An organic compound and use thereof

Abstract

The application relates to an organic compound, and relates to application of the organic compound and an organic electroluminescent device containing the organic compound. The application belongs to the technical field of organic electroluminescence. The organic compound of the application has the structure of formula (1) as follows: ring A, ring B, ring C, ring D and ring E are each independently one of C6-C60 aryl rings and C5-C60 heteroaromatic rings, and at least one of ring A, ring B, ring C and ring D is any one of structures of formula (1-1), formula (1-2) and formula (1-3). The OLED device adopting the organic compound of the application has the advantages of high color purity, high luminous efficiency, good performance and a very long device service life.

Description

Technical Field

[0001] This invention relates to an organic compound, its applications, and organic electroluminescent devices comprising the compound. It belongs to the field of organic electroluminescence technology. Background Technology

[0002] The light-emitting material in organic light-emitting diodes (OLEDs) is crucial. Existing single-state fluorescent materials have good lifetimes and low prices, but low efficiency. Existing triple-state phosphorescent materials have high efficiency, but are expensive, and the lifetime problem of blue light materials has not yet been solved.

[0003] Adachi from Kyushu University in Japan has proposed a new class of organic light-emitting materials: thermally activated delayed fluorescence (TADF) materials. These materials utilize donor-acceptor separation to achieve a smaller singlet-triplet bandgap (ΔE). ST (<0.3eV), allowing triplet excitons to transform into singlet excitons for emission via reverse system crossing (RISC), thus achieving an internal quantum efficiency of 100%. However, traditional TADF molecules have a highly distorted electron donor-acceptor structure, which cannot simultaneously achieve high reverse system crossing rates and high radiative transition rates, limiting further efficiency improvements. Furthermore, because TADF materials emit light in the CT state with a broad spectrum, they cannot meet the color requirements of BT.2020, thus restricting the further application of this type of material in the display field.

[0004] Boron-nitrogen-based multiple resonance (MR) TADF materials possess advantages such as high color purity and high luminous efficiency, attracting widespread attention from the scientific and industrial communities. In recent years, novel MR-TADF-based OLED materials, which combine high efficiency and narrow spectral density, have become a research hotspot in the field of organic electroluminescence. Summary of the Invention

[0005] This invention provides an organic compound that exhibits extremely long stability. The specific technical solution is as follows:

[0006] An organic compound having the structure shown in formula (1):

[0007]

[0008] In this context, rings A, B, C, D, and E are each independently represented as one of the aromatic rings of C6 to C60 and the heteroaromatic rings of C5 to C60, and at least one of rings A, B, C, and D is any structure of formulas (1-1), (1-2), and (1-3). The "*" in formulas (1-1), (1-2), and (1-3) indicates the connection site with formula (1). When ring B or ring C is selected from formulas (1-1), (1-2), or (1-3), three adjacent "*" are randomly selected as the connection point between ring C and the parent nucleus. When ring A or ring D is selected from formulas (1-1), (1-2), or (1-3), two adjacent "*" are randomly selected as the connection point between ring D and the parent nucleus. Any additional unbonded "*" after connection is "H".

[0009] In equation (1), R a R b R c R d R e Each substituent can be independently represented from a single substituent to the maximum permissible number of substituents; the R a R b R c R d R e Each is independently connected to the ring structure it is linked to via a single bond or fused together; the R a R b R c R d R e Two adjacent elements in the middle are either not connected or connected in a loop;

[0010] R a R b R c R d R eEach group is independently selected from one of the following groups: hydrogen, deuterium, halogen, carbonyl, carboxyl, nitro, cyano, amino, or unsubstituted or R'-substituted: C1-C36 chain alkyl, C3-C36 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 alkylsilyl, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, C6-C60 aryloxy, or C5-C60 heteroaryl; The two adjacent R's are either not connected or connected to form a ring; each R' is independently selected from one of the following: deuterium, halogen, cyano, amino, C2-C10 alkenyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 alkylsilyl, C1-C10 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0011] Furthermore, in equation (1), rings A, B, C, and D are each independently the structure shown in equation (a), (b), or (c), or any structure in equations (1-1), (1-2), and (1-3), and at least one of rings A, B, C, and D is any structure in equations (1-1), (1-2), and (1-3); ring E is the structure shown in equation (a);

[0012] In formulas (a), (b) and (c), the double bonds in the dashed lines represent the fusion positions of the group in formula (1);

[0013]

[0014] In equations (a), (b), and (c), Z 1 Z 2 Z 3 Z 4 Z 5 Z 6 Z 7 Z 8 Z 9 Z 10 Z 11 Z 12 Each is independently selected from C, CH, or N;

[0015] In equation (c), Z is selected from O, S, and NR. 1 or CR 2 R 3 ;

[0016] R 1 R 2 R3 It is either not connected to adjacent groups or forms a ring through chemical bonds; R 2 With R 3 They are either not connected or connected in a loop; R 1 R 2 R 3 Each is independently selected from one of the following: unsubstituted or R”-substituted C1-C20 chain alkyl, unsubstituted or R”-substituted C3-C20 cycloalkyl, unsubstituted or R”-substituted C6-C60 aryl, and unsubstituted or R”-substituted C3-C60 heteroaryl;

[0017] "R" is selected from any one of deuterium, halogen, cyano, amino, C2-C20 alkenyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0018] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. The purpose and beneficial effects of the present invention can be better achieved and realized through the following preferred technical solutions.

[0019] Furthermore, in equation (c), Z is selected from O, S, or NR. 1 ;R 1 It is either not connected to adjacent groups or is linked to form a ring through chemical bonds;

[0020] R 1Selected from one of the following groups, either unsubstituted or R”-substituted: phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphylphenyl, terphenyl, trimerphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorenyl, trimerinyl, isotrimerininyl, spirotrimerininyl, spiroisotrimerininyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, Thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, isoindolyl, carbazoleyl, indocarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazoleyl, naphthiazoleyl, phenanthrimidazoleyl, pyridiniumimidazoleyl, pyraziniumimidazoleyl, quinoxalolineimidazolyl, oxazolyl, benzooxazolyl, naphthiazoleyl, anthraquinoxazol 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazathanel, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenthiazinyl, naphridinyl, azacarbazolyl, benzocarbaolinyl, phenanthrolinel, 1,2, 3-Triazolyl, 1,2,4-Triazolyl, Benzotriazolyl, 1,2,3-Oxadiazolyl, 1,2,4-Oxadiazolyl, 1,2,5-Oxadiazolyl, 1,2,3-Thiadiazolyl, 1,2,4-Thiadiazolyl, 1,2,5-Thiadiazolyl, 1,3,4-Thiadiazolyl, 1,3,5-Triazinyl, 1,2,4-Triazinyl, 1,2,3-Triazinyl, Tetrazolyl, 1,2,4,5-Tetraazinyl, 1,2,3,4-Tetraazinyl, 1,2,3,5-Tetraazinyl;

[0021] "R" is selected from one of the following: deuterium, cyano, C1-C6 chain alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0022] Furthermore, in formula (1), rings A, B, C, and D are not selected from formulas (1-1), (1-2), or (1-3), but are each independently selected from one of the aromatic rings of C6 to C30 and the heteroaromatic rings of C5 to C30, and ring E represents an aromatic ring of C6 to C30.

