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 excellent triplet state energy level characteristics, efficient carrier transport capability, good film-forming stability and structural durability when being applied to a light-emitting layer in a device. The luminous efficiency of the device can be greatly improved, the driving voltage is effectively reduced, and the service life of the device is prolonged. The organic electroluminescence display panel is suitable for a traditional organic electroluminescence display panel, can also be widely applied to the fields of organic light-emitting diode illumination, flexible display modules and the like, and has remarkable technical practicability and wide industrialization prospects.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs), with their self-emissive properties and unique advantages such as wide viewing angles, high contrast, fast response, and thinness and flexibility, have not only been widely used in many fields, but their application scope continues to expand. Among the many application areas, the display field is currently the most mature and widespread application area for OLED technology—it is gradually replacing some traditional display technologies such as liquid crystal displays (LCDs), and widely covering mainstream scenarios such as smartphone screens, televisions, professional monitors, and automotive displays. In the lighting field, OLED, as a new solid-state lighting technology, shows great potential compared to traditional LED lighting due to its unique "surface light source" characteristics. Its lighting panels not only emit light uniformly and softly without glare, but also have excellent color rendering index (CRI) (typically >90, close to natural light), making them particularly suitable for scenarios with high requirements for light quality, such as homes, hotels, and museums.

[0003] OLED technology is a display technology that uses organic materials to achieve self-illumination under the influence of an electric field. When an electric current passes through, electrons and holes are injected from the cathode and anode into the organic functional layer, respectively, recombine, and generate energy transitions, releasing energy in the form of photons, which in turn form visible light.

[0004] OLED light-emitting layer materials mainly include two categories: organic small molecules and polymers. According to the light-emitting mechanism, they can be divided into fluorescent materials (which only utilize singlet excitons and have low efficiency) and phosphorescent materials (which can utilize all excitons and have high efficiency). Their characteristics directly affect the light-emitting color, efficiency and lifespan of the device.

[0005] To improve the overall performance of devices, developing high-performance light-emitting layer materials to achieve higher luminous efficiency and longer lifespan is one of the important research directions at present. Summary of the Invention

[0006] Purpose of the invention: In view of the above problems, the purpose of this invention is to provide a carbazole compound and its organic electroluminescent device, so as to improve the luminous efficiency of the organic electroluminescent device and extend its service life.

[0007] This invention provides a carbazole compound, wherein the carbazole compound is selected from the structure represented by formula I:

[0008] [Formula I]

[0009]

[0010] Wherein, ring A, ring B, and ring C are the same or different from each other, and are independently substituted or unsubstituted C6-C50 aromatic hydrocarbon rings or substituted or unsubstituted C2-C40 aromatic heterocycles;

[0011] X1 and X2 are independently single bonds, CR1R2, O or S, but the case where both X1 and X2 are single bonds is excluded.

[0012] R1 to R2 are each independently selected from any one of 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 group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group, or R1 and R2 can be connected to form a substituted or unsubstituted ring;

[0013] Ar1 and Ar2 may be identical or different from each other, and are independently selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cyclic groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cyclic groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cyclic groups, substituted or unsubstituted pyridyl groups, and substituted or unsubstituted pyrimidinyl groups; at least one of Ar1 and Ar2 is...

[0014] X is selected from any one of CR3R4, NR5, O, and S;

[0015] Each of R3 to R4 is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused cycloyl, or R3 and R4 can be connected to form a substituted or unsubstituted ring; or one of R3 and R4 is a bond connected to L2 or L3;

[0016] R5 is selected from any one of hydrogen, deuterium, 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 group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group; or R5 is a bond connected to L2 or L3;

[0017] The R a 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 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;

[0018] The a1 is selected from integers from 0 to 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 rings;

[0019] L1, L2, and L3 are each independently selected from a single bond or any one of the following groups:

[0020]

[0021] The R c It is 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 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0022] The h is selected from integers from 1 to 4;

[0023] c1 is selected from integers from 0 to 4; c2 is selected from integers from 0 to 6; c3 is selected from integers from 0 to 8; c4 is selected from integers from 0 to 2; when there are two or more R c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings;

[0024] The n1 may be selected from CH or N, and at most two n1 are N;

[0025] The n2 may be selected from CH or N, either the same or different.

[0026] The Rs are either the same as or different from each other, and are independently selected from any one of the following: deuterium, tritium, halogen, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C10-C30 aryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group;

[0027] The value of m is an integer from 1 to 3.

[0028] Beneficial effects

[0029] This invention discloses a carbazole compound that possesses excellent triplet energy level characteristics, efficient carrier transport capability, and good film-forming stability and structural durability. When used as the host material for the emitting layer of organic electroluminescent devices, this compound can promote the efficient recombination of electrons and holes to form excitons, significantly improve the device's luminous efficiency, effectively reduce the driving voltage, and extend the device's lifetime. Furthermore, the synthesis process of the compound described in this invention is simple, the starting materials are readily available and cost-effective, and it requires no complex reaction conditions or special equipment, thus possessing broad prospects for industrial application. Detailed Implementation

[0030] The technical solution will be clearly and completely described below with reference to embodiments of the present invention. It should be understood that the described embodiments are only a part of the present invention and do not cover all aspects of the present invention. After reading this invention, any equivalent modifications and variations made by those skilled in the art should fall within the protection scope defined by this invention.

[0031] In the compounds of this invention, "*-" refers to the portion connected to another substituent. "*—" can be connected to any optional position of the group / segment to which it is connected.

[0032] In the compounds described herein, any atom not specified as a particular isotope includes any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances. In this invention, "H," "hydrogen," and "hydrogen atom" refer to isotopes with different numbers of neutrons, including protium, deuterium, and tritium.

[0033] In the compounds of this invention, when the bond containing the substituent or linking site extends through two or more rings, it indicates that it can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites on the rings. For example, Can represent Can represent And so on.

[0034] In the compounds of this invention, when the position of the 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. For example, Can represent Can represent Can represent And so on.

[0035] In this invention, "the formation of a ring by bonding two adjacent groups" refers to the formation of a substituted or unsubstituted hydrocarbon ring by bonding adjacent groups together and optionally aromatizing them. The hydrocarbon ring can be an aromatic hydrocarbon ring. The hydrocarbon ring can be a monocyclic or polycyclic group. Examples are shown below:

[0036]

[0037] Furthermore, a ring formed by the bonding of adjacent groups can connect with another ring to form a helical structure. See the example below:

[0038]

[0039] In this invention, the rings formed by the connection can be three-membered rings, four-membered rings, five-membered rings, six-membered rings, seven-membered rings, eight-membered rings, fused rings, spirorings, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, benzene, naphthalene, phenanthrene, triphenylene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, fluorene, etc., but are not limited to these.

[0040] The halogens described in this invention include F, Cl, Br, and I.

[0041] In the "substituted or unsubstituted" category of this invention, the substituent may be independently selected from deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C25 alkyl groups, substituted or unsubstituted C3-C25 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted groups formed by the fusion of C3-C30 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C1-C12 alkoxy groups, substituted or unsubstituted C1-C6 alkylthio groups, substituted or unsubstituted C1-C12 alkylamino groups, substituted or unsubstituted C6-C30 aryloxy groups, substituted or unsubstituted C6-C30 arylamino groups, etc., but are not limited to the above list. Furthermore, adjacent substituents may also be interconnected to form a ring. Preferred substituents 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, groups formed by the fusion of C3-C30 alicyclic rings and C6-C30 aromatic rings, C1-C12 alkoxy groups, etc. Specific examples include, but are not limited to, deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, triphenylsilyl, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, tolyl, mesitylene, pentadeuterated phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, perylene, pyrene, fluoranyl, indene, dihydroindene, dihydro Naphthyl, tetrahydronaphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirodifluorenyl, carbazolyl, 9-phenylcarbazolyl, carbazo-indole, pyrrole, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, pyridinyl, pyrimidinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazole, benzoxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, pentyl, hexylquinoxolinyl, quinazolinyl, phenothiazinyl, phenothiazinyl, acridineyl, etc., but not limited to the above list. When there are multiple substituents, the multiple substituents can be the same or different; in addition, adjacent substituents can also be linked to form a ring.

[0042] The alkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. The alkyl group can be a straight-chain alkyl group or a branched-chain alkyl group. When the chain alkyl group described in this invention has 3 or more carbon atoms, it includes its isomers. For example, propyl includes n-propyl and isopropyl; butyl includes n-butyl, isobutyl, sec-butyl, tert-butyl, and so on. The carbon atoms of the alkyl group are C1 to C30, preferably C1 to C25, more preferably C1 to C20, particularly preferably C1 to C10, and most preferably C1 to C6. Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, etc., but are not limited to the above list.

[0043] The cycloalkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from a cyclic alkane molecule, and can be saturated or partially unsaturated. Preferably, the carbon atom is C3 to C25, more preferably C3 to C12, particularly preferably C5 to C10, and most preferably C5 to C7. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited to the above list.

[0044] 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 (such as O, S, N, or P) in addition to carbon atoms. Preferably, the carbon atom is C1 to C25, more preferably C1 to C15, further preferably C2 to C12, and particularly preferably C2 to C6. Examples include piperidinyl, piperazineyl, propylidinyl, tetrahydropyrrolyl, dihydrofuran, tetrahydrofuran, dihydrothiophene, tetrahydrothiophene, morpholinyl, thiomorpholinyl, ethylene oxide, cyclothioethyl, etc., but are not limited to the above-listed groups.

[0045] The aryl group described in this invention refers to the group formed by removing a hydrogen atom from the aromatic carbon atom in an aromatic hydrocarbon molecule, and can be a monocyclic aryl or a fused-ring aryl. Preferably, the carbon atom is C6–C30, more preferably C6–C20, particularly preferably C6–C15, and most preferably C6–C12. Examples include phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorene, benzo[a]fluorene, spirodifluorene, pyrene, etc. Examples include, but are not limited to, benzo[a], fluoranthyl, etc.

