Carbazole compound and organic electroluminescent device thereof

Abstract

The invention provides a carbazole compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic photoelectric materials. The carbazole compound provided by the invention has good carrier transport performance and stability when being used in a light-emitting layer in a device, so that the light-emitting efficiency of the device is effectively improved, and the service life of the device is prolonged. When the compound is applied to a covering layer in a device, the compound has good refractive index and good chemical stability, the luminous efficiency of the device can be effectively improved, and the service life of the device is prolonged. The preparation method of the compound is simple, raw materials are easy to obtain, and the compound can be widely applied to the fields of organic thin film transistors, panel display and the like and has good application effects and industrialization prospects.

Description

Technical Field

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

[0002] In the 21st century, display devices, as carriers of human-computer interaction, have become an important part of the electronic information industry, indicating that display technology has become a crucial link in information technology. With social development and technological progress, consumers' demands for the color performance and practicality of display devices are constantly increasing, especially in terms of high definition, high-quality imaging, wide color gamut, full-color display, flexibility and foldability, and long lifespan. Traditional cathode ray tube displays (CRTs) and liquid crystal displays (LCDs) relying on backlight modules can no longer meet these demands; therefore, organic light-emitting diode (OLED) display technology, based on organic semiconductor materials, has emerged. Compared to CRTs and LCDs, OLED displays have advantages such as high luminous efficiency, high contrast, low power consumption, wide viewing angle, short response time, and light weight. OLED has become one of the most competitive candidate devices in the future display and lighting technology fields.

[0003] OLED devices have undergone several significant developments and improvements, including single-layer, double-layer, triple-layer, multi-layer, stacked, and top-emitting devices. The basic structure of an OLED device includes an anode, a cathode, and an organic layer. The organic layer further comprises a hole injection layer, a hole transport layer, an electron blocking layer, and a light-emitting layer. Different functional layers can better fulfill their respective roles, either independently or in combination, to achieve more efficient light emission. Based on the light emission direction, OLEDs can be divided into top-emitting and bottom-emitting devices. The core characteristic of a top-emitting device is its vertical upward orientation. It involves depositing a capping layer outside the metal electrodes. This structure optimizes the electrode design and light extraction path, theoretically achieving 100% luminous efficiency. It overcomes many limitations of bottom-emitting devices and has irreplaceable advantages in large-size displays, flexible displays, and high-brightness applications. The light-emitting principle of OLEDs is that, under a certain voltage, hole carriers travel from the anode, overcoming the potential barriers between layers to reach the light-emitting layer; electron carriers travel from the cathode, overcoming the potential barriers between layers to reach the light-emitting layer. Hole carriers and electron carriers recombine in the light-emitting layer to form excitons, which then transition to emit light, thus enabling OLED devices to emit light.

[0004] The light-emitting layer is the core component of the device. To improve efficiency, host-guest doping is generally employed. An external voltage is applied to inject electrons and holes into the doped light-emitting layer. These electrons and holes recombine on the host material to form excitons, and then energy is transferred from the host material to the guest material via energy transfer. Therefore, a high-performance host material plays a crucial role in determining device performance. This requires the host material to possess good thermal stability, as well as excellent hole and charge transport capabilities. Current host materials face challenges in balancing luminous efficiency and stability, and relatively poor carrier transport performance, making it difficult to achieve an effective balance between electron and hole transport. This affects the device's luminous efficiency, performance stability, and material lifetime. The capping layer is used for coupling light emission in top-emitting devices, effectively improving the light emission efficiency of top-emitting OLED devices. Located on the outer side of the device, it does not affect the electrical performance, so only its optical performance needs to be considered. Generally, it needs to have high transparency, high refractive index, and good chemical stability, without chemically reacting with adjacent layers.

[0005] To improve the luminescence performance of devices, we have been working on developing high-performance luminescent layer and capping layer materials, which will enable devices to have better stability, higher luminescence efficiency, and longer lifespan. Summary of the Invention

[0006] To address the aforementioned problems, the present invention aims to provide a carbazole compound and its organic electroluminescent device, which can improve the luminous efficiency of the organic electroluminescent device and extend its service life.

[0007] This invention provides a carbazole compound having the structure represented by Formula I:

[0008] Group 1:

[0009] Wherein, X1 and X2 are independently selected from single bonds, O, S, and C(R). x R y Any one of X1 and X2; and one of X1 and X2 is selected from a single bond; The rings A, B, and C are independently selected from any one of the substituted or unsubstituted structures in group 1; The z is selected from C(R) t ); The R t R x R ySelected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, 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 C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl, or R x R y The links between them form substituted or unsubstituted rings; The Ar1 is selected from the group shown in Formula II;

[0010] The x is selected from either CH or N; X3 and X4 are independently selected from O, S, and C(R). i R j Any one of the following; and at least one of X3 and X4 is selected from any one of O and S; The R a R i R j Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C14 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; wherein R a R i R j The substituents in "substituted or unsubstituted" are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, silyl, C1-C25 alkyl, C3-C25 cycloalkyl, C1-C25 heterocyclic alkyl, C6-C30 aryl, C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, and C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups. a0 is selected from 0, 1, 2, 3, or 3; a1 is selected from 0, 1, 2, 3, or 4; when there are two or more R... a At that time, two or more R a The same or different between each other, or two adjacent R a They connect with each other to form substituted or unsubstituted aromatic rings; The L1 is selected from a single bond or any one of the following groups, or a combination of two or more of the following groups:

[0011] The v and v' are independently selected from either CH or N; and at most one of the v' is selected from N. The ring D is selected from substituted or unsubstituted C3~C10 alicyclic rings; X5 and X6 are independently selected from O, S, and N(R). s Any one of the following; X7 is selected from O, S, C(R) p R q ), N(R s Any one of the following; The R b R b '、R p R q Independently selected from any one of hydrogen, deuterium, tritium, fluorine, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R p R q The connections between them form substituted or unsubstituted rings; wherein the R b The substituents in "substituted or unsubstituted" are selected from any one of hydrogen, deuterium, tritium, fluorinyl, cyano, nitro, silyl, C1-C25 alkyl, C3-C25 cycloalkyl, C1-C25 heterocycloalkyl, C6-C30 aryl, and C2-C10 heteroaryl. The R s It is independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; p is selected from 1, 2, 3, or 4; b1 is selected from 0, 1, 2, 3, or 4; b2 is selected from 0, 1, 2, 3, 4, 5, or 6; b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; b4 is selected from 0, 1, or 2; when there are two or more R... b At that time, two or more R b The same or different between each other, or two adjacent R b They connect with each other to form substituted or unsubstituted rings; The b'1 is selected from 0, 1, or 2; when there are two or more R... b At that time, two or more R b 'They may be the same as or different from each other; The condition is that it does not contain the following compounds: , , .

[0012] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer located between the anode and the cathode or on the side of the cathode opposite to the anode, the organic layer comprising at least one of the carbazole compounds described in the present invention.

[0013] Beneficial effects

[0014] This invention provides a carbazole compound that, when used as a light-emitting layer in a device, exhibits excellent carrier transport performance and stability, effectively improving the device's luminous efficiency and extending its lifespan. When used as a capping layer in a device, this compound possesses a good refractive index and good chemical stability, further enhancing the device's luminous efficiency and extending its lifespan. The compound provided by this invention has a simple preparation method, readily available raw materials, and meets industrialization requirements, demonstrating promising prospects for industrialization. Detailed Implementation

[0015] The technical solutions of the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art fall within the scope defined by the present invention.

[0016] In this specification, " "This refers to the portion that is connected to another substituent." "It can be attached to any optional position of the attached group / fragment."

[0017] 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 ring. For example, Can represent or ; Can represent , , And so on.

[0018] In this specification, when the position of a substituent or linking site on the ring is not fixed, it means that it can be linked to any of the optional sites on the ring.

