Compounds, mixtures and organic electronic devices

Abstract

The present invention provides a compound, a mixture and an organic electronic device, wherein the compound has a structure as shown in the general formula (1):

Description

Technical Field

[0001] The present application relates to the display field, and in particular to a compound, a mixture and an organic electronic device. Background Art

[0002] Organic Light-Emitting Diode (OLED) has broad development potential due to its advantages in the application of optoelectronic devices (such as flat panel displays and lighting) such as wide viewing angle, fast response time, low operating voltage, and thin panel thickness.

[0003] In order to improve the luminous efficiency of organic light-emitting diodes, various fluorescent and phosphorescent luminescent material systems have been developed. Whether it is fluorescent materials or phosphorescent materials, the development of excellent blue light materials is a huge challenge. Compared with blue light phosphorescent materials, organic light-emitting diodes with blue light fluorescent materials are more reliable at this stage. The current blue light emitting layer adopts a host-guest doping structure, and the blue light main material mostly adopts anthracene-based condensed ring derivatives, but the stability of this type of material is poor, resulting in a short device life, and the luminous efficiency of this type of luminescent layer material also needs to be improved. Summary of the invention

[0004] The invention provides a compound, a mixture and an organic electronic device to improve the luminous efficiency and life of the organic electronic device.

[0005] To solve the above problems, the technical solution provided by the present invention is as follows:

[0006] The present invention provides a compound having a structure as shown in general formula (1):

[0007]

[0008] wherein Ar1 is selected from an aromatic group having 6 to 18 ring atoms, or a heteroaromatic group having 6 to 13 ring atoms;

[0009] Ar2 is selected from an aromatic group containing 6 to 14 ring atoms, or a heteroaromatic group containing 13 to 19 ring atoms;

[0010] L1 and L2 are independently selected from a single bond, or a group of 6 ring atoms;

[0011] R1 and R2 are independently selected from -D, or an alkyl group of 4 C atoms, or an aromatic group of 6 to 10 ring atoms, or a heteroaromatic group of 12 ring atoms;

[0012] m1 is 0, 2, or 8;

[0013] m2 is 0 or 1.

[0014] In some embodiments of the present invention, Ar1 is selected from any of the following structures:

[0015]

[0016] Wherein, each occurrence of X is independently selected from CR3 or N;

[0017] Y is selected from CR5R6 or O;

[0018] R3 is selected from -H or -D; R5 and R6 are independently selected from methyl;

[0019] When X is a linking site, X is C.

[0020] In some embodiments of the present invention, Ar1 is selected from any of the following structures:

[0021]

[0022] In some embodiments of the present invention, Ar2 is selected from any of the following structures:

[0023]

[0024] wherein X1 is selected from CR7;

[0025] Y1 is selected from N or O;

[0026] Each occurrence of R7 is independently selected from -H.

[0027] In some embodiments of the present invention, Ar2 is selected from any of the following structures:

[0028]

[0029] In some embodiments of the present invention, L1 is selected from a single bond, or or L2 is selected from a single bond, or

[0030] In some embodiments of the present invention, R1 is selected from -D or tert-butyl; R2 is selected from or or

[0031] In some embodiments of the present invention, the compound represented by general formula (1) includes any of the following structures:

[0032]

[0033]

[0034] The present invention also provides a mixture, the mixture comprising one or more compounds according to any one embodiment of the present invention, and

[0035] Accordingly, the present invention also provides an organic electronic device, comprising a first electrode, a second electrode and an organic functional layer located between the first electrode and the second electrode, wherein the organic functional layer comprises one or more compounds described in the present invention, or the mixture described in the present invention.

[0036] The present invention provides a compound, a mixture and an organic electronic device. The compound introduces a hole transport type group with large steric hindrance into the ortho-position structure of the 9-coordinated benzene ring of anthracene, thereby improving the hole transport performance of a host material and the luminous efficiency of a light-emitting layer. On the other hand, the steric hindrance of anthracene host materials is increased, and the π-π interaction of the anthracene host materials themselves is reduced, thereby reducing the energy transfer between the host material and the guest material, reducing the triplet-triplet annihilation (TTA) and triplet polar annihilation (TPA) phenomena in the system, and improving the luminous efficiency of the light-emitting layer, as well as the service life and stability of the organic electronic device. On the other hand, the steric hindrance of the anthracene host materials is increased, and the π-π stacking of the anthracene host materials is reduced, so that the solubility of the anthracene host materials is higher, thereby making the film-forming performance of the organic functional layer including the anthracene host materials better, further improving the luminous efficiency of the light-emitting layer, as well as the service life and stability of the organic electronic device. BRIEF DESCRIPTION OF THE DRAWINGS

[0037] The technical solution and other beneficial effects of the present application will be made apparent by describing in detail the specific implementation methods of the present application in conjunction with the accompanying drawings.

[0038] Figure 1 A schematic structural diagram of an organic electronic device provided by an embodiment of the present invention. DETAILED DESCRIPTION

[0039] The following will be combined with the specific embodiments of the present invention to clearly and completely describe the technical solutions in the embodiments and / or examples of the present invention. Obviously, the embodiments and / or examples described below are only part of the embodiments and / or examples of the present invention, rather than all the embodiments and / or examples. Based on the embodiments and / or examples in the present invention, all other embodiments and / or examples obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0040] In the description of the present application, the term "including" means "including but not limited to", and the term "plurality" means "two or more". Various embodiments of the present application may be presented in the form of a range; it should be understood that the description in the form of a range is only for convenience and brevity, and should not be understood as a rigid limitation on the scope of the present application; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single numerical values ​​within the range. For example, the range description from 1 to 6 should be considered to have specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single numbers within the range, such as 1, 2, 3, 4, 5 and 6, which applies regardless of the range. In addition, whenever a numerical range is indicated herein, it is meant to include any cited number (fractional or integer) within the indicated range.

[0041] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those generally understood by those skilled in the art to which the present application belongs. The terms used herein in the specification of the present application are only for the purpose of describing specific embodiments and are not intended to limit the present application. The term "and / or" used herein includes any and all combinations of one or more of the related listed items.

[0042] In the present application, composition, printing ink and ink have the same meaning and can be interchangeable.

[0043] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0044] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0045] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0046] In the present application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that the defined group may be substituted by one or more substituents R, wherein R is selected from but not limited to deuterium atoms, cyano groups, isocyano groups, nitro groups, halogen groups, alkyl groups containing 1-20 C atoms, heterocyclic groups containing 3-20 ring atoms, aromatic groups containing 6-20 ring atoms, heteroaromatic groups containing 5-20 ring atoms, -NR'R", silane groups, carbonyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, carbamoyl groups, haloformyl groups, formyl groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups and trifluoromethyl groups, and the above groups may be further substituted by substituents acceptable in the art; it is understood that R' and R" in -NR'R" are independently selected from but not limited to H, deuterium atoms, , cyano, isocyano, nitro or halogen, alkyl containing 1-10 C atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms. Preferably, R is selected from but not limited to deuterium atom, cyano, isocyano, nitro or halogen, alkyl containing 1-10 C atoms, heterocyclic group containing 3-10 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silane group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group and trifluoromethyl group, and the above groups may also be further substituted by substituents acceptable in the art.

[0047] In the present application, the "number of ring atoms" refers to the number of atoms in the atoms constituting the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) formed by atoms bonding to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atoms. The same is true for the "number of ring atoms" described below unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0048] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which may be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For a polycyclic ring, at least one is an aromatic ring system. For example, "substituted or unsubstituted aromatic group having 6 to 40 ring atoms" refers to an aromatic group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aromatic group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, and the aromatic group may be further substituted; suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, naphthyl, fluorenyl, dinaphthylenyl, acenaphthene and derivatives thereof. It is understood that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g. <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, 9,9-diarylfluorene, triarylamine or diaryl ether systems should also be included in the definition of aromatic groups.

[0049] "Heteroaryl or heteroaromatic group" means that at least one carbon atom is replaced by a non-carbon atom on the basis of an aryl group, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" means a heteroaryl having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted, and suitable examples include but are not limited to thienyl, furanyl, pyrrolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazolyl, pyrimid ... oxazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothiophenyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-naphthyl, phenanthridinyl, primary pyridyl, quinazolinone, dibenzothiophenyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0050] In the present application, "alkyl" can represent straight chain, branched and / or cyclic alkyl. The carbon number of alkyl can be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. The limiting examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, adamantyl etc.

