Organic compound, application thereof and organic electroluminescent device adopting organic compound

Abstract

The invention relates to an organic compound, application of the compound and an organic electroluminescent device containing the compound. The organic compound disclosed by the invention has a structure as shown in a formula (1), wherein a ring A, a ring B, a ring C, a ring D and a ring E independently represent one of C6-C60 aromatic rings and C5-C60 heteroaromatic rings; w1, W2 and W3 are respectively and independently selected from a single bond, O, CO, SO2, S, Se, NR1, CR2R3 or SiR4R5; and m1, m2 and m3 are respectively and independently 0 or 1. After the compound disclosed by the invention is prepared and applied to the organic electroluminescent device, the device has good performances of high color purity and high luminous efficiency and also has extremely long service life.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, and particularly to an organic compound, as well as the application of this luminescent material and organic electroluminescent devices containing the compound. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are a type of device with a sandwich-like structure, consisting of positive and negative electrode layers and an organic functional material layer sandwiched between them. When a voltage is applied to the electrodes of an OLED device, positive charges are injected from the positive electrode and negative charges from the negative electrode. Under the influence of an electric field, the positive and negative charges migrate, meet, and recombine within the organic layer to emit light. Due to their advantages such as high brightness, fast response, wide viewing angle, simple manufacturing process, and flexibility, OLED devices have attracted significant attention in the fields of new display technology and new lighting technology. Currently, this technology is widely used in display panels for new lighting fixtures, smartphones, and tablets, and its application is expected to expand further into large-size display products such as televisions. It is a rapidly developing and technologically demanding new display technology.

[0003] In the selection of OLED light-emitting materials, singlet-state luminescent fluorescent materials have good lifetimes and low prices, but low efficiency; triplet-state luminescent phosphorescent materials have high efficiency, but are expensive, and the lifetime problem of blue light-emitting materials has not yet been solved. Adachi of Kyushu University in Japan proposed a new class of organic light-emitting materials, namely thermally activated delayed fluorescence (TADF) materials. This type of material utilizes donor-acceptor separation to obtain 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] To address the aforementioned technical problems, this invention provides an organic compound exhibiting exceptionally long stability. The specific technical solution is as follows:

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

[0007]

[0008] In formula (1), rings A, B, C, D, and E each independently represent one of the aromatic rings of C6 to C60 and the heteroaromatic rings of C5 to C60;

[0009] W1, W2, and W3 are each independently selected from single bonds, O, CO, SO2, S, Se, NR1, CR2R3, or SiR4R5; m1, m2, and m3 are each independently 0 or 1;

[0010] R1, R2, R3, R4, and R5 are either not connected to adjacent groups or are connected in a ring; R2 and R3 are either not connected to each other or are connected in a ring; R4 and R5 are either not connected to each other or are connected in a ring.

[0011] R1, R2, R3, R4, and R5 are each independently selected from one of the following groups that are unsubstituted or R' substituted: C1-C36 chain alkyl, C3-C36 cycloalkyl, C6-C30 arylamino, C6-C60 aryl, C6-C60 aryloxy, and C5-C60 heteroaryl.

[0012] The 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;

[0013] 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 fusion bond;

[0014] 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;

[0015] R a R b R c R d Re 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, and C5-C60 heteroaryl;

[0016] The two adjacent R's are either not connected or connected to form a ring; R' is selected from one or a combination of two 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.

[0017] 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.

[0018] 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.

[0019] 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.

[0020] In this specification, "each independently" means that when there are multiple subjects, they may be the same or different from each other.

[0021] 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.

[0022] 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.

[0023] Examples of halogens in this specification include fluorine, chlorine, bromine, and iodine.

[0024] In this invention, unless otherwise specified, aryl and heteroaryl groups include both monocyclic and fused-ring groups.

[0025] 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.

[0026] 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.

[0027] 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.

[0028] 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.

[0029] C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0030] C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0031] C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0032] C2-C10 can all be C2, C3, C4, C5, C6, C7, C8, C9 or C10.

[0033] 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. The compounds include naphthyl, fluorenyl, tetraphenyl, and their derivatives. The naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracel group is selected from 1-anthrayl, 2-anthrayl, and 9-anthrayl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrene group is selected from 1-pyrene, 2-pyrene, and 4-pyrene; and the tetraphenyl group is selected from 1-tetraphenyl, 2-tetraphenyl, and 9-tetraphenyl. 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.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] Examples of C6-C30 arylamino groups mentioned in this invention include phenylamino, methylphenylamino, naphthylamino, anthraceneylamino, phenanthreneamino, and biphenylamino.

[0038] Examples of C3-C30 heteroaryl amino groups mentioned in this invention include pyridinyl amino, pyrimidinyl amino, and dibenzofuranyl amino.

[0039] 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] Furthermore, in the general formula (1) of the present invention, the R a R b R c R d R e Each element is independently connected to the ring structure it is attached to via a single bond or a fused bond, preferably via a single bond.

