Polycyclic aromatic compound and application thereof in electroluminescent device

Abstract

The invention provides a polycyclic aromatic compound and application thereof, the polycyclic aromatic compound has a structure as shown in the following formula, X1 and X2 are respectively and independently O, S, Se, NR1, CR2R3 or SiR4R5, ring A, ring B and ring C are respectively and independently selected from one of an unsubstituted or R '-substituted C6-C60 aromatic ring and an unsubstituted or R'-substituted C3-C60 heteroaromatic ring, at least one of the ring A, the ring B and the ring C is in fused connection with a group with a structure as shown in a formula (2). When the compound provided by the invention is used in the organic electroluminescent device, especially as a luminescent dye material, the service life of the device can be remarkably prolonged, and the luminescent property of the device can be optimized. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to an organic compound, and also relates to the application of such compounds, and to an organic electroluminescent device employing such an organic compound. Background Art

[0002] In the past three decades, the field of organic light-emitting diodes (OLEDs) has made rapid progress and has now become one of the most promising technologies for full-color display and lighting applications. In an OLED, the electroluminescent layer is a thin film composed of organic compounds that can produce a light response to an electric current. This organic layer, together with other organic functional material layers, is located between the positive and negative electrode film layers. Due to the advantages of self-luminescence, high brightness, fast response, wide viewing angle, simple process, and flexibility of OLED devices, they have attracted much attention in the fields of new display technologies and new lighting technologies. Currently, this technology has been widely applied in fields such as mobile phones, computers, lighting products, etc., and the OLED materials industry has been continuously committed to developing new organic electroluminescent materials to achieve low operating voltage, high color purity, high luminous efficiency, and longer service life of devices.

[0003] Many studies have been conducted to improve the characteristics of OLED devices by changing the properties of the organic layer materials. In recent years, the research group of Takuji Hatakeyama in Japan has reported a series of thermally activated delayed fluorescence (MR-TADF) materials based on boron-nitrogen resonance. Compared with traditional donor-acceptor compounds, MR-TADF molecules have both high radiative transition rates and relatively narrow full-width at half-maximum, making them ideal materials for the organic light-emitting layer. However, the rigid planar structure of such molecules also leads to a large energy difference between the singlet and triplet energy levels, slow reverse intersystem crossing from the triplet state to the singlet state, serious efficiency roll-off after excitons recombine on the dye, and short device life.

[0004] There is still much room for improvement in the luminescence performance of existing organic electroluminescent materials, and the industry urgently needs new stable and efficient luminescent material systems to meet commercial requirements. Therefore, designing organic electroluminescent materials with high color purity, high efficiency, and longer service life to achieve true high-quality full-color OLED displays remains an urgent problem in this field. Summary of the Invention

[0005] The object of the present invention is to solve the problem of the lack of luminescent materials with high stability, high efficiency, and narrow spectral bands in the prior art, and to provide a new type of polycyclic aromatic compound. Such materials have high stability and luminescence color purity, and have high efficiency when applied in electroluminescent devices.

[0006] Specifically, the present invention provides a polycyclic aromatic compound having a structure represented by the following formula (1):

[0007]

[0008] R2 and R3 are not connected or are connected to form a ring, and R4 and R5 are not connected or are connected to form a ring;

[0009] Ring A, ring B, and ring C are each independently selected from an unsubstituted or R'-substituted C6-C60 aromatic ring and an unsubstituted or R'-substituted C3-C60 heteroaromatic ring, and adjacent R's are not connected or are connected to form a ring;

[0010] And at least one of ring A, ring B, and ring C is fused and connected to a group having a structure represented by formula (2);

[0011]

[0012] In formula (2), the dotted line represents that formula (2) is condensed at any fusible position in ring A, ring B, or ring C;

[0013] Q is selected from O, S, Se, NR6, CR7R8, or SiR9R 10 ;

[0014] R7 and R8 are not connected or are connected to form a ring, and R9 and R 10 are not connected or are connected to form a ring;

[0015] Z1, Z2, Z3, Z4, Z5, and Z6 are each independently CR 11 or N, and adjacent R 11 are not connected or are connected to form a ring;

[0016] R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 are each independently selected from an unsubstituted or R'-substituted C1-C30 linear alkyl group, an unsubstituted or R'-substituted C3-C20 cycloalkyl group, an unsubstituted or R'-substituted C7-C30 aralkyl group, an unsubstituted or R'-substituted C1-C30 alkoxy group, an unsubstituted or R'-substituted C2-C30 aliphatic hydrocarbon amine group, an unsubstituted or R'-substituted C4-C30 cyclic aliphatic hydrocarbon amine group, an unsubstituted or R'-substituted C6-C30 arylamine group, an unsubstituted or R'-substituted C3-C30 heteroarylamine group, an unsubstituted or R'-substituted C6-C30 aryloxy group, an unsubstituted or R'-substituted C6-C60 arylboron group, an unsubstituted or R'-substituted C6-C60 aryl group, and an unsubstituted or R'-substituted C3-C60 heteroaryl group;

[0017] R 11Selected from one of hydrogen, deuterium, halogen, cyano, unsubstituted or R'-substituted C1-C30 linear alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C7-C30 aralkyl, unsubstituted or R'-substituted C1-C30 alkoxy, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C6-C60 arylboron, unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl;

[0018] R' is selected from one of deuterium, halogen, cyano, C1-C20 linear alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, C6-C30 arylboron, C3-C30 heteroaryl or a combination of two of them.

[0019] In this specification, the "substituted or unsubstituted" group may be substituted with one substituent or multiple substituents. When there are multiple substituents, they may be selected from different substituents. When the same expression is involved in the present invention, it has the same meaning, and the selection range of the substituents is as shown above and will not be elaborated one by one.

[0020] In this specification, the expression of Ca-Cb represents that the group has a carbon atom number of a-b. Generally speaking, unless otherwise specified, the carbon atom number does not include the carbon atom number of the substituents.

[0021] In this specification, the expression of a ring structure with a "-" drawn across it indicates that the bonding site is at any position on the ring structure where bonding can occur.

[0022] In this specification, "independently of each other" means that when the subject has multiple ones, they can be the same or different from each other.

[0023] In the present invention, for the expression of chemical elements, unless otherwise specified, it usually includes the concept of its isotopes. For example, the expression of "hydrogen (H)" includes its isotopes 1 H (protium or H), 2 H (deuterium or D); carbon (C) includes 12 C, 13 C, etc., and will not be elaborated further.

[0024] The heteroatoms in the present invention usually refer to atoms or atomic groups selected from N, O, Si, P, S and Se, preferably selected from N, O, S.

[0025] In this specification, examples of halogens include: fluorine, chlorine, bromine, iodine, etc.

[0026] In the present invention, unless otherwise specified, aryl and heteroaryl both include monocyclic and polycyclic cases.

[0027] In the present invention, the C6-C60 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56 or C58, etc.

[0028] The C3-C60 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56 or C58, etc.

[0029] The C1-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0030] The C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

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

[0032] The C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0033] The C2-C10 can all be C2, C3, C4, C5, C6, C7, C8, C9 or C10.

[0034] In the present invention, the substituted or unsubstituted C6-C60 aryl group includes monocyclic aryl groups and fused-ring aryl groups, preferably C6-C30 aryl groups, and more preferably C6-C20 aryl groups. The so-called monocyclic aryl group refers to a molecule containing at least one phenyl group. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and are connected by single bonds. Exemplarily, such as: phenyl group, biphenyl group, terphenyl group, etc. Specifically, the biphenyl group includes 2-biphenyl group, 3-biphenyl group, and 4-biphenyl group; 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 fused-ring aryl group refers to a group in which the molecule contains at least two aromatic rings and the aromatic rings are not independent of each other but are fused together by sharing two adjacent carbon atoms. Exemplarily, such as: naphthyl group, anthryl group, phenanthryl group, indenyl group, fluorenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, perylenyl group, -yl group, tetraphenylenyl group and their derivative groups, etc. The naphthyl group includes 1-naphthyl group or 2-naphthyl group; the anthryl group is selected from 1-anthryl group, 2-anthryl group, and 9-anthryl group; the fluorenyl group is selected from 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, and 9-fluorenyl group; the pyrenyl group is selected from 1-pyrenyl group, 2-pyrenyl group, and 4-pyrenyl group; the tetraphenylenyl group is selected from 1-tetraphenylenyl group, 2-tetraphenylenyl group, and 9-tetraphenylenyl group. The derivative groups of fluorene are selected from 9,9-dimethylfluorenyl group, 9,9-diethylfluorenyl group, 9,9-dipropylfluorenyl group, 9,9-dibutylfluorenyl group, 9,9-dipentylfluorenyl group, 9,9-dihexylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-dinaphthylfluorenyl group, 9,9'-spirobifluorenyl group, and benzofluorenyl group.

[0035] The C3-C60 heteroaryl group mentioned in the present invention includes monocyclic heteroaryl groups and fused-ring heteroaryl groups, preferably C3-C30 heteroaryl groups, more preferably C4-C20 heteroaryl groups, and even more preferably C5-C12 heteroaryl groups. The monocyclic heteroaryl group refers to a molecule containing at least one heteroaryl group. When the molecule contains a heteroaryl group and other groups (such as aryl group, heteroaryl group, alkyl group, etc.), the heteroaryl group and other groups are independent of each other and are connected by single bonds. Examples of the monocyclic heteroaryl group include: furyl group, thienyl group, pyrrolyl group, pyridyl group, etc. The fused-ring heteroaryl group refers to a group in which the molecule contains at least one heteroaromatic ring and an aromatic ring (heteroaromatic ring or aromatic ring), and the two are not independent of each other but are fused together by sharing two adjacent atoms. Examples of the fused-ring heteroaryl group include: benzofuryl group, benzothienyl group, isobenzofuryl group, indolyl group, dibenzofuryl group, dibenzothienyl group, carbazolyl group, acridinyl group, isobenzofuryl group, isobenzothienyl group, benzocarbazolyl group, azacarbazolyl group, phenothiazinyl group, phenazinyl group, 9-phenylcarbazolyl group, 9-naphthylcarbazolyl group, dibenzocarbazolyl group, indolocarbazolyl group, etc.

[0036] Specific examples of the arylene group in the present invention include divalent groups obtained by removing one hydrogen atom from the examples of the above-mentioned aryl groups. The number of carbon atoms in the arylene group includes, but is not limited to, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc. Specific examples of the heteroarylene group in the present invention include divalent groups obtained by removing one hydrogen atom from the examples of the above-mentioned heteroaryl groups.

[0037] The aryloxy group in the present invention includes monovalent groups composed of the above-mentioned aryl group, heteroaryl group and oxygen.

[0038] In the present invention, arylamino represents a group formed by substituting one or two hydrogen atoms on the amino group with aryl groups, wherein the connecting site of the arylamino group can be connected to the aryl group in the arylamino group or to the N in the arylamino group, and the exemplary number of carbon atoms and specific groups of the aryl group in the arylamino group are the same as those above.

[0039] Examples of the C6-C30 arylamino group mentioned in the present invention include, for example: phenylamino, methylphenylamino, naphthylamino, anthrylamino, phenanthrylamino, biphenylamino, etc.

[0040] Examples of the C3-C30 heteroarylamino group mentioned in the present invention include, for example: pyridylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0041] In the present invention, the linear alkyl group, unless otherwise specified, includes straight-chain alkyl groups and branched-chain alkyl groups. Specifically, the substituted or unsubstituted C1-C30 linear alkyl group is preferably a substituted or unsubstituted C1-C16 linear alkyl group, more preferably a substituted or unsubstituted C1-C10 linear alkyl group. Examples of the substituted or unsubstituted C1-C10 linear alkyl group include, for example: 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.

[0042] In the present invention, the cycloalkyl group includes monocyclic alkyl groups and polycyclic alkyl groups; wherein, the monocyclic alkyl group refers to an alkyl group containing a single cyclic structure; the polycyclic alkyl group refers to a structure formed by two or more cycloalkyl groups sharing one or more ring carbon atoms; examples of the C3-C20 cycloalkyl group include, for example: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0043] In the present specification, as the substituted or unsubstituted C1-C20 alkoxy group, preferably a substituted or unsubstituted C1-C10 alkoxy group, examples of the C1-C10 alkoxy group include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, etc., among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, and isopentyloxy are preferred, and methoxy is more preferred.

[0044] In the present specification, as the substituted or unsubstituted C1-C20 silyl group, as the substituted or unsubstituted C1-C10 silyl group, examples of the C1-C10 silyl group may be silyl groups substituted by the groups exemplified in the above C1-C10 alkyl groups, and specifically include: methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and other groups.

[0045] In the present specification, the C2-C10 alkenyl group is a hydrocarbon group containing at least 1 C═C double bond, and exemplarily includes but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0046] It should be noted that in the present application, for the convenience of description, the possible functions of each group / feature are described separately, but this does not mean that these groups / features act independently. In fact, the reason for obtaining good performance is essentially the optimized combination of the entire molecule, which is the result of the synergistic effect between each group, rather than the effect of a single group.

[0047] Further preferably, in formula (2), Q is selected from O, S, NR6 or CR7R8;

[0048] R6 is selected from unsubstituted or R'-substituted C6-C60 aryl groups; R7 and R8 are each independently selected from unsubstituted or R'-substituted C1-C10 linear alkyl groups, unsubstituted or R'-substituted C3-C10 cycloalkyl groups, unsubstituted or R'-substituted C1-C10 alkoxy groups, unsubstituted or R'-substituted C6-C30 arylamino groups, unsubstituted or R'-substituted C3-C30 heteroarylamino groups, unsubstituted or R'-substituted C6-C30 aryloxy groups, unsubstituted or R'-substituted C6-C60 aryl groups, and unsubstituted or R'-substituted C3-C60 heteroaryl groups;

[0049] R' is selected from one of deuterium, halogen, cyano, C1-C10 linear alkyl, C3-C10 cycloalkyl, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl;

[0050] In formula (2), at most 3 of Z1-Z6 are N; preferably, at most 1 of Z1-Z6 is N.

[0051] Further preferably, in formula (1), ring A and ring B each independently select a structure shown in formula (3) or formula (4), ring C selects a structure shown in formula (3), and at least one of ring A, ring B, and ring C is fused to a group with a structure shown in formula (2)

[0052]

[0053] In formula (3) and formula (4), the dashed line represents a condensed bicyclic structure containing B and X1 in formula (1), or a condensed bicyclic structure containing B and X2 in formula (1);

[0054] The dashed line in formula (2) represents any condensable position other than the dashed line where formula (2) is condensed to the structure of formula (3) or formula (4);

[0055] In formula (3), Y1, Y2, Y3, and Y4 each independently select CR 12 or N, and adjacent Rs 12 are not connected or are connected to form a ring;

[0056] R 12 each independently selects from hydrogen, deuterium, halogen, cyano, unsubstituted or R''-substituted C1-C30 linear alkyl, unsubstituted or R''-substituted C3-C20 cycloalkyl, unsubstituted or R''-substituted C7-C30 aralkyl, unsubstituted or R''-substituted C1-C30 alkoxy, unsubstituted or R''-substituted C2-C30 aliphatic hydrocarbon amino group, unsubstituted or R''-substituted C4-C30 cyclic aliphatic hydrocarbon amino group, unsubstituted or R''-substituted C6-C30 arylamino group, unsubstituted or R''-substituted C3-C30 heteroarylamino group, unsubstituted or R''-substituted C6-C30 aryloxy, unsubstituted or R''-substituted C6-C60 arylboron group, unsubstituted or R''-substituted C6-C60 aryl, and unsubstituted or R''-substituted C3-C60 heteroaryl;

[0057] In formula (4), X3 selects O, S, Se, NR 13 , CR 14 R 15 ;

[0058] The said R 14 and R 15Disconnected or connected in a ring;

[0059] R 13 , R 14 and R 15 are each independently selected from an unsubstituted or R”-substituted C1-C30 linear alkyl group, an unsubstituted or R”-substituted C3-C20 cycloalkyl group, an unsubstituted or R”-substituted C7-C30 aralkyl group, an unsubstituted or R”-substituted C1-C30 alkoxy group, an unsubstituted or R”-substituted C2-C30 aliphatic hydrocarbon amine group, an unsubstituted or R”-substituted C4-C30 cyclic aliphatic hydrocarbon amine group, an unsubstituted or R”-substituted C6-C30 arylamine group, an unsubstituted or R”-substituted C3-C30 heteroarylamine group, an unsubstituted or R”-substituted C6-C30 aryloxy group, an unsubstituted or R”-substituted C6-C60 arylboron group, an unsubstituted or R”-substituted C6-C60 aryl group, and an unsubstituted or R”-substituted C3-C60 heteroaryl group;

[0060] Ring D is independently selected from one of the following unsubstituted or R”-substituted groups: benzene ring, biphenyl ring, terphenyl ring, naphthalene ring, anthracene ring, phenanthrene ring, indene ring, fluorene ring, fluoranthene ring, triphenylene ring, pyrene ring, perylene ring, ring, tetracene ring, furan ring, thiophene ring, pyrrole ring, benzofuran ring, benzothiophene ring, isobenzofuran ring, indole ring, dibenzofuran ring, dibenzothiophene ring, or carbazole ring, and adjacent R” groups are not connected or are connected in a ring;

[0061] Each of the above R” is independently selected from one of deuterium, halogen, cyano, a C1-C20 linear alkyl group, a C3-C20 cycloalkyl group, a C1-C10 alkoxy group, a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C30 aryloxy group, a C6-C30 aryl group, a substituted or unsubstituted C6-C30 arylboron group, and a C3-C30 heteroaryl group;

[0062] More preferably, ring A, ring B, and ring C are each independently selected from one of the following unsubstituted or R'-substituted groups: benzene ring, naphthalene ring, anthracene ring, fluorene ring, cyclopentadiene ring, indene ring, furan ring, benzofuran ring, dibenzofuran ring, indole ring, benzindole ring, carbazole ring, indolocarbazole ring, thiophene ring, benzothiophene ring, dibenzothiophene ring;

[0063] Adjacent R' groups are not connected or are connected in a ring;

[0064] Preferably, ring A and ring B are each independently selected from one of the following unsubstituted or R'-substituted groups: benzene ring, naphthalene ring, cyclopentadiene ring, indene ring, furan ring, benzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, and ring C is selected from one of the following unsubstituted or R'-substituted groups: benzene ring, naphthalene ring, fluorene ring;

[0065] More preferably, each of ring A and ring B is independently selected from one of the following unsubstituted or R'-substituted groups: benzene ring, indene ring, benzofuran ring, benzothiophene ring, and ring C is an unsubstituted or R'-substituted benzene ring.

