Arylamine compound, composition and organic electroluminescent device

Abstract

The invention discloses an arylamine compound, a composition and an organic electroluminescent device. The structural general formula of the compound is shown as a formula (1): # imgabs0, wherein a ring A is selected from the following formula (2) or formula (3): # imgabs1 # R1w, R1x, R1y, R1z and R2-R7, and at least one of the following formula (4) or formula (5): # imgabs2 # imgabs3. The compound has the advantages of low sublimation temperature, low driving voltage, high luminous efficiency, long device service life and the like, and can be used as a main body material in an OLED (Organic Light Emitting Diode) luminescent device.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescence, and particularly relates to an aromatic amine compound, a composition and an organic electroluminescence device. Background Art

[0002] At present, organic electroluminescent devices (OLEDs), as a new generation of display and lighting technology, are receiving more and more attention in the market, and their application prospects are very broad, covering multiple fields such as display screens, sensors and high-efficiency lighting. However, compared with market demand, existing OLED devices still have a lot of room for improvement in key performance indicators such as luminous efficiency, driving voltage and service life.

[0003] The basic structure of an OLED device is similar to a "sandwich", including metal electrodes and multiple layers of organic functional films sandwiched between them. Driven by current, electrons and holes are injected from the positive and negative electrodes respectively. After moving a certain distance, the holes and electrons are recombined in the light-emitting layer and released in the form of light or heat, thereby achieving a luminescent effect. In recent years, phosphorescent OLEDs have attracted widespread attention as a highly efficient luminescent technology. Their performance depends not only on the triplet light-emitting body used, but also on other device materials, especially the selection of the host material. The host material plays a significant role in reducing the driving voltage of the device, improving the luminous efficiency, and extending the service life of the device.

[0004] At present, the performance of traditional host materials is still insufficient, especially in meeting the requirements of low driving voltage, high luminous efficiency and long life, there is still significant room for optimization. Therefore, the development of new high-performance host materials has become a key technical requirement to further improve the overall performance of OLED devices. Summary of the invention

[0005] The present invention aims to solve at least one of the technical problems existing in the above-mentioned prior art. To this end, the present invention provides an aromatic amine compound, a composition thereof and an organic electroluminescent device. The aromatic amine compound can be used as a main material of an OLED light-emitting device, which can significantly reduce the driving voltage of the device, improve the luminous efficiency, and extend the service life of the device, thereby significantly improving the overall performance of the OLED device.

[0006] Specifically, the first aspect of the present invention relates to an aromatic amine compound, the structure of which is shown in formula (1):

[0007]

[0008] Wherein, ring A is selected from the following formula (2) or formula (3):

[0009]

[0010] Wherein, * represents the site of fusion with the five-membered ring containing X in formula (1);

[0011] R 1w , R 1x , R 1y , R 1z , at least one of R2-R7 is selected from the following formula (4) or formula (5):

[0012]

[0013] * represents the connection site with the naphthalene ring in formula (2) or (3);

[0014] X1-X 10 are independently selected from CR0 or N;

[0015] And, -LN(Ar1)(Ar2) replaces R2-R6, R 1w , R 1y , R 1z Any one of;

[0016] The rest R 1w , R 1x , R 1y , R 1z , R2-R7 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphino or C6-C60 arylamine;

[0017] each R0 is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphino or C6-C60 arylamine;

[0018] X is selected from O, S, Se or NR a ;

[0019] R aSelected from C1-C30 alkyl, C1-C30 heteroalkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 alkylsilyl or C6-C30 arylsilyl;

[0020] Wherein, a represents an integer of 0-4; when a is an integer of 2-4, each R1 is the same or different;

[0021] L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C6-C60 heteroarylene group;

[0022] Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C36 aryl group or a substituted or unsubstituted C2-C36 heteroaryl group;

[0023] In said L, Ar1 and Ar2, said substitution is independently substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl substituted amine, C1-C6 hydrocarbon substituted or unsubstituted C6-C30 aryl or C1-C6 hydrocarbon substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions is from a single substitution to the maximum number of substitutions;

[0024] The heteroatoms in the heteroarylene group, heteroaryl group, heteroalkyl group or heterocycloalkyl group are independently selected from at least one of O, S, N, Se, Si or Ge.

[0025] The beneficial effects of the present invention are as follows:

[0026] The aromatic amine compound of the present invention has the advantages of low sublimation temperature, low driving voltage, high luminous efficiency, long device life, etc., and can be used as a main material in OLED light-emitting devices, especially in red light-emitting devices. The aromatic amine compound can be used to prepare semiconductor devices such as displays, and has application potential in the AMOLED (active matrix organic light-emitting diode) industry. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] Figure 1 Compound A30 of the present invention 1 HNMR spectrum;

[0028] Figure 2 FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present invention. DETAILED DESCRIPTION

[0029] In order to make the technical scheme of the present invention more clearly understood by those skilled in the art, the following embodiments are listed for illustration. It should be pointed out that the following embodiments do not limit the protection scope of the present invention.

[0030] The first embodiment of the present invention provides an aromatic amine compound, the structure of which is shown in formula (1):

[0031]

[0032] Wherein, ring A is selected from the following formula (2) or formula (3):

[0033]

[0034] Wherein, * represents the site of fusion with the five-membered ring containing X in formula (1);

[0035] R 1w , R 1x , R 1y , R 1z , at least one of R2-R7 is selected from the following formula (4) or formula (5):

[0036]

[0037] * represents the connection site with the naphthalene ring in formula (2) or (3);

[0038] X1-X 10 are independently selected from CR0 or N;

[0039] And, -LN(Ar1)(Ar2) replaces R2-R6, R 1w , R 1y , R 1z Any one of;

[0040] The rest R 1w , R 1x , R 1y , R 1z , R2-R7 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphino or C6-C60 arylamine;

[0041] each R0 is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphino, or C6-C60 arylamine;

[0042] X is selected from O, S, Se or NR a ;

[0043] R a Selected from C1-C30 alkyl, C1-C30 heteroalkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 alkylsilyl or C6-C30 arylsilyl;

[0044] Wherein, a represents an integer of 0-4; when a is an integer of 2-4, each R1 is the same or different;

[0045] L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C6-C60 heteroarylene group;

[0046] Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C36 aryl group or a substituted or unsubstituted C2-C36 heteroaryl group;

[0047] In said L, Ar1 and Ar2, said substitution is independently substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl substituted amine, C1-C6 hydrocarbon substituted or unsubstituted C6-C30 aryl or C1-C6 hydrocarbon substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions is from a single substitution to the maximum number of substitutions;

[0048] The heteroatoms in the heteroarylene group, heteroaryl group, heteroalkyl group or heterocycloalkyl group are independently selected from at least one of O, S, N, Se, Si or Ge.

[0049] It should be understood that “the rest of R 1w , R 1x , R 1y , R 1z , R2-R7" refers to, R 1w , R 1x , R 1y , R 1z, R2 to R7, except for the part selected from the structure of formula (4) or formula (5) and the part replaced by -LN(Ar1)(Ar2).

[0050] In some embodiments, formula (1) is selected from one of the structures shown in the following formulas (A-1) to (A-9):

[0051]

[0052] In some embodiments, X is selected from O, S or NR a , R a Selected from C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl or C6-C20 aryl.

[0053] In some embodiments, X is selected from O, S or NR a , R a Selected from C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl or C6-C20 aryl.

[0054] In some embodiments, X is selected from O, S or NR a , R a Selected from C6-C20 aryl groups, such as R a Specifically, it may be phenyl, biphenyl or naphthyl.

