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. The fused ring compound provided by the invention has excellent refractive index and good stability when being used as a covering layer material, can effectively improve the luminous efficiency and prolong the service life of a device, and also shows excellent performance when being used as a main body material and a hole transport material. In conclusion, the fused ring compound provided by the invention has a good development prospect in the fields of panel display 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) possess excellent characteristics such as high energy efficiency, low driving voltage, fast response speed, stable emission color, wide viewing angle, and a wide range of material choices, and have been widely used in various fields such as television displays, solid-state lighting, and wearable smart devices. With the rapid expansion of OLED application scenarios and the surge in market demand, the industry has raised higher requirements for display technology, especially focusing on improving overall performance, aiming to achieve ultra-high-definition display effects with high efficiency, long lifespan, and high color saturation optimized in synergy. Against this backdrop, the development of a series of novel organic electroluminescent materials has crucial research value and application significance.

[0003] OLED devices consist of a substrate, cathode, anode, hole injection layer (HIL), electron injection layer (EIL), hole transport layer (HTL), electron transport layer (ETL), electron blocking layer (EBL), hole blocking layer (HBL), light-emitting layer (EML), and capping layer (CP). The light-emitting process can be divided into: electron and hole injection, electron and hole transport, electron and hole recombination, and exciton de-excitation.

[0004] However, the types of materials currently available for OLED device capping layers are limited. Existing materials still have many shortcomings in terms of refractive index control range, long-term stability, and industrial-scale compatibility, making it difficult to fully meet the performance requirements and industrial production demands of different types of OLED devices. Therefore, developing a wider variety of capping layer materials with superior performance has become an urgent need in the current OLED technology research and development field. It is also a key breakthrough in promoting the development of OLED technology towards higher performance and wider application scenarios, and is of great significance to promoting the continuous progress of the organic optoelectronic industry. 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] 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;

[0010] 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;

[0011] The Ar is selected from any one of the following: 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 heteroaromatic fused cycloyl;

[0012] The rings A, B, and C are independently selected from C6 to C30 aromatic rings that are absent, substituted with R2, or unsubstituted, or C1 to C30 heteroaromatic rings that are substituted with R2 or unsubstituted.

[0013] 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;

[0014] 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, substituted or unsubstituted C6-C30 aryl, C2-C30 heteroaryl containing only one heteroatom selected from oxygen, sulfur, and nitrogen, 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.

[0015] L1 and L2 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.

[0016] The L3 is selected from single bonds or any of the groups shown below.

[0017]

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

[0019] The Y is selected from N(Re) or C(RpRq);

[0020] The V is selected from O, S, or N (Rf).

[0021] The Re and Rf are independently selected from any one of the following: 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, fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings.

[0022] The ring W is selected from substituted or unsubstituted C3 to C30 alicyclic rings;

[0023] The Rp and Rq 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 Rp and Rq can be connected to each other to form substituted or unsubstituted rings;

[0024] The Rm 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, or 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;

[0025] 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;

[0026] Two of L1, L2, and L3 / Ar can bond together:

[0027] The i is independently selected from C(Rg) or N, and when i is bonded to other groups, the i is selected from C atoms;

[0028] The Rg 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.

[0029] 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.

[0030] Beneficial effects: This invention provides a fused ring compound that, when used as a capping layer material, has excellent refractive index and good stability, which can effectively improve the luminous efficiency and lifespan of the device. At the same time, it also exhibits excellent performance when used as a host material and hole transport material. Detailed Implementation

[0031] 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.

[0032] 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.

[0033] In this specification, "*" indicates a portion connected to another substituent.

[0034] 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.

[0035] 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.

[0036] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, or iodine.

[0037] 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.

[0038] 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.

[0039] 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 kThe 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... k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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.

[0047] 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.

[0048] 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 substitution is not limited. When multiple hydrogen atoms are substituted by multiple substituents, the multiple substituents may be the same or different.

[0049] 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.

[0050] 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:

[0051]

[0052] 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.

[0053] This invention provides a fused-ring compound having the structure shown in Formula I.

[0054]

[0055] X is selected from O or S;

[0056] 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;

[0057] 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;

[0058] The Ar is selected from any one of the following: 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 heteroaromatic fused cycloyl;

[0059] The rings A, B, and C are independently selected from C6 to C30 aromatic rings that are absent, substituted with R2, or unsubstituted, or C1 to C30 heteroaromatic rings that are substituted with R2 or unsubstituted.

[0060] 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;

[0061] 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, substituted or unsubstituted C6-C30 aryl, C2-C30 heteroaryl containing only one heteroatom selected from oxygen, sulfur, and nitrogen, 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.

[0062] L1 and L2 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.

[0063] The L3 is selected from single bonds or any of the groups shown below.

[0064]

[0065] The u is independently selected from CH or N, and when u is bonded to other groups, the u is selected from C atoms;

[0066] The Y is selected from N(Re) or C(RpRq);

[0067] The V is selected from O, S, or N(Rf);

[0068] The Re and Rf are independently selected from any one of the following: 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, fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings.

