A carbazole-containing compound and an organic electroluminescent device thereof

Abstract

This invention provides a carbazole compound and its organic electroluminescent device, specifically relating to the field of organic electroluminescent materials technology. The carbazole compound provided by this invention, when used as a capping material, exhibits a relatively balanced evaporation temperature and refractive index, and possesses suitable molecular weight, evaporation temperature, sublimation temperature, and good stability, thus improving and enhancing light extraction efficiency, while effectively increasing the luminous efficiency and lifespan of the device. In summary, the carbazole compound provided by this invention has good development potential in the field of organic electroluminescent materials technology and can be widely applied.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) are devices that emit light by causing carrier injection and recombination in organic materials through the action of an electric field. They can convert electrical energy into light energy and are the next generation of display technology after CRT and LCD. They have been widely used in smartphones, tablets and other fields, and are gradually expanding into the field of large-screen TVs, with broad development prospects.

[0003] OLED devices are classified into bottom-emitting and top-emitting types according to their light emission path. Currently, top-emitting devices are more widely used, and their light extraction efficiency is superior to that of bottom-emitting devices. Top-emitting devices, by adding a capping layer outside the metal cathode, can suppress the loss of emitted light caused by total internal reflection and couple out the light trapped inside the device, thereby enhancing the light extraction efficiency and improving the device's luminous efficiency. Therefore, they have excellent development prospects. However, although top-emitting devices have advantages, they still have the problem of forming a microcavity between the metal cathode and the bottom reflective layer, resulting in a strong dependence on the light emission angle. They also face defects such as insufficient luminous efficiency and short lifespan, which restrict the upgrading of device performance.

[0004] To address the aforementioned issues of light extraction efficiency and lifespan, existing capping layer solutions still have several shortcomings: poor stability, volatile evaporation processes, and tendency for post-deposition crystallization, further impacting device reliability and lifespan; and difficulty in balancing the evaporation temperature and refractive index of the capping layer material, resulting in limited improvement in light extraction efficiency. Therefore, developing a capping layer material that combines high stability, compatibility with evaporation processes, and simultaneous improvement in light extraction efficiency and viewing distortion has become a crucial and inevitable requirement for driving the technological upgrade of top-emitting OLED devices. Summary of the Invention

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

[0006] This invention provides a carbazole-containing compound having the structure represented by Formula I:

[0007]

[0008] X is selected from O, S, or N (R0);

[0009] The Y is selected from O, S or N (R4);

[0010] The z is independently selected from C (R2) or N, and when z is bonded to other groups, the z is selected from C atoms;

[0011] The v is independently selected from CH or N, and when v is bonded to other groups, the v is selected from C atoms;

[0012] The x is independently selected from C (R5) or N, and when x is bonded to other groups, the x is selected from C atoms;

[0013] R0 and R4 are independently 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, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused cycloyl;

[0014] R1, R2, R3, R5, and R6 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, 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 R2, adjacent R3, and adjacent R5 can be interconnected to form one or more substituted or unsubstituted rings;

[0015] The q1 is selected from 0, 1, 2, 3 or 4; the q3 is selected from 0, 1 or 2;

[0016] The Ar is selected from 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, fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings, or any one of the following groups:

[0017]

[0018]

[0019]

[0020]

[0021] The e is independently selected from CH or N, and at least one e is selected from an N atom; when the e is bonded to other groups, the e is selected from a C atom.

[0022] The t is independently selected from CH or N, and when t is bonded to other groups, the t is selected from C atoms;

[0023] The W is selected from N(Rz);

[0024] W1 is selected from O, S or N (Rz);

[0025] Q1 is selected from O, S, N (Rz) or C (RxRy);

[0026] Q is selected from O or S;

[0027] 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, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused cycloyl;

[0028] 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, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or Rx and Ry can be interconnected to form substituted or unsubstituted rings;

[0029] 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 ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, or adjacent Rd can be interconnected to form one or more substituted or unsubstituted rings;

[0030] The Rd1 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;

[0031] 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;

[0032] The L1, L2, and L3 are independently selected from single bonds, Rm-substituted or unsubstituted groups as follows: C6-C30 arylene, C2-C30 heteroarylene, C3-C30 alicyclic and C6-C30 aromatic ring fused cycloalkanes;

[0033] The Rm is selected from 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 pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoleyl, substituted... It may be any one of the following: unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, fused cyclic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused cyclic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings, or adjacent Rm may be interconnected to form one or more substituted or unsubstituted rings.

[0034] 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 carbazole-containing compounds.

[0035] Beneficial effects: This invention provides a carbazole-containing compound that, when applied to a capping material, achieves a relative balance between evaporation temperature and refractive index, and possesses suitable molecular weight, evaporation temperature, sublimation temperature, and good stability, thereby improving and enhancing light extraction efficiency, while effectively increasing the luminous efficiency and lifespan of the device. Detailed Implementation

[0036] 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.

[0037] 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.

[0038] In this specification, " "This refers to the portion that is connected to another substituent."

[0039] 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.

[0040] 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 or ; Can represent , , And so on.

[0041] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, or iodine.

[0042] 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.

[0043] 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.

[0044] The "substituted or unsubstituted silyl group" mentioned in this invention refers to —Si(R k )3 groups, wherein each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl. Preferably, each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15, even more preferably 1 to 10, and most preferably 1 to 8. The cycloalkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 15, even more preferably 3 to 10, and most preferably 3 to 7. The aryl group preferably has 6 to 30 carbon atoms, more preferably 6 to 18, and particularly preferably 6 to 12. Preferably, each R... kThe same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Preferably, the "substituted or unsubstituted C3-C25 silyl" refers to a silyl group substituted with a substituted or unsubstituted C3-C25 alkyl or aryl group, preferably substituted with 3 alkyl or 3 aryl groups. Examples of “substituted or unsubstituted silyl groups”, especially “substituted or unsubstituted C3-C25 silyl groups”, may include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, etc.

[0045] 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 group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, tetraphenyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthrene, pyrene, peryl, thionyl, triphenylene, fluoranthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzo[a]fluorenyl, 9,9'-spirodifluorenyl, etc., but not limited to this.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] The arylene group described 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, phenanthrene, etc., but are not limited to these.

[0050] 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.

[0051] 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.

[0052] The fused ring groups of aromatic and aliphatic rings 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 can be described in the same way as the fused ring groups of aromatic and aliphatic rings described above.

[0053] 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.