[0066] R' is selected from one of deuterium, halogen, cyano, C1-C20 linear alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, substituted or unsubstituted C6-C30 arylboron, C3-C30 heteroaryl, or a combination of two of them.

[0067] Furthermore, the polycyclic aromatic compound of the present invention has a structure shown in any one of Formulas 1-1 to 1-24:

[0068]

[0069]

[0070] R a 、R b 、R c represent monosubstituted groups to the maximum allowable number of substituted groups. Between adjacent R a s, between adjacent R b s, between adjacent R c s, they are not connected or are connected to form a ring. R a 、R b 、R c are each independently selected from hydrogen, deuterium, halogen, cyano, C1-C20 linear alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, C6-C30 arylboron, C3-C30 heteroaryl, or a combination of two of them;

[0071] X1 and X2 are each independently O, S, NR1, CR2R3 or SiR4R5;

[0072] Q1 and Q2 are each independently selected from O, S, Se, NR6, CR7R8 or SiR9R 10 ;

[0073] X3 and X4 are each independently selected from O, S, NR 13 、CR 14 R 15 ;

[0074] Z1, Z2, Z3, Z4, Z5 and Z6 are each independently CR11 or N, R 11 selected from one or a combination of two of hydrogen, deuterium, halogen, cyano, C1-C20 linear alkyl, C3-C20 cycloalkyl, C7-C30 aralkyl, C1-C10 alkoxy, C6-C30 aryloxy, C6-C30 aryl, C6-C30 arylboron, and C3-C30 heteroaryl;

[0075] Preferably, in Formulas 1-1 to 1-24, X1 and X2 are each independently selected from O, S, or NR1; R1 is selected from unsubstituted or R'-substituted C6-C60 aryl; R' is selected from one of deuterium, halogen, cyano, C1-C10 linear alkyl, C3-C10 cycloalkyl, C6-C30 aryloxy, C6-C30 aryl, and C3-C30 heteroaryl;

[0076] Preferably, X3 and X4 are each independently selected from O, S, or CR 14 R 15 .

[0077] Furthermore, in Formulas 1-1 to 1-24,

[0078] the R a , R b , R c are each independently selected from one of hydrogen, deuterium, halogen, cyano, C1-C10 linear alkyl, C3-C10 cycloalkyl, C7-C30 aralkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, and C3-C60 heteroaryl;

[0079] Z1, Z2, Z3, Z4, Z5, and Z6 are each independently CR 11 or N, R 11 is selected from one of hydrogen, deuterium, halogen, methyl, ethyl, propyl, butyl, tert-butyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, pyrenyl, thiophenyl, benzothiophenyl, bithiophenyl, terthiophenyl, dithienophenyl, dibenzothiophenyl, furyl, and benzofuryl;

[0080] Preferably, in Formulas 1-1 to 1-24, the R a , R b , R cEach independently selected from hydrogen, deuterium, halogen, methyl, ethyl, propyl, butyl, tert-butyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, pyrenyl, thienyl, benzothienyl, bithiophenyl, terthiophenyl, dithienophenyl, dibenzothiophenyl, furyl, benzofuryl, thiazolyl, benzothiazolyl, isothiazolyl, benzisothiazolyl, pyrrolyl, benzopyrrolyl, imidazolyl, benzimidazolyl, pyrazolyl, benzopyrazolyl, oxazolyl, benzoxazolyl, isoxazolyl, benzisoxazolyl, pyridyl, pyrimidinyl, benzopyrimidinyl, pyrazinyl, benzopyrazinyl, pyridazinyl, benzopyridazinyl, quinolinyl, isoquinolinyl, purinyl, pteridinyl, pyridazinyl, indolyl, carbazolyl.

[0081] Most preferably, the compounds of general formula (1) of the present invention can preferably yield the following specific structural compounds, which are only representative and do not limit the scope of the present invention.

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101] Wherein -Ad represents 1 - adamantyl group.

[0102] In the polycyclic aromatic compound provided by the present invention, the group shown in formula (2) has appropriate electron - donating properties and can cooperate with the X1 - B - X2 core. As a result, the spatial distributions of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of such compounds have the characteristics that i) they are spaced apart and distributed on the π - framework atoms, and ii) the orbital centroids are close to each other in space, showing multiple resonance characteristics. Therefore, such compounds have a narrow full - width at half - maximum (FWHM) and high color purity. Moreover, the framework composed of fused aromatic rings endows the molecules of such compounds with a certain rigidity, which can effectively inhibit the vibration and rotation of the molecules, thereby reducing the reorganization energy of the molecular excited state and also contributing to reducing the FWHM.

[0103] At the same time, the group shown in formula (2) endows such compounds with a low triplet excited state energy level and a large singlet - triplet excited state energy difference, making the molecules of such compounds exhibit pure fluorescence emission characteristics. The low triplet excited state energy level reduces the luminescence quenching and molecular degradation caused by processes such as triplet - triplet annihilation (TTA), singlet - triplet annihilation (STA), and triplet - polaron annihilation (TPA). Therefore, the OLED devices using such compounds have the advantages of high luminous efficiency and long device lifetime.

[0104] Furthermore, when at least one of ring A or ring B is fused to connect the group of the structure shown in formula (2), due to the expanded π - conjugated plane of the polycyclic aromatic organic compound, the oscillator strength between the first singlet excited state and the ground state is greatly increased, achieving high luminous efficiency. In particular, when Q = O, S, its electron - donating property will further increase the oscillator strength of the molecule; when ring A or ring B is selected from the structure shown in formula (4), the rigid planar structure of the molecule also increases the oscillator strength between the first singlet excited state and the ground state, thereby further improving the luminous efficiency and device efficiency of the compound.

[0105] The preparation process of the polycyclic aromatic organic compound is simple and easy to operate, and the raw materials are easily available, suitable for mass production and amplification. As a material for the light - emitting layer in organic electroluminescent devices, it can improve the lifetime and efficiency of organic electroluminescent devices, enabling the devices to achieve excellent luminous effects.

[0106] In the second aspect, the present invention provides an application of a polycyclic aromatic compound as described in the first aspect, and the organic compound is applied to organic electronic devices.

[0107] Preferably, the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, an illumination element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner, or an electronic paper, and more preferably an organic electroluminescent device.

[0108] In a third aspect, the present invention provides an organic electroluminescent device, which includes a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode; and the organic layer includes at least one polycyclic aromatic compound as described in the first aspect. Detailed implementation manners

[0109] The technical solution of the present invention will be further described below through specific implementation manners. Those skilled in the art should understand that the embodiments are only for helping to understand the present invention and should not be regarded as specific limitations to the present invention.

[0110] In a specific implementation manner, the polycyclic aromatic organic compound can be prepared through the following synthetic route:

[0111]

[0112] Among them, ring A, ring B, ring C, X1, and X2 have the same defined ranges as those in formula (1).

[0113] The following will detail the specific preparation methods of the boron and nitrogen-containing organic compounds of the present invention with multiple synthesis examples as illustrations, but the preparation methods of the present invention are not limited to these synthesis examples.

[0114] It should be noted that obtaining the polycyclic aromatic organic compound is not limited to the synthesis methods and raw materials used in the present invention. Those skilled in the art can also select other methods or routes to obtain the polycyclic aromatic organic compound proposed by the present invention. The compounds for which the synthesis methods are not mentioned in the present invention are all raw material products obtained through commercial channels or are self-made from these raw material products according to well-known methods.

[0115] The solvents and reagents used in the present invention can all be purchased from the chemical product market.

[0116] Synthesis Example 1: Synthesis of Compound M73

[0117]

[0118] In this synthesis example, Compound M73 is synthesized according to the following scheme.

[0119] 2.96g (10mmol) of 3-bromo-5-iodotoluene, 3.23g (12mmol) of N-p-methylphenylbenzo[kl]xanthene-9-amine, 2.08g (15mmol) of potassium carbonate, and 0.32g (5mmol) of activated copper powder were added to a 250mL three-necked flask in sequence, followed by 120mL of o-dichlorobenzene. The gas in the three-necked flask was replaced with nitrogen, and then refluxed and stirred for 24h under closed conditions. After the reaction was complete, when the reaction system was cooled to room temperature, the reaction solution was filtered under reduced pressure, and the filter cake was washed with dichloromethane solvent. The solution obtained after filtration was collected and evaporated to remove the solvent. The spin-dried product was then separated by column chromatography, and the eluent and ratio used were dichloromethane: petroleum ether = 1:4 (volume ratio). 4.04g of light yellow solid was obtained by column chromatography, and the yield was 82%.

[0120] The intermediate 3.94g (8mmol), di(4-methylphenyl)amine 1.89g (9.6mmol), palladium acetate 0.05g (0.2mmol), tri-tert-butylphosphine tetrafluoroborate 0.17g (0.6mmol), sodium tert-butoxide 0.78g (8mmol) were added to a 250mL three-necked flask in sequence, followed by 120mL toluene. The gas in the three-necked flask was replaced with nitrogen, and then refluxed and stirred for 2h under closed conditions. After the reaction was completed, when the reaction system was cooled to room temperature, the reaction solution was filtered under reduced pressure, and the filter cake was washed with dichloromethane solvent. The solution obtained after filtration was collected and evaporated to remove the solvent. The spin-dried product was then separated by column chromatography, and the eluent and ratio used were dichloromethane: petroleum ether = 1:4 (volume ratio). 3.70g of light yellow solid was obtained by column chromatography, and the yield was 76%.

[0121] Add 3.65g (6mmol) of the intermediate obtained in the previous step, 2.26g (9mmol) of boron tribromide and 120mL of o-dichlorobenzene into a 250mL three-necked flask, and heat to 180℃ for 24h under nitrogen protection. After column chromatography separation and recrystallization, 2.37g of yellow powder solid was obtained with a yield of 64%. MALDI-TOF-MS results: molecular ion peak: 616.62. Elemental analysis results: theoretical value: C, 85.71; H, 5.39; B, 1.75; N, 4.54; O, 2.59. Experimental value: C, 85.73; H, 5.40; B, 1.73; N, 4.55; O, 2.57.

[0122] Synthesis Example 2: Synthesis of Compound M74

[0123] This example is basically the same as Synthesis Example 1, except that: in this example, N-p-methylphenylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-methylphenylbenzo[kl]thioxanthen-9-amine. MALDI-TOF-MS result: molecular ion peak: 632.59. Elemental analysis result: theoretical values: C, 83.54; H, 5.26; B, 1.71; N, 4.43; S, 5.07. Experimental values: C, 83.52; H, 5.28; B, 1.72; N, 4.42; S, 5.08.

[0124] Synthesis Example 3: Synthesis of Compound M75

[0125] This example is basically the same as Synthesis Example 1, except that: in this example, N-p-methylphenylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-methylphenylbenzo[kl]selenoxanthen-9-amine. MALDI-TOF-MS result: molecular ion peak: 680.19. Elemental analysis result: theoretical values: C, 77.77; H, 4.90; B, 1.59; N, 4.12; Se, 11.62. Experimental values: C, 77.79; H, 4.98; B, 1.59; N, 4.13; Se, 11.61.

[0126] Synthesis Example 4: Synthesis of Compound M76

[0127] This example is basically the same as Synthesis Example 1, except that: in this example, N-p-methylphenylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of 7,7-dimethyl-N-p-methylphenyl-7H-benzo[de]anthracen-9-amine. MALDI-TOF-MS result: molecular ion peak: 642.32. Elemental analysis result: theoretical values: C, 87.84; H, 6.12; B, 1.68; N, 4.36. Experimental values: C, 87.86; H, 6.12; B, 1.68; N, 4.34.

[0128] Synthesis Example 5: Synthesis of Compound M83

[0129] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 784.84. Elemental analysis result: theoretical values: C, 85.70; H, 7.32; B, 1.38; N, 3.57; O, 2.04. Experimental values: C, 85.73; H, 7.31; B, 1.32; N, 3.51; O, 2.05.

[0130] Synthesis Example 6: Synthesis of Compound M84

[0131] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 800.43. Elemental analysis result: theoretical values: C, 83.98; H, 7.15; B, 1.36; N, 3.51; S, 4.00. Experimental values: C, 83.98; H, 7.17; B, 1.35; N, 3.50; S, 4.00.

[0132] Synthesis Example 7: Synthesis of Compound M85

[0133] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenyl-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 810.51. Elemental analysis result: theoretical values: C, 87.38; H, 7.83; B, 1.33; N, 3.45. Experimental values: C, 87.35; H, 7.85; B, 1.34; N, 3.44.

[0134] Synthesis Example 8: Synthesis of Compound M86

[0135] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl)benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 838.50. Elemental analysis result: theoretical values: C, 85.90; H, 7.57; B, 1.29; N, 3.34; O, 1.91. Experimental values: C, 85.94; H, 7.55; B, 1.29; N, 3.33; O, 1.90.

[0136] Synthesis Example 9: Synthesis of Compound M87

[0137] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl)benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 854.48. Elemental analysis result: theoretical values: C, 84.28; H, 7.43; B, 1.26; N, 3.28; S, 3.75. Experimental values: C, 84.28; H, 7.44; B, 1.26; N, 3.27; S, 3.75.

[0138] Synthesis Example 10: Synthesis of Compound M88

[0139] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalenyl)-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 864.56. Elemental analysis result: theoretical values: C, 87.47; H, 8.04; B, 1.25; N, 3.24. Experimental values: C, 87.47; H, 8.06; B, 1.24; N, 3.23.

[0140] Synthesis Example 11: Synthesis of Compound M95

[0141] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 6-(3-bromo-5-iodophenyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 914.53. Elemental analysis result: theoretical values: C, 86.63; H, 7.38; B, 1.18; N, 3.06; O, 1.75. Experimental values: C, 86.63; H, 7.36; B, 1.18; N, 3.08; O, 1.75.

[0142] Synthesis Example 12: Synthesis of Compound M96

[0143] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 6-(3-bromo-5-iodophenyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 930.51. Elemental analysis result: theoretical values: C, 85.13; H, 7.25; B, 1.16; N, 3.01; S, 3.44. Experimental values: C, 85.13; H, 7.25; B, 1.14; N, 3.01; S, 3.46.

[0144] Synthesis Example 13: Synthesis of Compound M97

[0145] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 6-(3-bromo-5-iodophenyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 940.59. Elemental analysis result: theoretical values: C, 88.06; H, 7.82; B, 1.15; N, 2.98. Experimental values: C, 88.08; H, 7.82; B, 1.14; N, 2.97.