[0069] The ring W is selected from substituted or unsubstituted C3 to C30 alicyclic rings;

[0070] The Rp and Rq 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 Rp and Rq can be connected to each other to form substituted or unsubstituted rings;

[0071] The Rm 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, or 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;

[0072] 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;

[0073] Two of L1, L2, and L3 / Ar can bond together:

[0074] The i is independently selected from C(Rg) or N, and when i is bonded to other groups, the i is selected from C atoms;

[0075] The Rg 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.

[0076] Preferably, the Selected from any one of the following groups:

[0077]

[0078]

[0079] The R2 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.

[0080] Preferably, at most three, two, or one v in each group are selected from N.

[0081] Preferably, the Selected from any one of the following groups:

[0082]

[0083]

[0084] 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.

[0085] Preferably, at most three, two, or one z in each group are selected from N.

[0086] Preferably, Ar is selected from any one of the following groups:

[0087]

[0088] 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;

[0089] The Q is selected from O, S, N(Rz) or C(RxRy);

[0090] The Q1 is selected from N(Rz) or C(RxRy);

[0091] 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.

[0092] The Rx and Ry 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 Rx and Ry can be interconnected to form one or more substituted or unsubstituted rings;

[0093] The ring M is selected from substituted or unsubstituted C3 to C30 alicyclic rings;

[0094] 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;

[0095] 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.

[0096] Preferably, the Ar is selected from any one of the following groups:

[0097]

[0098]

[0099] The Rz 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, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene;

[0100] 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;

[0101] 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;

[0102] 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.

[0103] Preferably, L1 and L2 are independently selected from single bonds or any one of the following groups and combinations thereof:

[0104]

[0105] The s is independently selected from CH or N, and when s is bonded to other groups, the s is selected from C atoms;

[0106] The T is selected from O, S, N(Rw) or C(RhRi);

[0107] 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.

[0108] The ring K is selected from substituted or unsubstituted C3 to C30 alicyclic rings;

[0109] 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;

[0110] 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;

[0111] 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.

[0112] More preferably, L1 and L2 are independently selected from single bonds or any of the following groups and combinations thereof:

[0113]

[0114] 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;

[0115] 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.

[0116] Preferably, L3 is selected from single bonds or any of the following groups and combinations thereof:

[0117]

[0118] 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;

[0119] 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.

[0120] Preferably, L1 and L2 can be bonded together: Alternatively, L1 and L3 can be bonded together: Alternatively, L1 and Ar can bond together: Alternatively, L2 and L3 can bond together: Alternatively, L2 and Ar can bond together:

[0121] Preferred, At most three, two, or one i are selected from N. Furthermore, preferably, In each of the six-membered rings containing i, at most one i is selected from N.

[0122] Preferably, the fused-ring compound is selected from any one of the following structures:

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[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]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169] 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.

[0170] 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.

[0171] 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.

[0172] 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.

[0173] 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.

[0174] 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.

[0175] 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.

[0176] 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:

[0177] The organic electroluminescent device of the present invention is typically formed on a substrate. The substrate can be any material that remains unchanged when forming electrodes or organic layers, such as glass, plastic, polymer films, silicon, etc.

[0178] 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.

[0179] 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 metal oxides such as silver oxide, vanadium oxide, tungsten oxide, copper oxide, and titanium oxide, phthalocyanine compounds, benzidine compounds, phenazine compounds, etc., but are not limited thereto.

[0180] 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.

[0181] 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.

[0182] 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.

[0183] 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 2,5,8,11-tetra-tert-butylperylene (TBPe), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (BDAVBi), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), and bis(4,6-difluorophenylpyridine-C2,N)pyridinecarboxyiridium (FIr). Examples of iridium tri(2-phenylpyridine) iridium (Ir(ppy)3), iridium di(2-phenylpyridine) acetylacetonate (Ir(ppy)2(acac)), 9,10-bis[N-(p-tolyl)aniline]anthracene (TPA), tri[1-phenylisoquinoline-C2,N]iridium(III) (Ir(piq)3), iridium di(1-phenylisoquinoline)(acetylacetonate) iridium (Ir(piq)2(acac)), etc., but not limited to these.

[0184] 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.

[0185] 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), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), tris(8-hydroxyquinoline)aluminum(III) (Alq3), di(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), etc., but is not limited thereto.

[0186] 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.

[0187] 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.

[0188] 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.

[0189] 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.

[0190] 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.

[0191] The organic electroluminescent device of the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0192] 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.

[0193] 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:

[0194]

[0195] When L1, L2, and L3 can bond to each other in a substituted or unsubstituted manner: hour;

[0196]

[0197] Among them, Xa, Xb, Xc, Xd, Xe, and Xf are the same or different from each other, and are selected from any one of Cl, Br, and I; the limitations of A, B, C, L1, L2, L3, Ar, X, i, and v are the same as those described above.

[0198] 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.

[0199] 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.

[0200] Preparation and characterization of compounds

[0201] Description of raw materials, reagents, and characterization equipment:

[0202] 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.

[0203] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0204] 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.