[0054] 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 of the following: 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, and fused rings of substituted or unsubstituted C6-C30 aromatic rings and C3-C30 aliphatic rings. One preferred group includes deuterium, cyano, halogen atom, trifluoromethyl, C1-C12 alkyl, C3-C12 cycloalkyl, C3-C25 silyl, C6-C30 aryl, and C2-C30 heteroaryl. Specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and adamantyl. Norbornel, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, tolyl, pentadeuterated phenyl, naphthyl, anthracene, phenanthrene, pyrene, triphenylene, phenyl, peryl, fluoranyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, carbazole, 9-phenylcarbazole, 9,9'-spirodifluorenyl, benzocyclopropane Benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, pyrroleyl, furanyl, thiophenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, phenothiazinyl, phenothiazinyl, acridineyl, etc., but not limited to these.

[0055] 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:

[0056] .

[0057] 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.

[0058] This invention provides a carbazole-containing compound having the structure represented by Formula I:

[0059]

[0060] X is selected from O, S, or N (R0);

[0061] The Y is selected from O, S or N (R4);

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

[0063] The v is independently selected from CH or N, and when v is bonded to other groups, the v is selected from C atoms;

[0064] The x is independently selected from C (R5) or N, and when x is bonded to other groups, the x is selected from C atoms;

[0065] R0 and R4 are independently 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, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused cycloyl;

[0066] R1, R2, R3, R5, and R6 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, 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 R2, adjacent R3, and adjacent R5 can be interconnected to form one or more substituted or unsubstituted rings;

[0067] The q1 is selected from 0, 1, 2, 3 or 4; the q3 is selected from 0, 1 or 2;

[0068] The Ar is selected from 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, fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings, or any one of the following groups:

[0069]

[0070]

[0071]

[0072]

[0073] The e is independently selected from CH or N, and at least one e is selected from an N atom; when the e is bonded to other groups, the e is selected from a C atom.

[0074] The t is independently selected from CH or N, and when t is bonded to other groups, the t is selected from C atoms;

[0075] The W is selected from N(Rz);

[0076] W1 is selected from O, S or N (Rz);

[0077] Q1 is selected from O, S, N (Rz) or C (RxRy);

[0078] Q is selected from O or S;

[0079] 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, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused cycloyl;

[0080] 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, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or Rx and Ry can be interconnected to form substituted or unsubstituted rings;

[0081] 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 ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl, or adjacent Rd can be interconnected to form one or more substituted or unsubstituted rings;

[0082] The Rd1 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;

[0083] 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;

[0084] The L1, L2, and L3 are independently selected from single bonds, Rm-substituted or unsubstituted groups as follows: C6-C30 arylene, C2-C30 heteroarylene, C3-C30 alicyclic and C6-C30 aromatic ring fused cycloalkanes;

[0085] The Rm is selected from 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 pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoleyl, substituted... It may be any one of the following: unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, fused cyclic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused cyclic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings, or adjacent Rm may be interconnected to form one or more substituted or unsubstituted rings.

[0086] Preferably, in Formula I, x is independently selected from C(R5), or one, two, three, four, five or six x are selected from N, and the rest are selected from C(R5). When x is bonded to other groups, x is selected from C atoms.

[0087] Preferably, the Selected from any one of the following groups:

[0088]

[0089] X1 is selected from O, S, C (ReRf) or N (Rg);

[0090] The x is independently selected from CH, or in each group there are 1, 2, 3, 4, 5 or 6 x selected from N, and the rest are selected from CH. When x is bonded to other groups, the x is selected from C atoms.

[0091] The Rg 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;

[0092] The Re and Rf are independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, or any of the following groups substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane. adamantyl, norbornel, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, or Re and Rf can be interconnected to form one or more substituted or unsubstituted rings.

[0093] Preferably, when Selected from In this case, Ar is selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, and L3 is selected from single bonds.

[0094] Preferably, the Selected from any one of the following groups:

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] The R0 is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene;

[0104] R1 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;

[0105] The R2 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 R2s may be linked together to form one or more substituted or unsubstituted rings;

[0106] The s0 is selected from 0, 1, 2 or 3; the s1 is selected from 0, 1 or 2; the s2 is selected from 0, 1, 2, 3, 4 or 5; the s3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0107] Preferably, the Selected from any one of the following groups:

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118] The R4 is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more deuterium, cyano, fluorine, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C15 alkyl, or C3-C15 cycloalkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene;

[0119] The R3 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 R3s may be linked together to form one or more substituted or unsubstituted rings;

[0120] The R6 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, 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;

[0121] 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; the q4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the q5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; and the q6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0122] Preferably, the Ar is selected from any one of the following groups:

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143] The t is independently selected from CH, or one, two or three ts in each group are selected from N, and the rest are selected from CH. When t is bonded to other groups, the t is selected from C atoms.

[0144] 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;

[0145] The Rd1 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, 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;

[0146] 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;

[0147] 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, 6, 7, 8, 9, or 10; a9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; a 10 Choose from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12.

[0148] Preferably, L1, L2, and L3 are independently selected from single bonds or any one of the following groups and combinations thereof:

[0149]

[0150]

[0151] The u is independently selected from CH or N, and when u is bonded to other groups, the u is selected from C atoms;

[0152] The T is selected from O, S, N (Rw) or C (RhRi);

[0153] 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 ring fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring fused cycloyl;

[0154] The ring K is selected from substituted or unsubstituted C3 to C30 alicyclic rings;

[0155] 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, and 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;

[0156] The Rm is independently selected from 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 pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoleyl, etc. Any one of the following: substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, fused cyclic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic ring, or adjacent Rm may be interconnected to form one or more substituted or unsubstituted rings;

[0157] The Rm1 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;

[0158] 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.

[0159] Preferably, L1, L2, and L3 are independently selected from single bonds or any one of the following groups and combinations thereof:

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166] The Rw is selected from hydrogen, deuterium, or any of the following groups substituted or unsubstituted with one or more 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, or adjacent Rws may be connected to each other to form one or more substituted or unsubstituted rings;

[0167] 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 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, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophene, or adjacent Rm may be connected to each other to form one or more substituted or unsubstituted rings;

[0168] The Rm1 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, 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;

[0169] p1 is selected from 0, 1, 2, 3 or 4; p2 is selected from 0, 1, 2 or 3; p3 is selected from 0, 1 or 2; p4 is selected from 0, 1, 2, 3, 4, 5 or 6; p5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; p6 is selected from 0, 1, 2, 3, 4 or 5.

