Compound and application thereof

Abstract

The invention discloses a compound and application thereof. The compound has a general formula as shown in a formula (I): # imgabs0 #, in the formula (I), M1 and M2 are respectively and independently selected from substituted or unsubstituted C6-C60 aromatic rings and substituted or unsubstituted C3-C30 heteroaromatic rings; when M1 and M2 are both substituted or unsubstituted aromatic rings, at least one Z is N; i is an integer of 0-5, j is an integer of 0-5, and i + j > = 1. The compound disclosed by the invention has narrow emission performance, can obtain high luminous efficiency, luminous color purity and device service life when being applied to a luminescent device, and can obtain a high-resolution imaging effect when being applied to biological imaging.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic light-emitting materials, and particularly relates to a compound and its application. Background Art

[0002] Organic light-emitting materials have good luminescence performance, good tunability, relatively flexible molecular design, and can be coated on various substrates to form films. Therefore, they are widely used in fields such as organic light-emitting diodes (OLEDs), organic light-emitting field-effect transistors, organic photovoltaic devices, light-emitting electrochemical cells, photoelectric converters, switching devices, image sensors, lasers, photosensitive devices, bioimaging devices, coatings, organic laser devices, etc. Among them, in order to meet the requirements of high-definition OLED displays and bioimaging, new materials with a narrow full width at half maximum (FWHM) have gradually emerged. Therefore, it is necessary to develop new organic light-emitting materials to meet the growing demand for high-definition displays. Summary of the Invention

[0003] In view of this, the present invention provides a compound and its application, and this compound can be used as a light-emitting material for light-emitting devices.

[0004] The technical solution of the present invention is as follows:

[0005] In a first aspect of the present invention, a compound is provided, and the compound has a general formula as shown in formula (I):

[0006]

[0007] In formula (I), M1 and M2 each independently selected from substituted or unsubstituted C6-C 60 aryl ring, substituted or unsubstituted C3-C 30 heteroaryl ring; when M1 and M2 are both substituted or unsubstituted aryl rings, at least one Z is N;

[0008] i is an integer from 0 to 5, j is an integer from 0 to 5, and i + j ≥ 1;

[0009] Z is each independently C-R1 or N, and R1 is each independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a carboxyl group, a sulfonic acid group, a C1-C 30 acyl group, substituted or unsubstituted C1-C 30 alkyl group, substituted or unsubstituted C3-C 30 cycloalkyl group, substituted or unsubstituted C2-C 30 heterocycloalkyl group, substituted or unsubstituted C1-C 30 alkoxy group, substituted or unsubstituted C6-C30 Aryl, substituted or unsubstituted C3-C 30 Heteroaryl, substituted or unsubstituted C6-C 30 Aryloxy, substituted or unsubstituted C3-C 30 Heteroaryloxy, substituted or unsubstituted C1-C 30 Alkylamino, substituted or unsubstituted C6-C 30 Arylamino, substituted or unsubstituted C3-C 30 Heteroarylamino, substituted or unsubstituted B1-B 30 Boranyl, substituted or unsubstituted Si1-Si 30 Silyl, substituted or unsubstituted C6-C 30 Aromatic silyl, or a C1-C containing at least one heteroatom selected from O, N, S, B, P, F other than the above groups 18 An electron-withdrawing group, adjacent R1s are connected to form a ring or not connected;

[0010] R2 and R3 are each independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a carboxyl group, a sulfonic acid group, C1-C 30 Acyl, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C3-C 30 Cycloalkyl, substituted or unsubstituted C2-C 30 Heterocycloalkyl, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C3-C 30 Heteroaryl, substituted or unsubstituted C6-C 30 Aryloxy, substituted or unsubstituted C3-C 30 Heteroaryloxy, substituted or unsubstituted C1-C 30 Alkylamino, substituted or unsubstituted C6-C 30 Arylamino, substituted or unsubstituted C3-C 30 Heteroarylamino, substituted or unsubstituted B1-B 30 Boranyl, substituted or unsubstituted Si1-Si 30 Silyl, substituted or unsubstituted C6-C 30 Aromatic silyl, or a C1-C containing at least one heteroatom selected from O, N, S, B, P, F other than the above groups 18 An electron-withdrawing group.

[0011] In an embodiment of the present invention, the general formula shown in formula (I) is any one of the formulas (I-1) to (I-4) shown:

[0012]

[0013] The above different general formula structures can enrich the types of compounds and obtain various luminescent materials with good luminescent properties.

[0014] In an embodiment of the present invention, in the M1 ring and the M2 ring, the heteroatom in the heteroaromatic ring is selected from one or more of an oxygen atom, a sulfur atom, a nitrogen atom, and a selenium atom.

[0015] In an embodiment of the present invention, in the M1 ring and the M2 ring, the substituted or unsubstituted C6-C 60 The aromatic ring is a substituted or C6-C 30 aromatic ring; a suitable number of carbon atoms can not only endow the compound with good luminescent properties, but also make the raw materials more easily available and simplify the preparation of the compound.

[0016] In an embodiment of the present invention, in the M1 ring and the M2 ring, the substituted or unsubstituted C6-C 60 aromatic ring includes at least one of a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted biphenyl ring, a substituted or unsubstituted terphenyl ring, a substituted or unsubstituted binaphthalene ring, a substituted or unsubstituted fluorene ring, and a substituted or unsubstituted spirofluorene ring;

[0017] In an embodiment of the present invention, in the M1 ring and the M2 ring, the substituted or unsubstituted C3-C 30 heteroaromatic ring includes at least one of a substituted or unsubstituted pyrrole ring, a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted benzopyrrole ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted carbazole ring, a substituted or unsubstituted triazine ring, and a substituted or unsubstituted xanthenone ring.

[0018] Different aromatic rings can enrich the types of compounds and achieve more adjustments in luminescent properties.

[0019] In an embodiment of the present invention, in the M1 ring and the M2 ring, the substituents in the substituted C6-C 60 aromatic ring and the substituted C3-C 30 heteroaromatic ring include a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a carboxyl group, a sulfonic acid group, a C1-C 30 acyl group, a substituted or unsubstituted C1-C 30 alkyl group, a substituted or unsubstituted C3-C 30 cycloalkyl group, a substituted or unsubstituted C2-C 30 heterocycloalkyl group, and a substituted or unsubstituted C1-C 30Alkoxy, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C3-C 30 Heteroaryl, substituted or unsubstituted C6-C 30 Aryloxy, substituted or unsubstituted C3-C 30 Heteroaryloxy, substituted or unsubstituted C1-C 30 Alkylamino, substituted or unsubstituted C6-C 30 Arylamino, substituted or unsubstituted C3-C 30 Heteroarylamino, substituted or unsubstituted B1-B 30 Boranyl, substituted or unsubstituted Si1-Si 30 Silyl, substituted or unsubstituted C6-C 30 One or more of aromatic silyls. The introduction of different substituents can further adjust the luminescence performance to meet the requirements of more different scenarios.

