A compound and its application, and an organic electroluminescent device comprising the compound.

Abstract

This invention relates to a compound and its applications. The compound has the structure shown in Formula I. The compound provided by this invention is a large planar polycyclic host material. This further expands the planarity of the molecular structure while ensuring that the triplet energy levels of the original large planar system remain unchanged, thereby enhancing the transport performance and stability of the compound. When applied to organic electroluminescent devices, it can enable the devices to have better performance, such as lower voltage, higher efficiency, and longer device lifetime.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, and more particularly to a compound and its applications, and organic electroluminescent devices comprising the same. Background Technology

[0002] In recent years, optoelectronic devices based on organic materials have developed rapidly and become a research hotspot in the field. Examples of such organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic photovoltaic cells, and organic sensors. Among them, OLEDs have developed particularly rapidly and have already achieved commercial success in the field of information display. OLEDs can provide highly saturated red, green, and blue colors, and full-color display devices made with them do not require an additional backlight, offering advantages such as vibrant colors, thinness, and flexibility.

[0003] The core of an OLED device is a multilayer thin-film structure containing various organic functional materials. Common functionalized organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, as well as light-emitting host materials and light-emitting guest materials (dyes). When an electric current is applied, electrons and holes are injected and transported to the light-emitting region, where they recombine, thereby generating excitons and emitting light.

[0004] Common phosphors primarily utilize singlet excitons generated when electrons and holes combine to emit light, and are still widely used in various OLED products. Some metal complexes, such as iridium complexes, can simultaneously utilize both triplet and singlet excitons to emit light; these are called phosphors, and their energy conversion efficiency can be up to four times higher than that of traditional phosphors. Thermally excited delayed fluorescence (TADF) technology promotes the conversion of triplet excitons to singlet excitons, achieving high luminous efficiency without the use of metal complexes, while still effectively utilizing triplet excitons. Thermally excited sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize the phosphor through energy transfer, also achieving high luminous efficiency.

[0005] Although products using OLED display technology are already commercialized, there is still a need to continuously improve the lifespan, efficiency, and other performance characteristics of these devices to meet people's demands for higher quality. Therefore, there is an urgent need in this field to develop a wider variety of organic materials for use in organic electroluminescent devices, enabling these devices to achieve higher luminous efficiency, lower driving voltage, and longer lifespan. Summary of the Invention

[0006] One of the objectives of this invention is to provide a compound, particularly an organic electroluminescent material, and especially a host material for the light-emitting layer of an organic electroluminescent device, which can effectively improve luminous efficiency, reduce driving voltage, and extend service life.

[0007] To achieve this objective, the present invention adopts the following technical solution:

[0008] This invention provides a compound having the structure shown in Formula I;

[0009]

[0010] In Formula I, X 1 -X 16 Independently selected from CR 1 Or N, the R 1 Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, wherein R 1 Independently linked to an aromatic ring or heteroaromatic ring to form a ring, or not linked to an aromatic ring; when X 1 -X 16 At least two of them are selected from CR 1 At that time, there exist at least two R 1 They can be selected from the same group or from different groups (i.e., "at least two combinations");

[0011] In Formula I, Y is selected from CR 2 R 3 NR 4 O, S or SiR 5 R 6 One of them, and the Y is through CR 2 R 3 NR 4 O, S or SiR 5 R 6 The C, N, O, S or Si in the X 11 or X 16 The connection forms a six-membered ring; when C, N, O, S, or Si is combined with X 11 When connecting, X 11 For CR 1 When C, N, O, S, or Si are combined with X 16 When connecting, X 16 For CR1 ;

[0012] The R 2 R 3 R 4 R 5 and R 6 Independently selected from one of the following: substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; The R 2 and R 3 Whether connected in a loop or not, the R 5 and R 6 Connected in a loop or not connected in a loop; R 2 and R 3 It can replace C alone, or the two can be connected by a single bond to form a ring structure, R 5 and R 6 Similarly;

[0013] R 1 R 2 R 3 R 4 R 5 and R 6 In this context, each of the substituted groups is independently selected from any one or at least two combinations of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heteroarylamino. The substituents may or may not be connected to the linked aromatic or heteroaryl rings to form a ring.

[0014] The compound provided by this invention is a large planar polycyclic compound, wherein Y interacts with X through its main atom (C, N, O, S, or Si). 11 or X 16 The formation of non-conjugated six-membered rings further expands the planarity of the molecular structure while ensuring that the triplet energy levels of the original large planar system remain unchanged. This enhances the transport performance of the compound, giving it superior properties such as lower voltage, higher efficiency, and longer device lifetime.

[0015] By way of example, the compounds of general formula I of the present invention specifically include the following general formula structures:

[0016]

[0017] In the formula aj, X 1 -X 16 R2 R 3 R 4 R 5 and R 6 All have the same selection range as those mentioned above.

[0018] In this invention, "substituted group" refers to the range of substituents that can be selected when a "substituted or unsubstituted" group is substituted. The number of substituents is not specifically limited, as long as the requirements of the compound bond are met. For example, it can be 1, 2, 3, 4, or 5 substituents. When the number of substituents is 2 or more, these 2 or more substituents can be the same or different. The substituents include, but are not limited to, any one or at least two combinations of methyl, ethyl, tert-butyl, methoxy, phenyl, or diphenylamino groups.

[0019] 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.

[0020] In this invention, halogens represent chlorine atoms, fluorine atoms, bromine atoms, iodine atoms, etc.

[0021] In this invention, 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.

[0022] In this specification, the way a ring structure is represented by "—" indicates that the connection point is located at any position on the ring structure where bonding can occur.

[0023] In this specification, "each independently" means that when there are multiple subjects, they may be the same or different from each other.

[0024] In this invention, unless otherwise specified, the description of chemical elements generally includes the concept of their isotopes. For example, the description of "hydrogen (H)" includes its isotopes. 1 H (protium or H), 2 The concept of H (deuterium or D); carbon (C) includes... 12 C 13 C, etc., will not be elaborated further.

[0025] 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.

[0026] In this invention, aryl groups include monocyclic aryl groups or fused-ring aryl groups, and heteroaryl groups include monocyclic heteroaryl groups or fused-ring heteroaryl groups. A monocyclic aryl group 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 single bonds. A fused-ring aryl group refers to a molecule containing at least two benzene rings, but the benzene rings are not independent of each other; instead, they are fused together by sharing ring edges. A monocyclic heteroaryl group 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 other groups are independent of each other and connected by single bonds. A fused-ring heteroaryl group refers to a molecule formed by the fusion of at least one phenyl group and at least one heteroaryl group, or by the fusion of at least two heteroaryl rings.

[0027] In this invention, the number of carbon atoms in the aryl group includes, but is not limited to, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc., and is exemplary selected from the following groups: fluorenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, indene, fluorenyl and its derivatives, fluoranyl, triphenylene, pyrene, perylene, etc. The terphenyl group is selected from 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl and 2-naphthyl; the anthraceneyl group is selected from 1-anthrayl, 2-anthrayl, and 9- The anthracene group; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl and fluorenyl derivatives; the fluorenyl derivatives are selected from 9,9-dimethylfluorenyl, 9,9-spirodifluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, and benzo[a]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.