[0170] Preferably, the carbazole-containing compound is selected from any one of the following structures:

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201] 。

[0202] The above lists some specific structural forms of carbazole-containing compounds represented by Formula I of the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in Formula I, with substituents as defined above, should be included.

[0203] 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 carbazole-containing compounds described in the present invention.

[0204] Preferably, the organic functional layer is located between the anode and the cathode, and the organic functional layer includes at least one of a hole transport region, a light-emitting layer, and an electron transport region.

[0205] Preferably, the hole transport region includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer.

[0206] Preferably, the hole transport layer includes a first hole transport layer and a second hole transport layer, wherein the first hole transport layer is located between the anode and the light-emitting layer, and the second hole transport layer is located between the first hole transport layer and the light-emitting layer.

[0207] Preferably, the light-emitting layer comprises a host material and a dopant material.

[0208] Preferably, the electron transport region comprises at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0209] 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 carbazole-containing compounds of the present invention.

[0210] 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:

[0211] 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.

[0212] 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.

[0213] 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.

[0214] 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: 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 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), carbazole derivatives, triarylamine derivatives, biphenyl diamine derivatives, anthraquinone compounds, polyaniline, polythiophene, etc., but is not limited thereto.

[0215] 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.

[0216] 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), 9,10-bis(1-naphthyl)anthracene (α-AND), 9,9'-(1,3-phenyl)bis-9H-carbazole (mCP), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 1,3,5-tris(9-carbazoleyl)benzene (TCP), etc., or the carbazole-containing compounds of this invention, but are not limited thereto.

[0217] The light-emitting layer doping materials of this invention are classified into blue light-emitting materials, green light-emitting materials, and red light-emitting materials. The light-emitting layer doping materials can be simple fluorescent or phosphorescent materials, or a combination of fluorescent and phosphorescent materials, selected from, but not limited to, 2,5,8,11-tetratert-butylperylene (TBPe), 9,10-bis[N-(p-tolyl)aniline]anthracene (TPA), bis(4,6-difluorophenylpyridine-C2,N)pyridinecarboxylated iridium (FIrpic), bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), tris(2-phenylpyridine)iridium (Ir(ppy)3), bis(1-phenylisoquinoline)(acetylacetone)iridium (Ir(piq)2(acac)).

[0218] 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.

[0219] 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: tris(8-hydroxyquinoline)aluminum(III) (Alq3), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 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), di(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), etc., but is not limited thereto.

[0220] 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, 8-hydroxyquinoline cesium), organometallic salts (metal acetate, metal benzoate or metal stearate), molybdenum trioxide, aluminum, etc., but are not limited thereto.

[0221] The cathode material of this 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.

[0222] The capping layer of 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 carbazole-containing compounds as described in this invention, but are not limited thereto.

[0223] 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.

[0224] 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.

[0225] The organic electroluminescent device of the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0226] 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.

[0227] This invention provides a method for preparing compounds represented by Formula I, which is carried out through carbon-nitrogen coupling and carbon-carbon coupling reactions 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:

[0228] 1. Preparation of intermediate c:

[0229]

[0230] 2. Preparation of Formula I:

[0231]

[0232] Among them, Xa, Xb, Xc, and Xd may be the same or different from each other, and are selected from any one of Cl, Br, and I; the limitations of X, Y, Ar, L1, L2, L3, R1, R3, R6, x, v, z, q1, and q3 are the same as those described above.

[0233] The substituents described above can be bonded using methods known in the art, and the type, position, or number of substituents can be changed according to techniques known in the art.

[0234] 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.

[0235] Preparation and characterization of compounds

[0236] Description of raw materials, reagents, and characterization equipment:

[0237] 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.

[0238] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0239] 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.

[0240] Synthesis Example 1: Preparation of Intermediate c-1

[0241]

[0242] Under nitrogen protection, starting material e-1 (20.23 g, 60.00 mmol), starting material f-1 (11.49 g, 60.00 mmol), K2CO3 (16.59 g, 120.00 mmol), and 300 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to the reaction flask. After purging the air with nitrogen three times, Pd(PPh3)4 (0.83 g, 0.72 mmol) was added. The mixture was stirred and heated under reflux for 5.0 hours. 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. After filtration, the solvent was concentrated by rotary evaporation, and crystals were precipitated by cooling and filtration. Then, the mixture was recrystallized from toluene / methanol at a ratio of 5:1 to obtain intermediate c-1 (15.06 g, yield 78%) with an HPLC purity ≥99.86%. Mass spectrometry m / z: 321.0363 (theoretical value: 321.0379).

[0243] Other intermediates required for the present invention were synthesized using the above-described synthesis method. The relevant raw materials are shown in Table 1.

[0244] Table 1:

[0245]

[0246]

[0247] Synthesis Example 2: Preparation of Compound 1

[0248]

[0249] Preparation of intermediate A-1:

[0250] Under nitrogen protection, starting material b-1 (16.25 g, 50 mmol), starting material a-1 (26.02 g, 100 mmol), and Pd(OAc)2 (0.28 g, 1.23 mmol) were added to DMF (346 mL), and the mixture was stirred. Then, K3PO4 aqueous solution (31.84 g, 150 mmol) was added, and the mixture was heated under reflux for 9 hours. After the reaction was completed, the mixture was cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, allowed to stand, and the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from ethyl acetate to obtain intermediate A-1 (16.62 g, 77%) with an HPLC purity of ≥99.86%. Mass spectrometry m / z: 431.0787 (theoretical value: 431.0802).

[0251] Preparation of compound 1:

[0252] Under nitrogen protection, intermediates A-1 (15.97 g, 37 mmol), c-1 (11.91 g, 37 mmol), and sodium tert-butoxide (8.84 g, 92 mmol) were added to 300 mL of toluene. Pd₂(dba)₃ (0.28 g, 0.31 mmol) and P(t-Bu)₃ (1.23 mL of 0.5 M toluene solution, 0.62 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 10 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. After standing and separation, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from toluene to give compound 1 (19.10 g, yield 72%), with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 716.1429 (theoretical value: 716.1415). Theoretical element content (%) C 47 H 28 N₂S₃: C, 78.74; H, 3.94; N, 3.91. Measured elemental content (%): C, 78.79; H, 3.97; N, 3.95.