[0020] In the embodiments of the present invention, the general formula shown in formula (I) is any one of the general formulas shown in formulas (II-1) to (II-12):

[0021]

[0022] In formulas (II-1) to (II-12), Z is independently C-R1 or N, X is independently O, S or N-R4, and R1, R2, R3, R4 are independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a carboxyl group, a sulfonic acid group, C1-C 30 Acyl, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C3-C 30 Cycloalkyl, substituted or unsubstituted C2-C 30 Heterocycloalkyl, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C3-C 30 Heteroaryl, substituted or unsubstituted C6-C 30 Aryloxy, substituted or unsubstituted C3-C 30 Heteroaryloxy, substituted or unsubstituted C1-C 30 Alkylamino, substituted or unsubstituted C6-C 30 Arylamino, substituted or unsubstituted C3-C 30 Heteroarylamino, substituted or unsubstituted B1-B 30 Boranyl, substituted or unsubstituted Si1-Si 30 Silyl, substituted or unsubstituted C6-C 30An aromatic silyl group, or a C1-C containing at least one heteroatom selected from O, N, S, B, P, and F other than the above groups 18 An electron-withdrawing group, and adjacent R1s may be connected to form a ring or not; R4 may be connected to adjacent R1s to form a ring or not;

[0023] In formulas (II-2), (II-5), (II-9), and (II-12), at least one Z is N. The above general formula structure can achieve good conjugation effects, obtain good luminescence properties, and the above structure is relatively symmetric, which can better realize the preparation.

[0024] In the embodiments of the present invention, the substituted C1-C 30 alkyl group, substituted C3-C 30 cycloalkyl group, substituted C2-C 30 heterocycloalkyl group, substituted C1-C 30 alkoxy group, substituted C6-C 30 aryl group, substituted C3-C 30 heteroaryl group, substituted C6-C 30 aryloxy group, substituted C3-C 30 heteroaryloxy group, substituted C1-C 30 alkylamino group, substituted C6-C 30 arylamino group, substituted C3-C 30 heteroarylamino group, substituted B1-B 30 boranyl group, substituted Si1-Si 30 silyl group, substituted C6-C 30 The substituents in the aromatic silyl group include deuterium atom, tritium atom, halogen atom, cyano group, nitro group, hydroxyl group, carboxyl group, sulfonic acid group, C1-C 30 acyl group, C1-C 30 alkyl group, C3-C 30 cycloalkyl group, C2-C 30 heterocycloalkyl group, C1-C 30 alkoxy group, C6-C 30 aryl group, C3-C 30 heteroaryl group, C6-C 30 aryloxy group, C3-C 30 heteroaryloxy group, C1-C 30 alkylamino group, C6-C 30 arylamino group, C3-C 30 heteroarylamino group, B1-B 30 boranyl group, Si1-Si 30 silyl group, C6-C 30 One or more of the aromatic silyl groups. The introduction of different substituents can obtain compounds with more structures and further adjust the properties of the compounds.

[0025] In the second aspect of the present invention, there is provided the use of the above-mentioned compound and its salt in an electroluminescent device, an organic light-emitting field-effect transistor, an organic photovoltaic device, a light-emitting electrochemical cell, an optoelectronic converter, an optical switch device, an image sensor, a laser, a photosensitive device, a bioimaging device, a coating, and an organic laser device.

[0026] In the third aspect of the present invention, there is provided a light-emitting layer, and the light-emitting layer comprises the above-mentioned compound.

[0027] In an embodiment of the present invention, the light-emitting layer comprises a host material and a doping material, and the doping material comprises the compound.

[0028] In the fourth aspect of the present invention, there is provided an electronic device, and the electronic device comprises the above-mentioned compound; or comprises the above-mentioned light-emitting layer.

[0029] In an embodiment of the present invention, the electronic device comprises a cathode and an anode, and a functional layer located between the cathode and the anode, and the functional layer comprises the compound.

[0030] In an embodiment of the present invention, the electronic device comprises an electroluminescent device, an organic light-emitting field-effect transistor, an organic photovoltaic device or a light-emitting electrochemical cell.

[0031] In the fifth aspect of the present invention, there is provided a display device, and the display device comprises the above-mentioned electronic device; or comprises the above-mentioned light-emitting layer.

[0032] In the sixth aspect of the present invention, there is provided an electronic device, and the electronic device comprises the above-mentioned display device; or comprises the above-mentioned electronic device.

[0033] In the seventh aspect of the present invention, there is provided a lighting device, and the lighting device comprises the above-mentioned electronic device; or comprises the above-mentioned light-emitting layer.

[0034] Compared with the prior art, the present invention has the following beneficial effects:

[0035] (1) The compound of the present invention has the performance of narrow emission. When applied in a light-emitting device, high luminous efficiency, luminous color purity and device lifetime can be obtained. When applied in bioimaging, a high-resolution imaging effect can be obtained.

[0036] (2) The preparation method of the compound of the present invention is simple and the cost is low. Description of the Drawings

[0037] Figure 1 It is the fluorescence spectrum of formula (251) prepared in Example 1 of the present invention.

[0038] Figure 2 It is the fluorescence spectrum of formula (288) prepared in Example 2 of the present invention.

[0039] Figure 3 This is the single crystal structure diagram of the formula (288) prepared in Example 2 of the present invention.

[0040] Figure 4 This is the fluorescence spectrum of the formula (226) prepared in Example 3 of the present invention.

[0041] Figure 5 This is the single crystal structure diagram of the formula (226) prepared in Example 3 of the present invention.

[0042] Figure 6 This is the fluorescence spectrum of the formula (552) prepared in Example 4 of the present invention.