[0023] Preferably, the ring A, ring B, ring C, or ring D not selected from formula (1-1), formula (1-2), or formula (1-3) is each independently selected from phenyl, naphthyl, anthraceneyl, fluorenyl, furanyl, benzofuranyl, dibenzofuranyl, indolyl, benzoindolyl, carbazoleyl, indolocarbazoleyl, benzothiopheneyl, dibenzothiopheneyl, thiopheneyl, benzoanthrayl, phenanthyl, pyrene, pyrene, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzopyreneyl, biphenyl, amphyl, terphenyl, triphenyl, triphenyl, tetraphenyl, diphenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, isobenzothiopheneyl The ring is selected from any one of the following: phenyl, dibenzothiophenyl, pyrroleyl, isoindolyl, carbazoyl, indoxarcarbazoyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indoxolyl, imidazoyl, benzimidazolyl, naphthimidazolyl, phenanthridinemidazolyl, pyridiniumimidazoyl, pyraziniumimidazoyl, quinoxoliniumimidazoyl, oxazolyl, benzooxazolyl, naphthimidazolyl, anthraquinoxazolyl, phenanthridinemidazolyl, 1,2-thiazoyl, 1,3-thiazoyl, benzothiazoyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, and quinoxolinyl; ring E is selected from a benzene ring.

[0024] More preferably, the ring A, ring B, ring C, or ring D not selected from formulas (1-1), (1-2), and (1-3) is each independently selected from one of phenyl, naphthyl, anthraceneyl, fluorenyl, furanyl, benzofuranyl, dibenzofuranyl, indolyl, benzoindolyl, carbazoyl, indolocarbazoyl, benzothiopheneyl, dibenzothiopheneyl, thiopheneyl, phenanthryl, pyridinyl, quinolinyl, isoquinolinyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, and quinoxalinyl.

[0025] More preferably, the rings A, B, C, or D not selected from formulas (1-1), (1-2), and (1-3) are each independently selected from one of phenyl, naphthyl, anthraceneyl, fluorenyl, furanyl, benzofuranyl, dibenzofuranyl, indolyl, benzoindolyl, carbazoyl, indolocarbazoyl, benzothiophenyl, dibenzothiophenyl, and thiophenyl; ring E is selected from a benzene ring.

[0026] Furthermore, in equation (1), ring A, ring B, ring C, and ring D are each independently represented as one of an aromatic ring of C6 to C30 or a heteroaromatic ring of C5 to C30, and at least one of ring A, ring B, ring C, and ring D is any structure in equation (1-1), equation (1-2), or equation (1-3).

[0027] Preferably, only one of rings A, B, C, and D has any structure from equations (1-1), (1-2), and (1-3);

[0028] Alternatively, preferably, two of rings A, B, C, and D are any of the structures in equations (1-1), (1-2), and (1-3);

[0029] More preferably, only one of rings A and B has any one of the structures in equations (1-1), (1-2), and (1-3), and only one of rings C and D has any one of the structures in equations (1-1), (1-2), and (1-3);

[0030] More preferably, ring A is any one of the structures in formula (1-1), formula (1-2), and formula (1-3), while ring D is any one of the structures in formula (1-1), formula (1-2), and formula (1-3); or, ring B is any one of the structures in formula (1-1), formula (1-2), and formula (1-3), while ring C is any one of the structures in formula (1-1), formula (1-2), and formula (1-3).

[0031] The organic compounds of the present invention preferably have the structure shown in formula (2-1):

[0032]

[0033] Among them, R a R b R c R d R e The definitions are the same as those in equation (1); at least one of rings A, B, C, and D is any structure in equations (1-1), (1-2), and (1-3), and rings A, B, C, or D not selected from equations (1-1), (1-2), and (1-3) are each independently the structure shown in equation (a), (b), or (c); the structure and definition scope of equations (a), (b), and (c) are the same as above;

[0034] Preferably, only one of rings A, B, C, and D is any structure of equation (1-1), (1-2), or (1-3), and rings A, B, C, or D not selected from equations (1-1), (1-2), and (1-3) are each independently the structure shown in equation (a), (b), or (c).

[0035] Alternatively, preferably, only two of rings A, B, C, and D are structures of any one of equations (1-1), (1-2), and (1-3), and the remaining rings A, B, C, or D not selected from equations (1-1), (1-2), and (1-3) are each independently structures shown in equation (a), (b), or (c).

[0036] More preferably, only one of rings A and B has any one of the structures in equations (1-1), (1-2), and (1-3), while only one of rings C and D has any one of the structures in equations (1-1), (1-2), and (1-3), and the structures not selected from equations (1-1), (1-2), and (1-3) are each independently the structures shown in equation (a), (b), or (c).

[0037] More preferably, ring A is any structure of formula (1-1), formula (1-2), or formula (1-3), and ring D is any structure of formula (1-1), formula (1-2), or formula (1-3), except for those not selected from formula (1-1), formula (1-2), or formula (1-3) which are independently represented by formula (a), formula (b), or formula (c); or, ring B is any structure of formula (1-1), formula (1-2), or formula (1-3), and ring C is any structure of formula (1-1), formula (1-2), or formula (1-3), except for those not selected from formula (1-1), formula (1-2), or formula (1-3) which are independently represented by formula (a), formula (b), or formula (c).

[0038] More preferably, in formula (2-1), rings A, B, C, and D are not selected from formulas (1-1), (1-2), and (1-3), but are each independently selected from one of the following: phenyl, naphthyl, anthraceneyl, fluorenyl, furanyl, benzofuranyl, dibenzofuranyl, indolyl, benzoindolyl, carbazoyl, indolocarbazoyl, benzothiopheneyl, dibenzothiopheneyl, thiopheneyl, phenanthryl, pyridinyl, quinolinyl, isoquinolinyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, and quinoxalinyl.

[0039] Most preferably, in formula (2-1), rings A, B, C, and D are not selected from formulas (1-1), (1-2), and (1-3), but are each independently selected from one of phenyl, naphthyl, anthraceneyl, fluorenyl, furanyl, benzofuranyl, dibenzofuranyl, indolyl, benzoindolyl, carbazoyl, indolocarbazoyl, benzothiophenyl, dibenzothiophenyl, and thiophenyl.

[0040] Furthermore, in equations (1) and (2-1), the R... a R b R c R d R e Each group is independently selected from hydrogen, deuterium, halogen, cyano, or unsubstituted or R'-substituted groups of the following: C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C20 arylamino, C3-C20 heteroarylamino, C6-C30 aryl, C6-C30 aryloxy, and C5-C30 heteroaryl.