[0146] Synthesis Example 14: Synthesis of Compound M98

[0147] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene; N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)benzo[kl]xanthen-9-amine; and bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of 4-tert-butyl-N-4-(2-phenyl-2-propyl)phenylaniline. MALDI-TOF-MS result: molecular ion peak: 900.52. Elemental analysis result: theoretical values: C, 86.64; H, 7.27; B, 1.20; N, 3.11; O, 1.78. Experimental values: C, 86.66; H, 7.25; B, 1.22; N, 3.10; O, 1.77.

[0148] Synthesis Example 15: Synthesis of Compound M99

[0149] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene; N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)benzo[kl]thioxanthen-9-amine; and bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of 4-tert-butyl-N-4-(2-phenyl-2-propyl)phenylaniline. MALDI-TOF-MS result: molecular ion peak: 916.50. Elemental analysis result: theoretical values: C, 85.13; H, 7.14; B, 1.18; N, 3.05; S, 3.50. Experimental values: C, 85.15; H, 7.16; B, 1.17; N, 3.03; S, 3.49.

[0150] Synthesis Example 16: Synthesis of Compound M101

[0151] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene; N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(3,5-di-tert-butylphenyl)benzo[kl]xanthen-9-amine; and bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 840.52. Elemental analysis result: theoretical values: C, 85.69; H, 7.79; B, 1.29; N, 3.33; O, 1.90. Experimental values: C, 85.68; H, 7.79; B, 1.27; N, 3.33; O, 1.93.

[0152] Synthesis Example 17: Synthesis of Compound M102

[0153] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene; N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(3,5-di-tert-butylphenyl)benzo[kl]thioxanthen-9-amine; and bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 856.50. Elemental analysis result: theoretical values: C, 84.08; H, 7.64; B, 1.26; N, 3.27; S, 3.74. Experimental values: C, 84.08; H, 7.66; B, 1.26; N, 3.25; S, 3.74.

[0154] Synthesis Example 18: Synthesis of Compound M103

[0155] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene; N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(3,5-di-tert-butylphenyl)-7,7-dimethyl-7H-benzo[de]anthracen-9-amine; and bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 866.57. Elemental analysis result: theoretical values: C, 87.27; H, 8.25; B, 1.25; N, 3.23. Experimental values: C, 87.29; H, 8.25; B, 1.24; N, 3.22.

[0156] Synthesis Example 19: Synthesis of Compound M104

[0157] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-biphenylyl)benzo[kl]xanthen-9-amine. Di(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of di(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 804.43. Elemental analysis result: theoretical values: C, 86.55; H, 6.64; B, 1.34; N, 3.48; O, 1.99. Experimental values: C, 86.55; H, 6.66; B, 1.34; N, 3.46; O, 1.99.

[0158] Synthesis Example 20: Synthesis of Compound M105

[0159] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-biphenylyl)benzo[kl]thioxanthen-9-amine. Di(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of di(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 820.40. Elemental analysis result: theoretical values: C, 84.86; H, 6.51; B, 1.32; N, 3.41; S, 3.91. Experimental values: C, 84.84; H, 6.51; B, 1.32; N, 3.43; S, 3.91.

[0160] Synthesis Example 21: Synthesis of Compound M110

[0161] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 972.61. Elemental analysis result: theoretical values: C, 86.39; H, 7.98; B, 1.11; N, 2.88; O, 1.64. Experimental values: C, 86.37; H, 7.99; B, 1.12; N, 2.89; O, 1.63.

[0162] Synthesis Example 22: Synthesis of Compound M111

[0163] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 988.59. Elemental analysis result: theoretical values: C, 84.99; H, 7.85; B, 1.09; N, 2.83; S, 3.24. Experimental values: C, 84.99; H, 7.87; B, 1.09; N, 2.81; S, 3.24.

[0164] Synthesis Example 23: Synthesis of Compound M112

[0165] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 972.61. Elemental analysis result: theoretical values: C, 86.39; H, 7.98; B, 1.11; N, 2.88; O, 1.64. Experimental values: C, 86.37; H, 7.99; B, 1.12; N, 2.89; O, 1.63.

[0166] Synthesis Example 24: Synthesis of Compound M116

[0167] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(p-tert-butylphenyl)benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)-4-tert-butylaniline. MALDI-TOF-MS result: molecular ion peak: 972.61. Elemental analysis result: theoretical values: C, 86.39; H, 7.98; B, 1.11; N, 2.88; O, 1.64. Experimental values: C, 86.37; H, 7.99; B, 1.12; N, 2.89; O, 1.63.

[0168] Synthesis Example 25: Synthesis of Compound M117

[0169] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(p-tert-butylphenyl)benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)-4-tert-butylaniline. MALDI-TOF-MS result: molecular ion peak: 988.59. Elemental analysis result: theoretical values: C, 84.99; H, 7.85; B, 1.09; N, 2.83; S, 3.24. Experimental values: C, 84.97; H, 7.85; B, 1.09; N, 2.85; S, 3.24.

[0170] Synthesis Example 26: Synthesis of Compound M119

[0171] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-diphenylaminoiodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(p-tert-butylphenyl)benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)-4-tert-butylaniline. MALDI-TOF-MS result: molecular ion peak: 1083.62. Elemental analysis result: theoretical values: C, 86.40; H, 7.25; B, 1.00; N, 3.88; O, 1.48. Experimental values: C, 86.45; H, 7.25; B, 1.00; N, 3.85; O, 1.46.

[0172] Synthesis Example 27: Synthesis of Compound M120

[0173] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-diphenylaminoiodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(p-tert-butylphenyl)benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)-4-tert-butylaniline. MALDI-TOF-MS result: molecular ion peak: 1099.60. Elemental analysis result: theoretical values: C, 85.14; H, 7.15; B, 0.98; N, 3.82; S, 2.91. Experimental values: C, 85.17; H, 7.15; B, 0.95; N, 3.82; S, 2.91.

[0174] Synthesis Example 28: Synthesis of Compound M121

[0175] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-diphenylaminoiodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(p-tert-butylphenyl)-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)-4-tert-butylaniline. MALDI-TOF-MS result: molecular ion peak: 1109.68. Elemental analysis result: theoretical values: C, 87.62; H, 7.63; B, 0.97; N, 3.78. Experimental values: C, 87.62; H, 7.65; B, 0.95; N, 3.78.

[0176] Synthesis Example 29: Synthesis of Compound M125

[0177] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-diphenylaminoiodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 1083.62. Elemental analysis result: theoretical values: C, 86.40; H, 7.25; B, 1.00; N, 3.88; O, 1.48. Experimental values: C, 86.40; H, 7.28; B, 1.00; N, 3.85; O, 1.48.

[0178] Synthesis Example 30: Synthesis of Compound M126

[0179] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-diphenylaminoiodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 1099.60. Elemental analysis result: theoretical values: C, 85.14; H, 7.15; B, 0.98; N, 3.82; S, 2.91. Experimental values: C, 85.18; H, 7.15; B, 0.96; N, 3.80; S, 2.91.

[0180] Synthesis Example 31: Synthesis of Compound M127

[0181] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-diphenylaminoiodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 1109.68. Elemental analysis result: theoretical values: C, 87.62; H, 7.63; B, 0.97; N, 3.78. Experimental values: C, 87.65; H, 7.63; B, 0.94; N, 3.78.

[0182] Synthesis Example 32: Synthesis of Compound M128

[0183] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-(1-adamantyl)iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl)phenyl)benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)-4-tert-butylaniline. MALDI-TOF-MS result: molecular ion peak: 1180.74. Elemental analysis result: theoretical values: C, 87.43; H, 7.93; B, 0.91; N, 2.37; O, 1.35. Experimental values: C, 87.48; H, 7.90; B, 0.91; N, 2.35; O, 1.35.

[0184] Synthesis Example 33: Synthesis of Compound M129

[0185] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-(1-adamantyl)iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl)phenyl)-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)-4-tert-butylaniline. MALDI-TOF-MS result: molecular ion peak: 1196.72. Elemental analysis result: theoretical values: C, 86.25; H, 7.83; B, 0.90; N, 2.34; S, 2.68. Experimental values: C, 86.25; H, 7.85; B, 0.90; N, 2.32; S, 2.68.

[0186] Synthesis Example 34: Synthesis of Compound M130

[0187] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-(1-adamantyl)iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl)phenyl)-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)-4-tert-butylaniline. MALDI-TOF-MS result: molecular ion peak: 1206.79. Elemental analysis result: theoretical values: C, 88.52; H, 8.26; B, 0.90; N, 2.32. Experimental values: C, 88.55; H, 8.26; B, 0.87; N, 2.32.

[0188] Synthesis Example 35: Synthesis of Compound M131

[0189] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butylphenyl)-7-tert-butyl-benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-dibenzo[b,d]furan-2-amine. MALDI-TOF-MS result: molecular ion peak: 874.47. Elemental analysis result: theoretical values: C, 85.11; H, 6.80; B, 1.24; N, 3.20; O, 3.66. Experimental values: C, 85.15; H, 6.80; B, 1.20; N, 3.20; O, 3.66.

[0190] Synthesis Example 36: Synthesis of Compound M132

[0191] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butylphenyl)-7-tert-butyl-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-dibenzo[b,d]furan-2-amine. MALDI-TOF-MS result: molecular ion peak: 890.44. Elemental analysis result: theoretical values: C, 83.57; H, 6.67; B, 1.21; N, 3.14; O, 1.80; S, 3.60. Experimental values: C, 83.59; H, 6.67; B, 1.21; N, 3.12; O, 1.80; S, 3.60.

[0192] Synthesis Example 37: Synthesis of Compound M133

[0193] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butylphenyl)-7-tert-butyl-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-dibenzo[b,d]furan-2-amine. MALDI-TOF-MS result: molecular ion peak: 900.52. Elemental analysis result: theoretical values: C, 86.64; H, 7.27; B, 1.20; N, 3.11; O, 1.78. Experimental values: C, 86.66; H, 7.27; B, 1.18; N, 3.11; O, 1.78.

[0194] Synthesis Example 38: Synthesis of Compound M137

[0195] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butylphenyl)-6-tert-butyl-benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 840.52. Elemental analysis result: theoretical values: C, 85.69; H, 7.79; B, 1.29; N, 3.33; O, 1.90. Experimental values: C, 85.69; H, 7.74; B, 1.29; N, 3.33; O, 1.95.

[0196] Synthesis Example 39: Synthesis of Compound M138

[0197] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-6-tert-butyl-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 856.50. Elemental analysis result: theoretical values: C, 84.08; H, 7.64; B, 1.26; N, 3.27; S, 3.74. Experimental values: C, 84.08; H, 7.69; B, 1.26; N, 3.22; S, 3.74.

[0198] Synthesis Example 40: Synthesis of Compound M139

[0199] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-6-tert-butyl-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 866.57. Elemental analysis result: theoretical values: C, 87.27; H, 8.25; B, 1.25; N, 3.23. Experimental values: C, 87.32; H, 8.25; B, 1.20; N, 3.23.

[0200] Synthesis Example 41: Synthesis of Compound M140

[0201] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-6-(3,5-di-tert-butylphenyl)-benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 972.61. Elemental analysis result: theoretical values: C, 86.39; H, 7.98; B, 1.11; N, 2.88; O, 1.64. Experimental values: C, 86.39; H, 7.92; B, 1.11; N, 2.94; O, 1.64.

[0202] Synthesis Example 42: Synthesis of Compound M141

[0203] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-6-(3,5-di-tert-butylphenyl)-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 988.59. Elemental analysis result: theoretical values: C, 84.99; H, 7.85; B, 1.09; N, 2.83; S, 3.24. Experimental values: C, 84.97; H, 7.85; B, 1.15; N, 2.83; S, 3.20.

[0204] Synthesis Example 43: Synthesis of Compound M142

[0205] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-6-(3,5-di-tert-butylphenyl)-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 998.66. Elemental analysis result: theoretical values: C, 87.74; H, 8.37; B, 1.08; N, 2.80. Experimental values: C, 87.75; H, 8.37; B, 1.08; N, 2.79.

[0206] Synthesis Example 44: Synthesis of Compound M170

[0207] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of benzo[kl]xanthen-10-ol. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of p-tert-butylphenol. MALDI-TOF-MS result: molecular ion peak: 522.24. Elemental analysis result: theoretical values: C, 82.76; H, 5.98; B, 2.07; O, 9.19. Experimental values: C, 82.78; H, 5.98; B, 2.05; O, 9.19.

[0208] Synthesis Example 45: Synthesis of Compound M171

[0209] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of benzo[kl]thioxanthen-10-ol. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of p-tert-butylphenol. MALDI-TOF-MS result: molecular ion peak: 538.21. Elemental analysis result: theoretical values: C, 80.29; H, 5.80; B, 2.01; O, 5.94; S, 5.95. Experimental values: C, 80.29; H, 5.80; B, 2.05; O, 5.90; S, 5.95.

[0210] Synthesis Example 46: Synthesis of Compound M173

[0211] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of -7,7-dimethyl-7H-benzo[de]anthracen-10-ol. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of p-tert-butylphenol.

[0212] MALDI-TOF-MS result: molecular ion peak: 548.29. Elemental analysis result: theoretical values: C, 85.40; H, 6.80; B, 1.97; O, 5.83. Experimental values: C, 85.37; H, 6.80; B, 1.97; O, 5.86.

[0213] Synthesis Example 47: Synthesis of Compound M176

[0214] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of -7,7-diphenyl-7H-benzo[de]anthracen-10-ol. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of p-tert-butylphenol.

[0215] Results of MALDI-TOF-MS: Molecular ion peak: 672.32. Results of elemental analysis: Theoretical values: C, 87.49; H, 6.14; B, 1.61; O, 4.76. Experimental values: C, 87.49; H, 6.15; B, 1.61; O, 4.75.

[0216] Synthesis Example 48: Synthesis of Compound M179

[0217] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of benzo[kl]xanthene-10-thiol. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of p-tert-butylphenol. Results of MALDI-TOF-MS: Molecular ion peak: 538.21. Results of elemental analysis: Theoretical values: C, 80.29; H, 5.80; B, 2.01; O, 5.94; S, 5.95. Experimental values: C, 80.29; H, 5.83; B, 2.01; O, 5.94; S, 5.92.

[0218] Synthesis Example 49: Synthesis of Compound M180

[0219] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of benzo[kl]thioxanthene-10-thiol. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of p-tert-butylphenol.

[0220] Results of MALDI-TOF-MS: Molecular ion peak: 554.19. Results of elemental analysis: Theoretical values: C, 77.97; H, 5.66; B, 1.95; O, 2.88; S, 11.53. Experimental values: C, 77.97; H, 5.63; B, 1.95; O, 2.88; S, 11.56.

[0221] Synthesis Example 50: Synthesis of Compound M231

[0222] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)benzo[kl]xanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine. MALDI-TOF-MS result: molecular ion peak: 892.55. Elemental analysis result: theoretical values: C, 86.07; H, 7.79; B, 1.21; N, 3.14; O, 1.79. Experimental values: C, 86.09; H, 7.78; B, 1.20; N, 3.15; O, 1.78.

[0223] Synthesis Example 51: Synthesis of Compound M232

[0224] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)benzo[kl]thioxanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine. MALDI-TOF-MS result: molecular ion peak: 908.53. Elemental analysis result: theoretical values: C, 84.55; H, 7.65; B, 1.19; N, 3.08; S, 3.53. Experimental values: C, 84.52; H, 7.66; B, 1.20; N, 3.10; S, 3.52.

[0225] Synthesis Example 52: Synthesis of Compound M234

[0226] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 784.84. Elemental analysis result: theoretical values: C, 85.70; H, 7.32; B, 1.38; N, 3.57; O, 2.04. Experimental values: C, 85.73; H, 7.31; B, 1.32; N, 3.51; O, 2.05.

[0227] Synthesis Example 53: Synthesis of Compound M235

[0228] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 800.43. Elemental analysis result: theoretical values: C, 83.98; H, 7.17; B, 1.35; N, 3.50; S, 4.00. Experimental values: C, 83.98; H, 7.19; B, 1.35; N, 3.48; S, 4.00.

[0229] Synthesis Example 54: Synthesis of Compound M237

[0230] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)benzo[kl]xanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of 4-tert-butyl-N-4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl)phenylaniline. MALDI-TOF-MS result: molecular ion peak: 900.52. Elemental analysis result: theoretical values: C, 86.64; H, 7.27; B, 1.20; N, 3.11; O, 1.78. Experimental values: C, 86.65; H, 7.26; B, 1.22; N, 3.09; O, 1.78.

[0231] Synthesis Example 55: Synthesis of Compound M239

[0232] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-7,7-dimethyl-7H-benzo[de]anthracen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of 4-tert-butyl-N-4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl)phenylaniline. MALDI-TOF-MS result: molecular ion peak: 900.52. Elemental analysis result: theoretical values: C, 86.64; H, 7.27; B, 1.20; N, 3.11; O, 1.78. Experimental values: C, 86.65; H, 7.26; B, 1.22; N, 3.09; O, 1.78.