[0043] Figure 7 This is the single crystal structure diagram of the formula (552) prepared in Example 4 of the present invention. Detailed implementation manners

[0044] The following will specifically introduce the above compound, which has a general formula as shown in formula (I):

[0045]

[0046] In formula (I), M1 and M2 are each independently selected from a substituted or unsubstituted C6-C 60 aryl ring, a substituted or unsubstituted C3-C 30 heteroaryl ring; when M1 and M2 are both a substituted or unsubstituted aryl ring, at least one Z is N; M1 and M2 are in a structure of fused rings;

[0047] i is an integer from 0 to 5, j is an integer from 0 to 5, and i + j ≥ 1;

[0048] Z is each independently C-R1 or N, and R1 is each independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a carboxyl group, a sulfonic acid group, a C1-C 30 acyl group, a substituted or unsubstituted C1-C 30 alkyl group, a substituted or unsubstituted C3-C 30 cycloalkyl group, a substituted or unsubstituted C2-C 30 heterocycloalkyl group, a substituted or unsubstituted C1-C 30 alkoxy group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C3-C 30 heteroaryl group, a substituted or unsubstituted C6-C 30 aryloxy group, a substituted or unsubstituted C3-C 30 heteroaryloxy group, a substituted or unsubstituted C1-C 30 alkylamino group, a substituted or unsubstituted C6-C 30 arylamino group, a substituted or unsubstituted C3-C30 Heteroarylamino, substituted or unsubstituted B1 - B 30 Boranyl, substituted or unsubstituted Si1 - Si 30 Silyl, substituted or unsubstituted C6 - C 30 Arylsilyl, or a C1 - C containing at least one heteroatom selected from O, N, S, B, P, F other than the above groups 18 electron-withdrawing group, adjacent R1s are connected to form a ring or not;

[0049] R2 and R3 are each independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a carboxyl group, a sulfonic acid group, C1 - C 30 acyl group, substituted or unsubstituted C1 - C 30 alkyl group, substituted or unsubstituted C3 - C 30 cycloalkyl group, substituted or unsubstituted C2 - C 30 heterocycloalkyl group, substituted or unsubstituted C1 - C 30 alkoxy group, substituted or unsubstituted C6 - C 30 aryl group, substituted or unsubstituted C3 - C 30 heteroaryl group, substituted or unsubstituted C6 - C 30 aryloxy group, substituted or unsubstituted C3 - C 30 heteroaryloxy group, substituted or unsubstituted C1 - C 30 alkylamino group, substituted or unsubstituted C6 - C 30 arylamino group, substituted or unsubstituted C3 - C 30 heteroarylamino, substituted or unsubstituted B1 - B 30 boranyl, substituted or unsubstituted Si1 - Si 30 silyl, substituted or unsubstituted C6 - C 30 arylsilyl, or a C1 - C containing at least one heteroatom selected from O, N, S, B, P, F other than the above groups 18 electron-withdrawing group.

[0050] In the embodiments of the present invention, in formula (I), multiple Zs may be the same or different groups; when multiple Zs are all represented as C-R1, R1 may be a group with the same structure or different structures each time it appears. That is, Zs at different positions may have the same structure or different structures. Specifically, all Zs at all positions may be the same, or all Zs at all positions may be different, or Zs at some positions may be the same. For example, in some embodiments, in formula (I), all Zs are C(H); or some Zs are C(H) and the remaining Zs are C-CH3; or some Zs are C(H) and the remaining Zs are C-C(CH3)3; or some Zs are C(H) and the remaining Zs are C-C6H5; or some Zs are C(H) and the remaining Zs are C-C6H4-C(CH3)3; or some Zs are C(H) and the remaining Zs are C-C6H4-CH3; or some Zs are C(H) and the remaining Zs are C-C5H4N.

[0051] For the compound provided by the present invention, its molecular skeleton is obtained by ring closure of a bicyclic aromatic ring or bicyclic aromatic heterocycle with an o-phenylenediamine group and a bicyclic aromatic ring or bicyclic aromatic heterocycle with o-phenylenediamine or o-phenylenedichloro or o-phenylenedihydroxy or o-phenyldibromo or o-phenyldiiodo to obtain an anti-aromatic reduced phenazine derivative polycyclic aromatic hydrocarbon skeleton, and R2 and R3 are introduced through a C-N coupling reaction to increase steric hindrance. This molecular skeleton structure has high stability, is easy to synthesize, and has strong structural modifiability; the polycyclic unit of the compound molecular skeleton has a rigid skeleton structure and anti-aromatic properties, which can inhibit low-frequency, medium-frequency, and high-frequency vibrations in the excited state, so that a narrower FWHM can be generated; this compound can achieve a spectrum in the blue light region. Since the phenazine skeleton is between sp 2 and sp 3 hybridized N atom folding effect, the rigidity of this compound is further enhanced after aggregation; at the same time, due to the steric hindrance effect brought by R2 and R3, the formation of strong π-π interactions in the aggregated state of this compound is effectively avoided, so that such compounds show a narrower FWHM in the aggregated state. When this compound is used as a luminescent material in a light-emitting device, high luminous efficiency, luminous color purity, and device lifetime can be obtained. When this compound is used as a luminescent material in biological imaging, a high-resolution imaging effect can be obtained. By introducing various substituents to the comparative molecular skeleton in this application, the adjustment of the luminescence position and FWHM can be further realized, compounds with more diverse structures can be obtained, and the application range can be expanded. Among them, the "full width at half maximum" refers to the peak width at half of the peak height in the electroluminescence spectrum of the luminescent material.

[0052] In the embodiments of the present invention, the general formula shown in formula (I) is any one of the formulas shown in formula (I-1) to formula (I-4):

[0053]

[0054] In Formula (I-1) to Formula (I-4), M1, M2, Z, R2, and R3 are the same as those in Formula (I).

[0055] In an embodiment of the present invention, in the M1 ring and the M2 ring, the heteroatom in the heteroaromatic ring can be one or more selected from an oxygen atom, a sulfur atom, a nitrogen atom, and a selenium atom.

[0056] In an embodiment of the present invention, in the M1 ring and the M2 ring, the substituted C6-C 60 aromatic ring, the substituted C3-C 30 heteroaromatic ring substituents include a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a carboxyl group, a sulfonic acid group, a C1-C 30 acyl group, a substituted or unsubstituted C1-C 30 alkyl group, a substituted or unsubstituted C3-C 30 cycloalkyl group, a substituted or unsubstituted C2-C 30 heterocycloalkyl group, a substituted or unsubstituted C1-C 30 alkoxy group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C3-C 30 heteroaryl group, a substituted or unsubstituted C6-C 30 aryloxy group, a substituted or unsubstituted C3-C 30 heteroaryloxy group, a substituted or unsubstituted C1-C 30 alkylamino group, a substituted or unsubstituted C6-C 30 arylamino group, a substituted or unsubstituted C3-C 30 heteroarylamino group, a substituted or unsubstituted B1-B 30 boranyl group, a substituted or unsubstituted Si1-Si 30 silyl group, a substituted or unsubstituted C6-C 30 one or more of an aromatic silyl group.