[0041] R' is selected from one of the following: deuterium, halogen, cyano, amino, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 alkylsilyl, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0042] Preferably, the R a R b R c R d R eEach of the following substituents is independently selected from hydrogen, deuterium, cyano, halogen, or a combination of one or two of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, pyryl, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphyl, terphenyl, triphenyl, tetraphenyl, Fluorenyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, trimerinyl, isotrimericininyl, spirotrimericininyl, spiroisotrimericininyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, isoindoleyl, carbazoleyl, indocarbazoleyl, pyridinyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazoyl, benzimidazoleyl, naphthizimidazoleyl, phenanthrenezimidazoleyl, pyridinium imidazoyl, pyrazine Imidazolyl, quinoxaloylimidazolyl, oxazolyl, benzoxoxazolyl, naphthoxazolyl, anthraxoxazolyl, phenanthoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxaloyl, 1,5-diazaanthrayl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl Benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetraazinyl, 1,2,3,4-tetraazinyl, 1,2,3,5-tetraazinyl, purinyl, pteridyl, indazyl, benzothiadiazolyl, 9,9-dimethylacridyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl or methoxy;

[0043] More preferably, the R a R b R c R d R eEach of the following groups is independently selected from hydrogen, deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-methylbutyl, trifluoromethyl, pentafluoroethyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, furanyl, benzo[a]furanyl, isobenzo[a]furanyl, dibenzo[a]furanyl, thienyl, benzo[a]thienyl, isobenzo[a]thienyl, dibenzo[a]thienyl, pyrroleyl, isoindoleyl, carbazoleyl, indoxocarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, pyrazolyl, indazoleyl, imidazolyl. Pyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetraazinyl, inazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, or methoxy.

[0044] In this invention, the "substituted or unsubstituted" group can replace one substituent or multiple substituents. When there are multiple substituents, they can be selected from different substituents. In this invention, when the same expression is used, they all have the same meaning, and the selection range of substituents is as shown above and will not be repeated one by one.

[0045] In this specification, the expression Ca to Cb represents that the group has a to b carbon atoms. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms of the substituents.

[0046] In this specification, the ring structure indicated by "—" represents any position on the ring structure where bonding can occur; the dashed double bond represents the position where the group is fused in the parent nucleus.

[0047] In this specification, "each independently" means that when there are multiple subjects, they may be the same or different from each other.

[0048] In this invention, the description of chemical elements, unless otherwise specified, usually includes the concept of their isotopes. For example, the description of "hydrogen (H)" includes the concept of its isotopes 1H (protium or H) and 2H (deuterium or D); carbon (C) includes 12C, 13C, etc., which will not be elaborated further.

[0049] In this invention, heteroatoms generally refer to atoms or groups of atoms selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0050] Examples of halogens in this specification include fluorine, chlorine, bromine, and iodine.

[0051] In this invention, unless otherwise specified, aryl and heteroaryl groups include both monocyclic and fused-ring groups.

[0052] In this invention, the term "single bond connection or fused connection" generally refers to the substituent group being directly connected to the parent structure via a single bond, or the substituent group being fused to the parent structure, thereby forming a fused-ring aromatic hydrocarbon structure with multiple aromatic rings sharing the same edge. The aromatic rings here include six-membered aromatic rings such as benzene rings, as well as five-membered and six-membered heteroaromatic rings containing atoms such as N, O, or S.

[0053] In this invention, C6-C60 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, or C58, etc.

[0054] C3-C60 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, or C58, etc.

[0055] C1-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0056] C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0057] C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0058] C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0059] C2-C10 can all be C2, C3, C4, C5, C6, C7, C8, C9 or C10.

[0060] In this invention, the substituted or unsubstituted C6-C60 aryl (or C6-C50 aryl) includes monocyclic aryl and fused-ring aryl, preferably C6-C30 aryl, and more preferably C6-C20 aryl. A monocyclic aryl refers to a molecule containing at least one phenyl group. When a molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, exemplarily such as phenyl, biphenyl, and terphenyl. Specifically, the biphenyl includes 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, meta-terphenyl-4-yl, meta-terphenyl-3-yl, and meta-terphenyl-2-yl. A fused-ring aryl refers to a molecule containing at least two aromatic rings, where the aromatic rings are not independent of each other but share two adjacent carbon atoms fused together. Examples include: naphthyl, anthracene, phenanthrene, indene, fluorenyl, fluoranthyl, triphenylene, pyrene, perylene, etc. Naphthyl, 2-naphthyl, and their derivative groups, etc. The naphthyl includes 1-naphthyl or 2-naphthyl; the anthraceneyl is selected from 1-anthrayl, 2-anthrayl, and 9-anthrayl; the fluorenyl is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrene is selected from 1-pyrene, 2-pyrene, and 4-pyrene; the 2-tetraphenyl is selected from 1-2 ... The fluorene derivative group is selected from 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, 9,9'-spirodifluorenyl, and benzo[a]fluorenyl.

[0061] The C3-C60 heteroaryl (or C6-C50 heteroaryl) mentioned in this invention includes monocyclic heteroaryl and fused-ring heteroaryl, preferably C3-C30 heteroaryl, more preferably C4-C20 heteroaryl, and even more preferably C5-C12 heteroaryl. A monocyclic heteroaryl refers to a molecule containing at least one heteroaryl group. When a molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and connected by a single bond. Examples of monocyclic heteroaryl groups include furanyl, thiophene, pyrrole, and pyridinyl. A fused-ring heteroaryl refers to a molecule containing at least one aromatic heterocycle and an aromatic ring (aromatic heterocycle or aromatic ring), and the two are not independent of each other but share two adjacent atoms fused together. Examples of fused-ring heteroaryl groups include: benzofuranyl, benzothiophenyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazoyl, acridineyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazoyl, azircarbazoyl, phenothiazinyl, phenothiazinyl, 9-phenylcarbazoyl, 9-naphthylcarbazoyl, dibenzocarbazoyl, indolocarbazoyl, etc.

[0062] The aryloxy or heteroaryloxy groups in this invention can be exemplified by the monovalent groups formed by the above-mentioned aryl or heteroaryl groups and oxygen.

[0063] In this invention, arylamino represents a group formed by replacing the hydrogen on an amino group with one or two aryl groups, wherein the linking site of the arylamino can be linked to the aryl group in the arylamino or to the N group in the arylamino, and the exemplary number of carbons and specific groups of the aryl group in the arylamino are the same as described above.

[0064] Examples of C6-C30 arylamino groups mentioned in this invention include phenylamino, methylphenylamino, naphthylamino, anthraceneylamino, phenanthreneamino, and biphenylamino.

[0065] Examples of C3-C30 heteroaryl amino groups mentioned in this invention include pyridinyl amino, pyrimidinyl amino, and dibenzofuranyl amino.

[0066] Unless otherwise specified, the chain alkyl groups mentioned in this invention include straight-chain alkyl groups and branched-chain alkyl groups. Specifically, substituted or unsubstituted C1-C30 chain alkyl groups are preferred, substituted or unsubstituted C1-C16 chain alkyl groups are more preferably substituted or unsubstituted C1-C10 chain alkyl groups. Examples of substituted or unsubstituted C1-C10 chain alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, 2-ethylhexyl, etc.