[0205] Synthesis Example 1: Preparation of c-130

[0206]

[0207] Preparation of intermediate E-130:

[0208] Under nitrogen protection, e-130 (14.45 g, 55.00 mmol), pinacol diborate (13.97 g, 55.00 mmol), potassium acetate (10.80 g, 110.00 mmol), 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride (0.40 g, 0.55 mmol), and 290 mL of N,N-dimethylformamide were added sequentially to the reaction flask. The mixture was then heated for 6.0 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene. The dried product yielded intermediate E-130 (15.78 g, 81% yield); HPLC purity ≥99.86%. Mass spectrometry m / z: 354.1780 (theoretical value: 354.1791).

[0209] Preparation of intermediate c-130:

[0210] Under nitrogen protection, E-130 (14.17 g, 40.00 mmol), f-130 (7.66 g, 40.00 mmol), and K₂CO₃ (11.06 g, 80.00 mmol) were dissolved in 180 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl₂ (0.59 g, 0.80 mmol) was added with stirring, and the mixture was heated under reflux for 6 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol at a ratio of 5:1 to give intermediate c-130 (10.57 g, yield 78%); HPLC purity ≥ 99.85%. Mass spectrometry m / z: 338.0874 (theoretical value: 338.0862).

[0211] Following the method described above, the following intermediates were synthesized by equimolar substitution of raw materials e-130 and f-130.

[0212]

[0213] Synthesis Example 2: Preparation of a-1396

[0214]

[0215] Under nitrogen protection, H-1 (12.84 g, 30.00 mmol), pinacol diborate (7.62 g, 30.00 mmol), potassium acetate (5.89 g, 60.00 mmol), 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride (0.22 g, 0.30 mmol), and 180 mL of N,N-dimethylformamide were added sequentially to the reaction flask. The mixture was then heated to react for 5.5 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene. After drying, intermediate a-1396 (13.09 g, yield 84%) was obtained; HPLC purity ≥99.86%. Mass spectrometry m / z: 519.2370 (theoretical value: 519.2383).

[0216] Following the method described above, the following intermediates were synthesized by equimolar substitution of raw material H-1.

[0217]

[0218] Synthesis Example 3: Preparation of Compound 3

[0219]

[0220] Preparation of intermediate A-3:

[0221] 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 2.5 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 (18.07 g, yield 83%). The purity of the solid was ≥99.88% as determined by HPLC. Mass spectrometry m / z: 435.1635 (theoretical value: 435.1623).

[0222] Preparation of compound 3:

[0223] Under nitrogen protection, toluene (250 mL), A-3 (13.01 g, 30.00 mmol), c-3 (9.21 g, 30.00 mmol), sodium tert-butoxide (5.77 g, 60.00 mmol), tris(benzylacetone) dipalladium (0.27 g, 0.30 mmol), and X-phos (0.29 g / L, 0.60 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 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 (15.01 g, yield 76%). The purity of the solid was ≥99.97% as determined by HPLC. Mass spectrometry m / z: 661.2418 (theoretical value: 661.2406). Theoretical elemental content (%) C 50 H 31 NO: C, 90.74; H, 4.72; N, 2.12. Measured elemental content (%): C, 90.76; H, 4.74; N, 2.15.

[0224] Synthesis Example 4: Preparation of Compound 12

[0225]

[0226] According to the preparation method in Synthesis Example 2, b-3 was replaced with an equimolar amount of b-12 to obtain compound 12 (14.89 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 661.2418 (theoretical value: 661.2406). Theoretical elemental content (%) C 50 H 31 NO: C, 90.74; H, 4.72; N, 2.12. Measured elemental content (%): C, 90.76; H, 4.70; N, 2.14.

[0227] Synthesis Example 5: Preparation of Compound 22

[0228]

[0229] According to the preparation method in Synthesis Example 2, b-3 was replaced with an equimolar amount of b-22 to obtain compound 22 (14.49 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 711.2545 (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, 91.13; H, 4.65; N, 1.94.

[0230] Synthesis Example 6: Preparation of Compound 35

[0231]

[0232] According to the preparation method in Example 2, b-3 was replaced with an equimolar amount of b-35 to obtain compound 35 (14.71 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 662.2342 (theoretical value: 662.2358). Theoretical elemental content (%) C 49 H 30 N₂O: C, 88.80; H, 4.56; N, 4.23. Measured elemental content (%): C, 88.82; H, 4.54; N, 4.27.

[0233] Synthesis Example 7: Preparation of Compound 38

[0234]

[0235] According to the preparation method in Example 2, a-3 was replaced with an equimolar amount of a-38 to obtain compound 38 (15.94 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 737.2703 (theoretical value: 737.2719). Theoretical elemental content (%) C 56 H 35 NO: C, 91.15; H, 4.78; N, 1.90. Measured elemental content (%): C, 91.11; H, 4.76; N, 1.93.

[0236] Synthesis Example 8: Preparation of Compound 63

[0237]

[0238] According to the preparation method in Synthesis Example 2, b-3 was replaced with an equimolar amount of b-63 to obtain compound 63 (15.72 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 737.2705 (theoretical value: 737.2719). Theoretical elemental content (%) C 56 H 35 NO: C, 91.15; H, 4.78; N, 1.90. Measured elemental content (%): C, 91.17; H, 4.75; N, 1.92.