[0051] In the present application, "halogen" or "halo" refers to F, Cl, Br or I.

[0052] In the present application, the term "alkoxy" refers to a group having an -O-alkyl group, i.e., an alkyl group as defined above is connected to a parent core structure via an oxygen atom. Phrases containing the term, suitable examples include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt) and tert-butoxy (-OC(CH3)3 or -OtBu).

[0053] In the present application, "*" indicates a linking site.

[0054] In the present application, when a group contains multiple substituents with the same symbol, the substituents may be the same or different from each other, for example The six R1 groups on the benzene ring may be the same as or different from each other.

[0055] In the present application, the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example In which R is connected to any substitutable position of the benzene ring; express Can be used with The benzene ring can be fused at any position.

[0056] The cyclic alkyl or cycloalkyl described in the present application have the same meaning and can be interchanged.

[0057] The embodiments of the present invention provide a compound, a composition and an organic electronic device to improve the luminous efficiency and life of the organic electronic device.

[0058] In one embodiment, the compound has a structure as shown in formula (1):

[0059]

[0060] wherein Ar1 and Ar2 are selected from aromatic groups containing 6 to 60 ring atoms, or heteroaromatic groups containing 5 to 60 ring atoms, or combinations of these groups;

[0061] L1 and L2 are independently selected from a single bond, an aromatic group containing 6 to 60 ring atoms, or a heteroaromatic group containing 5 to 60 ring atoms;

[0062] R1 and R2 are each independently selected from -D, or a straight-chain alkyl group having 1 to 10 C atoms, or a straight-chain alkoxy group having 1 to 10 C atoms, or a straight-chain thioalkoxy group having 1 to 10 C atoms, or a branched-chain alkyl group having 3 to 10 C atoms, or a branched-chain alkoxy group having 3 to 10 C atoms, or a branched-chain thioalkoxy group having 3 to 10 C atoms, or a cyclic alkyl group having 3 to 10 C atoms, or a cyclic alkoxy group having 3 to 10 C atoms, or a cyclic thioalkoxy group having 3 to 10 C atoms, or a silyl group, or a keto group having 1 to 10 C atoms, or an alkoxycarbonyl group having 2 to 10 C atoms, or an aryloxycarbonyl group having 7 to 10 C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amine group, -CF3, -Cl, -Br, -F, -I, or an aromatic group having 6 to 30 ring atoms, or a heteroaromatic group having 5 to 30 ring atoms, or an aryloxy group having 5 to 30 ring atoms, or a heteroaryloxy group having 5 to 30 ring atoms;

[0063] m1 is 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0064] m2 is 0, 1, 2 or 3.

[0065] In some embodiments, each occurrence of R1 and R2 is independently selected from -D, or a straight-chain alkyl group having 1 to 20 C atoms, or a straight-chain alkoxy group having 1 to 20 C atoms, or a straight-chain thioalkoxy group having 1 to 20 C atoms, or a branched-chain alkyl group having 3 to 20 C atoms, or a branched-chain alkoxy group having 3 to 20 C atoms, or a branched-chain thioalkoxy group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 20 C atoms, or a cyclic thioalkoxy group having 3 to 20 C atoms, or a methylsilyl group. Alkyl, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amine group, -CF3, -Cl, -Br, -F, -I, or an aromatic group having 6 to 60 ring atoms, or a heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms.

[0066] In some embodiments, Ar1 is selected from a substituted or unsubstituted aromatic group containing 6 to 16 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 16 ring atoms.

[0067] Further, Ar1 is selected from any of the following structures:

[0068]

[0069] wherein X, at each occurrence, is independently selected from CR3 or N;

[0070] Y is selected from NR4, CR5R6, SiR5R6, O, S, S=O or SO2;

[0071] R3, R4, R5, R6 are each independently selected from -H, or -D, or a straight-chain alkyl group having 1 to 20 C atoms, or a straight-chain alkoxy group having 1 to 20 C atoms, or a straight-chain thioalkoxy group having 1 to 20 C atoms, or a branched-chain alkyl group having 3 to 20 C atoms, or a branched-chain alkoxy group having 3 to 20 C atoms, or a branched-chain thioalkoxy group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 20 C atoms, or a cyclic thioalkoxy group having 3 to 20 C atoms, or a silyl group, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amine group, -CF3, -Cl, -Br, -F, -I, or a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms; R5 and R6 may or may not form a ring with each other.

[0072] In the present application, when X is a linking site, X is C; when Y is a linking site, Y is N.

[0073] In some specific embodiments, each occurrence of R3 is independently selected from -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a silyl group, a cyano group, an isocyano group, a nitro group, -CF3, -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms.

[0074] Further, each occurrence of R3 is independently selected from -H, -D, a straight chain alkyl group having 1 to 8 C atoms, a branched chain alkyl group having 3 to 8 C atoms, a cyclic alkyl group having 3 to 8 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms.

[0075] The substituent in R3 is preferably -D, a straight-chain alkyl group having 1 to 4 C atoms, a branched-chain alkyl group having 3 to 4 C atoms, a phenyl group, or a pyridyl group.

[0076] In some specific embodiments, R4 is selected from a straight chain alkyl group having 1 to 10 C atoms, a branched chain alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms.

[0077] Further, R4 is selected from methyl, ethyl, isopropyl, tert-butyl, a substituted or unsubstituted aromatic group having 6 to 13 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 13 ring atoms.

[0078] Furthermore, R4 is selected from methyl, ethyl, isopropyl, tert-butyl, phenyl, pyridyl, pyrimidyl, triazine, biphenyl, terphenyl or naphthyl.

[0079] In some specific examples, R5 and R6 are selected from -H, -D, a straight chain alkyl group having 1 to 8 C atoms, a branched chain alkyl group having 3 to 8 C atoms, a cyclic alkyl group having 3 to 8 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms.

[0080] Furthermore, R5 and R6 are selected from -H, -D, methyl, ethyl, isopropyl, phenyl, pyridyl, pyrimidyl, triazine, biphenyl, terphenyl or naphthyl.

[0081] Specifically, Ar1 is selected from any of the following structures:

[0082]

[0083] Wherein, * indicates the connection site.

[0084] In some embodiments, Ar2 is selected from a substituted or unsubstituted aromatic group containing 6 to 16 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 16 ring atoms.

[0085] Further, Ar2 is selected from any of the following structures:

[0086]

[0087] Wherein, each occurrence of X1 is independently selected from CR7 or N;

[0088] Y1 is selected from NR8, CR9R 10 、SiR 11 R 12 , O, S, S=O or SO2;

[0089] R7, R8, R9, R 10Each occurrence is independently selected from -H, -D, straight-chain alkyl having 1 to 20 C atoms, straight-chain alkoxy having 1 to 20 C atoms, straight-chain thioalkoxy having 1 to 20 C atoms, branched-chain alkyl having 3 to 20 C atoms, branched-chain alkoxy having 3 to 20 C atoms, branched-chain thioalkoxy having 3 to 20 C atoms, cyclic alkyl having 3 to 20 C atoms, cyclic alkoxy having 3 to 20 C atoms, cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, 2 to 3 carbon atoms, 2 to 4 carbon ... R9 and R 10 They may or may not form a ring with each other.

[0090] In the present application, when X1 is a linking site, X1 is C; when Y1 is a linking site, Y1 is N.

[0091] In some specific embodiments, each occurrence of R7 is independently selected from -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a silyl group, a cyano group, an isocyano group, a nitro group, -CF3, -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms.

[0092] Further, each occurrence of R7 is independently selected from -H, -D, a straight chain alkyl group having 1 to 8 C atoms, a branched chain alkyl group having 3 to 8 C atoms, a cyclic alkyl group having 3 to 8 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms.

[0093] The substituent of R7 is preferably -D, a straight-chain alkyl group having 1 to 4 C atoms, a branched-chain alkyl group having 3 to 4 C atoms, a phenyl group, or a pyridyl group.

[0094] In some specific embodiments, R8 is selected from a straight-chain alkyl group having 1 to 10 C atoms, a branched alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms.

[0095] Further, R8 is selected from substituted or unsubstituted methyl, ethyl, isopropyl, tert-butyl, an aromatic group having 6 to 13 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 13 ring atoms, or a combination of these groups.