[0067] In this invention, the cycloalkyl group includes monocycloalkyl and polycycloalkyl; wherein, monocycloalkyl refers to an alkyl group containing a single ring structure; polycycloalkyl refers to a structure composed of two or more cycloalkyl groups sharing one or more carbon atoms on a ring; examples of C3-C20 cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0068] In this specification, the substituted or unsubstituted C1-C20 alkoxy group is preferably a substituted or unsubstituted C1-C10 alkoxy group. Examples of C1-C20 alkoxy groups include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentooxy, isopentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoxy, undecoxy, dodecoxy, etc., among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentoxy, and more preferably methoxy.

[0069] In this specification, the substituted or unsubstituted C1-C20 silane and the substituted or unsubstituted C1-C10 silane are examples of silanes substituted with groups listed in the above-mentioned C1-C10 chain alkyl groups, specifically including: methylsilane, dimethylsilane, trimethylsilane, ethylsilane, diethylsilane, triethylsilane, tert-butyldimethylsilane, tert-butyldiphenylsilane, etc.

[0070] In this specification, the C2-C20 alkenyl group, preferably C2-C10 alkenyl group, is a hydrocarbon group containing at least one C=C double bond, and includes, but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0071] It should be noted that while the possible effects of each group / feature have been described separately for ease of explanation in this application, this does not mean that these groups / features act in isolation. In fact, the reason for achieving good performance is essentially the optimized combination of the entire molecule, the result of the synergistic effect between various groups, rather than the effect of a single group.

[0072] Furthermore, the general formula compounds of the present invention can preferably include the following specific structural compounds A1 to A218, which are merely representative examples:

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084] In the compounds of this invention, at least one of rings A, B, C, and D is any structure of formulas (1-1), (1-2), and (1-3). In the structures of formulas (1-1), (1-2), and (1-3), the benzene rings connected by the carbazole N atom are connected by a screw-like locking mechanism, which connects the two benzene rings, eliminates the original repulsion between hydrogen atoms, and prevents the benzene rings connected by the carbazole N atom from rotating freely. This significantly enhances the rigidity of the molecule, further reduces the half-width at half-maximum (FWHM) (≤25nm), improves color purity, and significantly improves the efficiency and lifetime of the corresponding light-emitting devices.

[0085] This invention has verified through extensive experiments that the electroluminescence spectrum of OLED devices prepared using the compounds of this invention has a narrow half-width (WHM) (≤25nm), which greatly enriches the framework system of multiple resonance narrow-spectrum materials, while greatly simplifying the synthesis process and improving the reaction yield. The corresponding electroluminescent devices have high luminous efficiency and extremely long lifespan, which can meet the requirements of current panel manufacturers for high-performance materials and show good application prospects in industrialization.

[0086] A second objective of this invention is to provide an application of the compound described in the first objective, specifically its application as a functional material in organic electronic devices, such as organic electroluminescent devices, optical sensors, solar cells, organic thin-film transistors, or organic field-effect transistors.

[0087] Furthermore, the compound is used as a light-emitting layer material in organic electroluminescent devices, specifically as a light-emitting material in the light-emitting layer.

[0088] A third objective of this invention is to provide an organic electroluminescent device. Specifically, an embodiment of this invention provides an organic electroluminescent device comprising a substrate, and an anode layer, a plurality of light-emitting functional layers, and a cathode layer sequentially formed on the substrate; the light-emitting functional layers include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is located between the hole transport layer and the electron transport layer; preferably, the light-emitting layer contains a compound of the general formula of this invention shown in any of the above general formulas, or the light-emitting layer contains at least one of the specific compounds A1 to A218 mentioned above.

[0089] The fourth objective of this invention is to provide a display device, including the aforementioned organic electroluminescent device. Detailed Implementation

[0090] The specific preparation methods of the above-mentioned new compounds of the present invention will be described in detail below using several synthetic examples, but the preparation methods of the present invention are not limited to these synthetic examples.

[0091] All the chemical reagents used in this invention, such as petroleum ether, tert-butylbenzene, sodium sulfate, toluene, dichloromethane, cesium carbonate, sodium hydride, boron tribromide, tetrahydrofuran, N,N-dimethylformamide, n-butyllithium, and reaction intermediates, were purchased from Shanghai Titan Technology Co., Ltd. and Xilong Chemical Co., Ltd. The mass spectrometer used to determine the following compounds was a ZAB-HS type mass spectrometer (manufactured by Micromass, UK).

[0092] The synthetic method of the compounds of this invention is briefly described below. First, carbazole and indolecarbazole derivatives are reacted with polyhalogenated benzenes using a nucleophilic substitution reaction to obtain a chlorinated intermediate. Then, after lithium halide exchange with tert-butyllithium, electrophilic boronization with boron tribromide is carried out to obtain the target compound.

[0093] Synthesis Examples

[0094] Example 1: Synthesis of Compound A1

[0095]

[0096] In a dry 100 mL double-necked round-bottom flask, add polyhalogenated benzene (3 mmol), carbazole and indolecarbazole derivatives (3 mmol each), Cs₂CO₃ (15 mmol), and DMF (100 mL). Under a nitrogen atmosphere, heat to 150 °C and reflux for 24 h. After the reaction is complete, allow to cool naturally to room temperature, remove the solvent by rotary evaporation, and separate the crude product by silica gel column chromatography using petroleum ether:dichloromethane = 15:1 as the developing solvent to obtain intermediate compound A1-1.

[0097] Compound A1-1 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing solvent to obtain the target compound A1.

[0098] Example 2 Synthesis of Compound A7

[0099]

[0100] In a 100 mL dry double-necked round-bottom flask, add polyhalogenated benzene (3 mmol), indolecarbazole derivatives (3 mmol each), Cs₂CO₃ (15 mmol), and DMF (100 mL). Under a nitrogen atmosphere, heat to 150 °C and reflux for 24 h. After the reaction is complete, allow to cool naturally to room temperature. Remove the solvent by rotary evaporation. Separate the crude product by silica gel column chromatography using petroleum ether:dichloromethane = 10:1 as the developing solvent to obtain intermediate compound A7-1.

[0101] Compound A7-1 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 15:1 as the developing solvent to obtain the target compound A7.

[0102] Example 3 Synthesis of compound A17

[0103]

[0104] In a 100 mL dry double-necked round-bottom flask, add polyhalogenated benzene (3 mmol), indolecarbazole derivatives (3 mmol each), Cs₂CO₃ (15 mmol), and DMF (100 mL). Under a nitrogen atmosphere, heat to 150 °C and reflux for 24 h. After the reaction is complete, allow to cool naturally to room temperature. Remove the solvent by rotary evaporation. Separate the crude product by silica gel column chromatography using petroleum ether:dichloromethane = 15:1 as the developing solvent to obtain intermediate compound A17-1.

[0105] Compound A17-1 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing solvent to obtain the target compound A17.