[0046] Further, in the general formula (1) of the present invention, rings A, B, C, and D are each independently the structure shown in formula (a), formula (b), or formula (c), and ring E is the structure shown in formula (a); the dashed double bonds represent the fusion positions of the following groups in formula (1), any one of the dashed double bonds (b1), (b2), and (b3) represents the fusion position of the group in formula (b), and any one of the dashed double bonds (c1), (c2), and (c3) represents the fusion position of the group in formula (c):

[0047]

[0048] 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;

[0049] 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;

[0050] 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;

[0051] "R" is selected from any one or a combination of two of the following: 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.

[0052] Furthermore, in the general formula (1) of the present invention, at least one of ring A, ring B, ring C, and ring D is the structure shown in formula (c), and ring E is the structure shown in formula (a);

[0053] Preferably, in formula (c), Z is selected from O, S, or NR. 1 ;R 1 Selected from one of the following groups, either unsubstituted or R”-substituted: phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, pyrene, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, amphylphenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthryl, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorenyl, trimenyl, isotrimeric indo[a], spirotrimeric indo[a], spiroisotrimeric indo[a] alkyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, pyrroleyl, isoindolyl, carbazoleyl, indolecarbazoleyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, naphthyl Imidazolyl, phenanthreneimidazolyl, pyridiniumimidazolyl, pyraziniumimidazolyl, quinoxaliniumimidazolyl, oxazolyl, benzoxoxazolyl, naphthoxoxazolyl, anthraquinoneiumimidazolyl, phenanthreneiumimidazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthrayl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diaza Xyripyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetrazapirylene, 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

[0054] 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-Tetrazinyl, 1,2,3,4-Tetrazinyl, 1,2,3,5-Tetrazinyl;

[0055] "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.

[0056] Furthermore, in the general formula (1) of the present invention, ring A, ring B, ring C, and ring D each independently represent one of an aromatic ring of C6 to C30 and a heteroaromatic ring of C5 to C30, and ring E independently represents an aromatic ring of C6 to C30;

[0057] Preferably, ring A, ring B, ring C, and ring D are each independently selected from benzene ring, naphthyl ring, anthracene ring, fluorene ring, furan, benzofuran, dibenzofuran, indole, benzoindole, carbazole, indole-carbazole, benzothiophene, dibenzothiophene, thiophene, benzoanthrayl, phenanthrayl, pyrene, pyrene, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzopyrene, biphenyl, amphylphenyl, terphenyl, triphenyl, triphenyl, tetraphenyl, diphenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, isoindole The ring E is selected from any one of the following: carbazolyl, indocarbazolyl, pyridinyl, quinolinyl, isoquinolinyl, acridinel, phenanthridinel, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazolel, imidazolyl, benzimidazolel, naphthimidazolel, phenanthridinemidazolel, pyridinimidazolel, pyrazinimidazolel, quinoxalinimidazolel, oxazolyl, benzooxazolyl, naphthimidazolel, anthraquinoxazolyl, phenanthridinemidazolel, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, and quinoxalinyl; ring E is selected from a benzene ring.

[0058] More preferably, ring A, ring B, ring C, and ring D are each independently selected from one of the following: benzene ring, naphthalene ring, anthracene ring, fluorene ring, furan, benzofuran, dibenzofuran, indole, benzoindole, carbazole, indole-carbazole, benzothiophene, dibenzothiophene, and thiophene; ring E is selected from the benzene ring.

[0059] Further, in the general formula (1) of the present invention, m3 is 0, and m1 and m2 are each independently 0 or 1; W1 and W2 are each independently selected from CC single bond, O, CO, SO2, S, NR1, CR2R3 or SiR4R5; preferably, m3 is 0, and m1 and m2 are each independently 0 or 1; W1 and W2 are each independently selected from CC single bond, CO, NR1 or CR2R3; more preferably, m3 is 0, and m1 and m2 are each independently 0 or 1; W1 and W2 are both selected from CC single bond.

[0060] Furthermore, the organic compounds of the present invention have the structure shown in formula (2-1):

[0061]

[0062] Among them, R a R b Rc R d R e The definitions of W1, W2, m1, and m2 are the same as those in equation (1); rings A, B, C, and D are each independently the structures shown in equation (a) or equation (c);

[0063] Preferably, m1 and m2 are both 1, W1 and W2 independently represent CC single bonds, CO, NR1 or CR2R3, R1, R2, and R3 are not connected to adjacent rings or are connected by single bonds; R2 and R3 are not connected or are connected to form a ring.

[0064] Alternatively, preferably, one of m1 and m2 is 0 and the other is 1, W1 and W2 represent CC single bonds, CO, NR1 or CR2R3, R1, R2, and R3 are not connected to adjacent rings or are connected by single bonds; R2 and R3 are not connected or are connected to form a ring.

[0065] More preferably, W1 and W2 represent CC single bonds, CO, NR1, or CR2R3, and R1, R2, and R3 are 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, thiophene, benzo[a]thiophene, isobenzo[a]thiophene, dibenzo[a]thiophene, pyrrole, isoindole, carbazole, indenecarbazole, and pyridyl. Quinolinyl, isoquinolinyl, pyrazolyl, indazoleyl, imidazolyl, pyridinyl, 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, indazolyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl or methoxy;

[0066] More preferably, m1 and m2 are both 1, and W1 and W2 both represent CC single bonds.