[0019] For example, Can represent , , ; Can represent , , ; Can represent , , , , , , , , , .

[0020] And so on.

[0021] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, and iodine.

[0022] The arylene group described in this invention refers to a divalent group formed by removing one hydrogen atom from each of the two aromatic carbon atoms of an aromatic hydrocarbon molecule. It can be a divalent monocyclic aryl group or a divalent fused-ring aryl group, preferably having 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Examples of arylene groups include phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, trimethyleneene, fluorene, pyrene, perylene, etc., but are not limited thereto.

[0023] The heteroaryl group described in this invention refers to a group formed by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, or phosphorus. The divalent heteroaryl group can be a divalent monocyclic heteroaryl or a divalent fused-ring heteroaryl, preferably having 2 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 15 carbon atoms. For example, it can be selected from pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, bipyridinyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, quinolineyl, isoquinolineyl, furanyl, thiopheneyl, carbazolyl, benzofuranyl, benzothiopheneyl, benzocarbazolyl, dibenzofuranyl, dibenzothiopheneyl, dibenzocarbazolyl, benzodibenzofuranyl, benzodibenzothiopheneyl, etc., but is not limited thereto.

[0024] The aryl group described in this invention refers to a group formed by removing a hydrogen atom from one of the aromatic carbon atoms of an aromatic hydrocarbon molecule. It can be a monocyclic aryl or a fused-ring aryl group, preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, pyrene, alkyl, etc., but are not limited thereto.

[0025] The heteroaryl group described in this invention refers to a group formed by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, germanium, or phosphorus. The heteroaryl group can be a monocyclic heteroaryl or a fused-ring heteroaryl, preferably having 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, particularly preferably 2 to 15 carbon atoms, and most preferably 2 to 12 carbon atoms. For example, it can be selected from pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, carbazoleyl, benzocarbazoleyl, furanyl, benzofuranyl, thiophenyl, benzothiophenyl, indolyl, dibenzofuranyl, benzodibenzofuranyl, naphthodibenzofuranyl, dibenzothiophenyl, benzodibenzothiophenyl, naphthodibenzothiophenyl, oxazolyl, benzooxazolyl, thiazolyl, benzothiazolyl, imidazoleyl, benzoimidazolyl, etc., but is not limited to these.

[0026] The alkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an alkane molecule. It may include straight-chain alkyl or branched-chain alkyl groups, preferably having 1 to 25 carbon atoms, more preferably having 1 to 12 carbon atoms, more preferably having 1 to 8 carbon atoms, and particularly preferably having 1 to 6 carbon atoms. For example, it may be selected from methyl, ethyl, propyl, butyl, pentyl, etc., but is not limited thereto.

[0027] The cycloalkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 25 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 5 to 10 carbon atoms, and most preferably 5 to 7 carbon atoms. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, etc., but are not limited thereto.

[0028] The heterocyclic alkyl group described in this invention refers to a group formed by removing one hydrogen atom from a heterocyclic molecule in which the atoms constituting the ring contain at least one heteroatom in addition to carbon atoms. The heteroatom includes, but is not limited to, oxygen, sulfur, nitrogen, or phosphorus, and preferably has 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 6 carbon atoms. Examples include piperidinyl, piperazineyl, morpholinyl, thiomorpholinyl, ethylene oxide, cyclothioethylene, tetrahydropyrrolyl, etc., but are not limited thereto.

[0029] The fused alicyclic and aromatic ring groups described in this invention refer to the collective term for the monovalent groups obtained after removing one hydrogen atom from the fused alicyclic and aromatic rings. Preferably, they have 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. The fused alicyclic and aromatic ring groups may include, but are not limited to, benzocyclopropane, benzocyclobutane, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptane, benzocycloheptenyl, etc.

[0030] The fused cyclic group of heterocyclic alkanes and aromatic rings described in this invention refers to the collective term for the monovalent group obtained after removing one hydrogen atom from the fused heterocyclic alkanes and aromatic rings. Preferably, it has 6 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. The fused cyclic group of heterocyclic alkanes and aromatic rings may include, but is not limited to, benzo[a]tetrahydropyrrole, naph[a]tetrahydropyrrole, phenanthrene[a]tetrahydropyrrole, benzo[a]hexacyclic butyl, benzo[a]hexacyclic heptyl, benzo[a]piperidinyl, naph[a]piperidinyl, phenanthrene[a]piperidinyl, etc.

[0031] The fused cyclic group of alicyclic and heteroaromatic rings described in this invention refers to the general term for the monovalent group obtained after removing one hydrogen atom from the fused alicyclic and heteroaromatic rings. Preferably, it has 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms. The fused cyclic group of alicyclic and heteroaromatic rings may include dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenocyclopropyl, dibenzothiophenocyclobutyl, dibenzothiophenocyclopentyl, dibenzothiophenocyclohexyl, etc. Benzothiophene-cycloheptyl, carbazo-cyclopropyl, carbazo-cyclobutyl, carbazo-cyclopentyl, carbazo-cyclohexyl, carbazo-cycloheptyl, carbazo-cyclopentenyl, pyrido-cyclopropyl, pyrido-cyclobutyl, pyrido-cyclopentyl, pyrido-cyclohexyl, pyrido-cycloheptyl, pyrido-cyclopentenyl, pyrimidino-cyclopropyl, pyrimidino-cyclobutyl, pyrimidino-cyclopentyl, pyrimidino-cyclohexyl, pyrimidino-cycloheptyl, pyrimidino-cyclopentenyl, etc., but not limited to these.

[0032] In this invention, "substituted or unsubstituted" means that at least one hydrogen atom on a group is replaced by a substituent. When multiple hydrogen atoms are replaced by multiple substituents, the multiple substituents may be the same or different. The position of the hydrogen atoms replaced by the substituents can be arbitrary. The substituents may be independently selected from deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C6 alkylthio, substituted or unsubstituted C1-C12 alkylamine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, etc., but are not limited thereto, or adjacent substituents may be connected to form a ring. Preferred compounds include deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl groups, C1-C25 alkyl groups, C3-C25 cycloalkyl groups, C6-C30 aryl groups, C2-C30 heteroaryl groups, C3-C30 alicyclic and C6-C30 fused cycloyl groups, and C1-C12 alkoxy groups. Specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, silyl, trimethylsilyl, triethylsilyl, tripropylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, fluoranyl, indene, perylene, and dihydrogen. Indene, dihydronaphthyl, tetrahydronaphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirodifluorenyl, carbazole, 9-phenylcarbazole, carbazole-indole, pyrrole, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, pyridyl, pyrimidinyl, pyrazinyl, pyrazinyl Triazinyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phenthiazolyl, acridineyl, benzocyclobutyl, benzocyclobutenyl, benzocyclopentyl, benzocyclopentenyl, benzocyclohexyl, benzocyclohexenyl, etc., but not limited to these. Each of the above substituents may be substituted or unsubstituted, or when there are multiple substituents, the multiple substituents may be the same or different from each other; or adjacent substituents may be linked to form a ring.

[0033] The "substituted or unsubstituted silyl group" mentioned in this invention refers to -Si(R n )3 groups, wherein each R nThe same or different from any one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, 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 C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl. The substituted or unsubstituted silyl group may include, but is not limited to, trimethylsilyl, triethylsilyl, ethyl dimethylsilyl, triisopropylsilyl, propyl dimethylsilyl, tri-tert-butylsilyl, tert-butyl dimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyl dimethylsilyl, etc.

[0034] 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:

[0035] In this invention, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of the two. The ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0036] In this invention, "at least one" includes one, two, three, or more. "Two or more" may include two, three, four, or more, where permissible.

