; H, 3.94; N, 6.51.

[0300] Synthesis Example 34: Preparation of Compound 778

[0301]

[0302] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-778, and b-3 was replaced with an equimolar amount of b-620, yielding compound 778 (13.84 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 658.1545 (theoretical value: 658.1537). Theoretical elemental content (%) C 45 H 26 N2S2: C, 82.04; H, 3.98; N, 4.25. Measured elemental content (%): C, 82.01; H, 3.96; N, 4.28.

[0303] Synthesis Example 35: Preparation of Compound 870

[0304]

[0305] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-870, b-3 was replaced with an equimolar amount of b-620, and c-3 was replaced with an equimolar amount of c-870, yielding compound 870 (15.48 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 747.2041 (theoretical value: 747.2054). Theoretical elemental content (%) C 53 H 33 NS2: C, 85.11; H, 4.45; N, 1.87. Measured elemental content (%): C, 85.06; H, 4.43; N, 1.88.

[0306] Synthesis Example 36: Preparation of Compound 871

[0307]

[0308] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-871, and b-3 was replaced with an equimolar amount of b-620, yielding compound 871 (14.52 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 681.1569 (theoretical value: 681.1585). Theoretical elemental content (%) C 48 H 27 NS2: C, 84.55; H, 3.99; N, 2.05. Measured elemental content (%): C, 84.51; H, 4.02; N, 2.03.

[0309] Synthesis Example 37: Preparation of Compound 929

[0310]

[0311] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-929, and b-3 was replaced with an equimolar amount of b-620, yielding compound 929 (13.34 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 653.1943 (theoretical value: 653.1926). Theoretical elemental content (%) C 46 H 27 N3S: C, 84.51; H, 4.16; N, 6.43. Measured elemental content (%): C, 84.54; H, 4.18; N, 6.40.

[0312] Synthesis Example 38: Preparation of Compound 945

[0313]

[0314] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-945, and b-3 was replaced with an equimolar amount of b-620, yielding compound 945 (13.66 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 669.1747 (theoretical value: 669.1738). Theoretical elemental content (%) C 45 H 26 F3NS: C, 80.70; H, 3.91; N, 2.09. Measured elemental content (%): C, 80.66; H, 3.93; N, 2.08.

[0315] Synthesis Example 39: Preparation of Compound 947

[0316]

[0317] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-947, and b-3 was replaced with an equimolar amount of b-620, yielding compound 947 (13.55 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 673.2271 (theoretical value: 673.2259). Theoretical elemental content (%) C 47 H 35 NSSi: C, 83.76; H, 5.23; N, 2.08. Measured elemental content (%): C, 83.79; H, 5.22; N, 2.11.

[0318] Synthesis Example 40: Preparation of Compound 948

[0319]

[0320] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-948, and b-3 was replaced with an equimolar amount of b-948, yielding compound 948 (14.79 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 735.2944 (theoretical value: 735.2960). Theoretical elemental content (%) C 54 H 41 NS: C, 88.13; H, 5.62; N, 1.90. Measured elemental content (%): C, 88.15; H, 5.61; N, 1.92.

[0321] Synthesis Example 41: Preparation of Compound 1301

[0322]

[0323] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-962, and b-3 was replaced with an equimolar amount of b-620, yielding compound 962 (13.33 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 625.1879 (theoretical value: 625.1864). Theoretical elemental content (%) C 46 H 27 NS: C, 88.29; H, 4.35; N, 2.24. Measured elemental content (%): C, 88.30; H, 4.37; N, 2.21.

[0324] Synthesis Example 42: Preparation of Compound 984

[0325]

[0326] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-984, and b-3 was replaced with an equimolar amount of b-620, yielding compound 984 (16.09 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 765.2476 (theoretical value: 765.2490). Theoretical elemental content (%) C 57 H 35 NS: C, 89.38; H, 4.61; N, 1.83. Measured elemental content (%): C, 89.35; H, 4.57; N, 1.88.

[0327] Synthesis Example 43: Preparation of Compound 991

[0328]

[0329] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-316, and b-3 was replaced with an equimolar amount of b-991, yielding compound 991 (12.97 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 608.2461 (theoretical value: 608.2450). Theoretical elemental content (%) C 44 H 16 D9NO2: C, 86.82; H, 5.63; N, 2.30. Measured elemental content (%): C, 86.85; H, 5.60; N, 2.28.