[0057] In the embodiments of the present invention, the M1 ring and the M2 ring are each independently selected from a benzene ring, a deuterated benzene ring, a tritiated benzene ring, a methyl-substituted benzene ring, an ethyl-substituted benzene ring, an isopropyl-substituted benzene ring, a tert-butyl-substituted benzene ring, a deuterated methyl-substituted benzene ring, a deuterated ethyl-substituted benzene ring, a deuterated isopropyl-substituted benzene ring, a deuterated tert-butyl-substituted benzene ring, a cyano-substituted benzene ring, an adamantyl-substituted benzene ring, a pyridyl-substituted benzene ring, a naphthalene ring, a deuterated naphthalene ring, a tritiated naphthalene ring, an alkyl-substituted naphthalene ring, a deuterated alkyl-substituted naphthalene ring, a tritiated alkyl-substituted naphthalene ring, an anthracene ring, a deuterated anthracene ring, a tritiated anthracene ring, an alkyl-substituted anthracene ring, a deuterated alkyl-substituted anthracene ring, a tritiated alkyl-substituted anthracene ring, a phenanthrene ring, a deuterated phenanthrene ring, a tritiated phenanthrene ring, an alkyl-substituted phenanthrene ring, a deuterated alkyl-substituted phenanthrene ring, a tritiated alkyl-substituted phenanthrene ring, a biphenyl ring, a deuterated biphenyl ring, a tritiated biphenyl ring, a methyl-substituted biphenyl ring, an ethyl-substituted biphenyl ring, an isopropyl-substituted biphenyl ring, a tert-butyl-substituted biphenyl ring, a deuterated methyl-substituted biphenyl ring, a deuterated ethyl-substituted biphenyl ring, a deuterated isopropyl-substituted biphenyl ring, a deuterated tert-butyl-substituted biphenyl ring, a terphenyl ring, a deuterated terphenyl ring, a tritiated terphenyl ring, a pyridine ring, a phenyl-substituted pyridine ring, a quinoline ring, a furan ring, a methyl-substituted furan ring, a phenyl-substituted furan ring, a thiophene ring, a methyl-substituted thiophene ring, a phenyl-substituted thiophene ring, a pyrrole ring, a methyl-substituted pyrrole ring, a phenyl-substituted pyrrole ring, a benzothiophene ring, a benzofuran ring, a methyl-substituted benzofuran ring, a carbazole ring, or any one of them.

[0058] In the embodiments of the present invention, in formulas (I-1) to (I-4), the two M1s may have the same structure or different structures; the two M2s may have the same structure or different structures. The plurality of Zs may be the same or different groups; when the plurality of Zs are all represented as C-R1, R1 may be a group with the same structure or different structures each time it appears. That is, the Zs at different positions may have the same structure or different structures, specifically, all the Zs at all positions may be the same, or all the Zs at all positions may be different, or some of the Zs at some positions may be the same.

[0059] In the embodiments of the present invention, the general formula shown in formula (I) may specifically be any one of the formulas shown in formulas (II-1) to (II-12):

[0060]

[0061] In formulas (II-1) to (II-12), Z is independently C-R1 or N, X is independently O, S or N-R4, and R1, R2, R3, and R4 are each independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a carboxyl group, a sulfonic acid group, a C1-C 30 acyl group, a substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C2-C 30 heterocycloalkyl, substituted or unsubstituted C1-C 30 alkoxy, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl, substituted or unsubstituted C6-C 30 aryloxy, substituted or unsubstituted C3-C 30 heteroaryloxy, substituted or unsubstituted C1-C 30 alkylamino, substituted or unsubstituted C6-C 30 arylamino, substituted or unsubstituted C3-C 30 heteroarylamino, substituted or unsubstituted B1-B 30 boranyl, substituted or unsubstituted Si1-Si 30 silyl, substituted or unsubstituted C6-C 30 aromatic silyl, or a C1-C containing at least one heteroatom selected from O, N, S, B, P, F other than the above groups 18 electron-withdrawing group, adjacent R1s are connected to form a ring or not; R4 is connected to adjacent R1s to form a ring or not;

[0062] In formulas (II-2), (II-5), (II-9) and (II-12), at least one Z is N.

[0063] In the embodiments of the present invention, in formulas (II-1) to (II-12), in the structure containing X, the two Xs can be the same or different. For example, the two Xs can both be O, or both be S, or both be N-R4. The multiple Zs can be the same or different groups; when the multiple Zs are all represented as C-R1, R1 can be a group with the same structure or different structures each time it appears. That is, the Zs at different positions can have the same structure or different structures. Specifically, all the Zs at all positions can be the same, or all the Zs at all positions can be different, or some of the Zs at some positions are the same.

[0064] In the embodiments of the present invention, the substituted C1-C 30 alkyl, substituted C3-C 30 cycloalkyl, substituted C2-C 30 heterocycloalkyl, substituted C1-C 30 alkoxy, substituted C6-C 30 aryl, substituted C3-C 30 heteroaryl, substituted C6-C 30 aryloxy, substituted C3-C 30 heteroaryloxy, substituted C1-C30 Alkylamino, substituted C6-C 30 Arylamino, substituted C3-C 30 Heteroarylamino, substituted B1-B 30 Boranyl, substituted Si1-Si 30 Silyl, substituted C6-C 30 The substituents in the aromatic silyl include deuterium atom, tritium atom, halogen atom, cyano group, nitro group, hydroxyl group, carboxyl group, sulfonic acid group, C1-C 30 Acyl group, C1-C 30 Alkyl group, C3-C 30 Cycloalkyl group, C2-C 30 Heterocycloalkyl group, C1-C 30 Alkoxy group, C6-C 30 Aryl group, C3-C 30 Heteroaryl group, C6-C 30 Aryloxy group, C3-C 30 Heteroaryloxy group, C1-C 30 Alkylamino, C6-C 30 Arylamino, C3-C 30 Heteroarylamino, B1-B 30 Boranyl, Si1-Si 30 Silyl, C6-C 30 One or more of the aromatic silyls.

[0065] In the embodiments of the present invention, the heteroatoms in the substituted or unsubstituted heterocycloalkyl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted heteroaryloxy group, and substituted or unsubstituted heteroarylamino group can be one or more selected from oxygen atom, sulfur atom, nitrogen atom, and selenium atom.

[0066] In the embodiments of the present invention, the above-mentioned substituted or unsubstituted alkyl group is a chain alkyl group, which can be a straight-chain alkyl group or a branched-chain alkyl group. The substituted or unsubstituted alkyl group can be a substituted or unsubstituted C1-C 30 Alkyl group. In some embodiments, the substituted or unsubstituted alkyl group can be a substituted or unsubstituted C1-C 20 Chain alkyl group, substituted or unsubstituted C1-C 10 Chain alkyl group, substituted or unsubstituted C1-C6 chain alkyl group. Specifically, for example, it can be a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted n-propyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted n-butyl group, a substituted or unsubstituted isobutyl group, a substituted or unsubstituted tert-butyl group, etc. Exemplarily, the substituted alkyl group can be deuterated methyl, tritiated methyl, fluoroethyl, fluoropropyl, trifluoromethyl, deuterated ethyl, tritiated ethyl, deuterated isopropyl, tritiated isopropyl, deuterated tert-butyl, tritiated tert-butyl, etc.