[0233] Synthesis Example 56: Synthesis of Compound M243

[0234] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-(1-adamantyl) iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butylphenyl)-benzo[kl]xanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 862.50. Elemental analysis result: theoretical values: C, 86.29; H, 7.36; B, 1.25; N, 3.25; O, 1.85. Experimental values: C, 86.35; H, 7.36; B, 1.19; N, 3.25; O, 1.85.

[0235] Synthesis Example 57: Synthesis of Compound M244

[0236] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-(1-adamantyl) iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butylphenyl)-benzo[kl]thioxanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 878.48. Elemental analysis result: theoretical values: C, 84.71; H, 7.22; B, 1.23; N, 3.19; S, 3.65. Experimental values: C, 84.75; H, 7.22; B, 1.23; N, 3.15; S, 3.65.

[0237] Synthesis Example 58: Synthesis of Compound M249

[0238] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)benzo[kl]xanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of 4-tert-butyl-N-4-(2-phenyl-2-propyl)phenylaniline. MALDI-TOF-MS result: molecular ion peak: 972.61. Elemental analysis result: theoretical values: C, 86.39; H, 7.98; B, 1.11; N, 2.88; O, 1.64. Experimental values: C, 86.39; H, 7.97; B, 1.11; N, 2.89; O, 1.64.

[0239] Synthesis Example 59: Synthesis of Compound M250

[0240] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)benzo[kl]thioxanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of 4-tert-butyl-N-4-(2-phenyl-2-propyl)phenylaniline. MALDI-TOF-MS result: molecular ion peak: 988.59. Elemental analysis result: theoretical values: C, 84.99; H, 7.85; B, 1.09; N, 2.83; S, 3.24. Experimental values: C, 84.95; H, 7.87; B, 1.09; N, 2.85; S, 3.24.

[0241] Synthesis Example 60: Synthesis of Compound M252

[0242] This example is basically the same as Synthesis Example 1, except that: in this example, N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)phenyl-4-methylaniline. MALDI-TOF-MS result: molecular ion peak: 888.52. Elemental analysis result: theoretical values: C, 86.46; H, 7.37; B, 1.22; N, 3.15; O, 1.80. Experimental values: C, 86.46; H, 7.37; B, 1.23; N, 3.14; O, 1.80.

[0243] Synthesis Example 61: Synthesis of Compound M253

[0244] This example is basically the same as Synthesis Example 1, except that: in this example, N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]thioxanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)phenyl-4-methylaniline. MALDI-TOF-MS result: molecular ion peak: 904.50. Elemental analysis result: theoretical values: C, 84.93; H, 7.24; B, 1.19; N, 3.10; S, 3.54. Experimental values: C, 84.93; H, 7.27; B, 1.17; N, 3.10; S, 3.53.

[0245] Synthesis Example 62: Synthesis of Compound M266

[0246] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromoiodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of benzo[kl]xanthen-9-ol. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of benzo[b]furan-3-ol. MALDI-TOF-MS result: molecular ion peak: 450.11. Elemental analysis result: theoretical values: C, 80.03; H, 3.36; B, 2.40; O, 14.21. Experimental values: C, 80.05; H, 3.36; B, 2.38; O, 14.21.

[0247] Synthesis Example 63: Synthesis of Compound M267

[0248] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-iodobenzene; N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of benzo[kl]thioxanthen-9-ol; and bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of benzo[b]furan-3-ol. MALDI-TOF-MS result: molecular ion peak: 466.08. Elemental analysis result: theoretical values: C, 77.27; H, 3.24; B, 2.32; O, 10.29; S, 6.88. Experimental values: C, 77.24; H, 3.24; B, 2.32; O, 10.32; S, 6.88.

[0249] Synthesis Example 64: Synthesis of Compound M269

[0250] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-iodobenzene; N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of 7,7-dimethyl-7H-benzo[de]anthracen-9-ol; and bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of benzo[b]thiophen-3-ol. MALDI-TOF-MS result: molecular ion peak: 492.14. Elemental analysis result: theoretical values: C, 80.50; H, 4.30; B, 2.20; O, 6.50; S, 6.51. Experimental values: C, 80.50; H, 4.26; B, 2.20; O, 6.50; S, 6.55.

[0251] Synthesis Example 65: Synthesis of Compound M272

[0252] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodotert-butylbenzene; N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of 7,7-diphenyl-7H-benzo[de]anthracen-9-ol; and bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of benzo[b]thiophen-3-ol.

[0253] MALDI-TOF-MS result: molecular ion peak: 672.23. Elemental analysis result: theoretical values: C, 83.92; H, 4.95; B, 1.61; O, 4.76; S, 4.77. Experimental values: C, 83.96; H, 4.95; B, 1.61; O, 4.72; S, 4.77.

[0254] Synthesis Example 66: Synthesis of Compound M275

[0255] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of 7,7-diphenyl-7H-benzo[de]anthracene-9-thiol. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of 1,1-dimethyl-1H-indene-3-ol.

[0256] Results of MALDI-TOF-MS: Molecular ion peak: 642.22. Results of elemental analysis: Theoretical values: C, 85.98; H, 4.86; B, 1.68; O, 2.49; S, 4.99. Experimental values: C, 85.95; H, 4.86; B, 1.71; O, 2.49; S, 4.99.

[0257] Synthesis Example 67: Synthesis of Compound M295

[0258]

[0259] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-1,1-dimethyl-1H-indene-3-amine. Results of MALDI-TOF-MS: Molecular ion peak: 924.52. Results of elemental analysis: Theoretical values: C, 86.99; H, 7.08; B, 1.17; N, 3.03; O, 1.73. Experimental values: C, 86.97; H, 7.09; B, 1.15; N, 3.04; O, 1.75.

[0260] Synthesis Example 68: Synthesis of Compound M296

[0261] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-1,1-dimethyl-1H-indene-3-amine. MALDI-TOF-MS result: molecular ion peak: 940.50. Elemental analysis result: theoretical values: C, 85.51; H, 6.96; B, 1.15; N, 2.98; S, 3.41. Experimental values: C, 85.52; H, 6.97; B, 1.14; N, 2.96; S, 3.42.

[0262] Synthesis Example 69: Synthesis of Compound M297

[0263] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenyl-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-1,1-dimethyl-1H-indene-3-amine. MALDI-TOF-MS result: molecular ion peak: 950.57. Elemental analysis result: theoretical values: C, 88.39; H, 7.52; B, 1.14; N, 2.95. Experimental values: C, 88.41; H, 7.52; B, 1.12; N, 2.95.

[0264] Synthesis Example 70: Synthesis of Compound M298

[0265] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 824.45. Elemental analysis result: theoretical values: C, 84.45; H, 6.97; B, 1.31; N, 3.40; O, 3.88. Experimental values: C, 84.47; H, 6.96; B, 1.30; N, 3.43; O, 3.85.

[0266] Synthesis Example 71: Synthesis of Compound M299

[0267] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]thiophen-3-amine. MALDI-TOF-MS result: molecular ion peak: 856.41. Elemental analysis result: theoretical values: C, 81.28; H, 6.70; B, 1.26; N, 3.27; S, 7.48. Experimental values: C, 81.25; H, 6.72; B, 1.27; N, 3.25; S, 7.50.

[0268] Synthesis Example 72: Synthesis of Compound M300

[0269] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 866.48. Elemental analysis result: theoretical values: C, 84.50; H, 7.32; B, 1.25; N, 3.23; S, 3.70. Experimental values: C, 84.50; H, 7.35; B, 1.25; N, 3.20; S, 3.70.

[0270] Synthesis Example 73: Synthesis of Compound M301

[0271] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 878.50. Elemental analysis result: theoretical values: C, 84.72; H, 7.22; B, 1.23; N, 3.19; O, 3.64. Experimental values: C, 84.75; H, 7.20; B, 1.24; N, 3.18; O, 3.63.

[0272] Synthesis Example 74: Synthesis of Compound M302

[0273] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene; N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)benzo[kl]thioxanthen-9-amine; and bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 894.48. Elemental analysis result: theoretical values: C, 83.20; H, 7.09; B, 1.21; N, 3.13; O, 1.79; S, 3.58. Experimental values: C, 83.23; H, 7.08; B, 1.20; N, 3.14; O, 1.77; S, 3.58.

[0274] Synthesis Example 75: Synthesis of Compound M303

[0275] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene; N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-7,7-dimethyl-7H-benzo[de]anthracen-9-amine; and bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 904.55. Elemental analysis result: theoretical values: C, 86.26; H, 7.68; B, 1.19; N, 3.10; O, 1.77. Experimental values: C, 86.26; H, 7.69; B, 1.19; N, 3.10; O, 1.76.

[0276] Synthesis Example 76: Synthesis of Compound M307

[0277] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butylbenzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 1012.61. Elemental analysis result: theoretical values: C, 85.35; H, 7.66; B, 1.07; N, 2.76; O, 3.16. Experimental values: C, 85.36; H, 7.66; B, 1.06; N, 2.76; O, 3.16.

[0278] Synthesis Example 77: Synthesis of Compound M308

[0279] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butylbenzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 1028.58. Elemental analysis result: theoretical values: C, 84.02; H, 7.54; B, 1.05; N, 2.72; O, 1.55; S, 3.11. Experimental values: C, 84.02; H, 7.57; B, 1.05; N, 2.72; O, 1.52; S, 3.11.

[0280] Synthesis Example 78: Synthesis of Compound M309

[0281] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 1054.64. Elemental analysis result: theoretical values: C, 85.36; H, 7.93; B, 1.02; N, 2.65; S, 3.04. Experimental values: C, 85.36; H, 7.97; B, 1.02; N, 2.63; S, 3.02.

[0282] Synthesis Example 79: Synthesis of Compound M316

[0283] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-(1-adamantyl)iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl)-benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(2-naphthyl)-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 950.50. Elemental analysis result: theoretical values: C, 85.88; H, 6.68; B, 1.14; N, 2.95; O, 3.36. Experimental values: C, 85.88; H, 6.65; B, 1.17; N, 2.95; O, 3.36.

[0284] Synthesis Example 80: Synthesis of Compound M317

[0285] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-(1-adamantyl)iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalenyl)-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-(2-naphthyl)-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 966.48. Elemental analysis result: theoretical values: C, 84.45; H, 6.57; B, 1.12; N, 2.90; O, 1.65; S, 3.31. Experimental values: C, 84.41; H, 6.57; B, 1.12; N, 2.90; O, 1.65; S, 3.35.

[0286] Synthesis Example 81: Synthesis of Compound M319

[0287] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-(1-adamantyl)iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)-benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 1090.65. Elemental analysis result: theoretical values: C, 85.84; H, 7.67; B, 0.99; N, 2.57; O, 2.93. Experimental values: C, 85.88; H, 7.67; B, 0.95; N, 2.57; O, 2.93.

[0288] Synthesis Example 82: Synthesis of Compound M320

[0289] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-(1-adamantyl)iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 1106.63. Elemental analysis result: theoretical values: C, 84.60; H, 7.55; B, 0.98; N, 2.53; O, 1.44; S, 2.90. Experimental values: C, 84.66; H, 7.55; B, 0.98; N, 2.51; O, 1.40; S, 2.90.

[0290] Synthesis Example 83: Synthesis of Compound M324

[0291] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodotert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-6-tert-butyl-benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-methylphenyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 880.51. Elemental analysis result: theoretical values: C, 84.52; H, 7.44; B, 1.23; N, 3.18; O, 3.63. Experimental values: C, 84.52; H, 7.48; B, 1.21; N, 3.18; O, 3.61.

[0292] Synthesis Example 84: Synthesis of Compound M325

[0293] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-6-tert-butyl-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-methylphenyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 896.49. Elemental analysis result: theoretical values: C, 83.01; H, 7.30; B, 1.21; N, 3.12; O, 1.78; S, 3.57. Experimental values: C, 83.01; H, 7.35; B, 1.21; N, 3.10; O, 1.75; S, 3.57.

[0294] Synthesis Example 85: Synthesis of Compound M327

[0295] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-6-(3,5-di-tert-butylphenyl)-benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-methylphenyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 1012.61. Elemental analysis result: theoretical values: C, 85.35; H, 7.66; B, 1.07; N, 2.76; O, 3.16. Experimental values: C, 85.35; H, 7.68; B, 1.07; N, 2.74; O, 3.16.

[0296] Synthesis Example 86: Synthesis of Compound M328

[0297] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-6-(3,5-di-tert-butylphenyl)-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 1028.58. Elemental analysis result: theoretical values: C, 84.02; H, 7.54; B, 1.05; N, 2.72; O, 1.55; S, 3.11. Experimental values: C, 84.02; H, 7.58; B, 1.05; N, 2.70; O, 1.53; S, 3.11.

[0298] Synthesis Example 87: Synthesis of Compound M330

[0299] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-5-tert-butyl-benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 880.51. Elemental analysis result: theoretical values: C, 84.52; H, 7.44; B, 1.23; N, 3.18; O, 3.63. Experimental values: C, 84.52; H, 7.44; B, 1.25; N, 3.18; O, 3.61.

[0300] Synthesis Example 88: Synthesis of Compound M331

[0301] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-5-tert-butyl-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-methylphenyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 896.49. Elemental analysis result: theoretical values: C, 83.01; H, 7.30; B, 1.21; N, 3.12; O, 1.78; S, 3.57. Experimental values: C, 83.01; H, 7.30; B, 1.21; N, 3.15; O, 1.78; S, 3.54.

[0302] Synthesis Example 89: Synthesis of Compound M332

[0303] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-5-tert-butyl-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-methylphenyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 906.57. Elemental analysis result: theoretical values: C, 86.07; H, 7.89; B, 1.19; N, 3.09; O, 1.76. Experimental values: C, 86.08; H, 7.89; B, 1.18; N, 3.09; O, 1.76.

[0304] Synthesis Example 90: Synthesis of Compound M333

[0305] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodotert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-5-(3,5-di-tert-butylphenyl)-benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-methylphenyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 1012.61. Elemental analysis result: theoretical values: C, 85.35; H, 7.66; B, 1.07; N, 2.76; O, 3.16. Experimental values: C, 85.38; H, 7.66; B, 1.07; N, 2.73; O, 3.16.

[0306] Synthesis Example 91: Synthesis of Compound M334

[0307] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodotert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-5-(3,5-di-tert-butylphenyl)-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-methylphenyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 1028.58. Elemental analysis result: theoretical values: C, 84.02; H, 7.54; B, 1.05; N, 2.72; O, 1.55; S, 3.11. Experimental values: C, 84.08; H, 7.53; B, 1.02; N, 2.72; O, 1.53; S, 3.11.

[0308] Synthesis Example 92: Synthesis of Compound M335

[0309] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-5-(3,5-di-tert-butylphenyl)-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-methylphenyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 1038.66. Elemental analysis result: theoretical values: C, 86.68; H, 8.05; B, 1.04; N, 2.70; O, 1.54. Experimental values: C, 86.69; H, 8.05; B, 1.04; N, 2.70; O, 1.53.

[0310] Synthesis Example 93: Synthesis of Compound M345

[0311] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-4-(3,5-di-tert-butylphenyl)-benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-methylphenyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 1012.61. Elemental analysis result: theoretical values: C, 85.35; H, 7.66; B, 1.07; N, 2.76; O, 3.16. Experimental values: C, 85.39; H, 7.66; B, 1.07; N, 2.72; O, 3.16.

[0312] Synthesis Example 94: Synthesis of Compound M346

[0313] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-4-(3,5-di-tert-butylphenyl)-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 1028.58. Elemental analysis result: theoretical values: C, 84.02; H, 7.54; B, 1.05; N, 2.72; O, 1.55; S, 3.11. Experimental values: C, 84.09; H, 7.53; B, 1.02; N, 2.71; O, 1.53; S, 3.11.

[0314] Synthesis Example 95: Synthesis of Compound M347

[0315] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-5-(3,5-di-tert-butylphenyl)-7,7-diphenyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 1162.69. Elemental analysis result: theoretical values: C, 87.75; H, 7.54; B, 0.93; N, 2.41; O, 1.38. Experimental values: C, 87.75; H, 7.58; B, 0.90; N, 2.41; O, 1.37.

[0316] Synthesis Example 96: Synthesis of Compound M364

[0317] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of benzo[kl]xanthene-10-ol. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of benzo[b]furan-3-ol. MALDI-TOF-MS result: molecular ion peak: 506.17. Elemental analysis result: theoretical values: C, 80.65; H, 4.58; B, 2.13; O, 12.64. Experimental values: C, 80.66; H, 4.58; B, 2.13; O, 12.63.