[0028] Specific examples of arylene groups in this invention can be exemplified by removing one hydrogen atom from the aryl groups described above, resulting in divalent groups. The number of carbon atoms in arylene groups includes, but is not limited to, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, and C28.

[0029] In this invention, arylamino represents a group formed by replacing one or two hydrogen atoms on an amino group with one or two aryl groups. The linking site of the arylamino group can be connected to either the aryl group or the nitrogen atom in the arylamino group. The exemplary number of carbon atoms and specific groups of the aryl group in the arylamino group are the same as described above. Examples of C6-C30 arylamino groups mentioned in this invention include phenylamino, methylphenylamino, naphthylamino, anthraceneylamino, phenanthreneamino, and biphenylamino.

[0030] In this invention, the number of carbon atoms in the heteroaryl group includes, but is not limited to, C4, C5, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc., and is exemplary selected from the following groups: furanyl, thiopheneyl, pyrroleyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl and its derivatives, wherein the carbazoleyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole, benzocarbazole, dibenzocarbazole, or indolocarbazole.

[0031] Specific examples of heteroaryl groups in this invention can be exemplified by removing one hydrogen atom from the aforementioned heteroaryl examples to obtain a divalent group. The number of carbon atoms in a heteroaryl group includes, but is not limited to, C4, C5, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.

[0032] Similarly, for heteroarylamino groups, the exemplary number of carbons and specific functional groups of the heteroaryl groups are the same as described above. Examples of C6-C30 arylamino groups mentioned in this invention include phenylamino, methylphenylamino, naphthylamino, anthraceneylamino, phenanthreneamino, biphenylamino, etc.

[0033] The aryl group in this invention can be exemplified by the monovalent group composed of the above-mentioned aryl and heteroaryl groups and oxygen.

[0034] 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 preferably substituted or unsubstituted C1-C16 chain alkyl groups, and 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.

[0035] 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.

[0036] In this specification, the substituted or unsubstituted C1-C20 alkoxy group is preferably a substituted or unsubstituted C1-C10 alkoxy group. Examples of C1-C10 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 isopentoxy are preferred, and methoxy is more preferred.

[0037] In this specification, the substituted or unsubstituted C1-C20 silanes and the substituted or unsubstituted C1-C10 silanes are examples of silanes substituted with groups listed in the above C1-C10 silanes, specifically including: methylsilane, dimethylsilane, trimethylsilane, ethylsilane, diethylsilane, triethylsilane, tert-butyldimethylsilane, tert-butyldiphenylsilane, etc.

[0038] C1-C20 chain alkyl groups include branched alkyl groups and straight-chain alkyl groups, preferably C1-C10 chain alkyl groups. The number of carbon atoms includes, but is not limited to, C1, C2, C3, C4, C5, C6, C7, C8, C9, etc. Examples include: methyl, ethyl, n-propyl, n-butyl, n-hexyl, n-octyl, isopropyl, isobutyl, tert-butyl, etc.

[0039] C3-C20 cycloalkyl groups are preferably C3-C10 cycloalkyl groups, and the number of carbon atoms includes, but is not limited to, C4, C5, C6, C7, C8, C9, etc., for example: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, etc.

[0040] C1-C20 alkoxy groups are preferably C1-C10 alkoxy groups, and the number of carbon atoms includes, but is not limited to, C1, C2, C3, C4, C5, C6, C7, C8, C9, etc. The exemplary alkyl groups in the alkoxy groups are the same as those in the above-mentioned C1-C20 chain alkyl groups.

[0041] The number of carbon atoms in C1-C6 thioalkoxy groups includes, but is not limited to, C2, C3, C4, and C5.

[0042] The number of carbon atoms in C1 to C20 silanes includes, but is not limited to, C1, C2, C3, C4, C5, C6, C7, C8, and C9.

[0043] Preferably, the compound has the structure shown in formula (I-1) or formula (I-2);

[0044]

[0045] The X1 -X 16 Independently selected from CR 1 Or N, the R 1 Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, wherein R 1 It can independently connect with connected aromatic or heteroaromatic rings to form a ring or not connect to form a ring;

[0046] The Y 1 and Y 2 Independently selected from CR 2 R 3 NR 4 O, S or SiR 5 R 6 One of them, the R 2 and R 3 Whether connected in a loop or not, the R 5 and R 6 Connected to form a loop or not connected to form a loop;

[0047] The R 2 R 3 R 4 R 5 and R 6 It is independently selected from one of the following: substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;

[0048] R 1 R 2 R 3 R 4 R 5 and R 6In this embodiment, each of the substituted groups is independently selected from any one or at least two combinations of cyano, halogen, nitro, hydroxyl, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heteroarylamino, preferably any one or at least two combinations of C1-C20 chain alkyl, C3-C20 cycloalkyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl, and the substituents may or may not be connected to the connected aromatic or heteroaryl rings to form a ring.

[0049] Preferably, the compound has the structure shown in formula (I-3) or formula (I-4);

[0050]

[0051] The X 1 -X 11 and X 16 Independently selected from CR 1 Or N, preferably CR 1 , the R 1 Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, wherein R 1 It can independently connect with connected aromatic or heteroaromatic rings to form a ring or not connect to form a ring;

[0052] The Y 1 and Y 2 Independently selected from CR 2 R 3 NR 4 O, S or SiR 5 R 6 One of them, the R 2 and R 3 Whether connected in a loop or not, the R 5 and R 6 Connected to form a loop or not connected to form a loop;

[0053] The R 2 R 3 R 4 R 5 and R6 It is independently selected from one of the following: substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;

[0054] The Ar 1 It is selected from one of substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, preferably one of substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, preferably one of substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;

[0055] Ar 1 R 1 R 2 R 3 R 4 R 5 and R 6 In this context, each of the substituted groups is independently selected from any one or at least two combinations of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heteroarylamino. The substituents may or may not be connected to the linked aromatic or heteroaryl rings to form a ring.

[0056] In the preferred embodiment of the present invention, Ar 1 When aromatic groups or hydrogen are used, compared to replacing other groups, it is more beneficial to improve the luminous efficiency of the device, reduce the driving voltage, and extend the device lifespan. Among them, Ar 1 The effect is better when the group is an aromatic group.

[0057] Preferably, the Y is selected from O or S.

[0058] Preferably, the Y 1 and Y 2 Choose independently from O or S.

[0059] In the preferred embodiment of the present invention, Y (or Y 1 and Y 2The luminous efficiency of the device is improved, the driving voltage is reduced, and the device life is extended, compared to the structure selected from C, N or Si.

[0060] Preferably, the Ar 1 Choose any one of the structures shown in equations (3-1) to (3-4) below:

[0061]

[0062] In equation (3-1), Z 1 Z 2 Z 3 Z 4 and Z 5 Each independently selected from CR 7 Or N atoms, and Z 1 Z 2 Z 3 Z 4 and Z 5 At least one of them is an N atom.