[0037] This invention provides a carbazole compound having the structure represented by Formula I:

[0038] Group 1:

[0039] Wherein, X1 and X2 are independently selected from single bonds, O, S, and C(R). x R y Any one of X1 and X2; and one of X1 and X2 is selected from a single bond; The rings A, B, and C are independently selected from any one of the substituted or unsubstituted structures in group 1; The z is selected from C(R)t ); The R t R x R y Selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, 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 C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl, or R x R y The links between them form substituted or unsubstituted rings; The Ar1 is selected from the group shown in Formula II;

[0040] The x is selected from either CH or N; X3 and X4 are independently selected from O, S, and C(R). i R j Any one of the following; and at least one of X3 and X4 is selected from any one of O and S; The R a R i R j Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C14 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; wherein R a R i R jThe substituents in "substituted or unsubstituted" are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, silyl, C1-C25 alkyl, C3-C25 cycloalkyl, C1-C25 heterocyclic alkyl, C6-C30 aryl, C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, and C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups. a0 is selected from 0, 1, 2, 3, or 3; a1 is selected from 0, 1, 2, 3, or 4; when there are two or more R... a At that time, two or more R a The same or different between each other, or two adjacent R a They connect with each other to form substituted or unsubstituted aromatic rings; The L1 is selected from a single bond or any one of the following groups, or a combination of two or more of the following groups:

[0041] The v and v' are independently selected from either CH or N; and at most one of the v' is selected from N. The ring D is selected from substituted or unsubstituted C3~C10 alicyclic rings; X5 and X6 are independently selected from O, S, and N(R). s Any one of the following; X7 is selected from O, S, C(R) p R q ), N(R s Any one of the following; The R b R b '、R p R q Independently selected from any one of hydrogen, deuterium, tritium, fluorine, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R p R q The connections between them form substituted or unsubstituted rings; wherein the R b The substituents in "substituted or unsubstituted" are selected from any one of hydrogen, deuterium, tritium, fluorinyl, cyano, nitro, silyl, C1-C25 alkyl, C3-C25 cycloalkyl, C1-C25 heterocycloalkyl, C6-C30 aryl, and C2-C10 heteroaryl. The R sIt is independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; p is selected from 1, 2, 3, or 4; b1 is selected from 0, 1, 2, 3, or 4; b2 is selected from 0, 1, 2, 3, 4, 5, or 6; b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; b4 is selected from 0, 1, or 2; when there are two or more R... b At that time, two or more R b The same or different between each other, or two adjacent R b They connect with each other to form substituted or unsubstituted rings; The b'1 is selected from 0, 1, or 2; when there are two or more R... b At that time, two or more R b 'They may be the same as or different from each other; The condition is that it does not contain the following compounds: , , .

[0042] Preferably, the carbazole compound is selected from any one of the following structures:

[0043] Ar1, L1, ring A, ring B, ring C, and R x R y The definition is the same as that in Equation I.

[0044] Preferred, R x R yIndependently selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperin Any one of the following: pyridyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, perylene, fluoranthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, or R x R y The rings can be substituted or unsubstituted, and can be formed by connecting the following: any one of the following: cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclopentene ring, cyclohexane ring, cyclohexene ring, cycloheptane ring, cycloheptene ring, and fluorene ring.

[0045] Preferably, the group represented by Formula II is selected from any one of the following groups:

[0046] The x is selected from either CH or N; The R a R i R jSelected from hydrogen, deuterium, tritium, halogen, cyano, nitro, and the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl. Any one of tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, diphenylphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, perylene, fluoranthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl; wherein R a R i R j The substituents in "substituted or unsubstituted" are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, di... The following is a list of phenylsilyl, phenylsilyl, vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, and fluoranthracene; a0 is selected from 0, 1, 2, 3, or 3; a1 is selected from 0, 1, 2, 3, or 4; a2 is selected from 0, 1, 2, 3, 4, 5, or 6; a3 is selected from 0, 1, 2, 3, 4, or 5; when there are two or more R... a At that time, two or more R a The same or different between each other, or two adjacent R a They connect with each other to form substituted or unsubstituted rings.

[0047] More preferably, the group represented by Formula II is selected from any one of the following groups: .

[0048] Preferably, L1 is independently selected from a single bond or any one of the following groups, or a combination of two or more of the following groups:

[0049] The R b R b '、R p R qThe group is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, the group shown in Formula II, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl Alkyl, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiophene, pyrroleyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzimidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthilinyl, indoleyl; The R s The following groups are independently selected from hydrogen, deuterium, tritium, and substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl The following are all of the following: vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; b1 is selected from 0, 1, 2, 3, or 4; b2 is selected from 0, 1, 2, 3, 4, 5, or 6; b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; b4 is selected from 0, 1, or 2; b5 is selected from 0, 1, 2, or 3; b6 is selected from 0 or 1; b7 is selected from 0, 1, 2, 3, 4, or 5; b8 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when there are two or more R... b At that time, two or more R bThe same or different between each other, or two adjacent R b They connect with each other to form substituted or unsubstituted rings; The b'1 is selected from 0, 1, or 2; the b'2 is selected from 0, 1, 2, 3, or 4; the b'3 is selected from 0, 1, 2, 3, 4, 5, or 6; the b'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the b'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the b'6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; when there are two or more R b At that time, two or more R b 'They are the same as or different from each other.'

[0050] Preferably, the substituents in "substituted or unsubstituted" in L1 are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, and piperidinyl.

[0051] Preferably, the R bThe group may contain at most 3, 2, or 1 groups selected from the groups shown in Formula II, substituted or unsubstituted, of the following groups: benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiophene, pyrroleyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, imidazole, benzoimidazolyl, quinoline. The following groups are included: methyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, indolyl; the rest are selected from: hydrogen, deuterium, tritium, halogen, cyano, nitro, and substituted or unsubstituted groups such as: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl.

[0052] More preferably, L1 is independently selected from a single bond or any one of the following groups, or a combination of two or more of the following groups: .

[0053] Most preferably, formula I is selected from any of the following structures: .

[0054] The above lists some specific structural forms of carbazole compounds represented by chemical formula I according to the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in chemical formula I, with substituents as defined above, should be included.

[0055] The present invention provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer located between the anode and the cathode or on the side of the cathode opposite to the anode, wherein the organic layer comprises at least one of the carbazole compounds described in the present invention.

[0056] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes at least one of a hole transport region, a light-emitting layer, and an electron transport layer.

[0057] Preferably, the hole transport region includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer.

[0058] 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.

[0059] Preferably, the hole transport layer includes a first hole transport layer, a second hole transport layer, and a third hole transport layer, wherein the first hole transport layer is located between the anode and the light-emitting layer, the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and the third hole transport layer is located between the second hole transport layer and the light-emitting layer.

[0060] Preferably, the organic layer is located between the anode and the cathode, and the organic layer comprises at least one of the light-emitting layers, wherein the at least one of the light-emitting layers comprises at least one of the carbazole compounds described in this invention.

[0061] Preferably, the light-emitting layer comprises a host material and a dopant material.

[0062] More preferably, the light-emitting layer comprises a host material, which comprises at least one of the carbazole compounds described in this invention.

[0063] Preferably, the electron transport region comprises at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0064] Preferably, the organic layer is located on the side of the cathode opposite to the anode, and the organic layer includes a capping layer containing at least one of the carbazole compounds described in this invention.

[0065] The anode of this invention preferably uses a material with a high work function. It may include metals, alloys, conductive compounds, and mixtures thereof, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), magnesium (Mg), silver (Ag), aluminum (Al), gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), aluminum-lithium (Al-Li), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode may have a single-layer structure or a multilayer structure comprising two or more layers; for example, the anode may have a single-layer structure of Al or a three-layer structure of ITO / Ag / ITO, but is not limited thereto.

[0066] The hole injection layer described in this invention is a layer containing a substance with high hole injection capability. It may include triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and its derivatives, phthalocyanine derivatives, axialene compounds, molybdenum oxide, titanium oxide, vanadium oxide, and other transition metal oxides, as well as other substances with high hole injection capability, such as 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzenephenanthrene (HATCN), copper phthalocyanine (CuPC), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly(3,4-ethylenedioxythiophene)- Poly(styrene sulfonic acid) (PEDOT / PSS), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (DPA3B), etc., but not limited to these.