[0318] Synthesis Example 97: Synthesis of Compound M365

[0319] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of benzo[kl]thioxanthene-10-ol. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of benzo[b]furan-3-ol.

[0320] MALDI-TOF-MS result: molecular ion peak: 522.15. Elemental analysis result: theoretical values: C, 78.17; H, 4.44; B, 2.07; O, 9.19; S, 6.14. Experimental values: C, 78.17; H, 4.42; B, 2.07; O, 9.19; S, 6.16.

[0321] Synthesis Example 98: Synthesis of Compound M371

[0322] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of benzo[kl]xanthene-10-thiol. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of benzo[b]thiophene-3-ol.

[0323] MALDI-TOF-MS result: molecular ion peak: 538.12. Elemental analysis result: theoretical values: C, 75.84; H, 4.31; B, 2.01; O, 5.94; S, 11.91. Experimental values: C, 75.86; H, 4.30; B, 2.00; O, 5.94; S, 11.91.

[0324] Synthesis Example 99: Synthesis of Compound M372

[0325] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of benzo[kl]thioxanthene-10-thiol. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of benzo[b]thiophen-3-ol.

[0326] MALDI-TOF-MS result: Molecular ion peak: 554.10. Elemental analysis result: Theoretical value: C, 73.64; H, 4.18; B, 1.95; O, 2.89; S, 17.34. Experimental value: C, 73.64; H, 4.17; B, 1.95; O, 2.89; S, 17.35.

[0327] Synthesis Example 100: Synthesis of Compound M394

[0328] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 9-(3-bromo-5-iodophenyl)-3,6-di-tert-butyl-9H-carbazole. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-p-methylphenyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: Molecular ion peak: 1045.57. Elemental analysis result: Theoretical value: C, 84.95; H, 6.94; B, 1.03; N, 4.02; O, 3.06. Experimental value: C, 84.97; H, 6.93; B, 1.02; N, 4.04; O, 3.04.

[0329] Synthesis Example 101: Synthesis of Compound M395

[0330] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 9-(3-bromo-5-iodophenyl)-3,6-di-tert-butyl-9H-carbazole. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]thioxanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 1061.55. Elemental analysis result: theoretical values: C, 83.67; H, 6.83; B, 1.02; N, 3.96; O, 1.51; S, 3.02. Experimental values: C, 83.67; H, 6.87; B, 1.02; N, 3.92; O, 1.51; S, 3.02.

[0331] Synthesis Example 102: Synthesis of Compound M396

[0332] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 9-(3-bromo-5-iodophenyl)-3,6-di-tert-butyl-9H-carbazole. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-7,7-dimethyl-7H-benzo[de]anthracen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 1071.62. Elemental analysis result: theoretical values: C, 86.25; H, 7.33; B, 1.01; N, 3.92; O, 1.49. Experimental values: C, 86.25; H, 7.37; B, 1.01; N, 3.90; O, 1.47.

[0333] Synthesis Example 103: Synthesis of Compound M400

[0334] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-methylphenyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 824.45. Elemental analysis result: theoretical values: C, 84.12; H, 4.86; B, 1.68; N, 4.36; O, 4.98. Experimental values: C, 84.10; H, 4.88; B, 1.68; N, 4.37; O, 4.96.

[0335] Synthesis Example 104: Synthesis of Compound M401

[0336] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]thioxanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-methylphenyl-5-tert-butyl-benzo[b]thiophene-3-amine. MALDI-TOF-MS result: molecular ion peak: 856.41. Elemental analysis result: theoretical values: C, 81.28; H, 6.70; B, 1.26; N, 3.27; S, 7.48. Experimental values: C, 81.28; H, 6.75; B, 1.26; N, 3.22; S, 7.48.

[0337] Synthesis Example 105: Synthesis of Compound M402

[0338] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-7,7-diphenyl-7H-benzo[de]anthracen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]thiophen-3-amine. MALDI-TOF-MS result: molecular ion peak: 866.48. Elemental analysis result: theoretical values: C, 84.50; H, 7.32; B, 1.25; N, 3.23; S, 3.70. Experimental values: C, 84.50; H, 7.35; B, 1.25; N, 3.20; S, 3.70.

[0339] Synthesis Example 106: Synthesis of Compound M410

[0340] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-adamantyl-iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)benzo[kl]xanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 1012.61. Elemental analysis result: theoretical values: C, 85.35; H, 7.66; B, 1.07; N, 2.76; O, 3.16. Experimental values: C, 85.38; H, 7.66; B, 1.07; N, 2.73; O, 3.16.

[0341] Synthesis Example 107: Synthesis of Compound M411

[0342] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-adamantyl-iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)benzo[kl]thioxanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 1028.58. Elemental analysis result: theoretical values: C, 84.02; H, 7.54; B, 1.05; N, 2.72; O, 1.55; S, 3.11. Experimental values: C, 84.02; H, 7.54; B, 1.08; N, 2.72; O, 1.52; S, 3.11.

[0343] Synthesis Example 108: Synthesis of Compound M412

[0344] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-adamantyl-iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)-7,7-dimethyl-7H-benzo[de]anthracen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-3-amine. MALDI-TOF-MS result: molecular ion peak: 1038.66. Elemental analysis result: theoretical values: C, 86.68; H, 8.05; B, 1.04; N, 2.70; O, 1.54. Experimental values: C, 86.70; H, 8.03; B, 1.04; N, 2.70; O, 1.54.

[0345] Synthesis Example 109: Synthesis of Compound M448

[0346] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]thiophen-2-amine. MALDI-TOF-MS result: molecular ion peak: 824.45. Elemental analysis result: theoretical values: C, 84.45; H, 6.97; B, 1.31; N, 3.40; O, 3.88. Experimental values: C, 84.45; H, 6.95; B, 1.31; N, 3.42; O, 3.88.

[0347] Synthesis Example 110: Synthesis of Compound M449

[0348] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]thiophen-2-amine. MALDI-TOF-MS result: molecular ion peak: 857.04. Elemental analysis result: theoretical values: C, 81.28; H, 6.70; B, 1.26; N, 3.27; S, 7.48. Experimental values: C, 81.30; H, 6.71; B, 1.25; N, 3.26; S, 7.47.

[0349] Synthesis Example 111: Synthesis of Compound M450

[0350] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]thiophen-2-amine. MALDI-TOF-MS result: molecular ion peak: 866.48. Elemental analysis result: theoretical values: C, 84.50; H, 7.32; B, 1.25; N, 3.23; S, 3.70. Experimental values: C, 84.56; H, 7.32; B, 1.22; N, 3.20; S, 3.70.

[0351] Synthesis Example 112: Synthesis of Compound M451

[0352] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl)-benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-2-amine. MALDI-TOF-MS result: molecular ion peak: 878.50. Elemental analysis result: theoretical values: C, 84.72; H, 7.22; B, 1.23; N, 3.19; O, 3.64. Experimental values: C, 84.72; H, 7.26; B, 1.23; N, 3.19; O, 3.60.

[0353] Synthesis Example 113: Synthesis of Compound M452

[0354] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalenyl)-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-2-amine. MALDI-TOF-MS result: molecular ion peak: 894.48. Elemental analysis result: theoretical values: C, 83.20; H, 7.09; B, 1.21; N, 3.13; O, 1.79; S, 3.58. Experimental values: C, 83.26; H, 7.09; B, 1.20; N, 3.10; O, 1.79; S, 3.56.

[0355] Synthesis Example 114: Synthesis of Compound M453

[0356] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalenyl)-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-2-amine. MALDI-TOF-MS result: molecular ion peak: 904.55. Elemental analysis result: theoretical values: C, 86.26; H, 7.68; B, 1.19; N, 3.10; O, 1.77. Experimental values: C, 86.26; H, 7.67; B, 1.19; N, 3.11; O, 1.77.

[0357] Synthesis Example 115: Synthesis of Compound M457

[0358] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butyl-(3,5-di-tert-butylphenyl)phenyl)-benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-2-amine. MALDI-TOF-MS result: molecular ion peak: 1012.61. Elemental analysis result: theoretical values: C, 85.35; H, 7.66; B, 1.07; N, 2.76; O, 3.16. Experimental values: C, 85.35; H, 7.68; B, 1.07; N, 2.74; O, 3.16.

[0359] Synthesis Example 116: Synthesis of Compound M458

[0360] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butyl-(3,5-di-tert-butylphenyl)phenyl)-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-2-amine. MALDI-TOF-MS result: molecular ion peak: 1028.58. Elemental analysis result: theoretical values: C, 84.02; H, 7.54; B, 1.05; N, 2.72; O, 1.55; S, 3.11. Experimental values: C, 84.02; H, 7.57; B, 1.05; N, 2.70; O, 1.55; S, 3.10.

[0361] Synthesis Example 117: Synthesis of Compound M459

[0362] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butyl-(3,5-di-tert-butylphenyl)phenyl)-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]thiophen-2-amine. MALDI-TOF-MS result: molecular ion peak: 1054.64. Elemental analysis result: theoretical values: C, 85.36; H, 7.93; B, 1.02; N, 2.65; S, 3.04. Experimental values: C, 85.36; H, 7.93; B, 1.02; N, 2.65; S, 3.04.

[0363] Synthesis Example 118: Synthesis of Compound M471

[0364] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-2-amine. MALDI-TOF-MS result: molecular ion peak: 824.45. Elemental analysis result: theoretical values: C, 84.45; H, 6.97; B, 1.31; N, 3.40; O, 3.88. Experimental values: C, 84.48; H, 6.95; B, 1.30; N, 3.42; O, 3.86.

[0365] Synthesis Example 119: Synthesis of Compound M472

[0366] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]thioxanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]thiophen-2-amine. MALDI-TOF-MS result: molecular ion peak: 856.41. Elemental analysis result: theoretical values: C, 81.28; H, 6.70; B, 1.26; N, 3.27; S, 7.48. Experimental values: C, 81.26; H, 6.70; B, 1.26; N, 3.29; S, 7.48.

[0367] Synthesis Example 120: Synthesis of Compound M473

[0368] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]thiophen-2-amine. MALDI-TOF-MS result: molecular ion peak: 866.48. Elemental analysis result: theoretical values: C, 84.50; H, 7.32; B, 1.25; N, 3.23; S, 3.70. Experimental values: C, 84.50; H, 7.32; B, 1.28; N, 3.20; S, 3.70.

[0369] Synthesis Example 121: Synthesis of Compound M482

[0370] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl-2-(3,5-di-tert-butylphenyl)phenyl)-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]furan-2-amine. MALDI-TOF-MS result: molecular ion peak: 1038.66. Elemental analysis result: theoretical values: C, 86.68; H, 8.05; B, 1.04; N, 2.70; O, 1.54. Experimental values: C, 86.68; H, 8.08; B, 1.04; N, 2.70; O, 1.51.

[0371] Synthesis Example 122: Synthesis of Compound M483

[0372] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl-2-(3,5-di-tert-butylphenyl)phenyl)-benzo[kl]xanthen-10-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-p-tolyl-5-tert-butyl-benzo[b]thiophen-2-amine. MALDI-TOF-MS result: molecular ion peak: 1028.58. Elemental analysis result: theoretical values: C, 84.02; H, 7.54; B, 1.05; N, 2.72; O, 1.55; S, 3.11. Experimental values: C, 84.02; H, 7.54; B, 1.08; N, 2.72; O, 1.52; S, 3.11.

[0373] Synthesis Example 123: Synthesis of Compound M484

[0374] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-phenyl-benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-phenyl-benzo[kl]xanthen-10-amine.

[0375] MALDI-TOF-MS results: Molecular ion peak: 700.23. Elemental analysis results: Theoretical values: C, 85.72; H, 4.17; B, 1.54; N, 4.00; O, 4.57. Experimental values: C, 85.72; H, 4.19; B, 1.54; N, 4.00; O, 4.55.

[0376] Synthesis Example 124: Synthesis of Compound M485

[0377] This example is basically the same as Synthesis Example 1, except that: In this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-phenyl-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-phenyl-benzo[kl]xanthen-10-amine. MALDI-TOF-MS results: Molecular ion peak: 716.21. Elemental analysis results: Theoretical values: C, 83.80; H, 4.08; B, 1.51; N, 3.91; O, 2.23; S, 4.47. Experimental values: C, 83.80; H, 4.13; B, 1.51; N, 3.91; O, 2.23; S, 4.42.

[0378] Synthesis Example 125: Synthesis of Compound M486

[0379] This example is basically the same as Synthesis Example 1, except that: In this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-phenyl-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-phenyl-7,7-dimethyl-7H-benzo[de]anthracen-10-amine. MALDI-TOF-MS results: Molecular ion peak: 742.26. Elemental analysis results: Theoretical values: C, 85.71; H, 4.75; B, 1.46; N, 3.77; S, 4.32. Experimental values: C, 85.73; H, 4.78; B, 1.46; N, 3.72; S, 4.32.

[0380] Synthesis Example 126: Synthesis of Compound M487

[0381] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-iodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-phenyl-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Di(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-phenylbenzo[kl]xanthen-10-amine. MALDI-TOF-MS result: molecular ion peak: 726.28. Elemental analysis result: theoretical values: C, 87.60; H, 4.85; B, 1.49; N, 3.86; O, 2.20. Experimental values: C, 87.60; H, 4.83; B, 1.49; N, 3.86; O, 2.22.

[0382] Synthesis Example 127: Synthesis of Compound M488

[0383] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodotert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-phenylbenzo[kl]xanthen-9-amine. Di(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-phenylbenzo[kl]xanthen-10-amine. MALDI-TOF-MS result: molecular ion peak: 756.29. Elemental analysis result: theoretical values: C, 85.71; H, 4.93; B, 1.43; N, 3.70; O, 4.23. Experimental values: C, 85.71; H, 4.98; B, 1.43; N, 3.65; O, 4.23.

[0384] Synthesis Example 128: Synthesis of Compound M489

[0385] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodotert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-phenylbenzo[kl]thioxanthen-9-amine. Di(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-phenylbenzo[kl]thioxanthen-10-amine. MALDI-TOF-MS result: molecular ion peak: 788.25. Elemental analysis result: theoretical values: C, 82.22; H, 4.73; B, 1.37; N, 3.55; S, 8.13. Experimental values: C, 82.22; H, 4.71; B, 1.37; N, 3.55; S, 8.15.

[0386] Synthesis Example 129: Synthesis of Compound M490

[0387] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-phenyl-benzo[kl]selenoxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-phenyl-benzo[kl]xanthen-10-amine. MALDI-TOF-MS result: molecular ion peak: 820.22. Elemental analysis result: theoretical values: C, 79.13; H, 4.55; B, 1.32; N, 3.42; O, 1.95; Se, 9.63. Experimental values: C, 79.13; H, 4.53; B, 1.32; N, 3.42; O, 1.95; Se, 9.65.

[0388] Synthesis Example 130: Synthesis of Compound M491

[0389] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-phenyl-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-phenyl-7,7-dimethyl-7H-benzo[de]-10-amine. MALDI-TOF-MS result: molecular ion peak: 808.40. Elemental analysis result: theoretical values: C, 89.09; H, 6.11; B, 1.34; N, 3.46. Experimental values: C, 89.09; H, 6.18; B, 1.30; N, 3.43.

[0390] Synthesis Example 131: Synthesis of Compound M492

[0391] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-diphenylaminoiodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(9,9-dimethyl-9H-xanthene)-benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-phenylbenzo[kl]xanthen-10-amine. MALDI-TOF-MS result: molecular ion peak: 999.36. Elemental analysis result: theoretical values: C, 85.28; H, 4.64; B, 1.08; N, 4.20; O, 4.80. Experimental values: C, 85.27; H, 4.60; B, 1.08; N, 4.20; O, 4.85.

[0392] Synthesis Example 132: Synthesis of Compound M493

[0393] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-diphenylaminoiodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(9,9-dimethyl-9H-xanthene)-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-phenylbenzo[kl]xanthen-10-amine. MALDI-TOF-MS result: molecular ion peak: 1015.34. Elemental analysis result: theoretical values: C, 83.93; H, 4.56; B, 1.06; N, 4.14; O, 3.15; S, 3.16. Experimental values: C, 83.95; H, 4.56; B, 1.04; N, 4.14; O, 3.15; S, 3.16.

[0394] Synthesis Example 133: Synthesis of Compound M500

[0395] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 9-(3-bromo-5-iodophenyl)-3,6-di-tert-butyl-9H-carbazole. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-10-amine. MALDI-TOF-MS result: molecular ion peak: 1089.54. Elemental analysis result: theoretical values: C, 85.93; H, 6.29; B, 0.99; N, 3.85; O, 2.93. Experimental values: C, 85.95; H, 6.28; B, 0.98; N, 3.87; O, 2.91.