[0046] The heteroaryl group described in this invention refers to a group formed by replacing one or more aromatic nucleus carbon atoms in an aryl group with heteroatoms (such as O, S, N, or P), and can be a monocyclic heteroaryl or a fused-ring heteroaryl. Preferably, the carbon atom is C2 to C30, more preferably C2 to C18, particularly preferably C2 to C15, and most preferably C2 to C12. Examples include dibenzofuranyl, dibenzothiophenyl, carbazoleyl, pyridyl, benzofuranyl, benzothiophenyl, benzocarbazoleyl, benzodibenzofuranyl, naphthodibenzofuranyl, benzodibenzothiophenyl, naphthodibenzothiophenyl, naphthocarbazoleyl, indoleyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, furanyl, benzofuranyl, thiophenyl, etc., but not limited to the above-listed groups.

[0047] The fused cyclic group of heterocyclic alkanes and aromatic rings described in this invention refers to a monovalent group formed by removing one hydrogen atom after fusion of a heterocyclic alkane and an aromatic ring. The heterocyclic alkanes preferably have C1-C25 carbon atoms, more preferably C1-C15, further preferably C2-C12, and particularly preferably C2-C6. The aromatic rings preferably have C6-C60 carbon atoms, more preferably C6-C30, more preferably C6-C20, more preferably C6-C18, and even more preferably C6-C10. Examples include benzopiperidinyl, benzomorpholinyl, benzofuranyl, naphthopyrroleyl, naphthothiophenyl, indoleyl, quinolinyl, quinazolinyl, and benzozazepine. The basics, but not limited to those listed above.

[0048] The fused alicyclic and aromatic ring group described in this invention refers to a monovalent group formed by removing one hydrogen atom after the alicyclic and aromatic rings are fused. The alicyclic ring preferably has C3-C30 carbon atoms, more preferably C3-C25, more preferably C3-C20, more preferably C3-C15, and even more preferably C3-C8. The aromatic ring preferably has C6-C60 carbon atoms, more preferably C6-C30, more preferably C6-C20, more preferably C6-C18, and even more preferably C6-C10. Examples include benzocyclopropane, benzocyclobutane, benzocyclopentane, dihydroindene, indene, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptane, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, etc., but are not limited to the above list. Preferably, the linking site of the fused alicyclic and aromatic ring group is on the aromatic ring, for example, on the benzene ring or the naphthalene ring.

[0049] The fused cyclic group of alicyclic and heteroaromatic rings described in this invention refers to a monovalent group formed by removing one hydrogen atom after the alicyclic and heteroaromatic rings are fused. The alicyclic ring preferably has carbon atoms of C3-C30, more preferably C3-C25, more preferably C3-C20, more preferably C3-C15, and even more preferably C3-C8. The heteroaromatic ring preferably has carbon atoms of C2-C30, more preferably C2-C18, particularly preferably C2-C15, and most preferably C2-C12. Examples include, but not limited to, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenecyclopropyl, dibenzothiophenecyclobutyl, dibenzothiophenecyclopentyl, dibenzothiophenecyclohexyl, dibenzothiophenecycloheptyl, carbazocyclopropyl, carbazocyclobutyl, carbazocyclopentyl, carbazocyclohexyl, carbazocycloheptyl, indolecyclobutyl, indolecyclopentyl, indolecyclohexyl, indolecycloheptyl, pyridinocyclopropyl, pyridinocyclobutyl, pyridinocyclopentyl, pyridinocyclohexyl, pyridinobenzocycloheptyl, pyrimidinocyclopropyl, pyrimidinocyclobutyl, pyrimidinocyclopentyl, pyrimidinocyclohexyl, pyrimidinobenzocycloheptyl, etc.

[0050] 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 in an aromatic hydrocarbon molecule. It can be a divalent monocyclic aryl group or a divalent fused-ring aryl group. Preferably, the carbon atom is C6–C30, more preferably C6–C25, further preferably C6–C20, particularly preferably C6–C18, and most preferably C6–C12. Examples include phenylene, biphenylene, terphenylene, naphthylene, anthraceneylene, phenanthreneylene, fluoreneylene, benzo[a]fluoreneylene, spirodifluoreneylene, pyreneylene, perylene, etc., but are not limited to the above-listed groups.

[0051] The heteroaryl group described in this invention refers to a divalent group formed by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms (such as O, S, N, or P). It can be a divalent monocyclic heteroaryl or a divalent fused-ring heteroaryl. Preferably, the carbon atom is C2–C30, more preferably C6–C20, and particularly preferably C6–C15. Examples include, but are not limited to, pyridinyl, pyrazinyl, indoleyl, benzofuranyl, benzothiophenyl, benzocarbazoyl, dibenzofuranyl, dibenzothiophenyl, dibenzocarbazoyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, bipyridinyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, quinolinyl, isoquinolinyl, etc.

[0052] The fused alicyclic and aromatic ring cyclic groups described in this invention refer to divalent groups formed by removing two hydrogen atoms after the alicyclic and aromatic rings are fused together. The alicyclic ring preferably has C3-C30 carbon atoms, more preferably C3-C25, more preferably C3-C20, more preferably C3-C15, and even more preferably C3-C8. The aromatic ring preferably has C6-C60 carbon atoms, more preferably C6-C30, more preferably C6-C20, more preferably C6-C18, and even more preferably C6-C10. Examples include benzo[a]cyclopropane, benzo[a]cyclobutane, dihydroindene, indene, tetrahydronaphthyl, dihydronaphthyl, benzo[a]cycloheptane, benzo[a]cyclobutenyl, benzo[a]cycloheptenyl, etc., but are not limited to the above-listed examples.

[0053] The "substituted or unsubstituted silyl group" mentioned in this invention refers to the -Si(Rn)3 group, wherein each Rn may be the same or different, and is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted groups formed by the fusion of C3-C30 alicyclic rings and C6-C30 aromatic rings, substituted or unsubstituted groups formed by the fusion of C1-C25 heterocyclic alkanes and C6-C30 aromatic rings, and substituted or unsubstituted groups formed by the fusion of C3-C25 alicyclic rings and C2-C30 heteroaryl rings. Examples include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, and tripyridylsilyl.

[0054] This invention provides a carbazole compound having the structure represented by Formula I:

[0055] [Formula I]

[0056]

[0057] The rings A, B, and C are either the same as or different from each other, and are independently substituted or unsubstituted C6-C50 aromatic hydrocarbon rings or substituted or unsubstituted C2-C40 aromatic heterocycles.

[0058] X1 and X2 are independently single bonds, CR1R2, O or S, but the case where both X1 and X2 are single bonds is excluded.

[0059] R1 to R2 are each independently selected from any one of 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 group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group, or R1 and R2 can be connected to form a substituted or unsubstituted ring;

[0060] Ar1 and Ar2 may be identical or different from each other, and are independently selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cyclic groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cyclic groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cyclic groups, substituted or unsubstituted pyridyl groups, and substituted or unsubstituted pyrimidinyl groups; at least one of Ar1 and Ar2 is...

[0061] X is selected from any one of CR3R4, NR5, O, and S;

[0062] Each of R3 to R4 is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused cycloyl, or R3 and R4 can be connected to form a substituted or unsubstituted ring; or one of R3 and R4 is a bond connected to L2 or L3;

[0063] R5 is selected from any one of hydrogen, deuterium, 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 group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group; or R5 is a bond connected to L2 or L3;

[0064] The R a 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 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;

[0065] The a1 is selected from integers from 0 to 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 rings;

[0066] L1, L2, and L3 are each independently selected from a single bond or any one of the following groups:

[0067]

[0068] The R c It is 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 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0069] The h is selected from integers from 1 to 4;

[0070] c1 is selected from integers from 0 to 4; c2 is selected from integers from 0 to 6; c3 is selected from integers from 0 to 8; c4 is selected from integers from 0 to 2; when there are two or more R c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings;

[0071] The n1 may be selected from CH or N, and at most two n1 are N;

[0072] The n2 may be selected from CH or N, either the same or different.

[0073] The Rs are either the same as or different from each other, and are independently selected from any one of the following: deuterium, tritium, halogen, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C10-C30 aryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group;

[0074] The value of m is an integer from 1 to 3.

[0075] Preferably, the carbazole compound has a structure represented by Formula I-1:

[0076] [Formula I-1]

[0077]

[0078] The definitions of ring A, ring B, ring C, X1, X2, Ar1, Ar2, L1, L2, L3, R, and m are the same as those in Equation I.

[0079] Preferably, the Selected from the following groups:

[0080]

[0081] The R a'Each is 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 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;

[0082] The R a The definitions of R3 to R5 are the same as those in Equation I;

[0083] a1 is selected from integers from 0 to 4; a2 is selected from integers from 0 to 3; 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;

[0084] a'1 is selected from integers from 0 to 8; a'2 is selected from integers from 0 to 6; a'3 is selected from integers from 0 to 10; a'4 is selected from integers from 0 to 14; when there are two or more R a At that time, two or more R a 'Same or different from each other'.

[0085] Preferably, the Selected from the following groups:

[0086]

[0087]

[0088] The R a R a R3 to R4 are 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 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;

[0089] The R5 is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, 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;

[0090] a1 is selected from integers from 0 to 7; a2 is selected from integers from 0 to 9; a3 is selected from integers from 0 to 11; a4 is selected from integers from 0 to 13; a5 is selected from integers from 0 to 3; a6 is selected from integers from 0 to 8; a7 is selected from integers from 0 to 4; a8 is selected from integers from 0 to 10; a9 is selected from integers from 0 to 12; a 10 Integers selected from 0 to 14; 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;

[0091] a'1 is selected from integers from 0 to 8; a'2 is selected from integers from 0 to 6; a'3 is selected from integers from 0 to 10; a'4 is selected from integers from 0 to 14; a'5 is selected from integers from 0 to 4; a'6 is selected from integers from 0 to 2; when there are two or more R a At that time, two or more R a 'Same or different from each other'.

[0092] Preferably, Ar1 and Ar2 are not... It is independently selected from the following groups:

[0093]

[0094] The R bIndependently 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 alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl;

[0095] b2 is selected from integers from 0 to 5; 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.