[0067] In the embodiments of the present invention, the above-mentioned substituted or unsubstituted cycloalkyl group may be a substituted or unsubstituted C3-C 30 cycloalkyl group. In some embodiments, the substituted or unsubstituted cycloalkyl group may be a substituted or unsubstituted C4-C 12 cycloalkyl group, a substituted or unsubstituted C5-C6 cycloalkyl group. Specifically, for example, it may be a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, etc. Exemplarily, the substituted cycloalkyl group may be a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, etc.

[0068] In the embodiments of the present invention, the above-mentioned substituted or unsubstituted heterocycloalkyl group may be a substituted or unsubstituted C2-C 30 heterocycloalkyl group. In some embodiments, the substituted or unsubstituted heterocycloalkyl group may be a substituted or unsubstituted C4-C 12 heterocycloalkyl group, a substituted or unsubstituted C5-C6 heterocycloalkyl group. Exemplarily, the substituted or unsubstituted heterocycloalkyl group may be a substituted or unsubstituted aziridine, a substituted or unsubstituted azetidine, a substituted or unsubstituted pyrrolidine.

[0069] In the embodiments of the present invention, the above-mentioned substituted or unsubstituted aryl group may be a substituted or unsubstituted C6-C 30 aryl group; the substituted or unsubstituted aryl group may be a substituted or unsubstituted C6-C 30 aryl group, and the aryl group may be a monocyclic aryl group or a polycyclic aryl group. In some embodiments, the substituted or unsubstituted aryl group may be a substituted or unsubstituted C6-C 20 aryl group, a substituted or unsubstituted C6-C 12Aryl. Among them, the substituted or unsubstituted monocyclic aryl can be, for example, phenyl, deuterated phenyl, tritiated phenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, etc. Among them, the polycyclic aryl can be a fused-ring type or a non-fused-ring type (such as biphenyls). Specifically, the substituted or unsubstituted polycyclic aryl of biphenyls can be, but is not limited to, substituted or unsubstituted biphenyl, terphenyl, diphenyl ether group (two benzene rings connected by an oxygen atom). Among them, exemplarily, the substituted polycyclic aryl can be deuterated biphenyl, tritiated biphenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, deuterated terphenyl, tritiated terphenyl, methyl-substituted diphenyl ether group, etc. The substituted or unsubstituted polycyclic aryl of the fused-ring type can be substituted or unsubstituted naphthyl, anthryl, phenanthryl, pyrenyl, fluorenyl, spirofluorene, 9,9-dimethylfluorene, binaphthyl, binaphthylfluorene, etc.

[0070] In the embodiments of the present invention, the above-mentioned substituted or unsubstituted aryloxy can be substituted or unsubstituted C6-C 30 Aryloxy; the aryloxy can be a monocyclic aryloxy or a polycyclic aryloxy. In some embodiments, the substituted or unsubstituted aryloxy can be substituted or unsubstituted C6-C 20 Aryloxy, substituted or unsubstituted C6-C 12 Aryloxy. Specifically, it can be the aryloxy obtained by oxidizing the above-mentioned aryl, for example, the phenoxy obtained by oxidizing phenyl, and so on for others, which will not be elaborated here.

[0071] In the embodiments of the present invention, the above-mentioned substituted or unsubstituted heteroaryl can be substituted or unsubstituted C3-C 30 Heteroaryl. In some embodiments, the substituted or unsubstituted heteroaryl can be substituted or unsubstituted C5-C 20 Heteroaryl, substituted or unsubstituted C6-C 12 Heteroaryl. The heteroatoms in the heteroaryl can be selected from one or more of N, O, S, and Se atoms. The substituted or unsubstituted heteroaryl can be a substituted or unsubstituted five-membered heterocycle, a substituted or unsubstituted six-membered heterocycle, a substituted or unsubstituted benzheterocycle, a substituted or unsubstituted heterocycle-fused heterocycle, etc. Exemplarily, the substituted or unsubstituted heteroaryl can be pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, benzofuryl, dibenzofuryl, tert-butyl-substituted dibenzofuryl, thienyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, xanthenone group, triazinyl, phenyl-substituted triazinyl, etc.

[0072] In the embodiments of the present invention, the above-mentioned substituted or unsubstituted heteroaryloxy may be a substituted or unsubstituted C3-C 30 heteroaryloxy. In some embodiments, the substituted or unsubstituted heteroaryloxy may be a substituted or unsubstituted C5-C 20 heteroaryloxy, a substituted or unsubstituted C6-C 12 heteroaryloxy. The heteroatom in the heteroaryloxy may be selected from one or more of N, O, S, and Se atoms. Specifically, the heteroaryloxy may be obtained by oxidizing the above-mentioned heteroaryl, which will not be elaborated here.

[0073] In the embodiments of the present invention, the substituted or unsubstituted alkylamino is an amino group substituted by a substituted or unsubstituted alkyl. The substituted or unsubstituted alkylamino may be a substituted or unsubstituted C1-C 30 alkylamino. In some embodiments, the substituted or unsubstituted alkylamino may be a substituted or unsubstituted C2-C 20 alkylamino, a substituted or unsubstituted C3-C 12 alkylamino. Exemplarily, the substituted or unsubstituted alkylamino may be ethylamino, etc.

[0074] In the embodiments of the present invention, the substituted or unsubstituted arylamino is an amino group substituted by a substituted or unsubstituted aryl, specifically, it may be an amino group substituted by the above-mentioned substituted or unsubstituted aryl. The substituted or unsubstituted arylamino may be a substituted or unsubstituted C6-C 30 arylamino. In some embodiments, the substituted or unsubstituted arylamino may be a substituted or unsubstituted C6-C 20 arylamino, a substituted or unsubstituted C7-C 15 arylamino. Exemplarily, the substituted or unsubstituted arylamino may be phenylamino, dimethylphenylamino, tert-butylbenzene-substituted amino, di-tert-butylphenylamino, etc.

[0075] In the embodiments of the present invention, the above-mentioned substituted or unsubstituted heteroarylamino is an amino group substituted by a substituted or unsubstituted heteroaryl, specifically, it may be an amino group substituted by the above-mentioned substituted or unsubstituted heteroaryl. The substituted or unsubstituted heteroarylamino may be a substituted or unsubstituted C3-C 30 heteroarylamino. In some embodiments, the substituted or unsubstituted heteroarylamino may be a substituted or unsubstituted C5-C 20 heteroarylamino, a substituted or unsubstituted C6-C 12 heteroarylamino.