[0396] Synthesis Example 134: Synthesis of Compound M501

[0397] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 9-(3-bromo-5-iodophenyl)-3,6-di-tert-butyl-9H-carbazole. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]thioxanthen-10-amine. MALDI-TOF-MS result: molecular ion peak: 1105.32. Elemental analysis result: theoretical values: C, 84.68; H, 6.20; B, 0.98; N, 3.80; O, 1.45; S, 2.90. Experimental values: C, 84.70; H, 6.20; B, 0.98; N, 3.80; O, 1.45; S, 2.88.

[0398] Synthesis Example 135: Synthesis of Compound M502

[0399] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 9-(3-bromo-5-iodophenyl)-3,6-di-tert-butyl-9H-carbazole. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]thioxanthen-9-amine. Di(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenyl-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. MALDI-TOF-MS result: molecular ion peak: 1105.52. Elemental analysis result: theoretical values: C, 85.92; H, 6.59; B, 0.95; N, 3.71; S, 2.83. Experimental values: C, 85.92; H, 6.55; B, 0.95; N, 3.75; S, 2.83.

[0400] Synthesis Example 136: Synthesis of Compound M503

[0401] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodotert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl)-benzo[kl]xanthen-9-amine. Di(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-10-amine. MALDI-TOF-MS result: molecular ion peak: 922.47. Elemental analysis result: theoretical values: C, 85.88; H, 6.44; B, 1.17; N, 3.04; O, 3.47. Experimental values: C, 85.88; H, 6.44; B, 1.19; N, 3.02; O, 3.47.

[0402] Synthesis Example 137: Synthesis of Compound M505

[0403] This example is basically the same as Synthetic Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalenyl)-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]thioxanthen-10-amine. MALDI-TOF-MS result: molecular ion peak: 964.50. Elemental analysis result: theoretical values: C, 85.87; H, 6.79; B, 1.12; N, 2.90; S, 3.32. Experimental values: C, 85.83; H, 6.79; B, 1.12; N, 2.94; S, 3.32.

[0404] Synthetic Example 138: Synthesis of Compound M506

[0405] This example is basically the same as Synthetic Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butylphenyl-2-(3,5-di-tert-butylphenyl)phenyl)-benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-10-amine. MALDI-TOF-MS result: molecular ion peak: 1056.58. Elemental analysis result: theoretical values: C, 86.34; H, 6.96; B, 1.02; N, 2.65; O, 3.03. Experimental values: C, 86.34; H, 6.98; B, 1.00; N, 2.65; O, 3.03.

[0406] Synthetic Example 139: Synthesis of Compound M507

[0407] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butylphenyl-2-(3,5-di-tert-butylphenyl)phenyl)-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-10-amine. MALDI-TOF-MS result: molecular ion peak: 1088.53. Elemental analysis result: theoretical values: C, 83.80; H, 6.75; B, 0.99; N, 2.57; S, 5.89. Experimental values: C, 83.80; H, 6.79; B, 0.99; N, 2.57; S, 5.85.

[0408] Synthesis Example 140: Synthesis of Compound M508

[0409] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butylphenyl-2-(3,5-di-tert-butylphenyl)phenyl)-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]thioxanthen-10-amine. MALDI-TOF-MS result: molecular ion peak: 1098.61. Elemental analysis result: theoretical values: C, 86.31; H, 7.24; B, 0.98; N, 2.55; S, 2.92. Experimental values: C, 86.32; H, 7.23; B, 0.98; N, 2.55; S, 2.92.

[0410] Synthesis Example 141: Synthesis of Compound M511

[0411] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-phenyl-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-phenylbenzo[kl]xanthen-9-amine. MALDI-TOF-MS result: molecular ion peak: 772.27. Elemental analysis result: theoretical values: C, 83.93; H, 4.83; B, 1.40; N, 3.63; O, 2.07; S, 4.15. Experimental values: C, 83.93; H, 4.82; B, 1.40; N, 3.63; O, 2.07; S, 4.16.

[0412] Synthesis Example 142: Synthesis of Compound M515

[0413] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-diphenylaminoiodobenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-phenyl-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-phenylbenzo[kl]xanthen-9-amine. MALDI-TOF-MS result: molecular ion peak: 883.28. Elemental analysis result: theoretical values: C, 84.25; H, 4.33; B, 1.22; N, 4.75; O, 1.81; S, 3.63. Experimental values: C, 84.25; H, 4.35; B, 1.22; N, 4.75; O, 1.81; S, 3.61.

[0414] Synthesis Example 143: Synthesis of Compound M517

[0415]

[0416] This example is basically the same as Synthesis Example 1, except that: in this example, the amount of N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is doubled, and the second-step reaction is not required. MALDI-TOF-MS result: molecular ion peak: 742.32. Elemental analysis result: theoretical values: C, 85.71; H, 4.75; B, 1.46; N, 3.77; O, 4.31. Experimental values: C, 85.69; H, 4.77; B, 1.46; N, 3.76; O, 4.32.

[0417] Synthesis Example 144: Synthesis of Compound M518

[0418] This example is basically the same as Synthesis Example 143, except that: in this example, N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tolylbenzo[kl]thioxanthen-9-amine. MALDI-TOF-MS result: molecular ion peak: 774.23. Elemental analysis result: theoretical values: C, 82.16; H, 4.55; B, 1.40; N, 3.62; S, 8.28. Experimental values: C, 82.16; H, 4.58; B, 1.40; N, 3.62; S, 8.25.

[0419] Synthesis Example 145: Synthesis of Compound M519

[0420] This example is basically the same as Synthesis Example 1, except that: in this example, N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tolylbenzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-p-tolylbenzo[kl]xanthen-9-amine. MALDI-TOF-MS result: molecular ion peak: 758.26. Elemental analysis result: theoretical values: C, 83.90; H, 4.65; B, 1.42; N, 3.69; O, 2.11; S, 4.23. Experimental values: C, 83.95; H, 4.60; B, 1.42; N, 3.69; O, 2.11; S, 4.23.

[0421] Synthesis Example 146: Synthesis of Compound M520

[0422] This example is basically the same as Synthesis Example 143, except that: in this example, N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tolyl-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. MALDI-TOF-MS result: molecular ion peak: 794.38. Elemental analysis result: theoretical values: C, 89.16; H, 5.96; B, 1.36; N, 3.52. Experimental values: C, 89.18; H, 5.94; B, 1.36; N, 3.52.

[0423] Synthesis Example 147: Synthesis of Compound M521

[0424] This example is basically the same as Synthesis Example 143, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 9-(3-bromo-5-iodophenyl)-3,6-di-tert-butyl-9H-carbazole. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-9-amine. MALDI-TOF-MS result: molecular ion peak: 1089.54. Elemental analysis result: theoretical values: C, 85.93; H, 6.29; B, 0.99; N, 3.85; O, 2.93. Experimental values: C, 85.93; H, 6.29; B, 0.99; N, 3.85; O, 2.93.

[0425] Synthesis Example 148: Synthesis of Compound M522

[0426] This example is basically the same as Synthesis Example 143, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 9-(3-bromo-5-iodophenyl)-3,6-di-tert-butyl-9H-carbazole. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]thioxanthen-9-amine. MALDI-TOF-MS result: molecular ion peak: 1121.49. Elemental analysis result: theoretical values: C, 83.47; H, 6.11; B, 0.96; N, 3.74; S, 5.71. Experimental values: C, 83.42; H, 6.16; B, 0.96; N, 3.74; S, 5.71.

[0427] Synthesis Example 149: Synthesis of Compound M523

[0428] This example is basically the same as Synthesis Example 143, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 9-(3-bromo-5-iodophenyl)-3,6-di-tert-butyl-9H-carbazole. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenyl-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. MALDI-TOF-MS result: molecular ion peak: 1141.64. Elemental analysis result: theoretical values: C, 88.32; H, 7.06; B, 0.95; N, 3.68. Experimental values: C, 88.36; H, 7.02; B, 0.95; N, 3.68.

[0429] Synthesis Example 150: Synthesis of Compound M524

[0430] This example is basically the same as Synthesis Example 143, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. MALDI-TOF-MS result: molecular ion peak: 868.42. Elemental analysis result: theoretical values: C, 85.70; H, 6.15; B, 1.24; N, 3.22; O, 3.68. Experimental values: C, 85.75; H, 6.15; B, 1.20; N, 3.22; O, 3.67.

[0431] Synthesis Example 151: Synthesis of Compound M525

[0432] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-(3-dibenzofuran-yl)benzo[kl]thioxanthen-9-amine. MALDI-TOF-MS result: molecular ion peak: 934.32. Elemental analysis result: theoretical values: C, 82.21; H, 5.07; B, 1.16; N, 3.00; O, 1.71; S, 6.86. Experimental values: C, 82.21; H, 5.08; B, 1.16; N, 3.00; O, 1.70; S, 6.86.

[0433] Synthesis Example 152: Synthesis of Compound M527

[0434] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3-bromo-5-iodo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalenyl)-benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(3-dibenzofuran-yl)-benzo[kl]xanthen-9-amine. MALDI-TOF-MS result: molecular ion peak: 956.41. Elemental analysis result: theoretical values: C, 85.35; H, 5.58; B, 1.13; N, 2.93; O, 5.02. Experimental values: C, 85.36; H, 5.58; B, 1.12; N, 2.93; O, 5.02.

[0435] Synthesis Example 153: Synthesis of Compound M529

[0436] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 3,5-dibromo-tert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenyl-7,7-dimethyl-7H-benzo[de]anthracen-9-amine. MALDI-TOF-MS result: molecular ion peak: 974.57. Elemental analysis result: theoretical values: C, 88.68; H, 7.34; B, 1.11; N, 2.87. Experimental values: C, 88.69; H, 7.33; B, 1.13; N, 2.85.

[0437] Synthesis Example 154: Synthesis of Compound M530

[0438] This example is basically the same as Synthesis Example 143, except that: in this example, 3,5-dibromotoluene in the first-step reaction is replaced with an equimolar amount of 3,5-dibromotert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-10-amine. MALDI-TOF-MS result: molecular ion peak: 868.42. Elemental analysis result: theoretical values: C, 85.70; H, 6.15; B, 1.24; N, 3.22; O, 3.68. Experimental values: C, 85.74; H, 6.11; B, 1.25; N, 3.23; O, 3.66.

[0439] Synthesis Example 155: Synthesis of Compound M531

[0440] This example is basically the same as Synthesis Example 143, except that: in this example, 3,5-dibromotoluene in the first-step reaction is replaced with an equimolar amount of 3,5-dibromotert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]thioxanthen-10-amine. MALDI-TOF-MS result: molecular ion peak: 900.37. Elemental analysis result: theoretical values: C, 82.65; H, 5.93; B, 1.20; N, 3.11; S, 7.12. Experimental values: C, 82.68; H, 5.91; B, 1.19; N, 3.12; S, 7.11.

[0441] Synthesis Example 156: Synthesis of Compound M532

[0442] This example is basically the same as Synthesis Example 143, except that: in this example, 3,5-dibromotoluene in the first-step reaction is replaced with an equimolar amount of 3,5-dibromotert-butylbenzene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-p-tert-butylphenyl-7,7-dimethyl-7H-benzo[de]anthracen-10-amine. MALDI-TOF-MS result: molecular ion peak: 920.52. Elemental analysis result: theoretical values: C, 88.67; H, 7.11; B, 1.17; N, 3.04. Experimental values: C, 88.69; H, 7.11; B, 1.15; N, 3.04.

[0443] Synthesis Example 157: Synthesis of Compound M541

[0444] This example is basically the same as Synthesis Example 143, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 784.89. Elemental analysis result: theoretical values: C, 85.70; H, 7.32; B, 1.38; N, 3.57; O, 2.04. Experimental values: C, 85.74; H, 7.31; B, 1.36; N, 3.56; O, 2.04.

[0445] Synthesis Example 158: Synthesis of Compound M542

[0446] This example is basically the same as Synthesis Example 143, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]thioxanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 800.43. Elemental analysis result: theoretical values: C, 83.98; H, 7.17; B, 1.35; N, 3.50; S, 4.00. Experimental values: C, 83.94; H, 7.19; B, 1.35; N, 3.52; S, 4.00.

[0447] Synthesis Example 159: Synthesis of Compound M543

[0448] This example is basically the same as Synthesis Example 143, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]selenoxanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 848.38. Elemental analysis result: theoretical values: C, 79.33; H, 6.78; B, 1.27; N, 3.30; Se, 9.31. Experimental values: C, 79.33; H, 6.73; B, 1.27; N, 3.30; Se, 9.36.

[0449] Synthesis Example 160: Synthesis of Compound M544

[0450] This example is basically the same as Synthesis Example 143, except that: in this example, 3,5-dibromotoluene in the first-step reaction is replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl)-p-tert-butylaniline. MALDI-TOF-MS result: molecular ion peak: 892.55. Elemental analysis result: theoretical values: C, 86.07; H, 7.79; B, 1.21; N, 3.14; O, 1.79. Experimental values: C, 86.07; H, 7.79; B, 1.23; N, 3.12; O, 1.79.

[0451] Synthesis Example 161: Synthesis of Compound M545

[0452] This example is basically the same as Synthesis Example 143, except that: in this example, 3,5-dibromotoluene in the first-step reaction is replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]thioxanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl)-p-tert-butylaniline. MALDI-TOF-MS result: molecular ion peak: 908.53. Elemental analysis result: theoretical values: C, 84.55; H, 7.65; B, 1.19; N, 3.08; S, 3.53. Experimental values: C, 84.58; H, 7.62; B, 1.19; N, 3.08; S, 3.53.

[0453] Synthesis Example 162: Synthesis of Compound M546

[0454] This example is basically the same as Synthesis Example 143, except that: in this example, 3,5-dibromotoluene in the first-step reaction is replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]selenoxanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthyl)-p-tert-butylaniline. MALDI-TOF-MS result: molecular ion peak: 956.47. Elemental analysis result: theoretical values: C, 80.40; H, 7.27; B, 1.13; N, 2.93; Se, 8.26. Experimental values: C, 80.46; H, 7.21; B, 1.13; N, 2.93; Se, 8.26.

[0455] Synthesis Example 163: Synthesis of Compound M547

[0456] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalenyl)-p-tert-butylaniline. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-(4-(2-phenylpropyl)phenyl)-p-tert-butylaniline. MALDI-TOF-MS result: molecular ion peak: 900.52. Elemental analysis result: theoretical values: C, 86.64; H, 7.27; B, 1.20; N, 3.11; O, 1.78. Experimental values: C, 86.64; H, 7.26; B, 1.20; N, 3.12; O, 1.78.

[0457] Synthesis Example 164: Synthesis of Compound M548

[0458] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]thioxanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalenyl)-p-tert-butylaniline. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-(4-(2-phenylpropyl)phenyl)-p-tert-butylaniline. MALDI-TOF-MS result: molecular ion peak: 916.50. Elemental analysis result: theoretical values: C, 85.13; H, 7.14; B, 1.18; N, 3.05; S, 3.50. Experimental values: C, 85.13; H, 7.19; B, 1.18; N, 3.00; S, 3.50.

[0459] Synthesis Example 165: Synthesis of Compound M549

[0460] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-(3,5-di-tert-butylphenyl)phenyl)-p-tert-butylaniline. MALDI-TOF-MS result: molecular ion peak: 972.61. Elemental analysis result: theoretical values: C, 86.39; H, 7.98; B, 1.11; N, 2.88; O, 1.64. Experimental values: C, 86.39; H, 7.96; B, 1.11; N, 2.88; O, 1.66.

[0461] Synthesis Example 166: Synthesis of Compound M550

[0462] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]thioxanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-(3,5-di-tert-butylphenyl)phenyl)-p-tert-butylaniline. MALDI-TOF-MS result: molecular ion peak: 988.59. Elemental analysis result: theoretical values: C, 84.99; H, 7.85; B, 1.09; N, 2.83; S, 3.24. Experimental values: C, 84.99; H, 7.83; B, 1.09; N, 2.83; S, 3.26.

[0463] Synthesis Example 167: Synthesis of Compound M552

[0464] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-benzofuran-3-amine. MALDI-TOF-MS result: molecular ion peak: 824.45. Elemental analysis result: theoretical values: C, 84.45; H, 6.97; B, 1.31; N, 3.40; O, 3.88. Experimental values: C, 84.45; H, 6.98; B, 1.31; N, 3.39; O, 3.88.