[0096] Preferably, the Selected from the following groups:

[0097]

[0098]

[0099] The R b R a Each is 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 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;

[0100] The R6 is selected from any one of hydrogen, deuterium, 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 group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group;

[0101] b1 is selected from integers from 0 to 5; b2 is selected from integers from 0 to 7; b3 is selected from integers from 0 to 9; b4 is selected from integers from 0 to 4; b5 is selected from integers from 0 to 3; b6 is selected from integers from 0 to 6; b7 is selected from integers from 0 to 11; 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;

[0102] a'1 is selected from integers from 0 to 8; a'2 is selected from integers from 0 to 6; a'3 is selected from integers from 0 to 10; a'4 is selected from integers from 0 to 4; a'5 is selected from integers from 0 to 2; when there are two or more R a At that time, two or more R a 'Same or different from each other'.

[0103] Preferably, L1, L2, and L3 are each independently selected from a single bond or any one of the following groups, or a combination of two or more of the following groups:

[0104]

[0105]

[0106] The R c R aEach is 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 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;

[0107] c1 is selected from integers from 0 to 4; c2 is selected from integers from 0 to 6; c3 is selected from integers from 0 to 8; c4 is selected from integers from 0 to 2; c5 is selected from integers from 0 to 3; c6 is selected from integers from 0 to 5; c7 is selected from integers from 0 to 7; when there are two or more R c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings;

[0108] a'1 is selected from integers from 0 to 8; a'2 is selected from integers from 0 to 6; a'3 is selected from integers from 0 to 10; a'4 is selected from integers from 0 to 4; a'5 is selected from integers from 0 to 2; when there are two or more R a At that time, two or more R a 'Same or different from each other'.

[0109] Preferably, when R c When the a'1 is selected from substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cyclic groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic fused cyclic groups, or substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused cyclic groups, the a'1 is selected from 1; the a'2 is selected from 1; the a'3 is selected from 1; the a'4 is selected from 1; and the a'5 is selected from 1.

[0110] Preferably, the Rs are the same or different from each other and are independently selected from any one of deuterium, tritium, substituted or unsubstituted C1 to C6 alkyl groups.

[0111] Preferably, when R is selected from deuterium or tritium, m is selected from 3.

[0112] Preferably, when R is selected from substituted or unsubstituted C1 to C6 alkyl groups, m is selected from 1, 2 or 3.

[0113] Preferably, ring A, ring B, and ring C are the same or different from each other, and are independently any one of the following: substituted or unsubstituted benzene ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted phenanthrene ring, substituted or unsubstituted anthracene ring, substituted or unsubstituted pyridine ring, substituted or unsubstituted pyrazine ring, substituted or unsubstituted pyridazine ring, substituted or unsubstituted quinoline ring, substituted or unsubstituted isoquinoline ring, substituted or unsubstituted quinazoline ring, and substituted or unsubstituted quinoxaline ring.

[0114] Most preferably, the compound of formula I is selected from any one of the following structures:

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160] 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.

[0161] 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.

[0162] 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.

[0163] More preferably, the light-emitting layer comprises a host material, which comprises at least one of the carbazole compounds described in this invention.

[0164] The anode described in this invention is preferably made of a high work function material that can efficiently reduce the hole injection barrier and improve the carrier injection efficiency. The material types include metals, metal oxides, alloys, or composite multilayer structures, specifically indium tin oxide (ITO), indium zinc oxide (IZO), graphene, aluminum-doped zinc oxide (AZO), gold (Au), platinum (Pt), tungsten (W), molybdenum oxide-silver-molybdenum oxide (MoO3-Ag-MoO3), aluminum-nickel-molybdenum oxide (Al / Ni / MoO3), etc. The anode structure design can be flexibly adjusted; it can be a single-layer structure of a single material (such as a pure Au single layer), or a multilayer composite structure to optimize performance, such as an Al / Cu / MoO3 three-layer structure, an ITO / MoO3 two-layer structure, etc., and is not limited to the structural forms listed above.

[0165] The hole injection layer described in this invention is preferably made of a material with high conductivity, good film-forming properties, and the ability to effectively modify the surface energy level of the anode. Suitable material categories include aromatic amine derivatives, conjugated polymers, metal oxides, and organic small molecule acceptor materials. Specific examples include 4,4',4”-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile (HATCN), copper phthalocyanine (CuPC), tetrafluorotetracyano-p-benzoquinone dimethyl ether (F4-TCNQ), poly(3,4-ethylenedioxythiophene)-poly(styrene sulfonate) (PEDOT:PSS), molybdenum oxide (MoO3), tungsten trioxide (WO3), vanadium pentoxide (V2O5), etc., and the material selection is not limited to these.

[0166] The hole transport layer described in this invention is preferably made of a material with high hole mobility, excellent thermal stability, and chemical stability. Applicable materials are mainly divided into two categories: small molecule materials and polymer materials, such as N,N'-di(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 1,1-bis[4-[N,N-di(p-tolyl)amino]phenyl]cyclohexane (TAPC), 1,3-di(carbazole-9-yl)benzene (mCP), poly(9-vinylcarbazole) (PVK), etc., and are not limited to the above materials.

[0167] The electron blocking layer described in this invention is preferably made of a material that simultaneously possesses high hole transport efficiency and strong electron blocking capability. Suitable material categories include triarylamine derivatives, carbazole derivatives, spirocyclic aromatic hydrocarbon derivatives, etc. Specific examples include 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 1,3-di(carbazole-9-yl)phenyl (mCP), 1,1-bis[4-[N,N-di(p-tolyl)amino]phenyl]cyclohexane (TAPC), N,N'-di(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine (NPB), etc., and the choice of material is not limited to these.

[0168] The luminescent layer described in this invention can adopt a binary system of "host material-doped material" or a multi-component system of "multiple host materials-multiple doped materials" designed according to luminescence requirements, in order to achieve properties such as broadband luminescence, high color purity, or high quantum efficiency. The doped materials can be classified according to the luminescence mechanism into fluorescent materials, phosphorescent materials, or thermally activated delayed fluorescence (TADF) materials.

[0169] Fluorescent doping materials: polycyclic aromatic hydrocarbon derivatives, styrene derivatives, nitrogen-containing heterocyclic derivatives, etc. can be selected, such as 4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulonidin-9-enyl)-4H-pyran (DCJTB), diphenyl anthracene derivative (DSA-ph), 2,5,8,11-tetratert-butylperylene (TBPe), 4,4'-bis(9-ethyl-3-carbazolevinyl)-1,1'-biphenyl (BCzVBi), etc.

[0170] Phosphorescent doped materials: mainly complexes containing heavy metals (such as iridium, platinum, osmium, etc.), for example, bis(4,6-difluorophenylpyridine-N,C 2+ )Pyridinecarboxylated iridium (FIr6), tris(1-phenylisoquinoline) iridium (Ir(piq)3), bis(2-benzo[b]thiophene-2-ylpyridine) acetylacetone iridium (Ir(bt)2(acac)), tris(2-phenylpyridine) iridium (Ir(ppy)3), etc.;

[0171] Main materials: In addition to the carbazole compound provided by the present invention, polycyclic aromatic hydrocarbon derivatives, heterocyclic compounds, etc., can also be selected, such as 4,4'-bis(carbazole-9-yl)biphenyl (CBP), bis-[2-(diphenylphosphoxy)phenyl] ether (DPEPO), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), etc., and the carbazole compound described in the present invention is preferred to improve the energy level matching degree and stability between the light-emitting layer and the adjacent functional layer.

[0172] The hole blocking layer described in this invention preferably possesses a high hole blocking energy barrier and is made of a material that can achieve good energy level matching with the light-emitting layer and the electron transport layer. Suitable material categories include metal complexes, nitrogen-containing heterocyclic derivatives, triazine derivatives, oxazole derivatives, etc. Specific examples include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (BPhen), 1,3,5-tris(2-benzimidazolyl)benzene (TPBi), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-phenol)aluminum (BAlq), 1,3-bis(N-carbazolyl)benzene (mCBP), etc., and the material selection is not limited to these.

[0173] The electron transport layer described in this invention is preferably made of a material with high electron mobility, good thin film morphology stability, and the ability to effectively transport electrons to the light-emitting layer. Applicable materials include nitrogen-containing heterocyclic derivatives, triazole derivatives, and silicon heterocyclic compounds, such as tris(8-hydroxyquinoline)aluminum (Alq3), bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 4,7-diphenyl-1,10-phenanthroline (BPhen), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (TAZ), and are not limited to the above materials.

[0174] The electron injection layer described in this invention is preferably made of a material that can reduce the energy level difference between the cathode and the electron transport layer and promote efficient electron injection. The material can be an insulating salt, a metal-doped material, or a metal oxide, such as lithium (Li), cesium (Cs), lithium fluoride (LiF), cesium fluoride (CsF), cesium carbonate (Cs₂CO₃), zinc oxide (ZnO), calcium fluoride (CaF₂), lithium 8-hydroxyquinoline (LiQ), and polyethyleneimine (PEIE), and the choice of material is not limited to these.

[0175] The cathode described in this invention is preferably a material with low work function and high conductivity. Suitable materials include low work function metals, alloys, metal-semiconductor composites, or multilayer composite structures, such as aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), magnesium-silver (Mg-Ag) alloys, aluminum-lithium (Al-Li) alloys, LiF / Al bilayer structures, etc., and are not limited to the materials and structures listed above.

[0176] The capping material described in this invention preferably possesses light extraction enhancement capabilities, reduces internal light reflection loss, and protects the device from external environmental interference. Besides the carbazole compound provided in this invention, aromatic amine compounds, metal compounds, etc., can also be used. Specific examples include titanium dioxide (TiO2), zirconium oxide (ZrO), N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (NPB), and 48-hydroxyquinoline aluminum (Alq3), etc. The carbazole compound described in this invention is preferred to improve the compatibility and optical matching between the capping layer and other functional layers of the device.

[0177] Synthesis Examples

[0178] The following is a 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 synthesized stepwise via the reaction route shown below. The substituents in the compound can be synthesized by organic synthesis methods known in the art. In addition, the type, substitution position, and substitution amount of the substituents can be flexibly adjusted according to the performance requirements of the target compound, combined with known synthesis techniques in the art, so as to achieve precise control of the photoelectric properties of the compound.