[0067] The hole transport layer described in this invention is preferably made of a material with excellent hole transport performance. It may include carbazole derivatives, fluorene derivatives, biphenyl diamine derivatives, triarylamine derivatives, stilbene derivatives, etc., such as N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BAFLP), 4, 4'-Bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (DFLDPBi), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), 4,4'-bis[N-(spiro-9,9'-difluorene-2-yl)-N-phenylamino]biphenyl (BSPB), etc., but not limited to these.

[0068] The electron blocking layer described in this invention is preferably made of a material with good hole transport capability and electron blocking capability. It may include aromatic amine derivatives, carbazole derivatives, etc. Specific examples may include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4',4”-tris(N-carbazole)triphenylamine (TCTA), 1,3-bis(carbazole-9-yl)benzene (mCP), etc., but are not limited thereto.

[0069] The light-emitting layer of this invention may include a dopant material and a host material, and the light-emitting layer material may also include multiple host materials and multiple dopant materials. The type of dopant material can be a fluorescent material, a phosphorescent material, or a TADF material. Fluorescent dopant materials may include: fused polycyclic aromatic derivatives, styrene-based amine derivatives, fused-ring amine derivatives, boron-containing compounds, pyrrole derivatives, indole derivatives, carbazole derivatives, etc., such as 5,4'-diphenylcoumarin (C545T), 4,4'-bis(9-ethyl-3-carbazolevinyl)-1,1'-biphenyl (BCzVBi), 4,4'-bis[4-(di-p-tolylamino)styrene]biphenyl (DPAVBi), etc. Phosphorescent doping materials may include heavy metal complexes, phosphorescent rare-earth metal complexes, such as bis(4,6-difluorophenylpyridine-N,C2)pyridinecarboxylate iridium (FIrpic), tris(2-phenylpyridine)iridium (Ir(ppy)3), and bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)). In addition to the carbazole compounds provided in this invention, the host material may also include fused aromatic ring derivatives, heterocyclic compounds, etc. Fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene derivatives, fluoranthene derivatives, etc., and heterocyclic compounds including carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, etc., such as N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 4,4'-di(9-carbazole)biphenyl (CBP), 4,4',4''-tris(carbazole-9-yl)triphenylamine (TCTA), 9,10-di(2-naphthyl)anthracene (ADN), etc., but are not limited thereto. The carbazole compounds of the present invention are preferred.

[0070] The hole-blocking layer described in this invention may include aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthrene derivatives, triazine derivatives, quinoline derivatives, diazanphenanthrene derivatives, azabenzene derivatives, etc., such as bicyclo[1.1.1]pentane (BCP), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 4,7-diphenyl-1,10-phenanthroline (Bphen), 1,3-bis[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (OXD-7), lithium 8-hydroxyquinoline (Liq), etc., but is not limited thereto.

[0071] The electron transport layer described in this invention is preferably made of a material with good electron mobility. It can include metal complexes, oxazolium derivatives, oxazole derivatives, diazole derivatives, aziridine derivatives, phenanthroline derivatives, diazanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, quinoline derivatives, benzimidazole derivatives, etc., such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), tris(8-hydroxyquinoline)aluminum(III) (Alq3), 8-hydroxyquinoline-lithium (Liq), di(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 4,7-diphenyl-1,10-phenanthroline (Bphen), etc., but is not limited to these.

[0072] The electron injection layer described in this invention may include alkali metals, alkaline earth metals or their compounds, other substances with high electron injection capacity, such as lithium oxide (Li2O), lithium fluoride (LiF), 8-hydroxyquinoline-lithium (Liq), cesium carbonate (Cs2CO3), potassium silicate (K2SiO3), calcium fluoride (CaF2), calcium oxide (CaO), magnesium fluoride (MgF2), magnesium oxide (MgO), etc., but is not limited thereto.

[0073] The cathode described in this invention is preferably a low work function material. It may include metals, metal alloys, or multilayer structures, such as silver (Ag), lithium (Li), magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), neodymium (Nd), iridium (Ir), chromium (Cr), lithium (Li), calcium (Ca), molybdenum (Mo), titanium (Ti), aluminum-lithium (Al-Li), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag), but is not limited thereto.

[0074] The capping material described in this invention can be a single-layer structure composed of a single substance, or a single-layer or multi-layer structure composed of different substances. Preferably, it is an organic or inorganic material with an appropriate refractive index. Besides the carbazole compound provided by this invention, it may also include aromatic compounds, heteroaromatic compounds, aromatic amine compounds, biscarbazole derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, triazole derivatives, benzofuran derivatives, diamine derivatives, etc., such as aluminum 8-hydroxyquinoline (Alq3), lithium fluoride (LiF), cesium fluoride (CsF), magnesium fluoride (MgF2), calcium fluoride (CaF2), cesium chloride (CsCl), cuprous iodide (CuI), vanadium pentoxide (V2O5), molybdenum trioxide (MoO3), titanium dioxide (TiO2), zinc oxide (ZnO), silicon dioxide (SiO2), silicon nitride (SiN), zinc sulfide (ZnS), etc., but is not limited thereto. The carbazole compound of this invention is preferred.

[0075] The following is one method for preparing the compound represented by chemical formula I of this invention, but the preparation method of this invention is not limited thereto. The core structure of the compound of chemical formula I can be prepared by the reaction route shown below. Substituents can be bonded by methods known in the art, and the type and position or number of substituents can be changed according to techniques known in the art.

[0076] [Synthesis Route]

[0077] Xa and Xb are selected from any one of Cl, Br, and I; the restrictions on ring A, ring B, ring C, Ar1, L1, X1, and X2 are the same as those described above.

[0078] Description of raw materials, reagents, and characterization equipment: The present invention does not impose any particular restrictions on the source of raw materials and reagents used in the following embodiments, which can be commercially available products or prepared using preparation methods well known to those skilled in the art.

[0079] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent. Elemental analysis was performed using a VarioELcube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0080] Synthesis Example 1: Preparation of Compound 28

[0081] Preparation of intermediate A-28

[0082] Under nitrogen protection, a-28 (13.68 g, 60.00 mmol), b-28 (16.05 g, 60.00 mmol), and K₂CO₃ (16.59 g, 120.00 mmol) were dissolved in 350 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl₂ (0.88 g, 1.20 mmol) was added with stirring, and the mixture was heated under reflux for 5 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol in an 8:1 ratio to give intermediate A-28 (18.02 g, 81% yield); HPLC purity ≥ 99.87%. Mass spectrometry m / z: 370.0775 (theoretical value: 370.0761).

[0083] Preparation of compound 28

[0084] Under nitrogen protection, C-28 (7.72 g, 30.00 mmol), A-28 (11.12 g, 30.00 mmol), and sodium tert-butoxide (4.32 g, 45.00 mmol) dissolved in 150 mL of toluene were added to a reaction flask. Pd₂(dba)₃ (0.27 g, 0.30 mmol) and X-Phos (0.29 g, 0.60 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 7 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound 28 (13.13 g, 74%). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 591.1845 (theoretical value: 591.1834). Theoretical elemental content (%) C 42 H 25 NO3: C, 85.26; H, 4.26; N, 2.37. Measured elemental content (%): C, 85.23; H, 4.27; N, 2.35.

[0085] Synthesis Example 2: Preparation of Compound 63

[0086] According to the preparation method in Example 1, a-28 was replaced with an equimolar amount of a-63, b-28 with an equimolar amount of b-63, and c-28 with an equimolar amount of c-63, yielding compound 63 (13.85 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 615.1822 (theoretical value: 615.1834). Theoretical elemental content (%) C 44 H 25NO3: C, 85.84; H, 4.09; N, 2.28. Measured elemental content (%): C, 85.81; H, 4.07; N, 2.31.