[0465] Synthesis Example 168: Synthesis of Compound M553

[0466] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]thioxanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-benzofuran-3-amine. MALDI-TOF-MS result: molecular ion peak: 840.43. Elemental analysis result: theoretical values: C, 82.84; H, 6.83; B, 1.29; N, 3.33; O, 1.90; S, 3.81. Experimental values: C, 82.84; H, 6.83; B, 1.24; N, 3.30; O, 1.98; S, 3.81.

[0467] Synthesis Example 169: Synthesis of Compound M554

[0468] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]selenoxanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-benzofuran-3-amine. MALDI-TOF-MS result: molecular ion peak: 888.37. Elemental analysis result: theoretical values: C, 78.46; H, 6.47; B, 1.22; N, 3.16; O, 1.80; Se, 8.89. Experimental values: C, 78.46; H, 6.49; B, 1.24; N, 3.16; O, 1.80; Se, 8.85

[0469] Synthesis Example 170: Synthesis of Compound M555

[0470] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalenyl)-p-tert-butylaniline. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalenyl)-benzofuran-3-amine. MALDI-TOF-MS result: molecular ion peak: 933.10. Elemental analysis result: theoretical values: C, 84.96; H, 7.45; B, 1.16; N, 3.00; O, 3.43. Experimental values: C, 84.96; H, 7.43; B, 1.16; N, 3.00; O, 3.45

[0471] Synthesis Example 171: Synthesis of Compound M557

[0472] This example is basically the same as Synthesis Example 1, except that: in this example, 3-bromo-5-iodotoluene in the first-step reaction is replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-(3,5-di-tert-butylphenyl)phenyl)-p-tert-butylaniline. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-(4-tert-butylphenyl)-benzofuran-3-amine. MALDI-TOF-MS result: molecular ion peak: 1013.23. Elemental analysis result: theoretical values: C, 85.35; H, 7.66; B, 1.07; N, 2.76; O, 3.16. Experimental values: C, 85.39; H, 7.62; B, 1.07; N, 2.76; O, 3.16

[0473] Synthesis Example 172: Synthesis of Compound M561

[0474] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-benzofuran-2-amine. MALDI-TOF-MS result: molecular ion peak: 824.45. Elemental analysis result: theoretical values: C, 84.45; H, 6.97; B, 1.31; N, 3.40; O, 3.88. Experimental values: C, 84.45; H, 6.97; B, 1.36; N, 3.35; O, 3.88.

[0475] Synthesis Example 173: Synthesis of Compound M562

[0476] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]thioxanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-benzofuran-2-amine. MALDI-TOF-MS result: molecular ion peak: 840.43. Elemental analysis result: theoretical values: C, 82.84; H, 6.83; B, 1.29; N, 3.33; O, 1.90; S, 3.81. Experimental values: C, 82.84; H, 6.86; B, 1.26; N, 3.33; O, 1.90; S, 3.81.

[0477] Synthesis Example 174: Synthesis of Compound M566

[0478] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-benzothiophene-3-amine. Di(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-benzofuran-3-amine. MALDI-TOF-MS result: molecular ion peak: 880.42. Elemental analysis result: theoretical values: C, 81.80; H, 6.52; B, 1.23; N, 3.18; O, 3.63; S, 3.64. Experimental values: C, 81.80; H, 6.52; B, 1.21; N, 3.18; O, 3.65; S, 3.64.

[0479] Synthesis Example 175: Synthesis of Compound M567

[0480] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]thioxanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-benzothiophene-3-amine. Di(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-benzofuran-3-amine. MALDI-TOF-MS result: molecular ion peak: 896.40. Elemental analysis result: theoretical values: C, 80.34; H, 6.40; B, 1.21; N, 3.12; O, 1.78; S, 7.15. Experimental values: C, 80.34; H, 6.45; B, 1.21; N, 3.10; O, 1.75; S, 7.15.

[0481] Synthesis Example 176: Synthesis of Compound M568

[0482] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzothieno[3,2-b]benzothiophene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)benzothiophen-3-amine. Di(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)benzofuran-3-amine. MALDI-TOF-MS result: molecular ion peak: 944.34. Elemental analysis result: theoretical values: C, 76.34; H, 6.09; B, 1.15; N, 2.97; O, 1.69; S, 3.40; Se, 8.37. Experimental values: C, 76.34; H, 6.10; B, 1.15; N, 2.97; O, 1.69; S, 3.39; Se, 8.37.

[0483] Synthesis Example 177: Synthesis of Compound M569

[0484] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzothieno[3,2-b]benzothiophene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-(3,5-di-tert-butylphenyl)phenyl)benzothiophen-3-amine. Di(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)benzofuran-3-amine. MALDI-TOF-MS result: molecular ion peak: 1068.58. Elemental analysis result: theoretical values: C, 83.12; H, 7.26; B, 1.01; N, 2.62; O, 2.99; S, 3.06. Experimental values: C, 83.12; H, 7.20; B, 1.01; N, 2.62; O, 2.99; S, 3.00.

[0485] Synthesis Example 178: Synthesis of Compound M570

[0486] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-(3,5-di-tert-butylphenyl)phenyl)-benzothiophen-3-amine. Di(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-benzofuran-3-amine. MALDI-TOF-MS result: molecular ion peak: 1084.56. Elemental analysis result: theoretical values: C, 81.89; H, 7.15; B, 1.00; N, 2.58; O, 1.47; S, 5.91. Experimental values: C, 81.90; H, 7.14; B, 1.00; N, 2.58; O, 1.47; S, 5.91.

[0487] Synthesis Example 179: Synthesis of Compound M571

[0488] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-benzofuran-2-amine. Di(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-benzofuran-3-amine. MALDI-TOF-MS result: molecular ion peak: 864.45. Elemental analysis result: theoretical values: C, 83.32; H, 6.64; B, 1.25; N, 3.24; O, 5.55. Experimental values: C, 83.32; H, 6.67; B, 1.22; N, 3.24; O, 5.55.

[0489] Synthesis Example 180: Synthesis of Compound M572

[0490] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction is replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butylphenyl)-benzofuran-2-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-(4-tert-butylphenyl)-benzofuran-3-amine. MALDI-TOF-MS result: molecular ion peak: 880.42. Elemental analysis result: theoretical values: C, 81.80; H, 6.52; B, 1.23; N, 3.18; O, 3.63; S, 3.64. Experimental values: C, 81.85; H, 6.52; B, 1.23; N, 3.13; O, 3.63; S, 3.64.

[0491] Synthesis Example 181: Synthesis of Compound M574

[0492] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction is replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)-benzofuran-2-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-(4-tert-butylphenyl)-benzofuran-3-amine. MALDI-TOF-MS result: molecular ion peak: 1052.60. Elemental analysis result: theoretical values: C, 84.39; H, 7.37; B, 1.03; N, 2.66; O, 4.56. Experimental values: C, 84.36; H, 7.38; B, 1.01; N, 2.66; O, 4.56.

[0493] Synthesis Example 182: Synthesis of Compound M575

[0494] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)benzofuran-2-amine. Di(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)benzofuran-3-amine. MALDI-TOF-MS result: molecular ion peak: 1068.58. Elemental analysis result: theoretical values: C, 83.12; H, 7.26; B, 1.01; N, 2.62; O, 2.99; S, 3.00. Experimental values: C, 83.12; H, 7.29; B, 1.01; N, 2.62; O, 2.96; S, 3.00.

[0495] Synthesis Example 183: Synthesis of Compound M576

[0496] This example is basically the same as Synthesis Example 143, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)benzofuran-2-amine. MALDI-TOF-MS result: molecular ion peak: 752.32. Elemental analysis result: theoretical values: C, 82.98; H, 5.49; B, 1.44; N, 3.72; O, 6.38. Experimental values: C, 83.01; H, 5.47; B, 1.45; N, 3.72; O, 6.36.

[0497] Synthesis Example 184: Synthesis of Compound M577

[0498] This example is basically the same as Synthesis Example 143, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)benzofuran-2-amine. MALDI-TOF-MS result: molecular ion peak: 768.30. Elemental analysis result: theoretical values: C, 81.24; H, 5.38; B, 1.41; N, 3.64; O, 4.16; S, 4.17. Experimental values: C, 81.28; H, 5.38; B, 1.41; N, 3.60; O, 4.16; S, 4.17.

[0499] Synthesis Example 185: Synthesis of Compound M579

[0500] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)benzofuran-2-amine. Di(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)benzofuran-2-amine. MALDI-TOF-MS result: molecular ion peak: 941.03. Elemental analysis result: theoretical value: C, 84.24; H, 6.53; B, 1.15; N, 2.98; O, 5.10. Experimental value: C, 84.26; H, 6.51; B, 1.15; N, 2.98; O, 5.10.

[0501] Synthesis Example 186: Synthesis of Compound M580

[0502] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]thioxanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)benzofuran-2-amine. Di(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)benzofuran-2-amine. MALDI-TOF-MS result: molecular ion peak: 956.45. Elemental analysis result: theoretical value: C, 82.83; H, 6.42; B, 1.13; N, 2.93; O, 3.34; S, 3.35. Experimental value: C, 82.86; H, 6.42; B, 1.10; N, 2.93; O, 3.34; S, 3.35

[0503] Synthesis Example 187: Synthesis of Compound M581

[0504] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 884.40. Elemental analysis result: theoretical values: C, 84.15; H, 6.04; B, 1.22; N, 3.17; O, 1.81; S, 3.62. Experimental values: C, 84.18; H, 6.04; B, 1.22; N, 3.14; O, 1.81; S, 3.62.

[0505] Synthesis Example 188: Synthesis of Compound M582

[0506] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]selenoxanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of bis(4-tert-butylphenyl)amine. MALDI-TOF-MS result: molecular ion peak: 932.34. Elemental analysis result: theoretical values: C, 79.91; H, 5.73; B, 1.16; N, 3.01; O, 1.72; Se, 8.47. Experimental values: C, 79.91; H, 5.73; B, 1.14; N, 3.01; O, 1.72; Se, 8.49.

[0507] Synthesis Example 189: Synthesis of Compound M583

[0508] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction is replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-1-yl)phenyl)benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-1-yl)-tert-butylaniline. MALDI-TOF-MS result: molecular ion peak: 1052.55. Elemental analysis result: theoretical values: C, 86.67; H, 6.60; B, 1.03; N, 2.66; O, 3.04. Experimental values: C, 86.67; H, 6.55; B, 1.03; N, 2.66; O, 3.09.

[0509] Synthesis Example 190: Synthesis of Compound M584

[0510] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction is replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]thioxanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-1-yl)phenyl)benzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-1-yl)-tert-butylaniline. MALDI-TOF-MS result: molecular ion peak: 1068.52. Elemental analysis result: theoretical values: C, 85.37; H, 6.50; B, 1.01; N, 2.62; O, 1.50; S, 3.00. Experimental values: C, 85.37; H, 6.44; B, 1.01; N, 2.62; O, 1.50; S, 3.06.

[0511] Synthesis Example 191: Synthesis of Compound M588

[0512] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction is replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butylphenyl)benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-(4-(3,5-di-tert-butylphenyl)phenyl)-p-tert-butylaniline. MALDI-TOF-MS result: molecular ion peak: 1072.55. Elemental analysis result: theoretical values: C, 85.05; H, 6.86; B, 1.01; N, 2.61; O, 1.49; S, 2.99. Experimental values: C, 85.09; H, 6.82; B, 1.01; N, 2.61; O, 1.49; S, 2.99.

[0513] Synthesis Example 192: Synthesis of Compound M589

[0514] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction is replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]thioxanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butylphenyl)benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-(4-(3,5-di-tert-butylphenyl)phenyl)-p-tert-butylaniline. MALDI-TOF-MS result: molecular ion peak: 1088.53. Elemental analysis result: theoretical values: C, 83.80; H, 6.75; B, 0.99; N, 2.57; S, 5.89. Experimental values: C, 83.86; H, 6.69; B, 0.99; N, 2.57; S, 5.89.

[0515] Synthesis Example 193: Synthesis of Compound M591

[0516] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-5-tert-butyl-benzofuran-2-amine. MALDI-TOF-MS result: molecular ion peak: 908.41. Elemental analysis result: theoretical values: C, 84.57; H, 5.88; B, 1.19; N, 3.08; O, 5.28. Experimental values: C, 84.58; H, 5.87; B, 1.19; N, 3.07; O, 5.29.

[0517] Synthesis Example 194: Synthesis of Compound M592

[0518] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]thioxanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with an equimolar amount of N-p-tert-butylphenylbenzo[kl]xanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with an equimolar amount of N-(4-tert-butylphenyl)-5-tert-butyl-benzofuran-2-amine. MALDI-TOF-MS result: molecular ion peak: 924.39. Elemental analysis result: theoretical values: C, 83.10; H, 5.78; B, 1.17; N, 3.03; O, 3.46; S, 3.47. Experimental values: C, 83.15; H, 5.78; B, 1.12; N, 3.03; O, 3.46; S, 3.47.

[0519] Synthesis Example 195: Synthesis of Compound M594

[0520] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction is replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalenyl)-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalenyl)-5-tert-butyl-benzofuran-2-amine. MALDI-TOF-MS result: molecular ion peak: 1032.49. Elemental analysis result: theoretical values: C, 83.70; H, 6.34; B, 1.05; N, 2.71; O, 3.10; S, 3.10. Experimental values: C, 83.76; H, 6.30; B, 1.05; N, 2.71; O, 3.08; S, 3.10.

[0521] Synthesis Example 196: Synthesis of Compound M595

[0522] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction is replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]thioxanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalenyl)-benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalenyl)-5-tert-butyl-benzofuran-2-amine. MALDI-TOF-MS result: molecular ion peak: 1048.66. Elemental analysis result: theoretical values: C, 82.42; H, 6.24; B, 1.03; N, 2.67; O, 1.52; S, 6.11. Experimental values: C, 82.42; H, 6.29; B, 1.03; N, 2.62; O, 1.52; S, 6.11.

[0523] Synthesis Example 197: Synthesis of Compound M600

[0524] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction is replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]xanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butylphenyl)benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-(4-tert-butylphenyl)benzofuran-2-amine. MALDI-TOF-MS result: molecular ion peak: 868.33. Elemental analysis result: theoretical values: C, 85.37; H, 6.29; B, 1.04; N, 2.69; O, 4.61. Experimental values: C, 85.37; H, 6.34; B, 1.02; N, 2.66; O, 4.61.

[0525] Synthesis Example 198: Synthesis of Compound M601

[0526] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction is replaced with an equimolar amount of 8-bromo-10-iodobenzo[kl]thioxanthene. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction is replaced with an equimolar amount of N-(4-tert-butylphenyl)benzo[kl]thioxanthen-9-amine. Bis(4-methylphenyl)amine in the second-step reaction is replaced with an equimolar amount of N-(4-tert-butylphenyl)benzofuran-2-amine. MALDI-TOF-MS result: molecular ion peak: 884.31. Elemental analysis result: theoretical values: C, 81.43; H, 5.13; B, 1.22; N, 3.17; O, 1.81; S, 7.25. Experimental values: C, 81.43; H, 5.09; B, 1.22; N, 3.17; O, 1.81; S, 7.29.

[0527] Synthesis Example 199: Synthesis of Compound M603

[0528] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with 8-bromo-10-iodobenzo[kl]xanthene in an equimolar amount. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)benzo[kl]xanthen-9-amine in an equimolar amount. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with N-(4-tert-butylphenyl)benzofuran-2-amine in an equimolar amount. MALDI-TOF-MS result: molecular ion peak: 1040.51. Elemental analysis result: theoretical values: C, 82.94; H, 5.22; B, 1.24; N, 3.22; O, 3.68; S, 3.69. Experimental values: C, 82.97; H, 5.20; B, 1.23; N, 3.22; O, 3.68; S, 3.69.

[0529] Synthesis Example 200: Synthesis of Compound M604

[0530] This example is basically the same as Synthesis Example 1, except that: in this example, 3,5-dibromotoluene in the first-step reaction needs to be replaced with 8-bromo-10-iodobenzo[kl]thioxanthene in an equimolar amount. N-p-tolylbenzo[kl]xanthen-9-amine in the first-step reaction needs to be replaced with N-(4-tert-butyl-2-(3,5-di-tert-butylphenyl)phenyl)benzo[kl]thioxanthen-9-amine in an equimolar amount. Bis(4-methylphenyl)amine in the second-step reaction needs to be replaced with N-(4-tert-butylphenyl)benzofuran-2-amine in an equimolar amount. MALDI-TOF-MS result: molecular ion peak: 1072.66. Elemental analysis result: theoretical values: C, 82.81; H, 6.10; B, 1.01; N, 2.61; O, 1.49; S, 5.97. Experimental values: C, 82.81; H, 6.12; B, 1.01; N, 2.61; O, 1.49; S, 5.95.