[0253] Synthesis Example 3: Preparation of Compound 17

[0254]

[0255] According to the preparation method in Example 2, b-1 was replaced with an equimolar amount of b-17 to obtain compound 17 (19.36 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 716.1431. Theoretical value: (716.1415). Theoretical elemental content (%) C 47 H 28 N2S3: C, 78.74; H, 3.94; N, 3.91. Measured elemental content (%): C, 78.77; H, 3.98; N, 3.96.

[0256] Synthesis Example 4: Preparation of Compound 25

[0257]

[0258] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-25, and c-1 was replaced with an equimolar amount of c-25 to obtain compound 25 (24.12 g). HPLC analysis showed that the solid purity was ≥99.99%. Mass spectrometry m / z: 868.2052 (theoretical value: 868.2041). Theoretical elemental content (%) C 59 H 36N2S3: C, 81.54; H, 4.18; N, 3.22. Measured elemental content (%): C, 81.58; H, 4.23; N, 3.26.

[0259] Synthesis Example 5: Preparation of Compound 54

[0260]

[0261] Preparation of intermediate A-54:

[0262] Under nitrogen protection, starting materials a-25 (23.54 g, 70 mmol), b-54 (19.64 g, 70 mmol), and Pd(OAc)2 (0.16 g, 0.70 mmol) were added to DMF (460 mL), and the mixture was stirred. Then, K3PO4 aqueous solution (22.29 g, 105 mmol) was added, and the mixture was heated under reflux for 7 hours. After the reaction was completed, the mixture was cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, allowed to stand, and separated. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from ethyl acetate to obtain intermediate A-54 (23.53 g, 82%) with an HPLC purity of ≥99.85%. Mass spectrometry m / z: 409.0679 (theoretical value: 409.0692).

[0263] Preparation of intermediate B-54:

[0264] Under nitrogen protection, starting materials A-54 (22.55 g, 55 mmol), d-54 (18.49 g, 55 mmol), and Pd(OAc)2 (0.12 g, 0.55 mmol) were added to DMF (360 mL), and the mixture was stirred. Then, K3PO4 aqueous solution (17.62 g, 83 mmol) was added, and the mixture was heated under reflux for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, allowed to stand, and separated. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from ethyl acetate to obtain intermediate B-54 (25.04 g, 78%) with an HPLC purity of ≥99.82%. Mass spectrometry m / z: 583.1441 (theoretical value: 583.1428).

[0265] Preparation of compound 54:

[0266] Under nitrogen protection, intermediates B-54 (21.60 g, 37 mmol), c-54 (10.74 g, 37 mmol), and sodium tert-butoxide (5.38 g, 56 mmol) were added to 165 mL of toluene. Pd2(dba)3 (0.34 g, 0.37 mmol) and P(t-Bu)3 (0.98 mL of 0.5 M toluene solution, 0.43 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 8 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. After standing and separation, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from toluene to give compound 54 (21.71 g, yield 74%), with an HPLC purity ≥99.96%. Mass spectrometry m / z: 792.1743 (theoretical value: 792.1728). Theoretical element content (%) C 53 H 32 N₂S₃: C, 80.27; H, 4.07; N, 3.53. Measured elemental content (%): C, 80.32; H, 4.12; N, 3.59.

[0267] Synthesis Example 6: Preparation of Compound 63

[0268]

[0269] According to the preparation method in Example 2, c-1 was replaced with an equimolar amount of c-63 to obtain compound 63 (19.74 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 720.1690 (theoretical value: 720.1666). Theoretical elemental content (%) C 47 H 24 D4N2S3: C, 78.30; H, 4.47; N, 3.89. Measured elemental content (%): C, 78.34; H, 4.52; N, 3.93.

[0270] Synthesis Example 7: Preparation of Compound 64

[0271]

[0272] According to the preparation method in Synthesis Example 2, c-1 was replaced with an equimolar amount of c-64 to obtain compound 64 (20.43 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 766.1559 (theoretical value: 766.1571). Theoretical elemental content (%) C 51 H 30N2S3: C, 79.87; H, 3.94; N, 3.65. Measured elemental content (%): C, 79.82; H, 3.90; N, 3.63.

[0273] Synthesis Example 8: Preparation of Compound 71

[0274]

[0275] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-71 to obtain compound 71 (23.69 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 876.2555 (theoretical value: 876.2543). Theoretical elemental content (%) C 59 H 28 D8N2S3: C, 80.79; H, 5.05; N, 3.19. Measured elemental content (%): C, 80.82; H, 5.09; N, 3.22.

[0276] Synthesis Example 9: Preparation of Compound 72

[0277]

[0278] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-72 to obtain compound 72 (23.21 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 870.1934 (theoretical value: 870.1946). Theoretical elemental content (%) C 57 H 34 N4S3: C, 78.59; H, 3.93; N, 6.43. Measured elemental content (%): C, 78.53; H, 3.89; N, 6.39.

[0279] Synthesis Example 10: Preparation of Compound 85

[0280]

[0281] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-85 to obtain compound 85 (18.75 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 684.1885 (theoretical value: 684.1871). Theoretical elemental content (%) C 47 H 28 N2O2S: C, 82.43; H, 4.12; N, 4.09. Measured elemental content (%): C, 82.47; H, 4.18; N, 4.13.

[0282] Synthetic Example 11: Preparation of Compound 139

[0283]

[0284] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-139 to obtain compound 139 (25.31 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 936.2816 (theoretical value: 936.2810). Theoretical elemental content (%) C 67 H 40 N2O2S: C, 85.87; H, 4.30; N, 2.99. Measured elemental content (%): C, 85.92; H, 4.35; N, 3.04.

[0285] Synthesis Example 12: Preparation of Compound 140

[0286]

[0287] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-140, and c-1 was replaced with an equimolar amount of c-140 to obtain compound 140 (22.61 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 836.2484 (theoretical value: 836.2497). Theoretical elemental content (%) C 59 H 36 N2O2S: C, 84.66; H, 4.34; N, 3.35. Measured elemental content (%): C, 84.62; H, 4.30; N, 3.31.

[0288] Synthesis Example 13: Preparation of Compound 237

[0289]

[0290] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-237, and c-1 was replaced with an equimolar amount of c-237 to obtain compound 237 (18.56 g). HPLC analysis showed that the solid purity was ≥99.99%. Mass spectrometry m / z: 668.2112 (theoretical value: 668.2100). Theoretical elemental content (%) C 47 H 28 N2O3: C, 84.41; H, 4.22; N, 4.19. Measured elemental content (%): C, 84.45; H, 4.26; N, 4.23.