[0087] Synthesis Example 3: Preparation of Compound 143

[0088] According to the preparation method in Example 1, a-28 was replaced with an equimolar amount of a-143, b-28 with an equimolar amount of b-143, and c-28 with an equimolar amount of c-143, yielding compound 143 (13.29 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 623.1361 (theoretical value: 623.1378). Theoretical elemental content (%) C 42 H 25 NOS2: C, 80.87; H, 4.04; N, 2.25. Measured elemental content (%): C, 80.84; H, 4.01; N, 2.28.

[0089] Synthesis Example 4: Preparation of Compound 184

[0090] According to the preparation method in Example 1, a-28 was replaced with an equimolar amount of a-184, b-28 with an equimolar amount of b-184, and c-28 with an equimolar amount of c-143, yielding compound 184 (12.91 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 597.1234 (theoretical value: 597.1221). Theoretical elemental content (%) C 40 H 23 NOS2: C, 80.37; H, 3.88; N, 2.34. Measured elemental content (%): C, 80.40; H, 3.87; N, 2.35.

[0091] Synthesis Example 5: Preparation of Compound 331

[0092] According to the preparation method in Example 1, c-28 was replaced with an equimolar amount of c-331, and A-28 was replaced with an equimolar amount of A-331 to obtain compound 331 (10.02 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 439.1219 (theoretical value: 439.1208). Theoretical elemental content (%) C 30 H 17 NO3: C, 81.99; H, 3.90; N, 3.19. Measured elemental content (%): C, 81.97; H, 3.85; N, 3.21.

[0093] Synthesis Example 6: Preparation of Compound 384

[0094] According to the preparation method in Synthesis Example 1, a-28 was replaced with an equimolar amount of a-63, b-28 with an equimolar amount of b-384, and c-28 with an equimolar amount of c-384, yielding compound 384 (12.25 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 591.1844 (theoretical value: 591.1834). Theoretical elemental content (%) C 42 H 25 NO3: C, 85.26; H, 4.26; N, 2.37. Measured elemental content (%): C, 85.30; H, 4.27; N, 2.39.

[0095] Synthesis Example 7: Preparation of Compound 417

[0096] According to the preparation method in Example 1, a-28 was replaced with an equimolar amount of a-184, b-28 with an equimolar amount of b-417, and c-28 with an equimolar amount of c-417, yielding compound 417 (11.83 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 547.1077 (theoretical value: 547.1065). Theoretical elemental content (%) C 36 H 21 NOS2: C, 78.95; H, 3.86; N, 2.56. Measured elemental content (%): C, 78.92; H, 3.88; N, 2.59.

[0097] Synthesis Example 8: Preparation of Compound 531

[0098] Preparation of intermediate A-531

[0099] Under nitrogen protection, a-143 (31.22 g, 120.00 mmol), b-531 (16.22 g, 60.00 mmol), and K2CO3 (24.88 g, 180.00 mmol) were dissolved in 500 mL toluene / ethanol / water (2:1:1). Pd(dppf)Cl2 (1.32 g, 1.80 mmol) was added with stirring, and the mixture was heated under reflux for 6 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol in an 8:1 ratio to give intermediate A-531 (25.33 g, 79% yield); HPLC purity ≥ 99.82%. Mass spectrometry m / z: 539.9919 (theoretical value: 539.9902).

[0100] Preparation of compound 531

[0101] Under nitrogen protection, C-384 (7.72 g, 30.00 mmol), A-531 (16.23 g, 30.00 mmol), and sodium tert-butoxide (4.32 g, 45.00 mmol) dissolved in 150 mL of toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (0.27 g, 0.30 mmol) and X-Phos (0.29 g, 0.60 mmol) were then added. The mixture of the above reactants was heated under reflux for 7 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound 531 (15.32 g, 67%). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 761.0986 (theoretical value: 761.0975). Theoretical elemental content (%) C 48 H 27 NOS4: C, 75.66; H, 3.57; N, 1.84. Measured elemental content (%): C, 75.71; H, 3.58; N, 1.78.

[0102] Synthesis Example 9: Preparation of Compound 546

[0103] According to the preparation method in Synthesis Example 1, a-28 was replaced with an equimolar amount of a-546, b-28 with an equimolar amount of b-546, and c-28 with an equimolar amount of c-331, yielding compound 546 (11.40 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 542.1981 (theoretical value: 542.1994). Theoretical elemental content (%) C 38 H 26N2O2: C, 84.11; H, 4.83; N, 5.16. Measured elemental content (%): C, 84.09; H, 4.88; N, 5.17.

[0104] Synthesis Example 10: Preparation of Compound 558

[0105] According to the preparation method in Example 1, c-28 was replaced with an equimolar amount of c-143, and A-28 was replaced with an equimolar amount of A-558, yielding compound 558 (11.88 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 573.2312 (theoretical value: 573.2304). Theoretical elemental content (%) C 40 H 31 NO3: C, 83.75; H, 5.45; N, 2.44. Measured elemental content (%): C, 83.81; H, 5.47; N, 2.41.

[0106] Synthesis Example 11: Preparation of Compound 599

[0107] According to the preparation method in Synthesis Example 1, a-28 was replaced with an equimolar amount of a-143, and b-28 was replaced with an equimolar amount of b-599, yielding compound 599 (12.64 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 628.1680 (theoretical value: 628.1691). Theoretical elemental content (%) C 42 H 20 D5NOS2: C, 80.22; H, 4.81; N, 2.23. Measured elemental content (%): C, 80.21; H, 4.83; N, 2.19.

[0108] Synthesis Example 12: Preparation of Compound 607

[0109] According to the preparation method in Synthesis Example 1, a-28 was replaced with an equimolar amount of a-607, b-28 with an equimolar amount of b-417, and c-28 with an equimolar amount of c-63, yielding compound 607 (11.86 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 556.1254 (theoretical value: 556.1245). Theoretical elemental content (%) C 37 H 20 N2O2S: C, 79.84; H, 3.62; N, 5.03. Measured elemental content (%): C, 79.81; H, 3.65; N, 5.07.

[0110] Synthetic Example 13: Preparation of Compound 634

[0111] According to the preparation method in Synthesis Example 1, a-28 was replaced with an equimolar amount of a-634, b-28 with an equimolar amount of b-634, and c-28 with an equimolar amount of c-331, yielding compound 634 (13.34 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 663.2215 (theoretical value: 663.2230). Theoretical elemental content (%) C 45 H 33 NO3Si: C, 81.42; H, 5.01; N, 2.11. Measured elemental content (%): C, 81.40; H, 5.05; N, 2.13.

[0112] Synthesis Example 14: Preparation of Compound 643

[0113] According to the preparation method in Synthesis Example 1, a-28 was replaced with an equimolar amount of a-143, b-28 with an equimolar amount of b-643, and c-28 with an equimolar amount of c-643, yielding compound 643 (12.56 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 615.0947 (theoretical value: 615.0938). Theoretical elemental content (%) C 37 H 20 F3NOS2: C, 72.18; H, 3.27; N, 2.28. Measured elemental content (%): C, 72.15; H, 3.30; N, 2.24.

[0114] Synthesis Example 15: Preparation of Compound 656

[0115] According to the preparation method in Example 1, a-28 was replaced with an equimolar amount of a-143, b-28 with an equimolar amount of b-643, and c-28 with an equimolar amount of c-656, yielding compound 656 (12.75 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 624.1319 (theoretical value: 624.1330). Theoretical elemental content (%) C 41 H 24 N₂OS₂: C, 78.82; H, 3.87; N, 4.48. Measured elemental content (%): C, 78.80; H, 3.88; N, 4.44.