[0096] Furthermore, R8 is selected from methyl, ethyl, isopropyl, tert-butyl, phenyl, pyridyl, pyrimidyl, triazine, biphenyl, terphenyl or naphthyl.

[0097] In some specific examples, R9, R 10 is selected from -H, -D, a straight-chain alkyl group having 1 to 8 C atoms, a branched-chain alkyl group having 3 to 8 C atoms, a cyclic alkyl group having 3 to 8 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms.

[0098] Furthermore, R9, R 10 is selected from -H, -D, methyl, ethyl, isopropyl, phenyl, pyridyl, pyrimidyl, triazine, biphenyl, terphenyl or naphthyl.

[0099] Specifically, Ar2 is selected from any of the following structures:

[0100]

[0101] In some specific embodiments, L1 and L2 are each independently selected from a single bond or any of the following structures:

[0102]

[0103] Where X2 is selected independently from CR at each occurrence. 13 or N;

[0104] R 13Each occurrence is independently selected from -H, -D, straight-chain alkyl having 1 to 20 C atoms, straight-chain alkoxy having 1 to 20 C atoms, straight-chain thioalkoxy having 1 to 20 C atoms, branched-chain alkyl having 3 to 20 C atoms, branched-chain alkoxy having 3 to 20 C atoms, branched-chain thioalkoxy having 3 to 20 C atoms, cyclic alkyl having 3 to 20 C atoms, cyclic alkoxy having 3 to 20 C atoms, cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, Alkoxycarbonyl with 2 to 20 C atoms, aryloxycarbonyl with 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted aromatic radical with 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic radical with 5 to 60 ring atoms, substituted or unsubstituted aryloxy radical with 5 to 60 ring atoms, substituted or unsubstituted heteroaryloxy radical with 5 to 60 ring atoms.

[0105] Further, R 13 Each occurrence is independently selected from -H, -D, straight-chain alkyl having 1 to 4 C atoms, branched-chain alkyl having 3 to 4 C atoms, aromatic groups having 6 to 14 ring atoms, heteroaromatic groups having 6 to 14 ring atoms, aromatic groups having 6 to 14 ring atoms substituted by straight-chain alkyl having 1 to 4 C atoms or branched-chain alkyl having 3 to 4 C atoms, heteroaromatic groups having 6 to 14 ring atoms substituted by straight-chain alkyl having 1 to 4 C atoms or branched-chain alkyl having 3 to 6 C atoms.

[0106] In the present application, when X2 is a linking site, X2 is C.

[0107] Specifically, L1 and L2 are each independently selected from a single bond or any of the following groups:

[0108]

[0109]

[0110] In one embodiment, the compound represented by general formula (1) specifically includes but is not limited to any of the following structures:

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117] Example 1

[0118] The compound represented by general formula (1) is compound 1, and compound 1 is synthesized by the following synthesis route:

[0119]

[0120] Synthesis of intermediate 1-1:

[0121] 2-Chloro-1,3-dibromobenzene (27 g, 100 mmol) and dibenzofuran-2-boric acid (21 g, 100 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (500 / 50 ml), and Pd(PPh3)4 (1.8 g, 1.5 mmol) and potassium carbonate (62 g, 450 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography (eluent: PE) to obtain a white solid with a yield of 41% and MS (ASAP) = 356.0.

[0122] Synthesis of intermediate 1-2:

[0123] Intermediate 1-1 (17.8 g, 50 mmol) and phenylboronic acid (6.1 g, 50 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (250 / 50 ml), and Pd(PPh3)4 (0.88 g, 0.75 mmol) and potassium carbonate (28 g, 200 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography (eluent: DCM:PE=1:8) to obtain a white solid with a yield of 90%, MS (ASAP)=354.1.

[0124] Synthesis of compound 1:

[0125] Intermediate 1-2 (10 g, 28.2 mmol), 10-(1-naphthyl)-9-anthraceneboronic acid (9.8 g, 28.2 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd2(dba)3 (0.52 g, 0.56 mmol), s-phos (0.46 g, 1.12 mmol) and potassium carbonate (19.5 g, 141 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed (eluent was DCM:PE=1:5) and recrystallized to obtain compound 1 with a yield of 67%. MS (ASAP) = 622.2.

[0126] Example 2

[0127] The compound represented by general formula (1) is compound 2, which is synthesized by the following synthesis route:

[0128]

[0129] Synthesis of intermediate 2-1:

[0130] Intermediate 1-1 (7.1 g, 20 mmol) and 2-naphthaleneboronic acid (3.5 g, 20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (250 / 50 ml), and Pd(PPh3)4 (0.46 g, 0.4 mmol) and potassium carbonate (13.8 g, 100 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography (eluent: DCM:PE=1:8) to obtain a white solid with a yield of 84% and MS (ASAP)=404.1.

[0131] Synthesis of compound 2:

[0132] Intermediate 2-1 (10 g, 24.8 mmol), 10-phenyl-9-anthraceneboronic acid (7.4 g, 24.8 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd2(dba)3 (0.46 g, 0.5 mmol), s-phos (0.41 g, 1.0 mmol) and potassium carbonate (17 g, 124 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed (eluent was DCM:PE=1:4) and recrystallized to obtain compound 2 with a yield of 72%. MS (ASAP) = 622.2.

[0133] Example 3

[0134] The compound represented by general formula (1) is compound 3, which is synthesized by the following synthesis route:

[0135]

[0136] Synthesis of intermediate 3-1:

[0137] Intermediate 1-1 (7.1 g, 20 mmol) and 2-bromophenanthrene (4.5 g, 20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (250 / 50 ml), and Pd(PPh3)4 (0.46 g, 0.4 mmol) and potassium carbonate (13.8 g, 100 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography (eluent: DCM:PE=1:8) to obtain a white solid with a yield of 82% and MS (ASAP)=454.1.

[0138] Synthesis of compound 3:

[0139] Intermediate 3-1 (10 g, 22 mmol), 10-deuterated phenyl-9-anthraceneboronic acid (6.7 g, 22 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd2(dba)3 (0.41 g, 0.45 mmol), s-phos (0.37 g, 0.9 mmol) and potassium carbonate (15 g, 110 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed (eluent was DCM:PE=1:4) and recrystallized to obtain compound 3 with a yield of 78%. MS (ASAP) = 677.3.

[0140] Example 4

[0141] The compound represented by general formula (1) is compound 4, which is synthesized by the following synthesis route:

[0142]

[0143] Synthesis of intermediate 4-1:

[0144] 2-Chloro-1,3-dibromobenzene (27 g, 100 mmol) and dibenzofuran-2-boric acid (42 g, 200 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (500 / 50 ml), and Pd(PPh3)4 (1.8 g, 1.5 mmol) and potassium carbonate (62 g, 450 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography (eluent: DCM: PE = 1: 8) to obtain a white solid with a yield of 68% and MS (ASAP) = 444.1.

[0145] Synthesis of compound 4:

[0146] Intermediate 4-1 (10 g, 22.5 mmol), 10-(deuterated naphthyl)-9-anthraceneboronic acid (8.0 g, 22.5 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd2(dba)3 (0.41 g, 0.45 mmol), s-phos (0.37 g, 0.9 mmol) and potassium carbonate (15.5 g, 113 mmol) were added. Stir at 100 ° C for 12 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was column chromatographed (eluent was DCM:PE=1:4) and recrystallized to obtain compound 4 with a yield of 73%. MS (ASAP) = 719.3.

[0147] Example 5

[0148] The compound represented by general formula (1) is compound 5, which is synthesized by the following synthesis route:

[0149]

[0150] Synthesis of intermediate 5-1:

[0151] 9,10-Dibromoanthracene (3.4 g, 10 mmol) and 3,5-diphenyl-phenylboronic acid (2.8 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 5-1 with a yield of 69%. MS (ASAP) = 484.1.

[0152] Synthesis of intermediate 5-2

[0153] Prepare a dry 250ml three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 5-1 (5.0g, 10.3mmol), add THF (100ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop n-butyl lithium solution (4.1ml, 10.3mmol) into the reaction flask, react at -78°C for 60min, and slowly drop triethyl borate (1.5g, 10.3mmol). Let the reaction system slowly warm to room temperature and react for 12h. Add dilute hydrochloric acid, stir for 30 minutes, extract with EA, spin dry the solvent, and slurry with PE to obtain a white solid. Yield 83%. MS (ASAP) = 450.2.