[0330] Synthesis Example 44: Preparation of Compound 1032

[0331]

[0332] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-1032, and b-3 was replaced with an equimolar amount of b-620, yielding compound 1032 (15.29 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 707.1753 (theoretical value: 707.1741). Theoretical elemental content (%) C 50 H 29 NS2: C, 84.83; H, 4.13; N, 1.98. Measured elemental content (%): C, 84.81; H, 4.08; N, 2.02.

[0333] Device Examples

[0334] The organic materials used in the device fabrication examples were all purified by sublimation, with a purity of over 99.99%. The ITO glass substrates and ITO / Ag / ITO glass substrates used in the device fabrication examples were purchased commercially.

[0335] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrophotometer. The device prepared according to this invention was tested at atmospheric pressure and room temperature at a current density of 10 mA / cm². 2 The luminous efficiency and driving voltage were measured. Using McScience's M6000 OLED lifetime testing system, the lifetime (brightness decaying to 95% of initial brightness) of the device prepared in this invention was tested at atmospheric pressure and room temperature. The current density during the test was 10 mA / cm². 2 .

[0336] [Device Example 1]

[0337] First, the ITO / Ag / ITO substrate was ultrasonically cleaned three times in distilled water for 15 minutes each time. After the distilled water cleaning was completed, it was ultrasonically cleaned in sequence with solvents such as isopropanol, acetone, and methanol for 10 minutes each time. After the cleaning was completed, it was dried at 120°C.

[0338] An organic electroluminescent device was fabricated by vacuum evaporation on a pre-cleaned ITO / Ag / ITO substrate, sequentially depositing the following layers: hole injection layer HI-1:P-1 = 97:3 (mass ratio, 20 nm); hole transport layer HT1-1 (100 nm); electron blocking layer EB-1 (35 nm); light-emitting layer GH-1:GD = 97:3 (mass ratio, 30 nm); electron transport layer ET-1:Liq = 1:1 (mass ratio, 35 nm); electron injection layer LiF (0.8 nm); cathode Mg:Ag = 1:9 (mass ratio, 12 nm); and capping layer compound 3 (80 nm).

[0339]

[0340] [Device Examples 2-43]

[0341] Compounds 8, 16, 26, 29, 60, 77, 91, 131, 141, 174, 192, 213, 240, 316, 396, 451, 497, 511, 512, 524, 552, 562, 586, 599, 620, 631, 692, 695, 732, 737, 758, 778, 870, 871, 929, 945, 947, 948, 962, 984, 991, and 1032 of this invention were used to replace compound 3 in device example 1 as the capping layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 1.

[0342] [Comparative Device Examples 1-2]

[0343] Comparative compound 1 and comparative compound 2 were used to replace compound 3 in device example 1 as the capping material, and the organic electroluminescent device was prepared by the same preparation method as device example 1.

[0344] The luminescence characteristics test results of the organic electroluminescent devices obtained in Embodiments 1-43 of the present invention and Comparative Embodiments 1-2 are shown in Table 1 below.

[0345]

[0346]

[0347] As can be seen from the data in Table 1, applying the fused ring compound described in this invention as a capping material in organic electroluminescent devices can effectively improve the luminous efficiency and lifespan of the devices, and reduce the reflection loss of the devices.

[0348] [Device Example 44]

[0349] First, the ITO substrate was ultrasonically cleaned three times in distilled water for 15 minutes each time. After the distilled water cleaning was completed, it was ultrasonically cleaned in sequence with solvents such as isopropanol, acetone, and methanol for 10 minutes each time. After the cleaning was completed, it was dried at 120°C.

[0350] An organic electroluminescent device was fabricated by vacuum evaporation on a cleaned ITO substrate, consisting of a hole injection layer HI-1:P-1 = 97:3 (25 nm); a first hole transport layer HT1-1 (90 nm); a light-emitting layer compound 3:RH-1:RD-1 = 46:46:8 (mass ratio, 35 nm); an electron transport layer ET-2:Liq = 1:1 (mass ratio, 35 nm); an electron injection layer LiF (1.0 nm); and a cathode Al (100 nm).

[0351]

[0352] [Device Examples 45-86]

[0353] Compounds 8, 16, 26, 29, 60, 77, 91, 131, 141, 174, 192, 213, 240, 316, 396, 451, 497, 511, 512, 524, 552, 562, 586, 599, 620, 631, 692, 695, 732, 737, 758, 778, 870, 871, 929, 945, 947, 948, 962, 984, 991, and 1032 of this invention were used to replace compound 3 in device example 44 as the main material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 44.