[0116] Synthesis Example 16: Preparation of Compound 669

[0117] According to the preparation method in Synthesis Example 1, b-28 was replaced with an equimolar amount of b-669, and c-28 was replaced with an equimolar amount of c-669, yielding compound 669 (11.96 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 531.1278 (theoretical value: 531.1293). Theoretical elemental content (%) C 36 H 21 NO2S: C, 81.33; H, 3.98; N, 2.63. Measured elemental content (%): C, 81.31; H, 3.95; N, 2.67.

[0118] Synthesis Example 17: Preparation of Compound 723

[0119] According to the preparation method in Synthesis Example 1, b-28 was replaced with an equimolar amount of b-723, and c-28 was replaced with an equimolar amount of c-723, yielding compound 723 (12.52 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 571.1615 (theoretical value: 571.1606). Theoretical elemental content (%) C 39 H 25 NO2S: C, 81.94; H, 4.41; N, 2.45. Measured elemental content (%): C, 81.91; H, 4.47; N, 2.46.

[0120] Synthesis Example 18: Preparation of Compound 753

[0121] According to the preparation method in Example 1, a-28 was replaced with a-753, b-28 was replaced with an equimolar amount of b-417, and c-28 was replaced with an equimolar amount of c-669, yielding compound 753 (13.09 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 581.1461 (theoretical value: 581.1449). Theoretical elemental content (%) C 40 H 23 NO2S: C, 82.59; H, 3.99; N, 2.41. Measured elemental content (%): C, 82.61; H, 3.95; N, 2.40.

[0122] Synthesis Example 19: Preparation of Compound 820

[0123] According to the preparation method in Example 1, a-28 was replaced with a-143, b-28 was replaced with an equimolar amount of b-820, and c-28 was replaced with an equimolar amount of c-820, yielding compound 820 (14.07 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 679.1472 (theoretical value: 679.1462). Theoretical elemental content (%) C 45 H 29 NS3: C, 79.49; H, 4.30; N, 2.06. Measured elemental content (%): C, 79.51; H, 4.31; N, 2.08.

[0124] Synthesis Example 20: Preparation of Compound 875

[0125] According to the preparation method in Example 1, c-28 was replaced with an equimolar amount of c-875, and A-28 was replaced with an equimolar amount of A-875, yielding compound 875 (11.67 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 547.1412 (theoretical value: 547.1428). Theoretical elemental content (%) C 37 H 25 NS2: C, 81.14; H, 4.60; N, 2.56. Measured elemental content (%): C, 81.17; H, 4.63; N, 2.53.

[0126] Synthesis Example 21: Preparation of Compound 919

[0127] According to the preparation method in Synthesis Example 1, b-28 was replaced with an equimolar amount of b-919, and c-28 was replaced with an equimolar amount of c-919 to obtain compound 919 (12.89 g). HPLC analysis showed that the solid purity was ≥99.94%. Mass spectrometry m / z: 631.1619 (theoretical value: 631.1606). Theoretical elemental content (%) C 44 H 25 NO2S: C, 83.65; H, 3.99; N, 2.22. Measured elemental content (%): C, 83.66; H, 3.94; N, 2.21.

[0128] Synthesis Example 22: Preparation of Compound 925

[0129] According to the preparation method in Example 1, a-28 was replaced with an equimolar amount of a-925, b-28 with an equimolar amount of b-643, and c-28 with an equimolar amount of c-925, yielding compound 925 (11.50 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 532.1254 (theoretical value: 532.1245). Theoretical elemental content (%) C 35 H 20 N2O2S: C, 78.93; H, 3.79; N, 5.26. Measured elemental content (%): C, 78.97; H, 3.82; N, 5.29.

[0130] Synthesis Example 23: Preparation of Compound 1017

[0131] According to the preparation method in Example 1, a-28 was replaced with an equimolar amount of a-184, b-28 with an equimolar amount of b-1017, and c-28 with an equimolar amount of c-1017, yielding compound 1017 (13.24 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 639.1158 (theoretical value: 639.1149). Theoretical elemental content (%) C 42 H 25 NS3: C, 78.84; H, 3.94; N, 2.19. Measured elemental content (%): C, 78.87; H, 3.97; N, 2.16.

[0132] Synthesis Example 24: Preparation of Compound 1037

[0133] According to the preparation method in Synthesis Example 1, a-28 was replaced with an equimolar amount of a-1037, b-28 with an equimolar amount of b-417, and c-28 with an equimolar amount of c-919, yielding compound 1037 (13.71 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 681.2113 (theoretical value: 681.2126). Theoretical elemental content (%) C 49 H 31 NOS: C, 86.31; H, 4.58; N, 2.05. Measured elemental content (%): C, 86.33; H, 4.57; N, 2.09.

[0134] Synthesis Example 25: Preparation of Compound 1049

[0135] According to the preparation method in Synthesis Example 1, b-28 was replaced with an equimolar amount of b-1049, and c-28 was replaced with an equimolar amount of c-669, yielding compound 1049 (11.57 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 535.1532 (theoretical value: 535.1544). Theoretical elemental content (%) C 36 H 17 D4NO2S: C, 80.72; H, 4.70; N, 2.61. Measured elemental content (%): C, 80.70; H, 4.71; N, 2.63.

[0136] Synthesis Example 26: Preparation of Compound 1056

[0137] According to the preparation method in Example 1, a-28 was replaced with an equimolar amount of a-63, b-28 with an equimolar amount of b-417, and c-28 with an equimolar amount of c-1056, yielding compound 1056 (11.86 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 541.1937 (theoretical value: 541.1921). Theoretical elemental content (%) C 36 H 11 D 10 NO2S: C, 79.82; H, 5.77; N, 2.59. Measured elemental content (%): C, 79.83; H, 5.74; N, 2.57.

[0138] Synthesis Example 27: Preparation of Compound 1067

[0139] According to the preparation method in Synthesis Example 1, a-28 was replaced with an equimolar amount of a-143, b-28 with an equimolar amount of b-1067, and c-28 with an equimolar amount of c-820, yielding compound 1067 (13.99 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 695.1761 (theoretical value: 695.1775). Theoretical elemental content (%) C 46 H 33 NS3: C, 79.39; H, 4.78; N, 2.01. Measured elemental content (%): C, 79.41; H, 4.75; N, 2.04.

[0140] Synthesis Example 28: Preparation of Compound 1098

[0141] According to the preparation method in Synthesis Example 1, a-28 was replaced with an equimolar amount of a-1098, b-28 with an equimolar amount of b-417, and c-28 with an equimolar amount of c-1017, yielding compound 1098 (12.58 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 607.1617 (theoretical value: 607.1606). Theoretical elemental content (%) C 42 H 25 NO2S: C, 83.01; H, 4.15; N, 2.30. Measured elemental content (%): C, 83.05; H, 4.20; N, 2.29.

[0142] Synthesis Example 29: Preparation of Compound 1181

[0143] According to the preparation method in Synthesis Example 1, a-28 was replaced with an equimolar amount of a-63, b-28 with an equimolar amount of b-1181, and c-28 with an equimolar amount of c-1181, yielding compound 1181 (14.38 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 694.2635 (theoretical value: 694.2620). Theoretical elemental content (%) C 50 H 34 N2O2: C, 86.43; H, 4.93; N, 4.03. Measured elemental content (%): C, 86.45; H, 4.96; N, 4.04.

[0144] Synthesis Example 30: Preparation of Compound 1229

[0145] According to the preparation method in Example 1, a-28 was replaced with an equimolar amount of a-143, b-28 with an equimolar amount of b-1229, and c-28 with an equimolar amount of c-1229, yielding compound 1229 (14.59 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 725.2223 (theoretical value: 725.2211). Theoretical elemental content (%) C 51 H 35 NS2: C, 84.38; H, 4.86; N, 1.93. Measured elemental content (%): C, 84.36; H, 4.88; N, 1.97.