[0055] In some embodiments, the L is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C6-C30 heteroarylene group.

[0056] In some embodiments, the L is selected from a single bond, a substituted or unsubstituted C6-C20 arylene group, or a substituted or unsubstituted C6-C20 heteroarylene group.

[0057] In some embodiments, the L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.

[0058] In some embodiments, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C26 aryl group or a substituted or unsubstituted C2-C26 heteroaryl group.

[0059] In some embodiments, Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted Ar1, Ar2, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted fluoranthene, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted triphenylene radical, substituted or unsubstituted tetramethyltetrahydronaphthyl, substituted or unsubstituted phenanthrothiazolyl or substituted or unsubstituted phenanthroxazolyl or a combination of at least two of the above. "A combination of at least two of the above" refers to at least two groups as defined above combined to form Ar1, Ar2, for example, phenyl and naphthyl are combined to form Ar1, Ar2.

[0060] In some embodiments, in the L, Ar1 and Ar2, the substitution is independently substituted by at least one of deuterium, halogen, cyano, C1-C6 alkyl, C3-C12 cycloalkyl, C6-C20 aryl or C3-C20 heteroaryl, wherein the number of substitutions is from a single substitution to a maximum number of substitutions. For example, non-limiting examples of substituents include: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, phenanthrenyl or dibenzofuranyl, etc.

[0061] In some embodiments, the R 1w , R 1x , R 1y , R 1z , one of R2-R7 is selected from the structure represented by formula (4) or formula (5).

[0062] In some embodiments, R0 is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, C3-C20 alkylsilyl or C6-C20 arylsilyl.

[0063] In some embodiments, the R0 is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C12 aryl or C3-C12 heteroaryl. Non-limiting examples of R0 include: hydrogen, deuterium, fluorine, methyl, ethyl, phenyl or naphthyl, etc.

[0064] In some embodiments, the R 1w , R 1x , R 1y , R 1z , at least one of R2-R7 is selected from the structures represented by the following formulas (A-10) to (A-15):

[0065]

[0066] Wherein, b represents an integer of 0-9; when b is an integer of 2-9, each R0 is the same or different, and R0 is as defined above.

[0067] In some embodiments, R0 is independently selected from halogen, C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C6-C12 aryl or C3-C12 heteroaryl, and b is selected from an integer of 1 to 3, for example, b can be 1, 2 or 3; or R0 is selected from hydrogen or deuterium, and b represents an integer of 0-9, that is, Formula (A-10) to Formula (A-15) can be unsubstituted, partially deuterated or fully deuterated structures.

[0068] In some embodiments, the remaining R 1w , R 1x , R 1y , R 1z , R2-R7 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, C3-C20 alkylsilyl or C6-C20 arylsilyl; and one of them is selected from the structures shown in formula (A-10) to (A-15).

[0069] In some embodiments, the remaining R 1w , R 1x , R 1y , R 1z , R2-R7 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C20 aryl or C3-C20 heteroaryl; and one of them is selected from the structures shown in formula (A-10) to (A-15).

[0070] In some embodiments, the remaining R 1w , R 1x , R 1y , R 1z , R2-R7 are each independently selected from hydrogen or deuterium, and one of them is selected from the structures represented by formula (A-10) to formula (A-15).

[0071] In some embodiments, formula (1) is selected from one of the following structural formulae, or is one of the following structural formulae in which hydrogen is partially or completely replaced by deuterium or fluorine:

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078] A second aspect of the present invention provides a composition, comprising a first main compound and a second main compound, wherein the first main compound is selected from the above-mentioned aromatic amine compound, and the structure of the second main compound is shown in formula (6):

[0079]

[0080] wherein ring B is selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted phenanthrene ring;

[0081] Y is selected from NR b , CR c R d or oxygen group elements;

[0082] Z1, Z2, Z3 are each independently selected from N or CR e ;

[0083] R b , R c , R d Each is independently selected from C1-C30 alkyl, C1-C30 heteroalkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C3-C30 alkylsilyl or C6-C30 arylsilyl; or R c , R d Connect into a ring;

[0084] R8, R eEach is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphino or C6-C60 arylamine;

[0085] Wherein, b represents an integer of 0-4; when b is an integer of 2-4, each R8 is the same or different;

[0086] L3, L4, and L5 are each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C6-C60 heteroarylene group;

[0087] Ar3 and Ar4 are each independently selected from substituted or unsubstituted C6-C36 aryl or substituted or unsubstituted C2-C36 heteroaryl;

[0088] In the ring B, L3, L4, L5, Ar3 and Ar4, the substitution is independently substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl substituted amine, C1-C6 alkyl substituted or unsubstituted C6-C30 aryl, or C1-C6 alkyl substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions ranges from single substitution to the maximum number of substitutions;

[0089] The heteroatoms in the heteroarylene group, heteroaryl group, heteroalkyl group and heterocycloalkyl group are independently selected from at least one of O, S, N, Se, Si and Ge.

[0090] It can be understood that in formula (6), L3 can be connected to the benzene ring to which ring B or R8 is connected.

[0091] In some embodiments, Y is selected from O, S, Se, NR b or CR c R d , R b , R c , R d are each independently selected from C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl or C6-C20 aryl; or R c , R d Connect into a ring.

[0092] In some embodiments, Y is selected from O, S, Se, NR b or CR c R d , R b , R c , R d Each is independently selected from C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl or C6-C20 aryl; or R c , R d Connect to form a fluorenyl group.

[0093] In some embodiments, Y is selected from O, S, NR b or CR c R d , R b Selected from C6-C20 aryl groups, such as R b Specifically, it may be phenyl, biphenyl or naphthyl; or R c , R d Connect to form a fluorenyl group.

[0094] In some embodiments, Y is selected from O or S.

[0095] In some embodiments, L3, L4, and L5 are each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C6-C30 heteroarylene group.

[0096] In some embodiments, L3, L4, and L5 are each independently selected from a single bond, a substituted or unsubstituted C6-C20 arylene group, or a substituted or unsubstituted C6-C20 heteroarylene group.

[0097] In some embodiments, L3, L4, and L5 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.

[0098] In some embodiments, Ar3 and Ar4 are each independently selected from a substituted or unsubstituted C6-C26 aryl group or a substituted or unsubstituted C2-C26 heteroaryl group.

[0099] In some embodiments, Ar3 and Ar4 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted Ar3, Ar4, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted fluoranthene, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted triphenylene radical, substituted or unsubstituted tetramethyltetrahydronaphthyl, substituted or unsubstituted phenanthrothiazolyl or substituted or unsubstituted phenanthroxazolyl or a combination of at least two of the above. "A combination of at least two of the above" refers to at least two groups as defined above combined to form Ar3, Ar4, such as phenyl and naphthyl combined to form Ar3, Ar4.

[0100] In some embodiments, the R8, R e Each is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, C3-C20 alkylsilyl or C6-C20 arylsilyl.

[0101] In some embodiments, the R8, R e Each is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C12 aryl or C3-C12 heteroaryl.

[0102] In some embodiments, said R8 is selected from hydrogen or deuterium.

[0103] In some embodiments, Z1, Z2, and Z3 are all selected from N, or one of them is selected from CH and the other two are selected from N.

[0104] In some embodiments, in the ring B, L3, L4, L5, Ar3 and Ar4, the substitution is independently substituted by at least one of deuterium, halogen, cyano, C1-C6 alkyl, C3-C12 cycloalkyl, C6-C20 aryl or C3-C20 heteroaryl, wherein the number of substitutions is from a single substitution to the maximum number of substitutions. For example, non-limiting examples of substituents include: deuterium, fluorine, cyano, methyl, ethyl, phenyl, naphthyl, phenanthrenyl, etc.