[0354] [Comparative Device Examples 3-4]

[0355] Comparative compound 3 and comparative compound 4 were used to replace compound 3 in device example 44 as the main material. Otherwise, organic electroluminescent devices were prepared by the same preparation method as device example 44.

[0356] The luminescence characteristics test results of the organic electroluminescent devices obtained in Examples 44-86 and Comparative Examples 3-4 of the present invention are shown in Table 2 below.

[0357]

[0358] As can be seen from the data in Table 2, the fused ring compound described in this invention, when used as the main material of the light-emitting layer in organic electroluminescent devices, has a suitable triplet energy level and can effectively improve the light-emitting effect of the device.

[0359] [Device Example 87]

[0360] First, the ITO substrate was ultrasonically cleaned three times in distilled water for 15 minutes each time. After the distilled water cleaning was completed, it was ultrasonically cleaned in sequence with solvents such as isopropanol, acetone, and methanol for 10 minutes each time. After the cleaning was completed, it was dried at 120°C.

[0361] An organic electroluminescent device was fabricated by vacuum evaporation on a cleaned ITO substrate, consisting of a hole injection layer HI1-1:P-1 = 97:3 (20 nm); a hole transport layer compound 3 (95 nm); an emitting layer RH-1:RH-2:RD-2 = 48:48:4 (mass ratio, 40 nm); an electron transport layer ET-2:Liq = 1:1 (mass ratio, 28 nm); an electron injection layer LiF (1.0 nm); and a cathode Al (100 nm).

[0362]

[0363] [Device Examples 88-129]

[0364] Compounds 8, 16, 26, 29, 60, 77, 91, 131, 141, 174, 192, 213, 240, 316, 396, 451, 497, 511, 512, 524, 552, 562, 586, 599, 620, 631, 692, 695, 732, 737, 758, 778, 870, 871, 929, 945, 947, 948, 962, 984, 991, and 1032 of this invention were used to replace compound 3 in device example 87 as the hole transport layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 87.

[0365] [Comparative Device Examples 5-6]

[0366] Comparative compounds 5 and 6 were used to replace compound 3 in device example 87 as hole transport layer materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 87.

[0367] The luminescence characteristics test results of the organic electroluminescent devices obtained in Examples 87-129 and Comparative Examples 5-6 of the present invention are shown in Table 3 below.

[0368]

[0369]

[0370] As can be seen from the data in Table 3, the fused ring compound described in this invention, when applied to organic electroluminescent devices, benefits from its good hole migration rate, which can optimize the carrier balance of the device and effectively improve the luminous efficiency.

[0371] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A fused-ring compound, characterized in that, The fused-ring compound has the structure represented by Formula I: X is selected from O or S; Ring A and ring B are independently selected from the rings shown below: Furthermore, rings A and B are not selected simultaneously. The v is independently selected from C(R2) or N, and when v is bonded to other groups, the v is selected from C atoms; The R2 is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, and unsubstituted C6-C30 aryl. The z is independently selected from C(R3) or N, and when z is bonded to other groups, the z is selected from C atoms; The R3 is selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl; The Ar is selected from any one of the following groups: The e is independently selected from CH or N, and when the e is bonded to other groups, the e is selected from C atoms; The Q is selected from O, S, N(Rz) or C(RxRy); The Q1 is selected from N(Rz) or C(RxRy); The Rz is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl groups, and substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl groups. The Rx and Ry are independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or Rx and Ry can be interconnected to form one or more substituted or unsubstituted alicyclic groups; The ring M is selected from substituted or unsubstituted C3 to C30 alicyclic rings; The Rd is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl, or adjacent Rds can be interconnected to form one or more substituted or unsubstituted rings; a1 is selected from 0, 1, 2, 3, 4 or 5; a2 is selected from 0, 1, 2, 3 or 4; a3 is selected from 0, 1, 2 or 3; a4 is selected from 0, 1 or 2; The L1 is selected from any one of the following groups and combinations thereof: single bond, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloalcoholic group, or groups listed below: The Rm is independently selected from any one of deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl, or adjacent Rm can be interconnected to form one or more substituted or unsubstituted rings; The Rm1 is independently selected from any one of deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, or adjacent Rm1 can be interconnected to form one or more substituted or unsubstituted rings; The Rm2 and Rm3 are independently selected from any one of deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, or adjacent Rm2 and Rm3 can be interconnected to form one or more substituted or unsubstituted aromatic or alicyclic rings; The p 11 The options are selected from 1, 2, 3, or 4; p1 is selected from 0, 1, 2, 3, or 4; p2 is selected from 0, 1, 2, or 3; p3 is selected from 0, 1, or 2; p4 is selected from 0, 1, 2, 3, 4, 5, or 6. L2 and L3 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and combinations thereof.