[0146] Synthesis Example 31: Preparation of Compound 1395

[0147] According to the preparation method in Synthesis Example 1, a-28 was replaced with an equimolar amount of a-184, b-28 with an equimolar amount of b-1395, and c-28 with an equimolar amount of c-1395, yielding compound 1395 (13.87 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 679.1471 (theoretical value: 679.1462). Theoretical elemental content (%) C 45 H 29 NS3: C, 79.49; H, 4.30; N, 2.06. Measured elemental content (%): C, 79.52; H, 4.26; N, 2.08.

[0148] Synthesis Example 32: Preparation of Compound 1444

[0149] According to the preparation method in Synthesis Example 1, b-28 was replaced with an equimolar amount of b-417, and c-28 was replaced with an equimolar amount of c-1444, yielding compound 1444 (13.18 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 665.2367 (theoretical value: 665.2355). Theoretical elemental content (%) C 49 H 31 NO2: C, 88.40; H, 4.69; N, 2.10. Measured elemental content (%): C, 88.42; H, 4.65; N, 2.11.

[0150] Synthesis Example 33: Preparation of Compound 1457

[0151] According to the preparation method in Synthesis Example 1, a-28 was replaced with an equimolar amount of a-143, b-28 with an equimolar amount of b-1457, and c-28 with an equimolar amount of c-1457, yielding compound 1457 (14.57 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 735.1682 (theoretical value: 735.1691). Theoretical elemental content (%) C 51 H 29 NOS2: C, 83.24; H, 3.97; N, 1.90. Measured elemental content (%): C, 83.27; H, 3.95; N, 1.93.

[0152] Synthesis Example 34: Preparation of Compound 1478

[0153] According to the preparation method in Synthesis Example 1, a-28 was replaced with an equimolar amount of a-1478, b-28 was replaced with an equimolar amount of b-1478, and c-28 was replaced with an equimolar amount of c-1478, yielding compound 1478 (14.15 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 693.2657 (theoretical value: 693.2668). Theoretical elemental content (%) C 51 H 35 NO2: C, 88.28; H, 5.08; N, 2.02. Measured elemental content (%): C, 88.32; H, 5.11; N, 2.05.

[0154] Synthetic Example 35: Preparation of Compound 1515

[0155] According to the preparation method in Synthesis Example 1, a-28 was replaced with an equimolar amount of a-1515, b-28 was replaced with an equimolar amount of b-1515, and c-28 was replaced with an equimolar amount of c-1515, yielding compound 1515 (13.91 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 691.2330 (theoretical value: 691.2345). Theoretical elemental content (%) C 48 H 34 FNOS: C, 83.33; H, 4.95; N, 2.02. Measured elemental content (%): C, 83.36; H, 4.97; N, 2.01.

[0156] [Device Examples]

[0157] A combined IVL testing system was used to test the luminous efficiency of organic electroluminescent devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using the McScience M6000 OLED lifetime testing system.

[0158] [Example 1]

[0159] The glass substrate was cleaned using distilled water and ultrasonic cleaning. After distilled water washing, ultrasonic cleaning was performed using solvents such as isopropanol, acetone, and methanol, followed by drying. After drying, the substrate was transferred to a plasma cleaner, and then transferred to an evaporation deposition machine. Indium tin oxide (ITO) was coated onto the glass substrate to form an anode. HI-1:HT-1 (mass ratio 2:98) was deposited on the anode to form a hole injection layer with a thickness of 100 Å. HT-1 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 1200 Å. HT-2 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 100 Å. EB-1 was deposited on the second hole transport layer to form an electron blocking layer with a thickness of 50 Å. Compound 28:D-1 (mass ratio 75:25) of the present invention was deposited on the electron blocking layer to form a light-emitting layer with a thickness of 350 Å. HB-1 was deposited on the light-emitting layer to form a hole blocking layer with a thickness of 50 Å. An electron transport layer with a thickness of 450 Å is formed by evaporating ET-1:LiQ (mass ratio 1:1) onto a hole blocking layer. An electron injection layer with a thickness of 10 Å is then formed by evaporating LiF onto the electron transport layer. Finally, an electron injection layer with a thickness of 1200 Å is formed by evaporating Al onto the electron injection layer. This constitutes an organic light-emitting device.

[0160]

[0161] [Examples 2-35]

[0162] Compound 63, 143, 184, 331, 384, 417, 531, 546, 558, 599, 607, 634, 643, 656, 669, 723, 753, 820, 875, 919, 925, 1017, 1037, 1049, 1056, 1067, 1098, 1181, 1229, 1395, 1444, 1457, 1478, and 1515 of the present invention were used to replace compound 28 in Example 1 as the light-emitting layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 1.

[0163] [Comparative Examples 1-7]

[0164] Compounds P-1, P-2, P-3, P-4, P-5, P-6, and P-7 were used to replace compound 28 in Example 1 as the light-emitting layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 1.

[0165] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of the organic electroluminescent devices obtained by devices 1-35 and comparative examples 1-7 in the embodiments of the present invention are shown in Table 1 below.

[0166] Table 1:

[0167]

[0168] As shown in Table 1, when the carbazole compound of the present invention is applied to the light-emitting layer of an organic electroluminescent device, the device exhibits higher luminous efficiency and longer lifespan compared to comparative compounds P-1 to P-7. The carbazole compound of the present invention is a high-performance light-emitting layer material.

[0169] [Example 36]

[0170] The glass substrate was cleaned with distilled water and ultrasonically. After distilled water washing, ultrasonic cleaning was performed using solvents such as isopropanol, acetone, and methanol, followed by drying. After drying, the substrate was transferred to a plasma cleaner, and then transferred to an evaporation deposition machine. Indium tin oxide (ITO) was coated onto the glass substrate to form an anode. HI-1:HT-3 (mass ratio 3:97) was deposited on the anode to form a hole injection layer with a thickness of 150 Å. HT-3 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 1100 Å. HT-2 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 100 Å. EB-2 was deposited on the second hole transport layer to form an electron blocking layer with a thickness of 50 Å. Compound 28:D-2:D-3 (mass ratio 79.3:20:0.7) of the present invention was deposited on the electron blocking layer to form a light-emitting layer with a thickness of 300 Å. HB-1 is deposited on the light-emitting layer to form a hole-blocking layer with a thickness of 50 Å. ET-2:LiQ (mass ratio 1:1) is deposited on the hole-blocking layer to form an electron transport layer with a thickness of 550 Å. LiF is deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å. Al is deposited on the electron injection layer to form a cathode with a thickness of 1200 Å. This forms an organic light-emitting device.

[0171]

[0172] [Examples 37-70]

[0173] Compound 63, 143, 184, 331, 384, 417, 531, 546, 558, 599, 607, 634, 643, 656, 669, 723, 753, 820, 875, 919, 925, 1017, 1037, 1049, 1056, 1067, 1098, 1181, 1229, 1395, 1444, 1457, 1478, and 1515 of the present invention were used to replace compound 28 in Example 36 as the light-emitting layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 36.

[0174] [Comparative Examples 8-14]

[0175] Compounds P-1, P-2, P-3, P-4, P-5, P-6, and P-7 were used to replace compound 28 in Example 36 as the light-emitting layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 36.

[0176] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics of the organic electroluminescent devices obtained in embodiments 36-70 and comparative embodiments 8-14 are shown in Table 2 below.

[0177] Table 2:

[0178]

[0179] As shown in Table 2, when the carbazole compound of the present invention is applied to the light-emitting layer of an organic electroluminescent device, the device exhibits higher luminous efficiency and longer lifespan compared to comparative compounds P-1 to P-7. The compound of the present invention is a high-performance light-emitting layer material.