[0063] In equation (3-2), Z 6 Z 7 Z 8 Z 9 Z 10 Z 11 Z 12 and Z 13 Each independently selected from CR 7 Or N atoms, and Z 6 Z 7 Z 8 Z 9 Z 10 Z 11 Z 12 and Z 13 At least one of them is an N atom.

[0064] In equation (3-3), Z 14 Z 15 Z 16 Z 17 Z 18 Z 19 Z 20 Z 21 Z 22 and Z 23 Each independently selected from CR 7 Or N atoms, and Z 14 Z 15 Z 16 Z 17 Z 18 Z 19 Z20 Z 21 Z 22 and Z 23 At least one of them is an N atom.

[0065] In equation (3-4), Z 24 Z 25 Z 26 Z 27 Z 28 Z 29 Z 30 Z 31 Z 32 and Z 33 Each independently selected from CR 7 Or N atoms, and Z 24 Z 25 Z 26 Z 27 Z 28 Z 29 Z 30 Z 31 Z 32 and Z 33 At least one of them is an N atom.

[0066] The R 7 It is selected from one or a combination of at least two of the following: hydrogen, halogen, cyano, nitro, hydroxyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C1-C20 silyl, amino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C60 aryl, and C3-C60 heteroaryl.

[0067] In this context, * represents the bond attached to a group.

[0068] Preferably, the Ar 1 It has the structure shown in (3-1) or (3-2).

[0069] Preferably, in formula (3-1), Z 1 Z 2 Z 3 Z 4 and Z 5 At least two of them are N atoms.

[0070] Preferably, in equation (3-2), Z 6 Z 7 Z 8 Z 9 Z 10 Z 11 Z 12 and Z 13 At least two of them are N atoms.

[0071] Preferably, the Ar 1 Selected from one of the following groups, substituted or unsubstituted: pyridyl, quinolinyl, quinazolinyl, triazine, pyrimidinyl or quinoxalinyl;

[0072] Ar 1 In this context, each of the substituted groups is independently selected from any one or at least two combinations of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heteroarylamino. The substituents may or may not be connected to the linked aromatic or heteroaryl rings to form a ring.

[0073] Preferably, the Ar 1 Selected from one of the substituted or unsubstituted A1-A26 groups:

[0074]

[0075] Where * represents the access bond of a group;

[0076] Ar 1 In this context, each of the substituted groups is independently selected from any one or at least two combinations of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heteroarylamino. The substituents may or may not be connected to the linked aromatic or heteroaryl rings to form a ring.

[0077] Preferably, the Ar 1 Selected from one of the B1 to B19 groups:

[0078]

[0079] Where * represents the access bond of a group;

[0080] Ar 1 In this context, each of the substituted groups is independently selected from any one or at least two combinations of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heteroarylamino. The substituents may or may not be connected to the linked aromatic or heteroaryl rings to form a ring.

[0081] Preferably, the Ar 1 It is selected from one of the following: substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl containing S / O, substituted or unsubstituted carbazole, substituted or unsubstituted C6-C60 arylamino, and substituted or unsubstituted C3-C60 heteroarylamino.

[0082] Ar 1 In this context, each of the substituted groups is independently selected from any one or at least two combinations of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heteroarylamino. The substituents may or may not be connected to the linked aromatic or heteroaryl rings to form a ring.

[0083] Preferably, the Ar 1 It is selected from any one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazole, and substituted or unsubstituted diphenylamino.

[0084] Ar 1 In this context, each of the substituted groups is independently selected from any one or at least two combinations of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heteroarylamino. The substituents may or may not be connected to the linked aromatic or heteroaryl rings to form a ring.

[0085] Preferably, the X 1 -X 16 All are CH.

[0086] Preferably, the R 2 R 3 R 4 R 5 and R 6It is independently selected from one of the following: substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, preferably substituted or unsubstituted methyl, substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted triazine, substituted or unsubstituted quinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted pyrimidinyl;

[0087] R 2 R 3 R 4 R 5 and R 6 In this context, each of the substituted groups is independently selected from any one or at least two combinations of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heteroarylamino. The substituents may or may not be connected to the linked aromatic or heteroaryl rings to form a ring.

[0088] Preferably, the compound has one of the structures shown in P1 to P167:

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101] A second objective of this invention is to provide an application of the compound described in one objective, wherein the compound is used in organic electronic devices.

[0102] Preferably, the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin-film transistor, an organic field-effect transistor, an organic thin-film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner, or electronic paper.

[0103] Preferably, the compound is applied to an organic electroluminescent device, and more preferably to a red-light organic electroluminescent device.

[0104] Preferably, the compound is used as the host material of the organic electroluminescent device, and more preferably as the host material for red light.

[0105] A third objective of this invention is to provide an organic electroluminescent device, the organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer inserted between the first electrode and the second electrode, the organic layer comprising at least one of the compounds described in one of the objectives.

[0106] Preferably, the organic layer includes a light-emitting layer containing at least one of the compounds described in one of the objectives.

[0107] Preferably, the light-emitting layer comprises a host material and a dopant material, wherein the host material comprises at least one of the compounds described in one of the objectives.

[0108] Preferably, the host material comprises a first host material and a second host material, wherein at least one of the first host material and the second host material comprises a compound described in at least one of the objectives. The compounds of the present invention, when applied to dual-host devices, can effectively improve device performance.

[0109] Preferably, both the first and second host materials comprise at least one of the compounds described in one of the objectives.

[0110] In one specific embodiment, the organic layer may further include a hole transport region and an electron transport region.

[0111] In one specific embodiment, a substrate can be used below the first electrode or above the second electrode. The substrate is typically made of glass or polymer material possessing excellent mechanical strength, thermal stability, water resistance, and transparency. Furthermore, thin-film transistors (TFTs) can also be incorporated into the substrate used for displays.

[0112] In this invention, the first electrode and the second electrode are respectively an anode and a cathode. For example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

[0113] The first electrode can be formed by sputtering or depositing the material to be used as the first electrode on a substrate. When the first electrode is used as the anode, it can be a transparent conductive oxide material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof. When the first electrode is used as the cathode, it can be a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0114] Organic layers can be formed on electrodes using methods such as vacuum thermal evaporation, spin coating, and printing. Compounds used as organic layers can be small organic molecules, large organic molecules, polymers, and combinations thereof.

[0115] 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).

[0116] The material for the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, 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, wherein the aromatic amine derivatives include compounds shown below HT-1 to HT-51; or any combination thereof.

[0117]

[0118]

[0119]

[0120] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can be one or more compounds of HT-1 to HT-51 described above, or one or more compounds of HI-1 to HI-3 described below; it can also be one or more compounds of HT-1 to HT-51 doped with one or more compounds of HI-1 to HI-3 described below.