[0105] In some embodiments, the mass ratio of the first host compound to the second host compound is 8:2-2:8, for example, 7:3-3:7, or 6:4-4:6.

[0106] In some embodiments, formula (6) is selected from one of the following structural formulae, or is one of the following structural formulae in which hydrogen is partially or completely replaced by deuterium or fluorine:

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113] A third aspect of the present invention provides an organic electroluminescent device comprising the above aromatic amine compound or composition.

[0114] In some embodiments, the organic electroluminescent device includes an anode and a cathode, a light-emitting layer is disposed between the anode and the cathode, and the light-emitting layer includes the above-mentioned aromatic amine compound or composition.

[0115] In some embodiments, the aromatic amine compound or composition is used as a red light emitting material of a light emitting layer.

[0116] In some embodiments, the light-emitting layer includes the above-mentioned aromatic amine compound or composition, and a doping material. The aromatic amine compound or composition is used as the main material of the light-emitting layer, and the weight ratio can be 90%-99%, or 95%-99%; the weight ratio of the doping material can be 1%-10%, or 1%-5%. When the light-emitting layer is a red light-emitting layer, the doping material is a red light-emitting material.

[0117] A fourth aspect of the present invention provides an application of the above aromatic amine compound or composition in the semiconductor field.

[0118] In some embodiments, the aromatic amine compound or composition is used to prepare a semiconductor device.

[0119] In some embodiments, the semiconductor device includes an optoelectronic device, such as a lighting fixture, a display (including a car display, a computer display, or a television display, where the display type may be an AMOLED display), or a sensor.

[0120] The aromatic amine compound has the advantages of low sublimation temperature, low driving voltage, high luminous efficiency and long device life, and can be used as the main material of OLED light-emitting devices, especially for red light-emitting devices. The aromatic amine compound can be used to prepare semiconductor devices such as displays, and has application potential in the AMOLED (active matrix organic light-emitting diode) industry.

[0121] definition

[0122] Unless otherwise specified, the scientific and technical terms used herein have the meanings commonly understood by those skilled in the art, but for a better understanding of the present invention, the definitions of some terms are provided below. When the definitions of terms provided by the present invention are inconsistent with the meanings commonly understood by those skilled in the art, the definitions and interpretations of the terms provided by the present invention shall prevail.

[0123] The term "heteroalkyl" refers to an alkyl group defined above in which at least one carbon atom is replaced by a non-carbon atom or a group containing a non-carbon atom, and the non-carbon atom can be selected from at least one of O, S, N, Se, Si or Ge, but does not include a case where a carbon atom as a connection site is replaced by a non-carbon atom (e.g., alkoxy, alkylsilyl). Non-limiting examples of heteroalkyl groups include mercaptomethyl, methoxymethyl, ethoxymethyl, tert-butoxymethyl N, N-dimethylmethane, and further methoxymethyl.

[0124] The term "heterocycloalkyl" refers to a cycloalkyl group in which at least one carbon atom is replaced by a non-carbon atom, and the non-carbon atom can be selected from at least one of O, S, N, Se, Si or Ge. The number of carbon atoms in the heterocycloalkyl group can be 3 to 40, 3 to 30, 3 to 20, 3 to 12, 3 to 10, or 3 to 6. Non-limiting examples of heterocycloalkyl groups include: butylene oxide, cyclopentyl oxide and hexyl oxide, and further cyclopentyl oxide.

[0125] The term "alkoxy" refers to a group having -O-alkyl, wherein the oxygen atom is used as the attachment site, and the alkyl group is as defined above. Non-limiting examples of alkoxy include: methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy. Each group includes various isomers, such as butoxy includes isomers such as n-butoxy, isobutoxy, tert-butoxy, and sec-butoxy.

[0126] The term "aryl" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which can be a monocyclic aromatic group or a polycyclic aromatic group. In a polycyclic aromatic group, at least one ring is an aromatic ring system. In a polycyclic aromatic group, multiple rings can be connected to each other via a single bond or can be fused to each other. The number of carbon atoms of the aryl group can be 6 to 60, 6 to 40, 6 to 30, 6 to 20, 6 to 12 or 6 to 10. For example, when a polycyclic aromatic group contains a fused ring structure, it can be specifically formed by condensing a C3-C30 aliphatic ring (a saturated or unsaturated aliphatic ring containing 3 to 30 ring skeleton carbon atoms) and a C3-C30 aromatic ring (an aromatic ring containing 3 to 30 ring skeleton carbon atoms), more specifically, by condensing a C3-C20 aliphatic ring and a C6-C30 aromatic ring. Specific examples of the aryl group include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, anthracenyl, phenanthrenyl, naphthyl, pyrenyl, The following examples include 1,2-dimethyl-1,2-diphenyl-2,2-diphenyl-3,2-diphenyl-4,2-diphenyl-5,2-diphenyl-6,6-diphenyl-7,8-diphenyl-8,8-diphenyl-9,8-diphenyl ...8,8-diphenyl-9,8-diphenyl-8,8-diphenyl-9,8-diphenyl-8,8-diphenyl-9,8-diphenyl-8,8-diphenyl-9,8-di

[0127] The term "heteroaryl" refers to a monovalent group in which at least one carbon atom based on an aromatic group is replaced by a non-carbon atom, wherein the non-carbon atom can be selected from a heterocyclic aromatic system of O, S, N, Se, Si or Ge, but does not include the case where the aromatic group is connected to the main structure through a non-carbon atom group (for example, an aryloxy group, an arylsilyl group, an arylamine group). Specific examples of heteroaryl groups include dibenzofuranyl, carbazolyl, pyridyl, pyrimidinyl, benzoxazolyl, benzimidazolyl, benzotriazolyl, phenanthrothiazolyl, phenanthroxazolyl, pyrrolyl, pyrrolopyrrolyl, furopyrrolyl, thienopyrrolyl, pyrazolyl, pyrazinyl, triazinyl, pyridazinyl, phenazinyl, phenothiazinyl, phenoxazinyl, indolyl, isoindolyl, imidazolyl, triazolyl, tetrazolyl, furanyl, benzofuranyl, isobenzofuranyl, furofuranyl, azadibenzofuranyl, thienofuranyl, diazadiphenyl 1,2-d]furanyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, quinazolinonyl, azacarbazolyl, diazacarbazolyl, phenanthridinyl, primary pyridinyl, acridinyl, dihydroacridinyl, phenanthrolinyl, oxazolinyl, oxazolyl, oxadiazolyl, benzisoxazolyl, thiazolyl, benzothiazolyl, benzisothiazolyl, pyrroloimidazolyl, furazanyl, thienyl, benzothienyl, dibenzothienyl, azadibenzothienyl, diazadibenzothienyl, thienothiphenyl or o-naphthyridinyl.

[0128] It is understood that the terms "arylene" and "heteroarylene" correspond to divalent groups having the same structure as aryl and heteroaryl, respectively.

[0129] In the term "alkylsilyl" or "arylsilyl", the number of alkyl or aryl groups may be 1 to 3. "Alkylboryl" includes monoalkylboryl and dialkylboryl, "arylboryl" includes monoarylboryl and diarylboryl, and "arylphosphino" includes monoarylphosphino and diarylphosphino. In the terms alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, etc., the carbon number defined refers to the total carbon number of the group.

[0130] The "carbon number ab" in the expression "a substituted or unsubstituted X group having ab carbon numbers" means the carbon number when the X group is unsubstituted, and does not include the carbon number of a substituent when the X group is substituted.