[0180] [Example 71]

[0181] The glass substrate was cleaned with distilled water and ultrasonically. After distilled water washing, ultrasonic cleaning was performed using solvents such as isopropanol, acetone, and methanol, followed by drying. After drying, the substrate was transferred to a plasma cleaner, and then transferred to an evaporation deposition machine. Indium tin oxide (ITO) was coated onto the glass substrate to form an anode. HI-1:HT-4 (mass ratio 3:97) was deposited on the anode to form a hole injection layer with a thickness of 150 Å. HT-4 was deposited on the hole injection layer to form a hole transport layer with a thickness of 1200 Å. A light-emitting layer was deposited on the hole transport layer, using H-1:compound 28 of this invention (mass ratio 1:1) as the host material and doped with 5 wt% D-4 to form a light-emitting layer with a thickness of 250 Å. ET-2:LiQ (mass ratio 1:1) was deposited on the light-emitting layer to form an electron transport layer with a thickness of 350 Å. LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å. Al is deposited on the electron injection layer to form a cathode with a thickness of 1200 Å, thus forming an organic light-emitting device.

[0182]

[0183] [Examples 72-105]

[0184] Compound 63, 143, 184, 331, 384, 417, 531, 546, 558, 599, 607, 634, 643, 656, 669, 723, 753, 820, 875, 919, 925, 1017, 1037, 1049, 1056, 1067, 1098, 1181, 1229, 1395, 1444, 1457, 1478, and 1515 of the present invention were used to replace compound 28 in Example 71 as the light-emitting layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 71.

[0185] [Comparative Examples 15-21]

[0186] Compounds P-1, P-2, P-3, P-4, P-5, P-6, and P-7 were used to replace compound 28 in Example 71 as the light-emitting layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 71.

[0187] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of the organic electroluminescent devices obtained in embodiments 71-105 and comparative embodiments 15-21 are shown in Table 3 below.

[0188] Table 3:

[0189]

[0190] As shown in Table 3, when the carbazole compound of the present invention is applied to the light-emitting layer of an organic electroluminescent device, the device exhibits higher luminous efficiency and longer lifespan compared to comparative compounds P-1 to P-7. The compound of the present invention is a high-performance light-emitting layer material.

[0191] 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 compound, characterized in that, The carbazole compound has the structure represented by Formula I: Group 1: Wherein, X1 and X2 are independently selected from single bonds, O, S, and C(R). x R y Any one of X1 and X2; and one of X1 and X2 is selected from a single bond; The rings A, B, and C are independently selected from any one of the substituted or unsubstituted structures in group 1; The z is selected from C(R) t ); The R t R x R y Selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, 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 C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl, or R x R y The links between them form substituted or unsubstituted rings; The Ar1 is selected from the group shown in Formula II; The x is selected from either CH or N; X3 and X4 are independently selected from O, S, and C(R). i R j Any one of the following; and at least one of X3 and X4 is selected from any one of O and S; The R a R i R j Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C14 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; wherein R a R i R j The substituents in "substituted or unsubstituted" are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, silyl, C1-C25 alkyl, C3-C25 cycloalkyl, C1-C25 heterocyclic alkyl, C6-C30 aryl, C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, and C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups. a0 is selected from 0, 1, 2, 3, or 3; a1 is selected from 0, 1, 2, 3, or 4; when there are two or more R... a At that time, two or more R a The same or different between each other, or two adjacent R a They connect with each other to form substituted or unsubstituted aromatic rings; The L1 is selected from a single bond or any one of the following groups, or a combination of two or more of the following groups: The v and v' are independently selected from either CH or N; and at most one of the v' is selected from N. The ring D is selected from substituted or unsubstituted C3~C10 alicyclic rings; X5 and X6 are independently selected from O, S, and N(R). s Any one of the following; X7 is selected from O, S, C(R) p R q ), N(R s Any one of the following; The R b R b '、R p R q Independently selected from any one of hydrogen, deuterium, tritium, fluorine, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R p R q The connections between them form substituted or unsubstituted rings; wherein the R b The substituents in "substituted or unsubstituted" are selected from any one of hydrogen, deuterium, tritium, fluorinyl, cyano, nitro, silyl, C1-C25 alkyl, C3-C25 cycloalkyl, C1-C25 heterocycloalkyl, C6-C30 aryl, and C2-C10 heteroaryl. The R s It is independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; p is selected from 1, 2, 3, or 4; b1 is selected from 0, 1, 2, 3, or 4; b2 is selected from 0, 1, 2, 3, 4, 5, or 6; b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; b4 is selected from 0, 1, or 2; when there are two or more R... b At that time, two or more R b The same or different between each other, or two adjacent R b They connect with each other to form substituted or unsubstituted rings; The b'1 is selected from 0, 1, or 2; when there are two or more R... b At that time, two or more R b 'They may be the same as or different from each other; The condition is that it does not contain the following compounds: 、 、 。 2. The carbazole compound according to claim 1, characterized in that, The carbazole compound is selected from any one of the following structures: Ar1, L1, ring A, ring B, ring C, and R x R y The definition is the same as that in Equation I.

3. The carbazole compound according to claim 1, characterized in that, The group represented by Formula II is selected from any one of the following groups: The x is selected from either CH or N; The R a R i R j Selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, and the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl. Any one of tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, diphenylphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, perylene, fluoranthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl; wherein R a R i R j The substituents in "substituted or unsubstituted" are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, di... The following is a list of phenylsilyl, phenylsilyl, vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, and fluoranthracene; a0 is selected from 0, 1, 2, 3, or 3; a1 is selected from 0, 1, 2, 3, or 4; a2 is selected from 0, 1, 2, 3, 4, 5, or 6; a3 is selected from 0, 1, 2, 3, 4, or 5; when there are two or more R... a At that time, two or more R a The same or different between each other, or two adjacent R a They connect with each other to form substituted or unsubstituted rings.

4. A carbazole compound according to claim 1, characterized in that, The group represented by Formula II is selected from any one of the following groups: 。 5. A carbazole compound according to claim 1, characterized in that, The L1 is independently selected from a single bond or any one of the following groups, or a combination of two or more of the following groups: The R b R b '、R p R q The group is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, the group shown in Formula II, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl Alkyl, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiophene, pyrroleyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzimidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthilinyl, indoleyl; The R s The following groups are independently selected from hydrogen, deuterium, tritium, and substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl The following are all of the following: vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; b1 is selected from 0, 1, 2, 3, or 4; b2 is selected from 0, 1, 2, 3, 4, 5, or 6; b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; b4 is selected from 0, 1, or 2; b5 is selected from 0, 1, 2, or 3; b6 is selected from 0 or 1; b7 is selected from 0, 1, 2, 3, 4, or 5; b8 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when there are two or more R... b At that time, two or more R b The same or different between each other, or two adjacent R b They connect with each other to form substituted or unsubstituted rings; The b'1 is selected from 0, 1, or 2; the b'2 is selected from 0, 1, 2, 3, or 4; the b'3 is selected from 0, 1, 2, 3, 4, 5, or 6; the b'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the b'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the b'6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; when there are two or more R b At that time, two or more R b 'They are the same as or different from each other.' 6. A carbazole compound according to claim 1, characterized in that, The L1 is independently selected from a single bond or any one of the following groups, or a combination of two or more of the following groups: 。 7. A carbazole compound according to claim 1, characterized in that, The compound of formula I is selected from any one of the following structures: 。 8. An organic electroluminescent device, comprising an anode, a cathode, and an organic layer located between the anode and the cathode or on the side of the cathode facing away from the anode, characterized in that, The organic layer comprises at least one of the carbazole compounds according to any one of claims 1 to 7.

9. An organic electroluminescent device according to claim 8, wherein the organic layer is located between the anode and the cathode, characterized in that, The organic layer comprises a light-emitting layer, which comprises at least one of the carbazole compounds according to any one of claims 1 to 7.

10. An organic electroluminescent device according to claim 8, wherein the organic layer is located on the side of the cathode opposite to the anode, characterized in that, The organic layer includes a capping layer, which contains at least one of the carbazole compounds according to any one of claims 1 to 7.

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