[0239] Synthesis Example 9: Preparation of Compound 83

[0240]

[0241] According to the preparation method in Example 2, a-3 was replaced with an equimolar amount of a-83 to obtain compound 83 (14.43 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 667.1957 (theoretical value: 667.1970). 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.

[0242] Synthesis Example 10: Preparation of Compound 85

[0243]

[0244] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-83, and b-3 was replaced with an equimolar amount of b-85, yielding compound 85 (14.22 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 667.1957 (theoretical value: 667.1970). Theoretical elemental content (%) C 48 H 29 NOS: C, 86.33; H, 4.38; N, 2.10. Measured elemental content (%): C, 86.31; H, 4.36; N, 2.08.

[0245] Synthesis Example 11: Preparation of Compound 101

[0246]

[0247] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-83, and b-3 was replaced with an equimolar amount of b-101 to obtain compound 101 (15.08 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 717.2112 (theoretical value: 717.2126). Theoretical elemental content (%) C 52 H 31 NOS: C, 87.00; H, 4.35; N, 1.95. Measured elemental content (%): C, 87.03; H, 4.32; N, 1.97.

[0248] Synthesis Example 12: Preparation of Compound 130

[0249]

[0250] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-83, b-3 was replaced with an equimolar amount of b-130, and c-3 was replaced with an equimolar amount of c-130, yielding compound 130 (16.97 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 819.2582 (theoretical value: 819.2596). Theoretical elemental content (%) C 60 H 37 NOS: C, 87.88; H, 4.55; N, 1.71. Measured elemental content (%): C, 87.86; H, 4.52; N, 1.75.

[0251] Synthetic Example 13: Preparation of Compound 135

[0252]

[0253] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-135 to obtain compound 135 (13.71 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 671.2236 (theoretical value: 671.2221). Theoretical elemental content (%) C 48 H 25 D4NOS: C, 85.81; H, 4.95; N, 2.08. Measured elemental content (%): C, 85.84; H, 4.98; N, 2.05.

[0254] Synthesis Example 14: Preparation of Compound 167

[0255]

[0256] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-167, and c-3 was replaced with an equimolar amount of c-167 to obtain compound 167 (13.69 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 651.2185 (theoretical value: 651.2198). Theoretical elemental content (%) C 48 H 29 NO2: C, 88.46; H, 4.49; N, 2.15. Measured elemental content (%): C, 88.43; H, 4.52; N, 2.18.

[0257] Synthesis Example 15: Preparation of Compound 193

[0258]

[0259] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-193 to obtain compound 193 (14.53 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 701.2371 (theoretical value: 701.2355). Theoretical elemental content (%) C 52 H 31 NO2: C, 88.99; H, 4.45; N, 2.00. Measured elemental content (%): C, 88.95; H, 4.48; N, 2.03.

[0260] Synthesis Example 16: Preparation of Compound 203

[0261]

[0262] According to the preparation method in Example 2, a-3 was replaced with an equimolar amount of a-203 to obtain compound 203 (13.52 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 625.2052 (theoretical value: 625.2042). Theoretical elemental content (%) C 46 H 27 NO2: C, 88.30; H, 4.35; N, 2.24. Measured elemental content (%): C, 88.32; H, 4.38; N, 2.21.

[0263] Synthesis Example 17: Preparation of Compound 241

[0264]

[0265] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-241 to obtain compound 241 (13.29 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 632.2493 (theoretical value: 632.2481). Theoretical elemental content (%) C 46 H 20 D7NO2: C, 87.32; H, 5.41; N, 2.21. Measured elemental content (%): C, 87.35; H, 5.45; N, 2.18.

[0266] Synthetic Example 18: Preparation of Compound 286

[0267]

[0268] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-286, and c-3 was replaced with an equimolar amount of b-3 to obtain compound 286 (13.79 g). HPLC analysis showed that the solid purity was ≥99.96%. Mass spectrometry m / z: 675.2186 (theoretical value: 675.2198). Theoretical elemental content (%) C50H29NO2: C, 88.87; H, 4.33; N, 2.07. Measured elemental content (%): C, 88.89; H, 4.30; N, 2.04.

[0269] Synthesis Example 19: Preparation of Compound 405

[0270]

[0271] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-83, and b-3 was replaced with an equimolar amount of b-405, yielding compound 405 (14.91 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 709.1890 (theoretical value: 709.1898). Theoretical elemental content (%) C 50 H 31 NS2: C, 84.59; H, 4.40; N, 1.97. Measured elemental content (%): C, 84.56; H, 4.44; N, 1.98.

[0272] Synthesis Example 20: Preparation of Compound 427

[0273]

[0274] According to the preparation method in Example 2, a-3 was replaced with an equimolar amount of a-427 to obtain compound 427 (14.10 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 652.2165 (theoretical value: 652.2151). Theoretical elemental content (%) C 47 H 28 N2O2: C, 86.48; H, 4.32; N, 4.29. Measured elemental content (%): C, 86.45; H, 4.35; N, 4.26.