[0154] Synthesis of compound 5:

[0155] Weigh intermediate 5-2 (4.5 g, 10 mmol), intermediate 1-2 (3.6 g, 10 mmol) and dissolve in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd2(dba)3 (0.18 g, 0.2 mmol), s-phos (0.16 g, 0.4 mmol) and potassium carbonate (6.9 g, 50 mmol). Stir at 100 ° C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid, organic phase column chromatography (eluent is DCM: PE = 1: 4) and recrystallization to obtain compound 5, yield: 77%.

[0156] MS (ASAP) = 724.3.

[0157] Example 6

[0158] The compound represented by general formula (1) is compound 6, which is synthesized by the following synthesis route:

[0159]

[0160] Synthesis of intermediate 6-1:

[0161] The intermediate 9-bromo-10-(2-naphthyl)anthracene (3.8 g, 10 mmol) and 2-bromo-pyridine-5-boronic acid (2.0 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed and recrystallized to obtain the intermediate 6-1 with a yield of 83%. MS (ASAP) = 459.1.

[0162] Synthesis of intermediate 6-2:

[0163] Prepare a dry 250ml three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 6-1 (5.0g, 10.9mmol), add THF (100ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop n-butyl lithium solution (4.4ml, 10.9mmol) into the reaction flask, react at -78°C for 60min, and slowly drop triethyl borate (1.6g, 10.9mmol). Let the reaction system slowly rise to room temperature and react for 12h. Add dilute hydrochloric acid, stir for 30 minutes, extract with EA, spin dry the solvent, and slurry with PE to obtain a white solid. Yield 84%. MS (ASAP) = 425.2.

[0164] Synthesis of compound 6:

[0165] Weigh intermediate 6-2 (4.3 g, 10 mmol), intermediate 2-1 (4.1 g, 10 mmol) and dissolve in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd2(dba)3 (0.18 g, 0.2 mmol), s-phos (0.16 g, 0.4 mmol) and potassium carbonate (6.9 g, 50 mmol). Stir at 100 ° C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid, organic phase column chromatography (eluent is DCM: PE = 1: 4) and recrystallization to obtain compound 6, yield: 81%.

[0166] MS (ASAP) = 749.3.

[0167] Example 7

[0168] The compound represented by general formula (1) is compound 7, which is synthesized by the following synthesis route:

[0169]

[0170] Synthesis of intermediate 7-1:

[0171] 9,10-Dibromoanthracene (6.8 g, 20 mmol), 9,9-dimethylfluorene-2-boric acid (4.8 g, 20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (2.3 g, 2 mmol) and potassium carbonate (14 g, 100 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 7-1 with a yield of 69%. MS (ASAP) = 448.1.

[0172] Synthesis of intermediate 7-2:

[0173] Prepare a dry 250ml three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 7-1 (5.0g, 11.1mmol), add THF (100ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop n-butyl lithium solution (4.5ml, 11.1mmol) into the reaction flask, react at -78°C for 60min, and slowly drop triethyl borate (1.6g, 11.1mmol). Let the reaction system slowly rise to room temperature and react for 12h. Add dilute hydrochloric acid, stir for 30 minutes, extract with EA, spin dry the solvent, and slurry with PE to obtain a white solid. Yield 94%. MS (ASAP) = 414.2.

[0174] Synthesis of compound 7:

[0175] Intermediate 7-2 (8.3 g, 20 mmol) and 1-2 (7.1 g, 20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd2(dba)3 (0.46 g, 0.5 mmol), s-phos (0.41 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed (eluent was DCM:PE=1:4) and recrystallized to obtain compound 7 with a yield of 64%. MS (ASAP) = 688.3

[0176] Example 8

[0177] The compound represented by general formula (1) is compound 8, which is synthesized by the following synthesis route:

[0178]

[0179] Synthesis of intermediate 8-1:

[0180] 9,10-Dibromoanthracene (6.8 g, 20 mmol) and 2-biphenylboronic acid (4.0 g, 20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.2 g, 1 mmol) and potassium carbonate (6.9 g, 50 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 8-1 with a yield of 76%. MS (ASAP) = 408.1.

[0181] Synthesis of intermediate 8-2:

[0182] Prepare a dry 250ml three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 8-1 (5.0g, 12mmol), add THF (100ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop n-butyl lithium solution (4.9ml, 12mmol) into the reaction flask, react at -78°C for 60min, and slowly drop triethyl borate (1.8g, 12mmol). Let the reaction system slowly rise to room temperature and react for 12h. Add dilute hydrochloric acid, stir for 30 minutes, extract with EA, spin dry the solvent, and slurry with PE to obtain a white solid. Yield 82%. MS (ASAP) = 374.2.

[0183] Synthesis of compound 8:

[0184] Intermediate 8-2 (3.7 g, 10 mmol) and 4-1 (4.4 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd2(dba)3 (0.18 g, 0.2 mmol), s-phos (0.16 g, 0.4 mmol) and potassium carbonate (6.2 g, 45 mmol) were added. Stir at 100 ° C for 12 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed and recrystallized to obtain compound 8 with a yield of 53%. MS (ASAP) = 738.3.

[0185] Example 9

[0186] The compound represented by general formula (1) is compound 9, which is synthesized by the following synthesis route:

[0187]

[0188] Synthesis of intermediate 9-1:

[0189] The intermediate 1-1 (7.1 g, 20 mmol) and (9-phenyl-9H-carbazole-3-yl)boronic acid (5.7 g, 20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (250 / 50 ml), and Pd(PPh3)4 (0.46 g, 0.4 mmol) and potassium carbonate (13.8 g, 100 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed (the eluent was DCM:PE=1:8) to obtain a white solid with a yield of 81%. MS (ASAP) = 519.1.

[0190] Synthesis of compound 9:

[0191] Intermediate 9-1 (10 g, 19.3 mmol), 10-phenyl-9-anthraceneboronic acid (5.7 g, 19.3 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd2(dba)3 (0.55 g, 0.6 mmol), s-phos (0.49 g, 1.2 mmol) and potassium carbonate (13.8 g, 100 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was column chromatographed (eluent was DCM:PE=1:4) and recrystallized to obtain compound 9 with a yield of 71%. MS (ASAP) = 737.3.

[0192] Example 10

[0193] The compound represented by general formula (1) is compound 10, and compound 10 is synthesized by the following synthesis route:

[0194]

[0195] Synthesis of intermediate 10-1:

[0196] The intermediate 9,10-dibromoanthracene (6.7 g, 20 mmol) and dibenzo[b,d]furan-2-boronic acid (4.3 g, 20 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.2 g, 1 mmol) and potassium carbonate (14 g, 100 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed and recrystallized to obtain the intermediate 10-1 with a yield of 58%. MS (ASAP) = 422.0.

[0197] Synthesis of Intermediate 10-2

[0198] Prepare a dry 250ml three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 10-1 (5.0g, 11.8mmol), add THF (100ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop n-butyl lithium solution (4.7ml, 11.8mmol) into the reaction flask, react at -78°C for 60min, and slowly drop triethyl borate (1.7g, 11.8mmol). Let the reaction system slowly rise to room temperature and react for 12h. Add dilute hydrochloric acid, stir for 30 minutes, extract with EA, spin dry the solvent, and slurry with PE to obtain a white solid. Yield 88%. MS (ASAP) = 388.1.

[0199] Synthesis of compound 10:

[0200] Intermediate 10-2 (3.9 g, 10 mmol) and 9-1 (5.2 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd2(dba)3 (0.18 g, 0.2 mmol), s-phos (0.16 g, 0.4 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Stir at 100 ° C for 12 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed and recrystallized to obtain compound 10 with a yield of 68%. MS (ASAP) = 827.3.

[0201] Embodiment 11

[0202] The compound represented by general formula (1) is compound 11, and compound 11 is synthesized by the following synthesis route:

[0203]

[0204] Synthesis of intermediate 11-1:

[0205] 9,10-Dibromoanthracene (3.4 g, 10 mmol) and fluoranthene 3-boric acid (2.5 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 11-1 with a yield of 62%. MS (ASAP) = 456.1.