[0179] [Synthesis Route]

[0180] Route 1: When Ar1 and Ar2 are the same and L2 is a single bond:

[0181]

[0182] Route 2: When Ar1 and Ar2 are the same and L2 is not a single bond:

[0183]

[0184] Route 3: When Ar1 and Ar2 are different and L2 is a single bond:

[0185]

[0186] Route 4: When Ar1 and Ar2 are different and L2 is not a single bond:

[0187]

[0188] X a ~X e It is selected from any one of Cl, Br, and I; the limitations of ring A, ring B, ring C, Ar1, Ar2, L1, L2, and L3 are the same as those described above.

[0189] Description of raw materials, reagents and characterization equipment: The present invention does not impose any particular restrictions on the source of the raw materials and reagents used in the following embodiments, which can be commercially available products or prepared by methods known to those skilled in the art.

[0190] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0191] Elemental analysis was performed using a VarioELcube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0192] Synthesis Example 1: Preparation of Intermediate d-95

[0193]

[0194] Under nitrogen protection, d1-95 (12.69 g, 40 mmol), c-95 (6.48 g, 40 mmol), and K2CO3 (11.06 g, 80.00 mmol) were dissolved in 200 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl2 (585 mg, 0.80 mmol) was added with stirring, and the mixture was heated under reflux for 4 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 at a ratio of 9:1 to obtain intermediate d-95 (9.72 g, yield 79%); HPLC purity ≥ 99.89%. Mass spectrometry m / z: 305.9801 (theoretical value: 305.9811).

[0195] Synthesis Example 2: Preparation of Intermediate d-679

[0196]

[0197] According to the preparation method of intermediate d-95 in Synthesis Example 1, c-95 was replaced with an equimolar amount of c-679 to obtain intermediate d-679 (16.20 g). The purity of the solid was ≥99.95% as determined by HPLC. Mass spectrometry m / z: 524.0372 (theoretical value: 524.0363).

[0198] Synthesis Example 3: Preparation of Intermediate A-774

[0199]

[0200] Following the preparation method of intermediate d-95 in Synthesis Example 1, d1-95 and c-95 were replaced with equimolar amounts of A1-774 and c-774 to obtain intermediate A-774 (10.61 g). HPLC analysis showed that the solid purity was ≥99.95%. Mass spectrometry m / z: 348.0746 (theoretical value: 348.0739).

[0201] Synthesis Example 4: Preparation of Intermediate e-1542

[0202]

[0203] According to the preparation method of intermediate d-95 in Synthesis Example 1, d1-95 and c-95 were replaced with equimolar amounts of e1-1542 and c-110 to obtain intermediate e-1542 (32.31 g). The purity of the solid was ≥99.96% as determined by HPLC. Mass spectrometry m / z: 1090.4636 (theoretical value: 1090.4648).

[0204] Synthesis Example 5: Preparation of Intermediate e-1556

[0205]

[0206] According to the preparation method of intermediate d-95 in Synthesis Example 1, d1-95 and c-95 were replaced with equimolar amounts of e1-1556 and c-1556 to obtain intermediate e-1556 (12.17 g). The purity of the solid was ≥99.94% as determined by HPLC. Mass spectrometry m / z: 405.1559 (theoretical value: 405.1549).

[0207] Synthesis Example 6: Preparation of Intermediate e-1589

[0208]

[0209] According to the preparation method of intermediate d-95 in Synthesis Example 1, d1-95 and c-95 were replaced with equimolar amounts of e1-1589 and c-774 to obtain intermediate e-1589 (12.27 g). The purity of the solid was ≥99.96% as determined by HPLC. Mass spectrometry m / z: 403.1387 (theoretical value: 403.1395).

[0210] Synthesis Example 7: Preparation of Compound 1

[0211]

[0212] Preparation of intermediate B-1

[0213] Under nitrogen protection, A-1 (28.37 g, 140.00 mmol), pinacol diborate (35.55 g, 140.00 mmol), KOAc (27.48 g, 280.00 mmol), Pd(PPh3)4 (1.62 g, 1.4 mmol), and 1,4-dioxane (600 ml) were added to a reaction flask, and the mixture was stirred under reflux for 6 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid obtained by recrystallization from toluene / n-hexane at a ratio of 5:1 to give intermediate B-1 (31.71 g, yield 77%); HPLC purity ≥ 99.85%.

[0214] Preparation of intermediate C-1

[0215] Under nitrogen protection, B-1 (29.42 g, 100.00 mmol), b-1 (13.67 g, 50 mmol), K2CO3 (29.02 g, 210.00 mmol), Pd(dppf)Cl2 (805 mg, 1.1 mmol), and 400 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask, and the mixture was stirred under reflux for 6 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid obtained by toluene / n-hexane in a 7:1 ratio to give intermediate C-1 (17.02 g, yield 76%); HPLC purity ≥ 99.91%.

[0216] Preparation of Compound 1

[0217] Under nitrogen protection, C-1 (13.44 g, 30.00 mmol), e-1 (7.72 g, 30.00 mmol), sodium tert-butoxide (4.81 g, 50.00 mmol), Pd2(dba)3 (275 mg, 0.30 mmol), X-Phos (286 mg, 0.60 mmol), and toluene (400 ml) were added to a reaction flask, and the mixture was stirred under reflux for 8 hours. 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. The mixture was recrystallized from toluene to give compound 1 (15.05 g, 75% yield). HPLC analysis showed that the solid purity was ≥99.96%. Mass spectrometry m / z: 668.2179 (theoretical value: 668.2168). Theoretical elemental content (%) C 48 H 24 D3NO3: C, 86.21; H, 4.52; N, 2.09. Measured elemental content (%): C, 86.23; H, 4.50; N, 2.07.

[0218] Synthesis Example 8: Preparation of Compound 52

[0219]

[0220] Preparation of intermediate C-1

[0221] According to the preparation method of intermediate C-1 in Synthesis Example 1, intermediate C-1 (17.02 g, yield 76%) was obtained; HPLC purity ≥ 99.91%.

[0222] Preparation of intermediate D-52

[0223] Under nitrogen protection, C-1 (15.68 g, 35 mmol), pinacol diborate (10.67 g, 42 mmol), KOAc (6.87 g, 70 mmol), Pd(PPh3)4 (404 g, 0.35 mmol), and 1,4-dioxane (400 ml) were added to a reaction flask, and the mixture was stirred under reflux for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid obtained by recrystallization from toluene / n-hexane at a ratio of 5:1 to give intermediate D-52 (14.44 g, yield 72%); HPLC purity ≥ 99.92%.

[0224] Preparation of intermediate E-52

[0225] Under nitrogen protection, D-52 (14.32 g, 25.00 mmol), d-52 (7.94 g, 25 mmol), K2CO3 (6.91 g, 50 mmol), Pd(dppf)Cl2 (183 mg, 0.25 mmol), and 400 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask, and the mixture was stirred under reflux for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid obtained by toluene / n-hexane in a 7:1 ratio to give intermediate E-52 (12.19 g, yield 75%); HPLC purity ≥ 99.90%.

[0226] Preparation of compound 52

[0227] Under nitrogen protection, E-52 (9.75 g, 15.00 mmol), e-52 (3.86 g, 15.00 mmol), sodium tert-butoxide (3.36 g, 35.00 mmol), Pd2(dba)3 (165 mg, 0.18 mmol), X-Phos (143 mg, 0.30 mmol), and toluene (300 ml) were added to a reaction flask and stirred under reflux for 3 hours. 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. The mixture was recrystallized from toluene to give compound 52 (10.19 g, 78% yield). HPLC analysis showed that the solid purity was ≥99.95%. Mass spectrometry m / z: 870.2974 (theoretical value: 870.2962). Theoretical elemental content (%) C 64 H 34 D3NO3: C, 88.25; H, 4.63; N, 1.61. Measured elemental content (%): C, 88.23; H, 4.60; N, 1.60.

[0228] Synthesis Example 9: Preparation of Compound 58

[0229]

[0230] According to the preparation method of compound 52 in Synthesis Example 8, d-52 was replaced with an equimolar amount of d-58 to obtain compound 58 (9.49 g). HPLC analysis showed that the solid purity was ≥99.96%. Mass spectrometry m / z: 821.2743 (theoretical value: 821.2758). Theoretical elemental content (%) C 59 H 31 D3N2O3: C, 86.22; H, 4.54; N, 3.41. Measured elemental content (%): C, 86.24; H, 4.51; N, 3.43.

[0231] Synthesis Example 10: Preparation of Compound 95

[0232]

[0233] Following the preparation method of compound 52 in Synthesis Example 8, d-52 was replaced with an equimolar amount of d-95 to obtain compound 95 (9.69 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 860.3131 (theoretical value: 860.3118). Theoretical elemental content (%) C 63 H 36 D3NO3: C, 87.88; H, 4.92; N, 1.63. Measured elemental content (%): C, 87.89; H, 4.95; N, 1.60.

[0234] Synthesis Example 11: Preparation of Compound 103

[0235]

[0236] Following the preparation method of compound 52 in Synthesis Example 8, A-1 and d-52 were replaced with equimolar amounts of A-103 and d-103, respectively, to obtain compound 103 (9.89 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 844.2814 (theoretical value: 844.2805). Theoretical elemental content (%) C 62 H 32 D3NO3: C, 88.13; H, 4.53; N, 1.66. Measured elemental content (%): C, 88.10; H, 4.55; N, 1.64.

[0237] Synthesis Example 12: Preparation of Compound 110

[0238]

[0239] According to the preparation method of compound 1 in Synthesis Example 7, A-1 and e-1 were replaced with equimolar amounts of A-110 and e-110, respectively, to obtain compound 110 (22.01 g). HPLC analysis showed that the solid purity was ≥99.95%. Mass spectrometry m / z: 844.2814 (theoretical value: 844.2805). Theoretical elemental content (%) C 66 H 48 D3NO3Si2: C, 82.12; H, 5.64; N, 1.45. Measured elemental content (%): C, 82.10; H, 5.67; N, 1.44.

[0240] Synthesis Example 13: Preparation of Compound 122

[0241]

[0242] According to the preparation method of compound 52 in Synthesis Example 8, A-1, d-52, and e-52 were replaced with equimolar amounts of A-122, d-122, and e-122, respectively, to obtain compound 122 (10.91 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 982.4050 (theoretical value: 982.4059). Theoretical elemental content (%) C 72 H 30 D 13 NO3: C, 87.96; H, 5.74; N, 1.42. Measured elemental content (%): C, 87.93; H, 5.72; N, 1.41.