[0067] Furthermore, the organic compounds of the present invention have the structure shown in formula (3-1):

[0068]

[0069] Among them, R a R b R c R d R e The definitions are the same as those in equation (1).

[0070] Furthermore, in the above general formula of the present invention, 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, C5-C30 heteroaryl; wherein 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 fusion bond;

[0071] 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.

[0072] 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, isotrimerininyl, spirotrimerininyl, spiroisotrimerininyl, 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, naphthiazoleyl, phenanthreneimidazoleyl, pyridiniumimidazoleyl, pyrazinyl Imidazolyl, quinoxolinoimidazolyl, oxazolyl, benzoxoxazolyl, naphthoxazolyl, anthraquinoxazolyl, phenanthoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxolinyl, 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, phenthiazinyl, naphridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzoxazolyl Triazolyl, 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, indazinyl, benzothiadiazolyl, 9,9-dimethylacridyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl or methoxy; 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 fusion bond;

[0073] 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, thiophene, benzo[a]thiophene, isobenzo[a]thiophene, dibenzo[a]thiophene, pyrrole, isoindole, carbazole, indoxacarbazole, pyridinyl, quinolinyl, isoquinolinyl, pyrazolyl, indazole, imidazolyl, pyridazine. The following are listed: 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, indazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, or methoxy; The R a R b R c R d R e Each element is independently connected to the ring structure it is attached to via a single bond or a fused bond.

[0074] Furthermore, the general formula compounds of the present invention can preferably include the following specific structural compounds A1 to A140, which are merely representative examples:

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082] The compounds of this invention introduce an adamantane lock structure on both sides of the classic boron-nitrogen core, connecting the two benzene rings, eliminating the original repulsion between hydrogen atoms, significantly enhancing molecular rigidity, further reducing the full width at half maximum (FWHM) (≤25nm), improving color purity, and consequently significantly improving the efficiency of the light-emitting device, providing guidance for constructing novel narrow-spectrum light-emitting materials. Simultaneously, due to the stereochemistry of the adamantane structure, it has significant steric hindrance, effectively increasing the intermolecular distance, thereby suppressing the disadvantages of efficiency reduction, spectral broadening, and decreased stability caused by molecular stacking. Furthermore, it can reduce the interaction between the host and dye, and between dyes, in the device, improving the device's luminous efficiency, lifetime, and other performance characteristics. Moreover, the adamantane lock structure has sp... 3 Hybridized carbon atoms offer better stability compared to heteroatom-locked structures with lone pairs of electrons, thus enabling the fabrication of highly efficient OLED devices.

[0083] Furthermore, when one of the rings A, B, C, and D in the compound of this invention is designed as a fused benzene ring structure, the conjugated planar structure of the molecule can be further broadened, thereby dispersing the electron density of the molecule, enhancing molecular stability, and improving device lifetime. Moreover, this enhancement and improvement occur with the increase of fused benzene structures in rings A, B, C, and D.

[0084] 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.

[0085] 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.

[0086] 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.

[0087] 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 A140 mentioned above. Detailed Implementation

[0088] 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.

[0089] 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).

[0090] The synthetic method of the compound of the present invention is briefly described below. First, nucleophilic substitution and the Buchwald–Hartwig reaction are used to obtain polybrominated intermediate I. Then, after lithium halide exchange with n-butyllithium, nucleophilic addition with adamantane followed by acidification and cyclization are performed to obtain intermediate II. Finally, under the action of tert-butyllithium, electrophilic boronization with boron tribromide is performed to obtain the target compound.

[0091] Synthesis Examples

[0092] Example 1: Synthesis of Compound A1

[0093]

[0094] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A1-1 (5 mmol) was dissolved in 10 mL of dry tetrahydrofuran and cooled to -78 °C. A pentane solution of n-butyllithium (1 M, 12 mL) was added, and the reaction was allowed to proceed at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 mL of dry tetrahydrofuran pre-cooled to -78 °C. This solution was then slowly injected into the A1-1 solution at -78 °C, and the mixture was slowly brought to room temperature and reacted for 12 hours. After the reaction was complete, a small amount of methanol was added to quench the reaction, the solvent was evaporated under reduced pressure, and 100 mL of glacial acetic acid and 10 mL of concentrated hydrochloric acid were added. The mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated sodium carbonate aqueous solution, extracted with dichloromethane, and the organic phase was collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The compound A1-2 was separated by silica gel column chromatography using petroleum ether:dichloromethane = 5:1 as the developing solvent.

[0095] Compound A1-2 (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. The mixture was then heated to 30 °C and stirred for another 1 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 (21% yield, HPLC purity 99.57%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 680.34; Elemental analysis results: Theoretical values: C, 88.23; H, 6.07; B, 1.59; N, 4.12 (%); Experimental values: C, 88.23; H, 6.07; B, 1.60; N, 4.11 (%).