[0206] Synthesis of intermediate 11-2

[0207] Prepare a dry 250ml three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 11-1 (10g, 22mmol), add THF (100ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop n-butyl lithium solution (8.8ml, 22mmol) into the reaction flask, react at -78°C for 60min, and slowly drop triethyl borate (3.2g, 22mmol). Let the reaction system slowly rise to room temperature and react for 12h. Add dilute hydrochloric acid, stir for 30 minutes, extract with EA, spin dry the solvent, and slurry with PE to obtain a white solid. Yield 89%. MS (ASAP) = 422.2.

[0208] Synthesis of compound 11:

[0209] Intermediate 11-2 (4.2 g, 10 mmol) and 2-1 (4.1 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd2(dba)3 (0.18 g, 0.2 mmol), s-phos (0.16 g, 0.4 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Stir at 100 ° C for 12 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed and recrystallized to obtain compound 11 with a yield of 61%. MS (ASAP) = 746.3.

[0210] Example 12

[0211] The compound represented by general formula (1) is compound 12, and compound 12 is synthesized by the following synthetic route:

[0212]

[0213] Synthesis of intermediate 12-1:

[0214] Intermediate 1-1 (14.2 g, 40 mmol) and 1-naphthaleneboronic acid (6.9 g, 40 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (250 / 50 ml), and Pd(PPh3)4 (0.92 g, 0.8 mmol) and potassium carbonate (27.6 g, 200 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed (eluent was DCM:PE=1:8) to obtain a white solid with a yield of 82%. MS (ASAP) = 404.1.

[0215] Synthesis of compound 12:

[0216] Intermediate 12-1 (10 g, 24.8 mmol), 10-(9-phenanthrenyl)-9-anthraceneboronic acid (9.9 g, 24.8 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd2(dba)3 (0.46 g, 0.5 mmol), s-phos (0.41 g, 1.0 mmol) and potassium carbonate (17 g, 124 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography (eluent: DCM:PE=1:4) and recrystallized to obtain compound 12 with a yield of 66%. MS (ASAP) = 722.3.

[0217] Example 13

[0218] The compound represented by general formula (1) is compound 13, and compound 13 is synthesized by the following synthesis route:

[0219]

[0220] Synthesis of intermediate 13-1:

[0221] Intermediate 1-1 (17.8 g, 50 mmol) and 2-biphenylboronic acid (9.9 g, 50 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (250 / 50 ml), and Pd(PPh3)4 (1.2 g, 1 mmol) and potassium carbonate (27.6 g, 200 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed (eluent was DCM:PE=1:8) to obtain a white solid with a yield of 77%. MS (ASAP) = 430.1.

[0222] Synthesis of compound 13:

[0223] Intermediate 13-1 (10 g, 23.3 mmol), 10-(3-pyridyl)-9-anthraceneboronic acid (7.0 g, 23.3 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd2(dba)3 (0.42 g, 0.46 mmol), s-phos (0.38 g, 0.92 mmol) and potassium carbonate (16 g, 116 mmol) were added. Stir at 100 ° C for 12 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed (eluent was DCM:PE=1:4) and recrystallized to obtain compound 13 with a yield of 62%. MS (ASAP) = 649.2.

[0224] Embodiment 14

[0225] The compound represented by general formula (1) is compound 14, and compound 14 is synthesized by the following synthesis route:

[0226]

[0227] Synthesis of intermediate 14-1:

[0228] 9,10-Dibromoanthracene (3.4 g, 10 mmol) and 1-pyreneboronic acid (2.5 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 14-1 with a yield of 71%. MS (ASAP) = 456.1.

[0229] Synthesis of intermediate 14-2:

[0230] Intermediate 14-1 (3.4 g, 10 mmol) and 4-aminophenylboronic acid (1.4 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed and recrystallized to obtain intermediate 14-2 with a yield of 71%. MS (ASAP) = 469.2.

[0231] Synthesis of intermediate 14-3:

[0232] Weigh the intermediate 14-2 (8.0g, 17mmol) in a 250ml three-necked flask, add 100ml of tetrahydrofuran, 20ml of dilute hydrochloric acid, place in an ice bath, weigh NaNO2 (1.4g, 20mmol) and dissolve in 20ml of water, slowly drop into the tetrahydrofuran solution of the intermediate 14-2, stir for 1 hour in an ice bath, weigh KI (3.4g, 20mmol) and dissolve in 50ml of water, slowly drop into the above reaction solution. React at room temperature for 12h. After the reaction is completed, add sodium thiosulfate aqueous solution, extract with dichloromethane, spin dry, wash with water, column chromatography (eluent is PE:DCM=2:1) ​​to obtain a white solid with a yield of 81%. MS (ASAP) = 580.1.

[0233] Synthesis of Intermediate 14-4

[0234] Prepare a dry 250ml three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 14-3 (10g, 17mmol), add THF (100ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop n-butyl lithium solution (6.9ml, 17mmol) into the reaction flask, react at -78°C for 60min, and then slowly drop triethyl borate (2.5g, 17mmol). Let the reaction system slowly rise to room temperature and react for 12h. Add dilute hydrochloric acid, stir for 30 minutes, extract with EA, spin dry the solvent, and slurry with PE to obtain a white solid. Yield 89%, MS (ASAP) = 498.2.

[0235] Synthesis of compound 14:

[0236] Intermediate 14-4 (5.0 g, 10 mmol) and intermediate 13-1 (4.3 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd2(dba)3 (0.18 g, 0.2 mmol), s-phos (0.16 g, 0.4 mmol) and potassium carbonate (6.9 g, 50 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography (eluent: DCM:PE=1:4) and recrystallized to obtain compound 14 with a yield of 58% and MS (ASAP)=848.3.

[0237] Embodiment 15

[0238] The compound represented by general formula (1) is compound 15, and compound 15 is synthesized by the following synthesis route:

[0239]

[0240] Synthesis of intermediate 15-1:

[0241] 4-Chloro-2,6-dibromoaniline (28.5 g, 100 mmol) and dibenzofuran-2-boric acid (42 g, 200 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (500 / 50 ml), and Pd(PPh3)4 (2.3 g, 2 mmol) and potassium carbonate (55 g, 400 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography (eluent: DCM: PE = 1: 8) to obtain a white solid with a yield of 82% and MS (ASAP) = 459.1.

[0242] Synthesis of intermediate 15-2:

[0243] Weigh the intermediate 15-1 (10 g, 21.8 mmol) in a 250 ml three-necked flask, add 100 ml of tetrahydrofuran, 20 ml of dilute hydrochloric acid, place in an ice bath, weigh NaNO2 (3.0 g, 43.6 mmol) and dissolve it in 20 ml of water, slowly drop it into the tetrahydrofuran solution of the intermediate 15-1, stir for 1 hour in an ice bath, weigh KI (7.2 g, 43.6 mmol) and dissolve it in 50 ml of water, slowly drop it into the above reaction solution. React at room temperature for 12 hours. After the reaction is completed, add sodium thiosulfate aqueous solution, extract with dichloromethane, spin dry, wash with water, column chromatography (eluent is PE:DCM=2:1) ​​to obtain a white solid with a yield of 43%, MS (ASAP)=570.0.

[0244] Synthesis of intermediate 15-3

[0245] Intermediate 15-2 (10 g, 17.5 mmol), 10-(1-naphthyl)-9-anthraceneboronic acid (6.1 g, 17.5 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd2(dba)3 (0.32 g, 0.35 mmol), s-phos (0.29 g, 0.7 mmol) and potassium carbonate (12 g, 88 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography (eluent: DCM:PE=1:5) and recrystallized to obtain compound 15 with a yield of 62% and MS (ASAP)=746.2.

[0246] Synthesis of compound 15:

[0247] Intermediate 15-3 (7.5 g, 10 mmol) and 1-naphthaleneboronic acid (1.7 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd2(dba)3 (0.18 g, 0.2 mmol), s-phos (0.16 g, 0.4 mmol) and potassium carbonate (6.9 g, 50 mmol) were added. The mixture was stirred at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain compound 15 with a yield of 82% and MS (ASAP) = 838.3.

[0248] Example 16

[0249] The compound represented by general formula (1) is compound 16, and compound 16 is synthesized by the following synthesis route:

[0250]

[0251] Synthesis of intermediate 16-1:

[0252] The intermediate 9-bromo-10-(1-naphthyl)anthracene-1,2,3,4,5,6,7,8-d8 (3.9 g, 10 mmol) and 2-chloro-pyridine-5-boronic acid (1.6 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (4.1 g, 30 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed and recrystallized to obtain the intermediate 16-1 with a yield of 82%. MS (ASAP) = 423.2.