[0076] In the embodiments of the present invention, the above-mentioned substituted or unsubstituted boranyl groups may be boranyl groups, phenyl-substituted boranyl groups, etc. In the substituted boranyl groups, the substituents may be deuterium atoms, tritium atoms, halogen atoms, cyano groups, nitro groups, hydroxyl groups, carboxyl groups, sulfonic acid groups, acyl groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups, etc.

[0077] In the embodiments of the present invention, the substituted or unsubstituted silyl groups may be trimethylsilyl groups, etc. In the embodiments of the present application, the substituted or unsubstituted aromatic silyl groups may be phenylsilyl groups, etc.

[0078] In the embodiments of the present invention, the C1-C containing at least one heteroatom of O, N, S, B, P, F other than the above-mentioned groups 18 electron-withdrawing groups may include but are not limited to substituted or unsubstituted imide groups, substituted or unsubstituted amide groups. Among them, the substituents in the substituted imide groups and substituted amide groups may be but are not limited to deuterium atoms, tritium atoms, halogen atoms, cyano groups, nitro groups, hydroxyl groups, carboxyl groups, sulfonic acid groups, acyl groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups.

[0079] In the embodiments of the present invention, each occurrence of R1, R2, R3, and R4 can independently be a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a tritiated methyl group, a fluoropropyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a phenyl-substituted tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a tritiated phenyl group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a terphenyl group, a deuterated terphenyl group, a tritiated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a tert-butyl-substituted dibenzofuryl group, a carbazolyl group, an N-phenylcarbazolyl group, a tert-butyl-substituted carbazolyl group, a tert-butyl-substituted N-carbazolylphenyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a biphenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl group, an xanthone group, a triazine group, a phenyl-substituted triazine group, a boranyl group, a phenyl-substituted boranyl group, a methoxy group, or a tert-butoxy group.

[0080] In some embodiments of the present invention, some adjacent R1s are connected to form a ring, and the remaining R1s can independently be selected from the above optional groups. Among them, when adjacent R1s are connected to form a ring (i.e., adjacent Zs are connected to form a ring), the formed ring structure includes but is not limited to any one of the structures shown in formulas (a) to (d):

[0081]

[0082] In formulas (a) to (d), the position marked with * is the connection position, and the structures of formulas (a) to (d) are connected to the molecular backbone in a fused-ring manner through the position marked with *.

[0083] In the embodiments of the present invention, the compound can specifically include but is not limited to any one of the compounds shown in the structural formulas such as formulas (1)-(583):

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119] The compounds provided by the present invention can be prepared in various chemically achievable ways. The raw materials for preparation can be o-phenylenediamine or o-phenylenedichloride or o-phenyldibromide or o-phenylenedihydroxy or o-phenyldiiodo containing the M1 ring and the M2 ring. The specific reaction process can be that first, ring closure occurs between o-phenylenediamine containing the M1 ring and the M2 ring and o-phenylenediamine or o-phenylenedichloride or o-phenyldibromide or o-phenylenedihydroxy or o-phenyldiiodo or o-phenylenediamine containing the M1 ring and the M2 ring, and then substitution reactions occur at the reduced phenazine N-terminus to introduce R2 and R3. The o-phenylenediamine or o-phenylenedichloride or o-phenyldibromide or o-phenylenedihydroxy or o-phenyldiiodo of the M1 ring and the M2 ring can have the following structures:

[0120]

[0121] Among them, the selection of Z is consistent with the previous text. The synthesis process of the present invention is simple, with a high yield and is easy to scale up production.

[0122] The above compounds provided by the present invention have high structural stability, high fluorescence quantum yield, and narrow full width at half maximum, and can be used in various electronic devices with functions such as light emission, display, and lighting to improve device efficiency, light emission color purity, and device life. The compounds of the present invention can be obtained through a relatively simple synthesis route, and the synthesis can be achieved without using dangerous chemicals such as butyllithium, which is suitable for industrial production and has good application effects and industrialization prospects in the fields of OLED lighting or OLED display.

[0123] The following further illustrates the implementation manners of the present invention through examples.

[0124] Example 1

[0125] Synthesis of the compound with the structural formula of (251) (hereinafter referred to as Compound 1):

[0126] (1) Add raw material A-1 (10 mmol) and B-1 (10 mmol) into a flask, then displace the nitrogen, and stir at 180 °C for 1 h. After the reaction is completed, cool to room temperature, wash three times with absolute ethanol and acetone, and dry in a vacuum drying oven to obtain intermediate a-1.

[0127] (2) Add intermediate a-1 (10 mmol) into a flask, and successively add raw material C-1 (25 mmol), Pd2(dba)3 (0.5 mmol), t-BuPHBF4 (1 mmol), t-BuONa (4 mmol) and toluene (50 mL), then displace the nitrogen, and stir at 120 °C for 1 h. Then directly evaporate to dryness, add tetrahydrofuran and water, ultrasonicate and then filter by suction, and wash three times with water to obtain a filter cake. Dissolve the filter cake in dichloromethane, evaporate to dryness and concentrate, and separate by silica gel chromatography to obtain compound 1.

[0128] The reaction process of the above synthesis process is as follows:

[0129]

[0130] The measured value of HRMS (high-resolution mass spectrometry) of compound 1: 443.1229 ([M+H]+), the theoretical value: 443.1325.

[0131] Example 2

[0132] Synthesis of the compound with the structural formula of formula (288) (hereinafter referred to as compound 2):

[0133] (1) Add raw material A-1 (20 mmol) into a flask, then displace the nitrogen, and stir at 180 °C for 1 h. After the reaction is completed, cool to room temperature, wash three times with absolute ethanol and acetone, and dry in a vacuum drying oven to obtain intermediate a-2.

[0134] (2) Add intermediate a-2 (10 mmol) into a flask, and successively add raw material C-1 (25 mmol), Pd2(dba)3 (0.5 mmol), t-BuPHBF4 (1 mmol), t-BuONa (4 mmol) and toluene (50 mL), then displace the nitrogen, and stir at 120 °C for 1 h. Then directly evaporate to dryness, add tetrahydrofuran and water, ultrasonicate and then filter by suction, and wash three times with water to obtain a filter cake. Dissolve the filter cake in dichloromethane, evaporate to dryness and concentrate, and separate by silica gel chromatography to obtain compound 2.

[0135] The reaction process of the above synthesis process is as follows:

[0136]

[0137] HRMS (High Resolution Mass Spectrometry) measurement value of Compound 2: 443.0789 ([M+H]+), theoretical value: 451.0795. The single crystal structure diagram is as shown in Figure 3 .