[0096] Example 2 Synthesis of Compound A3

[0097]

[0098] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A3-1 (5 mmol) was dissolved in 10 mL of dry tetrahydrofuran and cooled to -78 °C. A pentane solution of n-butyllithium (1 M, 12 mL) was added, and the reaction was allowed to proceed at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 mL of dry tetrahydrofuran pre-cooled to -78 °C. This solution was then slowly injected into the A3-1 solution at -78 °C, and the mixture was slowly brought to room temperature for 12 hours. After the reaction was complete, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, and 100 mL of glacial acetic acid and 10 mL of concentrated hydrochloric acid were added. The mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated sodium carbonate aqueous solution. The organic phase was extracted with dichloromethane and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The compound A3-2 was separated by silica gel column chromatography using petroleum ether:dichloromethane = 5:1 as the developing solvent.

[0099] Compound A3-2 (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. The mixture was then heated to 30 °C and stirred for another 1 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 A3 (23% yield, HPLC purity 99.71%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 904.59; Elemental analysis results: Theoretical values: C, 87.58; H, 8.13; B, 1.19; N, 3.10 (%); Experimental values: C, 87.58; H, 8.13; B, 1.18; N, 3.11 (%).

[0100] Example 3 Synthesis of compound A13

[0101]

[0102] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A13-1 (5 mmol) was dissolved in 10 mL of dry tetrahydrofuran and cooled to -78 °C. A pentane solution of n-butyllithium (1 M, 12 mL) was added, and the reaction was allowed to proceed at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 mL of dry tetrahydrofuran pre-cooled to -78 °C. This solution was then slowly injected into the A13-1 solution at -78 °C, and the temperature was slowly raised to room temperature for 12 hours. After the reaction was complete, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, and 100 mL of glacial acetic acid and 10 mL of concentrated hydrochloric acid were added. The mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated sodium carbonate aqueous solution. The organic phase was extracted with dichloromethane and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The compound A13-2 was separated by silica gel column chromatography using petroleum ether:dichloromethane = 10:1 as the developing solvent.

[0103] Compound A13-2 (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. The mixture was then heated to 30 °C and stirred for another 1 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 A13 (25% yield, HPLC purity 99.27%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 892.31; Elemental analysis results: Theoretical values: C, 83.39; H, 5.08; B, 1.21; N, 3.14; S, 7.18 (%); Experimental values: C, 83.39; H, 5.08; B, 1.21; N, 3.15; S, 7.17 (%).

[0104] Example 4 Synthesis of compound A20

[0105]

[0106] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A20-1 (5 mmol) was dissolved in 10 mL of dry tetrahydrofuran and cooled to -78 °C. A pentane solution of n-butyllithium (1 M, 12 mL) was added, and the reaction was allowed to proceed at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 mL of dry tetrahydrofuran pre-cooled to -78 °C. This solution was then slowly injected into the A20-1 solution at -78 °C, and the mixture was slowly brought to room temperature for 12 hours. After the reaction was complete, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, and 100 mL of glacial acetic acid and 10 mL of concentrated hydrochloric acid were added. The mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated sodium carbonate aqueous solution. The organic phase was extracted with dichloromethane and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The compound A20-2 was separated by silica gel column chromatography using petroleum ether:dichloromethane (3:1) as the developing solvent.

[0107] Compound A20-2 (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. The mixture was then heated to 30 °C and stirred for another 1 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 A20 (22% yield, HPLC purity 99.03%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1051.41; Elemental analysis results: Theoretical values: C, 86.76; H, 5.17; B, 1.03; N, 3.99; S, 3.05 (%); Experimental values: C, 86.78; H, 5.17; B, 1.02; N, 3.97; S, 3.06 (%).

[0108] Example 5 Synthesis of compound A22

[0109]

[0110] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A22-1 (5 mmol) was dissolved in 10 mL of dry tetrahydrofuran and cooled to -78 °C. A pentane solution of n-butyllithium (1 M, 12 mL) was added, and the reaction was allowed to proceed at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 mL of dry tetrahydrofuran pre-cooled to -78 °C. This solution was then slowly injected into the A22-1 solution at -78 °C, and the mixture was slowly brought to room temperature and reacted for 12 hours. After the reaction was complete, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, and 100 mL of glacial acetic acid and 10 mL of concentrated hydrochloric acid were added. The mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated sodium carbonate aqueous solution. The organic phase was extracted with dichloromethane and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The compound A22-2 was separated by silica gel column chromatography using petroleum ether:dichloromethane (3:1) as the developing solvent.

[0111] Compound A22-2 (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. The mixture was then heated to 30 °C and stirred for another 1 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 compound A22 (25% yield, HPLC purity 99.13%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1010.45; Elemental analysis results: Theoretical values: C, 87.91; H, 5.48; B, 1.07; N, 5.54 (%); Experimental values: C, 87.91; H, 5.47; B, 1.07; N, 5.55 (%).

[0112] Example 6 Synthesis of compound A38

[0113]

[0114] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A38-1 (5 mmol) was dissolved in 10 mL of dry tetrahydrofuran and cooled to -78 °C. A pentane solution of n-butyllithium (1 M, 12 mL) was added, and the reaction was allowed to proceed at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 mL of dry tetrahydrofuran pre-cooled to -78 °C. This solution was then slowly injected into the A38-1 solution at -78 °C, and the mixture was slowly brought to room temperature for 12 hours. After the reaction was complete, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, and 100 mL of glacial acetic acid and 10 mL of concentrated hydrochloric acid were added. The mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated sodium carbonate aqueous solution. The organic phase was extracted with dichloromethane and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The compound A38-2 was separated by silica gel column chromatography using petroleum ether:dichloromethane = 5:1 as the developing solvent.