[0106] Example 4 Synthesis of compound A27

[0107]

[0108] In a 100 mL dry double-necked round-bottom flask, add polyhalogenated benzene (3 mmol), indolecarbazole derivatives (3 mmol each), Cs₂CO₃ (15 mmol), and DMF (100 mL). Under a nitrogen atmosphere, heat to 150 °C and reflux for 24 h. After the reaction is complete, allow to cool naturally to room temperature, remove the solvent by rotary evaporation, and separate the crude product by silica gel column chromatography using petroleum ether:dichloromethane = 5:1 as the developing solvent to obtain intermediate compound A27-1.

[0109] Compound A27-1 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 5:1 as the developing solvent to obtain the target compound A27.

[0110] Example 5 Synthesis of compound A44

[0111]

[0112] In a 100 mL dry double-necked round-bottom flask, add polyhalogenated benzene (3 mmol), indolecarbazole derivatives (3 mmol each), Cs₂CO₃ (15 mmol), and DMF (100 mL). Under a nitrogen atmosphere, heat to 150 °C and reflux for 24 h. After the reaction is complete, allow to cool naturally to room temperature, remove the solvent by rotary evaporation, and separate the crude product by silica gel column chromatography using petroleum ether:dichloromethane = 5:1 as the developing solvent to obtain intermediate compound A44-1.

[0113] Compound A44-1 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing solvent to obtain the target compound A44.

[0114] Example 6 Synthesis of compound A128

[0115]

[0116] In a 100 mL dry double-necked round-bottom flask, polyhalogenated benzene (3 mmol), indolecarbazole derivative (8 mmol), Cs₂CO₃ (15 mmol), and DMF (100 mL) were added. The mixture was heated to 150 °C under a nitrogen atmosphere and refluxed for 24 h. After the reaction was complete, it was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was separated by silica gel column chromatography using petroleum ether:dichloromethane = 15:1 as the developing solvent to obtain the intermediate compound A128-1.

[0117] Compound A128-1 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 10:1 as the developing solvent to obtain the target compound A128.

[0118] Example 7 Synthesis of compound A199

[0119]

[0120] In a 100 mL dry double-necked round-bottom flask, add polyhalogenated benzene (3 mmol), indolecarbazole derivatives (3 mmol each), Cs₂CO₃ (15 mmol), and DMF (100 mL). Under a nitrogen atmosphere, heat to 150 °C and reflux for 24 h. After the reaction is complete, allow to cool naturally to room temperature, remove the solvent by rotary evaporation, and separate the crude product by silica gel column chromatography using petroleum ether:dichloromethane = 10:1 as the developing solvent to obtain intermediate compound A199-1.

[0121] Compound A199-1 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 15:1 as the developing solvent to obtain the target compound A199.

[0122] Example 8 Synthesis of compound A218

[0123]

[0124] In a 100 mL dry double-necked round-bottom flask, polyhalogenated benzene (3 mmol), indolecarbazole derivative (8 mmol), Cs₂CO₃ (15 mmol), and DMF (100 mL) were added. The mixture was heated to 150 °C under a nitrogen atmosphere and refluxed for 24 h. After the reaction was complete, it was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The crude product was separated by silica gel column chromatography using petroleum ether:dichloromethane (10:1) as the developing solvent to obtain the intermediate compound A218-1.

[0125] Compound A218-1 (1 mmol) was dissolved in 20 mL of tert-butylbenzene in a sealed tube. After cooling to -78 °C, a pentane solution of tert-butyllithium (1 M, 2.5 mL) was added, followed by heating to 30 °C and reacting for 1 hour. The mixture was then cooled again to -78 °C, and boron tribromide (3 mmol) was slowly added, followed by heating to 30 °C and stirring for another hour. After cooling to 0 °C, diisopropylethylamine (5 mmol) was added, followed by heating to 160 °C and reacting for 12 hours. The solvent was removed under vacuum, and the mixture was passed through a silica gel column using petroleum ether:dichloromethane = 5:1 as the developing solvent to obtain the target compound A218.

[0126] The synthesis methods of the following synthetic examples 9-26 are similar to those of examples 1-8 above. The only difference is that the polyhalogenated benzene, carbazole and indolecarbazole derivatives in the first step are replaced with the corresponding polyhalogenated benzene, carbazole and indolecarbazole derivatives.

[0127]

[0128]

[0129] The specific experimental results of synthesis examples 1-26 are as follows:

[0130]

[0131]

[0132] Note: The HPLC instrument used was a Shimadzu Nexera LC-40 series liquid chromatograph. The MALDI-TOF-MS instrument used was a Shimadzu AXIMA Performance MALDI-TOF. The elemental analysis instrument used was a Thermo Fisher FlashSmart elemental analyzer.

[0133] Device Examples

[0134] The technical effects and advantages of the present invention will be demonstrated and verified by specifically applying the compounds of the present invention to organic electroluminescent devices and testing their actual performance.

[0135] An organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer located between the two electrodes. This organic material layer can be further divided into multiple regions; for example, it may include a hole transport region, a light-emitting layer, and an electron transport region.

[0136] The anode material can be any combination of transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), and zinc oxide (ZnO). The cathode material can be any combination of metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag).

[0137] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0138] The material for the hole transport region can be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene oxide, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, etc.

[0139] The emissive layer includes luminescent dyes (i.e., dopants) that can emit different wavelengths of light, and may also include a host material. The emissive layer can be a monochromatic emissive layer emitting a single color such as red, green, or blue. Multiple monochromatic emissive layers of different colors can be arranged in a planar pattern according to pixel design, or they can be stacked together to form a colored emissive layer. When different colored emissive layers are stacked together, they can be separated from each other or connected to each other. The emissive layer can also be a single colored emissive layer that can simultaneously emit different colors such as red, green, and blue.

[0140] The electron transport region can be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region can also be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0141] Specifically, the method for fabricating the organic electroluminescent device of the present invention includes the following steps:

[0142] 1. The glass plate coated with the anodic material is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixture of acetone and ethanol, baked in a clean environment until all moisture is removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0143] 2. Place the glass plate with the anode in a vacuum chamber and evacuate it to 1×10-5~9×10-3 Pa. Vacuum deposit hole injection material on the anode film to form a hole injection layer. The deposition rate is 0.1-0.5 nm / s.

[0144] 3. A hole transport layer is formed by vacuum evaporation of a hole transport material on top of the hole injection layer, with an evaporation rate of 0.1-0.5 nm / s.

[0145] 4. An electron blocking layer is vacuum-deposited on top of the hole transport layer at a deposition rate of 0.1-0.5 nm / s;

[0146] 5. An organic light-emitting layer of the device is vacuum-deposited on top of the electron blocking layer. The organic light-emitting layer material includes a host material and a light-emitting dye. By using a multi-source co-evaporation method, the evaporation rate of the host material, the evaporation rate of the sensitizer material, and the evaporation rate of the dye are adjusted to make the dye reach a preset doping ratio.