[0121]

[0122] In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light-emitting layer. The electron blocking layer may employ, but is not limited to, one or more compounds of HT-1 to HT-51 described above, or one or more compounds of PH-47 to PH-77 described below; or a mixture of one or more compounds of HT-1 to HT-51 and one or more compounds of PH-47 to PH-77 may be employed.

[0123]

[0124]

[0125] 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.

[0126] Depending on the technology used, the light-emitting layer material can be various, including fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescence materials. An OLED device can employ a single light-emitting technology or a combination of different technologies. These different light-emitting materials, categorized by technology, can emit light of the same color or different colors.

[0127] In one aspect of the invention, the light-emitting layer employs phosphorescent photoluminescence technology. The phosphorescent dopant of the light-emitting layer may be selected from, but not limited to, one or more combinations of RPD-1 to RPD-28 listed below.

[0128]

[0129]

[0130] 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).

[0131] In one aspect of the present invention, the electron transport layer material may be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0132]

[0133]

[0134]

[0135]

[0136] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light-emitting layer. The hole blocking layer may employ, but is not limited to, one or more compounds of ET-1 to ET-73 described above, or one or more compounds of PH-1 to PH-46 described below; or a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-46 may be employed.

[0137]

[0138]

[0139]

[0140] The device may also include an electron injection layer located between the electron transport layer and the cathode, and the electron injection layer material includes, but is not limited to, one or more combinations of the following.

[0141] Liq, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Yb.

[0142] The cathode is a mixture of magnesium and silver, LiF / Al, ITO and other metals, metal mixtures and oxides.

[0143] Compared with the prior art, the present invention has the following beneficial effects:

[0144] The compound provided by this invention is a large planar polycyclic host material, wherein Y interacts with X through its main atom. 11 or X 16 The formation of non-conjugated six-membered rings further expands the planarity of the molecular structure while ensuring that the triplet energy levels of the original large planar system remain unchanged. This enhances the transport performance of the compound, giving it superior properties such as lower voltage, higher efficiency, and longer device lifetime. It is particularly suitable as a host material for the light-emitting layer, especially for red light. Detailed Implementation

[0145] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention in any way.

[0146] The representative synthetic routes of the compounds of general formula I provided by this invention are as follows:

[0147]

[0148] The preparation methods of the compounds of the present invention include, but are not limited to, the above-described synthesis methods. Those skilled in the art can also make conventional adjustments to the preparation methods according to actual needs. The preparation methods of the present invention are not specifically limited.

[0149] The following intermediates and final products were detected by mass spectrometry (MS) using an ABSCIEX mass spectrometer (4000QTRAP).

[0150] In specific embodiments, the preparation methods of the intermediates used in the following synthesis examples are as follows:

[0151] Synthesis of intermediate M1:

[0152]

[0153] 0.2 mol of 3-fluoro-1-naphthoic acid, 0.21 mol of 2,3-dichloronitrobenzene, 0.3 mol of potassium carbonate, 0.002 mol of tetra(triphenylphosphine)palladium, 80 mL of water, and 500 mL of dioxane were added to a reaction flask. The mixture was heated to 90 °C and reacted for 6 h. The reaction was monitored by TLC until complete. Water and dichloromethane were added for extraction. After separating the organic phase, the mixture was concentrated to obtain M1-A.

[0154] M1-A (0.15 mol), triphenylphosphine (0.5 mol), and o-dichlorobenzene were added to a reaction flask and heated to reflux for 4 h. The reaction was monitored by TLC until complete. After the solvent was removed by vacuum distillation, M1-B was purified by column chromatography.

[0155] M1-B (0.1 mol), pinacol ester of 2-aminophenylboronic acid (0.11 mol), potassium phosphate (0.15 mol), tris(dibenzylacetone)palladium (0.001 mol), 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (0.002 mol), water (50 mL), and dioxane (300 mL) were added to a reaction flask and heated to 100 °C for 8 h. The reaction was monitored by TLC until complete. Water and dichloromethane were added for extraction, and the organic phase was separated and concentrated to obtain M1-C.

[0156] M1-C (0.05 mol), copper powder (0.05 mol), and dimethyl sulfoxide were added to a reaction flask, cooled to 20 °C, and tert-butyl nitrite (0.08 mol) was added dropwise. After the addition was complete, the mixture was heated to reflux at 60 °C for 4 h. The reaction was monitored by TLC until complete, and the solvent was removed by vacuum distillation and purified by column chromatography to obtain M1 (MS, 310.1).

[0157] Synthesis of intermediate M2:

[0158]

[0159] The method is the same as that used for the synthesis of M1, except that 3-fluoro-1-naphthoboric acid is replaced with an equal amount of 1-naphthoboric acid; and 2,3-dichloronitrobenzene is replaced with an equal amount of 1,2-dichloro-4-fluoro-3-nitrobenzene, to obtain M2 (MS, 310.1).

[0160] Synthesis of intermediate M4:

[0161]

[0162] 5-Bromo-7-methoxyquinoline (0.5 mol) was added to 1 L of tetrahydrofuran, the temperature was lowered to -78 °C, and n-butyllithium (0.6 mol) was added dropwise. After the addition was complete, the temperature was maintained for 30 minutes, and then triisopropyl borate (0.8 mol) was added dropwise. After the addition was complete, the temperature was gradually restored to room temperature. After the reaction was completed by TLC monitoring, dilute hydrochloric acid was added to quench the reaction, and then ethyl acetate was extracted. The organic phase was concentrated to obtain S1.

[0163] The subsequent synthesis method is the same as that of intermediate M1, except that replacing 3-fluoro-1-naphthoboric acid with an equal amount of S1 can yield intermediate M4-D.

[0164] M4-D (0.05 mol) was added to 200 mL of dichloromethane, cooled to 0 °C, and boron tribromide (0.1 mol) was added dropwise. The reaction was carried out at room temperature for 2 h. The reaction was monitored by TLC until it was completed. The mixture was slowly introduced into ice water to separate the layers. The organic phase was concentrated to obtain intermediate M4 (MS, 308.1).

[0165] Synthesis example 1:

[0166] Synthesis of compound P1

[0167]

[0168] M1 (0.1 mol), 2-bromo-4-chlorophenol, sodium tert-butoxide (0.3 mol), tris(dibenzylacetone)palladium (0.001 mol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.002 mol, S-Phos), and xylene (300 mL) were added to a reaction flask and heated to 140 °C for 8 h. The reaction was monitored by TLC until complete. After cooling, water and dichloromethane were added for extraction. The organic phase was concentrated and purified by column chromatography to obtain P1-A.

[0169] P1-A (0.07 mol) was added to 200 mL of LDMF (N,N-dimethylformamide), cooled to 0 °C, and 0.1 mol of sodium hydroxide was slowly added. The mixture was heated to 60 °C and reacted for 3 h. The reaction was monitored by TLC until it was complete. The reaction solution was cooled and then introduced into 500 mL of water. A large amount of solid was generated. The mixture was filtered, and the filter cake was washed with ethanol to obtain the dried intermediate P1-B.