[0115] Compound A38-2 (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. The mixture was then heated to 30 °C and stirred for another 1 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 A38 (26% yield, HPLC purity 99.25%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 882.47; Elemental analysis results: Theoretical values: C, 87.06; H, 6.74; B, 1.22; N, 3.17; O, 1.81 (%); Experimental values: C, 87.06; H, 6.74; B, 1.21; N, 3.17; O, 1.82 (%).

[0116] Example 7 Synthesis of Compound A40

[0117]

[0118] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A40-1 (5 mmol) was dissolved in 10 mL of dry tetrahydrofuran and cooled to -78 °C. A pentane solution of n-butyllithium (1 M, 12 mL) was added, and the reaction was allowed to proceed at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 mL of dry tetrahydrofuran pre-cooled to -78 °C. This solution was then slowly injected into the A40-1 solution at -78 °C, and the mixture was slowly brought to room temperature for 12 hours. After the reaction was complete, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, and 100 mL of glacial acetic acid and 10 mL of concentrated hydrochloric acid were added. The mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated sodium carbonate aqueous solution. The organic phase was extracted with dichloromethane and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The compound A40-2 was separated by silica gel column chromatography using petroleum ether:dichloromethane = 5:1 as the developing solvent.

[0119] Compound A40-2 (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. The mixture was then heated to 30 °C and stirred for another 1 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 A40 (21% yield, HPLC purity 99.33%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 955.50; Elemental analysis results: Theoretical values: C, 87.94; H, 6.54; B, 1.13; N, 4.40 (%); Experimental values: C, 87.94; H, 6.54; B, 1.12; N, 4.41 (%).

[0120] Example 8 Synthesis of compound A57

[0121]

[0122] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A57-1 (5 mmol) was dissolved in 10 mL of dry tetrahydrofuran and cooled to -78 °C. A pentane solution of n-butyllithium (1 M, 12 mL) was added, and the reaction was allowed to proceed at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 mL of dry tetrahydrofuran pre-cooled to -78 °C. This solution was then slowly injected into the A57-1 solution at -78 °C, and the mixture was slowly brought to room temperature for 12 hours. After the reaction was complete, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, and 100 mL of glacial acetic acid and 10 mL of concentrated hydrochloric acid were added. The mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated sodium carbonate aqueous solution. The organic phase was extracted with dichloromethane and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The compound A57-2 was separated by silica gel column chromatography using petroleum ether:dichloromethane = 5:1 as the developing solvent.

[0123] Compound A57-2 (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. The mixture was then heated to 30 °C and stirred for another 1 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 A57 (24% yield, HPLC purity 99.02%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1110.48; Elemental analysis results: Theoretical values: C, 88.63; H, 5.35; B, 0.97; N, 5.04 (%); Experimental values: C, 88.63; H, 5.35; B, 0.96; N, 5.05 (%).

[0124] Example 9 Synthesis of Compound A78

[0125]

[0126] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A78-1 (5 mmol) was dissolved in 10 mL of dry tetrahydrofuran and cooled to -78 °C. A pentane solution of n-butyllithium (1 M, 12 mL) was added, and the reaction was allowed to proceed at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 mL of dry tetrahydrofuran pre-cooled to -78 °C. This solution was then slowly injected into the A78-1 solution at -78 °C, and the mixture was slowly brought to room temperature for 12 hours. After the reaction was complete, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, and 100 mL of glacial acetic acid and 10 mL of concentrated hydrochloric acid were added. The mixture was then heated to reflux. After 2 hours of reaction, the mixture was neutralized with a saturated sodium carbonate aqueous solution. The organic phase was extracted with dichloromethane and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The compound A78-2 was separated by silica gel column chromatography using petroleum ether:dichloromethane = 10:1 as the developing solvent.

[0127] Compound A78-2 (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. The mixture was then heated to 30 °C and stirred for another 1 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 A78 (22% yield, HPLC purity 99.17%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 840.37; Elemental analysis results: Theoretical values: C, 85.70; H, 5.87; B, 1.29; N, 3.33; S, 3.81 (%); Experimental values: C, 85.70; H, 5.87; B, 1.28; N, 3.32; S, 3.81 (%).

[0128] Example 10 Synthesis of Compound A93

[0129]

[0130] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A93-1 (5 mmol) was dissolved in 10 mL of dry tetrahydrofuran and cooled to -78 °C. A pentane solution of n-butyllithium (1 M, 12 mL) was added, and the reaction was allowed to proceed at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 mL of dry tetrahydrofuran pre-cooled to -78 °C. This solution was then slowly injected into the A93-1 solution at -78 °C, and the mixture was slowly brought to room temperature and reacted for 12 hours. After the reaction was complete, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, and 100 mL of glacial acetic acid and 10 mL of concentrated hydrochloric acid were added. The mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated sodium carbonate aqueous solution. The organic phase was extracted with dichloromethane and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The compound A93-2 was separated by silica gel column chromatography using petroleum ether:dichloromethane = 4:1 as the developing solvent.