[0275] Synthesis Example 21: Preparation of Compound 491

[0276]

[0277] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-491, and b-3 was replaced with an equimolar amount of b-491, yielding compound 491 (16.56 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 711.2550 (theoretical value: 711.2562). Theoretical elemental content (%) C 62 H 37 NO: C, 91.71; H, 4.59; N, 1.73. Measured elemental content (%): C, 91.74; H, 4.56; N, 1.70.

[0278] Synthesis Example 22: Preparation of Compound 515

[0279]

[0280] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-515, and b-3 was replaced with an equimolar amount of b-515, yielding compound 515 (15.54 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 761.2705 (theoretical value: 761.2719). Theoretical elemental content (%) C 58 H 35 NO: C, 91.43; H, 4.63; N, 1.84. Measured elemental content (%): C, 91.47; H, 4.60; N, 1.88.

[0281] Synthesis Example 23: Preparation of Compound 524

[0282]

[0283] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-286 to obtain compound 524 (14.20 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 685.2419 (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, 91.05; H, 4.59; N, 2.07.

[0284] Synthesis Example 24: Preparation of Compound 558

[0285]

[0286] According to the preparation method in Example 2, a-3 was replaced with an equimolar amount of a-286, and c-3 was replaced with an equimolar amount of c-558, yielding compound 558 (14.72 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 700.2502 (theoretical value: 700.2515). Theoretical elemental content (%) C 52 H 32 N₂O: C, 89.12; H, 4.60; N, 4.00. Measured elemental content (%): C, 89.15; H, 4.63; N, 4.03.

[0287] Synthesis Example 25: Preparation of Compound 561

[0288]

[0289] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-286, and c-3 was replaced with an equimolar amount of c-561, yielding compound 561 (15.83 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 775.2862 (theoretical value: 775.2875). Theoretical elemental content (%) C 59 H 37 NO: C, 91.33H, 4.81; N, 1.81. Measured elemental content (%): C, 91.30H, 4.83; N, 1.84.

[0290] Synthesis Example 26: Preparation of Compound 586

[0291]

[0292] According to the preparation method in Example 2, a-3 was replaced with an equimolar amount of a-586 to obtain compound 586 (13.51 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 616.2577 (theoretical value: 616.2563). Theoretical elemental content (%) C 46 H 24 D5NO: C, 89.58; H, 5.56; N, 2.27. Measured elemental content (%): C, 89.61; H, 5.53; N, 2.25.

[0293] Synthesis Example 27: Preparation of Compound 589

[0294]

[0295] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-589 to obtain compound 589 (15.89 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 745.3332 (theoretical value: 745.3345). Theoretical elemental content (%) C 56 H 43 NO: C, 90.17; H, 5.81; N, 1.88. Measured elemental content (%): C, 90.13; H, 5.84; N, 1.85.

[0296] Synthesis Example 28: Preparation of Compound 591

[0297]

[0298] According to the preparation method in Example 2, a-3 was replaced with an equimolar amount of a-591 to obtain compound 591 (14.38 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 665.2702 (theoretical value: 665.2719). Theoretical elemental content (%) C 50 H 35 NO: C, 90.19; H, 5.30; N, 2.10. Measured elemental content (%): C, 90.16; H, 5.34; N, 2.13.

[0299] Synthesis Example 29: Preparation of Compound 602

[0300]

[0301] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-602, and b-3 was replaced with an equimolar amount of b-602, yielding compound 602 (15.20 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 703.2347 (theoretical value: 703.2334). Theoretical elemental content (%) C 52 H 33 NS: C, 88.73; H, 4.73; N, 1.99. Measured elemental content (%): C, 88.75; H, 4.77; N, 1.96.

[0302] Synthesis Example 30: Preparation of Compound 694

[0303]

[0304] According to the preparation method in Example 2, a-3 was replaced with an equimolar amount of a-694 to obtain compound 694 (11.89 g, yield 74%). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 535.1947 (theoretical value: 535.1936). Theoretical elemental content (%) C 40 H 25 NO: C, 89.69; H, 4.70; N, 2.61. Measured elemental content (%): C, 89.65; H, 4.73; N, 2.65.

[0305] Synthesis Example 31: Preparation of Compound 706

[0306]

[0307] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-706, and b-3 was replaced with an equimolar amount of b-706, yielding compound 706 (14.22 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 667.1958 (theoretical value: 667.1970). Theoretical elemental content (%) C 48 H 29 NOS: C, 86.33; H, 4.38; N, 2.10. Measured elemental content (%): C, 86.36; H, 4.35; N, 2.14.

[0308] Synthesis Example 32: Preparation of Compound 714

[0309]

[0310] According to the preparation method in Example 2, c-3 was replaced with an equimolar amount of c-714 to obtain compound 714 (18.84 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 965.3670 (theoretical value: 965.3658). Theoretical elemental content (%) C 74 H 47 NO: C, 91.99; H, 4.90; N, 1.45. Measured elemental content (%): C, 91.95; H, 4.93; N, 1.47.