[0131] The "substituted" in "substituted or unsubstituted" means that one or more hydrogen atoms are replaced by other atoms or functional groups (i.e., substituents), and unless otherwise limited by the definition, it also includes that one or more hydrogen atoms are replaced by a group formed by connecting two or more of the above-mentioned substituents.

[0132] The following embodiments are only for facilitating the understanding of the technical invention and should not be regarded as specific limitations of the present invention.

[0133] The raw materials and solvents involved in the synthesis of the compounds were purchased from suppliers familiar to those skilled in the art such as Alfa and Acros. The raw materials, reagents or devices used, unless otherwise specified, can be obtained from conventional commercial channels or by existing known methods.

[0134] Unless otherwise specified, all solution ratios are by volume.

[0135] Synthesis of Compound A3

[0136]

[0137] Synthesis of Compound A3-2

[0138] Compound A3-1 (30.00 g, 134.49 mmol) and DCM (450 ml) were added into a 1000 ml three-necked round-bottom flask. The vacuum was replaced with nitrogen three times. When the temperature in the system dropped to 5°C, N-iodosuccinimide (30.26 g, 134.49 mmol) was added in batches over 5 minutes. The temperature was maintained for 1 hour. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:20 as the developing solvent). The compound A3-1 was completely consumed.

[0139] Saturated aqueous sodium bisulfite solution (100 ml) was added to quench the reaction, and the liquid was separated directly. The sample was mixed with silica gel and dry-loaded onto a column for purification by silica gel column chromatography (300 g, 200-300 mesh silica gel, ethyl acetate:n-hexane = 1:20 as eluent). After elution, the mixture was concentrated under reduced pressure at 70 ° C for 1 hour to obtain a white solid as compound A3-2 (37.48 g, purity: 99.01%, yield: 79.86%), mass spectrum: 349.60 (M+H).

[0140] Synthesis of Compound A3-4

[0141] A3-2 (25.00 g, 71.64 mmol), A3-3 (12.49 g, 71.64 mmol), tetrakis(triphenylphosphine)palladium (1.65 g, 1.43 mmol), potassium carbonate (14.85 g, 107.46 mmol), tetrahydrofuran (375 ml), and deionized water (125 ml) were added to a 1000 ml three-necked round-bottom flask, and the vacuum nitrogen was replaced three times. Then the system was heated to 60 ° C for 2 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:10 as the developing solvent). Compound A3-2 was completely consumed.

[0142] The temperature was lowered to 60°C, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (700 ml) was added, and the mixture was washed three times with deionized water (300 ml*3). The mixture was separated, and the sample was mixed with silica gel and dry-loaded onto a column. Purification was performed by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate:n-hexane = 1:20 as eluent). After elution, the mixture was concentrated under reduced pressure at 70°C for 2 hours to obtain a white solid A3-4 (18.97 g, purity: 99.21%, yield: 75.32%), with a mass spectrum of 351.22 (M+H).

[0143] Synthesis of Compound A3-5

[0144] Compound A3-4 (18.00 g, 51.19 mmol), cesium carbonate (25.02 g, 79.79 mmol) and N,N-dimethylformamide (300 ml) were added to a 1000 ml three-necked round-bottom flask, and the vacuum nitrogen was replaced three times. Then the system was heated to 100 ° C. and reacted for 2 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). Compound A3-4 was completely consumed.

[0145] The temperature was lowered to 70°C, the solvent was removed by vacuum concentration, ethyl acetate (700ml) was added for extraction, the liquid was separated, and vacuum concentration was performed at 70°C for 1 hour to obtain 13g of a light yellow solid. Tetrahydrofuran (300ml) was added, and then the system was heated to 70°C for dissolution and clarification, and 30g (300-400 mesh) of silica gel was spread for filtration, and the surface of the silica gel was rinsed with tetrahydrofuran (50ml), and the combined filtrate was concentrated to obtain 17g. Tetrahydrofuran (200ml) and methanol (100ml) were used for crystallization twice, and suction filtration was performed. The filter cake was vacuum dried at 80°C for 3 hours to obtain a white solid compound A3-5 (14.51g, purity: 99.61%, yield: 85.45%), mass spectrum: 331.04 (M+H).

[0146] Synthesis of Compound A3-7

[0147] Compound A3-5 (14.00 g, 42.22 mmol), compound A3-6 (7.26 g, 42.22 mmol), bis(4-dimethylaminophenyldi-tert-butylphosphine)palladium dichloride (0.30 g, 0.42 mmol), potassium carbonate (8.75 g, 63.33 mmol), toluene (210 ml), ethanol (70 ml), and deionized water (70 ml) were added to a 500 ml three-necked round-bottom flask, and the vacuum nitrogen was replaced three times. Then the system was heated to 65 ° C for 2 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:10 as the developing solvent). The raw material compound A3-5 was consumed.

[0148] Cool to room temperature, add methanol (200 ml), stir at room temperature for 1 hour, and a large amount of solid precipitates. Add toluene (350 ml), heat the system to 100°C and dissolve, cool to room temperature, filter once with 200-300 mesh silica gel (20 g), add methanol (350 ml) to the filtrate at room temperature, stir at room temperature for 1 hour, filter to obtain a white solid wet product, dry at 100°C for 1 hour to obtain a light yellow solid; crystallize twice with toluene and methanol, filter, and dry the filter cake at 100°C in vacuum for 5 hours to obtain a white solid compound A3-7 (12.62 g, purity: 99.53%, yield: 78.88%), mass spectrum: 379.08 (M+H).

[0149] Synthesis of Compound A3

[0150] Compound A3-7 (10.00 g, 26.04 mmol), compound A3-8 (6.80 g, 27.72 mmol), tris(dibenzylideneacetone)dipalladium (0.48 g, 0.52 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.50 g, 1.04 mmol), sodium tert-butoxide (3.75 g, 39.06 mmol), and toluene (150 ml) were added to a 500 ml three-necked round-bottom flask, and the vacuum was replaced with nitrogen three times. Then, the system was heated to 105 ° C for 2 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). Compound A3-7 was completely consumed.

[0151] Cool down to 60℃, add methanol (150ml), naturally cool to room temperature and stir for 30 minutes to precipitate a large amount of solid, filter by suction to obtain 20g solid, add toluene (300ml), then heat the system to 100℃ to dissolve and clarify, pave 30g (300-400 mesh) silica gel for filtration, rinse the silica gel surface with toluene (50ml), combine the filtrate and concentrate to obtain 17g. Crystallize twice with toluene (170ml) and methanol (70ml), filter by suction, and dry the filter cake at 90℃ in vacuum for 3 hours to obtain a light yellow solid compound A3 (13.72g, purity: 99.94%, yield: 88.41%). 13.72g of crude compound A3 was purified by sublimation to obtain sublimation pure A3 (11.26g, purity: 99.95%, yield: 82.06%), mass spectrum: 588.22 (M+H).

[0152] 1 H NMR (400MHz, CDCl3) δ8.41(t,J=2.2Hz,1H),8.18(d,J=8.2Hz,1H),8.08(t,J =2.1Hz,1H),8.06–7.99(m,2H),7.93(d,J=8.0Hz,1H),7.90–7.80(m,3H),7. 78–7.76(m,1H),7.61–7.54(m,2H),7.54–7.47(m,4H),7.46–7.37(m,4H),7. 35–7.24(m,4H),7.15(d,J=1.4Hz,1H),7.14–7.06(m,2H),7.03–6.97(m,2H).