[0131] Compound A93-2 (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. The mixture was then heated to 30 °C and stirred for another 1 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 = 20:1 as the developing solvent to obtain the target compound A93 (21% yield, HPLC purity 99.66%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 943.41; Elemental analysis results: Theoretical values: C, 89.06; H, 5.34; B, 1.15; N, 4.45 (%); Experimental values: C, 89.06; H, 5.33; B, 1.15; N, 4.46 (%).

[0132] Example 11 Synthesis of compound A108

[0133]

[0134] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A108-1 (5 mmol) was dissolved in 10 mL of dry tetrahydrofuran and cooled to -78 °C. A pentane solution of n-butyllithium (1 M, 12 mL) was added, and the reaction was allowed to proceed at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 mL of dry tetrahydrofuran pre-cooled to -78 °C. This solution was then slowly injected into the A108-1 solution at -78 °C, and the mixture was slowly brought to room temperature for 12 hours. After the reaction was complete, a small amount of methanol was added to quench the reaction. The solvent was evaporated under reduced pressure, and 100 mL of glacial acetic acid and 10 mL of concentrated hydrochloric acid were added. The mixture was then heated to reflux. After reacting for 2 hours, the mixture was neutralized with a saturated sodium carbonate aqueous solution. The organic phase was extracted with dichloromethane and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The compound A108-2 was separated by silica gel column chromatography using petroleum ether:dichloromethane (10:1) as the developing solvent.

[0135] Compound A108-2 (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. The mixture was then heated to 30 °C and stirred for another 1 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 A108 (23% yield, HPLC purity 99.61%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1058.45; Elemental analysis results: Theoretical values: C, 88.45; H, 5.23; B, 1.02; N, 5.29 (%); Experimental values: C, 88.45; H, 5.22; B, 1.03; N, 5.29 (%).

[0136] Example 12 Synthesis of compound A123

[0137]

[0138] In a double-necked flask under a nitrogen atmosphere, the polybrominated precursor A123-1 (5 mmol) was dissolved in 10 mL of dry tetrahydrofuran and cooled to -78 °C. A pentane solution of n-butyllithium (1 M, 12 mL) was added, and the reaction was allowed to proceed at this temperature for 1 hour. Reactant Q1 (12 mmol) was dissolved in 40 mL of dry tetrahydrofuran pre-cooled to -78 °C. This solution was then slowly injected into the A123-1 solution at -78 °C, and the mixture was slowly brought to room temperature and reacted for 12 hours. After the reaction was complete, a small amount of methanol was added to quench the reaction, the solvent was evaporated under reduced pressure, and the solution was extruded through a silica gel column using petroleum ether:dichloromethane (10:1) as the developing solvent to obtain compound A123-2.

[0139] Compound A123-2 (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. The mixture was then heated to 30 °C and stirred for another 1 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 A123 (21% yield, HPLC purity 99.22%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 921.43; Elemental analysis results: Theoretical values: C, 88.58; H, 5.69; B, 1.17; N, 4.56 (%); Experimental values: C, 88.58; H, 5.69; B, 1.18; N, 4.55 (%).

[0140] The synthesis methods of the following synthetic examples 13-33 are similar to those of examples 1-12 above, except that the polybrominated precursor in the first step is replaced with the corresponding polybrominated precursor.

[0141]

[0142]

[0143] The specific experimental results of synthesis examples 13-33 are as follows:

[0144]

[0145]

[0146] 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.

[0147] Device Examples

[0148] 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.

[0149] 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.

[0150] 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).

[0151] 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).

[0152] 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.

[0153] 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.

[0154] 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).

[0155] Specifically, the method for fabricating the organic electroluminescent device of the present invention includes the following steps:

[0156] 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.

[0157] 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.

[0158] 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.

[0159] 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;

[0160] 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.

[0161] 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;

[0162] 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;

[0163] 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.

[0164] 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.

[0165] The organic electroluminescent device of the present invention will be further described below through specific embodiments.

[0166] Device Example 1

[0167] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0168] ITO / HI(5nm) / HT(25nm) / EBL / (10nm) / Host:3wt%A1(25nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0169] 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 (10 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 (25 nm in this example); the hole blocking layer material is HBL, with a total thickness of 0-30 nm (10 nm in this example); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this example); and the electron injection layer and cathode materials are LiF (0.5 nm) and metallic aluminum (150 nm).

[0170] Device Example 2

[0171] The structure of the organic electroluminescent device prepared in this embodiment is shown below:

[0172] ITO / HI(5nm) / HT(25nm) / EBL / (10nm) / Host:30wt%TD:3wt%A1(25nm) / HBL(10nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0173] 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 (10 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 30 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 (25 nm in this example); the hole blocking layer material is HBL, with a total thickness of 0-30 nm (10 nm in this example); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this example); and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0174] Device Examples 1 and 2 are respectively non-sensitized and sensitized devices for dye A1.