[0311] Synthesis Example 33: Preparation of Compound 901

[0312]

[0313] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-901, and b-3 was replaced with an equimolar amount of b-602, yielding compound 901 (15.02 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 685.1666 (theoretical value: 685.1646). Theoretical elemental content (%) C 46 H 27 N3S2: C, 80.56; H, 3.97; N, 6.13. Measured elemental content (%): C, 80.59; H, 3.95; N, 6.10.

[0314] Synthesis Example 34: Preparation of Compound 922

[0315]

[0316] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-922, and b-3 was replaced with an equimolar amount of b-602, yielding compound 922 (15.29 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 727.2319 (theoretical value: 727.2334). Theoretical elemental content (%) C 54 H 33 NS: C, 89.10; H, 4.57; N, 1.92. Measured elemental content (%): C, 89.13; H, 4.54; N, 1.95.

[0317] Synthesis Example 35: Preparation of Compound 926

[0318]

[0319] According to the preparation method in Example 2, c-3 was replaced with an equimolar amount of c-926 to obtain compound 926 (15.77 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 761.2707 (theoretical value: 761.2719). Theoretical elemental content (%) C 58 H 35 NO: C, 91.43; H, 4.63; N, 1.84. Measured elemental content (%): C, 91.47; H, 4.65; N, 1.80.

[0320] Synthesis Example 36: Preparation of Compound 936

[0321]

[0322] According to the preparation method in Synthesis Example 2, c-3 was replaced with an equimolar amount of c-936 to obtain compound 936 (14.95 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 711.2573 (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, 91.15; H, 4.69; N, 1.95.

[0323] Synthesis Example 37: Preparation of Compound 956

[0324]

[0325] According to the preparation method in Example 2, c-3 was replaced with an equimolar amount of c-956 to obtain compound 956 (17.37 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 863.3175 (theoretical value: 863.3188). Theoretical elemental content (%) C 66 H 41 NO: C, 91.74; H, 4.78; N, 1.62. Measured elemental content (%): C, 91.77; H, 4.74; N, 1.65.

[0326] Synthesis Example 38: Preparation of Compound 976

[0327]

[0328] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-83, b-3 was replaced with an equimolar amount of b-976, and c-3 was replaced with an equimolar amount of c-936, yielding compound 976 (14.64 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 717.2112 (theoretical value: 717.2126). Theoretical elemental content (%) C 52 H 31 NOS: C, 87.00; H, 4.35; N, 1.95. Measured elemental content (%): C, 87.03; H, 4.32; N, 1.92.

[0329] Synthesis Example 39: Preparation of Compound 988

[0330]

[0331] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-83, and c-3 was replaced with an equimolar amount of c-988, yielding compound 988 (14.64 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 717.2140 (theoretical value: 717.2126). Theoretical elemental content (%) C 52 H 31 NOS: C, 87.00; H, 4.35; N, 1.95. Measured elemental content (%): C, 87.04; H, 4.38; N, 1.93.

[0332] Synthesis Example 40: Preparation of Compound 1029

[0333]

[0334] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-1029, b-3 was replaced with an equimolar amount of b-1029, and c-3 was replaced with an equimolar amount of c-936, yielding compound 1029 (14.88 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 718.2068 (theoretical value: 718.2079). Theoretical elemental content (%) C 51 H 30 N₂OS: C, 85.21; H, 4.21; N, 3.90. Measured elemental content (%): C, 85.25; H, 4.23; N, 3.92.

[0335] Synthesis Example 41: Preparation of Compound 1301

[0336]

[0337] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-1301, b-3 was replaced with an equimolar amount of b-1301, and c-3 was replaced with an equimolar amount of c-936, yielding compound 1301 (14.91 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 709.2820 (theoretical value: 709.2803). Theoretical elemental content (%) C 52 H 39 NS: C, 87.97; H, 5.54; N, 1.97. Measured elemental composition (%): C, 87.99; H, 5.58; N, 1.95. Synthesis Example 42: Preparation of Compound 1317

[0338]

[0339] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-1317, b-3 was replaced with an equimolar amount of b-1317, and c-3 was replaced with an equimolar amount of c-936, yielding compound 1317 (15.66 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 745.2037 (theoretical value: 745.2051). Theoretical elemental content (%) C 51 H 30 F3NS: C, 82.13; H, 4.05; N, 1.88. Measured elemental content (%): C, 82.15; H, 4.02; N, 1.85.

[0340] Synthesis Example 43: Preparation of Compound 1355

[0341]

[0342] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-1355, b-3 was replaced with an equimolar amount of b-1355, and c-3 was replaced with an equimolar amount of c-936, yielding compound 1355 (14.91 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 699.2405 (theoretical value: 699.2416). Theoretical elemental content (%) C 49 H 37 NSSi: C, 84.08; H, 5.33; N, 2.00. Measured elemental content (%): C, 84.05; H, 5.30; N, 2.03.

[0343] Synthesis Example 44: Preparation of Compound 1386

[0344]

[0345] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-1386, b-3 was replaced with an equimolar amount of b-602, and c-3 was replaced with an equimolar amount of c-936, yielding compound 1386 (14.66 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 718.2067 (theoretical value: 718.2079). Theoretical elemental content (%) C 51 H 30 N₂OS: C, 85.21; H, 4.21; N, 3.90. Measured elemental content (%): C, 85.24; H, 4.18; N, 3.93.