[0153] Synthesis of Compound A16

[0154]

[0155] Referring to the synthesis and purification method of compound A3, only the corresponding raw materials need to be changed to obtain a light yellow solid as the target compound A16 (16.74 g, purity: 99.95%, yield: 78.65%). 16.74 g of crude compound A16 was purified by sublimation to obtain sublimation pure A16 (13.10 g, purity: 99.95%, yield: 78.26%), mass spectrum: 678.32 (M+H).

[0156] 1H NMR (400MHz, CDCl3) δ8.41(t,J=2.2Hz,1H),8.18(d,J=8.3Hz,1H),8.08(t,J=2.2Hz,1H),8.07–7.99(m,3H),7.93(d,J=8.1Hz,1H),7 .90–7.75(m,4H),7.67–7.57(m,4H),7.57–7.47(m,3H),7.47–7.38(m,3H),7.35–7.24(m,5H),7.17–7.06(m,3H),6.97–6.91(m,2H).

[0157] Synthesis of compound A21

[0158]

[0159] Synthesis of Compound A21-2

[0160] Referring to the synthesis and purification method of compound A3-2, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A21-2 (36.07 g, purity: 99.06%, yield: 80.01%), mass spectrum: 349.60 (M+H).

[0161] Synthesis of Compound A21-3

[0162] Referring to the synthesis and purification method of compound A3-4, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A21-3 (25.32 g, purity: 99.31%, yield: 76.23%), mass spectrum: 351.22 (M+H).

[0163] Synthesis of Compound A21-4

[0164] Referring to the synthesis and purification method of compound A3-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A21-4 (20.63 g, purity: 99.72%, yield: 84.23%), mass spectrum: 331.04 (M+H).

[0165] Synthesis of Compound A21-6

[0166] Referring to the synthesis and purification method of compound A3-7, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A21-6 (18.32 g, purity: 99.49%, yield: 78.79%), mass spectrum: 429.10 (M+H).

[0167] Synthesis of compound A21

[0168] Referring to the synthesis and purification method of compound A3, only the corresponding raw materials need to be changed to obtain the target compound A21 (15.12 g, purity: 99.96%, yield: 77.06%) as a light yellow solid. 15.12 g of crude compound A21 was purified by sublimation to obtain sublimation pure A21 (12.99 g, purity: 99.96%, yield: 85.91%), mass spectrum: 638.32 (M+H).

[0169] 1 H NMR(400MHz, CDCl3)δ8.50–8.43(m,1H),8.20(d,J=2.3Hz,1H),8.08–8.02(m,2H), 8.02–7.92(m,4H),7.92–7.84(m,2H),7.79–7.77(m,2H),7.61–7.55(m,2H),7.55–

[0170] 7.47(m,4H),7.45–7.37(m,4H),7.34–7.23(m,4H),7.17–7.07(m,3H),7.04–6.96(m,2H).

[0171] Synthesis of compound A30

[0172]

[0173] Synthesis of Compound A30-2

[0174] Referring to the synthesis and purification method of compound A3-4, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A30-2 (27.63 g, purity: 99.42%, yield: 77.45%), mass spectrum: 351.22 (M+H).

[0175] Synthesis of Compound A30-3

[0176] Referring to the synthesis and purification method of compound A3-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A30-3 (24.21 g, purity: 99.46%, yield: 85.55%), mass spectrum: 331.04 (M+H).

[0177] Synthesis of Compound A30-4

[0178] Referring to the synthesis and purification method of compound A3-7, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A30-4 (20.53 g, purity: 99.40%, yield: 79.00%), mass spectrum: 379.08 (M+H).

[0179] Synthesis of compound A30

[0180] Referring to the synthesis and purification method of compound A3, only the corresponding raw materials need to be changed to obtain the target compound A30 (14.01 g, purity: 99.96%, yield: 79.33%) as a light yellow solid. 14.01 g of crude compound A30 was purified by sublimation to obtain sublimation pure A30 (11.55 g, purity: 99.96%, yield: 82.45%), mass spectrum: 588.22 (M+H).

[0181] 1 H NMR (400MHz, CDCl3) δ8.64(d,J=8.6Hz,1H),8.34(s,1H),8.26(d,J=8.5Hz,1H),8.21(s,1H),8.12 –8.06(m,1H),8.05–7.80(m,5H),7.75(d,J=8.9Hz,1H),7.71–7.14(m,17H),7.10(t,J=7.3Hz,1H).

[0182] Synthesis of Compound A39

[0183]

[0184] Synthesis of compound A39-3

[0185] Referring to the synthesis and purification method of compound A3-7, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A39-3 (19.56 g, purity: 99.89%, yield: 75.63%), mass spectrum: 363.14 (M+H).

[0186] Synthesis of Compound A39-4

[0187] Referring to the synthesis and purification method of compound A3-4, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A39-4 (18.06 g, purity: 99.50%, yield: 78.69%), mass spectrum: 351.22 (M+H).

[0188] Synthesis of Compound A39-5

[0189] Referring to the synthesis and purification method of compound A3-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A39-5 (16.33 g, purity: 99.58%, yield: 86.07%), mass spectrum: 331.04 (M+H).

[0190] Synthesis of Compound A39-6

[0191] Referring to the synthesis and purification method of compound A3-7, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A39-6 (18.00 g, purity: 99.63%, yield: 79.06%), mass spectrum: 379.08 (M+H).

[0192] Synthesis of Compound A39

[0193] Referring to the synthesis and purification method of compound A3, only the corresponding raw materials need to be changed to obtain a light yellow solid as the target compound A39 (14.02 g, purity: 99.94%, yield: 75.33%). 14.02 grams of crude compound A39 was purified by sublimation to obtain sublimation pure A39 (12.15 g, purity: 99.94%, yield: 86.66%), mass spectrum: 705.26 (M+H).

[0194] 1 H NMR(400MHz, CDCl3)δ8.20(d,J=2.3Hz,1H),8.10–8.03(m,2H),7.99–7.77(m,11H) ,7.63–7.57(m,2H),7.55–7.46(m,3H),7.46–7.41(m,2H),7.37–7.35(m,1H),7.34–

[0195] 7.24(m,3H),7.17–7.06(m,5H),6.94–6.88(m,2H).

[0196] Synthesis of Compound A63

[0197]

[0198] Synthesis of Compound A63-2

[0199] Referring to the synthesis and purification method of compound A3-4, it is only necessary to change the corresponding raw materials and reaction temperature to obtain a white solid as the target compound A63-2 (30.33 g, purity: 99.63%, yield: 80.33%), mass spectrum: 334.06 (M+H).

[0200] Synthesis of Compound A63-4

[0201] Compound A63-2 (28.00 g, 83.89 mmol), compound A63-3 (43.14 g, 125.83 mmol) and tetrahydrofuran (450 ml) were added into a 1000 ml three-necked round-bottom flask, and the vacuum nitrogen was replaced three times. Then the system was cooled to 5°C, and sodium methoxide (9.06 g, 167.78 mmol) was added at one time. The reaction was maintained at 5°C for 1 hour, and the reaction was monitored by TLC (ethyl acetate: n-hexane = 1:10 as the developing solvent). The raw material compound A63-2 was completely consumed.

[0202] Deionized water (500 ml) was added, the solvent was removed by concentration under reduced pressure, ethyl acetate (700 ml) was added for extraction, the layers were separated, and the mixture was concentrated under reduced pressure at 70° C. for 1 hour to obtain a white solid compound A63-4 (28.84 g, yield: 95.00%), mass spectrum: 362.09 (M+H). The obtained compound was used directly in the next step without purification.