[0175] Examples 3-66 of this invention are the same as those in 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:

[0176] Table 1:

[0177]

[0178]

[0179]

[0180] 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 (10 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 (25 nm in this embodiment); the hole blocking layer material is HBL, with a total thickness of 0-30 nm (10 nm in this embodiment); the electron transport layer material is ET, with a thickness of 5-300 nm (30 nm in this embodiment); the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0181] The structural formulas of the various organic materials used in the above embodiments are as follows:

[0182]

[0183]

[0184]

[0185] The performance of the devices prepared in Examples 1-66 and Comparative Examples 1-6 of this invention is shown in Table 2 below:

[0186] Table 2:

[0187]

[0188]

[0189]

[0190] 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.

[0191] 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 (LT90@10mA / cm) 2 This represents the time taken for the device brightness to decrease to 90% of its initial brightness, where the initial brightness is a current density of 10 mA / cm². 2 The corresponding brightness was obtained by testing using the OLED aging life test system of Shanghai University.

[0192] In Table 2, LT90@10mA / cm 2 The relative value of / h is the result obtained by comparing with Comparative Example 1.

[0193] The compounds of this invention introduce an adamantane lock structure on both sides of the classic boron-nitrogen core, connecting the two benzene rings, eliminating the original repulsion between hydrogen atoms, significantly enhancing molecular rigidity, further reducing the full width at half maximum (FWHM) (≤25nm), improving color purity, and consequently significantly improving the efficiency of the light-emitting device, providing guidance for constructing novel narrow-spectrum light-emitting materials. Simultaneously, due to the stereochemistry of the adamantane structure, it has significant steric hindrance, effectively increasing the intermolecular distance, thereby suppressing the disadvantages of efficiency reduction, spectral broadening, and decreased stability caused by molecular stacking. Furthermore, it can reduce the interaction between the host and dye, and between dyes, in the device, improving the device's luminous efficiency, lifetime, and other performance characteristics. Moreover, the adamantane lock structure has sp... 3 Hybridized carbon atoms offer better stability compared to heteroatom-locked structures with lone pairs of electrons, thus enabling the fabrication of highly efficient OLED devices.

[0194] Furthermore, when one of the rings A, B, C, and D in the compound of this invention is designed as a fused benzene ring structure, the conjugated planar structure of the molecule can be further broadened, thereby dispersing the electron density of the molecule, enhancing molecular stability, and improving device lifetime. Moreover, this enhancement and improvement occur with the increase of fused benzene structures in rings A, B, C, and D.

[0195] Compared to Comparative Examples 1-6, with other materials remaining the same in the organic electroluminescent device structure, Examples 1-66 showed improved efficiency, narrowed spectrum, and significantly increased device lifetime. This is mainly due to the introduction of an adamantane structure on both sides of the classic boron-nitrogen core, connecting the two benzene rings. This differs from the adamantane-locked structure in the comparative molecules, which contain only one adamantane. The bilateral adamantane structure significantly increases the intermolecular distance, thereby reducing intermolecular interactions and suppressing spectral broadening caused by molecular packing. Simultaneously, it reduces interactions between the host and dye, as well as between dyes, improving the device's luminous efficiency and lifetime. Furthermore, compared to the oxygen-bridged structure of the comparative molecule P3, the adamantane-locked structure has an sp-shaped connection site. 3 Hybridized carbon atoms exhibit better stability, thereby enabling the fabrication of highly efficient OLED devices. Therefore, when the compounds of this invention are used in electroluminescent devices, high luminous efficiency, narrow emission spectra, and long device lifetime are simultaneously achieved.

[0196] 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. 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.

[0197] 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.

[0198] 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): In formula (1), rings A, B, C, D, and E each independently represent one of the aromatic rings of C6 to C60 and the heteroaromatic rings of C5 to C60; W1, W2, and W3 are each independently selected from single bonds, O, CO, SO2, S, Se, NR1, CR2R3, or SiR4R5; m1, m2, and m3 are each independently 0 or 1; R1, R2, R3, R4, and R5 are either not connected to adjacent groups or are connected in a ring; R2 and R3 are either not connected to each other or are connected in a ring; R4 and R5 are either not connected to each other or are connected in a ring. R1, R2, R3, R4, and R5 are each independently selected from one of the following groups that are unsubstituted or R' substituted: C1-C36 chain alkyl, C3-C36 cycloalkyl, C6-C30 arylamino, C6-C60 aryl, C6-C60 aryloxy, and C5-C60 heteroaryl. The 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 fusion bond; 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, and C5-C60 heteroaryl; The two adjacent R's are either not connected or connected to form a ring; R' is selected from one or a combination of two 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, In equation (1), R a R b R c R d R e Each element is independently connected to the ring structure it is attached to via a single bond or a fused bond, preferably via a single bond; In equation (1), rings A, B, C, and D are each independently represented by the structure shown in equation (a), (b), or (c), and ring E is represented by the structure shown in equation (a). The dashed double bonds represent the fusion positions of the following groups in formula (1): any of the dashed double bonds (b1), (b2), and (b3) represents the fusion position of the group in formula (b), and any of the dashed double bonds (c1), (c2), and (c3) represents the fusion position of the group in formula (c). 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 or a combination of two of the following: 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 (1), at least one of rings A, B, C, and D is the structure shown in equation (c), and ring E is the structure shown in equation (a); Preferably, in formula (c), Z is selected from O, S, or NR. 1 ; 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, In formula (1), rings A, B, C, and D each independently represent one of the aromatic rings of C6 to C30 and the heteroaromatic rings of C5 to C30, and ring E independently represents an aromatic ring of C6 to C30. Preferably, ring A, ring B, ring C, and ring D are each independently selected from benzene ring, naphthyl ring, anthracene ring, fluorene ring, furan, benzofuran, dibenzofuran, indole, benzoindole, carbazole, indole-carbazole, benzothiophene, dibenzothiophene, thiophene, benzoanthrayl, phenanthrayl, pyrene, pyrene, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzopyrene, biphenyl, amphylphenyl, terphenyl, triphenyl, triphenyl, tetraphenyl, diphenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, isoindole The ring E is selected from any one of the following: carbazolyl, indocarbazolyl, pyridinyl, quinolinyl, isoquinolinyl, acridinel, phenanthridinel, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazolel, imidazolyl, benzimidazolel, naphthimidazolel, phenanthridinemidazolel, pyridinimidazolel, pyrazinimidazolel, quinoxalinimidazolel, oxazolyl, benzooxazolyl, naphthimidazolel, anthraquinoxazolyl, phenanthridinemidazolel, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, and quinoxalinyl; ring E is selected from a benzene ring. More preferably, ring A, ring B, ring C, and ring D are each independently selected from one of the following: benzene ring, naphthalene ring, anthracene ring, fluorene ring, furan, benzofuran, dibenzofuran, indole, benzoindole, carbazole, indole-carbazole, benzothiophene, dibenzothiophene, and thiophene; ring E is selected from the benzene ring.