[0243] Synthetic Example 14: Preparation of Compound 151

[0244]

[0245] According to the preparation method of compound 52 in Synthesis Example 8, A-1 and d-52 were replaced with equimolar amounts of A-151 and d-151, respectively, to obtain compound 151 (9.98 g). HPLC analysis showed that the solid purity was ≥99.96%. Mass spectrometry m / z: 852.2356 (theoretical value: 852.2348). Theoretical elemental content (%) C 60 H 32 D3NOS2: C, 84.48; H, 4.49; N, 1.64. Measured elemental content (%): C, 84.49; H, 4.47; N, 1.67.

[0246] Synthesis Example 15: Preparation of Compound 162

[0247]

[0248] According to the preparation method of compound 1 in Synthesis Example 7, A-1 and e-1 were replaced with equimolar amounts of A-162 and e-162, respectively, to obtain compound 162 (20.44 g). HPLC analysis showed that the solid purity was ≥99.94%. Mass spectrometry m / z: 932.2982 (theoretical value: 932.2974). Theoretical elemental content (%) C 66 H 40 D3NOS2: C, 84.95; H, 4.97; N, 1.50. Measured elemental content (%): C, 84.92; H, 4.96; N, 1.52.

[0249] Synthesis Example 16: Preparation of Compound 188

[0250]

[0251] According to the preparation method of compound 52 in Synthesis Example 8, A-1 and d-52 were replaced with equimolar amounts of A-188 and d-122, respectively, to obtain compound 188 (11.33 g). HPLC analysis showed that the solid purity was ≥99.96%. Mass spectrometry m / z: 1006.2888 (theoretical value: 1006.2879). Theoretical elemental content (%) C 70 H 38 D3N3OS2: C, 83.47; H, 4.40; N, 4.17. Measured elemental content (%): C, 83.44; H, 4.42; N, 4.15.

[0252] Synthesis Example 17: Preparation of Compound 201

[0253]

[0254] According to the preparation method of compound 1 in Synthesis Example 7, A-1 and e-1 were replaced with equimolar amounts of A-151 and e-201, respectively, to obtain compound 201 (17.57 g). HPLC analysis showed that the solid purity was ≥99.96%. Mass spectrometry m / z: 750.1889 (theoretical value: 750.1879). Theoretical elemental content (%) C 52 H 26 D3NOS2: C, 83.17; H, 4.29; N, 1.87. Measured elemental content (%): C, 83.19; H, 4.28; N, 1.89.

[0255] Synthesis Example 18: Preparation of Compound 215

[0256]

[0257] Following the preparation method of compound 1 in Synthesis Example 7, A-1 and e-1 were replaced with equimolar amounts of A-215 and e-52, respectively, to obtain compound 215 (19.94 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 862.2965 (theoretical value: 862.2976). Theoretical elemental content (%) C 60 H 22 D 13 NOS2: C, 83.49; H, 5.60; N, 1.62. Measured elemental content (%): C, 83.47; H, 5.63; N, 1.60.

[0258] Synthesis Example 19: Preparation of Compound 226

[0259]

[0260] Preparation of intermediate B-226

[0261] According to the preparation method of intermediate B-1 in synthesis example 7, A-1 was replaced with an equimolar amount of A-226 to obtain intermediate B-226 (41.62 g, yield 75%); HPLC purity ≥ 99.92%.

[0262] Preparation of intermediate C1-226

[0263] Under nitrogen protection, B-226 (39.63 g, 100.00 mmol), b-226 (32.04 g, 100 mmol), K₂CO₃ (29.02 g, 210.00 mmol), Pd(dppf)Cl₂ (805 mg, 1.1 mmol), and 400 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask, and the mixture was stirred under reflux for 7 hours. 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 / n-hexane in a 7:1 ratio to give intermediate C₁-226 (33.79 g, yield 73%); HPLC purity ≥ 99.92%.

[0264] Preparation of intermediate C-226

[0265] Under nitrogen protection, C1-226 (27.77 g, 60.00 mmol), B1-226 (19.21 g, 60 mmol), K2CO3 (16.59 g, 120.00 mmol), Pd(dppf)Cl2 (439 mg, 0.6 mmol), and 400 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask, and the mixture was stirred under reflux for 6 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid obtained by recrystallization from toluene / n-hexane in a 7:1 ratio to give intermediate C-226 (24.89 g, yield 72%); HPLC purity ≥ 99.92%.

[0266] Preparation of compound 226

[0267] Under nitrogen protection, C-226 (17.29 g, 30.00 mmol), e-52 (7.72 g, 30.00 mmol), sodium tert-butoxide (4.81 g, 50.00 mmol), Pd2(dba)3 (275 mg, 0.30 mmol), X-Phos (286 mg, 0.60 mmol), and toluene (400 ml) were added to a reaction flask and stirred under reflux for 7 hours. 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. The mixture was recrystallized from toluene to give compound 226 (17.93 g, 75% yield). HPLC analysis showed that the solid purity was ≥99.95%. Mass spectrometry m / z: 796.3520 (theoretical value: 796.3533). Theoretical elemental content (%) C 60 H 40 D3NO: C, 90.42; H, 5.82; N, 1.76. Measured elemental content (%): C, 90.44; H, 5.85; N, 1.77.

[0268] Synthesis Example 20: Preparation of Compound 284

[0269]

[0270] According to the preparation method of compound 52 in Synthesis Example 8, A-1, d-52, and e-52 were replaced with equimolar amounts of A-284, d-284, and e-110, respectively, to obtain compound 284 (11.23 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 1024.4481 (theoretical value: 1024.4472). Theoretical elemental content (%) C 78 H 52 D3NO: C, 91.37; H, 5.70; N, 1.37. Measured elemental content (%): C, 91.35; H, 5.74; N, 1.34.

[0271] Synthesis Example 21: Preparation of Compound 315

[0272]

[0273] According to the preparation method of compound 52 in Synthesis Example 8, A-1 and d-52 were replaced with equimolar amounts of A-315 and d-103, respectively, to obtain compound 315 (10.20 g). HPLC analysis showed that the solid purity was ≥99.95%. Mass spectrometry m / z: 894.3423 (theoretical value: 894.3438). Theoretical elemental content (%) C 66 H 38 D3N3O: C, 88.56; H, 4.95; N, 4.69. Measured elemental content (%): C, 88.54; H, 4.92; N, 4.72.

[0274] Synthesis Example 22: Preparation of Compound 370

[0275]

[0276]

[0277] According to the preparation method of compound 52 in Synthesis Example 8, b-1, d-52, and e-52 were replaced with equimolar amounts of b-370, d-370, and e-1, respectively, to obtain compound 370 (9.43 g). HPLC analysis showed that the solid purity was ≥99.97%. Mass spectrometry m / z: 805.2607 (theoretical value: 805.2617). Theoretical elemental content (%) C 59 H 35 D3NO3: C, 87.93; H, 4.38; N, 1.74. Measured elemental content (%): C, 87.90; H, 4.41; N, 1.72.

[0278] Synthesis Example 23: Preparation of Compound 436

[0279]

[0280] According to the preparation method of compound 52 in Synthesis Example 8, A-1, b-1, d-52, and e-52 were replaced with equimolar amounts of A-436, b-436, d-436, and e-162, respectively, to obtain compound 436 (12.93 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 1179.4427 (theoretical value: 1179.4440). Theoretical elemental content (%) C 91 H 57NO: C, 92.59; H, 4.87; N, 1.19. Measured elemental content (%): C, 92.61; H, 4.88; N, 1.16.

[0281] Synthesis Example 24: Preparation of Compound 448

[0282]

[0283] Following the preparation method of compound 52 in Synthesis Example 8, A-1, b-1, and d-52 were replaced with equimolar amounts of A-315, b-436, and d-448, respectively, to obtain compound 448 (10.93 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 983.3891 (theoretical value: 983.3876). Theoretical elemental content (%) C 73 H 49 N3O: C, 89.09; H, 5.02; N, 4.27. Measured elemental content (%): C, 89.11; H, 5.05; N, 4.25.

[0284] Synthesis Example 25: Preparation of Compound 459

[0285]

[0286] According to the preparation method of compound 226 in synthesis example 19, A-226 was replaced with an equimolar amount of A-459 to obtain compound 459 (15.43 g). HPLC analysis showed that the solid purity was ≥99.95%. Mass spectrometry m / z: 676.2978 (theoretical value: 676.2989). Theoretical elemental content (%) C 48 H 36 D3NOSi: C, 85.17; H, 6.25; N, 2.07. Measured elemental content (%): C, 85.14; H, 6.26; N, 2.09.

[0287] Synthesis Example 26: Preparation of Compound 472

[0288]

[0289] According to the preparation method of compound 226 in Synthesis Example 19, A-226 and B1-226 were replaced with equimolar amounts of A-472 and B1-472 to obtain compound 472 (16.84 g). HPLC analysis showed that the solid purity was ≥99.94%. Mass spectrometry m / z: 728.2556 (theoretical value: 728.2543). Theoretical elemental content (%) C 54 H 28D3NO2: C, 88.99; H, 4.70; N, 1.92. Measured elemental content (%): C, 88.97; H, 4.71; N, 1.93.

[0290] Synthesis Example 27: Preparation of Compound 489

[0291]

[0292] According to the preparation method of compound 226 in Synthesis Example 19, A-226 and B1-226 were replaced with equimolar amounts of A-151 and B1-489 to obtain compound 489 (16.82 g). HPLC analysis showed that the solid purity was ≥99.97%. Mass spectrometry m / z: 718.2173 (theoretical value: 718.2158). Theoretical elemental content (%) C 52 H 26 D3NOS: C, 86.88; H, 4.49; N, 1.95. Measured elemental content (%): C, 86.87; H, 4.47; N, 1.97.

[0293] Synthesis Example 28: Preparation of Compound 510

[0294]

[0295] Preparation of intermediate C-510

[0296] According to the preparation method of intermediate C-510 in synthesis example 19, A-226, b-226, and B1-226 were replaced with equimolar amounts of A-1, b-510, and B1-510 to obtain intermediate C-510 (26.08 g). The purity of the solid was determined by HPLC to be ≥99.93%.