[0170] P1-B (0.05 mol), phenylboronic acid (0.06 mol), potassium carbonate (0.08 mol), tetra(triphenylphosphine)palladium (0.0005 mol), water (20 mL), and dioxane (150 mL) were added to a reaction flask. The mixture was heated to 100 °C and reacted for 6 h. The reaction was monitored by TLC until complete. Water and dichloromethane were added for extraction. After separating the organic phase, the mixture was concentrated and purified by column chromatography to obtain P1 (MS, 458.2).

[0171] Synthesis example 2:

[0172] Synthesis of compound P5

[0173]

[0174] P1-B (0.05 mol), 4-(2-naphthyl)-N-phenylaniline (0.05 mol), sodium tert-butoxide (0.1 mol), tris(dibenzylacetone)palladium (0.0005 mol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.001 mol, S-Phos), and xylene (300 mL) were added to a reaction flask and heated to 140 °C for 8 h. The reaction was monitored by TLC until complete. After cooling, water and dichloromethane were added for extraction. The organic phase was concentrated and purified by column chromatography to obtain P5 (MS, 675.2).

[0175] Synthesis example 3:

[0176] Synthesis of compound P7

[0177]

[0178] M1 (0.1 mol), 2-bromo-5-chlorophenol, sodium tert-butoxide (0.3 mol), tris(dibenzylacetone)palladium (0.001 mol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.002 mol, S-Phos), and xylene (300 mL) were added to a reaction flask and heated to 140 °C for 8 h. The reaction was monitored by TLC until complete. After cooling, water and dichloromethane were added for extraction. The organic phase was concentrated and purified by column chromatography to obtain P7-A.

[0179] P7-A (0.07 mol) was added to 200 mL of LDMF (N,N-dimethylformamide), cooled to 0 °C, and 0.1 mol of sodium hydroxide was slowly added. The mixture was heated to 60 °C and reacted for 3 h. The reaction was monitored by TLC until it was complete. The reaction solution was cooled and then introduced into 500 mL of water. A large amount of solid was generated. The mixture was filtered, and the filter cake was washed with ethanol to obtain the dried intermediate P7-B.

[0180] P7-B (0.05 mol), pinacol diboronate (0.08 mol), potassium acetate (0.1 mol), [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (0.0005 mol), and 200 mL of dioxane were added to a reaction flask and heated to 110 °C for 8 h. The reaction was monitored by TLC until complete. Water and dichloromethane were added for extraction. After separating the organic phase, the mixture was concentrated, washed with methanol, and filtered to obtain P7-C.

[0181] P7-C (0.05 mol), 2-chloro-4-phenylquinazoline (0.06 mol), potassium carbonate (0.08 mol), tetra(triphenylphosphine)palladium (0.0005 mol), water (20 mL), and dioxane (150 mL) were added to a reaction flask. The mixture was heated to 100 °C and reacted for 6 h. The reaction was monitored by TLC until complete. Water and dichloromethane were added for extraction. After separating the organic phase, the mixture was concentrated and purified by column chromatography to obtain P7 (MS, 586.2).

[0182] Synthesis example 4:

[0183] Synthesis of compound P44

[0184]

[0185] M2 (0.1 mol), 2-bromo-4-chlorophenol (0.1 mol), sodium tert-butoxide (0.3 mol), tris(dibenzylacetone)palladium (0.001 mol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.002 mol, S-Phos), and xylene (300 mL) were added to a reaction flask and heated to 140 °C for 8 h. The reaction was monitored by TLC until complete. After cooling, water and dichloromethane were added for extraction. The organic phase was concentrated and purified by column chromatography to obtain P44-A.

[0186] P44-A (0.07 mol) was added to 200 mL of LDM (N,N-dimethylformamide), cooled to 0 °C, and 0.1 mol of sodium hydroxide was slowly added. The mixture was heated to 60 °C and reacted for 3 h. The reaction was monitored by TLC until it was complete. The reaction solution was cooled and then introduced into 500 mL of water. A large amount of solid was generated. The mixture was filtered, and the filter cake was washed with ethanol to obtain the dried intermediate P44-B.

[0187] P44-B (0.05 mol), pinacol diboronate (0.08 mol), potassium acetate (0.1 mol), [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (0.0005 mol), and 200 mL of dioxane were added to a reaction flask and heated to 110 °C for 8 h. The reaction was monitored by TLC until complete. Water and dichloromethane were added for extraction. After separating the organic phase, the mixture was concentrated, washed with methanol, and filtered to obtain P44-C.

[0188] P44-C (0.05 mol), 2-chloro-4,6-diphenyltriazine (0.06 mol), potassium carbonate (0.08 mol), tetra(triphenylphosphine)palladium (0.0005 mol), water (20 mL), and dioxane (150 mL) were added to a reaction flask. The mixture was heated to 100 °C and reacted for 6 h. The reaction was monitored by TLC until complete. The mixture was extracted with water and dichloromethane. After separating the organic phase, the mixture was concentrated and purified by column chromatography to obtain P44 (MS, 613.2).

[0189] Synthesis example 5

[0190] Synthesis of compound P73

[0191]

[0192] M1 (0.1 mol), 2,3-dichloro-thiophenol (0.1 mol), sodium tert-butoxide (0.3 mol), tris(dibenzylacetone)dipalladium (0.001 mol), tri-tert-butylphosphine (0.002 mol), and xylene (300 mL) were added to a reaction flask and heated to 140 °C for 15 h. The reaction was monitored by TLC until complete. After cooling, water and dichloromethane were added for extraction. The organic phase was concentrated and purified by column chromatography to obtain P73-A.

[0193] P73-A (0.08 mol) was added to 200 mL of LDM (N,N-dimethylformamide), cooled to 0 °C, and 0.12 mol of sodium hydroxide was slowly added. The mixture was heated to 60 °C and reacted for 5 h. The reaction was monitored by TLC until it was complete. The reaction solution was cooled and then introduced into 500 mL of water. A large amount of solid was generated. The mixture was filtered, and the filter cake was washed with ethanol to obtain the dried intermediate P73-B.

[0194] P73-B (0.06 mol), pinacol diborate (0.12 mol), potassium acetate (0.2 mol), tris(dibenzylacetone)palladium (0.0006 mol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.0012 mol, S-Phos), and dioxane (200 mL) were added to a reaction flask. The mixture was heated to 110 °C and reacted for 8 h. The reaction was monitored by TLC until complete. Water and dichloromethane were added for extraction. After separating the organic phase, the mixture was concentrated, washed with methanol, and filtered to obtain P73-C.

[0195] P73-C (0.05 mol), 2-chloro-4,6-diphenyltriazine (0.06 mol), potassium carbonate (0.08 mol), tetra(triphenylphosphine)palladium (0.0005 mol), water (20 mL), and dioxane (150 mL) were added to a reaction flask. The mixture was heated to 100 °C and reacted for 6 h. The reaction was monitored by TLC until complete. Water and dichloromethane were added for extraction. After separating the organic phase, the mixture was concentrated and purified by column chromatography to obtain P73 (MS, 629.2).