[0291] Synthesis Example 14: Preparation of Compound 247

[0292]

[0293] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-247, b-1 with an equimolar amount of b-247, and c-1 with an equimolar amount of c-247, yielding compound 247 (19.84 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 744.2401 (theoretical value: 744.2413). Theoretical elemental content (%) C 53 H 32 N2O3: C, 85.46; H, 4.33; N, 3.76. Measured elemental content (%): C, 85.42; H, 4.29; N, 3.72.

[0294] Synthesis Example 15: Preparation of Compound 280

[0295]

[0296] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-85, and c-1 was replaced with an equimolar amount of c-280, yielding compound 280 (18.09 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 669.2063 (theoretical value: 669.2052). Theoretical elemental content (%) C 46 H 27 N3O3: C, 82.50; H, 4.06; N, 6.27. Measured elemental content (%): C, 82.54; H, 4.10; N, 6.31.

[0297] Synthesis Example 16: Preparation of Compound 299

[0298]

[0299] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-1, d-54 was replaced with an equimolar amount of a-85, and c-54 was replaced with an equimolar amount of c-299, yielding compound 299 (16.89 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 608.1571 (theoretical value: 608.1558). Theoretical elemental content (%) C 41 H 24 N2O2S: C, 80.90; H, 3.97; N, 4.60. Measured elemental content (%): C, 80.96; H, 4.03; N, 4.66.

[0300] Synthesis Example 17: Preparation of Compound 340

[0301]

[0302] According to the preparation method in Synthesis Example 2, c-1 was replaced with an equimolar amount of c-340 to obtain compound 340 (19.13 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 717.1352 (theoretical value: 717.1367). Theoretical elemental content (%) C 46 H 27 N3S3: C, 76.96; H, 3.79; N, 5.85. Measured elemental content (%): C, 76.92; H, 3.75; N, 5.81.

[0303] Synthesis Example 18: Preparation of Compound 345

[0304]

[0305] According to the preparation method in Synthesis Example 2, a-1 was replaced with an equimolar amount of a-345 to obtain compound 345 (18.89 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 718.1306 (theoretical value: 718.1320). Theoretical elemental content (%) C 45 H 26 N4S3: C, 75.18; H, 3.65; N, 7.79. Measured elemental content (%): C, 75.15; H, 3.62; N, 7.76.

[0306] Synthesis Example 19: Preparation of Compound 407

[0307]

[0308] According to the preparation method in Synthesis Example 2, c-1 was replaced with an equimolar amount of c-407 to obtain compound 407 (19.31 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 724.1630 (theoretical value: 724.1643). Theoretical elemental content (%) C 49 H 28 N2OS2: C, 81.19; H, 3.89; N, 3.86. Measured elemental content (%): C, 81.13; H, 3.83; N, 3.80.

[0309] Synthesis Example 20: Preparation of Compound 419

[0310]

[0311] According to the preparation method in Example 2, a-1 was replaced with an equimolar amount of a-419, and c-1 was replaced with an equimolar amount of c-419, yielding a compound (18.71 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 692.2115 (theoretical value: 692.2100). Theoretical elemental content (%) C 49 H 28 N2O3: C, 84.95; H, 4.07; N, 4.04. Measured elemental content (%): C, 84.98; H, 4.10; N, 4.07.

[0312] Synthesis Example 21: Preparation of Compound 453

[0313]

[0314] Preparation of intermediate A-453:

[0315] Under nitrogen protection, starting material a-1 (13.01 g, 50 mmol), starting material b-453 (12.31 g, 50 mmol), and Pd(OAc)2 (0.21 g, 0.92 mmol) were added to DMF (270 mL), and the mixture was stirred. Then, K3PO4 aqueous solution (24.41 g, 115 mmol) was added, and the mixture was heated under reflux for 7 hours. After the reaction was completed, the mixture was cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, allowed to stand, and separated. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, and the solid was filtered. The obtained solid was recrystallized from ethyl acetate to obtain intermediate A-453 (11.68 g, 78%) with an HPLC purity of ≥99.83%. Mass spectrometry m / z: 299.0752 (theoretical value: 299.0769).

[0316] Preparation of compound 453:

[0317] Under nitrogen protection, intermediates A-453 (11.08 g, 37 mmol), c-1 (11.91 g, 37 mmol), and sodium tert-butoxide (8.87 g, 92.31 mmol) were added to 230 mL of toluene. Pd2(dba)3 (0.28 g, 0.31 mmol) and P(t-Bu)3 (1.23 mL of 0.5 M toluene solution, 0.62 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 10 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. After standing and separation, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from toluene to give compound 453 (15.58 g, yield 72%) with an HPLC purity ≥ 99.99%. Mass spectrometry m / z: 584.1370 (theoretical value: 584.1381). Theoretical elemental content (%) C 39 H 24 N2S2: C, 80.11; H, 4.14; N, 4.79. Measured elemental content (%): C, 80.06; H, 4.10; N, 4.76.

[0318] Synthesis Example 22: Preparation of Compound 461

[0319]

[0320] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-1, d-54 was replaced with an equimolar amount of d-461, and c-54 was replaced with an equimolar amount of c-1 to obtain compound 461 (17.31 g). HPLC analysis showed that the solid purity was ≥99.98%. Mass spectrometry m / z: 640.2019 (theoretical value: 640.2007). Theoretical elemental content (%) C 43 H 32 N2S2: C, 80.59; H, 5.03; N, 4.37. Measured elemental content (%): C, 80.62; H, 5.06; N, 4.40.

[0321] Synthesis Example 23: Preparation of Compound 467

[0322]

[0323] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-1, d-54 was replaced with an equimolar amount of d-467, and c-54 was replaced with an equimolar amount of c-1, yielding compound 467 (18.34 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 660.1710 (theoretical value: 660.1694). Theoretical elemental content (%) C45 H 28 N2S2: C, 81.79; H, 4.27; N, 4.24. Measured elemental content (%): C, 81.82; H, 4.30; N, 4.27.

[0324] Synthesis Example 24: Preparation of Compound 480

[0325]

[0326] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-1, d-54 was replaced with an equimolar amount of d-480, and c-54 was replaced with an equimolar amount of c-1 to obtain compound 480 (20.00 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 750.1212 (theoretical value: 750.1223). Theoretical elemental content (%) C 45 H 23 F5N2S2: C, 71.99; H, 3.09; N, 3.73. Measured elemental content (%): C, 71.96; H, 3.06; N, 3.70.