[0297] Preparation of compound 510

[0298] According to the preparation method of compound 52 in Synthesis Example 8, C-1, d-52, and e-52 were replaced with equimolar amounts of C-510, d-103, and e-510, respectively, to obtain compound 510 (10.79 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 958.3546 (theoretical value: 958.3559). Theoretical elemental content (%) C 71 H 46 N2O2: C, 88.91; H, 4.83; N, 2.92; . Measured elemental content (%): C, 88.90; H, 4.81; N, 2.90.

[0299] Synthesis Example 29: Preparation of Compound 511

[0300]

[0301] According to the preparation method of compound 510 in Synthesis Example 28, A-1, b-510, B1-510, d-510, and e-510 were replaced with equimolar amounts of A-315, b-226, B1-226, d-370, and e-52, respectively, to obtain compound 511 (10.08 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 895.3649 (theoretical value: 895.3642). Theoretical elemental content (%) C 67 H 41 D3N2O: C, 89.80; H, 5.29; N, 3.13. Measured elemental content (%): C, 89.81; H, 5.27; N, 3.15.

[0302] Synthesis Example 30: Preparation of Compound 540

[0303]

[0304] Following the preparation method of compound 226 in Synthesis Example 19, A-226, b-226, and B1-226 were replaced with equimolar amounts of A-540, b-510, and B1-540 to obtain compound 540 (15.91 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 697.2450 (theoretical value: 697.2439). Theoretical elemental content (%) C 50 H 35 NOS: C, 86.05; H, 5.06; N, 2.01. Measured elemental content (%): C, 86.07; H, 5.08; N, 2.02.

[0305] Synthesis Example 31: Preparation of Compound 563

[0306]

[0307] According to the preparation method of compound 226 in Synthesis Example 19, A-226, b-226, and B1-226 were replaced with equimolar amounts of A-563, b-563, and B1-563 to obtain compound 563 (17.98 g). HPLC analysis showed that the solid purity was ≥99.95%. Mass spectrometry m / z: 820.3512 (theoretical value: 820.3502). Theoretical elemental content (%) C 62 H 36 D5NO: C, 90.70; H, 5.65; N, 1.71. Measured elemental content (%): C, 90.72; H, 5.63; N, 1.74.

[0308] Synthesis Example 32: Preparation of Compound 597

[0309]

[0310] According to the preparation method of compound 510 in Synthesis Example 28, A-1, B1-510, d-510, and e-510 were replaced with equimolar amounts of A-315, B1-597, d-597, and e-52, respectively, to obtain compound 597 (10.72 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 978.4556 (theoretical value: 978.4549). Theoretical elemental content (%) C 73 H 58 N₂O: C, 89.54; H, 5.97; N, 2.86. Measured elemental content (%): C, 89.52; H, 5.99; N, 2.89.

[0311] Synthesis Example 33: Preparation of Compound 651

[0312]

[0313]

[0314] According to the preparation method of compound 52 in Synthesis Example 8, d-52 and e-52 were replaced with equimolar amounts of d-651 and e-651, respectively, to obtain compound 651 (10.27 g). HPLC analysis showed that the solid purity was ≥99.96%. Mass spectrometry m / z: 912.2876 (theoretical value: 912.2890). Theoretical elemental content (%) C 66 H 36 D3NO2S: C, 86.81; H, 4.64; N, 1.53. Measured elemental content (%): C, 86.83; H, 4.65; N, 1.51.

[0315] Synthesis Example 34: Preparation of Compound 679

[0316]

[0317] According to the preparation method of compound 52 in Synthesis Example 8, d-52 and e-52 were replaced with equimolar amounts of d-679 and e-651, respectively, to obtain compound 679 (11.67 g). HPLC analysis showed that the solid purity was ≥99.93%. Mass spectrometry m / z: 1094.3431 (theoretical value: 1094.3442). Theoretical elemental content (%) C 78 H 46 D3NO2SSi: C, 85.53; H, 4.78; N, 1.28. Measured elemental content (%): C, 85.50; H, 4.80; N, 1.31.

[0318] Synthesis Example 35: Preparation of Compound 701

[0319]

[0320] According to the preparation method of compound 52 in Synthesis Example 8, d-52 and e-52 were replaced with equimolar amounts of d-701 and e-651, respectively, to obtain compound 701 (9.25 g). HPLC analysis showed that the solid purity was ≥99.94%. Mass spectrometry m / z: 832.2647 (theoretical value: 832.2659). Theoretical elemental content (%) C 57 H 36 D3NO2SSi: C, 82.18; H, 5.08; N, 1.68. Measured elemental content (%): C, 82.19; H, 5.06; N, 1.66.

[0321] Synthesis Example 36: Preparation of Compound 703

[0322]

[0323] According to the preparation method of compound 52 in Synthesis Example 8, A-1, d-52, and e-52 were replaced with equimolar amounts of A-703, d-703, and e-703, respectively, to obtain compound 703 (8.88 g). HPLC analysis showed that the solid purity was ≥99.94%. Mass spectrometry m / z: 788.4011 (theoretical value: 788.4021). Theoretical elemental content (%) C 54 D 31 NO2S: C, 82.19; H, 7.91; N, 1.78. Measured elemental content (%): C, 82.17; H, 7.90; N, 1.75.

[0324] Synthesis Example 37: Preparation of Compound 722

[0325]

[0326] According to the preparation method of compound 52 in Synthesis Example 8, A-1, d-52, and e-52 were replaced with equimolar amounts of A-151, d-103, and e-651, respectively, to obtain compound 722 (9.28 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 792.1800 (theoretical value: 792.1807). Theoretical elemental content (%) C 54 H 28 D3NS3: C, 81.79; H, 4.32; N, 1.77. Measured elemental content (%): C, 81.76; H, 4.31; N, 1.79.

[0327] Synthesis Example 39: Preparation of Compound 754

[0328]

[0329] According to the preparation method of compound 1 in Synthesis Example 7, A-1, b-1, and e-1 were replaced with equimolar amounts of A-754, b-754, and e-754, respectively, to obtain compound 754 (20.89 g). HPLC analysis showed that the solid purity was ≥99.94%. Mass spectrometry m / z: 966.2321 (theoretical value: 966.2307). Theoretical elemental content (%) C 68 H 38 DNS3: C, 84.44; H, 4.17; N, 1.45. Measured elemental content (%): C, 84.42; H, 4.16; N, 1.43.

[0330] Synthesis Example 40: Preparation of Compound 756

[0331]

[0332] According to the preparation method of compound 52 in Synthesis Example 8, A-1, d-52, and e-52 were replaced with equimolar amounts of A-756, d-756, and e-651, respectively, to obtain compound 756 (10.90 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 994.2599 (theoretical value: 994.2589). Theoretical elemental content (%) C 70 H 38 D3NS3: C, 84.47; H, 4.46; N, 1.41. Measured elemental content (%): C, 84.44; H, 4.44; N, 1.40.

[0333] Synthetic Example 41: Preparation of Compound 774

[0334]

[0335] According to the preparation method of compound 1 in Synthesis Example 7, A-1 and e-1 were replaced with equimolar amounts of A-774 and e-651, respectively, to obtain compound 774 (21.99 g). HPLC analysis showed that the solid purity was ≥99.95%. Mass spectrometry m / z: 976.3070 (theoretical value: 976.3059). Theoretical elemental content (%) C 68 H 44 D3NS3: C, 83.57; H, 5.16; N, 1.43. Measured elemental content (%): C, 83.54; H, 5.18; N, 1.41.

[0336] Synthesis Example 42: Preparation of Compound 782

[0337]

[0338] According to the preparation method of compound 1 in Synthesis Example 7, A-1 and e-1 were replaced with equimolar amounts of A-782 and e-651, respectively, to obtain compound 782 (20.91 g). HPLC analysis showed that the solid purity was ≥99.94%. Mass spectrometry m / z: 916.2133 (theoretical value: 916.2120). Theoretical elemental content (%) C 64 H 32 D3NS3: C, 83.81; H, 4.18; N, 1.53. Measured elemental content (%): C, 83.80; H, 4.20; N, 1.51.

[0339] Synthesis Example 43: Preparation of Compound 864

[0340]

[0341] According to the preparation method of compound 52 in Synthesis Example 8, A-1, d-52, and e-52 were replaced with equimolar amounts of A-864, d-864, and e-864, respectively, to obtain compound 864 (10.67 g). HPLC analysis showed that the solid purity was ≥99.93%. Mass spectrometry m / z: 911.3151 (theoretical value: 911.3162). Theoretical elemental content (%) C 65 H 37 D3N4S: C, 85.59; H, 4.75; N, 6.14. Measured elemental content (%): C, 85.60; H, 4.72; N, 6.16.

[0342] Synthesis Example 44: Preparation of Compound 893

[0343]

[0344] According to the preparation method of compound 52 in Synthesis Example 8, A-1, b-52, d-52, and e-52 were replaced with equimolar amounts of A-893, b-370, d-436, and e-651, respectively, to obtain compound 893 (10.40 g). HPLC analysis showed that the solid purity was ≥99.96%. Mass spectrometry m / z: 923.2871 (theoretical value: 923.2858). Theoretical elemental content (%) C 67 H 41 NO2S: C, 87.08; H, 4.47; N, 1.52. Measured elemental content (%): C, 87.06; H, 4.44; N, 1.53.

[0345] Synthesis Example 45: Preparation of Compound 906

[0346]

[0347] According to the preparation method of compound 52 in Synthesis Example 8, A-1, b-52, d-52, and e-52 were replaced with equimolar amounts of A-906, b-436, d-906, and e-651, respectively, to obtain compound 906 (11.88 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 1027.3475 (theoretical value: 1027.3484). Theoretical elemental content (%) C 75 H 49 NO2S: C, 87.60; H, 4.80; N, 1.36. Measured elemental content (%): C, 87.62; H, 4.77; N, 1.35.

[0348] Synthesis Example 46: Preparation of Compound 908

[0349]

[0350] Following the preparation method of compound 226 in Synthesis Example 19, A-226, b-226, B1-226, and e-52 were replaced with equimolar amounts of A-908, b-510, B1-908, and e-651 to obtain compound 908 (17.46 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 755.1788 (theoretical value: 755.1775). Theoretical elemental content (%) C 51 H 33 NS3: C, 81.03; H, 4.40; N, 1.85. Measured elemental content (%): C, 81.00; H, 4.43; N, 1.84.