[0196] Synthesis example 6:

[0197] Synthesis of compound P82

[0198] The difference from Synthesis Example 5 is that 2-chloro-4,6-diphenyltriazine was replaced with an equimolar amount of 2-bromodibenzofuran, yielding compound P82 (MS, 564.1).

[0199] Synthesis example 7:

[0200] Synthesis of compound P102

[0201]

[0202] The difference from Synthesis Example 4 is that 2-bromo-4-chlorophenol was replaced with an equal amount of 2-bromo-4-chlorothiophenol, and 2-chloro-4,6-diphenyltriazine was replaced with an equal amount of 2-chloro-3-phenylquinoxaline to obtain compound P102 (MS, 602.2).

[0203] Synthesis example 8:

[0204] Synthesis of compound P150

[0205]

[0206] M3 (0.1 mol), methyl o-bromobenzoate (0.1 mol), sodium tert-butoxide (0.2 mol), tris(dibenzylacetone)dipalladium (0.001 mol), tri-tert-butylphosphine (0.002 mol), and toluene (300 mL) were added to a reaction flask and heated to 110 °C for 10 h. The reaction was monitored by TLC until complete. After cooling, water and dichloromethane were added for extraction. The organic phase was concentrated and purified by column chromatography to obtain P150-A.

[0207] P150-A (0.08 mol) was added to 200 mL of tetrahydrofuran, cooled to 0 °C, and 0.2 mol of phenyl magnesium bromide was slowly added. After the addition was complete, the reaction was carried out at room temperature for 4 h. The reaction was monitored by TLC until it was complete. The reaction solution was cooled and introduced into 200 mL of dilute hydrochloric acid. The solution was extracted with dichloromethane and the organic phase was concentrated to obtain P150-B.

[0208] P150-B (0.06 mol) was added to 200 mL of acetic acid and 50 mL of concentrated hydrochloric acid, and the mixture was heated to reflux for 4 h. The reaction was monitored by TLC until it was complete. After removing most of the acetic acid by rotary evaporation, water and dichloromethane were added for extraction, and the product P150 was purified by organic phase column chromatography (MS, 532.2).

[0209] Synthesis example 9:

[0210] Synthesis of compounds P121 and P140

[0211]

[0212] M3 (0.2 mol), o-fluoronitrobenzene (0.2 mol), and potassium carbonate (0.3 mol) were added to 500 mL of LDMF (N,N-dimethylformamide). The mixture was heated to 100 °C and reacted for 5 h. The reaction was monitored by TLC until it was complete. The reaction solution was cooled and then introduced into 500 mL of water. A large amount of solid was generated. The mixture was filtered, and the filter cake was washed with ethanol to obtain the dried intermediate P121-A.

[0213] P121-A (0.15 mol) and triphenylphosphine (0.45 mol) were added to 500 mL of o-dichlorobenzene and reacted at 150 °C for 8 h. The o-dichlorobenzene in the reaction solution was directly distilled off, and the residue was purified by column chromatography to separate P121-B and P140-B. (Through...) 1 HNMR analysis revealed that one hydrogen singlet was from intermediate P121-B, and the other was from P140-B.

[0214] P121-B (0.05 mol), 4-bromobiphenyl (0.06 mol), sodium tert-butoxide (0.1 mol), tris(dibenzylacetone)dipalladium (0.0005 mol), tri-tert-butylphosphine (0.001 mol), and xylene (200 mL) were added to a reaction flask and heated to 140 °C for 10 h. The reaction was monitored by TLC until complete. After cooling, water and dichloromethane were added for extraction. The organic phase was concentrated and purified by column chromatography to obtain P121 (MS, 546.2).

[0215] Similar to the synthesis of P121, 4-bromobiphenyl was replaced with an equimolar amount of 4-bromodibenzofuran, and P121-B was replaced with an equimolar amount of P140-B to obtain product P140 (MS, 546.2).

[0216] Synthesis example 10:

[0217] Synthesis of compound P162

[0218]

[0219] M4 (0.1 mol), 2-bromo-3-chlorofluorobenzene (0.1 mol), sodium tert-butoxide (0.2 mol), tris(dibenzylideneacetone)palladium (0.001 mol), tri-tert-butylphosphine (0.002 mol), and xylene (300 mL) were added to a reaction flask and heated to 140 °C for 9 h. The reaction was monitored by TLC until complete. After cooling, water and dichloromethane were added for extraction. The organic phase was concentrated and purified by column chromatography to obtain P162-A.

[0220] P162-A (0.07 mol) was added to 200 mL of LDM (N,N-dimethylformamide), cooled to 0 °C, and 0.14 mol of sodium hydroxide was slowly added. The mixture was heated to 60 °C and reacted for 5 h. The reaction was monitored by TLC until it was complete. The reaction solution was cooled and then introduced into 500 mL of water. A large amount of solid was generated. The mixture was filtered, and the filter cake was washed with ethanol to obtain the dried intermediate P162-B.

[0221] P162-B (0.05 mol), pinacol diborate (0.08 mol), potassium acetate (0.1 mol), tris(dibenzylacetone)palladium (0.0005 mol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.001 mol, S-Phos), and dioxane (200 mL) were added to a reaction flask. The mixture was heated to 110 °C and reacted for 10 h. The reaction was monitored by TLC until complete. Water and dichloromethane were added for extraction. After separating the organic phase, the mixture was concentrated, washed with methanol, and filtered to obtain P162-C.

[0222] P162-C (0.03 mol), 2-chloro-4,6-diphenyltriazine (0.035 mol), potassium carbonate (0.05 mol), tetra(triphenylphosphine)palladium (0.0003 mol), water (15 mL), and dioxane (200 mL) were added to a reaction flask and heated to 110 °C for 6 h. The reaction was monitored by TLC until complete. Water and dichloromethane were added for extraction. After separating the organic phase, the mixture was concentrated and purified by column chromatography to obtain P162 (MS, 614.2).

[0223] This invention provides exemplary methods for synthesizing the above-mentioned compounds. For compounds in the following examples that do not have specific synthesis methods, they are also prepared by similar methods, requiring only the replacement of raw materials. These methods will not be elaborated here, or those skilled in the art can prepare them using other methods in the prior art.

[0224] Examples 1-13, Comparative Examples 1-4

[0225] The above embodiments and comparative examples each provide an organic electroluminescent device, and the specific fabrication methods are as follows:

[0226] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a acetone:ethanol mixed solvent, baked in a clean environment until all moisture was removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0227] The glass substrate with the ITO anode was placed in a vacuum chamber and evacuated to a vacuum level of <1×10⁻⁶. -5 Pa, on the above-mentioned anode film, a 10 nm HT-4:HI-3 (97 / 3, w / w) mixture is vacuum thermally deposited as a hole injection layer; a 60 nm HT-4 compound is used as a hole transport layer; on the hole transport layer, a HT-47 compound is vacuum-deposited as an electron blocking layer material for the device, with a deposition rate of 0.1 nm / s and a total film thickness of 60 nm; a 40 nm host material: a RPD-8 (100:3, w / w) binary mixture is used as a light-emitting layer; on the light-emitting layer, a 5 nm ET-17 is vacuum-deposited as a hole blocking layer for the device; a 25 nm ET-69:ET-57 (50 / 50, w / w) mixture is used as an electron transport layer; a 1 nm LiF is used as an electron injection layer; and a 150 nm aluminum metal is used as a cathode.