[0327] Synthesis Example 25: Preparation of Compound 482

[0328]

[0329] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-1, d-54 was replaced with an equimolar amount of d-482, and c-54 was replaced with an equimolar amount of c-1, yielding compound 482 (19.46 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 710.1839 (theoretical value: 710.1850). Theoretical elemental content (%) C 49 H 30 N2S2: C, 82.79; H, 4.25; N, 3.94. Measured elemental content (%): C, 82.75; H, 4.21; N, 3.90.

[0330] Synthesis Example 26: Preparation of Compound 566

[0331]

[0332] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-566, d-54 was replaced with an equimolar amount of d-566, and c-54 was replaced with an equimolar amount of c-566, yielding compound 566 (16.62 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 623.1956 (theoretical value: 623.1969). Theoretical elemental content (%) C 42 H 21 D4N3OS: C, 80.87; H, 4.69; N, 6.74. Measured elemental content (%): C, 80.82; H, 4.64; N, 6.69.

[0333] Synthesis Example 27: Preparation of Compound 596

[0334]

[0335] According to the preparation method in Synthesis Example 21, b-453 was replaced with an equimolar amount of b-596 to obtain compound 596 (16.04 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 585.1321 (theoretical value: 585.1333). Theoretical elemental content (%) C 38 H 23 N3S2: C, 77.92; H, 3.96; N, 7.17. Measured elemental content (%): C, 77.89; H, 3.93; N, 7.14.

[0336] Synthesis Example 28: Preparation of Compound 643

[0337]

[0338] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-85, d-54 was replaced with an equimolar amount of d-643, and c-54 was replaced with an equimolar amount of c-1, yielding compound 643 (21.47 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 794.2381 (theoretical value: 794.2392). Theoretical elemental content (%) C 57 H 34 N₂OS: C, 86.12; H, 4.31; N, 3.52. Measured elemental content (%): C, 86.09; H, 4.28; N, 3.49.

[0339] Synthesis Example 29: Preparation of Compound 681

[0340]

[0341] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-85, d-54 was replaced with an equimolar amount of d-681, and c-54 was replaced with an equimolar amount of c-1, yielding compound 681 (19.85 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 734.2016 (theoretical value: 734.2028). Theoretical elemental content (%) C 51 H 30 N2O2S: C, 83.36; H, 4.11; N, 3.81. Measured elemental content (%): C, 83.32; H, 4.07; N, 3.77.

[0342] Synthesis Example 30: Preparation of Compound 685

[0343]

[0344] According to the preparation method in Synthesis Example 21, b-453 was replaced with an equimolar amount of b-685 to obtain compound 685 (15.34 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 575.2060 (theoretical value: 575.2049). Theoretical elemental content (%) C 39 H 17 D7N2OS: C, 81.36; H, 5.43; N, 4.87. Measured elemental content (%): C, 81.32; H, 5.39; N, 4.83.

[0345] Synthesis Example 31: Preparation of Compound 707

[0346]

[0347] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-707, d-54 was replaced with an equimolar amount of d-707, and c-54 was replaced with an equimolar amount of c-707, yielding compound 707 (17.55 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 649.2225 (theoretical value: 649.2236). Theoretical elemental content (%) C 45 H 23 D5N2OS: C, 83.18; H, 5.12; N, 4.31. Measured elemental content (%): C, 83.15; H, 5.09; N, 4.28.

[0348] Synthesis Example 32: Preparation of Compound 727

[0349]

[0350] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-1, d-54 was replaced with an equimolar amount of d-727, and c-54 was replaced with an equimolar amount of c-727, yielding compound 727 (22.18 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 820.2540 (theoretical value: 820.2548). Theoretical elemental content (%) C 59 H 36 N₂OS: C, 86.31; H, 4.42; N, 3.41. Measured elemental content (%): C, 86.30; H, 4.40; N, 3.43.

[0351] Synthesis Example 33: Preparation of Compound 767

[0352]

[0353] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-1, d-54 was replaced with an equimolar amount of d-767, and c-54 was replaced with an equimolar amount of c-237, yielding compound 767 (19.03 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 685.1836 (theoretical value: 685.1824). Theoretical elemental content (%) C 46 H 27 N3O2S: C, 80.56; H, 3.97; N, 6.13. Measured elemental content (%): C, 80.60; H, 4.01; N, 6.17.

[0354] Synthesis Example 34: Preparation of Compound 795

[0355]

[0356] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-85, d-54 with an equimolar amount of d-795, and c-54 with an equimolar amount of c-795, yielding compound 795 (20.01 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 750.2719 (theoretical value: 750.2703). Theoretical elemental content (%) C 52 H 38 N2O2Si: C, 83.17; H, 5.10; N, 3.73. Measured elemental content (%): C, 83.16; H, 5.13; N, 3.76.

[0357] Synthesis Example 35: Preparation of Compound 802

[0358]

[0359] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-802, d-54 was replaced with an equimolar amount of d-802, and c-54 was replaced with an equimolar amount of c-707, yielding compound 802 (22.35 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 838.3547 (theoretical value: 838.3559). Theoretical elemental content (%) C 61 H 46 N2O2: C, 87.32; H, 5.53; N, 3.34. Measured elemental content (%): C, 87.30; H, 5.51; N, 3.32.

[0360] Synthesis Example 36: Preparation of Compound 916

[0361]

[0362] According to the preparation method in Synthesis Example 21, b-453 was replaced with an equimolar amount of b-916, and c-1 was replaced with an equimolar amount of c-25, yielding compound 916 (16.91 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 634.1525 (theoretical value: 634.1537). Theoretical elemental content (%) C 43 H 26 N2S2: C, 81.36; H, 4.13; N, 4.41. Measured elemental content (%): C, 81.38; H, 4.15; N, 4.43.

[0363] Synthesis Example 37: Preparation of Compound 923

[0364]

[0365] According to the preparation method in Synthesis Example 21, b-453 was replaced with an equimolar amount of b-923, and c-1 was replaced with an equimolar amount of c-707, yielding compound 923 (17.55 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 658.1702 (theoretical value: 658.1715). Theoretical elemental content (%) C 45 H 26 N2O2S: C, 82.05; H, 3.98; N, 4.25. Measured elemental content (%): C, 82.01; H, 3.94; N, 4.21.