[0203] Synthesis of Compound A63-5

[0204] Compound A63-4 (26.00 g, 71.86 mmol) and toluene (260 ml) were added into a 1000 ml three-necked round-bottom flask, and the vacuum was replaced with nitrogen three times. Then the system was cooled to 5°C, and methanesulfonic acid (13.81 g, 143.72 mmol) was slowly added dropwise. The addition was completed within 3 minutes, and the reaction was maintained at 5°C for 1 hour. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). Compound A63-4 was completely consumed.

[0205] Methanol (260 ml) was added thereto, and a large amount of white solid precipitated. 23 g of solid was obtained by filtration. The solid was crystallized once with toluene (230 ml) and methanol (230 ml). The filter cake was dried under vacuum at 80°C for 1 hour to obtain a white solid, which was compound A63-4 (14.22 g, purity: 99.83%, yield: 60.00%), mass spectrum: 330.06 (M+H).

[0206] Synthesis of Compound A63-7

[0207] Referring to the synthesis and purification method of compound A3, it is only necessary to change the corresponding raw materials and reaction temperature to obtain a white solid as the target compound A63-7 (22.62 g, purity: 99.87%, yield: 78.25%), mass spectrum: 387.12 (M+H).

[0208] Synthesis of Compound A63-8

[0209] Referring to the synthesis and purification method of compound A3, it is only necessary to change the corresponding raw materials and reaction temperature to obtain a white solid as the target compound A63-8 (20.14 g, purity: 99.85%, yield: 77.64%), mass spectrum: 637.14 (M+H).

[0210] Synthesis of Compound A63

[0211] Referring to the synthesis and purification method of compound A3, only the corresponding raw materials need to be changed to obtain a light yellow solid as the target compound A63 (15.74 g, purity: 99.94%, yield: 76.03%). 15.74 grams of crude compound A63 was purified by sublimation to obtain sublimation pure A63 (13.16 g, purity: 99.94%, yield: 83.60%), mass spectrum: 729.24 (M+H).

[0212] 1 H NMR (400MHz, CDCl3) δ8.25(d,J=2.0Hz,1H),8.17(d,J=2.2Hz,1H),8.12(t,J=7.4Hz,2H),8.08(t,J=2.1Hz,1H),8.06–8.00(m,3H),8.00–7.88 (m,6H),7.88–7.81(m,3H),7.71-7.58(m,1H),7.55–7.47(m,3H),7.47 –7.38(m,3H),7.34–7.25(m,3H),7.17–7.05(m,3H),6.89–6.86(m,2H).

[0213] Synthesis of Compound A77

[0214]

[0215] Synthesis of Compound A77-2

[0216] Compound A3-5 (35.35 g, 106.56 mmol), compound A77-1 (32.47 g, 127.87 mmol), 1,1-bis(diphenylphosphine)diphosphine iron palladium dichloride (1.56 g, 2.13 mmol), potassium acetate (15.69 g, 159.84 mmol), and 1,4-dioxane (450 ml) were added to a 1000 ml three-necked round-bottom flask, and the vacuum nitrogen was replaced three times. Then the system was heated to 100 ° C and reacted for 2 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:10 as the developing solvent). Compound A3-5 was completely consumed.

[0217] The temperature was lowered to 60°C, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (700 ml) was added, and the mixture was washed three times with deionized water (300 ml*3). The mixture was separated, and the sample was mixed with silica gel and dry-loaded onto a column. Purification was performed by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate:n-hexane = 1:15 as eluent). After elution, the mixture was concentrated under reduced pressure at 70°C for 1 hour to obtain a white solid, which was compound A77-2 (31.82 g, purity: 98.01%, yield: 78.88%), with a mass spectrum of 379.12 (M+H).

[0218] Synthesis of Compound A77-4

[0219] Referring to the synthesis and purification method of compound A3-7, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A77-4 (19.08 g, purity: 99.58%, yield: 77.06%), mass spectrum: 380.04 (M+H).

[0220] Synthesis of Compound A77-5

[0221] Referring to the synthesis and purification method of compound A77-2, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A77-5 (24.63 g, purity: 99.00%, yield: 76.32%), mass spectrum: 472.04 (M+H).

[0222] Synthesis of Compound A77-7

[0223] Referring to the synthesis and purification method of compound A3-7, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A77-7 (18.42 g, purity: 99.46%, yield: 79.06%), mass spectrum: 456.12 (M+H).

[0224] Synthesis of Compound A77

[0225] Referring to the synthesis and purification method of compound A3, only the corresponding raw materials need to be changed to obtain the target compound A77 (16.25 g, purity: 99.95%, yield: 78.06%) as a light yellow solid. 16.25 g of crude compound A77 was purified by sublimation to obtain sublimation pure A77 (14.00 g, purity: 99.95%, yield: 86.15%), mass spectrum: 665.26 (M+H).

[0226] 1H NMR(400MHz, CDCl3)δ8.34(t,J=2.1Hz,1H),8.17–8.07(m,2H),8.07–7.98(m,3H), 7.98–7.89(m,2H),7.83–7.73(m,2H),7.63–7.62(m,1H),7.61–7.54(m,2H),7.54–

[0227] 7.46(m,4H),7.46–7.38(m,4H),7.38–7.31(m,3H),7.31–7.23(m,2H),7.17–7.05(m,4H),7.05–6.94(m,2H).

[0228] Synthesis of compound A101

[0229]

[0230] Synthesis of Compound A101-2

[0231] Referring to the synthesis and purification method of compound A3-7, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A101-2 (15.63 g, purity: 99.40%, yield: 76.52%), mass spectrum: 379.06 (M+H).

[0232] Synthesis of compound A101

[0233] Referring to the synthesis and purification method of compound A3, only the corresponding raw materials need to be changed to obtain the target compound A101 (12.03 g, purity: 99.95%, yield: 77.85%) as a light yellow solid. 12.03 g of crude compound A101 was purified by sublimation to obtain sublimation pure A101 (10.04 g, purity: 99.95%, yield: 83.45%), mass spectrum: 678.24 (M+H).

[0234] 1 H NMR (400MHz, CDCl3) δ8.47(d,J=0.8Hz,1H),8.27(t,J=2.2Hz,1H),8.04–7.96(m,1H ),7.96–7.81(m,7H),7.78–7.75(m,2H),7.66–7.54(m,4H),7.54–7.45(m,3H),7.45–

[0235] 7.37(m,6H),7.37–7.28(m,2H),7.11–7.09(m,1H),7.07(d,J=2.0Hz,1H),7.05–6.89(m,2H).

[0236] Synthesis of compound A145

[0237]

[0238] Synthesis of Compound A145-2

[0239] Referring to the synthesis and purification method of compound A3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A145-2 (14.85 g, purity: 99.65%, yield: 75.84%), mass spectrum: 496.14 (M+H).

[0240] Synthesis of Compound A145-3

[0241] Referring to the synthesis and purification method of compound A77-2, it is only necessary to change the corresponding raw materials to obtain the white solid as the target compound A145-3 (17.56 g, purity: 99.03%, yield: 77.63%), mass spectrum: 588.20 (M+H).

[0242] Synthesis of compound A145

[0243] Referring to the synthesis and purification method of compound A3-7, only the corresponding raw materials need to be changed to obtain the target compound A145 (14.33 g, purity: 99.94%, yield: 78.11%) as a light yellow solid. 14.33 g of crude compound A145 was purified by sublimation to obtain sublimation pure A145 (12.05 g, purity: 99.94%, yield: 84.08%), mass spectrum: 640.22 (M+H).