[0253] Synthesis of intermediate 16-2:

[0254] Prepare a dry 250ml three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 16-1 (4.2g, 10mmol), add THF (100ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop tert-butyl lithium solution (4.0ml, 10mmol) into the reaction flask, react at -78°C for 60min, and slowly drop triethyl borate (2.2g, 15mmol). Let the reaction system slowly warm to room temperature and react for 12h. Add dilute hydrochloric acid, stir for 30 minutes, extract with EA, spin dry the solvent, and slurry with PE to obtain a white solid. Yield 84%. MS (ASAP) = 433.2.

[0255] Synthesis of compound 16:

[0256] Weigh the intermediate 16-2 (4.3 g, 10 mmol), dissolve the intermediate 1-2 (3.5 g, 10 mmol) in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and add Pd2(dba)3 (0.18 g, 0.2 mmol), s-phos (0.16 g, 0.4 mmol) and potassium carbonate (6.9 g, 50 mmol). Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and perform organic phase column chromatography (eluent is DCM:PE=1:4) and recrystallize to obtain compound 16 with a yield of 81%.

[0257] MS (ASAP) = 707.3.

[0258] Embodiment 17

[0259] The compound represented by general formula (1) is compound 17, and compound 17 is synthesized by the following synthesis route:

[0260]

[0261] Synthesis of intermediate 17-1:

[0262] 9,10-Dibromo-2,6-di-tert-butylanthracene (4.5 g, 10 mmol) and 1-biphenylboronic acid (2.0 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 17-1 with a yield of 73%. MS (ASAP) = 520.2.

[0263] Synthesis of intermediate 17-2:

[0264] Intermediate 17-1 (5.2 g, 10 mmol) and 4-aminophenylboronic acid (1.4 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed and recrystallized to obtain intermediate 17-2 with a yield of 76%. MS (ASAP) = 533.3.

[0265] Synthesis of intermediate 17-3:

[0266] Weigh the intermediate 17-2 (5.3 g, 10 mmol) in a 250 ml three-necked flask, add 100 ml of tetrahydrofuran, 20 ml of dilute hydrochloric acid, place in an ice bath, weigh NaNO2 (1.4 g, 20 mmol) and dissolve in 20 ml of water, slowly drop into the tetrahydrofuran solution of the intermediate 17-2, stir for 1 hour in an ice bath, weigh KI (3.4 g, 20 mmol) and dissolve in 50 ml of water, slowly drop into the above reaction solution. Reaction at room temperature for 12 hours. After the reaction is completed, add sodium thiosulfate aqueous solution, extract with dichloromethane, spin dry, wash with water, column chromatography (eluent is PE:DCM=2:1) ​​to obtain a white solid with a yield of 85%. MS (ASAP) = 644.2.

[0267] Synthesis of intermediate 17-4:

[0268] Prepare a dry 250ml three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 17-3 (6.4g, 10mmol), add THF (100ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop n-butyl lithium solution (4.0ml, 10mmol) into the reaction flask, react at -78°C for 60min, and slowly drop triethyl borate (2.5g, 17mmol). Let the reaction system slowly rise to room temperature and react for 12h. Add dilute hydrochloric acid, stir for 30 minutes, extract with EA, spin dry the solvent, and slurry with PE to obtain a white solid. Yield 84%. MS (ASAP) = 562.3.

[0269] Synthesis of compound 17:

[0270] Intermediate 17-4 (5.6 g, 10 mmol) and intermediate 13-1 (4.3 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd2(dba)3 (0.18 g, 0.2 mmol), s-phos (0.16 g, 0.4 mmol) and potassium carbonate (6.9 g, 50 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed (eluent was DCM:PE=1:4) and recrystallized to obtain compound 17 with a yield of 52%.

[0271] MS (ASAP) = 912.4.

[0272] Embodiment 18

[0273] The compound represented by general formula (1) is compound 17, and compound 17 is synthesized by the following synthesis route:

[0274]

[0275] Synthesis of intermediate 18-1:

[0276] 2-Chloro-1,3-dibromo-5-tert-butylbenzene (32.6 g, 100 mmol) and dibenzofuran-2-boric acid (42.4 g, 200 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (500 / 50 ml), and Pd(PPh3)4 (1.8 g, 1.5 mmol) and potassium carbonate (62 g, 450 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography (eluent: DCM:PE=1:8) to obtain a white solid with a yield of 61%. MS (ASAP) = 500.2.

[0277] Synthesis of compound 18:

[0278] Intermediate 18-1 (5.0 g, 10 mmol), 9-boronic acid-10-(1-naphthyl)anthracene-1,2,3,4,5,6,7,8-d8 (3.6 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd2(dba)3 (0.41 g, 0.45 mmol), s-phos (0.37 g, 0.9 mmol) and potassium carbonate (6.9 g, 50 mmol) were added. Stir at 100 ° C for 12 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed (eluent was DCM:PE=1:4) and recrystallized to obtain compound 18 with a yield of 68%. MS (ASAP) = 776.4.

[0279] Embodiment 19

[0280] The compound represented by general formula (1) is compound 16, and compound 16 is synthesized by the following synthesis route:

[0281]

[0282] Synthesis of intermediate 19-1:

[0283] Dissolve 2,5-dichloro-1,4-dibromo-3,6-diiodobenzene (55.7 g, 100 mmol) and dibenzofuran-2-boric acid (42.4 g, 200 mmol) in a mixed solvent of 1,4-dioxane and water (500 / 50 ml), and add Pd(PPh3)4 (1.8 g, 1.5 mmol) and potassium carbonate (69 g, 500 mmol). Stir at 100 ° C for 12 h under nitrogen atmosphere. After cooling, remove most of the solvent by rotary evaporation, then extract and wash the liquid with water, and obtain a white solid by organic phase column chromatography (eluent is PE), with a yield of 43%. MS (ASAP) = 637.2.

[0284] Synthesis of intermediate 19-2:

[0285] Intermediate 19-1 (31.9 g, 50 mmol) and phenylboronic acid (24.4 g, 100 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (250 / 50 ml), and Pd(PPh3)4 (0.88 g, 0.75 mmol) and potassium carbonate (28 g, 200 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed (eluent was DCM:PE=1:8) to obtain a white solid with a yield of 92%. MS (ASAP) = 630.1.

[0286] Synthesis of intermediate 19-3:

[0287] Intermediate 19-2 (63 g, 100 mmol), 10-(1-naphthyl)-9-anthraceneboronic acid (34.8 g, 100 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd2(dba)3 (0.92 g, 1 mmol), s-phos (0.82 g, 2 mmol) and potassium carbonate (69 g, 500 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was column chromatographed (eluent was DCM:PE=1:5) and recrystallized to obtain compound 19-3 with a yield of 64%. MS (ASAP) = 898.3.

[0288] Synthesis of compound 19:

[0289] Intermediate 19-3 (89.8 g, 100 mmol) and phenylboronic acid (12.2 g, 100 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd2(dba)3 (0.92 g, 1 mmol), s-phos (0.82 g, 2 mmol) and potassium carbonate (69 g, 500 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was column chromatographed (eluent was DCM: PE = 1: 5) and recrystallized to obtain compound 19 with a yield of 67%.

[0290] MS (ASAP) = 940.3.

[0291] Embodiment 20

[0292] The compound represented by general formula (1) is compound 20, which is synthesized by the following synthesis route:

[0293]

[0294] Synthesis of intermediate 20-1:

[0295] 9,10-Dibromoanthracene (3.4 g, 10 mmol) and 5-chloro-2-pyridineboronic acid (1.6 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 20-1 with a yield of 73%. MS (ASAP) = 369.0.

[0296] Synthesis of intermediate 20-2:

[0297] Intermediate 20-1 (3.7 g, 10 mmol) and 4-aminophenylboronic acid (1.4 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed and recrystallized to obtain intermediate 20-2 with a yield of 67%. MS (ASAP) = 380.1.

[0298] Synthesis of intermediate 20-3:

[0299] Intermediate 20-2 (3.8 g, 10 mmol) and phenylboronic acid (1.2 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (100 / 10 ml), and Pd(PPh3)4 (1.15 g, 1 mmol) and potassium carbonate (8.3 g, 60 mmol) were added. Stir at 100°C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water. The organic phase was column chromatographed and recrystallized to obtain intermediate 20-3 with a yield of 76%. MS (ASAP) = 422.2.