[0366] Synthesis Example 38: Preparation of Compound 951

[0367]

[0368] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-1, d-54 was replaced with an equimolar amount of d-951, and c-54 was replaced with an equimolar amount of c-951, yielding compound 951 (17.55 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 649.1566 (theoretical value: 649.1556). Theoretical elemental content (%) C 40 H 15 D8N3S3: C, 73.93; H, 4.81; N, 6.47. Measured elemental content (%): C, 73.96; H, 4.84; N, 6.50.

[0369] Synthesis Example 39: Preparation of Compound 953

[0370]

[0371] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-1, d-54 was replaced with an equimolar amount of d-953, and c-54 was replaced with an equimolar amount of c-953, yielding compound 953 (16.16 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 606.1755 (theoretical value: 606.1766). Theoretical elemental content (%) C 42 H 26 N₂OS: C, 83.14; H, 4.32; N, 4.62. Measured elemental content (%): C, 83.11; H, 4.29; N, 4.68.

[0372] Synthesis Example 40: Preparation of Compound 955

[0373]

[0374] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-955, d-54 was replaced with an equimolar amount of d-955, and c-54 was replaced with an equimolar amount of c-955, yielding compound 955 (18.85 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 697.2714 (theoretical value: 697.2729). Theoretical elemental content (%) C 49 H 35 N3O2: C, 84.34; H, 5.06; N, 6.02. Measured elemental content (%): C, 84.31; H, 5.03; N, 6.00.

[0375] Synthetic Example 41: Preparation of Compound 956

[0376]

[0377] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-1, d-54 was replaced with an equimolar amount of d-956, and c-54 was replaced with an equimolar amount of c-956, yielding compound 956 (19.79 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 742.2067 (theoretical value: 742.2079). Theoretical elemental content (%) C 53 H 30 N₂OS: C, 85.69; H, 4.07; N, 3.77. Measured elemental content (%): C, 85.63; H, 4.01; N, 3.72.

[0378] Synthesis Example 42: Preparation of Compound 989

[0379]

[0380] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-85, d-54 with an equimolar amount of d-989, and c-54 with an equimolar amount of c-989, yielding compound 989 (21.75 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 827.2925 (theoretical value: 827.2937). Theoretical elemental content (%) C 61 H 37 N3O: C, 88.49; H, 4.50; N, 5.08. Measured elemental content (%): C, 88.43; H, 4.44; N, 5.02.

[0381] Synthesis Example 43: Preparation of Compound 990

[0382]

[0383] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-990, d-54 was replaced with an equimolar amount of d-990, and c-54 was replaced with an equimolar amount of c-990, yielding compound 990 (25.21 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 945.3189 (theoretical value: 945.3178). Theoretical elemental content (%) C 69 H 43 N3S: C, 87.59; H, 4.58; N, 4.44. Measured elemental content (%): C, 87.55; H, 4.54; N, 4.40.

[0384] Synthesis Example 43: Preparation of Compound 1005

[0385]

[0386] Following the preparation method of Synthesis Example 21, b-453 was replaced with an equimolar amount of b-1005, and c-1 was replaced with an equimolar amount of c-1005, yielding compound 923 (19.42 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 749.1950 (theoretical value: 749.1959). Theoretical elemental content (%) C 51 H 31 N3S2: C, 81.68; H, 4.17; N, 5.60. Measured elemental content (%): C, 81.64; H, 4.13; N, 5.65.

[0387] Synthesis Example 44: Preparation of Compound 1041

[0388]

[0389] According to the preparation method in Synthesis Example 5, a-25 was replaced with an equimolar amount of a-1, d-54 was replaced with an equimolar amount of d-1041, and c-54 was replaced with an equimolar amount of c-25, yielding compound 1041 (18.98 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 702.1530 (theoretical value: 702.1548). Theoretical elemental content (%) C 45 H 26 N4OS2: C, 76.90; H, 3.73; N, 7.97. Measured elemental content (%): C, 76.93; H, 3.71; N, 7.96.

[0390] Device Examples

[0391] 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.

[0392] 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. 2The luminous efficiency and driving voltage were measured. Using McScience's M6000 OLED lifetime testing system, the lifetime of the device prepared in this invention (brightness decaying to 95% of initial brightness) was tested at atmospheric pressure and room temperature, with a test current density of 10 mA / cm². 2 .

[0393] [Device Example 1]

[0394] 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.

[0395] An organic electroluminescent device was fabricated by vacuum evaporation on a cleaned ITO / Ag / ITO substrate. The following layers were deposited sequentially: hole injection layer HI-1 (10 nm); hole transport layer HT-1 (100 nm); light-emitting layer RH-1:RH-2:RD-1=48:48:4 (mass ratio, 30 nm); electron transport layer ET-1:Liq=1:1 (mass ratio, 35 nm); electron injection layer LiF (0.8 nm); cathode Mg:Ag=1:9 (mass ratio, 10 nm); and capping layer compound 1 (90 nm).

[0396]

[0397] [Device Examples 2-43]

[0398] Compounds 17, 25, 54, 63, 64, 71, 72, 85, 139, 140, 237, 247, 280, 299, 340, 345, 407, 419, 453, 461, 467, 480, 482, 566, 596, 643, 681, 685, 707, 727, 767, 795, 802, 916, 923, 951, 953, 955, 956, 989, 990, and 1041 of the present invention were used to replace compound 1 in device example 1 as the capping layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 1.

[0399] [Comparative Device Examples 1-5]

[0400] Comparative compounds 1, 2, 3, 4, and 5 were used to replace compound 1 in device example 1 as the capping material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 1.

[0401] The luminescence characteristics test results of the organic electroluminescent devices obtained in Embodiments 1-43 and Comparative Embodiments 1-5 of the present invention are shown in Table 1 below.

[0402]

[0403] As can be seen from the data in Table 1, the application of the carbazole-containing compound described in this invention as a capping material in organic electroluminescent devices exhibits good thermal stability, resulting in excellent luminous efficiency and lifespan for the devices.