[0228] The main material in the light-emitting layer includes a first main material, or includes a first main material and a second main material (i.e., dual main materials), as detailed in Table 1 (single main material) and Table 2 (dual main materials). When dual main materials are present, the mass ratio of the first main material to the second main material is 3:7. The total film thickness of the light-emitting layer remains unchanged when the dual-source co-evaporation method is used.

[0229] In the above steps, the total evaporation rate of all organic layers and LiF was controlled at 0.1 nm / s, and the evaporation rate of the metal electrode was controlled at 1 nm / s.

[0230] The structure of the main material used in the comparative example is as follows:

[0231]

[0232] Performance testing

[0233] The following performance tests were performed on the organic electroluminescent devices provided in the above embodiments and comparative examples:

[0234] Under the same brightness, the driving voltage and current efficiency, as well as the lifetime of the organic electroluminescent device, were measured using a digital source meter and a luminance meter. Specifically, the voltage was increased at a rate of 0.1V per second, and the measurement was performed when the brightness of the organic electroluminescent device reached 3000 cd / m². 2 The voltage at that time is the driving voltage, and the current density at that time is measured simultaneously; the ratio of brightness to current density is the current efficiency; the life test of LT97 is as follows: using a luminance meter at 10000 cd / m² 2 At a constant current, the brightness of the organic electroluminescent device decreased to 9700 cd / m² under the specified brightness. 2 The test data is detailed in Tables 1 and 2.

[0235] In Table 1, the measurement data (voltage, efficiency, and lifespan) of Comparative Example 1 are set as reference data, and all other data are normalized values.

[0236] In Table 2, the measurement data (voltage, efficiency, and lifespan) of Comparative Example 4 are set as reference data, and all other data are normalized values.

[0237] Table 1 Single-body components

[0238] serial number Main materials <![CDATA[Brightness (cd / m 2 )]]> Voltage efficiency LT97 lifespan Comparative Example 1 C1 3000 1 1 1 Comparative Example 2 C2 3000 1.4 0.76 0.28 Comparative Example 3 C3 3000 1.6 0.81 0.12 Example 1 P7 3000 0.98 1.02 3.2 Example 2 P44 3000 0.94 1.05 1.5 Example 3 P73 3000 0.92 1.04 1.4 Example 4 P98 3000 0.98 1.02 1.9 Example 5 P102 3000 0.96 1.03 1.2 Example 6 P166 3000 0.96 1.02 1.1

[0239] Table 2 Dual-body components

[0240] serial number First main material Second main material <![CDATA[Brightness (cd / m 2 )]]> Voltage efficiency LT97 lifespan Example 7 P1 P44 3000 0.97 1.03 1.3 Example 8 P5 P44 3000 0.92 1.05 1.8 Example 9 P82 P44 3000 0.97 1.03 1.1 Example 10 P121 P44 3000 0.97 1.02 1.2 Example 11 P140 P44 3000 0.98 1.02 1.2 Example 12 P150 P44 3000 0.98 1.01 1.1 Example 13 C4 P44 3000 0.99 1.01 1 Comparative Example 4 C4 C1 3000 1 1 1

[0241] As shown in Table 1, when the compounds provided by this invention are applied to organic electroluminescent devices, they can effectively improve the luminous efficiency of the devices, reduce the driving voltage, and extend the device lifespan. They are particularly suitable as the red light host material for the light-emitting layer, and achieve excellent device performance in both single-host and dual-host devices.

[0242] Compared with compound P166, compound C1 differs only in that it does not contain a non-conjugated six-membered ring structure. Devices using C1 as the main light-emitting layer are inferior to devices using P166 in terms of current efficiency, driving voltage, and device lifetime.

[0243] Compared to compound P98, compound C3 contains only a five-membered thiophene ring fused with the parent nucleus and lacks a non-conjugated six-membered ring structure. Consequently, the device performance of C3 is significantly inferior to that of compound P98. Therefore, the combination of the non-conjugated six-membered ring structure with a large planar parent nucleus in this invention can effectively improve the performance of organic electroluminescent devices.

[0244] The present invention has been illustrated with the above embodiments to explain the detailed method of the present invention. However, the present invention is not limited to the detailed method described above, that is, it does not mean that the present invention must rely on the detailed method described above to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A compound, characterized in that, The compound has the structure shown in Formula I; In Formula I, X 1 -X 16 Independently selected from CR 1 Or N, the R 1 Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, wherein R 1 It can independently connect with connected aromatic or heteroaromatic rings to form a ring or not connect to form a ring; In Formula I, Y is selected from CR 2 R 3 NR 4 One of O or S, and the Y is obtained through CR 2 R 3 NR 4 C, N, O or S in O or S and X 11 or X 16 The connection forms a six-membered ring; when C, N, O, or S is connected to X 11 When connecting, X 11 For CR 1 When C, N, O, or S is with X 16 When connecting, X 16 For CR 1 ; The R 2 R 3 R 4 Independently selected from one of the following: substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; The R 2 and R 3 Connected to form a loop or not connected to form a loop; R 1 R 2 R 3 R 4 In this context, each of the substituted groups is independently selected from any one or at least two combinations of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heteroarylamino. The substituents may or may not be connected to the linked aromatic or heteroaryl rings to form a ring.

2. The compound according to claim 1, characterized in that, The compound has the structure shown in formula (I-1) or formula (I-2); The X 1 -X 16 Independently selected from CR 1 Or N, the R 1 Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, wherein R 1 It can independently connect with connected aromatic or heteroaromatic rings to form a ring or not connect to form a ring; The Y 1 and Y 2 Independently selected from CR 2 R 3 NR 4 One of O or S; The R 2 R 3 R 4 Independently selected from one of the following: substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; The R 2 and R 3 Connected to form a loop or not connected to form a loop; R 1 R 2 R 3 R 4 In this embodiment, each of the substituted groups is independently selected from any one or at least two combinations of cyano, halogen, nitro, hydroxyl, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heteroarylamino, preferably any one or at least two combinations of C1-C20 chain alkyl, C3-C20 cycloalkyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl, and the substituents may or may not be connected to the connected aromatic or heteroaryl rings to form a ring.