[0138] Example 3

[0139] Synthesis of the compound with the structural formula of (226) (hereinafter referred to as Compound 3):

[0140] (1) Add raw material A-2 (10 mmol) and raw material B-2 (10 mmol) into a flask. Then displace the nitrogen, add 60 mL of absolute ethanol, and stir at 80 °C for 2 days. After the reaction is completed, cool to room temperature, wash three times with absolute ethanol, and dry in a vacuum drying oven to obtain intermediate a-2;

[0141] (2) Add intermediate a-2 (10 mmol) and Na2S2O4 (40 mmol) into a flask. Then displace the nitrogen, add 100 mL of absolute ethanol and 200 mL of deionized water, and stir at 80 °C for 4 h. After the reaction is completed, cool to room temperature, wash three times with absolute ethanol and deionized water, and dry in a vacuum drying oven to obtain intermediate a-3;

[0142] (3) Add intermediate a-3 (10 mmol) into a flask, successively add raw material C-1 (40 mmol), Pd2(dba)3 (0.5 mmol), t-BuPHBF4 (1 mmol), t-BuONa (4 mmol) and toluene (50 mL). Then displace the nitrogen and stir at 120 °C for 1 h. Then directly evaporate to dryness, add tetrahydrofuran and water, ultrasonicate and filter, wash three times with water to obtain a filter cake. Dissolve the filter cake in dichloromethane, evaporate to dryness and concentrate, and separate by silica gel chromatography to obtain Compound 3.

[0143] The reaction process of the above synthesis process is as follows:

[0144]

[0145] HRMS (High Resolution Mass Spectrometry) measurement value of Compound 3: 613.2406 ([M+H]+), theoretical value: 613.2387. The single crystal structure diagram is as shown in Figure 5 .

[0146] Example 4

[0147] Synthesis of the compound with the structural formula of (552) (hereinafter referred to as Compound 4):

[0148] (1) Add raw material A-2 (10 mmol) and raw material B-2 (10 mmol) into a flask. Subsequently, displace the nitrogen, add 60 mL of absolute ethanol, and stir at 80 °C for 2 days. After the reaction is completed, cool to room temperature, wash three times with absolute ethanol, and dry in a vacuum drying oven to obtain intermediate a-2.

[0149] (2) Add intermediate a-2 (10 mmol) and Na2S2O4 (40 mmol) into a flask. Subsequently, displace the nitrogen, add 100 mL of absolute ethanol and 200 mL of deionized water, and stir at 80 °C for 4 h. After the reaction is completed, cool to room temperature, wash three times with absolute ethanol and deionized water, and dry in a vacuum drying oven to obtain intermediate a-3.

[0150] (3) Add intermediate a-3 (10 mmol) into a flask, and successively add raw material C-1 (25 mmol), Pd2(dba)3 (0.5 mmol), t-BuPHBF4 (1 mmol), t-BuONa (4 mmol) and toluene (50 mL). Subsequently, displace the nitrogen and stir at 120 °C for 1 h. Then directly evaporate to dryness under reduced pressure, add tetrahydrofuran and water, ultrasonicate and then filter by suction, and wash three times with water to obtain a filter cake. Dissolve the filter cake in dichloromethane, evaporate to dryness and concentrate, and separate by silica gel column chromatography to obtain compound 4.

[0151] The reaction process of the above synthesis process is as follows:

[0152]

[0153] The measured value of HRMS (high-resolution mass spectrometry) of compound 4: 537.2090 ([M+H]+), the theoretical value: 537.2074. The single crystal structure diagram is as Figure 7 .

[0154] Perform spectral tests on the compounds prepared in Examples 1 to 4 above. The fluorescence spectral results of the tests are as Figure 1 , Figure 2 , Figure 4 , Figure 6 shown, where Figure 1 is the fluorescence spectrum of compound 1 prepared in Example 1; Figure 2 is the fluorescence spectrum of compound 2 prepared in Example 2; Figure 4 is the fluorescence spectrum of compound 3 prepared in Example 3; Figure 6 is the fluorescence spectrum of compound 4 prepared in Example 4.

[0155] Figure 1 , Figure 2 , Figure 4 , Figure 6 In, the abscissa is the wavelength and the ordinate is the fluorescence intensity. The summary of the test results is shown in Table 1:

[0156] Table 1

[0157]

[0158] As can be seen from the data in Table 1, the spectrum of the compound provided in the embodiments of the present invention covers the entire visible light region, has a very good narrow emission effect both in the dispersed state and the aggregated state, and can effectively improve the color gamut of the device.

Claims

1. A compound, characterized in that, The compound has a general formula as shown in formula (I): In formula (I), M1 and M2 are each independently selected from a substituted or unsubstituted C6-C 60 aryl ring, a substituted or unsubstituted C3-C 30 heteroaryl ring; when M1 and M2 are both a substituted or unsubstituted aryl ring, at least one Z is N; i is an integer from 0 to 5, j is an integer from 0 to 5, and i + j ≥ 1; Z is independently C-R1 or N, and each R1 is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a carboxyl group, a sulfonic acid group, a C1-C 30 acyl group, a substituted or unsubstituted C1-C 30 alkyl group, a substituted or unsubstituted C3-C 30 cycloalkyl group, a substituted or unsubstituted C2-C 30 heterocycloalkyl group, a substituted or unsubstituted C1-C 30 alkoxy group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C3-C 30 heteroaryl group, a substituted or unsubstituted C6-C 30 aryloxy group, a substituted or unsubstituted C3-C 30 heteroaryloxy group, a substituted or unsubstituted C1-C 30 alkylamino group, a substituted or unsubstituted C6-C 30 arylamino group, a substituted or unsubstituted C3-C 30 heteroarylamino group, a substituted or unsubstituted B1-B 30 boranyl group, a substituted or unsubstituted Si1-Si 30 silyl group, a substituted or unsubstituted C6-C 30 arylsilyl group, or a C1-C containing at least one heteroatom of O, N, S, B, P, F other than the above groups 18 electron-withdrawing group, and adjacent R1s are connected to form a ring or not connected; R2 and R3 are each independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a carboxyl group, a sulfonic acid group, a C1-C 30 acyl group, a substituted or unsubstituted C1-C 30 alkyl group, a substituted or unsubstituted C3-C 30 cycloalkyl group, a substituted or unsubstituted C2-C 30 heterocycloalkyl group, a substituted or unsubstituted C1-C 30 alkoxy group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C3-C 30 heteroaryl group, a substituted or unsubstituted C6-C 30 aryloxy group, a substituted or unsubstituted C3-C 30 heteroaryloxy group, a substituted or unsubstituted C1-C 30 alkylamino group, a substituted or unsubstituted C6-C 30 arylamino group, a substituted or unsubstituted C3-C 30 heteroarylamino group, a substituted or unsubstituted B1-B 30 boranyl group, a substituted or unsubstituted Si1-Si 30 silyl group, a substituted or unsubstituted C6-C 30 aromatic silyl group, or a C1-C containing at least one heteroatom of O, N, S, B, P, F other than the above groups 18 electron-withdrawing group.