[0244] 1 H NMR (400MHz, CDCl3) δ8.84–8.82(m,1H),8.45(s,1H),8.33(d,J=8.0Hz,1H),8 .25(d,J=2.4Hz,1H),8.15–8.05(m,4H),7.99(d,J=2.0Hz,1H),7.80–7.71(m,2 H),7.61–7.54(m,2H),7.54–7.48(m,3H),7.45–7.38(m,4H),7.38–7.34(m,1H ),7.32–7.24(m,2H),7.19–7.14(m,2H),7.14–7.06(m,1H),7.00–6.91(m,3H).

[0245] Synthesis of compound A150

[0246]

[0247] Synthesis of Compound A150-2

[0248] Referring to the synthesis and purification method of compound A3-7, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A150-2 (13.05 g, purity: 99.54%, yield: 85.33%), mass spectrum: 386.16 (M+H).

[0249] Synthesis of compound A150

[0250] Referring to the synthesis and purification method of compound A3, only the corresponding raw materials need to be changed to obtain the target compound A150 (11.06 g, purity: 99.95%, yield: 79.74%) as a light yellow solid. 11.06 g of crude compound A150 was purified by sublimation to obtain sublimation pure A150 (9.72 g, purity: 99.94%, yield: 87.88%), mass spectrum: 560.32 (M+H).

[0251] 1 H NMR (400MHz, CDCl3) δ8.21–8.13(m,2H),7.99–7.94(m,1H),7.90(d,J=7.5Hz,1H),7.78–7.75(m,1H) ,7.61–7.50(m,4H),7.45–7.41(m,2H),7.41–7.35(m,3H),7.31(d,J=7.3Hz,1H),7.08–7.01(m,2H).

[0252] Synthesis of Compound A163

[0253]

[0254] Synthesis of Compound A163-2

[0255] Referring to the synthesis and purification method of compound A3-7, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A163-2 (15.63 g, purity: 99.74%, yield: 87.52%), mass spectrum: 454.22 (M+H).

[0256] Synthesis of Compound A163

[0257] Referring to the synthesis and purification method of compound A3, only the corresponding raw materials need to be changed to obtain the target compound A163 (15.08 g, purity: 99.96%, yield: 75.48%) as a light yellow solid. 15.08 g of crude compound A163 was purified by sublimation to obtain sublimation pure A163 (12.06 g, purity: 99.96%, yield: 79.978%), mass spectrum: 752.36 (M+H).

[0258] 1 H NMR (400MHz, CDCl3) δ8.21–8.20(m,1H),8.17–8.11(m,2H),8.11–8.05(m,2H),8.01–7.95(m,2H),7.93–7.92(m,1H),7.90–7. 76(m,6H),7.58–7.46(m,4H),7.42–7.40(m,1H),7.38–7.36(m,1H),7.34–7.23(m,8H),7.23–7.13(m,8H),7.12–7.08(m,1H).

[0259] Example:

[0260] The aromatic amine compounds of Examples 1 to 8 correspond to the synthesized compounds A3, A16, A21, A30, A39, A63, A77 and A101, respectively.

[0261] Embodiments 9 to 31 provide a composition consisting of a first main compound and a second main compound, wherein the first main compound is selected from the synthetic compounds A3, A16, A21, A30, A39, A63, A77, A101, A145, A150, A163, and the second main compound is selected from the synthetic compounds B25, B54, B71, B80, B104, B128, and the mass ratio of the first main compound to the second main compound is 1:1.

[0262] The structural formulas of the compounds involved in each embodiment are as follows:

[0263]

[0264] Application example: Fabrication of organic electroluminescent devices

[0265] like Figure 2 As shown, it is a schematic diagram of the structure of an organic electroluminescent device, including a glass substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4, a second hole transport layer 5, a light-emitting layer 6, an electron transport layer 7, an electron injection layer 8, and a cathode 9 which are stacked in sequence.

[0266] A 50mm*50mm*1.0mm glass substrate with an ITO (indium tin oxide, 100nm) transparent electrode was ultrasonically cleaned in ethanol for 10 minutes, dried at 150°C, and treated with N2 Plasma (plasma gas) for 30 minutes. The washed glass substrate was mounted on a substrate holder of a vacuum evaporation device, and the compound NDP-9 and the compound HTM1 were evaporated at a weight ratio of 97:3 to form a hole injection layer with a thickness of 10nm, followed by evaporation of a layer of HTM1 to form a film with a thickness of 60nm as HTL1 (first hole transport layer), and then a layer of HTM2 was evaporated on HTL1 to form a film with a thickness of 10nm as HTL2 (second hole transport layer).

[0267] Then, a light-emitting layer with a thickness of 40 nm was evaporated on HTL2, and the light-emitting layer was composed of a host material and a red light doping material in a mass ratio of 97:3. The types of host materials of each embodiment and comparative example are shown in Table 1 and Table 2 below. In the dual host material in Table 2, the mass ratio of the first host compound to the second host compound is 1:1.

[0268] A 35 nm thick electron transport layer was evaporated on the light-emitting layer, where the electron transport layer consisted of ETL and LiQ in a weight ratio of 50:50. Then, 1 nm thick LiQ was evaporated on the electron transport layer as an electron injection layer. Then, Mg / Ag (Mg / Ag mass ratio of 1:9) was co-evaporated as a cathode (thickness 100 nm) to obtain an organic electroluminescent device.

[0269] The structural formulas of NDP-9, HTM1, HTM2, ETL, red light doping material, LiQ and comparative compounds 1-4 are as follows:

[0270]

[0271] evaluate:

[0272] The above organic electroluminescent device was tested for device performance. A constant current power supply (Keithley2400) was used to flow a fixed current density through the light-emitting element. The luminescence spectrum was tested using a spectroradiometer (CS2000). At the same time, the current was 10 mA / cm 2 The IVL (current-voltage-luminance) performance of the device was measured at 50 mA / cm 2 The life of LT95 devices was tested under the following conditions. The results are shown in Tables 1 and 2 below.

[0273] Table 1

[0274]

[0275] Table 2

[0276]

[0277]

[0278] It can be seen from Table 1 and Table 2 that the aromatic amine compound of the embodiment of the present invention, as a single-host red light material, exhibits lower driving voltage, higher current efficiency and longer device life than the comparative compound. In addition, when the compound is used with the second host compound as a dual-host material, it can effectively balance the transmission rate of holes and electrons, broaden the exciton recombination area in the light-emitting layer, thereby significantly improving the efficiency and service life of the device, and reducing the driving voltage, and the overall performance is far better than the comparative compounds 1-4.

[0279] Sublimation temperature comparison: Sublimation temperature is defined as: at 10 -7 The vacuum degree is 10000 Torr, and the temperature corresponding to the sublimation rate is 1 angstrom per second. The test results of some compounds of the examples of the present invention and comparative compounds 1-4 are shown in Table 3.

[0280] Table 3

[0281] Material Sublimation temperature / ℃ A3 254 A16 259 A30 255 A39 261 Comparative Compound 1 272 Comparative Compound 2 266 Comparative Compound 3 269 Comparative Compound 4 272

[0282] It can be seen from Table 3 that the aromatic amine compounds of the embodiments of the present invention have lower sublimation temperatures than the comparative compounds 1-4, which is conducive to industrial application.

[0283] Therefore, the aromatic amine compound of the present invention has the advantages of low sublimation temperature, low driving voltage, high luminous efficiency and long device life, and is suitable for use as a main material of an OLED light-emitting device, and has application potential in the AMOLED industry.

[0284] In addition, this compound also has the advantages of high optical and electrical stability, and has a low melting point. As a molten material, it is beneficial to improve the evaporation stability.