2. The fused-ring compound according to claim 1, characterized in that, The Selected from any one of the following groups: The R2 is selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, or any of the following groups substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, trimethylsilyl, triethylsilyl, tritert-butylsilyl, and triphenylsilyl.

3. The fused-ring compound according to claim 1, characterized in that, The Selected from any one of the following groups: The R3 is selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; The n1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the n2 is selected from 0, 1, 2 or 3; the n3 is selected from 0, 1, 2, 3, 4, 5 or 6; the n4 is selected from 0, 1 or 2; the n5 is selected from 0, 1, 2, 3, 4 or 5.

4. The fused-ring compound according to claim 1, characterized in that, The Ar is selected from any one of the following groups: The Rd is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane. Alkyl, norbornel, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, or two adjacent Rds may be connected to each other to form one or more substituted or unsubstituted rings; a1 is selected from 0, 1, 2, 3, 4, or 5; a2 is selected from 0, 1, 2, 3, or 4; a3 is selected from 0, 1, 2, or 3; a4 is selected from 0, 1, or 2; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; a6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; a7 is selected from 0, 1, 2, 3, 4, 5, or 6; a8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; a9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; a 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; a 11 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; a 12 Select from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11.

5. The fused-ring compound according to claim 1, characterized in that, The L1 is selected from a single bond or any of the following groups and combinations thereof: The Rm is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane. Alkyl, norbornel, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, or two adjacent Rm may be connected to each other to form one or more substituted or unsubstituted rings; The Rm1 is independently selected from deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more of deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane. The following compounds can be connected to each other to form one or more substituted or unsubstituted rings: alkyl, norbornelalkyl, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracel, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiopheneyl, or two adjacent Rm1s can be connected to each other to form one or more substituted or unsubstituted rings; The Rm0 is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; the p 11 The options are selected from 1, 2, 3, or 4; p1 is selected from 0, 1, 2, 3, or 4; p2 is selected from 0, 1, 2, or 3; p3 is selected from 0, 1, or 2; p4 is selected from 0, 1, 2, 3, 4, 5, or 6; p5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; p6 is selected from 0, 1, 2, 3, 4, or 5.

6. The fused-ring compound according to claim 1, characterized in that, The L2 and L3 are independently selected from any one of the single bonds or the following groups and combinations thereof: The s is independently selected from CH or N, and when s is bonded to other groups, the s is selected from C atoms; The T is selected from O, S, N(Rw) or C(RhRi); The Rw is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl groups, and substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl groups. The ring K is selected from substituted or unsubstituted C3 to C30 alicyclic rings; The Rh and Ri are independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, or fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or adjacent Rh and Ri can be connected to each other to form substituted or unsubstituted rings; The Rn is independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or adjacent Rn can be interconnected to form one or more substituted or unsubstituted rings; The q1 is selected from 0, 1, 2, 3 or 4; the q2 is selected from 0, 1, 2 or 3; the q3 is selected from 0, 1 or 2; and the q4 is selected from 0, 1, 2, 3, 4, 5 or 6.

7. The fused-ring compound according to claim 1, characterized in that, The fused-ring compound is selected from any one of the following compounds:

8. An organic electroluminescent device, comprising an anode, a cathode, and an organic functional layer, wherein the organic functional layer is located between the anode and the cathode or outside either the anode or the cathode, characterized in that, The organic functional layer comprises any one or more of the fused-ring compounds described in any one of claims 1 to 7.

9. An organic electroluminescent device according to claim 8, wherein the organic functional layer is located between the anode and the cathode, the organic functional layer includes a hole transport region, a light-emitting layer, and an electron transport region, the hole transport region is located between the light-emitting layer and the anode, and the light-emitting layer is located between the electron transport region and the hole transport region, characterized in that, The hole transport region and / or luminescent layer comprises any one or more of the fused ring compounds described in any one of claims 1 to 7.

10. An organic electroluminescent device according to claim 8, wherein the organic functional layer comprises a capping layer located outside either the anode or the cathode, characterized in that, The capping layer comprises any one or more of the fused ring compounds described in any one of claims 1 to 7.

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