[0147] 6. A hole blocking layer is vacuum-deposited on the organic light-emitting layer at a deposition rate of 0.1-0.5 nm / s;

[0148] 7. An electron transport layer is formed by vacuum evaporating the electron transport material of the device on top of the hole blocking layer, with an evaporation rate of 0.1-0.5 nm / s;

[0149] 8. A LiF layer is vacuum-deposited at 0.1-0.5 nm / s as the electron injection layer on the electron transport layer, and an Al layer is vacuum-deposited at 0.1-0.5 nm / s as the cathode of the device.

[0150] This invention also provides a display device, which includes the organic electroluminescent device as described above. Specifically, the display device can be an OLED display or other display device, as well as any product or component with display function, such as a television, digital camera, mobile phone, or tablet computer, that includes the display device. The advantages of this display device over the prior art are the same as those of the organic electroluminescent device described above, and will not be repeated here.

[0151] The organic electroluminescent device of the present invention will be further described below through specific embodiments.

[0152] Device Example 1

[0153] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0154] ITO / HI(5nm) / HT(25nm) / EBL(12nm) / Host:3wt%A1(28nm) / HBL(6nm) / ET(25nm) / LiF(0.7nm) / Al(150nm)

[0155] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this example); the hole transport layer material is HT, with a total thickness of 5-500 nm (25 nm in this example); the electron blocking layer material is EBL, with a total thickness of 0-30 nm (12 nm in this example); the host is the main material of the wide bandgap organic light-emitting layer, Al is a dye with a doping concentration of 3 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (28 nm in this example); the hole blocking layer material is HBL, with a total thickness of 0-30 nm (6 nm in this example); the electron transport layer material is ET, with a thickness of 5-300 nm (25 nm in this example); and the electron injection layer and cathode materials are LiF (0.7 nm) and metallic aluminum (150 nm).

[0156] Device Example 2

[0157] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0158] ITO / HI(5nm) / HT(25nm) / EBL(12nm) / Host:40wt%TD:3wt%A1(28nm) / HBL(6nm) / ET(25nm) / LiF(0.7nm) / Al(150nm)

[0159] In this embodiment, the anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this example); the hole transport layer material is HT, with a total thickness of 5-500 nm (25 nm in this example); the electron blocking layer material is EBL, with a total thickness of 0-30 nm (12 nm in this example); the host is the main material of the wide bandgap organic light-emitting layer, TD is a TADF type host with a doping concentration of 40 wt%, Al is a dye with a doping concentration of 3 wt%, and the thickness of the organic light-emitting layer is generally 1-200 nm (28 nm in this example); the hole blocking layer material is HBL, with a total thickness of 0-30 nm (6 nm in this example); the electron transport layer material is ET, with a thickness of 5-300 nm (25 nm in this example); and the electron injection layer and cathode materials are LiF (0.7 nm) and aluminum (150 nm).

[0160] Device Examples 1 and 2 are respectively non-sensitized and sensitized devices for dye A1.

[0161] Examples 3-52 of this invention are the same as those in Device Examples 1 and 2, except that the dye is replaced with the compound of this invention. They are also divided into two groups: unsensitized and sensitized devices. Comparative Examples 1-6 are parallel comparative devices prepared using existing compounds P1, P2, and P3 according to the same preparation method as the compounds of this invention. The structural schemes of all prepared devices are shown in Table 1 below:

[0162] Table 1:

[0163]

[0164]

[0165]

[0166] The anode material is ITO; the hole injection layer material is HI, with a total thickness of 5-30 nm (5 nm in this embodiment); the hole transport layer material is HT, with a total thickness of 5-500 nm (25 nm in this embodiment); the electron blocking layer material is EBL, with a total thickness of 0-30 nm (12 nm in this embodiment); the host organic light-emitting layer has a wide bandgap substrate material, TD is a TADF type substrate, and the thickness of the organic light-emitting layer is 1-200 nm (28 nm in this embodiment); the hole blocking layer material is HBL, with a total thickness of 0-30 nm (6 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (25 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.7 nm) and aluminum (150 nm).

[0167] The structural formulas of the various organic materials used in the above embodiments are as follows:

[0168]

[0169]

[0170] The performance of the devices prepared in Examples 1-52 and Comparative Examples 1-6 of this invention is shown in Table 2 below:

[0171] Table 2:

[0172]

[0173]

[0174]

[0175] Note: In Table 2, the half-width at half-maximum (WHM) is the half-width of the electroluminescence spectrum in the device. It is the peak width at half the peak height, that is, the distance between the two points where the straight line parallel to the bottom of the peak passes through the midpoint of the peak height and intersects the two sides of the peak.

[0176] The photoelectric properties of OLED devices, such as current density and external quantum efficiency, as well as their photochromic properties, such as electroluminescence spectrum, were obtained using a combination of a Hamamatsu C9920-02G quantum efficiency meter and a Keithley 2400 semiconductor analyzer. Device lifetime (LT85@20mA / cm) 2 This represents the time taken for the device brightness to decrease to 85% of its initial brightness, where the initial brightness is a current density of 20 mA / cm². 2 The corresponding brightness was obtained by testing using the OLED aging life test system of Shanghai University.

[0177] In Table 2, LT85@20mA / cm 2 The relative value of / h is the result obtained by comparing with Comparative Example 1.

[0178] In the compounds of this invention, at least one of rings A, B, C, and D is any structure of formulas (1-1), (1-2), and (1-3). In the structures of formulas (1-1), (1-2), and (1-3), the benzene rings connected by the carbazole N atom are connected by a screw-like locking mechanism, which connects the two benzene rings, eliminates the original repulsion between hydrogen atoms, and prevents the benzene rings connected by the carbazole N atom from rotating freely. This significantly enhances the rigidity of the molecule, further reduces the half-width at half-maximum (FWHM) (≤25nm), improves color purity, and significantly improves the efficiency and lifetime of the corresponding light-emitting devices.

[0179] Compared to Comparative Examples 1-6, Examples 1-52, with other materials remaining the same in the organic electroluminescent device structure, exhibit higher efficiency, narrower half-width at half-maximum (WHM), and longer lifetime. The electroluminescence spectra of OLED devices prepared using the compounds of this invention have narrow WHMs (≤25 nm), thus greatly enriching the framework system of multiple resonance narrow-spectrum materials. The corresponding electroluminescent devices possess high luminous efficiency and extremely long lifetime, meeting the current requirements of panel manufacturers for high-performance materials and demonstrating promising application prospects in industrialization.

[0180] The experimental data above show that the novel MR-TADF material provided by this invention, when used in organic electroluminescent devices, achieves excellent performance in terms of high color purity and high luminous efficiency, while also exhibiting an extremely long device lifetime. Therefore, this type of novel compound is a high-performance organic light-emitting functional material with promising prospects for commercial application.