[0285] In addition, since it is impossible to enumerate all the compounds of the present invention, the above Tables 1-3 only list some of the aromatic amine compounds or device properties of the present invention. However, within the scope of the present invention, especially the compounds with specific structural formulas given in the present invention, they all have the advantages of high optical and electrical stability, low sublimation temperature, low driving voltage, high luminous efficiency, and long device life similar to A3.

Claims

1. An aromatic amine compound, characterized in that The structure of the aromatic amine compound is shown in formula (1): Wherein, ring A is selected from the following formula (2) or formula (3): Wherein, * represents the site of fusion with the five-membered ring containing X in formula (1); R 1w , R 1x , R 1y , R 1z , at least one of R2-R7 is selected from the following formula (4) or formula (5): * represents the connection site with the naphthalene ring in formula (2) or (3); X1-X 10 are independently selected from CR0 or N; And, -LN(Ar1)(Ar2) replaces R2-R6, R 1w , R 1y , R 1z Any one of; The rest R 1w , R 1x , R 1y , R 1z , R2-R7 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphino or C6-C60 arylamine; each R0 is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphino or C6-C60 arylamine; X is selected from O, S, Se or NR a ; R a Selected from C1-C30 alkyl, C1-C30 heteroalkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 alkylsilyl or C6-C30 arylsilyl; Wherein, a represents an integer of 0-4; when a is an integer of 2-4, each R1 is the same or different; L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C6-C60 heteroarylene group; Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C36 aryl group or a substituted or unsubstituted C2-C36 heteroaryl group; In said L, Ar1 and Ar2, said substitution is independently substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl substituted amine, C1-C6 hydrocarbon substituted or unsubstituted C6-C30 aryl or C1-C6 hydrocarbon substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions is from a single substitution to the maximum number of substitutions; The heteroatoms in the heteroarylene group, heteroaryl group, heteroalkyl group or heterocycloalkyl group are independently selected from at least one of O, S, N, Se, Si or Ge.

2. The aromatic amine compound according to claim 1, characterized in that The formula (1) is selected from one of the structures shown in the following formulas (A-1) to (A-9):

3. The aromatic amine compound according to claim 1 or 2, characterized in that The X is selected from O, S or NR a , R a selected from C6-C20 aryl; and / or, said L is selected from a single bond, a substituted or unsubstituted C6-C20 arylene or a substituted or unsubstituted C6-C20 heteroarylene; and / or, said Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C26 aryl or a substituted or unsubstituted C2-C26 heteroaryl; and / or, in said L, Ar1 and Ar2, said substitution is independently substituted by at least one of deuterium, halogen, cyano, C1-C6 alkyl, C3-C12 cycloalkyl, C6-C20 aryl or C3-C20 heteroaryl, wherein the number of substitutions is from a single substitution to a maximum number of substitutions; and / or, said R 1w , R 1x , R 1y , R 1z , one of R2-R7 is selected from the structure represented by formula (4) or formula (5).

4. The aromatic amine compound according to claim 1 or 2, characterized in that The R 1w , R 1x , R 1y , R 1z , at least one of R2-R7 is selected from the structures represented by the following formulas (A-10) to (A-15): Wherein, b represents an integer from 0 to 9; when b is an integer from 2 to 9, each R0 is the same or different; And / or, each R0 is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, C3-C20 alkylsilyl, C6-C20 arylsilyl.

5. The aromatic amine compound according to claim 4, characterized in that The R 1w , R 1x , R 1y , R 1z , R2-R7 is selected from the structures shown in formula (A-10) to formula (A-15), -LN(Ar1)(Ar2) replaces R2-R6, R 1w , R 1y , R 1z Any one of the other R 1w , R 1x , R 1y , R 1z , R2-R7 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, C3-C20 alkylsilyl, C6-C20 arylsilyl.

6. The aromatic amine compound according to claim 1 or 2, characterized in that The Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted triphenylene radical, substituted or unsubstituted tetramethyltetrahydronaphthyl, substituted or unsubstituted phenanthrothiazolyl, or substituted or unsubstituted phenanthroxazolyl, or a combination of at least two of the foregoing; And / or, the L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group or a substituted or unsubstituted naphthylene group.

7. The aromatic amine compound according to claim 1 or 2, characterized in that Formula (1) is selected from one of the following structural formulas, or is one of the following structural formulas in which hydrogen is partially or completely replaced by deuterium or fluorine:

8. A composition, characterized in that The composition comprises a first host compound and a second host compound, wherein the first host compound is selected from the aromatic amine compound according to any one of claims 1 to 7, and the structure of the second host compound is as shown in formula (6): wherein ring B is selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted phenanthrene ring; Y is selected from NR b , CR c R d or oxygen group elements; Z1, Z2, Z3 are each independently selected from N or CR e ; R b , R c , R d Each is independently selected from C1-C30 alkyl, C1-C30 heteroalkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C3-C30 alkylsilyl or C6-C30 arylsilyl; or R c , R d Connect into a ring; R8, R e Each is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphino or C6-C60 arylamine; Wherein, b represents an integer of 0-4; when b is an integer of 2-4, each R8 is the same or different; L3, L4, and L5 are each independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C6-C60 heteroarylene group; Ar3 and Ar4 are each independently selected from substituted or unsubstituted C6-C36 aryl or substituted or unsubstituted C2-C36 heteroaryl; In the ring B, L3, L4, L5, Ar3 and Ar4, the substitution is independently substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl substituted amine, C1-C6 alkyl substituted or unsubstituted C6-C30 aryl, or C1-C6 alkyl substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions ranges from single substitution to the maximum number of substitutions; The heteroatoms in the heteroarylene group, heteroaryl group, heteroalkyl group and heterocycloalkyl group are independently selected from at least one of O, S, N, Se, Si and Ge.

9. The composition according to claim 8, characterized in that The Y is selected from O or S; and / or, the L3, L4, L5 are each independently selected from a single bond, a substituted or unsubstituted C6-C20 arylene group, or a substituted or unsubstituted C6-C20 heteroarylene group; and / or, the Ar3, Ar4 are each independently selected from a substituted or unsubstituted C6-C26 aryl group, or a substituted or unsubstituted C2-C26 heteroaryl group; and / or, the Z1, Z2, Z3 are all selected from N, or one of them is selected from CH, and the other two are selected from N; and / or, R8 is selected from hydrogen or deuterium; and / or, in the ring B, L3, L4, L5, Ar3 and Ar4, the substitution is independently substituted by at least one of deuterium, halogen, cyano, C1-C6 alkyl, C3-C12 cycloalkyl, C6-C20 aryl or C3-C20 heteroaryl, wherein the number of substitutions is from a single substitution to a maximum number of substitutions; and / or, the mass ratio of the first main compound to the second main compound is 8:2-2:

8.

10. The composition according to claim 9, characterized in that Ar3 and Ar4 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted fluoranthene, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted triphenylene radical, substituted or unsubstituted tetramethyltetrahydronaphthyl, substituted or unsubstituted phenanthrothiazolyl, or substituted or unsubstituted phenanthroxazolyl, or substituted or unsubstituted naphthobenzofuran, or substituted or unsubstituted naphthobenzothiophene, or substituted or unsubstituted naphthooxazole, or phenanthrobenzofuran, or a combination of at least two of the foregoing; And / or, L3, L4, L5 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group or a substituted or unsubstituted naphthylene group.

11. The composition according to claim 8, characterized in that Formula (6) is selected from one of the following structural formulas, or is one of the following structural formulas in which hydrogen is partially or completely replaced by deuterium or fluorine:

12. An organic electroluminescent device, characterized in that: The method comprises the aromatic amine compound according to any one of claims 1 to 7 or the composition according to any one of claims 8 to 11.

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