5. The organic compound according to any one of claims 1-4, characterized in that, In formula (1): m3 is 0, and m1 and m2 are each independently 0 or 1; W1 and W2 are each independently selected from CC single bond, O, CO, SO2, S, NR1, CR2R3 or SiR4R5; Preferably, m3 is 0, and m1 and m2 are each independently 0 or 1; W1 and W2 are each independently selected from CC single bonds, CO, NR1 or CR2R3; More preferably, m3 is 0, and m1 and m2 are each independently 0 or 1; W1 and W2 are both selected from C-C single bonds.

6. The organic compound according to claim 2, 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 of W1, W2, m1, and m2 are the same as those in equation (1); Rings A, B, C, and D are each independently represented by the structure shown in equation (a) or equation (c); Preferably, m1 and m2 are both 1, W1 and W2 independently represent CC single bonds, CO, NR1 or CR2R3, R1, R2, and R3 are not connected to adjacent rings or are connected by single bonds; R2 and R3 are not connected or are connected to form a ring. Alternatively, preferably, one of m1 and m2 is 0 and the other is 1, W1 and W2 represent CC single bonds, CO, NR1 or CR2R3, R1, R2, and R3 are not connected to adjacent rings or are connected by single bonds; R2 and R3 are not connected or are connected to form a ring. More preferably, W1 and W2 represent CC single bonds, CO, NR1, or CR2R3, and R1, R2, and R3 are 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, thiophene, benzo[a]thiophene, isobenzo[a]thiophene, dibenzo[a]thiophene, pyrrole, isoindole, carbazole, indenecarbazole, and pyridyl. Quinolinyl, isoquinolinyl, pyrazolyl, indazoleyl, imidazolyl, pyridinyl, 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, indazolyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl or methoxy; More preferably, m1 and m2 are both 1, and W1 and W2 both represent CC single bonds.

7. The organic compound according to claim 6, characterized in that, It has the structure shown in equation (3-1): Among them, R a R b R c R d R e The definitions are the same as those in equation (1).

8. The organic compound according to any one of claims 1, 6, or 7, 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, C5-C30 heteroaryl; wherein 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 fusion bond; 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, isotrimerininyl, spirotrimerininyl, spiroisotrimerininyl, 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, naphthiazoleyl, phenanthreneimidazoleyl, pyridiniumimidazoleyl, pyrazinyl Imidazolyl, quinoxolinoimidazolyl, oxazolyl, benzoxoxazolyl, naphthoxazolyl, anthraquinoxazolyl, phenanthoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxolinyl, 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, phenthiazinyl, naphridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzoxazolyl Triazolyl, 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, indazinyl, benzothiadiazolyl, 9,9-dimethylacridyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl or methoxy; 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 fusion bond; 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, thiophene, benzo[a]thiophene, isobenzo[a]thiophene, dibenzo[a]thiophene, pyrrole, isoindole, carbazole, indoxacarbazole, pyridinyl, quinolinyl, isoquinolinyl, pyrazolyl, indazole, imidazolyl, pyridazine. The following are listed: 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, indazinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, or methoxy; The R a R b R c R d R e Each element is independently connected to the ring structure it is attached to via a single bond or a fused bond.

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

10. The application of the compound according to any one of claims 1-9 as a functional material in an organic electronic device, wherein the organic electronic device is an organic electroluminescent device, an optical sensor, a solar cell, an organic thin-film transistor, or an organic field-effect transistor; 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.

11. 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 a compound according to any one of claims 1-9.

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

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