[0300] Synthesis of intermediate 20-4:

[0301] Weigh the intermediate 20-3 (4.2g, 10mmol) in a 250ml three-necked flask, add 100ml of tetrahydrofuran, 20ml of dilute hydrochloric acid, place in an ice bath, weigh NaNO2 (1.4g, 20mmol) and dissolve in 20ml of water, slowly drop into the tetrahydrofuran solution of the intermediate 20-2, stir for 1 hour in an ice bath, weigh KI (3.4g, 20mmol) and dissolve in 50ml of water, slowly drop into the above reaction solution. Reaction at room temperature for 12h. After the reaction is completed, add sodium thiosulfate aqueous solution, extract with dichloromethane, spin dry, wash with water, column chromatography (eluent is PE:DCM=2:1) ​​to obtain a white solid with a yield of 79%. MS (ASAP) = 533.1.

[0302] Synthesis of intermediate 20-5:

[0303] Prepare a dry 250ml three-necked flask, set up the reaction device, evacuate and pass nitrogen; keep nitrogen flowing in the reaction flask, weigh 20-4 (5.3g, 10mmol), add THF (100ml), evacuate and pass nitrogen for three cycles, and cool to -78°C; slowly drop n-butyl lithium solution (4.0ml, 10mmol) into the reaction flask, react at -78°C for 60min, and slowly drop triethyl borate (2.5g, 17mmol). Let the reaction system slowly rise to room temperature and react for 12h. Add dilute hydrochloric acid, stir for 30 minutes, extract with EA, spin dry the solvent, and slurry with PE to obtain a white solid. Yield 82%. MS (ASAP) = 451.2.

[0304] Synthesis of compound 20:

[0305] Intermediate 20-5 (4.5 g, 10 mmol) and intermediate 2-1 (4.0 g, 10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 / 20 ml), and Pd2(dba)3 (0.18 g, 0.2 mmol), s-phos (0.16 g, 0.4 mmol) and potassium carbonate (6.9 g, 50 mmol) were added. Stir at 100 ° C for 12 h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the liquid was extracted and washed with water, and the organic phase was column chromatographed (eluent was DCM:PE=1:4) and recrystallized to obtain compound 20 with a yield of 53%.

[0306] MS (ASAP) = 775.3.

[0307] The present invention also provides a mixture, which comprises one or more compounds represented by general formula (1) and one or more organic functional materials, wherein the organic functional materials are selected from hole injection materials (HIM), hole transport materials (HTM), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), luminescent materials (Emitter), host materials (Host) or organic dyes, etc.

[0308] In one embodiment, the organic functional material is selected from guest materials. Further, the organic functional material is selected from blue light guest materials.

[0309] In one specific embodiment, the guest material includes a compound represented by formula (2):

[0310]

[0311] wherein Ar3-Ar6 are independently selected from a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 60 ring atoms;

[0312] R 14 Each occurrence is independently selected from -H, -D, straight-chain alkyl having 1 to 20 C atoms, straight-chain alkoxy having 1 to 20 C atoms, straight-chain thioalkoxy having 1 to 20 C atoms, branched-chain alkyl having 3 to 20 C atoms, branched-chain alkoxy having 3 to 20 C atoms, branched-chain thioalkoxy having 3 to 20 C atoms, cyclic alkyl having 3 to 20 C atoms, cyclic alkoxy having 3 to 20 C atoms, cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, amine, CF3, Cl, Br, F, I, substituted or unsubstituted aromatic radical having 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic radical having 5 to 60 ring atoms, substituted or unsubstituted aryloxy radical having 5 to 60 ring atoms, substituted or unsubstituted heteroaryloxy radical having 5 to 60 ring atoms;

[0313] s is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0314] Preferably, Ar3-Ar6 are independently selected from substituted or unsubstituted aromatic groups containing 6 to 14 ring atoms, or substituted or unsubstituted heteroaromatic groups containing 6 to 14 ring atoms.

[0315] Specifically, Ar3-Ar6 are independently selected from any of the following structures:

[0316]

[0317] Each occurrence of V is independently selected from CR 15 or N;

[0318] W is selected from NR 16 , CR 16 R 17 、SiR 16 R 17 , O, S, S=O or SO2;

[0319] R 15 -R 17 Each occurrence is independently selected from -H, -D, straight-chain alkyl having 1 to 20 C atoms, straight-chain alkoxy having 1 to 20 C atoms, straight-chain thioalkoxy having 1 to 20 C atoms, branched-chain alkyl having 3 to 20 C atoms, branched-chain alkoxy having 3 to 20 C atoms, branched-chain thioalkoxy having 3 to 20 C atoms, cyclic alkyl having 3 to 20 C atoms, cyclic alkoxy having 3 to 20 C atoms, cyclic thioalkoxy having 3 to 20 C atoms, or silyl, keto having 1 to 20 C atoms , alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, CF3, Cl, Br, F, I, substituted or unsubstituted aromatic radicals having 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic radicals having 5 to 60 ring atoms, substituted or unsubstituted aryloxy radicals having 5 to 60 ring atoms, substituted or unsubstituted heteroaryloxy radicals having 5 to 60 ring atoms.

[0320] Preferably, R 15 -R 17 Each occurrence is independently selected from -H, -D, straight-chain alkyl having 1 to 10 C atoms, branched-chain alkyl having 3 to 10 C atoms, cyclic alkyl having 3 to 10 C atoms, substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 30 ring atoms.

[0321] More preferably, R 15 -R 17 Each occurrence is independently selected from -H, -D, straight chain alkyl having 1 to 10 C atoms, or branched or cyclic alkyl having 3 to 10 C atoms, or phenyl.

[0322] Specifically, the compound represented by the general formula (2) is selected from the compounds represented by the following general formula:

[0323]

[0324] Preferably, the compound represented by general formula (2) is selected from the compounds represented by the following general formula:

[0325]

[0326] More specifically, the compounds represented by general formula (2) include but are not limited to the following structures:

[0327]

[0328]

[0329] The present invention also provides a composition, comprising one or more compounds represented by general formula (1) or one or more mixtures thereof, and an organic solvent, wherein the mass percentage of the compound or mixture is 0.01% to 10%, preferably 0.1% to 8%, more preferably 0.2% to 5%, and most preferably 0.25% to 3%.

[0330] The organic solvent is selected from aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, or boric acid esters or phosphate esters.

[0331] Aromatic or heteroaromatic solvents suitable for the present invention include, but are not limited to: p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3- Isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, etc.

[0332] Aromatic ketone solvents suitable for the present invention include but are not limited to: 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.

[0333] Aromatic ether solvents suitable for the present invention include, but are not limited to, 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl ethyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, and ethyl-2-naphthyl ether.

[0334] Aliphatic ketone solvents suitable for the present invention include but are not limited to: 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; or aliphatic ethers, for example, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0335] Ester solvents suitable for the present invention include, but are not limited to, alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate are particularly preferred.

[0336] The organic solvent may be used alone or as a mixture of two or more organic solvents.

[0337] In some embodiments, the organic solvent further comprises one or more of the following compounds: methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, and indene.

[0338] Preferably, the organic solvent is a solvent having a Hansen solubility parameter within the following range:

[0339] δd (dispersion force) is in the range of 17.0 to 23.2 MPa1 / 2, especially in the range of 18.5 to 21.0 MPa1 / 2;

[0340] δp (polar force) is in the range of 0.2 to 12.5 MPa1 / 2, especially in the range of 2.0 to 6.0 MPa1 / 2;

[0341] δh (hydrogen bonding force) is in the range of 0.9 to 14.2 MPa1 / 2, and particularly in the range of 2.0 to 6.0 MPa1 / 2.

[0342] The boiling point of the organic solvent is greater than or equal to 150° C., preferably greater than or equal to 180° C., more preferably greater than or equal to 200° C., more preferably greater than or equal to 250° C., and most preferably greater than or equal to 300° C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet print head. The organic solvent can be evaporated from the solvent system to form a film containing a functional material.

[0343] The composition can be a solution or a suspension.