[0404] 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 carbazole-containing compound, characterized by, The carbazole-containing compound has the structure represented by Formula I: Selected from any one of the following groups: R0 is selected from any one of the following groups that are substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl, C1-C6 alkyl, or C3-C10 cycloalkyl: phenyl, biphenyl, naphthyl; R1 is selected from hydrogen, deuterium, fluorine, cyano, or any of the following groups substituted or unsubstituted by one or more deuterium or fluorine: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; or any of the following groups substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl, C1-C6 alkyl, C3-C10 cycloalkyl: phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl; R2 is independently selected from hydrogen, deuterium, fluorine, cyano, or any of the following groups substituted or unsubstituted by one or more deuterium or fluorine groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; s0 is selected from 0, 1, 2 or 3; s1 is selected from 0, 1 or 2; s2 is selected from 0, 1, 2, 3, 4 or 5; s3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; Selected from any one of the following groups: R4 is selected from any one of the following groups that are substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl, C1-C6 alkyl, or C3-C10 cycloalkyl: phenyl, biphenyl, naphthyl; R3 is independently selected from hydrogen, deuterium, fluorine, cyano, or any of the following groups substituted or unsubstituted by one or more deuterium or fluorine groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl; R6 is independently selected from any one of the following groups: hydrogen, deuterium, fluorine, cyano, or substituted or unsubstituted by one or more deuterium or fluorine groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl; q1 is selected from 0, 1, 2, 3 or 4; q2 is selected from 0, 1, 2 or 3; q3 is selected from 0, 1 or 2; q4 is selected from 0, 1, 2, 3, 4, 5 or 6; Selected from any one of the following groups: X1 is selected from O, S, C (ReRf) or N (Rg); x is independently selected from CH, or one or two x in each group are selected from N, and the rest are selected from CH; when x is bonded to other groups, x is selected from C atoms. Rg is selected from any one of the following groups that are substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl, C1-C6 alkyl, or C3-C10 cycloalkyl: phenyl, biphenyl, naphthyl; Re and Rf are independently selected from any one of the following groups that are substituted or unsubstituted by one or more deuterium or fluorine: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; or any one of the following groups that are substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl, C1-C6 alkyl, C3-C10 cycloalkyl: phenyl, biphenyl, naphthyl; Ar is selected from hydrogen, deuterium, fluorine, trifluoromethyl, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, or any one of the following groups: t is independently selected from CH, or one or two t in each group are selected from N, and the rest are selected from CH; when t is bonded to other groups, the t is selected from C atoms. Rd1 is independently selected from any one of the following groups: hydrogen, deuterium, fluorine, cyano, or substituted or unsubstituted by one or more deuterium or fluorine groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilane, triethylsilane, tritert-butylsilane, triphenylsilane, phenyl; Rd is independently selected from any one of the following groups: hydrogen, deuterium, fluorine, cyano, or substituted or unsubstituted by one or more deuterium or fluorine groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl; or Two adjacent Rd atoms are interconnected to form one or more substituted or unsubstituted rings: benzene ring, naphthalene ring; or The two adjacent Rd rings in the middle form one or more substituted or unsubstituted benzene 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; L1, L2, and L3 are independently selected from any one of the single bonds or groups shown below and combinations thereof: Rm is independently selected from any one of the following groups: hydrogen, deuterium, fluorine, cyano, or substituted or unsubstituted by one or more deuterium or fluorine groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl; 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; In Ar, "substituted or unsubstituted C1-C6 alkyl or substituted or unsubstituted C3-C10 cycloalkyl", the substituents in "substituted or unsubstituted" are the same or different from each other, and are selected from deuterium, fluorine, chlorine, bromine, and iodine.

2. The carbazole-containing compound according to claim 1, characterized in that, Selected from any one of the following groups: X1 is selected from O, S, or N (Rg); x is independently selected from CH, or one x in each group is selected from N, and the rest are selected from CH; when x is bonded to other groups, x is selected from C atoms. Rg is selected from any one of the following groups that are substituted or unsubstituted by one or more deuterium, cyano, fluorine, trifluoromethyl, or C1-C6 alkyl groups: phenyl, biphenyl, naphthyl.

3. The carbazole-containing compound according to claim 1, characterized in that, Selected from any one of the following groups: R0 is selected from any one of the following groups that are substituted or unsubstituted by one or more deuterium, fluorine, trifluoromethyl, or C1-C6 alkyl groups: phenyl, biphenyl, naphthyl; R1 is selected from any one of the following groups: hydrogen, deuterium, fluorine, or substituted or unsubstituted by one or more deuterium or fluorine: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; or substituted or unsubstituted by one or more deuterium, fluorine, trifluoromethyl, or C1-C6 alkyl groups: phenyl, biphenyl, naphthyl, pyridyl; R2 is independently selected from hydrogen, deuterium, fluorine, cyano, or any of the following groups substituted or unsubstituted with one or more deuterium or fluorine groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl.

4. The carbazole-containing compound according to claim 1, characterized in that, Selected from any one of the following groups: R4 is selected from any one of the following groups that are substituted or unsubstituted by one or more deuterium, fluorine, trifluoromethyl, or C1-C6 alkyl groups: phenyl, biphenyl, naphthyl; R3 is independently selected from hydrogen, deuterium, fluorine, cyano, or any of the following groups substituted or unsubstituted by one or more deuterium or fluorine groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; R6 is independently selected from any one of the following groups: hydrogen, deuterium, fluorine, cyano, or substituted or unsubstituted by one or more deuterium or fluorine groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl.

5. The carbazole-containing compound according to claim 1, characterized in that, Ar is selected from any of the following groups: t is independently selected from CH, or one t in each group is selected from N and the rest are selected from CH, and when t is bonded to other groups, the t is selected from C atoms; Rd1 is independently selected from any one of the following groups: hydrogen, deuterium, fluorine, or substituted or unsubstituted by one or more deuterium or fluorine groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, adamantyl, trimethylsilyl, triethylsilyl, tritert-butylsilyl, phenyl. Rd is independently selected from any one of the following groups: hydrogen, deuterium, fluorine, or substituted or unsubstituted by one or more deuterium or fluorine groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, adamantyl, trimethylsilyl, triethylsilyl, tritert-butylsilyl, phenyl.

6. The carbazole-containing compound according to claim 1, characterized in that, L1, L2, and L3 are independently selected from any one of the single bonds or groups shown below and combinations thereof: Rm is independently selected from any one of the following groups: hydrogen, deuterium, fluorine, or substituted or unsubstituted by one or more deuterium or fluorine groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl.

7. A carbazole-containing compound, characterized in that, The carbazole-containing 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 carbazole-containing compounds described in any one of claims 1 to 7.

9. 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 coating layer comprises any one or more of the carbazole-containing compounds according to any one of claims 1 to 7.

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