[0346] Synthesis Example 45: Preparation of Compound 1390

[0347]

[0348] According to the preparation method in Synthesis Example 2, b-3 was replaced with an equimolar amount of b-1390, and c-3 was replaced with an equimolar amount of c-936, yielding compound 1390 (17.95 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 879.2971 (theoretical value: 879.2960). Theoretical elemental content (%) C 66 H 41 NS: C, 90.07; H, 4.70; N, 1.59. Measured elemental content (%): C, 90.05; H, 4.73; N, 1.56.

[0349] Synthesis Example 46: Preparation of Compound 1395

[0350]

[0351] According to the preparation method in Synthesis Example 2, a-3 was replaced with an equimolar amount of a-203, b-3 was replaced with an equimolar amount of b-1395, and c-3 was replaced with an equimolar amount of c-936, yielding compound 1395 (14.32 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 691.1955 (theoretical value: 691.1970). Theoretical elemental content (%) C 50 H 29 NOS: C, 86.80; H, 4.23; N, 2.02. Measured elemental content (%): C, 86.83; H, 4.25; N, 2.00.

[0352] Synthesis Example 47: Preparation of Compound 1396

[0353]

[0354] Preparation of intermediate A-1396:

[0355] Under argon protection, a-1396 (12.98 g, 25.00 mmol), c-3 (7.65 g, 25.00 mmol), K2CO3 (5.53 g, 40.00 mmol), and 200 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to a reaction flask. After purging the air three times with argon, Pd(PPh3)4 (0.29 g, 0.25 mmol) was added. The mixture was stirred and heated under reflux for 4 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the toluene layer was separated and dried with anhydrous magnesium sulfate. The solvent was concentrated by rotary evaporation after filtration, and crystals were precipitated by cooling and filtration. The crystals were then recrystallized from toluene / methanol in a 9:1 ratio to obtain intermediate A-1396 (12.71 g, yield 82%) with an HPLC purity ≥99.86%. Mass spectrometry m / z: 619.2313 (theoretical value: 619.2300). Preparation of compound 1396:

[0356] Under nitrogen protection, A-1396 (12.39 g, 20.00 mmol), b-3 (5.94 g, 20.00 mmol), and sodium tert-butoxide (3.84 g, 40.00 mmol) dissolved in 120 mL of toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (0.18 g, 0.20 mmol) and X-Phos (0.29 g, 0.60 mmol) were then added. The mixture of the above reactants was heated under reflux for 5.0 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound 1396 (11.70 g, 70% yield). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 835.2862 (theoretical value: 835.2875). Theoretical elemental content (%) C 64 H 37 NO: C, 91.95; H, 4.46; N, 1.68; Measured element content (%): C, 91.97; H, 4.43; N, 1.64.

[0357] Synthesis Example 48: Preparation of Compound 1475

[0358]

[0359] According to the preparation method of Synthesis Example 47, a-1396 was replaced with an equimolar amount of a-1475, c-3 was replaced with an equimolar amount of b-3, and b-3 was replaced with an equimolar amount of c-1475 to obtain compound 1475 (10.45 g). HPLC analysis showed that the solid purity was ≥99.95%. Mass spectrometry m / z: 735.2547 (theoretical value: 735.2562). Theoretical elemental content (%) C 56 H33 NO: C, 91.40; H, 4.52; N, 1.90. Measured elemental content (%): C, 91.42; H, 4.50; N, 1.93.

[0360] Device Examples

[0361] 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.

[0362] 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 .

[0363] [Device Example 1]

[0364] 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.

[0365] An organic electroluminescent device was fabricated by vacuum evaporation on a cleaned ITO / Ag / ITO substrate, consisting of a hole injection layer P-1:HT1-1 = 5:95 (mass ratio, 10 nm); a hole transport layer HT1-1 (105 nm); an emitting layer GH-1:GD-1 = 97:3 (mass ratio, 35 nm); an electron transport layer ET-1:Liq = 1:1 (mass ratio, 30 nm); an electron injection layer LiF (0.8 nm); a cathode Mg:Ag = 1:9 (mass ratio, 12 nm); and a capping layer compound 3 (80 nm).

[0366]

[0367] [Device Examples 2-46]

[0368] Using compounds 12, 22, 35, 38, 63, 83, 85, 101, 130, 135, 167, 193, 203, 241, 286, 405, 427, 491, 515, 524, 558, 561, 586, 589, 591, 602, and 694, compound... Compounds 706, 714, 901, 922, 926, 936, 956, 976, 988, 1029, 1301, 1317, 1355, 1386, 1390, 1395, 1396, and 1475 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 in device example 1.

[0369] [Comparative Device Examples 1-2]

[0370] 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.

[0371] The luminescence characteristics test results of the organic electroluminescent devices obtained in Embodiments 1-46 of the present invention and Comparative Embodiments 1-2 are shown in Table 1 below.

[0372]

[0373]

[0374] 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.

[0375] [Device Example 47]

[0376] 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.