2. The compound according to claim 1, wherein The general formula shown in formula (I) is any one of the formulas shown in formula (I-1) to formula (I-4):

3. The compound according to claim 1, characterized in that, The heteroatom in the heteroaromatic ring is selected from one or more of an oxygen atom, a sulfur atom, a nitrogen atom, and a selenium atom.

4. The compound according to claim 1, characterized in that, The substituted or unsubstituted C6-C 60 aryl ring includes at least one of a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted biphenyl ring, a substituted or unsubstituted terphenyl ring, a substituted or unsubstituted binaphthalene ring, a substituted or unsubstituted fluorene ring, and a substituted or unsubstituted spirofluorene ring; The substituted or unsubstituted C3-C 30 The heteroaryl ring includes at least one of a substituted or unsubstituted pyrrole ring, a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted benzopyrrole ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted carbazole ring, a substituted or unsubstituted triazine ring, and a substituted or unsubstituted xanthone ring.

5. The compound according to claim 1, wherein The substituents in the substituted C6-C 60 aryl ring, substituted C3-C 30 heteroaryl ring include deuterium atom, tritium atom, halogen atom, cyano group, nitro group, hydroxyl group, carboxyl group, sulfonic acid group, C1-C 30 acyl group, substituted or unsubstituted C1-C 30 alkyl group, substituted or unsubstituted C3-C 30 cycloalkyl group, substituted or unsubstituted C2-C 30 heterocycloalkyl group, substituted or unsubstituted C1-C 30 alkoxy group, substituted or unsubstituted C6-C 30 aryl group, substituted or unsubstituted C3-C 30 heteroaryl group, substituted or unsubstituted C6-C 30 aryloxy group, substituted or unsubstituted C3-C 30 heteroaryloxy group, substituted or unsubstituted C1-C 30 alkylamino group, substituted or unsubstituted C6-C 30 arylamino group, substituted or unsubstituted C3-C 30 heteroarylamino group, substituted or unsubstituted B1-B 30 boranyl group, substituted or unsubstituted Si1-Si 30 silyl group, substituted or unsubstituted C6-C 30 one or more of aromatic silyl groups.

6. The compound according to claim 1, wherein The general formula shown in formula (I) is any one of the formulas shown in formula (II-1) to (II-12): In formulas (II-1) to (II-12), each Z is independently C-R1 or N, each X is independently O, S or N-R4, and each of R1, R2, R3, and R4 is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a carboxyl group, a sulfonic acid group, a C1-C 30 acyl group, a substituted or unsubstituted C1-C 30 alkyl group, a substituted or unsubstituted C3-C 30 cycloalkyl group, a substituted or unsubstituted C2-C 30 heterocycloalkyl group, a substituted or unsubstituted C1-C 30 alkoxy group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C3-C 30 heteroaryl group, a substituted or unsubstituted C6-C 30 aryloxy group, a substituted or unsubstituted C3-C 30 heteroaryloxy group, a substituted or unsubstituted C1-C 30 alkylamino group, a substituted or unsubstituted C6-C 30 arylamino group, a substituted or unsubstituted C3-C 30 heteroarylamino group, a substituted or unsubstituted B1-B 30 boranyl group, a substituted or unsubstituted Si1-Si 30 silyl group, a substituted or unsubstituted C6-C 30 arylsilyl group, or a C1-C containing at least one heteroatom selected from O, N, S, B, P, and F other than the above groups 18 electron-withdrawing group, adjacent R1s are connected to form a ring or not connected; R4 is connected to adjacent R1s to form a ring or not connected; In formula (II-2), (II-5), (II-9) and (II-12), at least one Z is N.

7. The compound according to any one of claims 1-6, characterized in that, The substituted C1-C 30 alkyl, substituted C3-C 30 cycloalkyl, substituted C2-C 30 heterocycloalkyl, substituted C1-C 30 alkoxy, substituted C6-C 30 aryl, substituted C3-C 30 heteroaryl, substituted C6-C 30 aryloxy, substituted C3-C 30 heteroaryloxy, substituted C1-C 30 alkylamino, substituted C6-C 30 arylamino, substituted C3-C 30 heteroarylamino, substituted B1-B 30 boranyl, substituted Si1-Si 30 silyl, substituted C6-C 30 The substituents in the arylsilyl include deuterium atom, tritium atom, halogen atom, cyano group, nitro group, hydroxyl group, carboxyl group, sulfonic acid group, C1-C 30 acyl group, C1-C 30 alkyl, C3-C 30 cycloalkyl, C2-C 30 heterocycloalkyl, C1-C 30 alkoxy, C6-C 30 aryl, C3-C 30 heteroaryl, C6-C 30 aryloxy, C3-C 30 heteroaryloxy, C1-C 30 alkylamino, C6-C 30 arylamino, C3-C 30 heteroarylamino, B1-B 30 boranyl, Si1-Si 30 silyl, C6-C 30 One or more of the arylsilyls.

8. Use of the compound according to any one of claims 1-7 and its salts in an electroluminescent device, an organic light-emitting field-effect transistor, an organic photovoltaic device, a light-emitting electrochemical cell, a photoelectric converter, a switching device, an image sensor, a laser, a photosensitive device, a bioimaging device, a coating, an organic laser device.

9. A light-emitting layer, characterized in that, The light-emitting layer comprises the compound according to any one of claims 1-7.

10. The light-emitting layer according to claim 9, characterized in that, The light-emitting layer comprises a host material and a dopant material, and the dopant material comprises the compound.

11. An electronic device, characterized in that, The electronic device comprises the compound according to any one of claims 1-7; or comprises the light-emitting layer according to any one of claims 9-10.

12. The electronic device according to claim 11, wherein The electronic device comprises a cathode and an anode, and a functional layer located between the cathode and the anode, and the functional layer comprises the compound.

13. The electronic device according to claim 11 or 12, characterized in that, The electronic device comprises an electroluminescent device, an organic light-emitting field-effect transistor, an organic photovoltaic device or a light-emitting electrochemical cell.

14. A display device, characterized in that, The display device comprises the electronic device according to any one of claims 11-13; or comprises the light-emitting layer according to any one of claims 9-10.

15. An electronic device, characterized in that, The electronic device comprises the display device according to claim 14; or comprises the electronic device according to any one of claims 11-13.

16. A lighting device, characterized in that, The lighting device comprises the electronic device according to any one of claims 11-13; or comprises the light-emitting layer according to any one of claims 9-10.

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