[0351] Synthesis Example 47: Preparation of Compound 929

[0352]

[0353] According to the preparation method of compound 1 in Synthesis Example 7, A-1, b-1, and e-1 were replaced with equimolar amounts of A-929, b-370, and e-651, respectively, to obtain compound 929 (25.27 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 1107.4846 (theoretical value: 1107.4838). Theoretical elemental content (%) C 83 H 65 NS: C, 89.93; H, 5.91; N, 1.26. Measured elemental content (%): C, 89.90; H, 5.93; N, 1.24.

[0354] Synthesis Example 48: Preparation of Compound 949

[0355]

[0356] Following the preparation method of compound 1 in Synthesis Example 7, A-1, b-1, and e-1 were replaced with equimolar amounts of A-315, b-436, and e-651, respectively, to obtain compound 949 (19.67 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 873.3166 (theoretical value: 873.3178). Theoretical elemental content (%) C 63 H 43 N3S: C, 86.57; H, 4.96; N, 4.81. Measured elemental content (%): C, 86.54; H, 4.95; N, 4.83.

[0357] Synthesis Example 49: Preparation of Compound 1014

[0358]

[0359] According to the preparation method of compound 510 in Synthesis Example 28, A-1, B1-510, d-510, and e-510 were replaced with equimolar amounts of A-756, B1-597, d-1014, and e-651, respectively, to obtain compound 1014 (9.67 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 882.3142 (theoretical value: 882.3151). Theoretical elemental content (%) C 63 H 38 D5NS2: C, 85.68; H, 5.48; N, 1.59. Measured elemental content (%): C, 85.66; H, 5.47; N, 1.56.

[0360] Synthesis Example 50: Preparation of Compound 1071

[0361]

[0362] According to the preparation method of compound 52 in Synthesis Example 8, A-1, d-52, and e-52 were replaced with equimolar amounts of A-1071, d-103, and e-1071, respectively, to obtain compound 1071 (17.58 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 770.3001 (theoretical value: 770.3013). Theoretical elemental content (%) C 57 H 34 D3NO2: C, 88.80; H, 5.23; N, 1.82. Measured elemental content (%): C, 88.81; H, 5.22; N, 1.80.

[0363] Synthetic Example 51: Preparation of Compound 1131

[0364]

[0365] According to the preparation method of compound 1 in Synthesis Example 7, A-1 and e-1 were replaced with equimolar amounts of A-151 and e-1131, respectively, to obtain compound 1131 (18.18 g). HPLC analysis showed that the solid purity was ≥99.95%. Mass spectrometry m / z: 818.2881 (theoretical value: 818.2869). Theoretical elemental content (%) C 58 H 38 D3NS2: C, 85.05; H, 5.41; N, 1.71. Measured elemental content (%): C, 85.07; H, 5.40; N, 1.73.

[0366] Synthesis Example 52: Preparation of Compound 1298

[0367]

[0368] According to the preparation method of compound 1 in Synthesis Example 7, A-1, b-1, and e-1 were replaced with equimolar amounts of A-703, b-1298, and e-1298, respectively, to obtain compound 1298 (17.98 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 843.3849 (theoretical value: 843.3860). Theoretical elemental content (%) C 62 H 25 D 14 NO2: C, 88.22; H, 6.33; N, 1.66. Measured elemental content (%): C, 88.21; H, 6.36; N, 1.64.

[0369] Synthesis Example 53: Preparation of Compound 1324

[0370]

[0371] According to the preparation method of compound 52 in Synthesis Example 8, A-1, b-52, d-52, and e-52 were replaced with equimolar amounts of A-1324, b-1298, d-1324, and e-1071, respectively, to obtain compound 1324 (10.61 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 981.4741 (theoretical value: 981.4730). Theoretical elemental content (%) C 73 H 63 NSi: C, 89.25; H, 6.46; N, 1.43. Measured elemental content (%): C, 89.27; H, 6.43; N, 1.41.

[0372] Synthesis Example 54: Preparation of Compound 1332

[0373]

[0374] According to the preparation method of compound 52 in Synthesis Example 8, A-1, b-52, d-52, and e-52 were replaced with equimolar amounts of A-864, b-370, d-1332, and e-1071, respectively, to obtain compound 1332 (10.36 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 985.4388 (theoretical value: 985.4396). Theoretical elemental content (%) C 74 H 55 N3: C, 90.12; H, 5.62; N, 4.26. Measured elemental content (%): C, 90.14; H, 5.61; N, 4.23.

[0375] Synthetic Example 55: Preparation of Compound 1357

[0376]

[0377] Following the preparation method of compound 510 in Synthesis Example 28, B1-510, d-510, and e-510 were replaced with equimolar amounts of B1-1357, d-1357, and e-1071, respectively, to obtain compound 1357 (10.01 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 939.3697 (theoretical value: 939.3688). Theoretical elemental content (%) C 67 H 48 F3NO: C, 85.60; H, 5.15; N, 1.49. Measured elemental content (%): C, 85.63; H, 5.14; N, 1.47.

[0378] Synthesis Example 56: Preparation of Compound 1388

[0379]

[0380] According to the preparation method of compound 510 in Synthesis Example 28, A-1, b-510, B1-510, d-510, and e-510 were replaced with equimolar amounts of A-1388, b-563, B1-1388, d-151, and e-1388, respectively, to obtain compound 1388 (10.42 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 991.4168 (theoretical value: 991.4178). Theoretical elemental content (%) C 77 H 53 N: C, 93.20; H, 5.38; N, 1.41. Measured elemental content (%): C, 93.22; H, 5.37; N, 1.43.

[0381] Synthesis Example 57: Preparation of Compound 1469

[0382]

[0383] Following the preparation method of compound 226 in Synthesis Example 19, A-226, B1-226, and e-52 were replaced with equimolar amounts of A-284, B-122, and e-1469 to obtain compound 1469 (18.83 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 847.3285 (theoretical value: 847.3278). Theoretical elemental content (%) C 62 H 37 D3N2O2: C, 87.81; H, 5.11; N, 3.30. Measured elemental content (%): C, 87.83; H, 5.12; N, 3.27.

[0384] Synthesis Example 58: Preparation of Compound 1526

[0385]

[0386] According to the preparation method of compound 226 in Synthesis Example 19, A-226 and B1-226 were replaced with equimolar amounts of A-1526 and B1-597 to obtain compound 1526 (14.14 g). HPLC analysis showed that the solid purity was ≥99.93%. Mass spectrometry m / z: 654.2489 (theoretical value: 654.2499). Theoretical elemental content (%) C 47 H 26 D3N3O: C, 86.21; H, 4.93; N, 6.42. Measured elemental content (%): C, 86.20; H, 4.96; N, 6.44.

[0387] Synthesis Example 59: Preparation of Compound 1542

[0388]

[0389] Following the preparation method of compound 1 in Synthesis Example 7, e-1 was replaced with an equimolar amount of e-1542 to obtain compound 1542 (18.46 g). HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 878.3598 (theoretical value: 878.3588). Theoretical elemental content (%) C 64 H 42 D3NO3: C, 87.44; H, 5.50; N, 1.59. Measured elemental content (%): C, 87.47; H, 5.52; N, 1.60.

[0390] Synthetic Example 60: Preparation of Compound 1556

[0391]

[0392] Following the preparation method of compound 1 in Synthesis Example 7, e-1 was replaced with an equimolar amount of e-1556 to obtain compound 1556 (17.65 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 816.2897 (theoretical value: 816.2888). Theoretical elemental content (%) C 57 H 36 D3NO3Si: C, 83.79; H, 5.18; N, 1.71. Measured elemental content (%): C, 83.76; H, 5.14; N, 1.73.

[0393] Synthetic Example 61: Preparation of Compound 1589

[0394]

[0395] According to the preparation method of compound 226 in Synthesis Example 19, A-226, b-226, B1-226, and e-52 were replaced with equimolar amounts of A-1, b-563, B1-1589, and e-1589 to obtain compound 1589 (17.81 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 835.2920 (theoretical value: 835.2909). Theoretical elemental content (%) C 61 H 41 NOS: C, 87.63; H, 4.94; N, 1.68. Measured elemental content (%): C, 87.60; H, 4.91; N, 1.70.

[0396] [Device Examples]

[0397] 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.

[0398] [Example 1]

[0399] A patterned ITO (as anode) glass substrate was cut to dimensions of 50 mm × 55 mm × 1 mm, ultrasonically treated with isopropanol for 5 minutes, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes each. The resulting glass substrate was loaded onto a vacuum deposition apparatus. The cleaned glass substrate with transparent electrode lines was mounted on the substrate holder of a vacuum evaporation apparatus. Compound HT-1 and compound HA (mass ratio 3:97) were co-deposited on the side where the transparent electrode lines were formed, forming a hole injection layer with a thickness of 10 nm. Compound HT-1 was then deposited on the hole injection layer to form a first hole transport layer with a thickness of 75 nm. Next, compound HT-2 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 15 nm. Then, compound 1 of the present invention and compound GD-1 were co-deposited on the second hole transport layer to form a light-emitting layer with a thickness of 30 nm. The mass ratio of the present invention compound to compound GD-1 was 75:25. Next, compounds ET-1 and ET-2 were co-deposited on the light-emitting layer to form an electron transport layer with a thickness of 45 nm. The mass ratio of compound ET-1 to compound ET-2 was 50:50. Then, LiQ was deposited on the electron transport layer to form an electron injection layer with a thickness of 1 nm. Finally, metallic Al was deposited on the electron injection electrode to form a metal cathode with a thickness of 40 nm. This forms an organic light-emitting device.

[0400]

[0401] [Examples 2-25]

[0402] Compounds 52, 103, 188, 201, 284, 370, 436, 459, 510, 511, 563, 651, 754, 774, 906, 949, 1014, 1071, 1131, 1298, 1324, 1332, 1357, and 1469 of the present invention were used to replace compound 1 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.

[0403] [Comparative Examples 1-2]

[0404] Organic electroluminescent devices were prepared by replacing compound 1 in Example 1 with compounds GH-1 and GH-2, respectively, as the light-emitting layer materials, except that the preparation method was the same as that in Example 1.