[0377] An organic electroluminescent device was fabricated by vacuum evaporation on a cleaned ITO substrate, consisting of: a hole injection layer HT1-2:P-1 = 97:3 (20 nm); a first hole transport layer HT1-2 (90 nm); an emitting layer compound 3:GH-2:GD-1 = 46:46:8 (mass ratio, 35 nm); an electron transport layer ET-1:Liq = 1:1 (mass ratio, 30 nm); an electron injection layer LiF (1.0 nm); and a cathode Mg:Ag = 1:9 (mass ratio, 15 nm).

[0378]

[0379] [Device Examples 48-92]

[0380] Compounds 12, 22, 35, 38, 63, 83, 85, 101, 130, 135, 167, 193, 203, 241, 286, 405, 427, 491, 515, 524, 558, 561, 586, 589, 591, 602, 694, and 7 are used. Compounds 06, 714, 901, 922, 926, 936, 956, 976, 988, 1029, 1301, 1317, 1355, 1386, 1390, 1395, 1396, and 1475 were used to replace compound 3 in device example 47 as the main material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in device example 47.

[0381] [Comparative Device Examples 3-4]

[0382] Comparative compound 3 and comparative compound 4 were used to replace compound 3 in device example 47 as the main material. Otherwise, organic electroluminescent devices were prepared by the same preparation method as device example 47.

[0383] The luminescence characteristics test results of the organic electroluminescent devices obtained in Examples 47-92 and Comparative Examples 3-4 of the present invention are shown in Table 2 below.

[0384]

[0385]

[0386] As can be seen from the data in Table 2, the fused ring compound described in this invention is used as the main material in organic electroluminescent devices, giving the devices excellent performance.

[0387] [Device Example 93]

[0388] 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.

[0389] An organic electroluminescent device was fabricated by vacuum evaporation on a cleaned ITO substrate, consisting of a hole injection layer HT1-2:P-2 = 97:3 (20 nm); a first hole transport layer compound 2 (90 nm); an emitting layer GH-1:GD-1 = 97:3 (mass ratio, 40 nm); an electron transport layer ET-2:Liq = 1:1 (mass ratio, 25 nm); an electron injection layer LiF (1.0 nm); and a cathode Mg:Ag = 1:9 (mass ratio, 15 nm).

[0390]

[0391] [Device Examples 94-138]

[0392] Compounds 12, 22, 35, 38, 63, 83, 85, 101, 130, 135, 167, 193, 203, 241, 286, 405, 427, 491, 515, 524, 558, 561, 586, 589, 591, 602, 694, and 70 are used. 6. Compounds 714, 901, 922, 926, 936, 956, 976, 988, 1029, 1301, 1317, 1355, 1386, 1390, 1395, 1396, and 1475 are used to replace compound 3 in device example 93 as hole transport layer materials. Otherwise, organic electroluminescent devices are prepared using the same preparation method as in device example 93.

[0393] [Comparative Device Examples 5-6]

[0394] Comparative compounds 5 and 6 were used to replace compound 3 in device example 93 as hole transport layer materials. Otherwise, organic electroluminescent devices were prepared using the same preparation method as device example 93.

[0395] The luminescence characteristics test results of the organic electroluminescent devices obtained in Examples 93-138 and Comparative Examples 5-6 of the present invention are shown in Table 3 below.

[0396]

[0397]

[0398] As can be seen from the data in Table 2, the fused ring compound described in this invention exhibits good hole migration rate when applied to organic electroluminescent devices.

[0399] 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; 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: 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 heteroaromatic fused cycloyl; The rings A, B, and C are independently selected from C6 to C30 aromatic rings that are absent, substituted with R2, or unsubstituted, or C1 to C30 heteroaromatic rings that are substituted with R2 or unsubstituted. 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; 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, substituted or unsubstituted C6-C30 aryl, C2-C30 heteroaryl containing only one heteroatom selected from oxygen, sulfur, and nitrogen, 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. L1 and L2 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. The L3 is selected from single bonds or any of the groups shown below. The u is independently selected from CH or N, and when u is bonded to other groups, the u is selected from C atoms; The Y is selected from N(Re) or C(RpRq); The V is selected from O, S, or N(Rf); The Re and Rf are independently selected from any one of the following: 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, fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings. The ring W is selected from substituted or unsubstituted C3 to C30 alicyclic rings; The Rp and Rq 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 Rp and Rq can be connected to each other to form substituted or unsubstituted rings; The Rm 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, or 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; 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; Two of L1, L2, and L3 / Ar can bond together: The i is independently selected from C(Rg) or N, and when i is bonded to other groups, the i is selected from C atoms; The Rg 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.

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, 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.

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.

4. The fused-ring compound according to claim 1, characterized in that, 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 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 Rx and Ry can be interconnected to form one or more substituted or unsubstituted rings; 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.

5. The fused-ring compound according to claim 1, characterized in that, The Ar is selected from any one of the following groups: The Rz 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, norbornane, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene; 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.

6. The fused-ring compound according to claim 1, characterized in that, The L1 and L2 are independently selected from any one of the following groups or 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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