3. The compound according to claim 1, characterized in that, The compound has the structure shown in formula (I-3) or formula (I-4); The X 1 -X 11 and X 16 Independently selected from CR 1 Or N, preferably CR 1 The R 1 Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, wherein R 1 It can independently connect with connected aromatic or heteroaromatic rings to form a ring or not connect to form a ring; The Y 1 and Y 2 Independently selected from CR 2 R 3 NR 4 One of O or S; The R 2 R 3 R 4 Independently selected from one of the following: substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; The R 2 and R 3 Connected to form a loop or not connected to form a loop; The Ar 1 It is selected from one of hydrogen, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, preferably one of substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, preferably one of substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; Ar 1 R 1 R 2 R 3 R 4 In this context, each of the substituted groups is independently selected from any one or at least two combinations of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heteroarylamino. The substituents may or may not be connected to the linked aromatic or heteroaryl rings to form a ring.

4. The compound according to claim 1, characterized in that, The X 1 -X 11 and X 16 All are CH.

5. The compound according to claim 1, characterized in that, The Y is selected from O or S.

6. The compound according to claim 2, characterized in that, The Y 1 and Y 2 Choose independently from O or S.

7. The compound according to claim 3, characterized in that, The Ar 1 Choose any one of the structures shown in equations (3-1) to (3-4) below: In equation (3-1), Z 1 Z 2 Z 3 Z 4 and Z 5 Each independently selected from CR 7 Or N atoms, and Z 1 Z 2 Z 3 Z 4 and Z 5 At least one of them is an N atom. In equation (3-2), Z 6 Z 7 Z 8 Z 9 Z 10 Z 11 Z 12 and Z 13 Each independently selected from CR 7 Or N atoms, and Z 6 Z 7 Z 8 Z 9 Z 10 Z 11 Z 12 and Z 13 At least one of them is an N atom. In equation (3-3), Z 14 Z 15 Z 16 Z 17 Z 18 Z 19 Z 20 Z 21 Z 22 and Z 23 Each independently selected from CR 7 Or N atoms, and Z 14 Z 15 Z 16 Z 17 Z 18 Z 19 Z 20 Z 21 Z 22 and Z 23 At least one of them is an N atom. In equation (3-4), Z 24 Z 25 Z 26 Z 27 Z 28 Z 29 Z 30 Z 31 Z 32 and Z 33 Each independently selected from CR 7 Or N atoms, and Z 24 Z 25 Z 26 Z 27 Z 28 Z 29 Z 30 Z 31 Z 32 and Z 33 At least one of them is an N atom. The R 7 It is selected from one or a combination of at least two of the following: hydrogen, halogen, cyano, nitro, hydroxyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C1-C20 silyl, amino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C60 aryl, and C3-C60 heteroaryl. In this context, * represents the bond that the group is attached to.

8. The compound according to claim 7, characterized in that, The Ar 1 It has the structure shown in (3-1) or (3-2).

9. The compound according to claim 8, characterized in that, In equation (3-1), Z 1 Z 2 Z 3 Z 4 and Z 5 At least two of them are N atoms.

10. The compound according to claim 8, characterized in that, In equation (3-2), Z 6 Z 7 Z 8 Z 9 Z 10 Z 11 Z 12 and Z 13 At least two of them are N atoms.

11. The compound according to claim 3, characterized in that, The Ar 1 Selected from one of the following groups, substituted or unsubstituted: pyridyl, quinolinyl, quinazolinyl, triazine, pyrimidinyl or quinoxalinyl; Ar 1 In this context, each of the substituted groups is independently selected from any one or at least two combinations of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heteroarylamino. The substituents may or may not be connected to the linked aromatic or heteroaryl rings to form a ring.

12. The compound according to claim 3, characterized in that, The Ar 1 Selected from one of the substituted or unsubstituted A1-A26 groups: Where * represents the access bond of a group; Ar 1 In this context, each of the substituted groups is independently selected from any one or at least two combinations of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heteroarylamino. The substituents may or may not be connected to the linked aromatic or heteroaryl rings to form a ring.

13. The compound according to claim 3, characterized in that, The Ar 1 Selected from one of the B1 to B19 groups: Where * represents the access bond of a group; Ar 1 In this context, each of the substituted groups is independently selected from any one or at least two combinations of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heteroarylamino. The substituents may or may not be connected to the linked aromatic or heteroaryl rings to form a ring.

14. The compound according to claim 3, characterized in that, The Ar 1 It is selected from one of the following: substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl containing S / O, substituted or unsubstituted carbazole, substituted or unsubstituted C6-C60 arylamino, and substituted or unsubstituted C3-C60 heteroarylamino. Ar 1 In this context, each of the substituted groups is independently selected from any one or at least two combinations of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heteroarylamino. The substituents may or may not be connected to the linked aromatic or heteroaryl rings to form a ring.

15. The compound according to claim 14, characterized in that, The Ar 1 It is selected from any one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazole, and substituted or unsubstituted diphenylamino. Ar 1 In this context, each of the substituted groups is independently selected from any one or at least two combinations of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heteroarylamino. The substituents may or may not be connected to the linked aromatic or heteroaryl rings to form a ring.

16. The compound according to claim 1, characterized in that, The X 1 -X 16 All are CH.

17. The compound according to claim 1, characterized in that, The R 2 R 3 R 4 It is independently selected from one of the following: substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; R 2 R 3 R 4 In this context, each of the substituted groups is independently selected from any one or at least two combinations of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heteroarylamino. The substituents may or may not be connected to the linked aromatic or heteroaryl rings to form a ring.

18. The compound according to claim 17, characterized in that, The R 2 R 3 R 4 It is selected from one of the following: substituted or unsubstituted methyl, substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted triazineyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted pyrimidinyl; R 2 R 3 R 4 In this context, each of the substituted groups is independently selected from any one or at least two combinations of amino, cyano, halogen, nitro, hydroxyl, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl, and C3-C60 heteroarylamino. The substituents may or may not be connected to the linked aromatic or heteroaryl rings to form a ring.

19. The compound according to claim 1, characterized in that, The compound has one of the structures shown in P1 to P167 below:

20. The use of a compound according to any one of claims 1-19, characterized in that, The compound is used in organic electronic devices.

21. The application according to claim 20, characterized in that, The organic electronic devices include organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin-film transistors, organic field-effect transistors, organic thin-film solar cells, information tags, electronic artificial skin sheets, sheet-type scanners, or electronic paper.

22. The application according to claim 20, characterized in that, The compound is used in organic electroluminescent devices.

23. The application according to claim 20, characterized in that, The compound is used in red organic light-emitting devices.

24. The application according to claim 22, characterized in that, The compound is used as the host material for the organic electroluminescent device.

25. The application according to claim 24, characterized in that, The compound serves as the host material for red light.

26. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes a first electrode, a second electrode, and an organic layer inserted between the first electrode and the second electrode, wherein the organic layer contains at least one compound according to any one of claims 1-19.

27. The organic electroluminescent device according to claim 26, characterized in that, The organic layer includes a light-emitting layer, which contains at least one compound according to any one of claims 1-19.

28. The organic electroluminescent device according to claim 27, characterized in that, The light-emitting layer comprises a host material and a dopant material, wherein the host material comprises at least one compound according to any one of claims 1-19.

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