[0405] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of the organic electroluminescent devices obtained by devices 1-25 and comparative examples 1-2 in the embodiments of the present invention are shown in Table 1 below.

[0406]

[0407] 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 GH-1 to GH-2. The carbazole compound of the present invention is a high-performance light-emitting layer material.

[0408] [Example 26]

[0409] A patterned ITO (as anode) glass substrate was cut to dimensions of 50 mm × 55 mm × 1 mm, ultrasonically treated with isopropanol for 5 minutes, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes each. The resulting glass substrate was loaded onto a vacuum deposition apparatus. The cleaned glass substrate with transparent electrode lines was mounted on the substrate holder of a vacuum evaporation apparatus. Compound HT-3 and compound HA (mass ratio 3:97) were co-deposited on the side where the transparent electrode lines were formed, forming a hole injection layer with a thickness of 10 nm. Compound HT-3 was then deposited on the hole injection layer to form a first hole transport layer with a thickness of 75 nm. Next, compound HT-2 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 15 nm. Then, the compound of the present invention, compound GD-2, and compound GD-3 were co-deposited on the second hole transport layer to form a light-emitting layer with a thickness of 35 nm. The mass ratio of compound 52 to compounds GD-2 and GD-3 in this invention is 74:25:1. Next, compounds ET-3 and ET-4 are co-deposited on this light-emitting layer to form an electron transport layer with a thickness of 45 nm. The mass ratio of compounds ET-3 to ET-4 is 50:50. Then, LiQ is deposited on this electron transport layer to form an electron injection layer with a thickness of 1 nm. Finally, metallic Al is deposited on this electron injection electrode to form a metal cathode with a thickness of 40 nm. Thus, an organic light-emitting device is formed.

[0410]

[0411] [Examples 27-45]

[0412] Compounds 110, 151, 162, 315, 472, 489, 540, 563, 701, 722, 782, 893, 929, 1071, 1324, 1332, 1357, 1388, and 1526 of the present invention were used to replace compound 52 in Example 26 as the light-emitting layer material. Otherwise, an organic electroluminescent device was prepared by the same preparation method as in Example 26.

[0413] [Comparative Examples 3-4]

[0414] Compounds GH-3 and GH-4 were used to replace compound 52 in Example 26 as the light-emitting layer material, and the organic electroluminescent device was prepared by the same preparation method as in Example 26.

[0415] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics of the organic electroluminescent devices obtained in embodiments 26-45 and comparative embodiments 3-4 are shown in Table 2 below.

[0416]

[0417] 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 GH-3 to GH-4. The compound of the present invention is a high-performance light-emitting layer material.

[0418] [Example 46]

[0419] A patterned ITO (as anode) glass substrate was cut to dimensions of 50 mm × 55 mm × 1 mm, ultrasonically treated with isopropanol for 5 minutes, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes each. The resulting glass substrate was loaded onto a vacuum deposition apparatus. The cleaned glass substrate with transparent electrode lines was mounted on the substrate holder of the vacuum evaporation apparatus. First, compound HT-3 and compound HA (mass ratio 3:97) were co-deposited on the side where the transparent electrode lines were formed, forming a hole injection layer with a thickness of 10 nm. Compound HT-3 was then deposited on the hole injection layer to form a hole transport layer with a thickness of 75 nm. Next, compound H-1, compound 1 of the present invention (mass ratio 1:1) as the host material of the light-emitting layer and RD-1 doped with 3 wt% were co-deposited on the hole transport layer to form a light-emitting layer with a thickness of 35 nm. Then, compound ET-3 and compound ET-4 were co-deposited on the light-emitting layer to form an electron transport layer with a thickness of 45 nm. The mass ratio of compound ET-3 to compound ET-4 is 50:50. Next, LiQ is deposited on this electron transport layer to form an electron injection layer with a thickness of 1 nm. Then, metallic Al is deposited on this electron injection electrode to form a metal cathode with a thickness of 40 nm. This forms an organic light-emitting device.

[0420]

[0421] [Examples 47-65]

[0422] Compounds 52, 58, 95, 151, 162, 226, 436, 448, 597, 701, 722, 754, 864, 906, 908, 1071, 1332, 1388, and 1589 of the present invention were used to replace compound 1 in Example 46 as the light-emitting layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 46.

[0423] [Comparative Examples 5-6]

[0424] Organic electroluminescent devices were prepared by replacing compound 1 in Example 46 with compounds RH-1 and RH-2, respectively, as the light-emitting layer materials, except that the preparation method was the same as that in Example 46.

[0425] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of the organic electroluminescent devices obtained in embodiments 46-65 and comparative embodiments 5-6 are shown in Table 3 below.

[0426]

[0427] As shown in Table 3, when the carbazole compound described in this 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 RH-1 to RH-2. The compound of this invention is a high-performance light-emitting layer material.

[0428] 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: [Formula I] The rings A, B, and C are either the same as or different from each other, and are independently substituted or unsubstituted C6-C50 aromatic hydrocarbon rings or substituted or unsubstituted C2-C40 aromatic heterocycles. X1 and X2 are each independently a single bond, CR1R2, O or S, but the case where both X1 and X2 are single bonds is excluded; R1 to R2 are each independently selected from any one of 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 group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group, or R1 and R2 can be connected to form a substituted or unsubstituted ring; Ar1 and Ar2 may be identical or different from each other, and are independently selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cyclic groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cyclic groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cyclic groups, substituted or unsubstituted pyridyl groups, and substituted or unsubstituted pyrimidinyl groups; at least one of Ar1 and Ar2 is... X is selected from any one of CR3R4, NR5, O, and S; Each of R3 to R4 is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused cycloyl, or R3 and R4 can be connected to form a substituted or unsubstituted ring; or one of R3 and R4 is a bond connected to L2 or L3; R5 is selected from any one of hydrogen, deuterium, 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 fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused cycloyl group; or R5 is a bond connected to L2 or L3; The R a It is independently selected from any one of 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 a1 is selected from integers from 0 to 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 rings; L1, L2, and L3 are each independently selected from a single bond or any one of the following groups: The R c It is 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 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; The h is selected from integers from 1 to 4; c1 is selected from integers from 0 to 4; c2 is selected from integers from 0 to 6; c3 is selected from integers from 0 to 8; c4 is selected from integers from 0 to 2; when there are two or more R c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings; The n1 may be selected from CH or N, and at most two n1 are N; The n2 may be selected from CH or N, either the same or different. The Rs are either the same as or different from each other, and are independently selected from any one of the following: deuterium, tritium, halogen, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C10-C30 aryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group; The value of m is an integer from 1 to 3.

2. The carbazole compound according to claim 1, characterized in that, The Selected from any one of the following groups: The R a Each is 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 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 R a The definitions of R3 to R5 are the same as those in Equation I; a1 is selected from integers from 0 to 4; a2 is selected from integers from 0 to 3; 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; a'1 is selected from integers from 0 to 8; a'2 is selected from integers from 0 to 6; a'3 is selected from integers from 0 to 10; a'4 is selected from integers from 0 to 14; when there are two or more R... a At that time, two or more R a 'Same or different from each other'.

3. A carbazole compound according to claim 2, characterized in that, The Selected from the following groups: The R a R a R3 to R4 are 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 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 R5 is selected from any one of hydrogen, deuterium, 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; a1 is selected from integers from 0 to 7; a2 is selected from integers from 0 to 9; a3 is selected from integers from 0 to 11; a4 is selected from integers from 0 to 13; a5 is selected from integers from 0 to 3; a6 is selected from integers from 0 to 8; a7 is selected from integers from 0 to 4; a8 is selected from integers from 0 to 10; a9 is selected from integers from 0 to 12; a 10 Integers selected from 0 to 14; 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; a'1 is selected from integers from 0 to 8; a'2 is selected from integers from 0 to 6; a'3 is selected from integers from 0 to 10; a'4 is selected from integers from 0 to 14; a'5 is selected from integers from 0 to 4; a'6 is selected from integers from 0 to 2; when there are two or more R a At that time, two or more R a 'Same or different from each other'.

4. A carbazole compound according to claim 1, characterized in that, Ar1 and Ar2 are not... It is independently selected from the following groups: The R b 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 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; b2 is selected from integers from 0 to 5; 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.

5. A carbazole compound according to claim 4, characterized in that, The Selected from the following groups: The R b R a Each is 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 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 R6 is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, 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; b1 is selected from integers from 0 to 5; b2 is selected from integers from 0 to 7; b3 is selected from integers from 0 to 9; b4 is selected from integers from 0 to 4; b5 is selected from integers from 0 to 3; b6 is selected from integers from 0 to 6; b7 is selected from integers from 0 to 11; 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; a'1 is selected from integers from 0 to 8; a'2 is selected from integers from 0 to 6; a'3 is selected from integers from 0 to 10; a'4 is selected from integers from 0 to 4; a'5 is selected from integers from 0 to 2; when there are two or more R a At that time, two or more R a 'Same or different from each other'.

6. A carbazole compound according to claim 1, characterized in that, L1, L2, and L3 are each independently selected from a single bond or any one of the following groups, or from a combination of two or more of the following groups: The R c R a Each is 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 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; c1 is selected from integers from 0 to 4; c2 is selected from integers from 0 to 6; c3 is selected from integers from 0 to 8; c4 is selected from integers from 0 to 2; c5 is selected from integers from 0 to 3; c6 is selected from integers from 0 to 5; c7 is selected from integers from 0 to 7; when there are two or more R c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings; a'1 is selected from integers from 0 to 8; a'2 is selected from integers from 0 to 6; a'3 is selected from integers from 0 to 10; a'4 is selected from integers from 0 to 4; a'5 is selected from integers from 0 to 2; when there are two or more R a At that time, two or more R a 'Same or different from each other'.

7. A carbazole compound according to claim 1, characterized in that, The Rs may be the same as or different from each other, and are independently selected from any one of deuterium, tritium, substituted or unsubstituted C1 to C6 alkyl groups.

8. A carbazole compound according to claim 1, characterized in that, The compound of formula I is selected from any one of the following structures:

9. 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 8.

10. An organic electroluminescent device according to claim 9, 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 8.

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