[0531] Application embodiments of the compounds prepared by the present invention:

[0532] The compounds of the present invention can be applied in organic electroluminescent devices, i.e., OLED devices, and are most preferably used as materials in the light-emitting layer.

[0533] An OLED includes a first electrode and a second electrode, and an organic material layer located between the electrodes. The organic material layer can be further divided into multiple regions. For example, the organic material layer can include a hole transport region, a light-emitting layer, and an electron transport region.

[0534] Device Example 1:

[0535] An organic electroluminescent device includes an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode (Al) that are sequentially arranged. The preparation method of the organic electroluminescent device is as follows:

[0536] (1) The glass substrate coated with the ITO transparent conductive layer is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone / ethanol mixed solvent, baked in a clean environment until all moisture is completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam on the surface;

[0537] (2) Place the glass substrate with the anode in a vacuum chamber, evacuate to less than 1×10 -5 Pa, and vacuum deposit HAT-CN on the anode layer film as the hole injection layer at a deposition rate of 0.1 nm / s and a deposited film thickness of 5 nm;

[0538] (3) Vacuum deposit the compound NPB on the hole injection layer as the hole transport layer at a deposition rate of 0.1 nm / s and a total deposited film thickness of 30 nm;

[0539] (4) Vacuum deposit the compound BCzPh on the hole transport layer as the electron blocking layer at a deposition rate of 0.1 nm / s and a total deposited film thickness of 10 nm;

[0540] (5) Vacuum deposit the light-emitting layer on the electron blocking layer. The light-emitting layer includes a binary mixture (98 / 2, w / w) of the host material α,β-ADN and the polycyclic aromatic organic compound M73, at a deposition rate of 0.1 nm / s and a total deposited film thickness of 25 nm;

[0541] (6) Vacuum deposit the compound CzPhPy on the light-emitting layer as the hole blocking layer at a deposition rate of 0.1 nm / s and a total deposited film thickness of 5 nm;

[0542] (7) Vacuum deposit the compound DPPyA on the hole blocking layer as the electron transport layer at a deposition rate of 0.1 nm / s and a total deposited film thickness of 30 nm;

[0543] (8) Vacuum deposit LiF on the electron transport layer as the electron injection layer at a deposition rate of 0.1 nm / s and a thickness of 1 nm;

[0544] (9) Vacuum deposit an Al layer with a thickness of 150 nm on the electron injection layer as the cathode of the device at a deposition rate of 1 nm / s to obtain the organic electroluminescent device.

[0545]

[0546] Device Example 2 - 200, Device Comparative Example 1 - 4:

[0547] An organic electroluminescent device, which is different from Device Example 1 only in that the dyes in the light - emitting layer are the compounds shown in Table 1 respectively; other layers, thicknesses, materials, and preparation methods are the same as those in Device Example 1.

[0548] The dye structures in Device Comparative Example 1 - 4 are as follows:

[0549]

[0550] Performance test of the device:

[0551] (1) LT 97 The test of the lifetime is as follows: Use a luminance meter to measure the initial luminance value of the device at a current density of 40 mA / cm 2 . Keep the current constant, and measure the time when the luminance of the device drops to 97% of the initial luminance, with the unit of h; Take the LT 97 lifetime test value of Device Comparative Example 1 as 1.00, and calculate the LT 97 lifetime test values of other devices and the ratio of the LT 97 lifetime test value of Device Comparative Example 1.

[0552] (2) The test method of the external quantum efficiency is as follows: Measure the external quantum efficiency (EQE, %) of the device by using the integrating - sphere method. The test results are shown in Table 1:

[0553] Table 1:

[0554]

[0555]

[0556]

[0557]

[0558]

[0559]

[0560] The polycyclic aromatic organic compound provided by the present invention, as a luminescent layer dye for an organic electroluminescent device, can significantly improve the efficiency of the device and significantly extend its lifespan. Specifically, compared with the comparative compounds C1, C2, C3, and C4, the device containing the compound of the present invention has higher efficiency and longer lifespan. This may be because the unique structure of formula (2) in the compound of the present invention endows the compound with a lower triplet excited state energy level, which is conducive to reducing quenching and chemical degradation caused by the triplet excited state, thereby improving the efficiency and lifespan of the device. At the same time, due to the large oscillator strength and rigid structure of the compound of the present invention, it is conducive to suppressing the vibration of molecules to improve the luminescence efficiency of the compound and the efficiency of the device.

[0561] In summary, through the special design of the molecular structure, the present invention enables the polycyclic aromatic organic compound to be used as a dye for the luminescent layer, which can significantly extend the lifespan of the device and optimize the luminescence performance of the device.

[0562] The preferred embodiments of the present invention have been described in detail above. However, the present invention is not limited to the specific details in the above embodiments. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solutions of the present invention, and these simple modifications all fall within the protection scope of the present invention.

[0563] In addition, it should be noted that, in the above specific embodiments, the various specific technical features described can be combined in any suitable manner without contradiction. To avoid unnecessary repetition, the present invention will not separately describe various possible combination methods.

[0564] Furthermore, any combination can be made between different embodiments of the present invention as long as it does not violate the idea of the present invention, and it should also be regarded as the content disclosed by the present invention.

Claims

1. A polycyclic aromatic compound, characterized in that, It has the structure shown in formula (1): In formula (1), X1 and X2 are each independently O, S, Se, NR1, CR2R3 or SiR4R5; R2 and R3 are not connected or are connected to form a ring, and R4 and R5 are not connected or are connected to form a ring; Ring A, ring B and ring C are each independently selected from an unsubstituted or R'-substituted C6-C60 aromatic ring, an unsubstituted or R'-substituted C3-C60 heteroaromatic ring, and R' groups adjacent to each other are not connected or are connected to form a ring; And at least one of ring A, ring B and ring C is fused to a group having the structure shown in formula (2); In formula (2), the dotted line represents that formula (2) is condensed at any fusible position in ring A, ring B or ring C; Q is selected from O, S, Se, NR6, CR7R8 or SiR9R 10 ; R7 and R8 are not connected or are connected to form a ring, and R9 and R 10 are not connected or are connected to form a ring; Z1, Z2, Z3, Z4, Z5 and Z6 are each independently CR 11 or N, and adjacent Rs 11 are not connected or are connected to form a ring; R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 each independently selected from an unsubstituted or R'-substituted C1-C30 linear alkyl group, an unsubstituted or R'-substituted C3-C20 cycloalkyl group, an unsubstituted or R'-substituted C7-C30 aralkyl group, an unsubstituted or R'-substituted C1-C30 alkoxy group, an unsubstituted or R'-substituted C2-C30 aliphatic hydrocarbon amine group, an unsubstituted or R'-substituted C4-C30 cyclic aliphatic hydrocarbon amine group, an unsubstituted or R'-substituted C6-C30 arylamine group, an unsubstituted or R'-substituted C3-C30 heteroarylamine group, an unsubstituted or R'-substituted C6-C30 aryloxy group, an unsubstituted or R'-substituted C6-C60 arylboron group, an unsubstituted or R'-substituted C6-C60 aryl group, and an unsubstituted or R'-substituted C3-C60 heteroaryl group; R 11 selected from one of hydrogen, deuterium, halogen, cyano, unsubstituted or R'-substituted C1-C30 linear alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C7-C30 aralkyl, unsubstituted or R'-substituted C1-C30 alkoxy, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C6-C60 arylboron, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; R' is selected from one of deuterium, halogen, cyano, C1-C20 linear alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, C6-C30 arylboron, C3-C30 heteroaryl or a combination of two of them.

2. The polycyclic aromatic compound according to claim 1, wherein In formula (2), Q is selected from O, S, NR6 or CR7R8; R6 is selected from an unsubstituted or R'-substituted C6-C60 aryl; R7 and R8 are each independently selected from an unsubstituted or R'-substituted C1-C10 linear alkyl, an unsubstituted or R'-substituted C3-C10 cycloalkyl, an unsubstituted or R'-substituted C1-C10 alkoxy, an unsubstituted or R'-substituted C6-C30 arylamino, an unsubstituted or R'-substituted C3-C30 heteroarylamino, an unsubstituted or R'-substituted C6-C30 aryloxy, an unsubstituted or R'-substituted C6-C60 aryl, an unsubstituted or R'-substituted C3-C60 heteroaryl; R' is selected from one of deuterium, halogen, cyano, C1-C10 linear alkyl, C3-C10 cycloalkyl, C6-C30 aryloxy, C6-C30 aryl, C3-C30 heteroaryl; In formula (2), at most 3 of Z1-Z6 are N; preferably, at most 1 of Z1-Z6 is N.

3. The polycyclic aromatic compound according to claim 1 or 2, characterized in that, In formula (1), ring A and ring B are each independently selected from the structures shown in formula (3) or formula (4), ring C is selected from the structure shown in formula (3), and at least one of ring A, ring B and ring C is fused to a group having the structure shown in formula (2); In formula (3) and formula (4), the dotted line represents the condensed bicyclic structure containing B and X1 in formula (1), or the condensed bicyclic structure containing B and X2 in formula (1); The dotted line in formula (2) represents that formula (2) is condensed at any fusible position other than the dotted line in the structure of formula (3) or formula (4); In formula (3), Y1, Y2, Y3 and Y4 are each independently selected from CR 12 or N, and adjacent Rs 12 are not connected or are connected to form a ring; R 12 Each independently selected from hydrogen, deuterium, halogen, cyano, unsubstituted or R”-substituted C1-C30 linear alkyl, unsubstituted or R”-substituted C3-C20 cycloalkyl, unsubstituted or R”-substituted C7-C30 aralkyl, unsubstituted or R”-substituted C1-C30 alkoxy, unsubstituted or R”-substituted C2-C30 aliphatic hydrocarbon amine group, unsubstituted or R”-substituted C4-C30 cyclic aliphatic hydrocarbon amine group, unsubstituted or R”-substituted C6-C30 arylamine group, unsubstituted or R”-substituted C3-C30 heteroarylamine group, unsubstituted or R”-substituted C6-C30 aryloxy, unsubstituted or R”-substituted C6-C60 arylboron group, unsubstituted or R”-substituted C6-C60 aryl, unsubstituted or R”-substituted C3-C60 heteroaryl; In formula (4), X3 is selected from O, S, Se, NR 13 , CR 14 R 15 ; The said R 14 is not connected to or forms a loop with R 15 and is not connected or is connected to form a loop; R 13 , R 14 and R 15 are each independently selected from an unsubstituted or R”-substituted C1-C30 linear alkyl group, an unsubstituted or R”-substituted C3-C20 cycloalkyl group, an unsubstituted or R”-substituted C7-C30 aralkyl group, an unsubstituted or R”-substituted C1-C30 alkoxy group, an unsubstituted or R”-substituted C2-C30 aliphatic hydrocarbon amine group, an unsubstituted or R”-substituted C4-C30 cyclic aliphatic hydrocarbon amine group, an unsubstituted or R”-substituted C6-C30 arylamine group, an unsubstituted or R”-substituted C3-C30 heteroarylamine group, an unsubstituted or R”-substituted C6-C30 aryloxy group, an unsubstituted or R”-substituted C6-C60 arylboron group, an unsubstituted or R”-substituted C6-C60 aryl group, and an unsubstituted or R”-substituted C3-C60 heteroaryl group; Ring D is independently selected from one of the following unsubstituted or R”-substituted groups: benzene ring, biphenyl ring, terphenyl ring, naphthalene ring, anthracene ring, phenanthrene ring, indene ring, fluorene ring, fluoranthene ring, triphenylene ring, pyrene ring, perylene ring, cyclic ring, tetracene ring, furan ring, thiophene ring, pyrrole ring, benzofuran ring, benzothiophene ring, isobenzofuran ring, indole ring, dibenzofuran ring, dibenzothiophene ring or carbazole ring, and adjacent R”s are not connected or are connected to form a ring; Each of the above R” is independently selected from one of deuterium, halogen, cyano, C1-C20 linear alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, substituted or unsubstituted C6-C30 arylboron, C3-C30 heteroaryl.

4. The polycyclic aromatic compound according to claim 3, wherein The ring A, ring B and ring C are each independently selected from one of the following unsubstituted or R'-substituted groups: benzene ring, naphthalene ring, anthracene ring, fluorene ring, cyclopentadiene ring, indene ring, furan ring, benzofuran ring, dibenzofuran ring, indole ring, benzindole ring, carbazole ring, indolocarbazole ring, thiophene ring, benzothiophene ring, dibenzothiophene ring; The adjacent R's are not connected or are connected to form a ring; Preferably, the ring A and ring B are each independently selected from one of the following unsubstituted or R'-substituted groups: benzene ring, naphthalene ring, cyclopentadiene ring, indene ring, furan ring, benzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, and the ring C is selected from one of the following unsubstituted or R'-substituted groups: benzene ring, naphthalene ring, fluorene ring; More preferably, the ring A and ring B are each independently selected from one of the following unsubstituted or R'-substituted groups: benzene ring, indene ring, benzofuran ring, benzothiophene ring, and the ring C is an unsubstituted or R'-substituted benzene ring; R' is selected from one of deuterium, halogen, cyano, C1-C20 linear alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, substituted or unsubstituted C6-C30 arylboron group, C3-C30 heteroaryl, or a combination of one or two of them.

5. The polycyclic aromatic compound according to claim 3, characterized in that, It has a structure shown in any one of the following formulas 1-1 to 1-24: R a 、R b 、R c represent substituents from monosubstituted groups to the maximum allowable number, and adjacent R a groups, adjacent R b groups, adjacent R c groups are not connected or are connected to form a ring, and R a 、R b 、R c are each independently selected from one or a combination of two of hydrogen, deuterium, halogen, cyano, C1-C20 linear alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, C6-C30 arylboron, and C3-C30 heteroaryl; X1 and X2 are each independently O, S, NR1, CR2R3 or SiR4R5; Q1 and Q2 are each independently selected from O, S, Se, NR6, CR7R8 or SiR9R 10 ; X3 and X4 are each independently selected from O, S, NR 13 , CR 14 R 15 ; Z1, Z2, Z3, Z4, Z5 and Z6 are each independently CR 11 or N, R 11 is selected from one or a combination of two of hydrogen, deuterium, halogen, cyano, C1-C20 linear alkyl, C3-C20 cycloalkyl, C7-C30 aralkyl, C1-C10 alkoxy, C6-C30 aryloxy, C6-C30 aryl, C6-C30 arylboron, C3-C30 heteroaryl; Preferably, in formulas 1-1 to 1-24, X1 and X2 are each independently selected from O, S or NR1; R1 is selected from unsubstituted or R'-substituted C6-C60 aryl; R' is selected from one of deuterium, halogen, cyano, C1-C10 linear alkyl, C3-C10 cycloalkyl, C6-C30 aryloxy, C6-C30 aryl, C3-C30 heteroaryl; Preferably, each of X3 and X4 is independently selected from O, S or CR 14 R 15 .

6. The polycyclic aromatic compound according to claim 5, wherein In formulas 1-1 to 1-24, Said R a 、R b 、R c are each independently selected from one of hydrogen, deuterium, halogen, cyano, C1-C10 linear alkyl, C3-C10 cycloalkyl, C7-C30 aralkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C60 aryl, and C3-C60 heteroaryl; Each of Z1, Z2, Z3, Z4, Z5 and Z6 is independently CR 11 or N, and R 11 is selected from one of hydrogen, deuterium, halogen, methyl, ethyl, propyl, butyl, tert-butyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, thienyl, benzothienyl, bithienyl, terthienyl, dithienophenyl, dibenzothiophenyl, furyl, benzofuryl.

7. The polycyclic aromatic compound according to claim 1, wherein It has the following structure: Wherein -Ad represents 1-adamantyl.

8. Use of the polycyclic aromatic compound according to any one of claims 1 to 7, wherein the use is as a functional material in an organic electronic device, and the organic electronic device is selected from an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner or an electronic paper; Preferably, the use of the polycyclic aromatic compound is as a light-emitting layer material in an organic electroluminescent device, and more preferably as a light-emitting dye in the light-emitting layer.

9. An organic electroluminescent device, comprising a first electrode, a second electrode, and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer contains the polycyclic aromatic compound according to any one of claims 1 to 7; Preferably, the light-emitting functional layer includes an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, and the light-emitting layer contains the polycyclic aromatic compound according to any one of claims 1 to 7; More preferably, the light-emitting functional layer includes an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, the light-emitting layer includes a host material and a dye, and the dye includes at least one of the polycyclic aromatic compounds according to any one of claims 1 to 7.

10. A display device, characterized in that, The display device includes the organic electroluminescent device according to claim 9.

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