[0181] Although the invention has been described with reference to embodiments, it is not limited to the above embodiments. It should be understood that various modifications and improvements can be made by those skilled in the art under the guidance of the inventive concept, and the appended claims summarize the scope of the invention. Obviously, the above embodiments are merely examples for clear illustration and are not intended to limit the implementation. For those skilled in the art, other variations or modifications can be made based on the above description. It is neither necessary nor possible to exhaustively describe all embodiments here. However, obvious variations or modifications derived therefrom are still within the protection scope of this invention.

Claims

1. An organic compound having the structure shown in formula (1), wherein, Rings A, B, C, D, and E are each independently represented as one of an aromatic ring of C6 to C60 or a heteroaromatic ring of C5 to C60, and at least one of rings A, B, C, and D is any structure of formulas (1-1), (1-2), and (1-3): In equations (1-1), (1-2), and (1-3), "*" indicates the connection point with equation (1); In equation (1), R a R b R c R d R e Each substituent can be independently represented from a single substituent to the maximum permissible number of substituents; the R a R b R c R d R e Each is independently connected to the ring structure it is linked to via a single bond or fused together; the R a R b R c R d R e Two adjacent elements in the middle are either not connected or connected in a loop; R a R b R c R d R e Each group is independently selected from one of the following groups: hydrogen, deuterium, halogen, carbonyl, carboxyl, nitro, cyano, amino, or unsubstituted or R'-substituted: C1-C36 chain alkyl, C3-C36 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 alkylsilyl, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, C6-C60 aryloxy, or C5-C60 heteroaryl; The two adjacent R's mentioned above are either not connected or connected to form a ring; each R' is independently selected from one of the following: deuterium, halogen, cyano, amino, C2-C10 alkenyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 alkylsilyl, C1-C10 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

2. The organic compound according to claim 1, characterized in that, Rings A, B, C, and D are each independently the structure shown in equation (a), (b), or (c), or any of the structures in equations (1-1), (1-2), and (1-3), and at least one of rings A, B, C, and D is any of the structures in equations (1-1), (1-2), and (1-3); ring E is the structure shown in equation (a). In formulas (a), (b) and (c), the double bonds in the dashed lines represent the fusion positions of the group in formula (1); In equations (a), (b), and (c), Z 1 Z 2 Z 3 Z 4 Z 5 Z 6 Z 7 Z 8 Z 9 Z 10 Z 11 Z 12 Each is independently selected from C, CH, or N; In equation (c), Z is selected from O, S, and NR. 1 or CR 2 R 3 ; R 1 R 2 R 3 It is either not connected to adjacent groups or forms a ring through chemical bonds; R 2 With R 3 They are either not connected or connected in a loop; R 1 R 2 R 3 Each is independently selected from one of the following: unsubstituted or R”-substituted C1-C20 chain alkyl, unsubstituted or R”-substituted C3-C20 cycloalkyl, unsubstituted or R”-substituted C6-C60 aryl, and unsubstituted or R”-substituted C3-C60 heteroaryl; "R" is selected from any one of deuterium, halogen, cyano, amino, C2-C20 alkenyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

3. The organic compound according to claim 2, characterized in that, In equation (c), Z is selected from O, S, or NR. 1 ;R 1 It is either not connected to adjacent groups or is linked to form a ring through chemical bonds; R 1 Selected from one of the following groups, either unsubstituted or R”-substituted: phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphylphenyl, terphenyl, trimerphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorenyl, trimerinyl, isotrimerininyl, spirotrimerininyl, spiroisotrimerininyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, Thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, isoindolyl, carbazoleyl, indocarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazolyl, benzimidazoleyl, naphthiazoleyl, phenanthrimidazoleyl, pyridiniumimidazoleyl, pyraziniumimidazoleyl, quinoxalolineimidazolyl, oxazolyl, benzooxazolyl, naphthiazoleyl, anthraquinoxazol 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazathanel, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenthiazinyl, naphridinyl, azacarbazolyl, benzocarbaolinyl, phenanthrolinel, 1,2, 3-Triazolyl, 1,2,4-Triazolyl, Benzotriazolyl, 1,2,3-Oxadiazolyl, 1,2,4-Oxadiazolyl, 1,2,5-Oxadiazolyl, 1,2,3-Thiadiazolyl, 1,2,4-Thiadiazolyl, 1,2,5-Thiadiazolyl, 1,3,4-Thiadiazolyl, 1,3,5-Triazinyl, 1,2,4-Triazinyl, 1,2,3-Triazinyl, Tetrazolyl, 1,2,4,5-Tetraazinyl, 1,2,3,4-Tetraazinyl, 1,2,3,5-Tetraazinyl; "R" is selected from one of the following: deuterium, cyano, C1-C6 chain alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

4. The organic compound according to claim 1, characterized in that, The rings A, B, C, and D are not selected from formulas (1-1), (1-2), or (1-3), but are each independently selected from one of the aromatic rings of C6 to C30 and the heteroaromatic rings of C5 to C30, and ring E represents an aromatic ring of C6 to C30. Preferably, the ring A, ring B, ring C, or ring D not selected from formula (1-1), formula (1-2), or formula (1-3) is each independently selected from phenyl, naphthyl, anthraceneyl, fluorenyl, furanyl, benzofuranyl, dibenzofuranyl, indolyl, benzoindolyl, carbazoleyl, indolocarbazoleyl, benzothiopheneyl, dibenzothiopheneyl, thiopheneyl, benzoanthrayl, phenanthyl, pyrene, pyrene, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzopyreneyl, biphenyl, amphyl, terphenyl, triphenyl, triphenyl, tetraphenyl, diphenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, isobenzothiopheneyl The ring is selected from any one of the following: phenyl, dibenzothiophenyl, pyrroleyl, isoindolyl, carbazoyl, indoxarcarbazoyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indoxolyl, imidazoyl, benzimidazolyl, naphthimidazolyl, phenanthridinemidazolyl, pyridiniumimidazoyl, pyraziniumimidazoyl, quinoxoliniumimidazoyl, oxazolyl, benzooxazolyl, naphthimidazolyl, anthraquinoxazolyl, phenanthridinemidazolyl, 1,2-thiazoyl, 1,3-thiazoyl, benzothiazoyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, and quinoxolinyl; ring E is selected from a benzene ring. More preferably, the ring A, ring B, ring C, or ring D not selected from formulas (1-1), (1-2), and (1-3) is each independently selected from one of phenyl, naphthyl, anthraceneyl, fluorenyl, furanyl, benzofuranyl, dibenzofuranyl, indolyl, benzoindolyl, carbazoyl, indolocarbazoyl, benzothiopheneyl, dibenzothiopheneyl, thiopheneyl, phenanthryl, pyridinyl, quinolinyl, isoquinolinyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, and quinoxalinyl. More preferably, the rings A, B, C, or D not selected from formulas (1-1), (1-2), and (1-3) are each independently selected from one of phenyl, naphthyl, anthraceneyl, fluorenyl, furanyl, benzofuranyl, dibenzofuranyl, indolyl, benzoindolyl, carbazoyl, indolocarbazoyl, benzothiophenyl, dibenzothiophenyl, and thiophenyl; ring E is selected from a benzene ring.