[0344] The composition can be used as a coating or printing ink to prepare organic electronic devices, and the corresponding preparation methods include but are not limited to inkjet printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roller printing, lithography, flexographic printing, rotary printing, spraying, brushing or pad printing, slot extrusion coating, etc. The preferred ones are gravure printing, spray printing and inkjet printing. The solution or suspension may further include one or more components, such as surfactant compounds, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc.

[0345] Please refer to Figure 1Correspondingly, the present invention further provides an organic electronic device, which includes a first electrode 11, a second electrode 12 and an organic functional layer 13 located between the first electrode 11 and the second electrode 12, and the organic functional layer 13 includes a film structure prepared from the compound, mixture or composition described in any embodiment of the present invention.

[0346] The organic electronic device includes, but is not limited to, an organic light emitting diode, an organic photovoltaic cell, an organic light emitting cell, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spin electronic device, an organic sensor, an organic plasmon emission diode, etc.; the organic electronic device is preferably an organic light emitting diode. The organic electronic device can be applied to various electronic devices, including, but not limited to, display devices, lighting devices, light sources, sensors, etc.

[0347] In a specific embodiment, the organic functional layer 13 includes a light emitting layer (EML) 131, a hole transport layer (HTL) 132 and an electron transport layer (ETL) 133. Further, the organic functional layer 13 also includes a hole injection layer (HIL) 134 and / or an electron injection layer (EIL) 135. The first electrode 11 is an anode, and the second electrode 12 is a cathode.

[0348] The anode may include a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into the hole injection layer (HIL) or the hole transport layer (HTL) or the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the anode and the HOMO energy level or valence band energy level of the light-emitting body in the light-emitting layer or the p-type semiconductor material as the HIL or HTL or the electron blocking layer (EBL) is less than 0.5eV, preferably less than 0.3eV, and most preferably less than 0.2eV. Anode materials include but are not limited to Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. The anode material can be deposited using any suitable technique, such as physical vapor deposition, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0349] The cathode may include a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL or ETL or directly into the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the luminophore in the light-emitting layer or the n-type semiconductor material as the electron injection layer (EIL) or the electron transport layer (ETL) or the hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Cathode materials include but are not limited to Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material can be deposited using any suitable technique, such as physical vapor deposition, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0350] In a specific embodiment, Figure 1 As shown, the organic electronic device includes a substrate 10, an anode (ITO) 11, a hole injection layer (HIL) 134, a hole transport layer (HTL) 132, an emission layer (EML) 131, an electron transport layer (ETL) 133 and a cathode 12. The steps of preparing the organic electronic device are as follows:

[0351] a. preparing an ITO conductive glass substrate, and cleaning the ITO conductive glass substrate with a solvent (such as one or more of chloroform, acetone or isopropanol), and then performing an ultraviolet ozone treatment;

[0352] b. Using PEDOT (polyethylenedioxythiophene, CleviosAI4083) as the HIL material, a 60 nm thin film was deposited on an ITO conductive glass substrate by spin coating in a clean room, and then treated on a hot plate at 180°C for 10 minutes to obtain a 40 nm hole injection layer;

[0353] c. Using PVK (Sigma Aldrich, average Mn 25000-50000) as the HTL material, a 20 nm thin film was deposited on the HIL by spin coating in a nitrogen glove box, and then treated on a hot plate at 180°C for 60 minutes; the solution used for spin coating was PVK added to toluene solvent, and the solution solubility was 5 mg / ml;

[0354] d. Using a methyl benzoate solution including host and guest materials as the EML material, a thin film is deposited on the HTL by spin coating in a nitrogen glove box, and then treated on a hot plate at 140° C. for 10 minutes; the host and guest materials include a host material that is a compound represented by the general formula (1) provided in an embodiment of the present invention, and a guest material that is a compound represented by the general formula (2) provided in an embodiment of the present invention, the weight ratio of the host material to the guest material is 95:5, and the solution solubility is 15 mg / ml;

[0355] e. Transfer the heat-treated substrate to a vacuum chamber and then Placed in different evaporation units, under high vacuum (1×10 -6 mbar) at a ratio of 50 wt % to form an electron transport layer of 20 nm on the light-emitting layer; and then an Al cathode with a thickness of 100 nm was deposited.

[0356] f. In a nitrogen glove box, encapsulate the device with ultraviolet curing resin.

[0357] The above compounds 1 to 20 and the following compounds BH-ref-01 and BH-ref-02 were used as host materials, and the above BD-1 was used as a guest material. The above preparation steps were used to prepare the corresponding organic electronic devices OLED-1 to OLED-20, OLED-ref1 and OLED-ref2, respectively.

[0358]

[0359] The performance of OLED-1 to OLED-20, OLED-ref1 and OLED-ref2 was characterized, and the performance parameters of each organic electronic device were obtained as shown in Table 1 below.

[0360] Table 1

[0361]

[0362]

[0363] After testing, the color coordinates of the blue light devices prepared using compounds 1 to 20 as the main materials in the EML layer light-emitting layer are better than those of the comparative compounds BH-ref-01 and BH-ref-02. In addition, the luminous efficiency of the blue light devices prepared using compounds 1 to 20 as the main materials in the EML layer light-emitting layer is in the range of 5-8cd / A, which has a more excellent luminous efficiency. Furthermore, the time when the brightness of the blue light devices prepared using compounds 1 to 20 as the main materials in the EML layer light-emitting layer decays to 90% is more than 300 hours, which has a longer service life.

[0364] Anthracene and pyrene both have large rigid planes and large conjugated π electron systems. When fused ring derivatives of anthracene are used as host materials and fused ring derivatives of pyrene are used as guest materials in organic electronic devices, there is a large mutual spatial interaction between the host material and the guest material, so that the triplet energy of the host material is transferred to the guest material, which ultimately affects the service life of the organic electronic device. In addition, the materials of the existing organic functional layer are usually prepared by coating or inkjet printing. Therefore, the solubility of the host material affects the film uniformity of the organic functional material, thereby affecting the luminous efficiency and service life of the organic electronic device.

[0365] The embodiment of the present invention introduces a hole-transporting group with large steric hindrance into the ortho-position structure of the 9-coordinated benzene ring of anthracene, thereby improving the hole transport performance of the host material and the luminescence efficiency of the light-emitting layer on the one hand; on the other hand, the steric hindrance of the anthracene host material is increased, and the π-π interaction of the anthracene host material itself is reduced, thereby reducing the energy transfer between the host material and the guest material, reducing the triplet-triplet annihilation (TTA) and triplet polar annihilation (TPA) phenomena in the system, and improving the luminescence efficiency of the light-emitting layer, as well as the service life and stability of the organic electronic device; on another hand, the steric hindrance of the anthracene host material is increased, and the π-π stacking of the anthracene host material is reduced, so that the solubility of the anthracene host material is higher, thereby making the film-forming performance of the organic functional layer including the anthracene host material better, further improving the luminescence efficiency of the light-emitting layer, as well as the service life and stability of the organic electronic device.

[0366] The compounds, mixtures and organic electronic devices provided in the embodiments of the present invention are introduced in detail above. Specific examples are used herein to illustrate the principles and implementation methods of the present invention. The description of the above embodiments is only used to help understand the method of the present invention and its core idea. At the same time, for those skilled in the art, according to the idea of ​​the present invention, there will be changes in the specific implementation methods and application scopes. In summary, the content of this specification should not be understood as limiting the present invention.

Claims

1. A compound, characterized in that The compound has a structure as shown in general formula (1): Wherein, Ar1 is selected from any of the following structures: Ar2 is selected from any of the following structures: L1 is selected from a single bond, or L2 is selected from a single bond, or R1 and R2 are independently selected from -D, or an alkyl group of 4 C atoms, or an aromatic group of 6 to 10 ring atoms, or a heteroaromatic group of 12 ring atoms; m1 is 0, 2, or 8; m2 is 0 or 1.

2. The compound according to claim 1, characterized in that R1 is selected from -D or tert-butyl; R2 is selected from 3. The compound according to claim 1, characterized in that The compounds represented by the general formula (1) include any of the following structures:

4. A mixture, characterized in that The mixture comprises one or more compounds according to any one of claims 1 to 3, and 5. An organic electronic device, characterized in that: The organic electronic device comprises a first electrode, a second electrode and an organic functional layer located between the first electrode and the second electrode, wherein the organic functional layer comprises one or more compounds according to any one of claims 1 to 3 or the mixture according to claim 4.

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