5. The organic compound according to any one of claims 1, 2, or 4, characterized in that, The rings A, B, C, and D are each independently represented as one of the aromatic rings of C6 to C30 and the heteroaromatic rings of C5 to C30, and at least one of the rings A, B, C, and D is any structure of formula (1-1), formula (1-2), or formula (1-3). Preferably, only one of rings A, B, C, and D has any structure from equations (1-1), (1-2), and (1-3); Alternatively, preferably, two of rings A, B, C, and D are any structures from equations (1-1), (1-2), and (1-3); More preferably, only one of rings A and B has any one of the structures in equations (1-1), (1-2), and (1-3), and only one of rings C and D has any one of the structures in equations (1-1), (1-2), and (1-3); More preferably, ring A is any one of the structures in formula (1-1), formula (1-2), and formula (1-3), while ring D is any one of the structures in formula (1-1), formula (1-2), and formula (1-3); or, ring B is any one of the structures in formula (1-1), formula (1-2), and formula (1-3), while ring C is any one of the structures in formula (1-1), formula (1-2), and formula (1-3).

6. The organic compound according to claim 1, characterized in that, It has the structure shown in equation (2-1): Among them, R a R b R c R d R e The definitions are the same as those in equation (1); At least one of the rings A, B, C, and D is any structure of equation (1-1), (1-2), or (1-3), and the rings A, B, C, or D not selected from equation (1-1), (1-2), and (1-3) are each independently the structure shown in equation (a), (b), or (c). In equations (a), (b), and (c), Z 1 -Z 12 The definition of Z is the same as that in claim 2; Preferably, only one of rings A, B, C, and D is any structure of equation (1-1), (1-2), or (1-3), and rings A, B, C, or D not selected from equations (1-1), (1-2), and (1-3) are each independently the structure shown in equation (a), (b), or (c). Alternatively, preferably, only two of rings A, B, C, and D are structures of any one of equations (1-1), (1-2), and (1-3), and the remaining rings A, B, C, or D not selected from equations (1-1), (1-2), and (1-3) are each independently structures shown in equation (a), (b), or (c). More preferably, only one of rings A and B has any one of the structures in equations (1-1), (1-2), and (1-3), while only one of rings C and D has any one of the structures in equations (1-1), (1-2), and (1-3), and the structures not selected from equations (1-1), (1-2), and (1-3) are each independently the structures shown in equation (a), (b), or (c). More preferably, ring A is any structure of formula (1-1), formula (1-2), or formula (1-3), ring D is any structure of formula (1-1), formula (1-2), or formula (1-3), and the structures not selected from formula (1-1), formula (1-2), or formula (1-3) are each independently the structures shown in formula (a), formula (b), or formula (c); or, ring B is any structure of formula (1-1), formula (1-2), or formula (1-3), ring C is any structure of formula (1-1), formula (1-2), or formula (1-3), and the structures not selected from formula (1-1), formula (1-2), or formula (1-3) are each independently the structures shown in formula (a), formula (b), or formula (c). More preferably, in formula (2-1), rings A, B, C, and D are not selected from formulas (1-1), (1-2), and (1-3), but are each independently selected from one of the following: phenyl, naphthyl, anthraceneyl, fluorenyl, furanyl, benzofuranyl, dibenzofuranyl, indolyl, benzoindolyl, carbazoyl, indolocarbazoyl, benzothiopheneyl, dibenzothiopheneyl, thiopheneyl, phenanthryl, pyridinyl, quinolinyl, isoquinolinyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, and quinoxalinyl. Most preferably, in formula (2-1), rings A, B, C, and D are not selected from formulas (1-1), (1-2), and (1-3), but are each independently selected from one of phenyl, naphthyl, anthraceneyl, fluorenyl, furanyl, benzofuranyl, dibenzofuranyl, indolyl, benzoindolyl, carbazoyl, indolocarbazoyl, benzothiophenyl, dibenzothiophenyl, and thiophenyl.

7. The organic compound according to any one of claims 1-6, characterized in that, The R a R b R c R d R e Each group is independently selected from hydrogen, deuterium, halogen, cyano, or unsubstituted or R'-substituted groups of the following: C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C20 arylamino, C3-C20 heteroarylamino, C6-C30 aryl, C6-C30 aryloxy, and C5-C30 heteroaryl. R' is selected from one of the following: deuterium, halogen, cyano, amino, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 alkylsilyl, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, the R a R b R c R d R e Each of the following substituents is independently selected from hydrogen, deuterium, cyano, halogen, or a combination of one or two of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, pyryl, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphyl, terphenyl, triphenyl, tetraphenyl, Fluorenyl, spirodifluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indofluorenyl, trimerinyl, isotrimericininyl, spirotrimericininyl, spiroisotrimericininyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, isobenzothiopheneyl, dibenzothiopheneyl, pyrroleyl, isoindoleyl, carbazoleyl, indocarbazoleyl, pyridinyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazoyl, benzimidazoleyl, naphthizimidazoleyl, phenanthrenezimidazoleyl, pyridinium imidazoyl, pyrazine Imidazolyl, quinoxaloylimidazolyl, oxazolyl, benzoxoxazolyl, naphthoxazolyl, anthraxoxazolyl, phenanthoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxaloyl, 1,5-diazaanthrayl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl Benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetraazinyl, 1,2,3,4-tetraazinyl, 1,2,3,5-tetraazinyl, purinyl, pteridyl, indazyl, benzothiadiazolyl, 9,9-dimethylacridyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl or methoxy; More preferably, the R a R b R c R d R e Each of the following groups is independently selected from hydrogen, deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 2-methylbutyl, trifluoromethyl, pentafluoroethyl, phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthrene, benzo[a]phenanthrene, pyrene, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, furanyl, benzo[a]furanyl, isobenzo[a]furanyl, dibenzo[a]furanyl, thienyl, benzo[a]thienyl, isobenzo[a]thienyl, dibenzo[a]thienyl, pyrroleyl, isoindoleyl, carbazoleyl, indoxocarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, pyrazolyl, indazoleyl, imidazolyl. Pyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, pyrazinyl, phenazinyl, phenothiazinyl, naphridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetraazinyl, inazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, or methoxy.

8. The organic compound according to claim 1, wherein the compound is selected from the following specific structural compounds:

9. The application of the organic compound according to any one of claims 1-8 as a functional material in organic electronic devices, wherein the organic electronic devices are organic electroluminescent devices, optical sensors, solar cells, organic thin-film transistors, or organic field-effect transistors; The organic compound is used as a light-emitting layer material in organic electroluminescent devices, specifically as a light-emitting material in the light-emitting layer.

10. An organic electroluminescent device, comprising a substrate, and an anode layer, a plurality of light-emitting functional layers, and a cathode layer sequentially formed on the substrate; wherein the light-emitting functional layers include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and a light-emitting layer is located between the hole transport layer and the electron transport layer, wherein the light-emitting layer contains an organic compound as described in any one of claims 1-8.

11. A display device comprising the organic electroluminescent device of claim 10.

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